WO2019169595A1 - Composition adhésive photodurcissable - Google Patents

Composition adhésive photodurcissable Download PDF

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Publication number
WO2019169595A1
WO2019169595A1 PCT/CN2018/078397 CN2018078397W WO2019169595A1 WO 2019169595 A1 WO2019169595 A1 WO 2019169595A1 CN 2018078397 W CN2018078397 W CN 2018078397W WO 2019169595 A1 WO2019169595 A1 WO 2019169595A1
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WO
WIPO (PCT)
Prior art keywords
adhesive composition
meth
photocurable adhesive
acrylate
acrylate monomer
Prior art date
Application number
PCT/CN2018/078397
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English (en)
Inventor
Chunyu Sun
Cheng Lu
Chunhua GU
Original Assignee
Henkel Ag & Co. Kgaa
Henkel (China) Co., Ltd.
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Priority to PCT/CN2018/078397 priority Critical patent/WO2019169595A1/fr
Publication of WO2019169595A1 publication Critical patent/WO2019169595A1/fr

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    • 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
    • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2244—Oxides; Hydroxides of metals of zirconium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/011—Nanostructured additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • This invention relates to a photocurable adhesive composition for assembling optical electronic devices.
  • the present invention relates to a photocurable adhesive composition offering a good flexibility and excellent optical properties when cured.
  • Photocurable optically clear adhesives (OCAs) and especially LOCAs are finding wide applications in optical bonding for optical electronic devices, such as optical displays.
  • Typical applications of such adhesives include, for example, adhering a touch panel onto a display and adhering ITO glass of a touch panel to an exterior film or glass.
  • ITO glass usually used in the touch panel has a refractive index up to 1.8. If the refractive index of LOCAs does not match that of ITO glass (up to 1.8) or sapphire glass (up to 1.77) , the light reflection of the optical displays will be increased and the contrast and brightness will be decreased.
  • a common LOCA such as (meth) acrylate adhesive, has a refractive index of about 1.4 to 1.45, which cannot meet current industry standards.
  • LOCAs when used in touch panels, they must have the appropriate flexibility so as to provide excellent cushioning properties and to avoid undesirable visual effects such as water ripple appearing in the touch panels due to stress.
  • US 9850329 B2 discloses a LOCA compositions comprising a low viscosity polymer derived from farnesene. Such compositions possess a low viscosity and a refractive index about 1.5 when cured.
  • JP 5713155 B1 discloses a photocurable optical adhesive composition
  • a photocurable optical adhesive composition comprising a urethane acrylate, a monofunctional (meth) acrylate monomer, an alkylene glycol dibenzoate as plasticizer and a photoinitiator.
  • Such composition can be cured into a cured article having excellent flexibility and a refractive index of about 1.5.
  • CN 105542703 A discloses a LOCA composition for touch screen, comprising a urethane acrylate, a modified acrylate, a reactive diluent, an additive, and photoinitiator. Such composition is reported to have a refractive index of about 1.52 when cured.
  • US 20160215175 A1 disclose a high-refractive adhesive film for touch panel, comprising a thermosetting resin matrix and high refractive particles dispersed in the resin matrix, in which the refractive index of the adhesive film is from 1.49 to 1.56.
  • the present invention provides photocurable adhesive compositions which overcome the abovementioned disadvantage of present LOCAs.
  • the photocurable adhesive compositions in this invention could significantly reduce the light reflection when cured.
  • the photocurable adhesive composition in this invention is optically clear when cured.
  • the photocurable adhesive composition in this invention is optically clear when cured and exhibited excellent optical properties after aging.
  • the photocurable adhesive composition in this invention is flexible when cured Besides, the application of the photocurable adhesive composition is simple and suitable for industrial production.
  • the present invention in general, provides a photocurable adhesive composition, comprising,
  • the first (meth) acrylate monomer has a glass transition temperature higher than 0 °C
  • the second (meth) acrylate monomer is a linear alkyl (meth) acrylate having a glass transition temperature of 0 °C or lower
  • the inorganic nanoparticles has refractive index of from 1.7 to 4.5.
  • the present invention also provides a cured film of the photocurable adhesive composition according to the present invention, which is optically clear.
  • the present invention also provides the use of the photocurable adhesive composition and the cured film in assembling electronic devices.
  • Figure 1 illustrates the test method of flexibility of the cured film obtained by the photocurable adhesive composition.
  • the photocurable adhesive composition comprises a first (meth) acrylate monomer having a glass transition temperature (Tg) higher than 0 °C, preferably from 5 °C to 150 °C, more preferably from 10 °C to 120 °C, and in particular from 20 °C to 110 °C.
  • the first (meth) acrylate monomer may be a monofunctional or difunctional (meth) acrylate monomer, and preferably is a monofunctional (meth) acrylate monomer.
  • a monomer having a Tg refers to a monomer that, when in homopolymer form, displays a glass transition temperature as specified. Glass transition temperature may be measured, for example, by differential scanning calorimetry (DSC) .
  • DSC differential scanning calorimetry
  • (meth) acrylate should be understood as methacrylate and acrylate both.
  • Examples of the first (meth) acrylate monomer having Tg higher than 0 °C include but not limited to methyl acrylate (Tg 10 °C) , n-butyl methacrylate (Tg 20 °C) , tert-butyl acrylate (Tg 43-107 °C) , hexyl acrylate (Tg 57 °C) , isobornyl acrylate (Tg 94 °C) , methyl methacrylate (Tg 105-120 °C) , ethyl methacrylate (Tg 65 °C) , isopropyl methacrylate (Tg 81 °C) , isobutyl methacrylate (Tg 53 °C) , t-butyl methacrylate (Tg 118 °C) , hexadecyl methacrylate (Tg 15 °C) , cyclohexyl methacrylate
  • the first (meth) acrylate monomer is selected from isobornyl acrylate, isobornyl methacrylate, benzyl acrylate, benzyl methacrylate, and mixture thereof.
  • the first (meth) acrylate monomer is present in an amount of 1%to 20%, preferably 5%to 15%by weight based on the total weight of the photocurable adhesive composition.
  • the photocurable adhesive composition comprises a second (meth) acrylate monomer which is a linear alkyl (meth) acrylate having a glass transition temperature (Tg) of 0 °C or lower, preferably from -100 °C to 1 °C, more preferably from -70 °Cto -3 °C, and in particular from -65 °C to -3 °C.
  • Tg glass transition temperature
  • the linear alkyl (meth) acrylate contains 1 to 20, preferably 2 to 16, and more preferably 4 to 12, carbon atoms in the linear alkyl moiety.
  • the linear alkyl (meth) acrylate may be optionally substituted by halogen, hydroxy, cyano, carboxy groups, and the like.
  • Examples of the second (meth) acrylate monomer having Tg of 0 °C or lower include but not limited to ethyl acrylate (Tg -24 °C) , n-butyl acrylate (Tg -54 °C) , n-dodecyl acrylate (Tg -3 °C) , 2, 2, 2-trifluoroethyl acrylate (Tg -10 °C) , n-hexyl methacrylate (Tg -5 °C) , n-octyl methacrylate (Tg -20 °C) , n-dodecyl methacrylate (Tg -65 °C) , n-octadecyl methacrylate (Tg -100 °C) , 4-hydroxy-n-butyl acrylate (Tg -40 °C) . Two or more of the second (meth) acrylate monomer may be used
  • the second (meth) acrylate monomer is selected from n-butyl acrylate, n-butyl methacrylate, n-dodecyl acrylate, n-dodecyl methacrylate and mixture thereof.
  • the second (meth) acrylate monomer is present in an amount of 0.5%to 10%, preferably 1%to 5%by weight based on the total weight of the photocurable adhesive composition.
  • first (meth) acrylate monomer and second (meth) acrylate monomer can be found in US 20130287980 A1, the whole content of which is incorporated herein by reference.
  • the second (meth) acrylate monomer having a lower Tg contributes to the flexibility of the adhesive composition when cured, and meanwhile the linear alkyl chain structure of the second (meth) acrylate monomer maintains the excellent optical properties of the cured products.
  • the photocurable adhesive composition further contains a plurality of inorganic nanoparticles as filler.
  • the inorganic nanoparticles have refractive index of from 1.7 to 4.5, preferably 1.7 to 2.5.
  • the refractive index may be measured by using a Metricon Model 2010/M prism coupler refractometer.
  • the size of such nanoparticles is chosen to avoid significant visible light scattering. It may be desirable to employ a mixture of inorganic particle types to optimize an optical or material property and to lower total composition cost.
  • the nanoparticles can be oxide particles having a (e.g. unassociated) primary particle size or associated particle size of greater than 1 nm, 5 nm or 10 nm.
  • the primary or associated particle size is generally less than 100 nm, 75 nm, or 50 nm. Typically, the primary or associated particle size is less than 40 nm, 30 nm, or 20 nm. It is preferred that the nanoparticles are unassociated.
  • the primary particle size of the nanoparticles is in the range of 1 nm to 50 nm, preferably 5 nm to 40 nm, so as to achieve excellent transparency and good cost-effectiveness at same time.
  • Their measurements can be based on transmission electron microscopy (TEM) .
  • inorganic nanoparticles can include but not limited to metal oxides such as ZrO 2 , TiO 2 , Al 2 O 3 , Sb 2 O 4 (or Sb 2 O 3 , Sb 2 O 5 ) , CdO, CaO 2 , Cu 2 O, FeO, Fe 2 O 3 , PbO, MnO, MnO 3 , SnO 2 , ZnO, ZnS, ZnSe, ZnTe and mixtures thereof.
  • the inorganic nanoparticles include ZrO 2 , TiO 2 , Al 2 O 3 , and mixture thereof.
  • the nanoparticles of metal oxides can be substantially fully condensed.
  • Fully condensed inorganic nanoparticles typically have a degree of crystallinity (measured as isolated metal oxide particles) greater than 55%, preferably greater than 60%, and more preferably greater than 70%.
  • the degree of crystallinity can range up to about 86%or greater.
  • the degree of crystallinity can be determined by X-ray diffraction techniques.
  • Condensed crystalline (e.g. zirconia) inorganic nanoparticles have a high refractive index whereas amorphous inorganic nanoparticles typically have a lower refractive index.
  • the inorganic nanoparticles such as ZrO 2 nanoparticles may be optionally surface modified, and preferably are surface modified with one or more organic modifier to adjust the refractive index of the nanoparticles.
  • organic treating agents are such as (meth) acrylate functionized compounds as disclosed in WO 2010074862 A1, cumylphenol derivatives as disclosed in PCT/CN2017/091051, and carboxylic acids or (meth) acrylic acids having an ester group as disclosed in JP 6251478 B2.
  • the surface modification of the inorganic nanoparticles may be dispersed in advance, and can be accomplished in a variety of ways.
  • the dispersing process generally involves the mixture of an inorganic particle dispersion with surface modifier (s) .
  • a solvent for example, toluene, methanol, 1-methoxy-2-propanol, ethanol, isopropanol, ethylene glycol, N, N-dimethylacetamide and 1-methyl-2-pyrrolidinone can be added in the dispersion.
  • the solvent can enhance the solubility of the surface modified particles in the surface modifier.
  • the mixed dispersion comprising the inorganic nanoparticles and surface modifier can be subsequently treated at room or an elevated temperature, with or without mixing.
  • ZrO 2 nanoparticles for use in adhesive composition of the invention are available from Sakai Chemical under the trade name “SZR” and Nippon Shukubai under the trade name of “AX-ZP” .
  • the inorganic nanoparticles can be present in a photocurable adhesive composition in an amount of 50%to 95%, preferably 60%to 90%by weight based on the total weight of the photocurable adhesive composition.
  • the photocurable adhesive composition further comprises a photoinitiator to initiate the radiation curing, preferably UV curing of the composition upon receiving sufficient UV radiation.
  • Suitable photoinitiators include, but are not limited to, organic peroxides, azo compounds, quinones, benzophenones, nitroso compounds, acryl halides, hydrazones, mercapto compounds, pyrylium compounds, triacrylimidazoles, bisimidazoles, chloroalkyltriazines, benzoin ethers, benzil ketals, thioxanthones, acetophenones, acylphosphine oxides, alpha hydroxyl ketones, alpha amino ketones, derivatives of the aforementioned compounds, and mixtures thereof.
  • Exemplary photoinitiators are benzil ketals such as 2, 2-dimethoxy-2-phenyl acetophenone (available from Ciba Specialty Chemicals under the trademark Irgacure 651) ; acetophenone derivatives such as 2, 2-diethoxyacetophenone ( "DEAP” , available from First Chemical Corporation) ; 2-hydroxy-2-methyl-1-phenyl-propan-1-one ( "HMPP” , available from Ciba Specialty Chemicals under the trademark Darocur 1173) ; 1-hydroxy-cyclohexyl-phenyl ketone (available from Ciba Specialty Chemicals under the name Irgacure 184) ; 2-benzyl-2-N, N-dimethylamino-1- (4-morpholinophenyl) -1-butanone (available from Ciba Specialty Chemicals under the trademark Irgacure 369) ; 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan
  • the photoinitiator useful in the present invention is selected from the group consisting of 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis (2, 4, 6-trimethylbenzoyfl) -phenylphosphine oxide, 1-hydroxy-cyclohexyl-phenyl ketone, 2, 4, 6-trimethylbenzoyl diphenylphosphine oxide, and the combination thereof. More preferably, the photoinitiator is 1-hydroxy-cyclohexyl-phenyl ketone.
  • the photoinitiator is present in an amount of 0.005 to 0.5%, preferably 0.01%to 0.1%by weight based on the total weight of the photocurable adhesive composition.
  • the content photoinitiator is less than 0.005%by weight of the total weight of the composition, the polymerization reaction is not complete, which leads to problems with mechanical and optical properties.
  • composition contains an excess of photoinitiator, and unreacted photoinitiator have negative effect on the composition, mainly aging and turning the cured product yellow.
  • the photocurable adhesive compositions described herein may further comprise one or more flow additives, adhesion promoters, rheology modifiers, toughening agents, fluxing agents, film flexibilizers, UV stabilizers, curing agents, diluents and the like, as well as mixtures of any two or more thereof, as long as the optical properties, flexibility and other advantages achieved by the adhesive composition are not negatively influenced.
  • the photocurable adhesive composition according to the present invention can be prepared by mixing all components together to gain homogenous mixture.
  • the mixing can be done at room temperature.
  • the mixing device can be for example orbital-motion (planetary) mixer, or compulsory mixer.
  • the photocurable adhesive composition of the present invention is in the form of liquid, and the Brookfield viscosity of the composition is preferably about 50 cPs to about 40,000 cPs at 25 °C.
  • the liquid adhesive composition in such range of viscosity has a good flowing property which makes it easy to be applied or injected onto a substrate.
  • Another aspect of the present invention provides a process of bonding substrates, comprising,
  • the adhesive composition according to the present invention may be coated under pressure onto the surface of the substrate following the predetermined route by means of the needle cylinder of an automatic dispensing system. Subsequently, another substrate is laminated onto the adhesive, and the height difference between the two substrates is controlled by a dispenser. After the adhesive is self-leveled on the whole bonding area, photo irradiation is conducted from top to bottom for curing.
  • Light source such as ultraviolet light and visible light
  • high energy ray such as electronic beam, alpha-ray, gamma-ray and X-ray
  • photo irradiation can be used herein for photo irradiation, with preference given to ultraviolet light in the wavelength range of about 200 nm to about 400 nm.
  • the energy dose is 3000 mJ/cm 2 or more, the power intensity is about 50 to about 100 mW/cm 2 .
  • the UV lamp used may be such as Loctite UVALOC 1000, and the irradiation time may generally be about 5 s to about 120 s.
  • the present invention also provides the cured product, preferably cured film of the photocurable adhesive composition.
  • the cured film is optically clear, and has a b*value no larger than 1.0 and a haze value less than 0.5%, in initial and even after aging.
  • the cured film also has a refractive index of 1.50 or more measured by using a Metricon Model 2010/M prism coupler refractometer.
  • the cured film has a thickness of 50 ⁇ m to 500 ⁇ m, preferably 100 ⁇ m to 300 ⁇ m.
  • the cured film is intact when the end of the cured film is bended at 120 ° relative to the cured film surface for 30 sec.
  • the term “intact” used herein means no indications of breaking or cracking can be visually found on the surface of the cured film.
  • the photocurable adhesive composition of the present invention after being cured, exhibits good light transmittance and high refractive index.
  • the adhesive composition of the present invention has appropriate softness and is useful in optical electronic devices, especially in displays or touch panels, as an adhesive or liquid optically clear adhesive (LOCA) for providing cushioning properties and improving the visually aesthetic appearance of screens.
  • LOCA liquid optically clear adhesive
  • the adhesive composition of the present invention has appropriate flowability, is easy to be coated and adhered. Therefore, it can be used in handheld device and display (HHDD) , especially for bonding or laminating various elements in the manufacture of displays or touch panels, in place of optical adhesive tapes, to simplify the manufacture process and improve the yield of the process.
  • the photocurable adhesive composition of the present invention can be used in bonding or laminating a transparent substrate with another transparent substrate, or bonding or laminating a transparent substrate with a non-transparent substrate.
  • the transparent substrate comprises glass and transparent plastic etc.
  • the non-transparent substrate comprises metal, non-transparent plastic, ceramic, stone, leather and wood etc.
  • Plastic may be for example poly (methyl methacrylate) (PMMA) , polycarbonate (PC) or polyester (PET) etc.
  • Benzyl methacrylate is commercially available from Aldrich.
  • Lauryl acrylate is commercially available from BASF under the tradename of LA1214.
  • ZrO 2 nanoparticles is commercially available from Nippon Shokubai under the tradename of AX-ZP-159-A (about 70%surface modified ZrO 2 nanoparticles dispersed in methyl ethyl ketone) .
  • 1-hydroxy-cyclohexyl-phenyl ketone is commercially available from BASF under the tradename of Irgacure 184.
  • Isobornyl acrylate is commercially available from TCI.
  • Lauryl methacrylate is commercially available from Energy.
  • n-Butyl acrylate is commercially available from Aldrich.
  • 4-Hydroxy-n-butyl acrylate is commercially available from BASF under the tradename of 4-HBA.
  • Branched C17 ester of acrylic acid is commercially available from BASF.
  • Isodecyl acrylate is commercially available from BASF under the tradename of IDA.
  • 2-Ethylhexyl methacrylate is commercially available from TCI.
  • Example 2 was prepared in the same way as Example 1, except that 11.50 g isobornyl acrylate and 1.80 g lauryl acrylate were added to a mixer and stirred for 10 min. The solvent in the nanoparticle dispersion was removed by rotatory evaporator.
  • Example 3 was prepared in the same way as Example 1, except that lauryl methacrylate was used instead of lauryl acrylate.
  • Example 4 was prepared in the same way as Example 1, except that 11.55 g benzyl methacrylate and 1.80 g n-butyl acrylate were used instead of 10.11 g benzyl methacrylate and 3.24 g lauryl acrylate.
  • Example 5 was prepared in the same way as Example 1, except that 4-hydroxy-n-butyl acrylate were used instead of lauryl acrylate.
  • Comparative Example 1 was prepared in the same way as Example 1, except that 8.79 g benzyl methacrylate, 87.89 g 159-A, 1.46 g branched C17 ester of acrylic acid and 1.83 g isodecyl acrylate were used instead of 10.11 g benzyl methacrylate, 86.62 g 159-A and 3.24 g lauryl acrylate.
  • Comparative Example 2 was prepared in the same way as Example 1, except that 2-ethylhexyl acrylate were used instead of lauryl acrylate.
  • Comparative Example 3 was prepared in the same way as Example 1, except that 2-ethylhexyl methacrylate were used instead of lauryl acrylate.
  • each formulated adhesive composition in the examples was placed on a gorilla glass. 127 ⁇ m spacers were placed either end of the glass and the other glass was placed over the sample supported by the spacers to afford an approximate bonding gap of 127 ⁇ m.
  • Each adhesive composition was cured under UVALOC 1000 with 500W for 25 seconds.
  • the test sheets were then exposed in a QUV test apparatus (QUV accelerated weathering tester, made by Q-Panel Company, Cleveland, Ohio, USA) for 500 hours. The following methods were used to evaluate the examples.
  • the refractive indexes of the cured films were measured by using a Metricon Model 2010/M prism coupler refractometer.
  • Brookfield viscosity was measured by using a Brookfield rotational viscometer (digital Brookfield viscometer, DV-II+, available from BROOKFIELD, US) with spindles at 25 °Caccording to ASTM D1084-1997.
  • the initial and QUV aged optical properties typically transmittance, haze and the b* value (yellowness) were measured by a Datacolor 650 apparatus available from Datacolor Corporation, in compliance with ASTM D1003.
  • the flexibility of the cured film was measured by subjecting the end of cured film having thickness of about 250 ⁇ m to bending at 120 ° relative to the original film surface for 30 sec as shown in Fig. 1. If the surface of the cured film was intact, i.e. showing no breaks and/or no cracks, it would be marked as “Pass” . If any breaks or cracks was visually found, it would be marked as “Fail” .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition adhésive photodurcissable pour assembler des dispositifs électroniques optiques, qui offre une bonne flexibilité et d'excellentes propriétés optiques lorsqu'elle est durcie.
PCT/CN2018/078397 2018-03-08 2018-03-08 Composition adhésive photodurcissable WO2019169595A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114423731A (zh) * 2019-09-26 2022-04-29 汉高股份有限及两合公司 生物基丙烯酸酯单体
WO2024034859A1 (fr) * 2022-08-09 2024-02-15 삼성에스디아이 주식회사 Film adhésif, élément optique le comprenant et dispositif d'affichage optique le comprenant

Citations (6)

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