WO2014021107A1 - 粘着剤 - Google Patents

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Publication number
WO2014021107A1
WO2014021107A1 PCT/JP2013/069431 JP2013069431W WO2014021107A1 WO 2014021107 A1 WO2014021107 A1 WO 2014021107A1 JP 2013069431 W JP2013069431 W JP 2013069431W WO 2014021107 A1 WO2014021107 A1 WO 2014021107A1
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WO
WIPO (PCT)
Prior art keywords
polyol
pressure
sensitive adhesive
groups
weight
Prior art date
Application number
PCT/JP2013/069431
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
亮 伊関
翔悟 佐々木
創矢 徐
安藤　雅彦
Original Assignee
日東電工株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Priority to CN201380040539.3A priority Critical patent/CN104508068B/zh
Priority to KR1020147036510A priority patent/KR102062417B1/ko
Publication of WO2014021107A1 publication Critical patent/WO2014021107A1/ja

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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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C08G18/8029—Masked aromatic polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2405/00—Adhesive articles, e.g. adhesive tapes
    • 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
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • C09J2475/00—Presence of polyurethane

Definitions

  • the present invention relates to an adhesive.
  • the pressure-sensitive adhesive of the present invention has excellent initial reworkability when adhered to an adherend and excellent adhesion reliability after aging.
  • this invention relates to the adhesive sheet which has an adhesive layer which consists of such an adhesive on the at least single side
  • this invention relates to the surface protection film which has the adhesive layer which consists of such an adhesive on the single side
  • the pressure-sensitive adhesive sheet of the present invention is preferably used, for example, for applications in which various members such as optical members and electronic members are adhesively fixed.
  • the surface protective film of the present invention is preferably used for, for example, an application of protecting the surface by sticking to the surface of an optical member or an electronic member.
  • a surface protective film is attached to the surface side. Such a surface protective film is peeled off from the optical member or the electronic member when the surface protection is no longer necessary.
  • a surface protective film using a silicone resin having a high wetting speed as an adhesive layer is known.
  • silicone resin used for the pressure-sensitive adhesive layer
  • the pressure-sensitive adhesive component easily contaminates the adherend, and surface protection for protecting the surface of members that require particularly low contamination such as optical members and electronic members. There is a problem in using it as a film.
  • a surface protective film using an acrylic resin for the pressure-sensitive adhesive layer is known as a surface protective film with little contamination derived from the pressure-sensitive adhesive component.
  • the surface protective film using acrylic resin for the adhesive layer is inferior in wettability, so when sticking the surface protective film manually, air bubbles are involved between the adherend and the surface protective film. There is.
  • an acrylic resin is used for the adhesive layer, there is a problem that glue residue is likely to be generated at the time of peeling, and a surface protection film for protecting the surface of a member that is particularly apt to be mixed with foreign substances such as an optical member and an electronic member. There is a problem to use as.
  • the surface protective film attached to the adherend may need to be peeled off immediately after sticking for correction of misalignment, etc. In this case, it can be peeled lightly without deformation, and then In addition, it is required to be able to re-adhere well without entrainment of bubbles. Also, in applications where re-peeling does not occur frequently after re-sticking as described above, it is necessary to have excellent adhesion reliability after elapse of time in order to avoid troubles that easily peel off.
  • a pressure-sensitive adhesive containing a polyurethane-based resin that has excellent initial reworkability when adhered to an adherend and excellent adhesion reliability after aging.
  • an adhesive sheet using such an adhesive can be provided, it is effective, for example, for use in adhesively fixing various members such as an optical member and an electronic member.
  • a surface protective film using such a pressure-sensitive adhesive can be provided, it is effective, for example, for use in protecting the surface by sticking to the surface of an optical member or an electronic member.
  • An object of the present invention is to provide a pressure-sensitive adhesive containing a polyurethane-based resin that is excellent in initial reworkability when bonded to an adherend and excellent in adhesion reliability after aging.
  • the subject of this invention is providing the adhesive sheet and surface protection film which have an adhesive layer which consists of such an adhesive.
  • the subject of this invention is providing the optical member and electronic member to which such an adhesive sheet and a surface protection film were stuck.
  • the pressure-sensitive adhesive of the present invention is A pressure-sensitive adhesive containing a polyurethane resin,
  • the initial adhesive strength A is 0.001 N / 20 mm to 2.0 N / 20 mm
  • the adhesive strength B after 1 day at 70 ° C. is 2.0 times or more of the initial adhesive strength A.
  • the polyurethane resin is a polyurethane resin obtained by curing a composition containing a polyol (A) having two or more OH groups and a polyfunctional isocyanate compound (B).
  • the polyol (A) is two or more kinds of polyols.
  • the two or more types of polyols are at least one type of polyol having two OH groups, and at least one type of polyol having three or more OH groups.
  • the polyol having two OH groups has a number average molecular weight Mn of 6000 or more, and the polyol having three or more OH groups has a number average molecular weight Mn of 2,000 or more.
  • the polyol having two OH groups has a number average molecular weight Mn of less than 6000
  • the polyol having three or more OH groups has a number average molecular weight Mn of less than 2000
  • the polyol (A) And the equivalent ratio of NCO group to OH group in the polyfunctional isocyanate compound (B) is less than 1.3 as NCO group / OH group.
  • the polyol (A) contains 50% by weight or more of a polyol having two OH groups.
  • the amount of the catalyst (C) used for obtaining the polyurethane resin by curing is 0.01 parts by weight or more with respect to 100 parts by weight of the polyol (A).
  • the pressure-sensitive adhesive sheet of the present invention has a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention on at least one side of the base material layer.
  • the optical member of the present invention has the adhesive sheet of the present invention attached thereto.
  • the electronic member of the present invention has the adhesive sheet of the present invention attached thereto.
  • the surface protective film of the present invention has a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention on one side of the base material layer.
  • the surface protective film of the present invention is used for surface protection of an optical member or an electronic member.
  • the optical member of the present invention has the surface protective film of the present invention attached thereto.
  • the electronic member of the present invention has the surface protective film of the present invention attached thereto.
  • a pressure-sensitive adhesive containing a polyurethane-based resin that is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after time.
  • the adhesive sheet and surface protection film which have an adhesive layer which consists of such an adhesive can be provided.
  • an optical member or an electronic member to which such an adhesive sheet or a surface protective film is attached can be provided.
  • the pressure-sensitive adhesive of the present invention contains a polyurethane resin as a main component.
  • the content of the polyurethane resin in the pressure-sensitive adhesive of the present invention is preferably 90% to 100% by weight, more preferably 95% to 100% by weight, and still more preferably 98% to 100% by weight. It is. Only one type of adhesive may be used, or two or more types may be used.
  • the pressure-sensitive adhesive of the present invention has an initial pressure A of 0.001 N / 20 mm to 2.0 N / 20 mm, preferably 0.005 N / mm, where A is the initial pressure after bonding to an acrylic plate. 20 mm to 1.8 N / 20 mm, more preferably 0.01 N / 20 mm to 1.5 N / 20 mm, particularly preferably 0.1 N / 20 mm to 1.3 N / 20 mm, and most preferably 0.15 N. / 20 mm to 1.0 N / 20 mm.
  • the initial adhesive strength A is within the above range, the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend. The measurement of the initial adhesive strength A will be described later.
  • the adhesive strength B after 70 ° C. ⁇ 1 day is preferably 0.1 N / 20 mm or more. More preferably, it is 0.5 N / 20 mm or more, further preferably 1.0 N / 20 mm or more, and particularly preferably 1.5 N / 20 mm or more.
  • the upper limit of the adhesive strength B after 70 ° C. ⁇ 1 day is preferably 10 N / 20 mm or less.
  • the adhesive strength B after 70 ° C. ⁇ 1 day is 2.0 times or more of the initial adhesive strength A, preferably 3.0 times or more, more preferably 4.0 times or more. It is particularly preferably 5.0 times or more, and most preferably 10 times or more.
  • the upper limit of the magnification of the adhesive strength B after 70 ° C. ⁇ 1 day to the initial adhesive strength A is preferably 100 times or less.
  • the adhesive of the present invention has an adhesive reliability after lapse of time when adhered to an adherend. Excellent in properties. The measurement of the adhesive strength B after 70 ° C. ⁇ 1 day will be described later.
  • the polyurethane-based resin is preferably obtained by curing a composition containing a polyol (A) having two or more OH groups and a polyfunctional isocyanate compound (B).
  • a polyurethane-based resin By adopting such a polyurethane-based resin, the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after aging. Moreover, by adopting such a polyurethane-based resin, the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • the polyol (A) is two or more kinds of polyols.
  • the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after aging.
  • the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • the polyol (A) is preferably two or more kinds of polyols.
  • the two or more kinds of polyols are preferably polyols having at least one kind having two OH groups, and at least one kind thereof. Is a polyol having 3 or more OH groups.
  • the polyol having two OH groups that can be contained in the polyol (A) has a number average molecular weight Mn of preferably 6000 or more, more preferably 7000 or more, further preferably 8000 or more, particularly preferably. 9000 or more.
  • the upper limit of the number average molecular weight Mn is preferably 20000 or less.
  • the pressure-sensitive adhesive of the present invention has excellent wettability, low contamination, paste residue. Reduction can be achieved at the same time.
  • the polyol having three or more OH groups that can be contained in the polyol (A) has a number average molecular weight Mn of preferably 2000 or more, more preferably 2500 or more, still more preferably 3000 or more, particularly preferably. Is 3500 or more.
  • the upper limit of the number average molecular weight Mn is preferably 20000 or less.
  • the pressure-sensitive adhesive of the present invention has excellent wettability, low contamination, and paste. It is possible to reduce waste.
  • the polyol (A) contains a polyol having two OH groups, preferably 50% by weight or more, more preferably 55% by weight or more, further preferably 60% by weight or more, and further preferably 62% by weight. It is contained more preferably, more preferably 65% by weight or more, most preferably 67% by weight or more.
  • the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after aging.
  • the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduction of glue residue.
  • polyol (A) examples include polyester polyol, polyether polyol, polycaprolactone polyol, polycarbonate polyol, and castor oil-based polyol.
  • Polyester polyol can be obtained, for example, by an esterification reaction between a polyol component and an acid component.
  • polyol component examples include ethylene glycol, diethylene glycol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-butyl-2-ethyl-1 , 3-propanediol, 2,4-diethyl-1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl -1,8-octanediol, 1,8-decanediol, octadecanediol, glycerin, trimethylolpropane, pentaerythritol, hexanetriol, polypropylene glycol and the like.
  • the acid component examples include succinic acid, methyl succinic acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, 1,12-dodecanedioic acid, 1,14-tetradecanedioic acid, dimer acid, 2-methyl-1, 4-cyclohexanedicarboxylic acid, 2-ethyl-1,4-cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, isophthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 4,4'-biphenyldicarboxylic acid , And these acid anhydrides.
  • polyether polyols examples include water, low molecular weight polyols (propylene glycol, ethylene glycol, glycerin, trimethylolpropane, pentaerythritol, etc.), bisphenols (bisphenol A, etc.), dihydroxybenzenes (catechol, resorcin, hydroquinone, etc.), etc. And polyether polyols obtained by addition polymerization of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide. Specific examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and the like.
  • polycaprolactone polyol examples include caprolactone-based polyester diols obtained by ring-opening polymerization of cyclic ester monomers such as ⁇ -caprolactone and ⁇ -valerolactone.
  • polycarbonate polyol examples include a polycarbonate polyol obtained by polycondensation reaction of the polyol component and phosgene; the polyol component, dimethyl carbonate, diethyl carbonate, diprovir carbonate, diisopropyl carbonate, dibutyl carbonate, ethyl butyl carbonate, ethylene carbonate, Polycarbonate polyol obtained by ester exchange condensation with carbonic acid diesters such as propylene carbonate, diphenyl carbonate and dibenzyl carbonate; copolymerized polycarbonate polyol obtained by using two or more of the above polyol components in combination; Polycarbonate polyol obtained by esterification reaction with a compound; the above-mentioned various polycarbonate polyols and a hydroxyl group-containing compound; Polycarbonate polyol obtained by etherification reaction; polycarbonate polyol obtained by transesterification of the various polycarbonate polyols and ester compounds; polycarbonate polyol obtained by trans
  • castor oil-based polyol examples include castor oil-based polyol obtained by reacting castor oil fatty acid with the above polyol component. Specific examples include castor oil-based polyols obtained by reacting castor oil fatty acid with polypropylene glycol.
  • polyfunctional isocyanate compound (B) Only one type of polyfunctional isocyanate compound (B) may be used, or two or more types may be used.
  • polyfunctional isocyanate compound (B) any suitable polyfunctional isocyanate compound that can be used for the urethanization reaction can be adopted.
  • examples of such a polyfunctional isocyanate compound (B) include polyfunctional aliphatic isocyanate compounds, polyfunctional alicyclic isocyanate compounds, polyfunctional aromatic isocyanate compounds, and the like.
  • polyfunctional aliphatic isocyanate compound examples include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 1,3-butylene diisocyanate, dodecamethylene diisocyanate, 2,4,4 Examples include 4-trimethylhexamethylene diisocyanate.
  • polyfunctional alicyclic isocyanate compound examples include 1,3-cyclopentene diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, Examples include hydrogenated tolylene diisocyanate and hydrogenated tetramethylxylylene diisocyanate.
  • polyfunctional aromatic diisocyanate compound examples include phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, 4 4,4'-toluidine diisocyanate, 4,4'-diphenyl ether diisocyanate, 4,4'-diphenyl diisocyanate, 1,5-naphthalene diisocyanate, xylylene diisocyanate and the like.
  • polyfunctional isocyanate compound (B) examples include trimethylolpropane adducts of various polyfunctional isocyanate compounds as described above, burettes reacted with water, and trimers having an isocyanurate ring. These may be used in combination.
  • the polyfunctional isocyanate compound (B) is preferably a polyfunctional aromatic diisocyanate compound.
  • a polyfunctional aromatic diisocyanate compound as the polyfunctional isocyanate compound (B), whitening of the resulting pressure-sensitive adhesive can be suppressed, and high transparency can be imparted. If high transparency can be imparted to the pressure-sensitive adhesive of the present invention, it becomes possible to increase the transparency of the surface protection film of the present invention having a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention. Inspection or the like can be accurately performed in a state of being attached to the surface of the member or the electronic member.
  • the polyurethane-based resin is preferably obtained by curing a composition containing a polyol (A) and a polyfunctional isocyanate compound (B).
  • a composition may contain any appropriate other component other than the polyol (A) and the polyfunctional isocyanate compound (B) as long as the effects of the present invention are not impaired.
  • Such other components include catalysts, other resin components other than polyurethane resins, tackifiers, inorganic fillers, organic fillers, metal powders, pigments, foils, softeners, plasticizers, Examples thereof include an anti-aging agent, a conductive agent, an ultraviolet absorber, an antioxidant, a light stabilizer, a surface lubricant, a leveling agent, a corrosion inhibitor, a heat stabilizer, a polymerization inhibitor, a lubricant, and a solvent.
  • the weight ratio of the polyol (A) and the polyfunctional isocyanate compound (B) is preferably 30 parts by weight or less, more preferably 28 parts by weight, based on 100 parts by weight of the polyol (A). It is not more than parts by weight, more preferably not more than 25 parts by weight, particularly preferably not more than 23 parts by weight.
  • the lower limit of the weight ratio of the polyfunctional isocyanate compound (B) is preferably 5 parts by weight or more for the polyfunctional isocyanate compound (B) with respect to 100 parts by weight of the polyol (A).
  • the pressure-sensitive adhesive of the present invention has excellent initial reworkability when adhered to an adherend, Excellent adhesion reliability later. Moreover, by adjusting the weight ratio of the polyol (A) and the polyfunctional isocyanate compound (B) within the above range, the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduction of glue residue. .
  • the equivalent ratio of NCO groups to OH groups is preferably 0.1 to 5.0, more preferably 0.2 to 0.5, as NCO groups / OH groups. 4.0, more preferably 0.3 to 3.0.
  • the equivalent ratio of NCO group / OH group within the above range, the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend, and in adhesive reliability after aging. Excellent.
  • the equivalent ratio of NCO group / OH group within the above range the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • an NCO group The equivalent ratio of OH groups to NOH groups / OH groups is preferably less than 1.3, more preferably 0.1 to 1.2, still more preferably 0.1 to 1.1, Particularly preferred is 0.1 to 1.0.
  • the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after aging.
  • the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • the effects of the present invention such as a urethanization reaction method using bulk polymerization or solution polymerization, are used. Any appropriate method can be adopted as long as it is not impaired.
  • a catalyst (C) is preferably used.
  • a catalyst (C) include organometallic compounds and tertiary amine compounds.
  • organometallic compounds examples include iron compounds, tin compounds, titanium compounds, zirconium compounds, lead compounds, cobalt compounds, zinc compounds, and the like.
  • an iron-based compound is preferable in terms of high reactivity.
  • iron-based compounds include iron acetylacetonate and iron 2-ethylhexanoate.
  • tin compounds include dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin maleate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin sulfide, tributyltin methoxide, tributyltin acetate, triethyltin ethoxide, Examples include tributyltin ethoxide, dioctyltin oxide, dioctyltin dilaurate, tributyltin chloride, tributyltin trichloroacetate, and tin 2-ethylhexanoate.
  • titanium compounds examples include dibutyltitanium dichloride, tetrabutyltitanate, butoxytitanium trichloride, and the like.
  • zirconium compounds include zirconium naphthenate and zirconium acetylacetonate.
  • Examples of the lead compound include lead oleate, lead 2-ethylhexanoate, lead benzoate, lead naphthenate and the like.
  • cobalt compounds examples include cobalt 2-ethylhexanoate and cobalt benzoate.
  • Examples of the zinc-based compound include zinc naphthenate and zinc 2-ethylhexanoate.
  • tertiary amine compound examples include triethylamine, triethylenediamine, 1,8-diazabixic mouth- (5,4,0) -undecene-7, and the like.
  • the catalyst (C) may be only one type or two or more types.
  • the amount of the catalyst (C) used is preferably 0.01 parts by weight or more, more preferably 0.08 parts by weight or more, and further preferably 0.1 parts by weight with respect to 100 parts by weight of the polyol (A). Part or more, particularly preferably 0.15 part by weight or more.
  • the upper limit of the amount of catalyst (C) used is preferably 5 parts by weight or less.
  • the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • the polyol (A) when a polyol having two OH groups having a number average molecular weight Mn of less than 6000 and a polyol having three or more OH groups having a number average molecular weight Mn of less than 2,000 are used in combination,
  • the amount of the catalyst (C) used within the above range the pressure-sensitive adhesive of the present invention is excellent in initial reworkability when adhered to an adherend and excellent in adhesion reliability after aging. .
  • the pressure-sensitive adhesive of the present invention can achieve both excellent wettability, low contamination, and reduced glue residue.
  • the pressure-sensitive adhesive of the present invention may contain any appropriate other component in addition to the polyurethane resin as described above as long as the effects of the present invention are not impaired.
  • other components include other resin components other than polyurethane resins, tackifiers, inorganic fillers, organic fillers, metal powders, pigments, foils, softeners, plasticizers, and anti-aging agents.
  • the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention can be formed by any appropriate method.
  • a pressure-sensitive adhesive layer can be obtained by applying a pressure-sensitive adhesive material on any suitable support to form a pressure-sensitive adhesive.
  • the member that becomes the base layer of the surface protective film may be used as a support, and the pressure-sensitive adhesive formed by forming on any other appropriate support is finally used as the surface protective film. It is good also as an adhesive layer by transferring on the member used as a base material layer.
  • Examples of the method for applying the adhesive material include roll coating, gravure coating, reverse coating, roll brushing, spray coating, air knife coating, extrusion coating using a die coater, and the like.
  • the pressure-sensitive adhesive sheet of the present invention has a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention on at least one surface of the base material layer.
  • the surface protective film of this invention has the adhesive layer which consists of an adhesive of this invention in the single side
  • the pressure-sensitive adhesive sheet of the present invention is preferably used, for example, for applications in which various members such as optical members and electronic members are adhesively fixed.
  • the surface protective film of the present invention is preferably used for, for example, an application of protecting the surface by sticking to the surface of an optical member or an electronic member.
  • the thickness of the pressure-sensitive adhesive layer any appropriate thickness can be adopted depending on the application.
  • the thickness of the pressure-sensitive adhesive layer is preferably 1 ⁇ m to 100 ⁇ m, more preferably 3 ⁇ m to 50 ⁇ m, and still more preferably 5 ⁇ m to 30 ⁇ m.
  • FIG. 1 is a schematic cross-sectional view of an adhesive sheet or a surface protective film according to a preferred embodiment of the present invention.
  • the pressure-sensitive adhesive sheet or surface protective film 10 includes a base material layer 1 and a pressure-sensitive adhesive layer 2.
  • the pressure-sensitive adhesive sheet or the surface protective film of the present invention may further have any appropriate other layer as necessary (not shown).
  • the pressure-sensitive adhesive sheet of the present invention may have a pressure-sensitive adhesive layer made of the pressure-sensitive adhesive of the present invention on both surfaces of the base material layer. That is, in FIG. 1, a pressure-sensitive adhesive layer may be further provided on the side opposite to the pressure-sensitive adhesive layer 2 of the base material layer 1.
  • a fatty acid is added to the base material layer for the purpose of forming a wound body that can be easily rewound.
  • Perform release treatment by adding amide, polyethyleneimine, long-chain alkyl additives, etc., or provide a coat layer made of any appropriate release agent such as silicone-based, long-chain alkyl-based, fluorine-based, etc. Can do.
  • the pressure-sensitive adhesive sheet and the surface protective film of the present invention may be bonded with a release liner having releasability.
  • the thickness of the pressure-sensitive adhesive sheet and the surface protective film of the present invention can be set to any appropriate thickness depending on the application. From the viewpoint of fully expressing the effects of the present invention, the thickness is preferably 10 ⁇ m to 300 ⁇ m, more preferably 15 ⁇ m to 250 ⁇ m, still more preferably 20 ⁇ m to 200 ⁇ m, and particularly preferably 25 ⁇ m to 150 ⁇ m.
  • the pressure-sensitive adhesive sheet and surface protective film of the present invention preferably have high transparency. Due to the high transparency of the pressure-sensitive adhesive sheet and the surface protective film of the present invention, it is possible to accurately inspect the surface of the optical member or the electronic member while it is adhered.
  • the haze is preferably 5% or less, more preferably 4% or less, still more preferably 3% or less, and particularly preferably 2% or less. Preferably it is 1% or less.
  • the thickness of the base material layer any appropriate thickness can be adopted depending on the application.
  • the thickness of the base material layer is preferably 5 ⁇ m to 300 ⁇ m, more preferably 10 ⁇ m to 250 ⁇ m, still more preferably 15 ⁇ m to 200 ⁇ m, and particularly preferably 20 ⁇ m to 150 ⁇ m.
  • the substrate layer may be a single layer or a laminate of two or more layers.
  • the base material layer may be stretched.
  • the material of the base material layer any appropriate material can be adopted depending on the application.
  • a plastic, paper, a metal film, a nonwoven fabric, etc. are mentioned.
  • it is a plastic.
  • the base material layer may be composed of one kind of material, or may be composed of two or more kinds of materials. For example, you may be comprised from 2 or more types of plastics.
  • plastic examples include polyester resins, polyamide resins, and polyolefin resins.
  • polyester resin examples include polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate.
  • polyolefin resin examples include olefin monomer homopolymers, olefin monomer copolymers, and the like. Specific examples of polyolefin resins include homopolypropylene; block-type, random-type, and graft-type propylene copolymers having an ethylene component as a copolymer component; reactor TPO; low density, high density, linear Low density, ultra-low density, etc.
  • ethylene polymers ethylene / propylene copolymer, ethylene / vinyl acetate copolymer, ethylene / methyl acrylate copolymer, ethylene / ethyl acrylate copolymer, ethylene / acrylic acid And ethylene copolymers such as butyl copolymer, ethylene / methacrylic acid copolymer, and ethylene / methyl methacrylate copolymer.
  • the base material layer may contain any appropriate additive as required.
  • the additive that can be contained in the base material layer include an antioxidant, an ultraviolet absorber, a light stabilizer, an antistatic agent, a filler, and a pigment.
  • the kind, number, and amount of additives that can be contained in the base material layer can be appropriately set according to the purpose.
  • the material of the base material layer is plastic, it is preferable to contain some of the above additives for the purpose of preventing deterioration.
  • particularly preferred additives include antioxidants, ultraviolet absorbers, light stabilizers, and fillers.
  • any appropriate antioxidant can be adopted as the antioxidant.
  • antioxidants include phenol-based antioxidants, phosphorus-based processing heat stabilizers, lactone-based processing heat stabilizers, sulfur-based heat-resistant stabilizers, phenol-phosphorus-based antioxidants, and the like.
  • the content of the antioxidant is preferably 1 part by weight or less with respect to 100 parts by weight of the base resin of the base layer (when the base layer is a blend, the blend is the base resin), The amount is more preferably 0.5 parts by weight or less, and still more preferably 0.01 parts by weight to 0.2 parts by weight.
  • any appropriate UV absorber can be adopted as the UV absorber.
  • UV absorbers include benzotriazole UV absorbers, triazine UV absorbers, and benzophenone UV absorbers.
  • the content of the ultraviolet absorber is preferably 2 parts by weight or less with respect to 100 parts by weight of the base resin forming the base layer (when the base layer is a blend, the blend is the base resin). More preferably 1 part by weight or less, still more preferably 0.01 part by weight to 0.5 part by weight.
  • any appropriate light stabilizer can be adopted as the light stabilizer.
  • Examples of such light stabilizers include hindered amine light stabilizers and benzoate light stabilizers.
  • the content ratio of the light stabilizer is preferably 2 parts by weight or less with respect to 100 parts by weight of the base resin forming the base layer (in the case where the base layer is a blend, the blend is the base resin). More preferably 1 part by weight or less, still more preferably 0.01 part by weight to 0.5 part by weight.
  • any suitable filler can be adopted as the filler.
  • suitable fillers include inorganic fillers.
  • Specific examples of the inorganic filler include carbon black, titanium oxide, and zinc oxide.
  • the content of the filler is preferably 20 parts by weight or less with respect to 100 parts by weight of the base resin forming the base layer (when the base layer is a blend, the blend is the base resin). More preferably, it is 10 parts by weight or less, and further preferably 0.01 to 10 parts by weight.
  • inorganic, low molecular weight and high molecular weight antistatic agents such as surfactants, inorganic salts, polyhydric alcohols, metal compounds, carbon and the like are also preferred.
  • a high molecular weight antistatic agent and carbon are preferable from the viewpoint of contamination and adhesiveness maintenance.
  • the pressure-sensitive adhesive sheet and the surface protective film of the present invention can be used for any appropriate application.
  • the pressure-sensitive adhesive sheet of the present invention is preferably used, for example, for applications in which various members such as optical members and electronic members are adhesively fixed.
  • the surface protective film of the present invention is preferably used for, for example, an application of protecting the surface by sticking to the surface of an optical member or an electronic member.
  • the optical member to which the pressure-sensitive adhesive sheet of the present invention is attached can be manually bonded and peeled many times.
  • the electronic member to which the pressure-sensitive adhesive sheet of the present invention is attached can be bonded and peeled many times manually.
  • optical member to which the surface protective film of the present invention is attached can be bonded and peeled many times manually.
  • the electronic member to which the surface protective film of the present invention is attached can be bonded and peeled many times manually.
  • the pressure-sensitive adhesive sheet and the surface protective film of the present invention can be produced by any appropriate method.
  • a manufacturing method for example, (1) A method of applying a solution or a hot melt of a pressure-sensitive adhesive layer forming material (for example, a composition containing a polyurethane resin) on a base material layer, (2) A method of transferring the pressure-sensitive adhesive layer applied and formed in the form of a separator onto the base material layer according to that, (3) A method of forming and applying the forming material of the pressure-sensitive adhesive layer onto the base material layer, (4) A method of extruding a base material layer and an adhesive layer in two layers or multiple layers, (5) A method of laminating a pressure-sensitive adhesive layer on a base material layer, or a method of laminating two pressure-sensitive adhesive layers together with a laminate layer, (6) A method of laminating a pressure-sensitive adhesive layer and a base material layer forming material such as a film or a laminate layer in two or multiple layers, It can be performed according to any appropriate production
  • test and evaluation method in an Example etc. are as follows. Note that “parts” means “parts by weight” unless otherwise noted, and “%” means “% by weight” unless otherwise noted.
  • the adhesive sheet or the surface protective film was cut into a width of 20 mm and a length of 100 mm to obtain a sample for evaluation.
  • the pressure-sensitive adhesive layer surface of the sample for evaluation was attached to an acrylic plate (manufactured by Mitsubishi Rayon Co., Ltd., trade name: Acrylite L) by one reciprocating 2.0 kg roller. After curing for 30 minutes in an atmosphere at a temperature of 23 ° C.
  • peeling is performed at a peeling angle of 180 ° and a pulling speed of 300 mm / min using a universal tensile testing machine (product name: TCM-1kNB, manufactured by Minebea Co., Ltd.). The adhesive strength was measured.
  • the adhesive sheet or the surface protective film was cut into a width of 20 mm and a length of 100 mm to obtain a sample for evaluation.
  • the pressure-sensitive adhesive layer surface of the sample for evaluation was attached to an acrylic plate (manufactured by Mitsubishi Rayon, trade name: Acrylite) by one reciprocation of a 2 kg roller. After curing for 30 minutes in an atmosphere at a temperature of 23 ° C.
  • the end of the sample for evaluation is pinched by the evaluator's hand, the peel angle is 100 to 120 ° in the direction of 100 mm in length, and the pulling speed is 100 mm / min. Peeling was performed at ⁇ 500 mm / min, and deformation of the substrate was observed. Reworkability was evaluated according to the following criteria. ⁇ : The substrate was not deformed and could be peeled off. X: The substrate was deformed.
  • the pressure-sensitive adhesive sheet or surface protective film was cut into a width of 20 mm and a length of 50 mm to obtain a sample for evaluation.
  • an evaluation sample was applied to an acrylic plate (product name: Acrylite L, manufactured by Mitsubishi Rayon Co., Ltd.) obtained by cutting the adhesive layer surface of the evaluation sample into a width of 25 mm and a length of 200 mm.
  • the 2 kg roller was attached by one reciprocation. After storage at 70 ° C. for 1 day, the sample is left for 30 minutes in an atmosphere at a temperature of 23 ° C.
  • the length is such that the evaluation sample exists inside the curved acrylic plate with the evaluation sample attached. It attached to the jig
  • the surface protective film was cut into 2.5 cm ⁇ 10.0 cm to obtain a test piece.
  • the test piece was bonded to an acrylic plate (trade name: Acrylite L, manufactured by Mitsubishi Rayon Co., Ltd.) at a speed of 10 m / min, and the presence or absence of bubbles between the test piece and the acrylic plate was confirmed. Evaluation was performed according to the following criteria. ⁇ : No bubbles. (Triangle
  • a urethane-based pressure-sensitive adhesive composition was applied to a base material “Lumirror S10” (thickness 38 ⁇ m, manufactured by Toray Industries, Inc.) made of a polyester resin so that the thickness after drying with a fountain roll was 10 ⁇ m. It was cured and dried under the condition of a drying time of 30 seconds. Next, the surface of the pressure-sensitive adhesive layer is covered with a release film surface-treated with a release agent, left at a temperature of 50 ° C. for 12 hours, and then left at room temperature (25 ° C.) for 1 hour to obtain a surface protective film (1). It was. In addition, the obtained surface protection film (1) can be used also as an adhesive sheet. The evaluation results are shown in Table 1.
  • a surface protective film (3) having a pressure-sensitive adhesive layer was obtained in the same manner as in Example 1 except that the part was used. In addition, the obtained surface protection film (3) can be used also as an adhesive sheet. The evaluation results are shown in Table 1.
  • a surface protective film (4) having a pressure-sensitive adhesive layer was obtained in the same manner as in Example 1 except that the part was used. In addition, the obtained surface protection film (4) can be used also as an adhesive sheet. The evaluation results are shown in Table 1.
  • a surface protective film (5) having a pressure-sensitive adhesive layer was obtained in the same manner as in Example 1 except that the part was made a part. In addition, the obtained surface protection film (5) can be used also as an adhesive sheet. The evaluation results are shown in Table 1.
  • a surface protective film (6) having a pressure-sensitive adhesive layer was obtained in the same manner as in Example 1 except that the part was made a part. In addition, the obtained surface protection film (6) can be used also as an adhesive sheet. The evaluation results are shown in Table 1.
  • Example 7 The surface protective film (1) obtained in Example 1 was attached to a polarizing plate (manufactured by Nitto Denko Corporation, trade name “TEG1465DUHC”) which is an optical member, and the optical member to which the surface protective film was attached was attached. Obtained.
  • Example 8 The surface protective film (1) obtained in Example 1 was attached to a conductive film (Nitto Denko Corporation, trade name “Electrista V270L-TFMP”) as an electronic member, and the surface protective film was attached. An electronic member was obtained.
  • a conductive film Nito Denko Corporation, trade name “Electrista V270L-TFMP”
  • the pressure-sensitive adhesive sheet and surface protective film of the present invention can be used for applications such as sticking to the surface of an optical member or electronic member to protect the surface.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Polarising Elements (AREA)
  • Laminated Bodies (AREA)
PCT/JP2013/069431 2012-07-31 2013-07-17 粘着剤 WO2014021107A1 (ja)

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JP2017179239A (ja) * 2016-03-31 2017-10-05 リンテック株式会社 表示画面用粘着シート、積層体、表示体及び画面保護方法

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TWI600735B (zh) 2017-10-01
JP2014028878A (ja) 2014-02-13
CN104508068B (zh) 2017-05-24
TW201412919A (zh) 2014-04-01
KR20150039714A (ko) 2015-04-13

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