WO2013146617A1 - Easily removable adhesive film and metal plate processing method - Google Patents
Easily removable adhesive film and metal plate processing method Download PDFInfo
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- WO2013146617A1 WO2013146617A1 PCT/JP2013/058432 JP2013058432W WO2013146617A1 WO 2013146617 A1 WO2013146617 A1 WO 2013146617A1 JP 2013058432 W JP2013058432 W JP 2013058432W WO 2013146617 A1 WO2013146617 A1 WO 2013146617A1
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- easily peelable
- metal plate
- adhesive film
- peelable adhesive
- layer
- Prior art date
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Classifications
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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
- C09J7/50—Adhesives in the form of films or foils characterised by a primer layer between the carrier and the adhesive
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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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
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
- C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
-
- 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
- C09J2467/00—Presence of polyester
- C09J2467/003—Presence of polyester in the primer coating
Definitions
- the present invention relates to an easily peelable pressure-sensitive adhesive film preferably used as a temporary fixing sheet for dicing an adherend such as a silicon wafer or a glass wafer, or as a carrier sheet for etching a metal plate.
- an adhesive film having an easy peelability (hereinafter referred to as an easily peelable adhesive film) is attached to the wafer for temporary fixing.
- a method is adopted in which a wafer that is attached and temporarily fixed is subjected to processing such as polishing or dicing, and then the adhesive film is peeled off by reducing the adhesive force of the adhesive film by applying external energy such as light or heat.
- the easily peelable adhesive film is also used as a carrier sheet for etching metal plates.
- an easily peelable adhesive film is affixed to a metal plate such as stainless steel, an etching process is applied to the metal plate so as to have a desired shape, and an undercoat coating solution is applied onto the metal plate as necessary. Transfer the plate to the desired transfer.
- Examples of such an adhesive film include those described in Patent Documents 1 to 3. These prior arts disclose that releasability can be obtained by using an ionizing radiation curable pressure-sensitive adhesive whose adhesive strength is reduced by irradiation with ionizing radiation in the adhesive layer.
- thermosetting resin so as not to decrease the adhesive strength before adhesion of the ionizing radiation curable pressure-sensitive adhesive used in the adhesive layer, but it is usually used as an undercoat layer.
- thermosetting resin it is difficult to obtain an adhesive film excellent in solvent resistance while maintaining the adhesion between the base material and the undercoat layer, and between the undercoat layer and the adhesive layer.
- the present invention relates to a pressure-sensitive adhesive film having an undercoat layer and an easily peelable pressure-sensitive adhesive layer containing an ionizing radiation curable pressure-sensitive adhesive in order on the base material, the adhesion between the base material and the undercoat layer, It aims at providing the easily peelable adhesive film which is excellent also in solvent resistance, maintaining the adhesiveness of a drawing layer and an easily peelable adhesive layer.
- the inventor includes a specific resin and a curing agent in the undercoat layer, so that the adhesion between the base material and the undercoat layer and the adhesion between the undercoat layer and the easily peelable adhesive layer are reduced. It has been found that it can be excellent in solvent resistance while maintaining the properties, and has led to the present invention.
- the easily peelable adhesive film of the present invention is formed by laminating an undercoat layer and an easily peelable adhesive layer in order on a transparent resin film, and the undercoat layer comprises an amine-based curing agent and an acid value. Includes 10 to 100 mg KOH / g of a carboxyl group-containing resin, and the easily peelable pressure-sensitive adhesive layer contains an ionizing radiation curable pressure-sensitive adhesive.
- the easily peelable pressure-sensitive adhesive layer further contains an isocyanate curing agent.
- the ratio of the number of moles of aziridinyl groups contained in the amine-based curing agent to the number of moles of isocyanate groups contained in the isocyanate-based curing agent is preferably 1.5 to 15. It is characterized by this.
- the easily peelable pressure-sensitive adhesive film of the present invention is preferably characterized in that the undercoat layer contains 3 to 30 parts by weight of the amine curing agent with respect to 100 parts by weight of the carboxyl group-containing resin. .
- the easily peelable adhesive film of the present invention is preferably characterized in that the amine curing agent is a trifunctional aziridine compound.
- the processing method of the metal plate of this invention is A) The process of bonding the surface which has the easily peelable adhesion layer of the easily peelable adhesive film of this invention to a metal plate, B) The easy peelability stuck to the metal plate.
- a step of removing the metal plate in a portion where the mask is not formed and D) a step of removing the mask from the metal plate and peeling off the easily peelable adhesive film.
- Either step B) or step C) may precede.
- the easily peelable pressure-sensitive adhesive film of the present invention while maintaining the adhesion between the base material and the undercoat layer and the adhesion between the undercoat layer and the easily peelable pressure-sensitive adhesive layer, it is excellent in solvent resistance. Can do. Therefore, the easily peelable adhesive film is suitably used as a temporary fixing sheet for dicing an adherend such as a silicon wafer or a glass wafer, or as a carrier sheet during metal etching.
- the easily peelable pressure-sensitive adhesive film of the present invention is obtained by laminating an undercoat layer and an easily peelable pressure-sensitive adhesive layer in order on a transparent resin film, and the undercoat layer comprises an amine-based curing agent and an acid.
- the undercoat layer comprises an amine-based curing agent and an acid.
- a carboxyl group-containing resin having a value of 10 to 100 mgKOH / g hereinafter sometimes simply referred to as a carboxyl group-containing resin
- the easily peelable adhesive layer includes an ionizing radiation curable adhesive It is.
- the transparent resin film used in the present invention examples include polyethylene naphthalate, polycarbonate, polyethylene, polypropylene, polybutene, polymethylpentene, polyethylene terephthalate, polybutylene terephthalate, polybutadiene, polyurethane, polystyrene, triacetyl cellulose, acrylic, polyvinyl chloride. And plastic films such as norbornene compounds.
- the polymer film containing the compound which has a carboxyl group as a polymer structural unit, or the laminated body of this and a general purpose polymer film can also be used.
- the thickness of the transparent resin film is preferably 2 to 300 ⁇ m, more preferably 10 to 125 ⁇ m.
- the easily peelable adhesive film of the present invention is transparent so that the mechanism for reducing the adhesive force is not hindered. It is preferable to use a resin film having a total light transmittance of 50% or more, preferably 80% or more based on JIS K7375: 2008.
- the undercoat layer contains an amine-based curing agent and a carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g.
- the amine-based curing agent is crosslinked with the carboxyl group-containing resin in the undercoat layer to improve the solvent resistance of the undercoat layer.
- the carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g also reacts with an ionizing radiation curable adhesive and an isocyanate-based curing agent in the easily peelable adhesive layer described later, whereby the undercoat layer and the easily peelable adhesive layer are reacted. This also improves the adhesion.
- adhesion to the transparent resin film is also improved.
- examples of the amine-based curing agent include aliphatic polyamines such as ethylenediamine, diethylenetriamine and triethylenetetramine, alicyclic polyamines such as isophoronediamine and 1,3-bisaminomethylcyclohexane, aromatics such as diaminodiphenylmethane and diaminodiphenylsulfone.
- Polyamines linear diamines, tetramethylguanidine, triethanolamine, piperidine, pyridine, secondary amines such as benzyldimethylamine or tertiary amines, dimer acid and polyamines such as diethylenetriamine and triethylenetetramine
- the aziridine compound having a polyamidoamine, melamine, or aziridine group (ethyleneimine) obtained in the above can be used.
- An aziridine compound is particularly preferable.
- aziridine compound examples include monofunctional aziridine compounds (eg, aziridine, 2-methylaziridine, 2-ethylaziridine, 2,2-dimethylaziridine, 2,3-dimethylaziridine, 2-phenylaziridine, etc.), bifunctional aziridine compounds (For example, neopentyl glycol di ( ⁇ -aziridinylpropionate), 4,4′-isopropylidenediphenoldi ( ⁇ -aziridinylpropionate), 4,4′-methylenediphenoldi ( ⁇ -Aziridinylpropionate), etc.) trifunctional aziridine compounds (eg tetramethylolmethane-tri- ( ⁇ -aziridinylpropionate), trimethylolpropane tris ( ⁇ -aziridinylpropionate), Glyceryl tris ( ⁇ -aziridinyl propionate), etc.) Aziridine compounds (for example, tetraaziridinyl
- the carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g means a resin having at least one carboxyl group in the molecule, specifically, a (meth) acrylic copolymer, a vinyl copolymer.
- a coalescence, a polyurethane-based resin, a polyester-based resin, a polycarbonate-based resin, a polyamide resin, a polyimide resin, and the like can be given. These can be used alone or in combination of two or more. Among these, from the viewpoint of adhesion between the transparent resin film and the undercoat layer, a polyester resin is preferably used.
- polyester resin having an acid value of 10 to 100 mgKOH / g examples include polyester resins such as polyethylene terephthalate, polybutylene terephthalate, polyarylate, polyethylene naphthalate, and ethylene-terephthalate-isophthalate copolymer. These resins may be used alone or in combination of two or more (for example, as a mixture of two or more).
- the acid value of the polyester resin is preferably 20 to 80 mgKOH / g.
- the content ratio of the carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g and the amine curing agent is preferably 3 to 30 parts by weight of the amine curing agent with respect to 100 parts by weight of the carboxyl group-containing resin. .
- the content ratio of the carboxyl group-containing resin and the amine curing agent described above is preferably 5 to 20 parts by weight.
- the undercoat layer contains particles.
- an uneven shape is formed on the surface of the undercoat layer, and the uneven shape enters the interface of the easily peelable adhesive layer and exhibits an anchoring effect on the adherend. Become. Thereby, the initial adhesive force to the adherend is further improved.
- Such particles include resin particles such as acrylic resin particles, silicone resin particles, nylon resin particles, styrene resin particles, polyethylene resin particles, benzoguanamine resin particles, urethane resin particles, silica, clay , Inorganic particles such as talc, calcium carbonate, calcium sulfate, barium sulfate, aluminum silicate, titanium oxide, synthetic zeolite, alumina, and smectite.
- resin particles such as acrylic resin particles, silicone resin particles, nylon resin particles, styrene resin particles, polyethylene resin particles, benzoguanamine resin particles, urethane resin particles, silica, clay , Inorganic particles such as talc, calcium carbonate, calcium sulfate, barium sulfate, aluminum silicate, titanium oxide, synthetic zeolite, alumina, and smectite.
- the particle diameter of the particles is not limited, but the average particle diameter is preferably 0.3 ⁇ m to 12 ⁇ m, more preferably 0.7 ⁇ m to 6 ⁇ m.
- the content of the particles is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight with respect to 100 parts by weight of the resin of the undercoat layer.
- the “particle diameter” refers to a value calculated by converting a particle volume measured by the Coulter counter method into a sphere.
- the undercoat layer has a crosslinking agent such as an alkyl etherified aminoformaldehyde resin, polyisocyanates, block isocyanates, polyanilines, polythiophenes, polypyrroles, polyfurans, as long as the function of the present invention is not impaired.
- Anti-static agents such as polyacetylenes, polyphenylenes, polyphenylene vinylenes, polyacenes polythiophene vinylenes, antifoaming agents, anti-slip agents, antiseptics, rust inhibitors, pH adjusters, antioxidants, pigments other than those mentioned above, Dyes, lubricants, and the like can be included as appropriate.
- the thickness of the undercoat layer is not particularly limited, but is preferably 0.2 ⁇ m to 10 ⁇ m, more preferably 0.5 ⁇ m to 5 ⁇ m, in order to improve the adhesion between the substrate and the easily peelable adhesive layer.
- the easily peelable pressure-sensitive adhesive layer contains an ionizing radiation curable pressure-sensitive adhesive.
- the ionizing radiation curable pressure-sensitive adhesive is firmly attached to an adherend such as a metal plate before irradiation with ionizing radiation (ultraviolet light or electron beam), and does not peel off even if immersed in an etching solution after irradiation. It must prevent erosion of the etchant.
- the ionizing radiation curable pressure-sensitive adhesive constituting such an easily peelable pressure-sensitive adhesive layer is mainly formed from an acrylic copolymer and an ionizing radiation polymerizable compound.
- Acrylic copolymers include homopolymers mainly composed of esters of acrylic acid or methacrylic acid, acrylic acid or methacrylic acid or esters thereof or acid amides thereof, and other copolymerizable comonomers. It is a copolymer or a mixture of these polymers.
- alkyl esters of acrylic acid or methacrylic acid such as methyl ester, ethyl ester, butyl ester, 2-ethylhexyl ester, octyl ester, glycidyl ester, hydroxymethyl ester, 2-hydroxyethyl ester, hydroxypropyl ester
- amides of acrylic acid or methacrylic acid and N-substituted amides such as N-hydroxymethylacrylic acid amide or methacrylic acid amide.
- the ionizing radiation polymerizable compound is a compound containing two or more functional groups having a carbon-carbon double bond such as an acrylate group in one molecule. This is because the acrylate group is preferable from the viewpoints of reactivity and workability, such as relatively high reactivity with ionizing radiation, and selection of various acrylic pressure-sensitive adhesives.
- Examples of the ionizing radiation polymerizable compound containing two or more carbon-carbon double bonds in one molecule include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate.
- the blending amount of the ionizing radiation polymerizable compound in the easily peelable pressure-sensitive adhesive layer varies depending on the type of the selected compound, so it cannot be generally stated.
- 100 weight of acrylic copolymer in the ionizing radiation curable pressure sensitive adhesive The amount is about 0.5 to 200 parts by weight, more preferably about 1 to 50 parts by weight. If the blending amount of the ionizing radiation polymerizable compound is too large relative to the blending amount of the acrylic copolymer, the content of the low molecular weight substance is increased, and it is difficult to maintain the shape and performance as an easily peelable adhesive layer. There is a tendency to become.
- the amount of the ionizing radiation polymerizable compound is too small relative to the amount of the acrylic copolymer, even if the ionizing radiation is applied, the tack of the easily peelable adhesive layer remains and the adhesive film is peeled off. When doing so, there is a possibility that adhesive remains on the adherend such as a metal plate.
- the easily peelable adhesive layer is used by being cured by irradiation with ultraviolet rays as ionizing radiation, it is preferable to use additives such as a photopolymerization initiator, a photopolymerization accelerator, and an ultraviolet sensitizer.
- photopolymerization initiator examples include acetophenone, benzophenone, Michler's ketone, benzoin, benzylmethyl ketal, benzoylbenzoate, ⁇ -acyloxime ester, thioxanthone and the like.
- the photopolymerization accelerator can reduce the polymerization obstacle due to air at the time of curing and increase the curing speed.
- examples thereof include p-dimethylaminobenzoic acid isoamyl ester and p-dimethylaminobenzoic acid ethyl ester.
- Examples of the ultraviolet sensitizer include n-butylamine, triethylamine, and tri-n-butylphosphine.
- the easily peelable adhesive layer contains an isocyanate curing agent.
- an isocyanate-based curing agent in the easily peelable adhesive layer, not only the coating strength of the easily peelable adhesive layer is improved by crosslinking with the ionizing radiation curable adhesive when forming the easily peelable adhesive layer, Since the carboxyl group-containing resin in the undercoat layer is also cross-linked, the adhesion between the easily peelable adhesive layer and the undercoat layer is also improved.
- the isocyanate curing agent may be any polyfunctional compound having two or more isocyanate groups, such as diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, phenylene diisocyanate, 1,5- Aromatic diisocyanates such as naphthylene diisocyanate, xylylene diisocyanate, toluylene diisocyanate; aliphatic or cycloaliphatic diisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, 4,4′-dicyclohexylmethane diisocyanate.
- isocyanate groups such as diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, phenylene diisocyanate, 1,5- Aromatic diisocyanates such as naphthylene diisocyanate,
- the isocyanate curing agent is 0.1 to 10 parts by weight with respect to 100 parts by weight of the ionizing radiation curable adhesive.
- the adhesion between the undercoat layer and the easily peelable adhesive layer can be made more satisfactory.
- the adhesive force before ionizing radiation irradiation can be hold
- the ratio (molar ratio) of the number of moles of the aziridinyl group contained in the amine-based curing agent in the undercoat layer to the number of moles of the isocyanate group contained in the isocyanate-based curing agent in the easily peelable adhesive layer is 1. It is preferably 5 to 15.
- the molar ratio of the aziridinyl group to the isocyanate group within such a range, the balance between the crosslinking between the isocyanate curing agent and the hydroxyl group-containing resin and the crosslinking between the amine curing agent and the hydroxyl group-containing resin is suitable.
- the solvent resistance of the undercoat layer can be made particularly excellent, but also the adhesion between the undercoat layer and the easily peelable adhesive layer can be further improved.
- such an easily peelable pressure-sensitive adhesive layer may include other crosslinking agents such as alkyl etherified melamine compounds, tackifiers (for example, rosin derivative resins, polyterpene resins, petroleum resins, oil-soluble phenol resins). Etc.), additives such as plasticizers, fillers and anti-aging agents may be included as appropriate.
- crosslinking agents such as alkyl etherified melamine compounds, tackifiers (for example, rosin derivative resins, polyterpene resins, petroleum resins, oil-soluble phenol resins). Etc.), additives such as plasticizers, fillers and anti-aging agents may be included as appropriate.
- the thickness of the easily peelable pressure-sensitive adhesive layer is not particularly limited, but is 5 ⁇ m to 100 ⁇ m, preferably 7 ⁇ m to 50 ⁇ m, more preferably 10 ⁇ m to 30 ⁇ m from the viewpoint of appropriate punching processing and prevention of etching solution penetration.
- the pressure-sensitive adhesive film used in the present invention is preferably provided with a separator on the surface of the easily peelable pressure-sensitive adhesive layer from the viewpoint of handleability.
- a separator is not particularly limited.
- a plastic film having a release treatment applied to one surface of the plastic film is not particularly limited.
- polyethylene laminated paper polypropylene, polyethylene, polyester, polycarbonate, triacetyl cellulose, polyvinyl chloride, acrylic, polystyrene, polyamide, polyimide, vinylidene chloride-vinyl chloride copolymer.
- a plastic film having a release treatment applied to one surface of the plastic film for example, polyethylene laminated paper, polypropylene, polyethylene, polyester, polycarbonate
- the thickness of the separator is not particularly limited, but considering the handleability, a separator having a thickness of 10 ⁇ m to 250 ⁇ m, preferably 20 ⁇ m to 125 ⁇ m, more preferably 30 ⁇ m to 100 ⁇ m is used.
- the material constituting the undercoat layer described above is mixed to form an undercoat layer coating solution, and a conventionally known coating method such as a bar
- a conventionally known coating method such as a bar
- coater, die coater, blade coater, spin coater, roll coater, gravure coater, flow coater, spray, screen printing, etc. it is dried as necessary, and then constitutes an easily peelable adhesive layer It can be obtained by mixing the materials to be prepared into an easily peelable adhesive layer coating solution, and similarly applying the coating onto the undercoat layer by a conventionally known coating method, followed by heating and drying as necessary.
- the separator mentioned above is bonded together to the said easily peelable adhesion layer as needed.
- an undercoat layer is formed on one surface of the transparent resin film in the same manner as described above, and an easily peelable adhesive layer is formed on the separator in the same manner as described above, and then the transparent resin is formed.
- a carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g contained in the undercoat layer coating solution and an isocyanate curing agent contained in the easily peelable adhesive layer coating solution.
- the undercoat layer and the easily peelable adhesive layer contain a carboxyl group in the undercoat layer before they are bonded together. It is preferable that the reaction between the resin and the amine curing agent and the reaction between the ionizing radiation curable resin and the isocyanate curing agent in the easily peelable adhesive layer are not completed.
- the easily peelable adhesive film of the present invention can be used as a general adhesive film.
- it is suitable as an adhesive film for temporary fixing when processing semiconductor materials such as glass and silicon, and as a carrier sheet for etching metal plates. Adhesion with the layer can be maintained, and the workability can be improved.
- the processing method of the metal plate of the present invention includes: A) a step of bonding the surface having the easily peelable adhesive layer of the easily peelable adhesive film of the present invention to the metal plate, and B) sticking the easily peelable adhesive film.
- a step of irradiating the exposed surface with ionizing radiation and curing the easily peelable adhesive layer C) attaching a mask member to the surface of the metal plate opposite to the surface having the easily peelable adhesive film, and using the metal plate as an etching solution Dipping and removing the unmasked portion of the metal plate of the mask member, and D) peeling the mask member and the easily peelable adhesive film from the metal plate.
- Either the easily peelable adhesive layer curing step B) or the metal plate removing step C) may precede either.
- the metal plate processing method of the present invention further includes, after the metal plate removing step C), E) applying a subbing coating solution to the metal plate and transferring the metal plate to a desired transfer product.
- the transfer step E) is preferably performed after peeling the mask member in step D) and before peeling the easily peelable adhesive film.
- the easily peelable adhesive layer curing step B) may be performed after the transfer step E), before the metal plate removing step C), or before the metal plate removing step C, if it is before peeling the easily peelable adhesive film.
- transfer step E) may be performed after the transfer step E), before the metal plate removing step C), or before the metal plate removing step C, if it is before peeling the easily peelable adhesive film.
- the metal plate processing method of the present invention is characterized in that the easily peelable adhesive film of the present invention is used as a carrier sheet for etching a metal plate.
- the material used in each step and the conditions of each step are metal Conventional materials and processing conditions can be employed depending on the purpose and application of processing.
- the mask member may be a photoresist coating film as well as a sheet-like member, and the etching solution and etching conditions are appropriately changed according to the type and thickness of the target metal.
- a carboxyl group-containing resin of 100 mg KOH / g and adopting a configuration containing an ionizing radiation curable pressure-sensitive adhesive in the easily peelable pressure-sensitive adhesive layer for example, it becomes excellent in solvent resistance when used in metal etching applications.
- Example 1 Preparation of easily peelable protective adhesive film [Example 1] The undercoat layer coating solution below is applied to one side of a 100 ⁇ m thick polyethylene terephthalate film (Lumirror S10: Toray) as a transparent resin film to form an undercoat layer with a thickness of 0.5 ⁇ m. did. Next, an easily peelable adhesive layer coating solution having the following formulation is applied onto the undercoat layer by a bar coater method to form a 25 ⁇ m thick easily peelable adhesive layer, and the undercoat layer and the easily peelable adhesive layer are heated. , Dried.
- a bar coater method to form a 25 ⁇ m thick easily peelable adhesive layer
- Example 2 A releasable pressure-sensitive adhesive film of Example 2 was produced in the same manner as in Example 1 except that the particles contained in the undercoat layer coating solution of Example 1 were removed.
- Example 3 The releasable adhesive of Example 3 in the same manner as in Example 1 except that the weight part of the amine-based curing agent contained in the coating solution for the undercoat layer of Example 1 was 6.6 parts, and the particles were removed. A film was prepared.
- Example 4 The releasable pressure-sensitive adhesive film of Example 4 was prepared in the same manner as in Example 1 except that 107 parts by weight of the amine-based curing agent contained in the coating solution for the undercoat layer of Example 1 and excluding the particles. Produced.
- the molar ratio of the aziridinyl group contained in the amine-based curing agent in the undercoat layer to the isocyanate group contained in the isocyanate-based curing agent in the easily peelable adhesive layer was 1.5. Within the range of ⁇ 15.
- Comparative Example 1 A re-peelable pressure-sensitive adhesive film of Comparative Example 1 was produced in the same manner as in Example 1 except that the amine-based curing agent contained in the coating liquid for the undercoat layer of Example 1 was removed.
- Comparative Example 2 An easily peelable adhesive film of Comparative Example 2 was produced in the same manner as in Example 1 except that the undercoat layer coating solution of Example 1 was changed to the undercoat layer coating solution described below.
- Comparative Example 3 Comparative Example 2 was the same as Comparative Example 2 except that 9 parts by weight of bifunctional acrylate monomer (Kayarad R-167, Nippon Kayaku Co., Ltd., solid content 100%) was added to the undercoat layer coating solution. The removable adhesive film of Comparative Example 3 was produced.
- bifunctional acrylate monomer Kayarad R-167, Nippon Kayaku Co., Ltd., solid content 100%
- Comparative Example 4 An easily peelable adhesive film of Comparative Example 4 was produced in the same manner as in Example 1, except that the undercoat layer coating solution of Example 1 was changed to the undercoat layer coating solution described below.
- the easily peelable adhesive films of Examples 1 to 4 include an amine-based curing agent and a carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g on a transparent resin film. Since it has an undercoat layer and an easily peelable adhesive layer containing an ionizing radiation curable adhesive in order, the cross-cut peel evaluation is good, the adhesion between the substrate and the undercoat layer, and the undercoat layer The adhesiveness with the peelable adhesive layer was excellent. Moreover, it was excellent also in the solvent resistance test using toluene.
- the easily peelable adhesive films of Example 1 and Example 2 contained 2 to 30 parts by weight of the amine curing agent with respect to 100 parts by weight of the carboxyl group-containing resin. It was excellent in adhesion to the easily peelable adhesive layer and solvent resistance.
- Example 1 when Example 1 is compared with Example 2, since the easily peelable adhesive film of Example 1 contains particles in the undercoat layer, the surface unevenness formed by the particles has an anchoring effect on the adhesive layer. As a result, the adhesion between the undercoat layer and the easily peelable adhesive layer and the initial adhesiveness were superior to those of Example 2.
- the easily peelable adhesive film of Comparative Example 1 did not contain an amine-based curing agent in the undercoat layer, the adhesion between the base material and the undercoat layer, and the undercoat layer and the easily peelable adhesive film. It was inferior in the adhesiveness with a layer, and also in the solvent resistance test using toluene.
- the easily peelable adhesive film of the comparative example 2 uses an isocyanate hardening agent instead of an amine hardening agent for the undercoat layer
- the substrate and the undercoat layer are different from the comparative example 1.
- the adhesion and the adhesion between the undercoat layer and the easily peelable adhesive layer could not be improved.
- the easy-peelable adhesive film of Comparative Example 3 is not an amine-based curing agent in order to improve the adhesion between the base material and the undercoat layer and the adhesion between the undercoat layer and the easily peelable adhesive layer.
- the easily peelable adhesive film of Comparative Example 4 had an amine-based curing agent and a carboxyl group-containing resin, the acid value of the carboxyl group-containing resin was less than 10 mgKOH / g. It was inferior in the adhesiveness with an easily peelable adhesion layer, and inferior also in the solvent-resistance test using toluene.
Abstract
Description
[実施例1]
透明樹脂フィルムとして厚み100μmのポリエチレンテレフタレートフィルム(ルミラーS10:東レ社)の一方の面に、下記処方の下引層用塗布液をバーコーター法により塗布し、厚み0.5μmの下引層を形成した。次いで、当該下引層上に下記処方の易剥離性粘着層用塗布液をバーコーター法により塗布し、厚み25μmの易剥離性粘着層を形成し、下引層及び易剥離性粘着層を加熱、乾燥させた。次いで、当該易剥離性粘着層上にセパレータ(厚み25μm、ポリエチレンナフタレートフィルム、MRF:三菱化学ポリエステルフィルム社)の離型処理面を貼り合わせ、実施例1の再剥離性保護粘着フィルムを作製した。 1. Preparation of easily peelable protective adhesive film [Example 1]
The undercoat layer coating solution below is applied to one side of a 100 μm thick polyethylene terephthalate film (Lumirror S10: Toray) as a transparent resin film to form an undercoat layer with a thickness of 0.5 μm. did. Next, an easily peelable adhesive layer coating solution having the following formulation is applied onto the undercoat layer by a bar coater method to form a 25 μm thick easily peelable adhesive layer, and the undercoat layer and the easily peelable adhesive layer are heated. , Dried. Subsequently, the release treatment surface of a separator (thickness 25 μm, polyethylene naphthalate film, MRF: Mitsubishi Chemical Polyester Film Co., Ltd.) was bonded to the easily peelable adhesive layer, and the releasable protective adhesive film of Example 1 was produced. .
・ポリエステル系樹脂 100部
(UR1700:東洋紡績社、酸価:26mgKOH/g、固形分100%)
・アミン系硬化剤 29部
(TAZO:相互薬工社、固形分30%)
・粒子(シリコーン樹脂粒子、平均粒子径:3μm) 1.1部
(トスパール130:モメンティブ・パフォーマンス・マテリアルズ社)
・希釈溶剤 942部 <Coating liquid for undercoat layer of Example 1>
・ 100 parts of polyester resin (UR1700: Toyobo Co., Ltd., acid value: 26 mgKOH / g, solid content: 100%)
・ Amine-based curing agent 29 parts (TAZO: Mutual Pharmaceutical Company, solid content 30%)
・ Particles (silicone resin particles, average particle size: 3 μm) 1.1 parts (Tospearl 130: Momentive Performance Materials)
・ 942 parts diluted solvent
・電離放射線硬化型粘着剤 100部
(コーポニールN7271:日本合成化学社、固形分40%)
・イソシアネート系硬化剤 0.55部
(コロネートL45E:日本ポリウレタン社、固形分45%)
・重合開始剤 1.4部
(イルガキュア184:BASF社、固形分100%)
・希釈溶剤 38部 <Coating liquid for easily peelable adhesive layer of Example 1>
・ Ionizing radiation curable adhesive 100 parts (Cooponyl N7271: Nippon Synthetic Chemical Co., Ltd., solid content 40%)
・ Isocyanate-based curing agent 0.55 parts (Coronate L45E: Nippon Polyurethane, solid content 45%)
-Polymerization initiator 1.4 parts (Irgacure 184: BASF Corporation, solid content 100%)
・ 38 parts of diluted solvent
実施例1の下引層用塗布液中に含まれる粒子を除いた以外は実施例1と同様にして、実施例2の再剥離性粘着フィルムを作製した。 [Example 2]
A releasable pressure-sensitive adhesive film of Example 2 was produced in the same manner as in Example 1 except that the particles contained in the undercoat layer coating solution of Example 1 were removed.
実施例1の下引層用塗布液中に含まれるアミン系硬化剤の重量部を6.6部とし、粒子を除いた以外は実施例1と同様にして、実施例3の再剥離性粘着フィルムを作製した。 [Example 3]
The releasable adhesive of Example 3 in the same manner as in Example 1 except that the weight part of the amine-based curing agent contained in the coating solution for the undercoat layer of Example 1 was 6.6 parts, and the particles were removed. A film was prepared.
実施例1の下引層用塗布液中に含まれるアミン系硬化剤の重量部を107部とし、粒子を除いた以外は実施例1と同様にして、実施例4の再剥離性粘着フィルムを作製した。
なお実施例1~4において、易剥離性粘着層中のイソシアネート系硬化剤に含まれるイソシアネート基に対する、下引層中のアミン系硬化剤に含まれるアジリジニル基のモル比は、いずれも1.5~15の範囲内である。 [Example 4]
The releasable pressure-sensitive adhesive film of Example 4 was prepared in the same manner as in Example 1 except that 107 parts by weight of the amine-based curing agent contained in the coating solution for the undercoat layer of Example 1 and excluding the particles. Produced.
In Examples 1 to 4, the molar ratio of the aziridinyl group contained in the amine-based curing agent in the undercoat layer to the isocyanate group contained in the isocyanate-based curing agent in the easily peelable adhesive layer was 1.5. Within the range of ~ 15.
実施例1の下引層用塗布液中に含まれるアミン系硬化剤を除いた以外は実施例1と同様にして、比較例1の再剥離性粘着フィルムを作製した。 [Comparative Example 1]
A re-peelable pressure-sensitive adhesive film of Comparative Example 1 was produced in the same manner as in Example 1 except that the amine-based curing agent contained in the coating liquid for the undercoat layer of Example 1 was removed.
実施例1の下引層用塗布液を下記処方の下引層用塗布液に変更した以外は、実施例1と同様にして、比較例2の易剥離性粘着フィルムを作製した。 [Comparative Example 2]
An easily peelable adhesive film of Comparative Example 2 was produced in the same manner as in Example 1 except that the undercoat layer coating solution of Example 1 was changed to the undercoat layer coating solution described below.
・ポリエステル系樹脂 100部
(アクリットER20:大成化工社、酸価:2mgKOH/g、固形分40%)
・イソシアネート系硬化剤 4.9部
(タケネートD110N:三井化学社、固形分60%)
・希釈溶剤 225部 <Coating liquid for undercoat layer of Comparative Example 2>
・ 100 parts of polyester resin (Acryt ER20: Taisei Kako Co., Ltd., acid value: 2 mgKOH / g, solid content 40%)
・ Isocyanate curing agent 4.9 parts (Takenate D110N: Mitsui Chemicals, solid content 60%)
・ Diluted solvent 225 parts
比較例2の下引層用塗布液に、二官能基アクリレートモノマー(カヤラッドR-167、日本化薬社、固形分100%)を9重量部追加した以外は、比較例2と同様にして、比較例3の再剥離性粘着フィルムを作製した。 [Comparative Example 3]
Comparative Example 2 was the same as Comparative Example 2 except that 9 parts by weight of bifunctional acrylate monomer (Kayarad R-167, Nippon Kayaku Co., Ltd., solid content 100%) was added to the undercoat layer coating solution. The removable adhesive film of Comparative Example 3 was produced.
実施例1の下引層用塗布液を下記処方の下引層用塗布液に変更した以外は、実施例1と同様にして、比較例4の易剥離性粘着フィルムを作製した。 [Comparative Example 4]
An easily peelable adhesive film of Comparative Example 4 was produced in the same manner as in Example 1, except that the undercoat layer coating solution of Example 1 was changed to the undercoat layer coating solution described below.
・ポリエステル系樹脂 100部
(バイロン200:東洋紡績社、酸価:2mgKOH/g、固形分100%)
・アミン系硬化剤 29部
(TAZO:相互薬工社、固形分30%)
・希釈溶剤 932部 <Coating liquid for undercoat layer of Comparative Example 4>
・ 100 parts of polyester resin (Byron 200: Toyobo Co., Ltd., acid value: 2 mgKOH / g, solid content: 100%)
・ Amine-based curing agent 29 parts (TAZO: Mutual Pharmaceutical Company, solid content 30%)
・ Dilution solvent 932 parts
(1)密着性
実施例1~4及び比較例1~4の易剥離性粘着フィルムからそれぞれセパレータを剥離して易剥離性粘着層を露出させ、透明樹脂フィルム側からメタルハライドランプにより400mJ/cm2の紫外線を照射して、電離放射線硬化型粘着剤を硬化させた。その後、当該易剥離性粘着フィルムについてJIS-K5400 1990における碁盤目テープ法に基づき測定して評価した。碁盤目部分が1個も剥離しなかったものを「○」、碁盤目部分が5個未満で剥離してしまったものを「△」、碁盤目部分が5個を超えて剥離してしまったものを「×」とした。測定結果を表1に示す。 2. Evaluation (1) Adhesiveness The separators were peeled off from the easily peelable adhesive films of Examples 1 to 4 and Comparative Examples 1 to 4 to expose the easily peelable adhesive layers, and 400 mJ / cm from the transparent resin film side using a metal halide lamp. The ultraviolet ray of 2 was irradiated to cure the ionizing radiation curable pressure-sensitive adhesive. Thereafter, the easily peelable pressure-sensitive adhesive film was measured and evaluated based on the cross-cut tape method in JIS-K5400 1990. “○” indicates that none of the cross section was peeled off, “△” indicates that the cross section was peeled off with less than 5 pieces, and the cross section was peeled off over 5 pieces. The thing was made into "x". The measurement results are shown in Table 1.
実施例1~4及び比較例1~4易剥離性粘着フィルムからそれぞれセパレータを剥離して易剥離性粘着層を露出させ、透明樹脂フィルム側からメタルハライドランプにより400mJ/cm2の紫外線を照射して、電離放射線硬化型粘着剤を硬化させた。その後、当該易剥離性粘着層表面にトルエンを数滴滴下した。滴下後5分間放置したが、当該易剥離性粘着層を観察し、端部に剥がれが生じなかったものを「○」、2分以上5分未満放置したが、当該易剥離性粘着層を観察し、端部に剥がれが生じなかったものを「△」、滴下直後に端部に剥がれが生じたものを「×」とした。測定結果を表1に示す。 (2) Solvent resistance (droplet evaluation)
Examples 1 to 4 and Comparative Examples 1 to 4 The separator was peeled off from the easily peelable adhesive film to expose the easily peelable adhesive layer, and ultraviolet rays of 400 mJ / cm 2 were irradiated from the transparent resin film side by a metal halide lamp. The ionizing radiation curable adhesive was cured. Thereafter, several drops of toluene were dropped on the surface of the easily peelable adhesive layer. Although it was allowed to stand for 5 minutes after the dropping, the easily peelable adhesive layer was observed, and “○” indicates that no peeling occurred at the end, but it was allowed to stand for 2 minutes or more but less than 5 minutes, but the easily peelable adhesive layer was observed. Then, the case where peeling did not occur at the end portion was designated as “Δ”, and the case where peeling occurred at the end portion immediately after the dropping was designated as “x”. The measurement results are shown in Table 1.
また、(2)に並行して、上述のように電離放射線硬化型粘着剤を硬化させた後、当該易剥離性粘着層表面を、トルエンを染み込ませたウエスにて10往復擦り、当該易剥離性粘着層を観察した。当該易剥離性粘着層の端部に剥がれが生じなかったものを「○」、剥がれが生じたものを「×」とした。評価結果を表1に示す。 (3) Solvent resistance (rubbing evaluation)
In parallel with (2), after the ionizing radiation curable pressure-sensitive adhesive is cured as described above, the surface of the easily peelable adhesive layer is rubbed 10 times with a waste soaked in toluene, and the easily peelable The adhesive layer was observed. The case where peeling did not occur at the end of the easily peelable pressure-sensitive adhesive layer was “◯”, and the case where peeling occurred was “x”. The evaluation results are shown in Table 1.
比較例3の易剥離性粘着フィルムは、基材と下引層との密着性、及び下引層と易剥離性粘着層との密着性を向上させるために、アミン系硬化剤ではなく、二官能基アクリレートモノマーを用いたものであるが、アミン系硬化剤を用いた実施例に比べ、基材と下引層との密着性、及び下引層と易剥離性粘着層との密着性に劣り、また、トルエンを用いた耐溶剤性試験にも劣るものであった。 Moreover, although the easily peelable adhesive film of the comparative example 2 uses an isocyanate hardening agent instead of an amine hardening agent for the undercoat layer, the substrate and the undercoat layer are different from the comparative example 1. The adhesion and the adhesion between the undercoat layer and the easily peelable adhesive layer could not be improved.
The easy-peelable adhesive film of Comparative Example 3 is not an amine-based curing agent in order to improve the adhesion between the base material and the undercoat layer and the adhesion between the undercoat layer and the easily peelable adhesive layer. Although it uses a functional group acrylate monomer, compared to the examples using an amine curing agent, the adhesion between the substrate and the undercoat layer, and the adhesion between the undercoat layer and the easily peelable adhesive layer In addition, it was inferior to the solvent resistance test using toluene.
Moreover, although the easily peelable adhesive film of Comparative Example 4 had an amine-based curing agent and a carboxyl group-containing resin, the acid value of the carboxyl group-containing resin was less than 10 mgKOH / g. It was inferior in the adhesiveness with an easily peelable adhesion layer, and inferior also in the solvent-resistance test using toluene.
Claims (8)
- 透明樹脂フィルム上に、下引層と、易剥離性粘着層とが順に積層されてなる易剥離性粘着フィルムであって、
前記下引層は、アミン系硬化剤及び酸価が10~100mgKOH/gのカルボキシル基含有樹脂を含み、
前記易剥離性粘着層は、電離放射線硬化型粘着剤を含むことを特徴とする易剥離性粘着フィルム。 An easily peelable adhesive film in which an undercoat layer and an easily peelable adhesive layer are laminated in order on a transparent resin film,
The undercoat layer includes an amine curing agent and a carboxyl group-containing resin having an acid value of 10 to 100 mgKOH / g,
The easy-peelable adhesive layer contains an ionizing radiation curable pressure-sensitive adhesive. - 前記易剥離性粘着層は、イソシアネート系硬化剤をさらに含むことを特徴とする請求項1に記載の易剥離性粘着フィルム。 The easily peelable pressure-sensitive adhesive film according to claim 1, wherein the easily peelable pressure-sensitive adhesive layer further contains an isocyanate curing agent.
- 前記イソシアネート系硬化剤に含まれるイソシアネート基のモル数に対する、前記アミン系硬化剤に含まれるアジリジニル基のモル数の割合が、1.5~15であることを特徴とする請求項2に記載の易剥離性粘着フィルム。 The ratio of the number of moles of aziridinyl groups contained in the amine-based curing agent to the number of moles of isocyanate groups contained in the isocyanate-based curing agent is 1.5 to 15. Easy peelable adhesive film.
- 前記下引層は、前記カルボキシル基含有樹脂100重量部に対し、前記アミン系硬化剤を3~30重量部含有することを特徴とする請求項1~3何れか1項に記載の易剥離性粘着フィルム。 The easily peelable layer according to any one of claims 1 to 3, wherein the undercoat layer contains 3 to 30 parts by weight of the amine curing agent with respect to 100 parts by weight of the carboxyl group-containing resin. Adhesive film.
- 前記アミン系硬化剤は、3官能アジリジン化合物であることを特徴とする請求項1~4何れか1項に記載の易剥離性粘着フィルム。 The easily peelable adhesive film according to any one of claims 1 to 4, wherein the amine curing agent is a trifunctional aziridine compound.
- A)金属板に、請求項1~5何れか1項記載の易剥離性粘着フィルムの易剥離性粘着層を有する面を貼り合わせる工程、
B)金属板に貼着した易剥離性粘着フィルムに電離放射線を照射し、易剥離性粘着層を硬化させる工程、
C)金属板の易剥離性粘着フィルムを有する面とは反対面にマスクを形成し、前記金属板をエッチング液に浸し前記マスクが形成されていない部分の金属板を除去する工程、
D)金属板からマスクを除去し、易剥離性粘着フィルムを剥離する工程、
を含むことを特徴とする金属板の加工方法。 A) a step of bonding a surface having an easily peelable adhesive layer of the easily peelable adhesive film according to any one of claims 1 to 5 to a metal plate;
B) The process of irradiating the easily peelable adhesive film stuck to the metal plate with ionizing radiation and curing the easily peelable adhesive layer,
C) forming a mask on the surface of the metal plate opposite to the surface having the easily peelable adhesive film, immersing the metal plate in an etching solution, and removing the portion of the metal plate where the mask is not formed;
D) A process of removing the mask from the metal plate and peeling the easily peelable adhesive film,
The metal plate processing method characterized by including. - B)の工程を、C)の工程の後に行うことを特徴とする請求項6に記載の金属板の加工方法。 The method for processing a metal plate according to claim 6, wherein the step B) is performed after the step C).
- D)の工程において、金属板からマスクを除去した後、易剥離性粘着フィルムを剥離する前に、
E)金属板を被転写物に転写する工程を含むことを特徴とする請求項6又は7に記載の金属板の加工方法。
In step D), after removing the mask from the metal plate, before peeling the easily peelable adhesive film,
E) The method of processing a metal plate according to claim 6 or 7, further comprising a step of transferring the metal plate to a transfer object.
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