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WO2019073979A1 - Composition d'adhésif photodurcissable, et procédé de collage - Google Patents

Composition d'adhésif photodurcissable, et procédé de collage Download PDF

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Publication number
WO2019073979A1
WO2019073979A1 PCT/JP2018/037619 JP2018037619W WO2019073979A1 WO 2019073979 A1 WO2019073979 A1 WO 2019073979A1 JP 2018037619 W JP2018037619 W JP 2018037619W WO 2019073979 A1 WO2019073979 A1 WO 2019073979A1
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Prior art keywords
group
meth
adhesive composition
sensitive adhesive
acrylate
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Ceased
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PCT/JP2018/037619
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English (en)
Japanese (ja)
Inventor
岡村　直実
加納　伸悟
寛生 阿部
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Cemedine Co Ltd
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Cemedine Co Ltd
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Priority to JP2019548204A priority Critical patent/JPWO2019073979A1/ja
Publication of WO2019073979A1 publication Critical patent/WO2019073979A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers

Definitions

  • the present invention relates to a photocurable pressure-sensitive adhesive composition and a bonding method.
  • the present invention relates to a photocurable pressure-sensitive adhesive composition that rapidly photocures even in air, and a bonding method.
  • Patent Document 1 a photocurable composition containing a photopolymerizable acrylic ester is applied to one adherend and then irradiated with ultraviolet rays to polymerize the acrylic ester to increase the viscosity (B-staged And is considered to impart tackiness), and a method of adhesively fixing the other adherend in this state is disclosed.
  • a radio frequency identification (RFID) tag using an antenna component as one adherend and an IC chip as the other adherend is shown.
  • a moisture curable resin is further used for the photocurable composition to ensure adhesion.
  • the photocurable composition containing the photopolymerizable acrylic acid ester is applied to one adherend, and the acrylic acid ester is polymerized by applying light to give tackiness, and then the other adherend is applied.
  • Methods of bonding the body are believed to be particularly useful in the manufacture of electronic devices. According to such a method, it is easy to peel off the adherend which has once adhered for alignment and the like.
  • an adhesive sheet or adhesive tape it is often difficult to place the adhesive sheet or adhesive tape in a predetermined shape and place it in a predetermined place, but According to the bonding method, it is relatively easy to apply the uncured photocurable composition to a predetermined place.
  • the isocyanate group in the isocyanate group-containing compound [a] which is a reaction product of the polyol (a1) and the polyisocyanate (a2) is a hydroxyl group of a hydroxyl group-containing (meth) acrylate (a3)
  • An active energy ray-curable pressure-sensitive adhesive composition comprising a polyisocyanate derivative [A] formed by forming a urethane bond with a hydroxyl group of a saturated alcohol (a4) and an ethylenically unsaturated monomer [B] Is disclosed.
  • the active energy ray-curable pressure-sensitive adhesive composition described in Patent Document 2 is a composition which is cured by ultraviolet irradiation with a high pressure mercury lamp, and the balance between the adhesion to the substrate and the weather resistance is good.
  • the photopolymerization initiator having good surface curability is efficiently decomposed, and there is a surface which is less susceptible to oxygen inhibition.
  • a large space is required because a duct for removing generated ozone is required.
  • the adherend since the energy of the ultraviolet light emitted from the high pressure mercury lamp is high, the adherend may be damaged, or the heat from the high pressure mercury lamp may cause thermal damage to the adherend, and the adherend is resistant to damage. Must be selected.
  • the problem to be solved by the present invention is a photocurable pressure-sensitive adhesive composition containing a urethane oligomer having a specific group at the end, and photopolymerization proceeds rapidly even in the presence of oxygen such as in the air, and it takes a long time It is an object of the present invention to provide a photocurable pressure-sensitive adhesive composition using a photocurable pressure-sensitive adhesive composition which does not require light irradiation or oxygen blocking equipment and sufficiently cures even by irradiation with light of long wavelength, and a bonding method.
  • R 1 represents a hydrogen atom or a methyl group.
  • the said photocurable adhesive composition may further contain (B) monofunctional (meth) acrylate.
  • the said photocurable adhesive composition may further contain (D) tackifying resin.
  • the present invention provides a product having a cured product of any one of the above photocurable pressure-sensitive adhesive compositions in order to achieve the above object.
  • the present invention is a method of bonding a plurality of adherends in order to achieve the above object, and (A) 3- (3) linked via a urethane bond represented by the following general formula (1) Applying a photocurable pressure-sensitive adhesive composition containing a urethane oligomer having an acryloyloxy-2-hydroxypropyl group at the end, and (C) a photoinitiator to at least one adherend, And a light irradiation step of irradiating light emitted from the LED in the presence of oxygen to the photocurable pressure-sensitive adhesive composition applied to the adherend, and the photocurable composition applied to one adherend and irradiated with light. Bonding the other adherend (but excluding the protective sheet for the adhesive surface as the other adherend) to the pressure-sensitive adhesive composition.
  • R 1 represents a hydrogen atom or a methyl group.
  • a photocurable adhesive composition may further contain (B) monofunctional (meth) acrylate.
  • a photocurable adhesive composition may further contain (D) tackifying resin.
  • the present invention also provides a method for producing an adhesive body produced using the adhesion method described in any one of the above to achieve the above object.
  • the photocurable pressure-sensitive adhesive composition and the adhesion method according to the present invention light is produced even in the presence of oxygen such as in air using the photocurable pressure-sensitive adhesive composition containing a urethane oligomer having a specific group at the end.
  • An adhesion method can be provided.
  • the photocurable pressure-sensitive adhesive composition of the present invention is a composition that exhibits tackiness quickly by irradiation with light such as active energy rays emitted from a light emitting diode (LED). That is, the photocurable pressure-sensitive adhesive composition is 3- (meth) acryloyloxy-2 linked via a urethane bond (A) which is a group having a specific structure capable of suppressing oxygen inhibition by oxygen in the environment. And-containing a urethane oligomer having a hydroxypropyl group at the end, and (C) a photoinitiator.
  • the photocurable pressure-sensitive adhesive composition of the present invention is 3- (meth) acryloyloxy-2-hydroxypropyl linked via a urethane bond represented by the following general formula (1) as component A It contains a urethane oligomer having a group at its end and (C) a photoinitiator.
  • the photocurable pressure-sensitive adhesive composition may further contain (B) a monofunctional (meth) acrylate and / or (D) a tackifying resin.
  • a urethane oligomer having a specific group for suppressing oxygen inhibition is used as the component A, excellent tackiness is exhibited even if it is photocuring in air.
  • R 1 represents a hydrogen atom or a methyl group.
  • Component A Urethane Oligomer Having a 3- (Meth) acryloyloxy-2-hydroxypropyl Group at the End, which is Linked via a Urethane Linkage
  • a urethane oligomer having a 3- (meth) acryloyloxy-2-hydroxypropyl group connected via a urethane bond which is a component A has a number average molecular weight in which the oligomer end or side chain is (meth) acryloylated Is a (meth) acrylate oligomer having a urethane bond of 1,000 or more, and improves adhesion.
  • the component A contained in the photocurable pressure-sensitive adhesive composition it is preferable to use a compound capable of suppressing oxygen inhibition by oxygen in the environment to exhibit good adhesiveness.
  • the component A of the present invention is a compound having a plurality of electron withdrawing groups, and is a compound in which an active radical is easily generated in a portion sandwiched between the plurality of electron withdrawing groups.
  • the component A of the present invention is a compound which has a plurality of electron withdrawing groups and which is likely to generate an active radical in a portion sandwiched between the plurality of electron withdrawing groups.
  • component A of the curable pressure-sensitive adhesive composition is suitable. That is, it contains, as component A, a secondary hydroxyl group disposed in a portion sandwiched by a plurality of -CH 2 groups (specifically, two -CH 2 groups) and an electron attractive group located at the molecular end It has been found that urethane oligomers having a group via a urethane bond are preferred.
  • examples of the component A include a urethane oligomer having a 3- (meth) acryloyloxy-2-hydroxypropyl group connected via a urethane bond represented by the above general formula (1) at the end.
  • the following mechanism is presumed as a mechanism which suppresses the polymerization inhibition by oxygen. That is, in radical polymerization, the polymerization inhibition by oxygen occurs, and the reaction rate of the monomer decreases. In particular, a decrease in reaction rate occurs in the surface layer exposed to air. Oxygen inhibition is caused by the low polymerization ability of peroxy radicals generated by trapping in oxygen the initiating radicals generated from the photoinitiator and the polymerization terminal radical generated in the polymerization process of monomers, and are caused by the termination of the polymerization reaction.
  • a peroxy radical having hydrogen extraction ability is newly generated by extracting hydrogen from the urethane oligomer. It is believed that the alpha carbon radical of the secondary hydroxyl group initiates polymerization. In addition, since the generated ⁇ -carbon radical of secondary hydroxyl group can also capture oxygen, the effect of reducing the oxygen concentration in the system is also considered. It is speculated that oxygen inhibition is suppressed by these mechanisms.
  • Urethane oligomers having a 3- (meth) acryloyloxy-2-hydroxypropyl group at the end, which is linked via a urethane bond may be simply referred to as “component A” or “urethane oligomer of component A”).
  • the number average molecular weight is preferably 2,000 or more, more preferably 3,000 or more, in terms of polystyrene in GPC from the viewpoint of securing good elongation characteristics of the pressure-sensitive adhesive.
  • the number average molecular weight is preferably about 100,000 or less, more preferably 50,000 or less, still more preferably 30,000 or less, from the viewpoint of securing an appropriate viscosity of the composition and securing good workability.
  • component A having a glass transition point (Tg) of 10 ° C. or less is preferable, component A of 0 ° C. or less is more preferable, ⁇ 10 ° C.
  • Tg glass transition point
  • the component A can be synthesized by reacting a urethane prepolymer (an oligomer having an isocyanate group at a molecular terminal, which is obtained by reacting a hydroxyl group-containing oligomer with an excess of organic polyisocyanate) and glycerin mono (meth) acrylate.
  • a urethane prepolymer an oligomer having an isocyanate group at a molecular terminal, which is obtained by reacting a hydroxyl group-containing oligomer with an excess of organic polyisocyanate
  • glycerin mono (meth) acrylate glycerin mono (meth)
  • hydroxyl group-containing oligomers polyether-based hydroxyl group-containing oligomers, polyester-based hydroxyl group-containing oligomers, non-aromatic polycarbonate-based hydroxyl group-containing oligomers, acrylic-based hydroxyl group-containing oligomers, having a number average molecular weight of about 1,000 to 50,000
  • the diene polymer system hydroxyl group containing oligomer etc. are mentioned. From the viewpoint of imparting flexibility to the cured product, diols and monools are preferred, and from the viewpoint of curability, diols are preferred. Further, a hydroxyl group-containing oligomer which is liquid at 50 ° C. is preferred from the ease of handling at the time of blending and the handling of the composition. These hydroxyl group-containing oligomers can be used alone or in combination of two or more.
  • polyether based hydroxyl group containing oligomer examples include polyethylene glycol, polypropylene glycol, polyoxyethylene polyoxypropylene glycol, polypropylene triol, and polytetramethylene glycol. From the viewpoint of imparting flexibility to the cured product, polypropylene glycol (PPG) and polytetramethylene glycol (PTMG) are preferred. From the viewpoint of imparting flexibility to the cured product, polypropylene monool is more preferable. In order to improve the degree of crosslinking of the cured product, triol and tetraol are preferred.
  • Examples of the synthesis method of the polyoxyalkylene polymer include, but not particularly limited to, a polymerization method using an alkali catalyst such as KOH and a polymerization method using a double metal cyanide complex catalyst. According to a polymerization method using a double metal cyanide complex catalyst, it is possible to obtain a polyoxyalkylene polymer having a high molecular weight of Mw (weight average molecular weight) / Mn (number average molecular weight) of 1.6 or less and a narrow molecular weight distribution. From the viewpoint of improving the coating workability of the composition (a viewpoint of reducing the viscosity), the polypropylene polyol preferably has Mw / Mn of 1.6 or less. From the viewpoint of imparting flexibility to the cured product, it is preferable to use a polypropylene polyol having a number average molecular weight of 6,000 or more.
  • polyester-based hydroxyl group containing oligomers include reaction products of diol components and polyvalent carboxylic acids, and addition reaction products of diol components and lactones.
  • a liquid polyester-based hydroxyl group-containing oligomer is preferable, and as the diol component, a branched aliphatic glycol having 5 or more carbon atoms such as neopentyl glycol (NPG) or 2-methyl-1,5-pentanediol (MPD) is preferable.
  • NPG neopentyl glycol
  • MPD 2-methyl-1,5-pentanediol
  • dicarboxylic acids having 5 or more carbon atoms such as adipic acid and sebacic acid are preferable.
  • Non-aromatic polycarbonate-based hydroxyl group-containing oligomer for example, a component selected from diol components such as 1,4-butanediol, 1,6-hexanediol, 1,5-pentanediol and the like, short chain such as dimethyl carbonate and the like Mention may be made of polycarbonate diols which can be obtained by reaction with dialkyl carbonates.
  • non-crystalline such as 1,6-hexanediol / 1,5-pentanediol copolymerization, 1,6-hexanediol / 1,4-butanediol copolymerization, etc.
  • non-crystalline such as 1,6-hexanediol / 1,5-pentanediol copolymerization, 1,6-hexanediol / 1,4-butanediol copolymerization, etc.
  • Nonaromatic polycarbonate-based hydroxyl group-containing oligomers which are liquid at 20 ° C. are preferred.
  • the acrylic hydroxyl group-containing oligomer is preferably an acrylic hydroxyl group-containing oligomer in which the position of the hydroxyl group is at the end of the main chain of the oligomer, and is preferably a liquid acrylic hydroxyl group-containing oligomer at 20 ° C.
  • Examples of (meth) acrylic acid ester monomers constituting the main chain of acrylic hydroxyl group-containing oligomer include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate and (meth) acrylic acid Examples thereof include (meth) acrylic acid alkyl esters having 1 to 18 carbon atoms such as 2-ethylhexyl and stearyl (meth) acrylate. These may be used alone or in combination of two or more.
  • introducing a crosslinkable silicon group into the main chain of the acrylic hydroxyl group-containing oligomer by using an alkoxysilyl group-containing (meth) acrylic acid ester such as ⁇ - (meth) acryloyloxypropyltrimethoxysilane in combination it can.
  • An acrylic acid alkyl ester having 4 to 8 carbon atoms and a methacrylic acid alkyl ester having 10 and 12 carbon atoms are preferable, and n-butyl acrylate and 2-ethylhexyl acrylate are more preferable, because acrylic resin having 4 to 8 carbon atoms is preferable because acrylic resin is excellent in flexibility.
  • the acid n-butyl is most preferred.
  • (meth) acrylic acid represents acrylic acid and / or methacrylic acid.
  • a living radical polymerization method is used from the viewpoint of obtaining an acrylic hydroxyl group-containing oligomer having a narrow molecular weight distribution and a low viscosity and having a hydroxyl group at the molecular chain terminal. It is preferred to use.
  • an acrylic hydroxyl group-containing oligomer having a hydroxyl group at one end is obtained, a reaction using a thiol compound having a hydroxyl group such as 2-mercaptoethanol described in JP-A-2000-344823 and a metallocene compound can be used.
  • a reaction using a compound having a thiol group such as thioglycerol (3-mercapto-1,2-propanediol) described in JP-A-2000-128911 and a secondary hydroxyl group can also be used.
  • An acrylic hydroxyl group-containing oligomer having two hydroxyl groups at one end is preferable from the viewpoint of good flexibility of the cured product and maintenance and improvement of adhesion.
  • the number average molecular weight of the acrylic hydroxyl group-containing oligomer is preferably 2,000 or more, preferably 5,000 or more, and more preferably 8,000 or more, from the viewpoint of securing good flexibility of the pressure-sensitive adhesive.
  • the number average molecular weight is preferably about 100,000 or less, more preferably 50,000 or less, and still more preferably 30,000 or less, from the viewpoint of securing an appropriate viscosity of the composition and ensuring good workability.
  • diene polymerization system hydroxyl group containing oligomer examples include 1,2-polybutadienediol, a hydrogenated product of 1,2-polybutadienediol, and 1,4-polybutadienediol.
  • organic polyisocyanates examples include aromatic polyisocyanates such as tolylene diisocyanate (TDI), aromatic aliphatic polyisocyanates such as xylylene diisocyanate (XDI), isophorone diisocyanate (IPDI), etc. Alicyclic polyisocyanates and aliphatic polyisocyanates such as hexamethylene diisocyanate (HMDI) can be mentioned.
  • aromatic polyisocyanates such as tolylene diisocyanate (TDI)
  • aromatic aliphatic polyisocyanates such as xylylene diisocyanate (XDI), isophorone diisocyanate (IPDI)
  • HMDI hexamethylene diisocyanate
  • the component A may contain a crosslinkable silicon group.
  • the crosslinkable silicon group is moisture cured by dark reaction after curing by light reaction. Thereby, the improvement of the adhesiveness by a crosslinkable silicon group and the improvement of the heat resistance by the increase in a crosslinking point can be expected.
  • the crosslinkable silicon group is a group having a hydroxyl group or a hydrolyzable group bonded to a silicon atom and capable of being crosslinked by a silanol condensation reaction.
  • a crosslinkable silicon group the crosslinkable silicon group represented by Formula (2) is mentioned.
  • R 2 represents an alkyl group having 1 to 20 carbon atoms, a substituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and 7 to 20 carbon atoms
  • X is a hydrolyzable group, and when two or more X are present, they may be the same or different.
  • a represents 0, 1, 2 or 3; The case where a is 2 or 3 in the crosslinkable silicon group of Formula (2) is preferable. When a is 3, the curing rate is higher than when a is 2.
  • R 2 examples include alkyl groups such as methyl and ethyl, substituted alkyl groups such as methoxymethyl, and cycloalkyl groups such as cyclohexyl.
  • a methyl group is preferable, and from the viewpoint of increasing the curing rate, a substituted alkyl group in which the ⁇ carbon is substituted with a polar group is preferable.
  • hydrolysable group shown by said X What is necessary is just a conventionally well-known hydrolysable group.
  • An alkoxy group is preferable from the viewpoint of mild hydrolyzability and easy handling. Among the alkoxy groups, those having a smaller number of carbon atoms are more reactive, and the reactivity becomes lower as the number of carbon atoms increases, as in the order of methoxy group> ethoxy group> propoxy group. Although it can be selected according to the purpose and application, usually, a methoxy group or an ethoxy group is used.
  • a is preferably 2 or more in consideration of the curability.
  • crosslinkable silicon group examples include trialkoxysilyl groups such as trimethoxysilyl group and triethoxysilyl group (-Si (OR 3 ) 3 ); dialkoxyl groups such as methyldimethoxysilyl group and methyldiethoxysilyl group alkoxysilyl group (-SiR 2 (OR 3) 2 ) can be mentioned.
  • R 2 is the same as described above
  • R 3 is an alkyl group such as a methyl group or an ethyl group.
  • the crosslinkable silicon group is preferably a trimethoxysilyl group or a triethoxysilyl group from the viewpoint of high reactivity, and a trimethoxysilyl group is more preferable. From the viewpoint of obtaining a cured product having flexibility, methyldimethoxysilyl group and methyldiethoxysilyl group are preferable.
  • the position at which the crosslinkable silicon group is contained is preferably the end of the polymer from the viewpoint of obtaining a pressure-sensitive adhesive having sufficient flexibility.
  • the ratio of the crosslinkable silicon group is preferably 10% or more, more preferably 20% or more, from the viewpoint of improving the heat resistance after moisture curing with respect to the total number of (meth) acryloyloxy groups and the crosslinkable silicon group. It is more preferable that the content is at least relative. Further, from the viewpoint of the curability after irradiation with light, 90% or less is preferable, 80% or less is more preferable, and 70% or less is still more preferable.
  • Component A containing a crosslinkable silicon group is to react the urethane prepolymer with a compound having a crosslinkable silicon group such as glycerin mono (meth) acrylate and 3-mercaptopropyltrimethoxysilane and an isocyanate reactive group.
  • a compound having a crosslinkable silicon group such as glycerin mono (meth) acrylate and 3-mercaptopropyltrimethoxysilane and an isocyanate reactive group.
  • the hydroxyl group- and crosslinkable silicon group-containing oligomer can be synthesized by reacting a hydroxyl group-containing oligomer with a compound having a crosslinkable silicon group such as 3-isocyanatopropyltrimethoxysilane and an isocyanate group.
  • Component B monofunctional (meth) acrylate
  • the monofunctional (meth) acrylate which is the component B lowers the viscosity without reducing the adhesiveness, and from the viewpoint of improving the coating properties (workability) of the composition.
  • a monofunctional (meth) acrylate a monofunctional (meth) acrylate having a number average molecular weight of 1,000 or less can be used.
  • the monofunctional (meth) acrylate is preferably liquid at 50 ° C. from the viewpoint of ease of compounding and the like.
  • R 4 is a hydrogen atom or a methyl group
  • m is an integer of 2 to 4
  • n is an integer of 1 to 20
  • R 5 is a hydrogen atom or an unsubstituted or substituted alkyl group, The unsubstituted or substituted phenyl group is shown.
  • a long-chain hydrocarbon-based (meth) acrylate having 8 to 20 carbon atoms and / or a compound of the general formula (3) is preferable in that the tackiness of the pressure-sensitive adhesive is excellent, and the long carbon number is 8 to 20
  • a chain hydrocarbon (meth) acrylate, a (meth) acrylate having a hydroxyl group, and a (meth) acrylate having an alkoxy group are more preferable, and a long chain hydrocarbon (meth) acrylate having 8 to 20 carbon atoms is most preferable.
  • a (meth) acrylate having a hydroxyl group a monomer represented by the following general formula (4) and having one 3- (meth) acryloyloxy-2-hydroxypropyl group linked by a polar linking group A (hereinafter referred to as “ 3 Ac2 HPM "), and is preferred from the viewpoint that oxygen inhibition hardly occurs.
  • R 1 represents a hydrogen atom or a methyl group
  • A represents a polar linking group
  • R 6 represents an organic group.
  • Examples of polar linking groups include (thio) ether linking group, ester (-O-CO-) linking group, urethane (-O-CO-NH-) linking group, amine (-NR 7 2- ) linking group (R 7 ) a substituted or unsubstituted alkyl group are well linked to the ring structure may have.) cited be the same or different .2 one R 7 groups of a substituted or unsubstituted aryl group .
  • the linking group is preferably an ether (-O-) linking group, an ester linking group, or a urethane linking group from the viewpoint of suppressing polymerization inhibition by oxygen, and an ether linking group or a urethane linking group is more preferable. Ether linking groups are most preferred for their availability.
  • R 6 As an organic group of R 6 , a substituted or unsubstituted alkylene group, a substituted or unsubstituted phenyl group and a group of the following general formula (5) can be mentioned.
  • m is an integer of 2 to 4
  • n is an integer of 1 to 20
  • R 8 represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted phenyl group.
  • the organic group of R 6 is preferably an alkyl group having 8 to 18 carbon atoms.
  • a crosslinkable silicon group-containing group such as a 3-triethoxysilylpropyl group as the organic group of R 6 is preferable from the viewpoint of dual curing (post curing) to improve adhesiveness and adhesiveness at high temperature.
  • monofunctional (meth) acrylates are as follows. First, as long-chain hydrocarbon (meth) acrylates having 8 to 20 carbon atoms, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, isostearyl (meth) acrylate, etc. It can be mentioned.
  • alicyclic (meth) acrylates examples include isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and dicyclopentenyl oxyethyl (meth) acrylate.
  • the (meth) acrylate having a hydroxyl group for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexane dimethanol mono (meth) acrylate, glycerol mono Hydroxyalkyl (meth) acrylates such as (meth) acrylates; polyalkylene glycol mono (meth) acrylates such as polyethylene glycol mono (meth) acrylates, polypropylene glycol mono (meth) acrylates, and polyethylene glycol-polypropylene glycol copolymers It can be mentioned.
  • aromatic (meth) acrylate benzyl (meth) acrylate, phenol alkylene oxide modified (meth) acrylate, alkylphenol alkylene oxide modified (meth) acrylate, p-cumylphenol alkylene oxide modified (meth) acrylate, and o-phenyl Phenol alkylene oxide modified (meth) acrylate etc. are mentioned.
  • ethylene oxide, a propylene oxide, etc. are mentioned as alkylene oxide.
  • alkoxypolyethylene glycol mono (meth) acrylates such as ethoxydiethylene glycol (meth) acrylate
  • alkoxypolypropylene glycol mono (meth) acrylates such as methoxytripropylene glycol (meth) acrylate
  • alkoxypolyethylene glycol -Polypropylene glycol copolymer etc. can be mentioned.
  • (meth) acrylate having a carboxyl group As (meth) acrylate having a carboxyl group, (meth) acrylic acid, polycaprolactone modified product of (meth) acrylic acid, Michael addition type polymer of (meth) acrylic acid, 2-hydroxyethyl (meth) acrylate, and anhydride Examples thereof include phthalic acid adducts and adducts of 2-hydroxyethyl (meth) acrylate and succinic anhydride.
  • Examples of the (meth) acrylate having a heterocyclic group include tetrahydrofurfuryl (meth) acrylate, N- (meth) acryloyloxyethyl hexahydrophthalimide and the like, and examples of the (meth) acrylate having an amino group include N, N -Dimethylaminoethyl acrylate etc. are mentioned.
  • Examples of (meth) acrylates having an alkoxysilyl group include 3- (trimethoxysilyl) propyl (meth) acrylate and the like, and examples of (meth) acrylates having an epoxy group include glycidyl (meth) acrylate and cyclohexene oxide Examples thereof include (meth) acrylates, and examples of (meth) acrylates having a phosphoric acid group include 2- (meth) acryloyloxyethyl acid phosphate and the like.
  • (meth) acrylate having a fluoroalkyl group, (meth) acrylate having a tribromophenyl group, and the like can be mentioned.
  • a (meth) acrylate having a polar group such as a hydroxyl group, a carboxyl group or a phenoxy group is preferable because it enhances the cohesion of the adhesive and improves the adhesive strength.
  • the (meth) acrylate having an alicyclic group is preferable in that it has good curability, is less likely to reduce the adhesive strength, and has a good performance balance.
  • the blending ratio of the component B is the component A (or the total of the (meth) acryloyloxy group-containing polymer excluding the component A and the component A described below) 100 2,000 parts by mass or less is preferable, 1,000 parts by mass or less is more preferable, and 300 parts by mass or less is the most preferable. From the viewpoint of improving the coating workability of the composition, 2 parts by mass or more is preferable, 100 parts by mass is more preferable, 5 parts by mass or more is more preferable, and 10 parts by mass or more is the most preferable.
  • C component photo initiator
  • a photoinitiator a photo radical generator, a photo base generator, a photo acid generator etc.
  • the photo radical generator is a compound that generates radicals by irradiation of active energy rays such as ultraviolet rays and electron beams.
  • active energy rays such as ultraviolet rays and electron beams.
  • the photopolymerization initiator (C) when used as the polymerization initiator, it can be suitably used for heat-resistant members, and thus can be used for various applications.
  • Photoradical generators examples include benzyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-hydroxy-2-methyl-1-phenyl-propan-1-one and the like.
  • ⁇ -Aminoacetophenone series such as ⁇ -hydroxyacetophenone series, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone series, bis Acyl phosphine oxides such as (2,4,6-trimethylbenzoyl) -phenyl phosphine oxide, benzophenones such as methyl benzoylbenzoate, thioxanthones such as isopropyl thioxanthone, 1.2-octanedione, 1- [4- ( Oxime esters such as phenylthio)-, 2- (O-benzoyloxime)], bis
  • photoinitiators of benzyl ketal type, ⁇ -hydroxyacetophenone type, ⁇ -amino acetophenone type, acyl phosphine oxide type, oxime ester type and titanocene type are preferable because they have high sensitivity and a small addition amount.
  • a light source containing ultraviolet light of a short wavelength such as a metal halide lamp, an electrodeless lamp (fusion lamp) or a high pressure mercury lamp as a light source
  • the surface curability is good and oxygen inhibition occurs.
  • UV-LED ultraviolet light emitting diode
  • Ie Sensitive to long-wavelength ultraviolet light (i-line (365 nm wavelength), h-line (405 nm wavelength), g-line (436 nm wavelength), etc.), and the cleavage reaction proceeds sufficiently even with relatively low light energy -Aminoacetophenone type, acyl phosphine oxide type, oxime ester type and titanocene type photo radical initiators are preferably used, and ⁇ -aminoacetophenone type, acyl
  • UV-LED As a light source, low power consumption and long life, no duct is necessary because ozone is not generated, heat generation at the time of irradiation is small, thermal damage to the adherend is small, and lighting only at the time of irradiation Since it is preferable to use a UV-LED having merits, it is possible to start photopolymerization initiation of ⁇ -aminoacetophenone type, acyl phosphine oxide type, oxime ester type and titanocene type, which have high sensitivity to long wavelength active energy rays. It is preferred to use an agent.
  • the photocurable pressure-sensitive adhesive composition according to the present invention has good surface curability even when it is cured by active energy rays of long wavelength, and can reduce the influence of oxygen inhibition.
  • the photobase generator also acts as a curing catalyst for the crosslinkable silicon group when irradiated with light, in particular, when the component A contains the crosslinkable silicon group, or the photocurable pressure-sensitive adhesive composition is (B) simple.
  • a functional (meth) acrylate is included and the said (B) monofunctional (meth) acrylate contains a crosslinkable silicon group, it is highly effective.
  • produces an amine compound by the effect
  • a photolatent primary amine that generates an amine compound having a primary amino group by the action of active energy rays, and an amine compound having a secondary amino group by the action of active energy rays Any of a photolatable secondary amine to be generated and a photolatent tertiary amine to generate an amine compound having a tertiary amino group by the action of active energy rays can be used.
  • the photolatable tertiary amine is more preferable in that the generated base shows high catalytic activity.
  • the photolatent primary amine and the photolatent secondary amine for example, an ortho-nitrobenzyl urethane compound described in WO 2015/088021; a dimethoxybenzyl urethane compound; a benzoin carbamate; o-acyl oximes O-carbamoyl oximes; N-hydroxyimido carbamates; formanilide derivatives; aromatic sulfonamides; cobalt amine complexes and the like.
  • photolatable tertiary amine for example, ⁇ -amino ketone derivative, ⁇ -ammonium ketone derivative, benzylamine derivative, benzyl ammonium salt derivative, ⁇ -amino alkene derivative, ⁇ -ammonium alkene derivative described in WO2015-088021 And amine imides, benzyloxycarbonylamine derivatives which generate an amidine by light, and salts of carboxylic acid and tertiary amine.
  • photobase generators preferred is a photolatable tertiary amine from the viewpoint that the generated base exhibits high catalytic activity, and from the viewpoint of high base generation efficiency and good storage stability as a composition, benzyl ammonium Salt derivatives, benzyl-substituted amine derivatives, ⁇ -amino ketone derivatives and ⁇ -ammonium ketone derivatives are preferred.
  • the addition amount of the photoinitiator is not particularly limited, when the addition amount is small, the curing does not proceed to the deep part, and curing failure may occur. Therefore, the “A component” or “A component and A component described later 0.05 parts by weight or more is preferable, 0.1 parts by weight or more is more preferable, and 1 part by weight or more is more preferable with respect to 100 parts by weight of the (meth) acryloyloxy group-containing polymer except for. In addition, when the amount of the initiator is large, the initiator may remain and the curing physical properties may be adversely affected.
  • the addition amount is a weight of (A) component or (A) component and (A) component to be described later 30 parts by weight or less is preferable, 20 parts by weight or less is more preferable, and 10 parts by weight or less is more preferable with respect to 100 parts by weight of the “combined”.
  • the component A may not contain the (meth) acryloyloxy group-containing polymer except the component A.
  • the composition preferably contains a photo base generator as a photoinitiator.
  • a silicon compound having a Si—F bond can be further added.
  • the composition can be post-cured by moisture in the air after the composition is photocured.
  • a silicon compound having a Si—F bond various compounds containing a silicon group having a Si—F bond (hereinafter sometimes referred to as a fluorosilyl group) can be used. Both inorganic compounds and organic compounds can be used as the silicon compound having a Si—F bond.
  • a silicon compound having a Si—F bond an organic compound having a fluorosilyl group is preferable, and an organic polymer having a fluorosilyl group is more preferable because of its high safety.
  • low molecular weight organosilicon compounds having a fluorosilyl group are preferable in that the composition has a low viscosity.
  • silicon compounds having a Si-F bond examples include fluorosilanes described in WO2015-088021, compounds having a fluorosilyl group described in WO2015-088021, and fluorosilyls described in WO2015-088021. And organic polymers having a group.
  • tackifying resin which is D component there is no restriction
  • resin which has polar groups such as rosin ester resin, phenol resin, xylene resin, xylene phenol resin, terpene phenol resin, and an aromatic with comparatively small polarity
  • Conventional tackifying resins such as various petroleum resins such as aliphatic-aromatic copolymer type or alicyclic type, or coumarone resin, low molecular weight polyethylene resin, terpene resin, and resins obtained by hydrogenating these be able to. These may be used alone or in combination of two or more.
  • these resins include, as aromatic petroleum resins, ⁇ -methylstyrene homopolymer resin [FTR Zero series, Mitsui Chemicals Co., Ltd. product], styrene monomer homopolymer resin [FTR 8000 series, Mitsui Chemical Co., Ltd. product, styrenic monomer / aromatic monomer copolymer resin [FMR series, Mitsui Chemicals Co., Ltd. product], ⁇ -methylstyrene / styrene copolymer resin [FTR 2000 series, Mitsui Chemical (c) And aromatic series styrene resins.
  • styrene based monomer / aliphatic based monomer copolymer based resin As aliphatic-aromatic copolymer based petroleum resin, styrene based monomer / aliphatic based monomer copolymer based resin [FTR 6000 series, Mitsui Chemicals Co., Ltd. product], styrene based monomer / ⁇ -methylstyrene / aliphatic based monomer Examples thereof include aliphatic-aromatic copolymer-based styrene resins such as copolymer resins [FTR 7000 series, manufactured by Mitsui Chemicals, Inc.].
  • the solubility parameter (hereinafter abbreviated as "SP value" in principle) calculated by the Small method using Hoy's constant is preferably 7.9 to 11.0, 8.2 to 9.8 is more preferred, and 8.5 to 9.5 is most preferred.
  • the adhesive strength of the pressure-sensitive adhesive it is preferable to select a resin having a polarity matched to the polarity of the adherend.
  • a tackifying resin for a low polarity adherend it is preferable to use a low polarity tackifying resin, and when using a high polarity adherent, it is preferable to use a high polarity tackifying resin.
  • a tackifier resin When a tackifier resin is used for a wide adherend from adherends having high polarity to adherends having low polarity, it is preferable to use a mixture of a tackifier resin having a low polarity and a tackifier resin having a high polarity.
  • the polarity (SP value) of terpene phenol resin the U series of YS Polystar (manufactured by Yashara Chemical Co., Ltd.) has an SP value of 8.69, the T series has an SP value of 8.81, the S series has an SP value of 8.98, the G series Is SP value 9.07 and K series is SP value 9.32.
  • the aromatic petroleum resin is preferably an aromatic styrene resin or an aliphatic-aromatic copolymer-based styrene resin, and more preferably a terpene phenol resin or an aliphatic-aromatic copolymer-based styrene resin. From the viewpoint of excellent adhesion, terpene phenol resin is most preferable. In addition, from the viewpoint of VOC, it is preferable to use an aliphatic-aromatic copolymer-based styrene resin
  • the blending ratio of the tackifier resin is preferably 5 to 200 parts by mass, and more preferably 10 to 150 parts by mass with respect to 100 parts by mass of the component A or the components A and B. From the viewpoint of exerting the adhesive strength, 5 parts by mass or more is preferable, and from the viewpoint of maintaining the hardness of the cured product in an appropriate range, exerting sufficient adhesive strength, and securing good workability, 200 parts by mass or less is preferable.
  • composition of the present invention a (meth) acryloyloxy group-containing polymer other than the component A, a polyfunctional (meth) acrylate, a vinyl compound having an amide group, an N-vinyl compound, (meth), as necessary, may be used.
  • Agents reinforcing agents, coloring agents, flame retardants, anti-sagging agents, antioxidants, anti-aging agents, UV absorbers, solvents, perfumes, pigments, dyes, fillers, diluents, polymerization inhibitors, solid polymers, etc. An agent may be added.
  • the (meth) acryloyloxy group-containing polymer other than the component A is a (meth) acrylate oligomer / polymer having a number average molecular weight of 1,000 or more, in which the oligomer / polymer terminal or side chain is (meth) acryloylated.
  • urethane (meth) acrylates excluding the component A acrylic (meth) acrylates (for example, “RC-100C”, “RC-200C” manufactured by Kaneka Corporation) “RC-300C”, “RC-500C”, “MM110C”; vinyl polymers having a (meth) acryloyl group described in Japanese Patent No. 4786921, etc., polyisoprene (meth) acrylates (eg, Kuraray Co., Ltd.) “UC-1”: an esterified product of maleic anhydride adduct of polyisoprene polymer and 2-hydroxyethyl methacrylate, etc.
  • acrylic (meth) acrylates for example, “RC-100C”, “RC-200C” manufactured by Kaneka Corporation) “RC-300C”, “RC-500C”, “MM110C”
  • urethane (meth) acrylates excluding the component A, polyether-based urethane (meth) acrylates (for example, “UV-3700B” and “UV-6100B” manufactured by Nippon Gosei Co., Ltd.), polyester-based urethane (meth) acrylates (for example, Nippon Gohsei "UV-2000B”, “UV-3000B”, “UV-7000B”, Negami Industrial Co., Ltd.
  • polyether-based urethane (meth) acrylates for example, “UV-3700B” and “UV-6100B” manufactured by Nippon Gosei Co., Ltd.
  • polyester-based urethane (meth) acrylates for example, Nippon Gohsei "UV-2000B”, “UV-3000B”, “UV-7000B”, Negami Industrial Co., Ltd.
  • KHP-11 "KHP-17", non-aromatic polycarbonate urethane (meth) acrylate
  • Article resin UN-9200A manufactured by Negami Chemical Industries, Ltd., acrylic (meth) urethane acrylate, 1,2-polybutadiene terminated urethane (meth) acrylate (eg, "TE-2000” manufactured by Nippon Soda Co., Ltd., “TEA- 1000 "), 1,2-polybutadiene terminated urethane (meth) acrylate Hydrogenated product (e.g., manufactured by Nippon Soda Co., Ltd. "TEAI-1000"), 1,4-polybutadiene-terminated urethane (meth) acrylate (e.g., Osaka Organic Chemical Co., Ltd. "BAC-45”), and the like.
  • the (meth) acryloyloxy group-containing polymer excluding the component A has a weight average molecular weight of 1,000 to 50,000, and preferably 3,000 to 45,000 from the viewpoint of the flexibility of the cured adhesive. And 5,000 to 20,000 are more preferable.
  • the glass transition temperature (Tg) is preferably 10 ° C. or less, more preferably 0 ° C. or less, and still more preferably ⁇ 10 ° C. or less, from the viewpoint of maintenance and improvement of flexibility at low temperature. It is preferable to show liquid at 50 ° C., more preferable to show liquid at 20 ° C., and it is further preferable to show liquid at 0 ° C. from the viewpoint of securing the ease of handling when blending with other components.
  • Multifunctional (meth) acrylate As polyfunctional (meth) acrylates having two or more (meth) acryloyl groups, 1,6-hexadiol di (meth) acrylate, neopentyl glycol di (meth) acrylate, dicyclopentanyl di (meth) acrylate , Polypropylene glycol di (meth) acrylate, 2,2-bis (4- (meth) acryloxydiethoxyphenyl) propane, or 2,2-bis (4- (meth) acryloxytetraethoxyphenyl) propane, etc.
  • Trifunctional (meth) acrylates such as functional (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris [(meth) acryloyloxyethyl] isocyanurate, dimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate ) Acrylate, or Pentaerythritol ethoxy tetra (meth) acrylate such as 4 or more functional groups is (meth) acrylate and the like.
  • the molecular weight of the polyfunctional (meth) acrylate is less than 1,000.
  • the compounding ratio of the polyfunctional (meth) acrylate is component A (or the total of the (meth) acryloyloxy group-containing polymer excluding the component A and the component A) from the viewpoint of exerting the inhibitory effect of oxygen inhibition by the component A 10 mass parts or less are preferable with respect to 100 mass parts, 5 mass parts or less are more preferable, and 2 mass parts or less are the most preferable. From the viewpoint of securing sufficient cohesion under high temperature conditions, 0.01 parts by mass or more is preferable, 100 parts by mass or more is preferable, 0.05 parts by mass or more is more preferable, and 0.1 parts by mass or more is the most preferable.
  • the cohesion of the pressure-sensitive adhesive can be further improved, and the adhesion can be further improved.
  • vinyl compounds having an amido group and N-vinyl compounds are preferable from the viewpoint of reactivity and resistance to oxygen inhibition.
  • vinyl compounds having an amido group examples include N-vinyl cyclic amides such as N-vinyl-2-pyrrolidone and N-vinyl-2-caprolactam; N, N-diethyl (meth) acrylamide, N- (2-hydroxyethyl) And acrylamides such as acrylamide and (meth) acryloyl morpholine. Acryloyl morpholine is preferred because of its good balance of curability, physical properties and safety.
  • N-vinyl compound examples include N-vinylpyrrolidone, N-vinylcaprolactam, and N-vinylacetamide.
  • N-vinyl pyrrolidone is preferable from the viewpoint of a good balance of curability and physical properties.
  • silane coupling agent acts as an adhesion promoter.
  • silane coupling agents include epoxy group-containing silanes such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane; ⁇ -aminopropyltrimethoxysilane, N Amino group-containing silanes such as-( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane; ketimines such as N- (1,3-dimethylbutylidene) -3- (triethoxysilyl) -1-propanamine -Type silanes; mercapto group-containing silanes such as ⁇ -mercaptopropyltrimethoxysilane; vinyl type unsaturated group-containing silanes such as vinyltrimethoxysilane and ⁇ -methacryloyloxyprop
  • amino group-containing silanes are reacted with an epoxy group-containing compound containing the above silanes, an isocyanate group-containing compound, and a (meth) acryloyl group-containing compound to use an amino group-modified amino group-containing silane. May be
  • amino group-containing silanes act as silanol condensation catalysts.
  • ketimine type silanes form amino group-containing silanes in the presence of water and act as a silanol condensation catalyst. Therefore, it is preferable to use a silane coupling agent other than amino group-containing silanes and ketimine-type silanes.
  • amino group-containing silanes or ketimine-type silanes are used, the type and / or amount of use thereof is adjusted within the range in which the purpose and effect of the present invention are achieved.
  • photo aminosilane generating compound The use of amino group-containing silanes and ketimine-type silanes may be limited in the present invention. However, when it is desirable to use amino group-containing silanes or ketimine-type silanes as an adhesion imparting agent, no compound having an amino group is generated before light irradiation, and amino group-containing silanes are A compound to be generated (hereinafter also referred to as a photoaminosilane generating compound) can be used.
  • the photofunctional group described in WO2015 / 088021 is exemplified by an o-nitrobenzyl group, a p-nitrobenzyl group, an oxime residue, a benzyl group, a benzoyl group, and these substituted groups and the like. Certain compounds are mentioned.
  • photoaminosilane generating compounds in which the photofunctional group is o-nitrobenzyl group include 2-nitrobenzyl-N- [3- (trimethoxysilyl) propyl] carbamate and 2-nitrobenzyl-N- [3- (triethoxy) And silyl) propyl] carbamate, 3,4-dimethoxy-2-nitrobenzyl-N- [3- (trimethoxysilyl) propyl] carbamate and the like.
  • photoaminosilane generating compounds in which the photofunctional group is p-nitrobenzyl group include 4-nitrobenzyl-N- [3- (trimethoxysilyl) propyl] carbamate and the like.
  • Examples of the photoaminosilane generating compound in which the photofunctional group is a benzyl group include 1- (3,5-dimethoxyphenyl) -1-methylethyl-N- [3- (trimethoxysilyl) propyl] carbamate and the like.
  • Examples of photoaminosilane generating compounds in which the photofunctional group is an oxime residue include benzophenone O- ⁇ [3- (trimethoxysilyl) propyl] ⁇ oxime and the like.
  • the compounding ratio of the silane coupling agent is not particularly limited, but it is preferably 0.01 to 20% by mass, more preferably 0.025 to 10% by mass in the composition. These silane coupling agents can be used alone or in combination of two or more.
  • silane coupling agent or silicate As the water absorbent, it is preferable to use the above-mentioned silane coupling agent or silicate.
  • the silicate is not particularly limited, and examples thereof include tetramethoxysilane, tetraalkoxysilane and the like, and partial hydrolytic condensates thereof.
  • a known curing catalyst can be widely used as a condensation reaction promoting catalyst for other crosslinkable silicon groups other than the photobase generator, and there is no particular limitation.
  • organic metal compounds, amines, fatty acids, organic acids A phosphoric acid ester compound etc. are mentioned, It is preferable to use a silanol condensation catalyst especially.
  • silanol condensation catalyst for example, organotin compounds; dialkyltin oxides; reaction products of dibutyltin oxide and phthalic acid esters, etc .; titanates; organoaluminum compounds; chelate compounds such as titanium tetraacetylacetonate; Organic acid bismuth etc. are mentioned.
  • the condensation reaction of the crosslinkable silicon group may proceed regardless of light irradiation, so it is preferable to use within the range in which the purpose and effects of the present invention can be achieved.
  • the photosensitizer is preferably a carbonyl compound having a triplet energy of 225 to 310 kJ / mol.
  • thioxanthone such as isopropylthioxanthone and a derivative thereof, dialkoxyanthracene derivative such as 9, 10-dibutoxyanthracene, 2- Benzophenone such as methyl benzoylbenzoate and its derivatives, coumarin derivatives such as 3-acyl coumarin, 3,3'-carbonylbiscoumarin and the like, and the like
  • thioxanthone and its derivatives and coumarin derivatives are preferable, and thioxanthone and its derivatives, benzophenone and the like
  • the derivatives and coumarin derivatives are more preferred.
  • the proportion of the photosensitizer is not particularly limited, but is preferably 0.01 to 5% by mass, and more preferably 0.025 to 2% by mass in the composition. These photosensitizers may be used alone or in combination of two or more.
  • Photopolymerization accelerator A photopolymerization accelerator can be used in combination with the initiator for the purpose of accelerating the curing reaction by the photopolymerization initiator.
  • Photopolymerization accelerators include tertiary amines such as triethylamine, triethanolamine and 2-dimethylaminoethanol; aryl phosphines such as triphenyl phosphine; aryl phosphine oxides such as triphenyl phosphine oxide; triphenyl phosphite And phosphines including aryl phosphates such as triphenyl phosphate (aryl group may have a substitution); thiols represented by ⁇ -thioglycol and the like.
  • Preferred phosphines are trifunctional phosphine derivatives, more preferably triaryl phosphines, most preferably triphenyl phosphines.
  • a resin filler resin fine powder
  • an inorganic filler an inorganic filler
  • a functional filler can be used.
  • the filler may be surface-treated with a silane coupling agent, a titanium chelating agent, an aluminum coupling agent, a fatty acid, a fatty acid ester, a rosin or the like.
  • a particulate filler made of an organic resin or the like can be used.
  • the resin filler organic fine particles of ethyl polyacrylate resin, polyurethane resin, polyethylene resin, polypropylene resin, urea resin, melamine resin, benzoguanamine resin, phenol resin, acrylic resin, styrene resin and the like can be used.
  • the resin filler may contain the black resin filler. Even in the case of using a long wavelength LED lamp or the like, it is possible to obtain good deep area curability and to achieve excellent light shielding properties and deep area curability.
  • inorganic filler examples include talc, clay, calcium carbonate, magnesium carbonate, anhydrous silicon, hydrous silicon, calcium silicate, titanium dioxide, titanium black, carbon black and the like.
  • the conductive filler described in JP-A-2013-14734, JP-A-2017-2267, JP-A-2011-508012 and the like As the functional filler, for example, the conductive filler described in JP-A-2013-14734, JP-A-2017-2267, JP-A-2011-508012 and the like; the heat insulation and the lightness etc. described in JP-A-2016-199668 etc. Hollow particles; Core-shell particles having excellent sound insulation and damping properties described in JP-A-2016-199669 etc .; Layered silicates excellent in gas-barrier etc. described in JP-A-2016-199670 etc; It is possible to use the light-reflecting filler described herein; the electromagnetic wave shielding material described in JP-A-2016-199750 and the like.
  • a solvent having a flash point (open type) of 50 ° C. or more is used as a diluent.
  • Physical properties such as viscosity can be adjusted by containing a diluent.
  • various diluents can be used as the diluent.
  • saturated hydrocarbon solvents such as normal paraffin and isoparaffin, ⁇ -olefin derivatives such as Linearn dimer (trade name of Idemitsu Kosan Co., Ltd.), aromatic hydrocarbon solvents, alcohol solvents, ester solvents
  • aromatic hydrocarbon solvents such as solvents, citric acid ester solvents such as acetyl triethyl citrate, and ketone solvents.
  • the flash point of the diluent is preferably 60 ° C. or more, more preferably 70 ° C. or more.
  • a diluent having a high flash point generally tends to have a low dilution effect on the composition, it is preferable to use a diluent having a flash point of 250 ° C. or less.
  • the flash point of a liquid mixture is said flash point.
  • a saturated hydrocarbon solvent is preferable, and normal paraffin and isoparaffin are more preferable.
  • the carbon number of normal paraffins and isoparaffins is preferably 10 to 16.
  • the compounding ratio of the diluent is preferably in the range of 0 to 50 parts by mass with respect to 100 parts by mass of the component A or 100 parts by mass of the (meth) acryloyloxy group-containing polymer excluding the component A and the component A It is more preferable to blend in the range of 0.1 to 30 parts by mass, and it is further preferable to blend in the range of 0.1 to 15 parts by mass.
  • the diluent may be used alone or in combination of two or more.
  • the content of the liquid medium is preferably 5% by weight or less, more preferably 3% by weight or less, still more preferably 1% by weight or less, based on the whole composition. Most preferred is a composition that is substantially free of (i.e., a substantially solvent-free composition).
  • substantially does not contain a liquid medium means that the composition does not contain any liquid medium, or the content thereof is 0.1% by mass or less of the composition.
  • a solvent having a flash point of 50 ° C. or less is used as a volatile solvent.
  • the polymerization inhibitor is not particularly limited, and examples thereof include radical scavengers such as hindered phenols and hindered amines, phosphorus secondary antioxidants, diethylhydroxylamine, sulfur, t-butyl catechol, potassium triiodide, N-nitrosophenylhydroxyamine aluminum salt etc. may be mentioned.
  • the polymerization inhibitors may be used alone or in combination of two or more.
  • Solid polymer As a solid polymer, a polymer solid at 20 ° C. can be used. As a solid polymer, the homopolymer which superposed
  • a block polymer comprising a hard polymer block A having a glass transition temperature of 0 ° C. or more, preferably 30 ° C. or more, and a soft polymer block B having a glass transition temperature less than 0 ° C., preferably ⁇ 10 ° C. or less Is preferred.
  • a block polymer of the hard polymer block A and the soft polymer block B there may be mentioned a non-acrylic block copolymer consisting of a styrenic polymer block A and a polymer block B comprising a conjugated diene polymer or a hydrogenated product thereof.
  • a block copolymer of styrene and a conjugated diene such as butadiene or isoprene, or a hydrogenated product thereof can be mentioned.
  • JP-A-2003-277521 is composed of a hard polymer block A such as styrene or its derivative, methyl methacrylate and an acrylic polymer block B such as butyl acrylate and 2-ethylhexyl acrylate. Particularly preferred are acrylic block copolymers.
  • acrylic block copolymer a triblock copolymer of polymethyl methacrylate-poly n-butyl acrylate-polymethyl methacrylate is preferable from the viewpoint of solubility, adhesiveness and transparency.
  • the bonding method of the present invention is not a method of producing a pressure-sensitive adhesive product such as a pressure-sensitive adhesive sheet or a pressure-sensitive adhesive tape, but directly applies a raw material serving as a pressure-sensitive adhesive upon light irradiation to an adherend to form a pressure-sensitive adhesive on the adherend
  • a raw material serving as a pressure-sensitive adhesive upon light irradiation to an adherend to form a pressure-sensitive adhesive on the adherend This is a method of bonding the other adherend to this. That is, in the bonding method of the present invention, the photocurable pressure-sensitive adhesive composition is not used after being formed into a form such as a tape, and is applied directly to one adherend and directly applied to the other adherend. It is used for adhesion (that is, the other adherend is not a film or the like such as a release liner, but is actually an adherend adhered to one adherend).
  • the adhesion method of the present invention can be used for adhesion of electronic and electrical parts etc., and is particularly suitable for adhesion of electronic parts.
  • “for on-site application” indicates that the photocurable pressure-sensitive adhesive composition is used as it is for bonding at a site where an electronic component or the like is produced. That is, in the present invention, a pressure-sensitive adhesive is processed into a shape such as a tape to prepare a molded body, and the photocurable pressure-sensitive adhesive composition of the present invention is used instead of using the molded body at a place different from the processing place. It is applied to one adherend as it is, and in this state (or at the site), it refers to an application of sticking one adherend to the other adherend.
  • the method for producing the photocurable pressure-sensitive adhesive composition is not particularly limited, and for example, component A and component C are blended in predetermined amounts, and component B and / or other compounded materials are blended if necessary, It can be manufactured by degassing and stirring. There is no restriction
  • the photocurable pressure-sensitive adhesive composition according to the present invention may be of a one-component type or a two-component type, if necessary, but it can be suitably used particularly as a one-component type.
  • the photocurable pressure-sensitive adhesive composition according to the present invention is a composition that exhibits adhesiveness by light irradiation and cures, and can be cured in normal temperature (for example, 23 ° C.) in air, and normal temperature photocurable curing Although it is suitably used as a pressure sensitive adhesive, if necessary, curing may be promoted by heating as appropriate.
  • the photocurable pressure-sensitive adhesive composition according to the present invention exhibits adhesiveness and cures when irradiated with light.
  • An adhesive can be obtained by this curing.
  • various adhesive-containing products such as electronic circuits, electronic components, construction materials, automobiles and the like can be manufactured using the photocurable adhesive composition according to the present invention.
  • the photocurable pressure-sensitive adhesive composition according to the present invention is irradiated with light, but when active energy rays are applied during curing, curing by ultraviolet light or visible light is possible as active energy rays. Available.
  • the ultraviolet light also includes g-ray (wavelength 436 nm), h-ray (wavelength 405 nm), i-ray (wavelength 365 nm), and the like.
  • the active energy ray source is not particularly limited, but can be appropriately selected according to the reaction wavelength of the photoinitiator to be used.
  • light sources include metal halide lamps, high power metal halide lamps (containing indium etc.), electrodeless lamps (fusion lamps), low pressure mercury lamps, high pressure mercury lamps, super high pressure mercury lamps, mercury-xenon lamps, argon lasers, A xenon lamp, a xenon flash lamp, an LED etc. are mentioned.
  • Each of these light sources has different emission wavelengths and energy distributions. Therefore, these light sources are preferably selected according to the reaction wavelength of the photo initiator and the like. Further, a xenon flash lamp or an LED capable of intermittently emitting active energy rays is preferable because the influence of heat on the adherend can be minimized. In particular, a UV-LED having merits such as low power consumption and long life is more preferable because it has lower radiation heat, smaller size and high freedom of design of a light irradiation device as compared with other ultraviolet lamps.
  • the emission wavelength of the UV-LED can be selected according to the combination with the photopolymerization initiator, but is preferably 280 nm or more and 450 nm or less, more preferably 300 nm or more and 450 nm or less, and still more preferably 350 nm or more and 450 nm or less.
  • a UV-LED is most preferable as a light source.
  • the irradiation energy for example, in the case of UV, preferably 10 ⁇ 20,000mJ / cm 2, more preferably 20 ⁇ 10,000mJ / cm 2, more preferably 50 ⁇ 5,000mJ / cm 2. If it is less than 10 mJ / cm 2 , the curability may be insufficient. If it is more than 20,000 mJ / cm 2 , time and cost are wasted even if light is irradiated more than necessary, and the substrate may be damaged. There is.
  • the method for applying the photocurable pressure-sensitive adhesive composition according to the present invention to an adherend is not particularly limited, but application methods such as screen printing, stencil printing, roll printing, dispenser application, spin coating and the like are suitably used.
  • a photocurable adhesive composition can be apply
  • the photocurable pressure-sensitive adhesive composition according to the present invention is applied to at least one adherend (application step).
  • the photocurable pressure-sensitive adhesive composition may be applied to one adherend, or the photocurable pressure-sensitive adhesive composition may be applied to each of both adherends.
  • a photocurable adhesive composition can be apply
  • light is irradiated to this photocurable adhesive composition (light irradiation process).
  • the photocurable pressure-sensitive adhesive composition exhibits tackiness by light irradiation.
  • the photocurable pressure-sensitive adhesive composition according to the present invention is a quick-curing type composition excellent in workability, and the cured product can be suitably used as a pressure-sensitive adhesive.
  • the photocurable pressure-sensitive adhesive composition according to the present invention can be applied directly to an adherend because it is liquid before light irradiation, and can be easily applied to an adherend having a complicated shape. And a photocurable adhesive composition exhibits adhesiveness rapidly by light irradiation, even if it does not interrupt
  • the photocurable pressure-sensitive adhesive composition according to the present invention the photocurable pressure-sensitive adhesive composition exhibiting adhesiveness after application and photoirradiation of the photocurable pressure-sensitive adhesive composition on one adherend Since the other adherend can be attached to each other, even when the adherend does not transmit light such as ultraviolet light, a plurality of adherends can be easily attached to each other.
  • the photocurable pressure-sensitive adhesive composition according to the present invention does not cure when the active energy ray is not irradiated, and does not block from the air even in the presence of oxygen (that is, even without covering with a film or the like) It is a composition which is cured by active energy ray irradiation, and is a composition having a rapid curing property excellent in rising adhesion after active energy ray irradiation. Therefore, a predetermined bonding possible time can be secured after light irradiation. Furthermore, in the present invention, a UV-LED can be used as a light source, in which case damage to the adherend can be reduced.
  • the epoxy group of the C12, 13 mixed alcohol glycidyl ether opens and bonds with the acrylic acid to form an ester bond.
  • this ring opening occurs at either the ⁇ position or the ⁇ position
  • the ⁇ adduct opened at the ⁇ position is the main component
  • the ⁇ adduct opened at the ⁇ position is the accessory component.
  • the production ratio of ⁇ -adduct to ⁇ -adduct is 100 / 0.01 to 100/70, preferably 100 / 0.1 to 100/50 in molar ratio.
  • Synthesis Example 1 a product having a compound, which is usually an ⁇ adduct, as a main component and a ⁇ adduct as an accessory component is obtained.
  • the product can be isolated by separation according to known separation methods.
  • Synthesis Example 1 a mixture containing an ⁇ -adduct and a ⁇ -adduct is obtained as a monoacrylate of component A. That is, the product obtained in Synthesis Example 1 is a product obtained by leaving all or part of the ⁇ adduct in the product obtained by the above synthesis method, and is a composition containing the ⁇ adduct as the main component.
  • main component refers to a component containing 60 mol% or more in the product
  • subcomponent refers to a component containing 40 mol% or less.
  • Synthesis Example 2 Synthesis of Urethane Acrylate (BO-3U)
  • the urethane acrylate (BO-3U) of the BA skeleton with 2 attached was obtained.
  • the number average molecular weight is a polystyrene equivalent molecular weight measured by gel permeation chromatography using a Tosoh HLC-8120 GPC as a liquid delivery system, using a Tosoh TSK-GELH type column, and using THF as a solvent.
  • Synthesis Example 3 Synthesis of Urethane Acrylate (BO-2U)
  • Obtained by reacting 1.7 g of xylylene diisocyanate (XDI) with 100 g of a primary hydroxyl group, and using 101.7 g of a urethane prepolymer (PU-BA2) having a BA skeleton at both ends of the isocyanate group 1.6 g of methacrylate and 0.05 g of a polymerization inhibitor (hydroquinone) are added and reacted at 70 ° C.
  • the urethane acrylate (DL-10000) of PPG skeleton of 2-hydroxypropyl methacrylate at both ends was obtained.
  • IR spectrum measurement it was confirmed that the absorption of -NCO derived from the isocyanate group disappeared, and the absorption of the -OH stretch derived from the hydroxyl group remained.
  • Example 1 Each compounding substance is respectively added to a flask equipped with a stirrer, thermometer, nitrogen inlet, monomer charging pipe, and water-cooled condenser at the mixing ratio shown in Table 1, and the mixture is stirred and mixed according to Example 1.
  • An adhesive composition was prepared.
  • each component A the compounds synthesized in the above-mentioned Synthesis Examples 2 to 6 were used.
  • B component C12MAc the compound synthesized in the above Synthesis Example 1 was used.
  • UV irradiation conditions UV-LED lamp (wavelength 365 nm, illuminance: 1000 mW / cm 2 ), accumulated light amount: 3000 mJ) / Cm 2 ].
  • the second adherend (austenite stainless steel) is bonded to the first adherent so as to sandwich the UV-irradiated photocurable adhesive composition in an area of 25 mm ⁇ 80 mm
  • Pressure was applied using a 2 kg roller.
  • the test piece was produced by this.
  • the peel strength was measured at a test speed of 200 mm / min according to JIS K 6854-2 (adhesive agent-peel adhesion strength test method part 2: 180 degree peel method) .
  • the test results are shown in Table 1. The same test was conducted on Examples 2 to 14 and Comparative Examples 1 and 2.
  • Examples 1-14 exhibited good properties of at least 15 (N / 25 mm) or more in the peel adhesion test. On the other hand, in all of Comparative Examples 1 and 2, the peel strength did not exceed 10 (N / 25 mm).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)

Abstract

L'invention fournit une composition d'adhésif photodurcissable et un procédé de collage. La composition d'adhésif photodurcissable de l'invention comprend un oligomère d'uréthane possédant un groupe spécifique à une extrémité. Selon l'invention, une opération de photopolymérisation se poursuit rapidement y compris en présence d'un oxygène dans l'air, ou similaire, et ni une photoirradiation de longue durée ni un équipement de blocage d'oxygène ne sont nécessaires. Cette composition d'adhésif photodurcissable comprend (A) un oligomère d'uréthane possédant à une extrémité un groupe 3-(méth)acryloyloxy-2-hydroxypropyle lié par l'intermédiaire d'une liaison uréthane représentée par la formule générale (1), et (C) un photo-initiateur. (Dans la formule générale (1), Ｒ１ représente un atome d'hydrogène ou un groupe méthyle.)
PCT/JP2018/037619 2017-10-11 2018-10-09 Composition d'adhésif photodurcissable, et procédé de collage Ceased WO2019073979A1 (fr)

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WO2020130043A1 (fr) * 2018-12-21 2020-06-25 積水化学工業株式会社 Composition adhésive, adhésif pour composant électronique et adhésif pour élément d'affichage
JP2021011569A (ja) * 2019-06-27 2021-02-04 ボスティク エス．アー． ポリウレタン／（メタ）アクリルに基づくホットメルト感圧接着性組成物
JP2021098825A (ja) * 2019-12-23 2021-07-01 東洋インキＳｃホールディングス株式会社 無溶剤型接着剤及び積層体
CN114621403A (zh) * 2020-12-11 2022-06-14 三键有限公司 片状光固化性组合物、光固化性组合物溶液、片状光固化性组合物的制造方法及层叠体

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WO2020130043A1 (fr) * 2018-12-21 2020-06-25 積水化学工業株式会社 Composition adhésive, adhésif pour composant électronique et adhésif pour élément d'affichage
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JP2021011569A (ja) * 2019-06-27 2021-02-04 ボスティク エス．アー． ポリウレタン／（メタ）アクリルに基づくホットメルト感圧接着性組成物
JP7549980B2 (ja) 2019-06-27 2024-09-12 ボスティク エス アー ポリウレタン／（メタ）アクリルに基づくホットメルト感圧接着性組成物
JP2021098825A (ja) * 2019-12-23 2021-07-01 東洋インキＳｃホールディングス株式会社 無溶剤型接着剤及び積層体
CN114621403A (zh) * 2020-12-11 2022-06-14 三键有限公司 片状光固化性组合物、光固化性组合物溶液、片状光固化性组合物的制造方法及层叠体

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