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WO2016039289A1 - Composition - Google Patents

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Publication number
WO2016039289A1
WO2016039289A1 PCT/JP2015/075321 JP2015075321W WO2016039289A1 WO 2016039289 A1 WO2016039289 A1 WO 2016039289A1 JP 2015075321 W JP2015075321 W JP 2015075321W WO 2016039289 A1 WO2016039289 A1 WO 2016039289A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
acryloyl group
composition
compound
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2015/075321
Other languages
English (en)
Japanese (ja)
Inventor
泰則 石田
啓之 栗村
佑基 比舎
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denka Co Ltd
Original Assignee
Denki Kagaku Kogyo KK
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.)
Filing date
Publication date
Application filed by Denki Kagaku Kogyo KK filed Critical Denki Kagaku Kogyo KK
Priority to JP2016547429A priority Critical patent/JP6767869B2/ja
Publication of WO2016039289A1 publication Critical patent/WO2016039289A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G—PHYSICS
    • G06—COMPUTING OR CALCULATING; COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means

Definitions

  • the present invention relates to a composition.
  • the capacitive touch panel has a structure in which a transparent electrode is formed on a transparent substrate, and the transparent substrate is bonded to the transparent electrode.
  • an adhesive is used for bonding a decorative plate and a touch panel, bonding an icon sheet and a touch panel, and bonding a transparent substrate and a transparent substrate.
  • These icon sheets and touch panels cover the shading frame by printing, etc. in order to hide the display element drive IC, wiring, and LCD frame sealant so that only the display area is visible and to improve design. There is.
  • this light-shielding frame is present, the photocurable adhesive composition under the light-shielding frame is shielded from light by the light-shielding frame, and is not cured without being exposed to light, resulting in insufficient adhesion.
  • thermosetting property In order to solve the problem of inadequate adhesion due to uncured, a method of adjusting the light irradiation angle by irradiating light obliquely or from the side, or adding a thermosetting catalyst to the photocurable adhesive composition. In addition to photocuring property, a method of imparting thermosetting property and curing with light and heat has been practiced.
  • thermosetting to a photocurable adhesive composition and curing with light and heat requires heating a display panel such as an LCD, an EL display, and an LED display to 60 to 80 ° C. for 30 to 60 minutes. For this reason, there has been a problem of quality deterioration and shortening of product life.
  • Patent Document 1 discloses (A) a (meth) acrylate oligomer having a polyisoprene, polybutadiene, or polyurethane as a skeleton, (B) a plasticizer, and (C1) phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, 2 (Meth) acrylate selected from hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, nonylphenol EO adduct (meth) acrylate, methoxytriethylene glycol (meth) acrylate and tetrahydrofurfuryl (meth) acrylate
  • a photocurable resin composition containing a monomer is described.
  • Patent Document 2 describes a cured resin containing urethane (meth) acrylate, polybutadiene (meth) acrylate, and isoprene (meth) acrylate as components.
  • Patent Document 3 is a highly elastic resin based on a rigid skeleton monomer such as isobornyl (meth) acrylate.
  • the degree to which the adherend can be deformed in a heated atmosphere assuming the usage environment It is desirable to have the flexibility.
  • Patent Document 4 contains at least one oligomer selected from the group consisting of a polyisoprene (meth) acrylate oligomer, a polybutadiene (meth) acrylate oligomer, and a polyurethane (meth) acrylate oligomer, and a hindered amine.
  • oligomer selected from the group consisting of a polyisoprene (meth) acrylate oligomer, a polybutadiene (meth) acrylate oligomer, and a polyurethane (meth) acrylate oligomer, and a hindered amine.
  • Patent Document 5 discloses a liquid resin composition having photocurability containing (A) a compound having a (meth) acryloyl group, (B) a photopolymerization initiator, (C) a plasticizer, and (D) an antioxidant.
  • a liquid resin composition having photocurability is described in which the component (D) includes a compound (D1) having a hindered phenol structure in the molecule.
  • Patent Document 6 describes (a) at least one monomer selected from the group consisting of (meth) acrylic acid, (meth) acrylate, and (meth) acrylamide, (b) an antioxidant, and (c) initiation of photopolymerization.
  • a photocurable adhesive composition comprising an agent, (d) an oligomer having no (meth) acryloxy group, and optionally an oligomer having (e) (meth) acryloxy group is described.
  • Patent Document 7 describes (A) (a-1) a monofunctional (meth) acrylate having a hydrocarbon group having 6 to 20 carbon atoms, (a-2) a monofunctional (meth) acrylate containing a hydroxyl group, (a-3) A monofunctional (meth) acrylate containing a monofunctional (meth) acrylate having a carboxyl group or a phosphate ester group, (B) an oligomer having two or more (meth) acryloyl groups in the molecule, (C) a diene type An energy ray-curable resin composition containing a core / shell type graft copolymer and (D) a photoradical polymerization initiator is described.
  • Patent Document 8 (A) a hydrogenated 1,2-polybutadiene polyol or a hydrogenated polyisoprene polyol is reacted with a polyfunctional isocyanate compound to leave a residual hydroxyl group or isocyanate group, a (meth) acryloyl group, an isocyanate group, or (Meth) acryloyl group-containing hydrogenated 1,2-polybutadiene compound or (meth) acryloyl group-containing hydrogenated polyisoprene compound 25 to 45 having a weight average molecular weight of 50,000 to 200,000 obtained by reacting a compound having a hydroxyl group % By weight, (B) 8 to 20% by weight of (meth) acrylic acid ester having a hydroxyl group, (C) 20 to 61.8% by weight of polymerizable monomer other than (meth) acrylic acid ester having a hydroxyl group, (D) 0.2-5% by mass of a photopolymerization initiator, and (E)
  • the main chain skeleton is at least one selected from the group consisting of polybutadiene, polyisoprene, and hydrogenated products thereof, and at least one at the terminal or side chain of the main chain skeleton.
  • (Meth) acrylate having a (meth) acryloyl group and having a molecular weight of 500 to 5000 (B) a monofunctional (meth) acrylate having an unsaturated hydrocarbon group having 2 to 8 carbon atoms via an ester bond, (C) hydroxyl group-containing (meth) acrylate, (D) polyfunctional (meth) acrylate, (E) photopolymerization initiator, and (F) antioxidant, an energy ray-curable resin composition Is described.
  • Patent Document 1 describes (UA) “UA-1”, “TE2000”, “UC-102”, etc., manufactured by Light Chemical Co., Ltd. as (meth) acrylate oligomers having polyisoprene, polybutadiene, or polyurethane as a skeleton.
  • neither is (A) a (meth) acrylate oligomer having a hydrogenated conjugated diene structure.
  • Patent Document 1 does not describe (A) (meth) acrylate having a hydrogenated conjugated diene structure, coloring and discoloration after the heat resistance test cannot be suppressed. Therefore, the photocurable resin composition described in Patent Document 1 may have problems such as coloring and discoloration after the heat resistance test. That is, since such a resin composition has flexibility enough to follow the deformation of the adherend in a heated atmosphere assuming the use environment, it can be colored, discolored after the heat test, and strength after the moisture test. There is a problem of reduction.
  • Patent Document 2 does not describe a composition containing (A) a (meth) acrylate having a hydrogenated conjugated diene structure. Therefore, when trying to suppress this deformation by the method of Patent Document 2, there are problems that the adhesive surface is peeled off, the LCD is cracked, or the LCD becomes uneven in display. In recent years, the glass of display bodies such as LCDs has become thinner. When the glass becomes thinner, the LCD is easily deformed by external stress.
  • Patent Document 3 is a highly elastic resin based on a rigid skeleton monomer such as isobornyl (meth) acrylate, it cannot withstand the expansion and contraction of the adherend in the high-temperature reliability test, and is peeled off. There was a possibility of producing.
  • the present invention has a design that can withstand the expansion and contraction of the adherend in a high-temperature reliability test without using a rigid skeleton monomer such as isobornyl (meth) acrylate.
  • Patent Document 4 does not describe a composition containing (A) a (meth) acrylate having a hydrogenated conjugated diene structure.
  • Patent Document 5 describes (UC) “UC-102” or the like as a compound having (A) (meth) acryloyl group, and (A) (meth) acrylate oligomer having a hydrogenated conjugated diene structure. is not. That is, Patent Document 5 does not describe (A) (meth) acrylate having a hydrogenated conjugated diene structure.
  • Patent Document 6 describes (UC) “UC-102”, “UC-203”, etc. as (e) an oligomer having a (meth) acryloxy group, all of which have (A) a hydrogenated conjugated diene structure.
  • Patent Document 6 does not describe (A) (meth) acrylate having a hydrogenated conjugated diene structure. Therefore, in any case, when pasting a decorative board or icon sheet used for a display body such as a touch panel, when pasting a transparent substrate and a transparent substrate, when pasting a display body and an optical functional material, There existed the subject that the adhesive surface peeled off, the glass of a display body cracked, the subject of discoloration after a heat test or a moisture resistance test, and a strength fall.
  • the present invention when pasting a decorative board or icon sheet used for a display body such as a touch panel, or when pasting a transparent substrate and a transparent substrate, the present invention includes a display body and an optical functional material.
  • a curable resin composition that solves the problems of peeling of the adhesive surface and breaking of the glass of the display body, discoloration after the heat resistance test and after the moisture resistance test, and strength reduction when bonding.
  • the present inventors have realized that the composition described in the above patent document cannot solve the problems such as coloring and discoloration after the heat resistance test. In order to solve this problem, the present inventors have intensively studied. As a result, a composition containing a (meth) acrylate having a hydrogenated conjugated diene structure and a specific type of plasticizer does not cause the above problem.
  • the plasticizer is selected from the group consisting of a monoester compound having no (meth) acryloyl group, a polyester compound having no (meth) acryloyl group, and a hydrogenated conjugated diene compound having no (meth) acryloyl group.
  • problems such as coloring and discoloration after the heat resistance test do not occur as in Examples described later. Based on this discovery, the present invention has been completed.
  • one aspect of the present invention is a composition containing the following (A) to (E): (A) (meth) acrylate having hydrogenated conjugated diene structure (B) monofunctional (meth) acrylate (C) radical photopolymerization initiator (D) plasticizer (E) antioxidant (D) plasticizer is ( A monoester compound not having a (meth) acryloyl group, a polyester compound not having a (meth) acryloyl group, a monoether compound having no (meth) acryloyl group, a polyether compound not having a (meth) acryloyl group, It is at least one selected from the group consisting of a monocarbonate compound having no (meth) acryloyl group, a polycarbonate compound having no (meth) acryloyl group, and a hydrogenated conjugated diene compound having no (meth) acryloyl group. It is a composition.
  • (A) the (meth) acrylate having a hydrogenated conjugated diene structure is preferably a polyfunctional (meth) acrylate. Moreover, it is preferable that (A) (meth) acrylate which has a hydrogenated conjugated diene structure is this composition which is urethane (meth) acrylate. In the above composition, the (A) (meth) acrylate having a hydrogenated conjugated diene structure preferably has a molecular weight of 500 to 50,000. In the above composition, it is preferable that the photopolymerization initiator (C) is at least one selected from the group consisting of benzoin derivatives, acylphosphine oxide derivatives, and ⁇ -hydroxyketone derivatives. .
  • the (D) plasticizer is preferably a polyester compound having no (meth) acryloyl group and having an alkyl group having 8 to 22 carbon atoms.
  • the total amount of (A), (B) and (D) is 100 parts by mass
  • the amount of component (A) used is 5 to 70 parts by mass
  • the amount of component (B) used is 1 to 50 parts by mass
  • the amount of component (D) used is preferably 1 to 80 parts by mass.
  • the amount of the component (C) used is 0.001 to 10 parts by mass with respect to the total of 100 parts by mass of (A), (B) and (D)
  • the component (E) is used.
  • the amount is preferably 0.001 to 5 parts by mass.
  • Another embodiment of the present invention is a photocurable resin composition comprising the above composition.
  • Another embodiment of the present invention is an adhesive composition comprising the above composition.
  • Another embodiment of the present invention is a coating composition comprising the above composition.
  • Another embodiment of the present invention is a cured product of the above composition.
  • Another embodiment of the present invention is a composite in which an adherend is coated or bonded with the cured body.
  • the adherend is preferably at least one selected from the group consisting of triacetylcellulose, fluorine-based polymer, polyester, polycarbonate, polyolefin, glass, and metal.
  • at least one of the adherends preferably includes a portion having a light transmittance of 0.1 or less.
  • Another embodiment of the present invention is a touch panel laminate in which an adherend is bonded using the above-described adhesive composition.
  • Another aspect of the present invention is a liquid crystal panel laminate in which an adherend is bonded with the above-described adhesive composition.
  • Another embodiment of the present invention is a display using the touch panel laminate.
  • Another embodiment of the present invention is a display using the above liquid crystal panel laminate.
  • the present invention can provide, for example, a composition having high deep-part curability and high heat-resistant yellowing.
  • the present invention can be applied, for example, when a decorative board or icon sheet used for a display body such as a touch panel is bonded, when a transparent substrate and a transparent substrate are bonded, or when a printed part is bonded.
  • a curable resin composition can be provided in which a portion that is not exposed to visible light or ultraviolet rays from the front side by a light-shielding frame such as printing is cured from the front side by visible light or ultraviolet rays from the side surface.
  • the hardening of the curable resin composition under a light-shielding frame is possible, for example, and it has the effect of suppressing the hardening defect of an adhesive composition.
  • the (meth) acrylate having a hydrogenated conjugated diene structure refers to a (meth) acrylate having a hydrogenated conjugated diene skeleton in the molecule.
  • the hydrogenated conjugated diene refers to, for example, a compound obtained by hydrogenating a conjugated diene.
  • the hydrogenated conjugated diene is preferably at least one selected from the group consisting of hydrogenated polybutadiene, hydrogenated polyisoprene and the like.
  • (A) As (meth) acrylate which has a hydrogenated conjugated diene structure the polyfunctional (meth) acrylate which has a 2 or more (meth) acryloyl group in the terminal or side chain in a molecule
  • numerator is preferable.
  • the polyfunctional (meth) acrylate refers to a compound having two or more (meth) acryloyl groups.
  • the (meth) acrylate having a hydrogenated conjugated diene structure preferably does not have a conjugated diene structure (a conjugated diene structure in which a double bond is separated by one single bond).
  • an oligomer is preferable.
  • urethane (meth) acrylate As the (meth) acrylate having a hydrogenated conjugated diene structure, urethane (meth) acrylate is preferable.
  • Urethane (meth) acrylates include hydrogenated 1,2-polybutadiene terminal urethane (meth) acrylate (for example, “TEAI-1000” manufactured by Nippon Soda Co., Ltd.), hydrogenated 1,2-polybutadiene terminal urethane (meth) acrylate. (For example, “KRM8792”, “KRM8776” manufactured by Daicel Ornex Co., Ltd.) and the like.
  • the urethane (meth) acrylate is a reaction between a polyol compound (hereinafter represented by X), an organic polyisocyanate compound (hereinafter represented by Y), and a hydroxy (meth) acrylate (hereinafter represented by Z) (for example, , A urethane (meth) acrylate having a urethane bond in the molecule, obtained by a polycondensation reaction).
  • polyol compound (X) examples include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, 1,4-butanediol, polybutylene glycol, 1, 5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 2,2-butylethyl-1,3-propanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, trimethylolethane, trimethylolpropane, poly At least polyhydric alcohols such as limethylolpropane, pen
  • a hydrogenated conjugated diene polyol is preferable because it has a hydrogenated conjugated diene structure.
  • the hydrogenated conjugated diene polyol one or more selected from the group consisting of hydrogenated polybutadiene polyol and hydrogenated polyisoprene polyol is more preferable, and hydrogenated polybutadiene polyol (hydrogenated polybutadiene polyol) is most preferable.
  • hydrogenated polybutadiene polyols hydrogenated 1,2-polybutadiene polyols are preferred.
  • the organic polyisocyanate compound (Y) is not particularly limited, but for example, aromatic, aliphatic, cycloaliphatic, and alicyclic polyisocyanates can be used. Among them, tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), hydrogenated diphenylmethane diisocyanate (H-MDI), polyphenylmethane polyisocyanate (crude MDI), modified diphenylmethane diisocyanate (modified MDI), hydrogenated xylylene diisocyanate.
  • TDI tolylene diisocyanate
  • MDI diphenylmethane diisocyanate
  • H-MDI hydrogenated diphenylmethane diisocyanate
  • CAde MDI polyphenylmethane polyisocyanate
  • modified MDI modified diphenylmethane diisocyanate
  • hydrogenated xylylene diisocyanate hydrogenated xy
  • H-XDI xylylene diisocyanate
  • XDI xylylene diisocyanate
  • HMDI hexamethylene diisocyanate
  • TXDI trimethylhexamethylene diisocyanate
  • m-TMXDI tetramethylxylylene diisocyanate
  • IPDI isophorone diisocyanate
  • NBDI norbornene diisocyanate
  • Polyisocyanates such as 1,3-bis (isocyanatomethyl) cyclohexane (H6XDI), etc. Trimer compounds of polyisocyanates, reaction products of these polyisocyanates with polyols are preferably used.
  • At least one selected from the group consisting of tolylene diisocyanate (TDI), hydrogenated xylylene diisocyanate (H-XDI), and isophorone diisocyanate (IPDI) is preferable.
  • IPDI isophorone diisocyanate
  • isophorone diisocyanate is more preferable, and isophorone diisocyanate (IPDI) is most preferable.
  • Hydroxy (meth) acrylate (Z) refers to (meth) acrylate having a hydroxyl group.
  • examples of the hydroxy (meth) acrylate (Z) include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, hydroxyalkyl (meth) acrylate such as 2-hydroxybutyl (meth) acrylate, 2- Hydroxyethyl (meth) acryloyl phosphate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycerin di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, caprolactone Modified 2-hydroxyethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone modified 2-hydroxyethy
  • hydroxyalkyl (meth) acrylate is preferred.
  • hydroxyalkyl (meth) acrylates one or more selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl (meth) acrylate are preferable. Hydroxyethyl (meth) acrylate is more preferred.
  • the average molecular weight of the (meth) acrylate having a hydrogenated conjugated diene structure is preferably from 500 to 50,000, more preferably from 1,000 to 40,000 in terms of viscosity adjustment.
  • Examples of the average molecular weight include weight average molecular weight and number average molecular weight. In the case of a weight average molecular weight, it is preferably 10,000 to 50,000, more preferably 15,000 to 40,000. In the case of the number average molecular weight, 500 to 5000 is preferable, and 1000 to 4000 is more preferable.
  • the average molecular weight is obtained by preparing a calibration curve with commercially available standard polystyrene using GPC system (SC-8010 manufactured by Tosoh Corporation) using tetrahydrofuran as a solvent under the following conditions.
  • the amount of the (meth) acrylate oligomer having a hydrogenated conjugated diene structure is preferably 5 to 70 parts by mass, and preferably 15 to 60 parts by mass, out of a total of 100 parts by mass of (A), (B) and (D). Part is more preferable, and 30 to 50 parts by mass is most preferable. If it is 5 mass parts or more, favorable sclerosis
  • Monofunctional (meth) acrylate refers to (meth) acrylate having one (meth) acryloyl group.
  • Monofunctional (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, isooctyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (Meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, methoxylated cyclodecatriene (meth) acrylate, 2-hydroxyethyl (
  • One or more of these can be used.
  • at least one selected from the group consisting of 2-hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, n-octyl (meth) acrylate, and lauryl (meth) acrylate is preferable.
  • N-octyl (meth) acrylate is most preferred.
  • n-octyl (meth) acrylate 1 to 95 parts by mass of n-octyl (meth) acrylate is preferably contained in 100 parts by mass of monofunctional (meth) acrylate, more preferably 20 to 90 parts by mass, and 40 to 70 parts by mass. It is most preferable to contain.
  • Monofunctional (meth) acrylate used in combination with n-octyl (meth) acrylate includes 2-hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, and lauryl (meth) acrylate One or more selected from the group is preferred, and 2-hydroxybutyl (meth) acrylate is more preferred.
  • the amount of the monofunctional (meth) acrylate used is preferably 1 to 50 parts by mass, more preferably 10 to 45 parts by mass, out of a total of 100 parts by mass of (A), (B) and (D), 15 Most preferred is ⁇ 35 parts by weight. If it is 1 mass part or more, favorable adhesiveness will be obtained, and if it is 50 mass parts or less, there is no possibility that curability will fall.
  • a radical photopolymerization initiator is used for sensitization with visible light or actinic light such as ultraviolet rays to promote photocuring of the composition.
  • Photopolymerization initiators include benzophenone and derivatives thereof, benzyl and derivatives thereof, anthraquinone and derivatives thereof, benzoin derivatives such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and diethoxy Acetophenone, acetophenone derivatives such as 4-t-butyltrichloroacetophenone, 2-dimethylaminoethyl benzoate, p-dimethylaminoethyl benzoate, diphenyl disulfide, thioxanthone and its derivatives, camphorquinone, 7,7-dimethyl-2,3-di Oxobicyclo [2.2.1] heptan
  • At least one selected from the group consisting of benzoin derivatives, acylphosphine oxide derivatives, and ⁇ -hydroxyketone derivatives is preferable because it is highly effective. From the group consisting of acylphosphine oxide derivatives and ⁇ -hydroxyketone derivatives. One or more selected are more preferable, and it is most preferable to use an acylphosphine oxide derivative and an ⁇ -hydroxyketone derivative in combination.
  • the amount of the ⁇ -hydroxyketone derivative used is preferably 100 to 300 parts by mass, and 150 to 250 parts by mass with respect to 100 parts by mass of the acylphosphine oxide derivative. More preferred.
  • the benzoin derivatives benzyl dimethyl ketal is preferred.
  • the ⁇ -hydroxyketone derivatives 1-hydroxycyclohexyl phenyl ketone is preferred.
  • the acylphosphine oxide derivatives 2,4,6-trimethylbenzoyldiphenylphosphine oxide is preferred.
  • the amount of the photopolymerization initiator used is preferably 0.001 to 10 parts by mass, and 0.01 to 8 parts by mass with respect to 100 parts by mass in total of (A), (B) and (D). More preferred is 0.1 to 5 parts by mass. If it is 0.001 mass part or more, favorable adhesiveness will be obtained, and if it is 10 mass parts or less, favorable deep part curability will be obtained.
  • a plasticizer is a compound used in order to adjust the softness
  • the boiling point is preferably 150 ° C. or higher.
  • Plasticizers include monoester compounds that do not have (meth) acryloyl groups, polyester compounds that do not have (meth) acryloyl groups, monoether compounds that do not have (meth) acryloyl groups, and those that have (meth) acryloyl groups.
  • Monoester compounds not having (meth) acryloyl groups or polyester compounds not having (meth) acryloyl groups include isostearyl isostearate, isocetyl isostearate, isopropyl isostearate, 2-hexyldecyl isostearate, isostearic acid 2 -Octyldodecyl, isopropyl myristate, octyldodecyl myristate, isocetyl myristate, isopropyl myristate, isostearyl lactate, polyglyceryl monoisostearate, hexyl laurate, hexyl decyl laurate, isononyl isononanoate, 2-ethylhexyl isononanoate, isononane Isodecyl acid, isotridecyl isononanoate, nonyl isononanoate, cetoste
  • polyester compound which does not have a (meth) acryloyl group is preferable.
  • polyester compounds having no (meth) acryloyl group polyester compounds having an alkyl group having 8 to 22 carbon atoms are preferred.
  • polyester compounds having an alkyl group having 8 to 22 carbon atoms one or more selected from the group consisting of polyglyceryl triisostearate and dioctyl sebacate are preferred.
  • a monoether compound having no (meth) acryloyl group or a polyether compound having no (meth) acryloyl group didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, dieicosyl ether, Didocosyl ether, ditetracosyl ether, dihexacosyl ether, dioctacosyl ether, ditriacontyl ether, didotriacontyl ether and mixtures thereof, as well as cyclic ethers to polyhydric alcohols, sugars, alkanolamines and other initiators, Particularly, polyethers obtained by adding alkylene oxides such as propylene oxide and ethylene oxide can be mentioned.
  • Monocarbonate compounds not having (meth) acryloyl groups or polycarbonate compounds not having (meth) acryloyl groups include ethylene carbonate, 1,2-propylene carbonate, 1,2-butylene carbonate, diphenyl carbonate, dinaphthyl carbonate , Dimethyl carbonate, diethyl carbonate and the like.
  • hydrogenated conjugated diene compounds having no (meth) acryloyl group examples include hydrogenated 1,2-polybutadiene, hydrogenated 1,4-polybutadiene, terminal hydroxylated hydrogenated 1,2-polybutadiene, and terminal hydroxylated hydrogenated 1,4. -Polybutadiene and the like. Of these, hydrogenated 1,2-polybutadiene is preferred.
  • polyisoprene compound having no (meth) acryloyl group examples include polyisoprene, a maleic anhydride adduct of an isoprene polymer, a maleic anhydride adduct and a methanol adduct of an isoprene polymer, and the like.
  • polyolefin compound having no (meth) acryloyl group examples include ethylene- ⁇ olefin co-oligomer and polybutene.
  • (D) One or more selected from the group consisting of a polyester compound not having a (meth) acryloyl group and a hydrogenated conjugated diene compound not having a (meth) acryloyl group in terms of great effect among plasticizers Is preferred, and a polyester compound having no (meth) acryloyl group is more preferred.
  • polyester compounds having no (meth) acryloyl group polyester compounds having an alkyl group having 8 to 22 carbon atoms are preferred.
  • the amount of plasticizer used is preferably 1 to 80 parts by weight, more preferably 15 to 75 parts by weight, and more preferably 30 to 50 parts by weight in a total of 100 parts by weight of (A), (B) and (D). Is most preferred. If it is 1 mass part or more, favorable adhesiveness will be obtained, and if it is 80 mass parts or less, curability will not fall.
  • Antioxidants are used for improving storage stability and heat resistance of cured products.
  • Antioxidants include methylhydroquinone, hydroquinone, 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol), 6-tert-butyl-4- [3-[(2,4,4 8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphin-6-yl) oxy] propyl] -2-methylphenol, catechol, hydroquinone monomethyl ether, monotercia Libutylbutylquinone, 2,5-ditertiarybutylhydroquinone, p-benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-ditertiarybutyl-p-benzoquinone, picric acid, citric acid, phenothiazine, tertiary butyl Catechol, 2-butyl-4-hydroxyanisole
  • 6-tert-butyl-4- [3-[(2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphine- 6-yl) oxy] propyl] -2-methylphenol is preferred.
  • the amount of the antioxidant used is preferably 0.001 to 0.5 parts by mass, and preferably 0.005 to 0.1 with respect to 100 parts by mass in total of (A), (B) and (D). Part by mass is more preferable. If it is 0.001 mass part or more, the coloring and discoloration by the heat
  • composition of the present invention includes various types of elastomers such as acrylic rubber, urethane rubber, acrylonitrile-butadiene-styrene rubber, solvents such as polar organic solvents, fillers, reinforcements, and the like, as long as the object of the present invention is not impaired.
  • elastomers such as acrylic rubber, urethane rubber, acrylonitrile-butadiene-styrene rubber, solvents such as polar organic solvents, fillers, reinforcements, and the like, as long as the object of the present invention is not impaired.
  • Additives such as materials, thickeners, dyes, pigments, flame retardants, silane coupling agents and surfactants may be used.
  • the cured product bonded with the composition of the present invention can be reworked (reused) after being completely cured.
  • the rework method is not particularly limited, but the adherends are disassembled by applying a load of 0.01 to 100 N between the one or two kinds of adherends bonded together, and the adherend after disassembly The body can be reused.
  • composition of the present invention is, for example, a photocurable resin composition, and can be used as an adhesive composition or a coating composition.
  • a composite can be produced by bonding or covering an adherend with a cured product of an adhesive composition or a coating composition.
  • the various materials of the adherend are preferably at least one selected from the group consisting of triacetylcellulose, fluoropolymer, polyester, polycarbonate, polyolefin, glass, and metal. Polyester, glass, polyolefin, triacetylcellulose, fluoropolymer One or more selected from the group consisting of polycarbonate is more preferred.
  • polyester polyethylene terephthalate is preferable.
  • the polyolefin a cycloolefin polymer is preferable.
  • the composition of the present invention can be cured at a depth of 3 mm or more when irradiated with 1000 mJ / cm 2 of visible light or ultraviolet light at a wavelength of 365 nm, for example.
  • the composition of the present invention for example, after irradiating visible light or ultraviolet light from the front side of the adherend, irradiates the side where the visible light or ultraviolet light does not transmit from the side surface of the adherend, and bonds the adherend together. Is possible.
  • the following compounds were selected as the (A) component (meth) acrylate having a hydrogenated conjugated diene structure.
  • (A-2) Hydrogenated 1,2-polybutadiene terminal urethane (meth) acrylate (“KRM-8777” manufactured by Daicel Cytec, the structure is as follows, and the polyol compound is a hydrogenated 1,2-polybutadiene hydrogenated conjugated diene polyol.
  • 2-polybutadiene polyol, organic polyisocyanate compound is isophorone diisocyanate, hydroxy (meth) acrylate is 2-hydroxyethyl acrylate, polystyrene equivalent weight average molecular weight of 19000, but contains 30% by mass of n-octyl acrylate as a diluting monomer)
  • TE-2000 1,2-polybutadiene terminal urethane (meth) acrylate
  • the structure is as follows, the polyol compound is 1,2-polybutadiene polyol, which is a polybutadiene polyol, (Organic polyisocyanate compound is tolylene diisocyanate, hydroxy (meth) acrylate is 2-hydroxyethyl acrylate, weight average molecular weight 9200 in terms of polystyrene by GPC)
  • Isoprene oligomer (“UC-102” manufactured by Kuraray Co., Ltd., number average molecular weight 17,000 in terms of polystyrene by GPC, esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl methacrylate, formula In (1), Y is an ethylene group, and R is a methyl group)
  • the following compounds were selected as the water monofunctional (meth) acrylate of the component (B).
  • B-3) Lauryl acrylate (“LA” manufactured by Osaka Organic Chemical Company, hereinafter abbreviated as LA)
  • B-4) n-octyl acrylate Osaka Organic Chemical Co., Ltd., hereinafter abbreviated as NOAA
  • C The following compounds were selected as the radical photopolymerization initiator of component (C).
  • D-1) Polyglyceryl triisostearate (Nisshin Oilio “Cosmol 43V”, hereinafter abbreviated as 43V)
  • D-2) Dioctyl sebacate (“DOS” manufactured by Toyokuni Oil)
  • D-3) Hydrogenated 1,2-polybutadiene (“BI-2000” manufactured by Nippon Soda Co., Ltd.)
  • Comparison D-4) 1,2-polybutadiene (not hydrogenated, “B-2000” manufactured by Nippon Soda Co., Ltd.)
  • the specific gravity bottle was filled with the curable resin composition, and the mass in the air and the mass in pure water were measured to calculate the liquid specific gravity. Furthermore, the curable resin composition is cured by the method described in [Photocurability] to produce a cured product having a width of 25 mm ⁇ length of 25 mm ⁇ thickness of 2 mm, and the mass in the air and the mass in pure water are measured. It measured and computed hardened
  • cured material specific gravity. The cure shrinkage was calculated from the ratio of liquid specific gravity and cured product specific gravity. Curing shrinkage ((cured product specific gravity ⁇ liquid specific gravity) / (cured product specific gravity)) ⁇ 100 (%)
  • PET Polyethylene terephthalate
  • Test pieces width 50 mm ⁇ length 10 mm
  • biaxially stretched PET film Limirror T60, average thickness 190 ⁇ m, manufactured by Toray Industries, Inc.
  • ⁇ thickness 0.19 mm were bonded using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 30 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • the tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • COP adhesion evaluation peel adhesion strength between cycloolefin polymer test pieces
  • COP film ZONOR, average thickness 40 ⁇ m, manufactured by Nippon Zeon Co., Ltd.
  • test piece width 50 mm ⁇ length 10 mm ⁇ A thickness of 0.04 mm was bonded to each other using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 10 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • Triacetylcellulose (TAC) film (average thickness 40 ⁇ m, manufactured by Fuji Film) test piece (width 50 mm ⁇ length 10 mm ⁇ A thickness of 0.04 mm was bonded to each other using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 10 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide. After curing by light irradiation, by pulling the two end portions of the film that are not in close contact with the test piece bonded with the adhesive composition, the portions where the films are in close contact are peeled off, and the initial 180 ° peeling is performed.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • PVDF Polyvinylidene fluoride film (average thickness 40 ⁇ m, “DX film” manufactured by Denki Kagaku Kogyo Co., Ltd.) (width 50 mm ⁇ length) 10 mm in thickness x 0.04 mm in thickness) were bonded using a curable resin composition as an adhesive composition, with an adhesive layer thickness of 10 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • the tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • the ⁇ b value of the test piece adhered with the adhesive composition was measured with a color measuring device (“UV-VISABLE SPECTROPOHOTOMETER” manufactured by SHIMADZU) to determine the degree of yellowing (after heat and humidity resistance). Measure ⁇ b value before exposure. Yellowness was assumed (initial).
  • the curable resin composition under the light shielding frame can be cured to a deep part by irradiating light from an oblique direction or a lateral direction of the light shielding frame.
  • a deep portion with weak light for example, light having an integrated light quantity of 1000 to 3000 mJ / cm 2 .
  • weak light for example, light having an integrated light quantity of 1000 to 3000 mJ / cm 2 .
  • a visible ray or an ultraviolet ray is irradiated with 1000 mJ / cm 2 at a wavelength of 365 nm, deep curing of 3 mm or more is possible.
  • the present invention has a small curing shrinkage rate and does not cause changes in surface accuracy such as dimensional changes and warping.
  • the present invention can withstand the expansion and contraction of the adherend in the high temperature reliability test.
  • problems such as coloring after the heat resistance test, discoloration, and strength reduction after the moisture resistance test do not occur.
  • the initial ⁇ b value in a cured product having a thickness of 1 mm is 0.1 or less, and the ⁇ b value after standing at 85 ° C. for 500 hours is 0.5 or less. .
  • the composition of the present invention can be used for an adhesive composition for a touch panel laminate or a liquid crystal panel laminate.
  • the touch panel laminate and the liquid crystal panel laminate of the present invention can be used as a display.
  • the composition of the present invention can improve curability even when a transparent part or a translucent part is bonded.

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  • Polymers & Plastics (AREA)
  • Optics & Photonics (AREA)
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Abstract

L'invention fournit une composition qui possède des propriétés élevées de durcissement des parties profondes, et une résistance élevée au jaunissement induit par la chaleur, et qui comprend les composants (A) à (E) suivants : (A) un (méth)acrylate possédant une structure de diène conjugué hydrogéné ; (B) un (méth)acrylate monofonctionnel ; (C) un initiateur de polymérisation par voix photo-radicalaire ; (D) un plastifiant ; et (E) un antioxydant. De préférence, (D) le plastifiant consiste en un élément ou plus choisi dans un groupe constitué d'un composé monoester sans groupe (méth)acryloyl, d'un composé polyester sans groupe (méth)acryloyl, d'un composé monoéther sans groupe (méth)acryloyl, d'un composé polyether sans groupe (méth)acryloyl, d'un composé monocarbonate sans groupe (méth)acryloyl, d'un composé, d'un composé polycarbonate sans groupe (méth)acryloyl, et d'un composé diène conjugué hydrogéné sans groupe (méth)acryloyl.
PCT/JP2015/075321 2014-09-08 2015-09-07 Composition Ceased WO2016039289A1 (fr)

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JP2018009073A (ja) * 2016-07-12 2018-01-18 日立化成株式会社 光硬化性防湿絶縁塗料及び電子部品の製造方法
JP2018024761A (ja) * 2016-08-10 2018-02-15 アイカ工業株式会社 Ｌｅｄ硬化型防湿絶縁コート剤
WO2018110666A1 (fr) * 2016-12-14 2018-06-21 デンカ株式会社 Composition
JP2018119121A (ja) * 2017-01-27 2018-08-02 デンカ株式会社 組成物
WO2023026956A1 (fr) * 2021-08-26 2023-03-02 デクセリアルズ株式会社 Matériau photodurcissable et dispositif d'affichage d'image

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WO2012043664A1 (fr) * 2010-09-28 2012-04-05 電気化学工業株式会社 Composition de résine durcissable
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JP2018009073A (ja) * 2016-07-12 2018-01-18 日立化成株式会社 光硬化性防湿絶縁塗料及び電子部品の製造方法
JP2018024761A (ja) * 2016-08-10 2018-02-15 アイカ工業株式会社 Ｌｅｄ硬化型防湿絶縁コート剤
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JP2018119121A (ja) * 2017-01-27 2018-08-02 デンカ株式会社 組成物
WO2023026956A1 (fr) * 2021-08-26 2023-03-02 デクセリアルズ株式会社 Matériau photodurcissable et dispositif d'affichage d'image
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JP7578878B2 (ja) 2021-08-26 2024-11-07 デクセリアルズ株式会社 光硬化性材料及び画像表示装置

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