WO2022230820A1 - 光湿気硬化型接着剤組成物、及び硬化体 - Google Patents

光湿気硬化型接着剤組成物、及び硬化体 Download PDF

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WO2022230820A1
WO2022230820A1 PCT/JP2022/018760 JP2022018760W WO2022230820A1 WO 2022230820 A1 WO2022230820 A1 WO 2022230820A1 JP 2022018760 W JP2022018760 W JP 2022018760W WO 2022230820 A1 WO2022230820 A1 WO 2022230820A1
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moisture
meth
adhesive composition
light
acrylate
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PCT/JP2022/018760
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English (en)
French (fr)
Japanese (ja)
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坤 徐
彰 結城
拓身 木田
智一 玉川
康平 萩原
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積水化学工業株式会社
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Priority to KR1020237035844A priority Critical patent/KR20240004322A/ko
Priority to JP2022529937A priority patent/JPWO2022230820A1/ja
Priority to CN202280030502.1A priority patent/CN117203300A/zh
Publication of WO2022230820A1 publication Critical patent/WO2022230820A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a light and moisture-curable adhesive composition and a cured product of the light and moisture-curable adhesive composition.
  • moisture-curable adhesives containing moisture-curable resins that are cured by external moisture have been widely used.
  • a moisture-curable urethane prepolymer may be used as the moisture-curable resin.
  • a urethane prepolymer a polyurethane obtained by reacting a polyisocyanate and a polyol is widely known.
  • Polyester polyols and polyether polyols are often used as polyols, which are raw materials for polyurethanes.
  • the use of polycarbonate polyols, silicone skeleton-containing polyols, and the like has also been studied.
  • Patent Document 1 a carboxyl group characterized by having a structure derived from a silicone-containing diol compound having a hydroxyl value of 5 to 200 mgKOH/g is used as a polyurethane used in solder resist ink or overcoat ink.
  • a contained polyurethane is disclosed.
  • Patent Document 2 describes a composition used for medical devices, implants, etc., containing at least one polysiloxane macrodiol and at least one polyether and/or polycarbonate macrodiol soft segment.
  • a polyurethane elastomer composition is disclosed.
  • Patent Document 3 describes a one-part moisture-curable polyurethane coating agent useful as a moisture-proof insulation agent, which is obtained by mixing an organic polyisocyanate, a polycarbonate diol having a specific molecular weight, a polyester polyol, and a siloxane-modified polyol in a predetermined ratio. It is disclosed that those obtained by reacting with are used.
  • moisture-curable adhesives In recent years, the use of moisture-curable adhesives has expanded, and there is a growing demand for higher adhesive strength to various types of adherends. Therefore, it is required to improve the adhesive force. In addition, moisture-curable adhesives are sometimes required to maintain a certain interval or more between adherends to be adhered. However, when a general moisture-curing adhesive is placed between two adherends and adhered to each other, it is crushed by the pressure during adhesion and cannot maintain its shape, resulting in a constant bond between the adherends. It is difficult to keep the interval.
  • Patent Documents 1 to 3 are shown to improve various performances by having a silicone skeleton, but they have not been studied for use in adhesives and can be used in various substrates. No specific technique is disclosed for maintaining a constant interval between the adherends while improving the adhesive force to the adherends.
  • the present invention provides a moisture-curable adhesive composition that maintains a certain shape without being crushed even when pressure is applied during adhesion, while improving the adhesive strength to various adherends.
  • the challenge is to ensure that
  • a light and moisture-curable adhesive composition comprising a urethane prepolymer containing a polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule, and a radically polymerizable compound.
  • the (meth)acrylic acid ester compound is selected from the group consisting of a (meth)acrylic acid ester compound having an alicyclic structure, a (meth)acrylic acid ester compound having an aromatic ring, and an alkyl (meth)acrylate.
  • the content of the radical polymerizable compound is 5 parts by mass or more and 70 parts by mass or less with respect to the total amount of 100 parts by mass of the urethane prepolymer and the radical polymerizable compound, above [11] to [ 13], the optical and moisture-curable adhesive composition according to any one of the above items.
  • the light and moisture-curable adhesive composition of the present invention it is possible to secure shape retention while improving adhesive strength to various adherends.
  • FIG.1 (a) is a top view
  • FIG.1(b) is a side view.
  • the light and moisture-curable adhesive composition of the present invention contains a urethane prepolymer containing polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule, and a radically polymerizable compound.
  • the light-moisture-curable adhesive composition of the present invention has moisture-curable properties by containing a moisture-curable resin.
  • a moisture-curable resin Any type of moisture-curable resin may be used in the light moisture-curable adhesive composition as long as it contains a moisture-curable resin, but as described below, the urethane prepolymer is moisture-curable. is preferred.
  • the urethane prepolymer used in the present invention contains polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule.
  • the moisture-curable adhesive composition of the present invention secures wettability to various adherends by incorporating both a polycarbonate skeleton with high mechanical strength and a silicone skeleton with low surface free energy into the urethane prepolymer.
  • the mechanical strength of the cured product is improved. Therefore, high adhesive strength can be ensured for various types of adherends.
  • heat resistance is improved, and good adhesiveness can be secured even in a high-temperature environment.
  • the urethane prepolymer preferably has a moisture-curable functional group, and more preferably a urethane prepolymer containing an isocyanate group.
  • the content of the silicone skeleton portion may be greater than, less than or equal to the content of the polycarbonate skeleton portion on a mass basis.
  • the content of the silicone skeleton is preferably higher than the content of the polycarbonate skeleton on a mass basis.
  • the adhesive force to various types of adherends can be further improved.
  • a polycarbonate skeleton and a silicone skeleton are introduced by using both a silicone polyol and a polycarbonate polyol as polyol compounds that are raw materials.
  • the silicone skeleton portion is a portion derived from a silicone polyol
  • the polycarbonate skeleton portion is a portion derived from a polycarbonate polyol.
  • a silicone skeleton means an organopolysiloxane skeleton.
  • both polycarbonate polyol and silicone polyol are used as the polyol compound that is the raw material of the urethane prepolymer. That is, the urethane prepolymer is a reaction product of a mixture of polycarbonate polyol and silicone polyol and a polyisocyanate compound. As a result, at least part of the polyurethane constituting the urethane prepolymer can contain both a polycarbonate skeleton and a silicone skeleton in the molecule.
  • the polyurethane constituting the urethane prepolymer contains isocyanate groups by increasing [NCO]/[OH], and preferably contains a plurality of isocyanate groups in the molecule.
  • the polyol compound used to obtain the urethane prepolymer is preferably a diol compound, and the polyisocyanate compound is preferably a diisocyanate compound. Therefore, the polyurethane constituting the urethane prepolymer preferably has two isocyanate groups. Also, each isocyanate group is preferably contained at the end of the molecule.
  • the amount of the silicone polyol blended may be greater, lesser, or the same than the blended amount of the polycarbonate on a mass basis. More is preferable. For example, if the blending amount of the silicone polyol is greater than the blending amount of the polycarbonate, the content of the silicone skeleton portion in the urethane prepolymer will be greater than the content of the polycarbonate skeleton portion.
  • the ratio (Si/PC) of the compounding amount (Si) of the silicone polyol to the compounding amount (PC) of the polycarbonate polyol is preferably 5/95 or more and 95 on a mass basis. /5 or less, more preferably 10/90 or more and 90/10 or less, and still more preferably 15/85 or more and 85/15 or less.
  • the lower limit is more preferably greater than 50/50, and even more preferably 60/40 or more.
  • the silicone skeleton portion is a portion derived from a silicone polyol
  • the polycarbonate skeleton portion is a portion derived from a polycarbonate polyol. Therefore, the preferred range of the mass-based ratio of the content of the silicone skeleton portion to the content of the polycarbonate skeleton portion in the urethane prepolymer is as described in the above ratio (Si/PC).
  • the polyol compound used as a raw material may consist of a polycarbonate polyol and a silicone polyol, but may contain polyols other than these as long as the effects of the present invention are not impaired.
  • the urethane prepolymer may be a reaction product of polycarbonate polyols, silicone polyols, and mixtures with other polyols and polyisocyanate compounds.
  • the blending ratio of polyols other than polycarbonate polyols and silicone polyols (other polyols) is preferably 30% by mass or less, more preferably 20% by mass or less, still more preferably 10% by mass or less, and most preferably 10% by mass or less, based on the total polyol compound. is 0% by mass.
  • the urethane prepolymer may have other polyol-derived moieties in addition to the silicone skeleton and the polycarbonate skeleton, and the preferred range of the content of the other polyol-derived moieties in the urethane prepolymer is the above. It is the same as the blending ratio derived from other polyols.
  • the urethane prepolymer may be used singly or as a mixture of two or more.
  • each urethane prepolymer is preferably a reaction product obtained by reacting a polyol compound with a polyisocyanate compound.
  • at least one of the polyol compound and the polyisocyanate compound used as raw materials may be different from each other.
  • the polyol compound used as a raw material in each urethane prepolymer contains both a polycarbonate polyol and a silicone polyol.
  • any one of the two or more urethane prepolymers may use both polycarbonate polyol and silicone polyol as raw material polyol compounds. It is not necessary to use both polyols.
  • silicone polyols examples include hydroxy group-modified organopolysiloxane compounds having an organopolysiloxane skeleton and hydroxy groups. Moreover, the silicone polyol is preferably a silicone diol having two hydroxyl groups. Specific examples of hydroxy group-modified organopolysiloxane compounds include a compound having an organopolysiloxane skeleton and hydroxyl groups at both ends thereof, and a compound having an organopolysiloxane skeleton and two hydroxyl groups at one end thereof. etc.
  • the terminal hydroxy group may be directly bonded to the Si atom constituting the organopolysiloxane skeleton, or may be bonded via a hydrocarbon group or a hydrocarbon group having an ether bond.
  • the hydrocarbon group has, for example, about 2 to 50 carbon atoms, preferably about 2 to 30 carbon atoms. Silicone polyols may be used singly or in combination of two or more.
  • the weight average molecular weight of the silicone polyol is preferably from 100 to 10,000, more preferably from 500 to 5,000, and even more preferably from 800 to 3,000.
  • the weight average molecular weight is improved. Therefore, by using a mixture of a polycarbonate polyol and a silicone polyol as a raw material for producing a urethane prepolymer, a urethane prepolymer containing a polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule can be produced appropriately. be able to. Then, by adjusting the elastic modulus of the cured product within an appropriate range, the adhesion and the like can be improved.
  • polycarbonate polyol Polycarbonate diols are preferred as polycarbonate polyols, and specific examples of polycarbonate diols include compounds represented by the following formula (1).
  • R is a divalent hydrocarbon group having 4 or more and 16 or less carbon atoms, and n is an integer of 2 or more and 500 or less.
  • R is preferably an aliphatic saturated hydrocarbon group.
  • R is an aliphatic saturated hydrocarbon group
  • the heat resistance tends to be good.
  • yellowing or the like due to heat deterioration or the like is less likely to occur, and weather resistance is improved.
  • R composed of an aliphatic saturated hydrocarbon group may have a cyclic structure, it preferably has a chain structure from the viewpoint of easily improving flexibility and the like.
  • R in the chain structure may be linear or branched.
  • n is preferably 5 or more and 200 or less, more preferably 5 or more and 100 or less, and even more preferably 5 or more and 50 or less.
  • R contained in polycarbonate polyol may be used individually by 1 type, and may be used in combination of 2 or more types.
  • at least a portion thereof is preferably a chain aliphatic saturated hydrocarbon group having 6 to 16 carbon atoms.
  • the chain aliphatic saturated hydrocarbon group having 6 or more and 16 or less carbon atoms preferably has 6 or more and 12 or less carbon atoms, more preferably 6 or more and 10 or less carbon atoms.
  • R may be linear groups such as a tetramethylene group, pentylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, and, for example, a 3-methylpentylene group. It may be branched such as a methylpentylene group such as a methylpentylene group or a methyloctamethylene group.
  • R in one molecule may be the same or different.
  • R preferably contains a branched saturated aliphatic hydrocarbon group, and from the viewpoint of weather resistance, R contains a linear saturated aliphatic hydrocarbon group. is preferred.
  • Branched R and linear R may be used in combination in the polycarbonate polyol.
  • Polycarbonate polyols may be used singly or in combination of two or more.
  • the weight average molecular weight of the polycarbonate polyol is preferably 100 or more and 10000 or less, more preferably 500 or more and 5000 or less, and even more preferably 800 or more and 3000 or less.
  • the weight average molecular weight is preferably 100 or more and 10000 or less, more preferably 500 or more and 5000 or less, and even more preferably 800 or more and 3000 or less.
  • polyisocyanate compound examples of polyisocyanate compounds used as raw materials for urethane prepolymers include aliphatic polyisocyanate compounds and aromatic polyisocyanate compounds.
  • aliphatic polyisocyanate compounds include hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, transcyclohexane-1,4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and cyclohexane diisocyanate.
  • Aliphatic polyisocyanate compounds may be those obtained by increasing these.
  • aromatic polyisocyanate compounds include diphenylmethane diisocyanate, liquid modified diphenylmethane diisocyanate, tolylene diisocyanate, and naphthalene-1,5-diisocyanate.
  • the aromatic polyisocyanate compound may be a multimer of these compounds, polymeric MDI, or the like.
  • the polyisocyanate compound is preferably a diisocyanate compound.
  • a polyisocyanate compound may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the weight average molecular weight of the urethane prepolymer is not particularly limited, it is preferably 800 or more and 20,000 or less. By setting the weight-average molecular weight within the above range, the elastic modulus of the cured product can be adjusted within an appropriate range while improving the applicability of the light and moisture-curable adhesive composition.
  • the weight average molecular weight of the urethane prepolymer is more preferably 1500 or more, more preferably 2000 or more, and more preferably 18000 or less, still more preferably 15000 or less.
  • a weight average molecular weight is a value which measures by a gel permeation chromatography (GPC), and is calculated
  • Shodex LF-804 (manufactured by Showa Denko KK) can be used as a column for measuring the weight average molecular weight in terms of polystyrene by GPC. Moreover, tetrahydrofuran is mentioned as a solvent used in GPC.
  • the light moisture-curable adhesive composition of the present invention contains a radically polymerizable compound.
  • a radically polymerizable compound By containing a radically polymerizable compound, the light and moisture-curable adhesive composition of the present invention is imparted with photocurability and becomes a light and moisture-curable adhesive composition. Further, in a semi-cured state after photocuring and before moisture curing, it has hardness of a certain level or more, and shape retention can be ensured. If the shape retainability in the semi-cured state can be secured, it becomes easier to secure a constant space between adherends by the cured body formed from the light and moisture-curable adhesive composition.
  • the light and moisture-curable adhesive composition contains a radically polymerizable compound, a certain amount of adhesive strength is imparted only by light irradiation, so even in a semi-cured state after light curing and before moisture curing. A certain level of adhesive strength can be secured.
  • the radically polymerizable compound is not particularly limited as long as it is a radically polymerizable compound having photopolymerizability, and is a compound having a radically polymerizable functional group in the molecule.
  • a compound having an unsaturated double bond is suitable as the radically polymerizable functional group, and the radically polymerizable functional group includes a (meth)acryloyl group, a vinyl group, a styryl group, an allyl group, and the like.
  • a (meth)acryloyl group is preferable from the viewpoint of reactivity. Therefore, the radically polymerizable compound is a compound having a (meth)acryloyl group (hereinafter, also referred to as "(meth)acrylic compound" ) is preferred.
  • (meth)acrylic compounds include (meth)acrylic acid ester compounds, epoxy (meth)acrylates, urethane (meth)acrylates, and the like.
  • urethane (meth)acrylate does not have a residual isocyanate group.
  • (meth)acryloyl group means acryloyl group or (meth)acryloyl group
  • (meth)acrylate” means acrylate or methacrylate, and the same applies to other similar terms. be.
  • the (meth)acrylic acid ester compound may be monofunctional, bifunctional, or trifunctional or more.
  • monofunctional (meth)acrylate compounds include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, isomyristyl (meth)acrylates, alkyl (meth)acrylates such as stearyl (meth)acrylate, cyclohexyl (meth)acrylate, 4-tert-butylcyclohexyl (meth)acryl
  • acrylate methoxyethylene glycol (meth)acrylate, alkoxyethylene glycol (meth)acrylate such as ethoxyethylene glycol (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate polyoxyethylene-based (meth)acrylates such as acrylates, ethyl carbitol (meth)acrylates, ethoxydiethylene glycol (meth)acrylates, ethoxytriethylene glycol (meth)acrylates, and ethoxypolyethylene glycol (meth)acrylates;
  • the (meth)acrylic acid ester compound may have an aromatic ring.
  • phenoxyalkyl (meth)acrylates such as Furthermore, it may be a (meth)acrylate having a plurality of benzene rings such as a fluorene skeleton or a biphenyl skeleton, and specific examples thereof include fluorene-type (meth)acrylates and ethoxylated o-phenylphenol acrylates.
  • Phenoxypolyoxyethylene-based (meth)acrylates such as phenoxydiethyleneglycol (meth)acrylate, phenoxypolyethyleneglycol (meth)acrylate, nonylphenoxydiethyleneglycol (meth)acrylate and nonylphenoxypolyethyleneglycol (meth)acrylate are also included.
  • monofunctional (meth)acrylic acid ester compounds include tetrahydrofurfuryl (meth)acrylate, alkoxylated tetrahydrofurfuryl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate, 3-ethyl-3- (Meth)acrylates having a heterocyclic structure such as oxetanylmethyl (meth)acrylate, various imide (meth)acrylates, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoro Propyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-(meth)acryloyloxyethyl succinate, 2-( meth) acryloyloxyethyl hexahydro
  • bifunctional (meth)acrylate compounds include 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di( meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, Polypropylene glycol di(meth)acrylate, ethylene oxide-added bisphenol A di(meth)acrylate, propylene oxide-added bisphenol A
  • tri- or higher functional ones include, for example, trimethylolpropane tri(meth)acrylate, ethylene oxide-added trimethylolpropane tri(meth)acrylate, propylene oxide-added trimethylolpropane tri(meth) ) acrylate, caprolactone-modified trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethylene oxide-added isocyanuric acid tri(meth)acrylate, glycerin tri(meth)acrylate, propylene oxide-added glycerin tri(meth)acrylate, tris (Meth)acryloyloxyethyl phosphate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate
  • Examples of the epoxy (meth)acrylate include those obtained by reacting an epoxy compound with (meth)acrylic acid.
  • the reaction between the epoxy compound and (meth)acrylic acid is preferably carried out in the presence of a basic catalyst or the like according to a conventional method.
  • the epoxy (meth)acrylate may be monofunctional or polyfunctional such as bifunctional, but polyfunctional is preferred, and bifunctional is more preferred.
  • Examples of epoxy compounds that are raw materials for synthesizing the epoxy (meth)acrylate include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 2,2′-diallylbisphenol A type epoxy resin.
  • urethane (meth)acrylate for example, a product obtained by reacting an isocyanate compound with a (meth)acrylic acid derivative having a hydroxyl group can be used.
  • a catalytic amount of a tin-based compound or the like for the reaction between the isocyanate compound and the (meth)acrylic acid derivative, it is preferable to use a catalytic amount of a tin-based compound or the like as a catalyst.
  • the urethane (meth)acrylate may be monofunctional or polyfunctional such as bifunctional, but bifunctional is preferred.
  • isocyanate compounds used to obtain urethane (meth)acrylates include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris ( Polyisocyanate compounds such as isocyanatophenyl)thiophosphate, tetramethylxylylene diisocyanate, 1,6,11-undecane triisocyanate and the like can be mentioned.
  • MDI diisocyanate
  • isocyanate compound a chain-extended polyisocyanate compound obtained by reacting a polyol with an excess isocyanate compound can also be used.
  • polyols include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
  • Examples of (meth)acrylic acid derivatives having a hydroxyl group include dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
  • dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
  • Examples of commercially available urethane (meth)acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL8402, EBECRYL8411, EBECRYL8412 ⁇ EBECRYL8413 ⁇ EBECRYL8804 ⁇ EBECRYL8803 ⁇ EBECRYL8807 ⁇ EBECRYL9270 ⁇ EBECRYL210 ⁇ EBECRYL4827 ⁇ EBECRYL6700 ⁇ EBECRYL220 ⁇ EBECRYL2220( ⁇ ) ⁇ UN-9000H ⁇ UN-9000A ⁇ UN-7100 ⁇ Resin UN-1255, Artresin UN-330, Artresin UN-3320HB, Artresin UN-1200TPK, Artresin SH-500B (all manufactured by Neagari Kogyo Co., Ltd.), U-2HA, U-2PHA, U-3HA, U -4HA, U-6H, U-6
  • radically polymerizable compounds other than those mentioned above can also be used as appropriate.
  • Other radically polymerizable compounds include, for example, N,N-dimethyl(meth)acrylamide, N-(meth)acryloylmorpholine, N-hydroxyethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N- (Meth)acrylamide compounds such as isopropyl (meth)acrylamide and N,N-dimethylaminopropyl (meth)acrylamide, vinyls such as styrene, ⁇ -methylstyrene, N-vinyl-2-pyrrolidone and N-vinyl- ⁇ -caprolactam compounds and the like.
  • the (meth)acrylic acid ester compound is preferably a monofunctional (meth)acrylic acid ester compound. It is more preferable to include at least one selected.
  • a radically polymerizable compound it is also preferable to use a monofunctional (meth)acrylate compound and a urethane (meth)acrylate together.
  • the content of the radically polymerizable compound is preferably 5 parts by mass with respect to 100 parts by mass of the total amount of the urethane prepolymer and the radically polymerizable compound. It is more than 70 mass parts or less.
  • the amount of the urethane prepolymer can be increased to a certain amount or more, and by making the urethane prepolymer moisture-curable, an appropriate moisture-curable property can be imparted to the light moisture-curable adhesive composition. can be granted.
  • the content of the radical polymerizable compound is more preferably 10 parts by mass or more and 60 parts by mass or less, still more preferably 20 parts by mass or more and 50 parts by mass or less, and even more preferably 25 parts by mass or more and 45 parts by mass or less. is.
  • the total amount of the urethane prepolymer and the radical polymerizable compound is not particularly limited, but is preferably 70% by mass or more, more preferably 75% by mass or more and 97% by mass or less, based on the total amount of the light moisture-curable adhesive composition. Preferably, it is 80% by mass or more and 95% by mass or less.
  • the photo-moisture-curable adhesive composition of the present invention further contains a photopolymerization initiator.
  • a photopolymerization initiator By containing a photopolymerization initiator, it is possible to appropriately impart photocurability to the photo-moisture-curable adhesive composition.
  • photopolymerization initiators include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthone.
  • Examples of commercially available photopolymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, Lucirin TPO (all manufactured by BASF), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (both manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the like.
  • the content of the photopolymerization initiator in the light moisture-curable adhesive composition is preferably 0.01 parts by mass or more and 10 parts by mass or less, more preferably 0.1 parts by mass with respect to 100 parts by mass of the radically polymerizable compound. It is more than 5 mass parts or less.
  • the content of the photopolymerization initiator is within these ranges, the resulting photo-moisture-curable adhesive composition has excellent photocurability and storage stability.
  • the photoradical polymerizable compound is appropriately cured, and the adhesive strength tends to be improved.
  • the light moisture-curable adhesive composition of the present invention may contain a filler.
  • a filler By containing a filler, the light and moisture-curable adhesive composition of the present invention has suitable thixotropic properties, which facilitates good shape retention after application.
  • a particulate filler may be used as the filler.
  • Preferred fillers include inorganic fillers such as silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among these, silica is preferable because the light and moisture-curable adhesive composition has excellent ultraviolet transmittance.
  • the filler may be subjected to hydrophobic surface treatment such as silylation treatment, alkylation treatment, and epoxidation treatment.
  • a filler may be used individually by 1 type, and 2 or more types may be used in combination.
  • the content of the filler is preferably 0.5 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 25 parts by mass or less, still more preferably It is 2 parts by mass or more and 15 parts by mass or less.
  • the photo-moisture-curable adhesive composition of the present invention contains a moisture-curing acceleration catalyst, a coupling agent such as a silane coupling agent, a titanate-based coupling agent, a zirconate-based coupling agent, and a wax.
  • a coupling agent such as a silane coupling agent, a titanate-based coupling agent, a zirconate-based coupling agent, and a wax.
  • Other additives such as particles, ionic liquids, colorants, expanded particles, expanded particles, reactive diluents, antioxidants, radical scavengers, etc. may be contained.
  • a moisture-hardening acceleration catalyst is a catalyst that accelerates the moisture-hardening reaction of a moisture-curable resin. By using a moisture-curing acceleration catalyst, the moisture-curing property of the light-moisture-curable adhesive composition becomes more excellent, making it easier to increase adhesive strength.
  • Specific examples of moisture curing acceleration catalysts include amine-based compounds and metal-based catalysts.
  • Examples of amine compounds include compounds having a morpholine skeleton such as di(methylmorpholino) diethyl ether, 4-morpholinopropyl morpholine, 2,2′-dimorpholino diethyl ether, bis(2-dimethylaminoethyl) ether, 1,2 -Dimethylamino group-containing amine compounds having two dimethylamino groups such as bis(dimethylamino)ethane, triethylamine, 1,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-1,4 -diazabicyclo[2.2.2]octane and the like.
  • a morpholine skeleton such as di(methylmorpholino) diethyl ether, 4-morpholinopropyl morpholine, 2,2′-dimorpholino diethyl ether, bis(2-dimethylaminoethyl) ether, 1,2 -Dimethylamin
  • metal-based catalysts examples include tin compounds such as di-n-butyltin dilaurate, di-n-butyltin diacetate and tin octylate; zinc compounds such as zinc octoate and zinc naphthenate; zirconium tetraacetylacetonate; copper naphthenate; Other metal compounds such as cobalt naphthenate are included.
  • the content of the moisture curing acceleration catalyst in the light moisture-curable adhesive composition is relative to 100 parts by mass of the light moisture-curable adhesive composition. , preferably 0.1 to 10 parts by mass, more preferably 0.2 to 8 parts by mass, still more preferably 0.3 to 5 parts by mass.
  • the light-moisture-curable adhesive composition may be diluted with a solvent, if necessary.
  • each amount (parts by mass, mass%) of the light moisture-curable adhesive composition is based on the solid content, i.e., parts by mass excluding the solvent , means % by weight.
  • a mixer is used to prepare a urethane prepolymer, and, if necessary, a radically polymerizable compound, a photopolymerization initiator, a moisture curing acceleration catalyst, and a filler. and a method of mixing with other additives such as an agent and a coupling agent.
  • mixers include homodispers, homomixers, universal mixers, planetary mixers (planetary stirring devices), kneaders, and three rolls.
  • the cured product of the light and moisture-curable adhesive composition has a storage elastic modulus of 0.01 MPa or more and 50 MPa or less at an elongation of 25%.
  • the light and moisture-curable adhesive composition has a storage elastic modulus of 0.01 MPa or more at an elongation of 25% of the cured product, so that cohesive failure is unlikely to occur even when shearing or the like is applied, and the adhesive strength is sufficiently improved. can be higher.
  • the pressure to 50 MPa or less, the elasticity of the cured product becomes appropriate, and the adhesive strength to various adherends can be easily improved.
  • the storage elastic modulus of the cured product of the light moisture-curable adhesive composition at an elongation rate of 25% is preferably 0.05 MPa or more, more preferably 0.1 MPa or more, from the viewpoint of improving the adhesive strength to various adherends. 0.2 MPa or more is more preferable, 25 MPa or less is preferable, 15 MPa or less is more preferable, and 8 MPa or less is even more preferable.
  • the storage elastic modulus at 25% elongation of the cured product is the storage elastic modulus measured at 23° C. in a state in which the cured product is elongated by 25%.
  • the storage elastic modulus of the cured product at an elongation of 25% can be measured by the following method.
  • the light and moisture-curable adhesive composition is poured into a Teflon (registered trademark) mold having a width of 2 mm, a length of 10 mm, and a thickness of 1 mm, and cured to obtain a cured body sample.
  • the obtained cured body sample is pulled up to 100% elongation using a tensile tester, and the storage elastic modulus at 25% elongation is determined from the resulting tensile curve.
  • the measurement conditions are 25° C. and a tensile speed of 50 mm/min.
  • Curing of the light and moisture-curable adhesive composition for obtaining a cured product sample may be carried out by the following method depending on the curing mechanism, as long as the light and moisture-curable adhesive composition can be completely cured.
  • UV-LED wavelength 365 nm
  • Moisture hardening is carried out by leaving it to stand.
  • the light and moisture-curable adhesive composition of the present invention is preferably cured and used as a cured product.
  • the cured product is preferably obtained by curing a light and moisture-curable adhesive composition with light and moisture.
  • the photo-moisture-curable adhesive composition of the present invention can be used by being photo-cured by light irradiation to, for example, a B-stage state (semi-cured state), and then further cured by moisture to be fully cured. preferable.
  • the light and moisture-curable adhesive composition may be used, for example, to bond the adherends together by being placed between the adherends and cured. More specifically, the light-moisture-curable adhesive composition is applied to one adherend, then photo-cured by light irradiation to a B-stage state, and the photo-cured light-moisture-curable adhesive composition It is preferable that the other adherend is superimposed on the object, and the adherends are temporarily adhered with an appropriate adhesive force. After that, the light moisture-curable adhesive composition in the B-stage state was completely cured by curing a moisture-curable resin such as a urethane prepolymer with moisture, and was superimposed via the light moisture-curable adhesive composition. The adherends are joined with sufficient adhesive force.
  • a moisture-curable resin such as a urethane prepolymer with moisture
  • the light and moisture-curable adhesive composition contains a radically polymerizable compound, a certain thickness or more can be secured even when the other adherend is superimposed in the B-stage state. Therefore, it is possible to maintain a constant interval between the adherends.
  • the application of the light moisture-curable adhesive composition to the adherend is preferably carried out, for example, with a dispenser, but is not particularly limited.
  • the light to be irradiated during photocuring is not particularly limited as long as it is light that cures the radically polymerizable compound, but ultraviolet rays are preferable.
  • the light moisture-curable adhesive composition when completely cured by moisture, it may be left in the air for a predetermined period of time.
  • the light-moisture-curable adhesive composition of the present invention is preferably used as an adhesive for electronic devices. Therefore, although the adherend is not particularly limited, it is preferably various parts constituting an electronic device. Examples of various parts that constitute an electronic device include electronic parts, substrates to which electronic parts are attached, semiconductor chips, and the like. Examples of electronic devices include, but are not limited to, display devices such as liquid crystal displays and organic EL displays. Further, the electronic device may be a portable electronic device or the like, or may be a large-sized electronic device or the like.
  • the light and moisture-curable adhesive composition of the present invention can ensure high adhesive strength to various materials. Therefore, the material of the adherend is not particularly limited, and may be any of metal, glass, plastic, etc., and can be adhered to various types of plastics with high adhesive strength.
  • the shape of the adherend is not particularly limited, and examples thereof include film-like, sheet-like, plate-like, panel-like, tray-like, rod-like, box-like, and housing-like shapes.
  • the optical moisture-curable adhesive composition of the present invention is used for obtaining assembled parts by bonding substrates together, for example, inside electronic devices.
  • the assembly part thus obtained has a first substrate, a second substrate, and the cured product of the present invention, wherein at least a portion of the first substrate is at least a portion of the second substrate. is joined through a hardened body.
  • At least one electronic component is preferably attached to each of the first substrate and the second substrate.
  • the light moisture-curable resin compositions 10 obtained in Examples and Comparative Examples were placed in an environment of 20 to 25° C. with a width of 1.0 ⁇ 0.05 mm, It was applied to the first plate 11 so as to have a length of 25 ⁇ 2 mm and a thickness of 0.2 ⁇ 0.05 mm.
  • the optical moisture-curable adhesive composition 10 was photo-cured by irradiating 1000 mJ/cm 2 of ultraviolet rays using a UV-LED (wavelength: 365 nm).
  • the second plate 12 is superimposed, and a weight of 100 g is allowed to stand thereon for 10 seconds in a state where there is no gap material, thereby applying a load of 0.04 MPa to the cured product in the photocured state. Acted for 10 seconds.
  • the weight of 100 g was removed, and the sample 13 for evaluation was prepared by leaving it in an environment of 23° C. and 50 RH% for 3 days for moisture curing (main curing).
  • SUS plates were used as the first and second plates 11 and 12.
  • the prepared evaluation sample 13 is pulled at a speed of 12 mm / min in the shear direction S using a tensile tester in an environment of 20 to 25 ° C.
  • the adhesive force was measured by measuring the strength of the adhesive.
  • the measured adhesive strength was evaluated according to the following evaluation criteria.
  • the moisture-curable resin composition obtained in the comparative example does not have photocurability
  • the adhesive strength was measured in the same manner as described above, except that the photocuring by irradiation with ultraviolet rays was omitted. Evaluation was made according to the following evaluation criteria.
  • ⁇ PMMA adhesion> The adhesive force was measured in the same manner as described above, except that polymethyl methacrylate resin plates (PMMA plates) were used as the first and second plates 11 and 12 instead of SUS plates.
  • the measured adhesive strength was evaluated according to the following evaluation criteria. AA: 150 N or more A: 100 N or more and less than 150 N B: 80 N or more and less than 100 N C: less than 80 N
  • urethane prepolymer 1 having isocyanate groups at both ends.
  • the weight average molecular weight of the obtained urethane prepolymer 1 was 10,000.
  • Components other than the moisture-curable urethane resin used in each example and comparative example were as follows.
  • (Radical polymerizable compound) Acrylic 1: urethane acrylate, manufactured by Daicel Allnex, trade name “EBECRYL8411”, bifunctional, weight average molecular weight 12000, diluted with 20% by mass isobornyl acrylate (IBOA), urethane acrylate content 80% by mass
  • Acrylic 2 Phenoxyethyl acrylate, manufactured by Kyoeisha Chemical Co., Ltd., trade name “Light acrylate PO-A”, monofunctional acrylic 3: Lauryl acrylate: manufactured by Kyoeisha Chemical Co., Ltd., trade name “Light acrylate LA”, monofunctional acrylic 4: Cyclohexyl acrylate: Osaka Organic, trade name "Viscoat #155" Filler: trimethylsilylated silica, trade name "R812" manufactured by Nippon Aerosil Co., Ltd., primary particle
  • Examples 1 to 4 Comparative Examples 1 to 3
  • each material was stirred at a temperature of 50°C with a planetary stirrer (manufactured by Thinky Co., Ltd., "Awatori Mixer"), and then at a temperature of 50°C with three ceramic rolls. They were uniformly mixed to obtain light moisture-curable adhesive compositions or moisture-curable adhesive compositions of Examples 1 to 4 and Comparative Examples 1 to 3.
  • a urethane prepolymer containing a polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule and a light and moisture-curable adhesive composition containing a radically polymerizable compound were used. By doing so, it was possible to secure a constant adhesive strength to adherends made of various materials, and to achieve good shape retention.
  • the moisture-curable adhesive compositions of Comparative Examples 1 and 2 contained a urethane prepolymer containing a polyurethane having a polycarbonate skeleton and a silicone skeleton in the molecule, but did not contain a radically polymerizable compound. I didn't.

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PCT/JP2022/018760 2021-04-28 2022-04-25 光湿気硬化型接着剤組成物、及び硬化体 WO2022230820A1 (ja)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
JPH09194560A (ja) * 1996-01-11 1997-07-29 Toray Ind Inc 湿気硬化性組成物
JPH10259222A (ja) * 1997-01-14 1998-09-29 Toray Ind Inc 湿気硬化性樹脂およびその製造法
US20170183551A1 (en) * 2015-12-24 2017-06-29 Nan Ya Plastics Corporation Polyurethane adhesive and use of the same
JP2020105485A (ja) * 2018-12-26 2020-07-09 信越化学工業株式会社 伸縮性膜及びその形成方法
CN111500235A (zh) * 2020-05-25 2020-08-07 上海牛元工贸有限公司 适用于美缝预处理和修补的免砸砖湿固化液体防水组合物

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Publication number Priority date Publication date Assignee Title
AUPO251096A0 (en) 1996-09-23 1996-10-17 Cardiac Crc Nominees Pty Limited Polysiloxane-containing polyurethane elastomeric compositions
JP2007100036A (ja) 2005-10-07 2007-04-19 Showa Denko Kk カルボキシル基含有ポリウレタンおよび熱硬化性ポリウレタン樹脂組成物
JP2008156501A (ja) 2006-12-25 2008-07-10 Hitachi Kasei Polymer Co Ltd 一液湿気硬化型ポリウレタンコーティング剤、それを用いて防湿絶縁処理された実装回路板、及びその実装回路板の製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09194560A (ja) * 1996-01-11 1997-07-29 Toray Ind Inc 湿気硬化性組成物
JPH10259222A (ja) * 1997-01-14 1998-09-29 Toray Ind Inc 湿気硬化性樹脂およびその製造法
US20170183551A1 (en) * 2015-12-24 2017-06-29 Nan Ya Plastics Corporation Polyurethane adhesive and use of the same
JP2020105485A (ja) * 2018-12-26 2020-07-09 信越化学工業株式会社 伸縮性膜及びその形成方法
CN111500235A (zh) * 2020-05-25 2020-08-07 上海牛元工贸有限公司 适用于美缝预处理和修补的免砸砖湿固化液体防水组合物

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