WO2013013568A1 - Compositions adhésives photodurcissables et utilisations associées - Google Patents

Compositions adhésives photodurcissables et utilisations associées Download PDF

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Publication number
WO2013013568A1
WO2013013568A1 PCT/CN2012/078238 CN2012078238W WO2013013568A1 WO 2013013568 A1 WO2013013568 A1 WO 2013013568A1 CN 2012078238 W CN2012078238 W CN 2012078238W WO 2013013568 A1 WO2013013568 A1 WO 2013013568A1
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component
meth
group
weight
parts
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PCT/CN2012/078238
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English (en)
Inventor
James Wang
Nicolas ZHOU
Jimmy Yuan
Daniel Lu
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Henkel (China) Company Limited
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Publication of WO2013013568A1 publication Critical patent/WO2013013568A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/04—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to rubbers
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide

Definitions

  • the present invention relates to photo curable adhesive compositions and use thereof.
  • Optically clear adhesives are widely used in sealing and bonding luminescent devices and optical displays, such as light-emitting diodes (LED), liquid crystal displays and touch screens, due to their good transmittance and sufficient brightness.
  • LED light-emitting diodes
  • Organosiloxane compositions are described in US 4,978,696 and US 5,5488,038. However, it is difficult to remove the organosiloxane compositions from bonded substrates after curing by irradiation, and the substrates suffer from contamination problems. Therefore, applications of organosiloxane compositions in electric and electronic devices are greatly limited.
  • WO 2009/045889 discloses an indium-tin-oxide compatible optically clear adhesive.
  • the adhesive comprises an alkyl
  • (meth)acrylate monomer having a glass transition temperature hereinafter referred to as "Tg" of about 25°C or less, an ester of (meth)acrylate monomer having a Tg greater than about 25°C, and at least one component selected from hydroxyl alkyl (meth)acrylate, unsubstituted
  • (meth)acrylamide monomer containing urea functionality, monomer containing lactam functionality, tertiary amine, alicyclic amine, aromatic amine, and combinations thereof.
  • US 2010/0148160 teaches a laminating adhesive for elastomers, which is prepared from a reactive liquid oligomer and/or polymer and a liquid monomer reative with the liquid oligomer and/or polymer.
  • the reactive liquid oligomer and/or polymer is selected from
  • liquid monomer reative with the liquid oligomer and/or polymer is selected from butyl (meth)acrylate, cyclohexanedimethylol di(meth)acrylate,
  • US 2010/0003425 discloses a photo-curable resin composition.
  • the composition contains at least one polymer selected from polyurethane acrylate, polyisoprene acrylate and an esterified product thereof, a hydrogenated terpene resin, and a butadiene polymer; at least one acrylate monomer selected from isobornyl acrylate, dicyclopentenyloxyethyl methacrylate, and
  • US 7,915,319 B2 discloses a visible light curable composition
  • a visible light curable composition comprising a urethane component, a reactive diluent, a photoinitiator and a photoinitiator synergist
  • the urethane component comprising one or more of an aliphatic urethane triacrylate, an aliphatic polyether urethane oligomer and a trifunctional aliphatic urethane acrylate oligomer
  • the reactive diluent comprising the combination of two or more of hexane diol di(meth)acrylate, dimethyl acrylamide, ethoxyethoxyethyl acrylate and tetrahydrafurfuryl acryalte.
  • the (meth)acrylate type adhesives in the above-mentioned references usually show excellent antifouling performances and peeling performances.
  • none of these references mentions hardness performances of the adhesives after curing and the issue of introducing stress into electric and electronic devices.
  • a photo curable adhesive composition which comprises:
  • component (a) at least one monomer selected from the group consisting of (meth)acrylic acid, (meth)acrylate and (meth)acrylamide;
  • component (d) an oligomer containing no (meth)acryloxy group.
  • This photo curable adhesive composition is the subject matter of our invention.
  • Component (a) is preferably one or more (meth)acrylates; and component (a) is preferably a multifunctional (meth)acrylate monomer, and/or at least one monofunctional (meth)acrylate momomer preferably selected from the group consisting of alkyl (meth)acrylate, alkenyl (meth)acrylate and heterocyclic (meth)acrylate, wherein the alkyl group preferably has 1 to 20 carbon atoms and it can be further substituted, the alkenyl group preferably has 2 to 20 carbon atoms and it can be further substituted, and the heterocyclic group preferably has 2 to 20 carbon atoms and at least one heteroatom selected from nitrogen and oxygen, and it can be further substituted, the substituent preferably being selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an epoxy group, and hydroxy group; and
  • component (a) is preferably a liquid at ambient temperature.
  • Component (b) is preferably at least one antioxidant selected from hindered phenols, diaryl secondary amines, hindered amines and benzotriazoles.
  • Component (b) is also preferably a mixture consisting of a phosphite and at least one antioxidant selected from hindered phenols, diaryl secondary amines, hindered amines and benzotriazoles.
  • Component (c) is preferably at least one selected from the group consisting of benzil ketals, hydroxy ketones, amino ketones and acyl phosphine peroxides.
  • Component (d) is preferably at least one selected from the group consisting of polybutylene, polybutadiene, hydrogenated polybutadiene, polyisoprene, maleinized polyisoprene, terpene resin, and low-molecular weight polymer containing a polyether backbone whose weight average molecular weight preferably is no more than 60000;
  • component (d) is preferably a liquid at ambient temperature.
  • the composition additionally comprises component (e): an oligomer containing a (meth)acryloxy group; preferably polybutadiene containing a (meth)acryloxy group, polyisoprene containing a (meth)acryloxy group, polyurethane containing a (meth)acryloxy group, polyester containing a (meth)acryloxy group, or any combinations thereof; and component (e) is preferably a liquid at ambient temperature.
  • component (e) is preferably a liquid at ambient temperature.
  • the content of each component in the composition is preferably as follows:
  • component (a) 10 to 50 parts by weight of component (a);
  • component (b) 0.05 to 2 parts by weight of component (b);
  • component (c) 0.5 to 10 parts by weight of component (c);
  • the content of each component in the composition is as follows:
  • component (a) 5 to 50 parts by weight of component (a);
  • component (b) 0.05 to 2 parts by weight of component (b);
  • component (c) 0.5 to 10 parts by weight of component (c);
  • the composition is a liquid at ambient temperature, the transmittance of the composition after curing is preferably more than 95%, and the haze of the composition after curing is preferably less than 1 %; and
  • the viscosity of the composition at 25°C is preferably 300 to 5500 mPas, more preferably 500 to 5000 mPas, still more preferably 2000 to 4500 mPas, and most preferably 3000 to 4000 mPas.
  • the viscosity of the composition at 25°C is the Brookfield viscosity measured with a Brookfield RVT DV-II Viscometer (CP52 cone spindle) at 25°C.
  • the shear rate is viscosity-dependent.
  • the hardness of the composition after curing is ShOO 0 to ShOO 70, for example ShOO 10 to ShOO 70; preferably ShOO 0 to ShOO 50, for example ShOO 10 to ShOO 50; and more preferably ShOO 0 to ShOO 40, for example ShOO 20 to ShOO 40.
  • use of the composition is provided for bonding or laminating a transparent substrate with another transparent substrate, or bonding or laminating a transparent substrate with a non-transparent substrate; and
  • the transparent substrate comprises glass and transparent plastic
  • the non-transparent substrate comprises metal, non-transparent plastic, ceramics, stone, leather and wood
  • composition is more preferably used for bonding or laminating glass substrates. This use is a second subject matter of this invention.
  • the adhesive composition comprising component (a) to (d) showed sufficient softness after curing while maintaining an excellent antifouling performance and peeling performance, the stress introduced into electric and electronic devices was lowered, and good anti-aging effect and good viscosity property were also achieved at the same time. Therefore, the final product of the present invention had good optical characteristics and mechanical characteristics.
  • a structural formula, chemical composition and component content of a composition in adhesive field intend to mean a main structure or main ingredient, allowing the presence of permissible deviations.
  • composition refersive composition, “adhesive” and “composition” have the same meaning and can be used to replace each other.
  • Component (a) monomer(s) selected from the group consisting of (meth)acrylic acid,
  • the adhesive composition of the present invention may comprise one or more monomers selected from (meth)acrylic acids, (meth)acrylates and (meth)acrylamides. Since there is a (meth)acryloyl unsaturated group(s) in the molecule of such monomer, the composition containing component (a) can be cured upon photo irradiation. In addition, component (a) can advantageously adjust the viscosity and bonding property of the adhesive composition due to its low viscosity at ambient temperature. The presence of component (a) can also improve the transmittance and storage stability of the adhesive composition.
  • (meth)acryloxy group represents acryloxy, (meth)acryloxy group or their combination;
  • (meth)acrylic acid represents acrylic acid, methacrylic acid or their combination;
  • (meth)acrylate represents acrylate, methacrylate or their combination;
  • (meth)acrylamide” represents acrylamide, methacrylamide or their combination.
  • (meth)acrylate used in the present invention which may be a monofucntional (meth)acrylate or a multifucntional (meth)acrylate.
  • alkyl (meth)acrylates As illustrated examples of the monofunctional (meth)acrylate monomer, alkyl (meth)acrylates, alkenyl (meth)acrylates and heterocyclic (meth)acrylates can be mentioned.
  • the alkyl group may have 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and the alkyl group is optionally substituted.
  • the substitutent may be at least one selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an epoxy group, and a hydroxy group.
  • the alkenyl group may have 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms, and the alkenyl group is optionally substituted.
  • the substitutent may be at least one selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an epoxy group, and a hydroxy group.
  • the heterocyclic group may have 2 to 20 carbon atoms and at least one heteroatom selected from nitrogen and oxygen, and the heterocyclic group is optionally substituted.
  • the substitutent may be at least one selected from an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an epoxy group, and a hydroxy group.
  • monofucntional (meth)acrylate monomer may include but are not limited to methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tetrahydrofuran
  • 2-ethylhexyl acrylate isobornyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isostearyl acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl acrylate 2-phenoxy ethyl acrylate, dicyclopentadienyl methacrylate, ethylene glycol dicyclopentenyl methacrylate, morpholine (meth)acrylate, and caprolactone acrylate etc.
  • Non-limiting examples of multifucntional (meth)acrylate monomer include ethylene glycol dimethacrylate, hexylene glycol di(meth)acrylate, trimethylolpropane trimethacrylate and pentaerythritol tetraacrylate etc.
  • (meth)acrylamide used in the present invention which may be an unsubstituted (meth)acrylamide, an N-alkyl substituted (meth)acrylamide or an
  • the substituted alkyl preferably has 1 to 8 carbon atoms, for example, N-ethyl acrylamide and N-octyl acrylamide etc can be exemplified.
  • the substituted alkyl preferably has 1 to 4 carbon atoms, for example, ⁇ , ⁇ -dimethyl acrylamide and ⁇ , ⁇ -diethyl acrylamide etc can be exemplified.
  • the (meth)acrylate is preferably used in the adhesive composition of the present invention as component (a).
  • the monomer selected from (meth)acrylic acid, (meth)acrylate and (meth)acrylamide is a liquid at ambient temperature.
  • ambient temperature in this context means at about 25°C.
  • the monomer selected from (meth)acrylic acid, (meth)acrylate and (meth)acrylamide may be used alone or in any combinations of two or more.
  • the content of component (a) may be 5 to 50 parts by weight, preferably 10 to 50 parts by weight, more preferably 10 to 45 parts by weight, still more preferably 12 to 40 parts by weight, based on 100 parts by weight of the adhesive composition of the present invention.
  • An antioxidant is used to prevent the adhesive composition from degradation when being brought into contact with oxygen during preparation, handling and application, so as to extend the life of the adhesive composition.
  • the degradation also referred as aging, generally includes deterioration in the appearance, physical property and performance of the adhesive
  • composition such as yellowing phenomenon.
  • the antioxidant used in the present invention may be a primary antioxidant, or a mixture of a primary antioxidant and a secondary antioxidant, with the latter being preferred.
  • the primary antioxidant is used to prevent oxidation of the adhesive composition, while the secondary antioxidant is used to delay oxidation of the adhesive composition.
  • Non-limiting examples of the primary antioxidant include hindered phenols, diaryl secondary amines, hindered amines and benzotriazoles.
  • hindered phenols may be Irganox1010, Irganox1076, Irganox1098, lrganox1135, lrganox245 and BHT etc available from BASF Corporation.
  • Specific examples of the diaryl secondary amines may be Irganox5057 available from BASF Corporation.
  • benzotriazoles may be Tinuvin360 and Tinuvin328 etc available from BASF Corporation.
  • hindered amines may be Tinuvin292, Tinuvin765 and Tinuvin494 etc available from BASF Corporation.
  • Non-limiting examples of the secondary antioxidant used in the present invention include phosphites.
  • Typical examples of the phosphite may be TNPP and Ultranox 626 available from Chemtura Corporation, and HP-10 available from Amfine Chemical Corporation etc.
  • the primary antioxidant may be used alone or in any combinations of two or more.
  • the primary antioxidant is preferably used in combination with the secondary antioxidant so as to enhance the effect of anti-aging.
  • the mixing ratio of the primary antioxidant to secondary antioxidant may be arbitrarily selected according to actual needs.
  • component (b) may be 0.05 to 2 parts by weight, preferably 0.1 to 1.5 parts by weight, more preferably 0.2 to 1.3 parts by weight, based on 100 parts by weight of the adhesive composition of the present invention.
  • a photo polymerization initiator is used to initiate the photo polymerization reaction of component (a) and below-mentioned component (e) (if comprised) so as to cure the adhesive composition.
  • the adhesive composition of the present invention preferably contains a free radical polymerization initiator.
  • Photo polymerization initiator used in the present invention may be benzil ketal, hydroxy ketone, amino ketones and acyl phosphine peroxide etc.
  • Photo polymerization initiator of benzil ketal type may be, for example, commercially available I RGACURE 651 (2,2-dimethoxy-2-phenylacetophenone).
  • Photo polymerization initiator of hydroxy ketone type may be, for example, commercially available Darocure 1173 (HMPP), Darocure 2959 (HHMP) and Darocure 184
  • HCPK (1-hydroxycyclohexyl phenyl ketone, abbreviated as HCPK) etc.
  • Photo polymerization initiator of amino ketone type may be, for example, commercially available Irgacure 907 (2-methyl-1 -[4-(methylthio)phenyl] - 2-(4-morpholinyl)-1 -propanone, abbreviated as MMMP) and Irgacure 369 (BDMB) etc.
  • Irgacure 907 (2-methyl-1 -[4-(methylthio)phenyl] - 2-(4-morpholinyl)-1 -propanone, abbreviated as MMMP
  • BDMB Irgacure 369
  • Photo polymerization initiator of acyl phosphine peroxide type may be, for example,
  • TEPO ethyl (2,4,6-trimethylbenzoyl)phenylphosphinate
  • BAPO phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, abbreviated as BAPO, available from Ciba Specialty Chemicals Inc.
  • the photo polymerization initiator may be used alone or in any combinations of two or more.
  • component (c) may be 0.5 to 10 parts by weight, preferably 0.5 to 5.0 parts by weight, based on 100 parts by weight, based on 100 parts by weight of the adhesive
  • composition of the present invention is a composition of the present invention.
  • Component (d) an oligomer containing no (meth)acryloxy group, is now described according to preferred embodiments:
  • An oligomer containing no (meth)acryloxy group is used to improve or adjust the bonding property of the adhesive composition with substrates.
  • the oligomer containing no (meth)acryloxy group is a liquid at ambient temperature. It doesn't crosslink upon photo irradiation, which helps to adjust the post-curing hardness of the adhesive and provides the adhesive composition with sufficient softness after curing. In addition, the stress generated when laminating and/or bonding the adhesive to the substrate (such as display screen) can also be minimized.
  • oligomer containing no (meth)acryloxy group used in the present invention, so long as it doesn't crosslink upon photo irradiation.
  • Non-limiting examples of the oligomer include polybutylene, polybutadiene, hydrogenated polybutadiene, polyisoprene, maleinized polyisoprene, terpene resin, low-molecular weight polymer containing a polyether backbone, and any combination thereof.
  • the weight average molecular weight (Mw) of the polybutylene is no greater than 5000.
  • the polybutylene include PB-950, PB-1300, PB-1400, PB-2000 and
  • PB-2400 etc available from Daelim Corporation; Indopols L50, H-7, H-8, H-35, H-50, H-100, H-300, H-1200, H-1500, H-1900, H-2100 and H-6000 etc available from BP Corporation; and modified polybutadiene adipate, such as Santicizer 409A etc.
  • the weight average molecular weight (Mw) of the polybutadiene or hydrogenated polybutadiene is no greater than 40000.
  • Illustrated examples of polybutadiene include
  • Non-limiting examples of hydrogenated polybutadiene include GI-1000, GI-2000 and GI-3000 etc. available from Nippon Soda Corporation. Modified polybutadiene is also can be used whose weight average molecular weight (Mw) is preferably no greater than 40000.
  • modified polybutadiene examples include polybutadiene containing a pendant 1 ,2-ethylene structure, available from Degussa Corporation under the tradename Polyoil 110; modified polybutadiene containing an epoxy group, available from Daicel Chemical Corporation under the tradename PB-3600; modified polybutadiene containing a -COOH group, available from Cray Valley Corporation under the tradename PolyBD3000CT.
  • the weight average molecular weight (Mw) of the polyisoprene is no greater than 60000, such as LI R-30 and LIR-50 etc available from Kuraray Corporation.
  • Maleinized polyisoprene also can be used whose weight average molecular weight (Mw) is preferably no greater than 60000, such as LIR-403 and LIR-410 etc available from Kuraray Corporation; Ricon 131 MA8, Ricon 131 MA10, Ricon 131 MA13, Ricon 131 MA20, Ricon131 MA17 and Ricon156MA17 etc available from Cray Valley Corporation.
  • the terpene resins mainly include polymers of the two isomers of terpene: a- terpene or ⁇ - terpene.
  • the weight average molecular weight (Mw) of the terpene resin is preferably no greater than 8000.
  • Illustrated examples of the terpene resin include DERCOLYTE A 10, DERCOLYTE L 115, DERCOLYTE L 120, DERCOLYTE LTG, DERCOLYTE M 105,
  • the low-molecular weight polymer containing a polyether backbone has a weight average molecular weight (Mw) of no greater than 3000, such as Rosin Esters Series available from Eastman Corporation, for example TEG-EH.
  • the oligomer containing no (meth)acryloxy group may be used alone or in any combinations of two or more.
  • the content of component (d) may be 5 to 80 parts by weight, more preferably 30 to 80, still more preferably 40 to 80 parts by weight, and most preferably 40 to 50 parts by weight, based on 100 parts by weight of the adhesive composition of the present invention.
  • the adhesive composition of the present invention may optionally comprise an oligomer containing a (meth)acryloxy group.
  • the oligomer may self-crosslink or crosslink with component (a) of the composition upon photo irradiation due to the presence of the (meth)acryloxy unsaturated group in its molecule, which in turn promotes the photo curing speed of the whole adhesive composition and imparts rapid curing property to the adhesive composition.
  • the presence of the oligomer having curing activity can also improve the viscosity, bonding property and storage stability of the adhesive composition.
  • (meth)acryloxy group may be at any position in the oligomer molecule , preferably at the end of the backbone and/or in the side chain.
  • oligomer containing a (meth)acryloxy group is polybutadiene containing a
  • (meth)acryloxy group polyisoprene containing a (meth)acryloxy group, such as UC-203 and UC-102 etc available from Kuraray Corporation; polyurethane containing a (meth)acryloxy group, such as CN962, CN964, CN965, CN934 and CN972 available from Sartomer
  • (meth)acryloxy group such as CN292, CN2200, CN9021 and CN2255 available from Sartomer Corporation; or any combinations thereof. All these listed oligomers are commercially available from Sartomer Corporation and/or Kuraray Corporation.
  • (meth)acryloxy group brominated butyl rubber (brominated isobutylene-isoprene copolymer) containing a (meth)acryloxy group, chlorinated butyl rubber (chlorinated isobutylene-isoprene copolymer) containing a (meth)acryloxy group, and any combinations thereof.
  • the species corresponding to the above-listed oligomers which don't contain a (meth)acryloxy group are commercially available, and since they have reactive groups such as hydroxy group in their molecules, they can react with (meth)acrylates to obtain the oligomers containing a
  • the oligomer containing a (meth)acryloxy group of the present invention is a liquid at ambient temperature.
  • the oligomer containing a (meth)acryloxy group of the present invention has a Tg of from about -100°C to 20°C.
  • the average functionality of acryloxyl of the oligomer containing a (meth)acryloxy group is greater than 0 but less than or equal to 3, preferably greater than 0.5 but less than or equal to 3.
  • the term "average functionality" means an average number of the (meth)acryloxy group per molecule.
  • oligomer containing a (meth)acryloxy group may be used alone or in any combinations of two or more.
  • the content of optional component (e) may be 0 to 80 parts by weight, more preferably 30 to 80 parts by weight, still more preferably 30 to 65 parts by weight, and most preferably 30 to 50 parts by weight, based on 100 parts by weight of the adhesive composition of the present invention.
  • the adhesive composition of the present invention may also comprise various additives other than the above-mentioned components (a) to (e), when necessary.
  • additives and their contents are common-known in the adhesive field.
  • the additive include sensitizer, radical scavenger, wetting agent, leveling agent, colorant, and other adhesive promoter which can improve the property, such as viscosity, adhesion strength or flexibility of the composition.
  • the adhesive composition of the present invention is preferably a liquid.
  • the good flowing property of the liquid adhesive composition makes it easy to be coated or injected onto a substrate.
  • the adhesive composition of the present invention has a clear appearance, and maintains the clear appearance and excellent optical properties, for example, a transmittance of greater than 95% and even greater than 99%; and a haze of preferably less than 1 % and even less than 0.5% after being photo-irradiated.
  • the visible light transmittance of the adhesive composition after curing is the visible light transmittance of the adhesive composition after curing.
  • the adhesive composition of the present invention comprises component (d): an oligomer not containing a (meth)acryloxy group, which imparts sufficient softness to the composition after curing, and a post-curing hardness as low as ShOO 10 can be achieved.
  • any appropriate sequence and any appropriate method may be applied to mix components (a) to (d) and any other optional component.
  • Mixing can be carried out continuously or intermittently, with or without stirring.
  • the stirring speeds in different stages may be the same or different, for example the stirring speed in a previous stage may be set as from about 50 to 80 rpm, and the stirring speed in a latter stage may be set as from about 80 to 150 rpm.
  • the addition of the photo polymerization initiator and subsequent mixing and storage should be carried out under weak luminescence condition, preferably avoiding light. It is advantageous to mix other components prior to mixing the photo polymerization initiator with the components which are photo polymerization active.
  • the temperature and time period for mixing may be arbitrarily set according to actual needs.
  • the adhesive composition of the present invention may be used for bonding or laminating electric and electronic elements, especially various elements in display devices.
  • the adhesive composition of the present invention is particularly suitable for bonding or laminating a transparent substrate with another transparent substrate, or bonding or laminating a
  • the transparent substrate includes glass, and transparent plastic etc
  • the non-transparent substrate includes metal, non-transparent plastic, ceramic, stone, leather, and wood etc.
  • Plastic may be for example poly(methyl methacrylate) (PMMA), polycarbonate (PC) or polyester (PET).
  • PMMA poly(methyl methacrylate)
  • PC polycarbonate
  • PET polyester
  • the adhesive composition of the present invention may be applied between substrates by coating or injecting.
  • Conventional coating methods can be used herein, for example slit coating, spray coating, spin coating, roll coating and cast coating etc.
  • the coating thickness of the composition may be selected according to actual needs.
  • the coating thickness is preferably as small as possible, for example from about 50 to about 200 ⁇ " ⁇ , preferably from about 100 to about 150 ⁇ - ⁇ .
  • the above-mentioned adhesive composition can be cured by photo-irradiation.
  • Light source such as ultraviolet light and visible light
  • high energy ray such as electronic beam, a-ray, ⁇ -ray and X-ray
  • the energy dose is preferably 3000mJ/cm 2 or more
  • the power density is preferably about 100mW/cm 2
  • the irradiation time is preferably 30 seconds or more.
  • the method of bonding substrates by using the adhesive composition of the present invention is preferably as follows: applying the adhesive composition between substrates, followed by photo irradiation as mentioned above.
  • the adhesive composition of the present invention exhibits excellent antifouling performance and peeling performance, and the reason lies in that there is the monomer selected from (meth)acrylic acid, (meth)acrylates and (meth)acrylamides in the composition, and the oligomer containing a (meth)acryloxy group is optionally present therein.
  • the adhesive composition of the present invention when compared with conventional pressure sensitive adhesive tape, is in liquid state which makes it more widely used with a better adhesive strength, for example, uneven surfaces can be bonded with the adhesive composition of the present invention.
  • the adhesive composition of the present invention provides sufficient softness after curing and is capable of lowering the stress introduced into electric and electronic devices, while maintaining a sufficiently high transmittance and preventing yellowing during storage, which improves the overall property of the final product. Examples
  • UC-203 polyisoprene containing a (meth)acryloxy group, available from Kuraray Corporation, functionality being about 3, and weight average molecular weight being about 33000;
  • UC-102 polyisoprene containing a (meth)acryloxy group, available from Kuraray Corporation, functionality being about 2, and weight average molecular weight being about 17000;
  • BR3641 AA polyurethane containing a (meth)acryloxy group, available from Bomar Corporation, Tg being about -49°C, and functionality being about 1.5;
  • CN9021 polyester containing a (meth)acryloxy group, available from Sartomer Corporation, functionality being about 2, Tg being about -54°C, and viscosity being 5000 mPa.s/65°C;
  • LIR-403 maleinized polyisoprene, available from Kuraray Corporation;
  • Polyoil 110 polybutadiene containing a pendant 1 ,2-ethylene structure, available from Degussa
  • PB-3600 modified polybutadiene containing an epoxy group, available from Daicel Chemical
  • viscosity being about 45000 mPa- s/45°C;
  • PolyBD3000CT modified polybutadiene containing a -COOH group, available from Cray Valley Corporation, weight average molecular weight being about 3300;
  • GI-1000 hydrogenated polybutadiene, available from Nippon Soda Corporation, weight average molecular weight being about 1500;
  • LIR-30 polyisoprene, available from Kuraray Corporation, Tg being about -63°C, viscosity being 70000 mPa- s /38°C, and Mw being about 30000;
  • Ricon130 polybutadiene, available from Sartomer Corporation, Mw being about 8000, and viscosity being 1500 mPa- s /38°C;
  • Irganox 1010 hindered phenol, available from BASF Corporation
  • BHT butylated hydroxytoluene, available from BASF Corporation
  • Irganox 1135 hindered phenol, available from BASF Corporation;
  • Tinuvin292 hindered amine , available from BASF Corporation;
  • Tinuvin765 hindered amine , available from BASF Corporation;
  • Darocure 184 1-hydroxycyclohexyl phenyl ketone, available from Ciba Specialty Chemicals Inc.;
  • Irgacure 819 phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, available from Ciba Specialty Chemicals Inc.;
  • TPO a photo polymerization initiator, available from Ciba Specialty Chemicals Inc.. Test methods
  • the adhesive composition of the present invention was subjected to viscosity test at room temperature according to ASTM D1084.
  • viscosity means Brookfield viscosity herein.
  • the viscosity of the adhesive composition is measured using Brookfield Viscometer (dynamic, RVT DV-II CP52, at 25 ° C ).
  • the shear rate is viscosity-dependent:
  • a polyvinyl chloride) film (uniform thickness: 0.18mm) was placed on a glass plate of
  • the resultant sample was sufficiently cured under violet light for about 2 minutes (with each surface being cured for 1 minute, and the power density being 100mW/cm 2 ).
  • Three pieces of the cured film of the same size were cut off from the resultant sample for the hardness test.
  • the total hardness of the three pieces was measured by using a hardness tester and take the average hardness for the 6mm film according to ASTM D2240.
  • the adhesive composition of the present invention was slightly stressed to flow to form a circle shape, which is sufficiently cured for 1 minute (UVA power density: 100mW/cm 2 ).
  • UVA power density 100mW/cm 2
  • the visible light transmittance of the adhesive composition after curing was tested by using a spectrophotometer (Cary-300, available from Varian, America) according to ASTM E903.
  • the adhesive composition of the present invention was slightly stressed to flow to form a circle shape, which is sufficiently cured for 1 minute (UVA power density: 100mW/cm 2 ).
  • the b * value (also referred to as the yellowing index) of the adhesive composition after curing was tested by using a spectrophotometer (Cary-300, available from Varian, America) according to ASTM D1003-2007.
  • the formulation of the adhesive composition was as follows:
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation. 20 parts by weight of lauryl
  • component (b) 0.1 parts by weight of Tinuvin765 component (c) 1 .9 parts by weight of Darocure
  • component (e) 29 parts by weight of CN9021
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation.
  • the difference mainly lies in that the adhesive composition in Comparative Example 1 doesn't contain component (a). component 0.1 parts by weight of Irganox
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation. The difference mainly lies in that adhesive composition in Comparative Example 1 doesn't contain component (b).
  • the adhesive composition was prepared in the same manner as described in Example 1 , except employing the following adhesive composition formulation. The difference mainly lies in that adhesive composition in Comparative Example 1 doesn't contain component (d).
  • the adhesive compositions obtained in Example 1 to 7 exhibited excellent viscosities, low hardness values, good transmittances, good anti-aging performances and excellent storage stabilities.
  • the adhesive composition in Comparative Example 1 didn't contain (meth)acrylate monomer and showed a transmittance of less than 90% which was apparently decreased.
  • the adhesive composition in Comparative Example 2 didn't contain component (b), the yellowing index (b * ) after aging for 120 hours at 90°C was greater than 1 , obvious yellowing was observed at the edges of the bonded glass plates, and storage stability was inferior.
  • the adhesive composition in Comparative Example 3 didn't contain component (d), the hardness after curing was greater than ShOO 70, the flexibility was inferior, and cleavage was observed when being used to bonding glass plates.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention concerne une composition adhésive photodurcissable, comprenant un composant (a) : au moins un monomère choisi dans le groupe composé d'acide (méth)acrylique, d'acide (méth)acrylate et de (méth)acrylamide ; un composant (b): un antioxydant ; un composant (c) : un photoinitiateur de polymérisation ; et un composant (d) : un oligomère ne contenant aucun groupe (méth)acryloxy. La composition de la présente invention est utilisée pour lier ou stratifier un substrat transparent avec un autre substrat transparent, ou pour lier ou stratifier un substrat transparent avec un substrat non-transparent.
PCT/CN2012/078238 2011-07-25 2012-07-05 Compositions adhésives photodurcissables et utilisations associées WO2013013568A1 (fr)

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WO2016126130A1 (fr) * 2015-02-04 2016-08-11 주식회사 엘지화학 Composition adhésive
CN106189939A (zh) * 2015-04-10 2016-12-07 博威电子股份有限公司 光学胶组成物、光学胶膜以及光学积层板
WO2017005992A1 (fr) * 2015-07-06 2017-01-12 Bluestar Silicones France Sas Article multicouche auto-adhésif et son procédé de préparation
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KR102050177B1 (ko) * 2015-07-06 2019-11-28 엘켐 실리콘즈 프랑스 에스에이에스 자가접착성 멀티레이어 아이템 및 이의 제조 방법
KR20180028481A (ko) * 2015-07-06 2018-03-16 블루스타 실리콘즈 프랑스 에스에이에스 자가접착성 멀티레이어 아이템 및 이의 제조 방법
KR20180029029A (ko) * 2015-07-10 2018-03-19 아르끄마 프랑스 단관능성 아크릴레이트를 포함하는 경화성 조성물
WO2017009184A1 (fr) * 2015-07-10 2017-01-19 Arkema France Compositions durcissables comportant des acrylates monofonctionnels
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US11028204B2 (en) 2015-07-10 2021-06-08 Arkema France Curable compositions comprising mono-functional acrylates
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JP2019182929A (ja) * 2018-04-03 2019-10-24 王子ホールディングス株式会社 粘着剤組成物、粘着シート及び積層体
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