WO2018088461A1 - Inkjet ink composition - Google Patents

Inkjet ink composition Download PDF

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Publication number
WO2018088461A1
WO2018088461A1 PCT/JP2017/040371 JP2017040371W WO2018088461A1 WO 2018088461 A1 WO2018088461 A1 WO 2018088461A1 JP 2017040371 W JP2017040371 W JP 2017040371W WO 2018088461 A1 WO2018088461 A1 WO 2018088461A1
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WO
WIPO (PCT)
Prior art keywords
meth
acrylate
ink composition
inkjet ink
active energy
Prior art date
Application number
PCT/JP2017/040371
Other languages
French (fr)
Japanese (ja)
Inventor
正和 吉澤
伸生 小林
崇倫 青木
Original Assignee
Dic株式会社
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Publication date
Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to JP2018515158A priority Critical patent/JP6365917B1/en
Publication of WO2018088461A1 publication Critical patent/WO2018088461A1/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses

Definitions

  • the present invention relates to an inkjet ink composition used for an optical article and a cured product obtained by curing the composition.
  • an ink-jet ink composition used for forming an optical member of an image display device by an ink-jet method for example, a low-viscosity photo-curable ink-jet ink containing fluorene-based (meth) acrylate and a specific diluent is disclosed.
  • a low-viscosity photo-curable ink-jet ink containing fluorene-based (meth) acrylate and a specific diluent is disclosed.
  • a specific diluent for example, refer to Patent Document 2.
  • the image display device since the image display device is used in various environments depending on applications, it has been required to realize high adhesion not only in a normal state but also in a humid heat environment.
  • An object of the present invention is to provide an ink-jet ink composition having a high refractive index and excellent wet heat adhesion while being applicable to ink-jet.
  • R 1 is a hydrogen atom or a methyl group.
  • R 2 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom.
  • N 1 and n 2 are 1 Represents 4) Containing a monofunctional (meth) acrylate compound represented by By the inkjet ink composition in which the content of the monofunctional (meth) acrylate compound represented by the formula (1) in the active energy ray-curable compound (A) contained in the inkjet ink composition is 60% by mass or more, It solves the problem.
  • the ink-jet ink composition of the present invention contains phenylbenzyl acrylate represented by the above formula (1) as an active energy ray-curable compound, thereby maintaining a low viscosity and a high refractive index applicable to ink-jet. Excellent wet heat adhesion can be realized. Since the composition can arbitrarily form a high refractive index member by an ink jet method, it is used for various optical articles, for example, prism sheets used for displays such as liquid crystal display devices, stereoscopic photographs, projection screens, etc. It can be suitably applied to the formation of various optical sheets such as lenticular lens sheets, Fresnel lens sheets used for condenser lenses of overhead projectors, diffraction gratings used for color filters and the like.
  • the ink-jet ink composition of the present invention is an ink composition that can be ejected by an ink-jet apparatus, and is an ink composition that is cured by irradiation with active energy rays.
  • the ink composition contains an active energy ray-curable compound (A) and a photopolymerization initiator (B), and the active energy ray-curable compound (A) is a monofunctional compound represented by the following formula (1) ( By containing a meth) acrylate compound, it is possible to realize a high refractive index and suitable adhesion to an adherend while having a low viscosity that can be discharged by an ink jet apparatus.
  • R 1 is a hydrogen atom or a methyl group.
  • R 2 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom.
  • N 1 and n 2 are 1 Represents 4)
  • the content of the compound represented by the formula (1) in the active energy ray polymerizable compound (A) contained in the composition is 60% by mass or more and 70% by mass. It is preferable that the amount is 80% by mass or more, and more preferably 90% by mass or more.
  • content of the compound represented by Formula (1) can also be 95 mass% or more, and it is also preferable to set it as 100 mass%.
  • the ink-jet ink composition of the present invention may contain an active energy ray polymerizable compound other than the compound represented by the above formula (1).
  • an active energy ray polymerizable compound other than the compound represented by the above formula (1).
  • the other active energy ray-polymerizable compound a monofunctional compound having one active energy ray-polymerizable group and a polyfunctional compound having two or more polymerizable groups can be appropriately used.
  • Examples of monofunctional compounds include n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, and n-octyl.
  • (Meth) acrylate isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybenzyl acrylate, phenoxydiethylene glycol (meth) acrylate, glycidyl (meth) acrylate, morpholine (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, diethylene Recall mono (meth) acrylate, triethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, Methoxypolyethylene glycol
  • a compound having a viscosity at 25 ° C. of 300 mPa ⁇ s or less is preferably used, and a compound having a viscosity of 200 mPa ⁇ s or less is more preferable.
  • the refractive index is preferably 1.4 or more at 25 ° C. and 589 nm, more preferably 1.5 or more, and further preferably 1.55 or more.
  • phenoxybenzyl acrylate and o-phenylphenol ethylene oxide-modified acrylate are preferable because they easily maintain the viscosity of the composition and easily improve the refractive index of the resulting cured product.
  • the content of the monofunctional compound other than the compound represented by the formula (1) in the active energy ray polymerizable compound (A) contained in the inkjet ink composition of the present invention is high. It is preferably 50% by mass or less, more preferably 30% by mass or less, and particularly preferably 10% by mass or less from the viewpoint of maintaining the refractive index.
  • a polyfunctional compound may be used in combination.
  • polyfunctional compounds include full orange (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and propylene glycol.
  • the polyfunctional oligomer which has acryloyl groups such as urethane (meth) acrylate, polyester (meth) acrylate, an epoxy (meth) acrylate, is also contained, for example. These may use 1 type, or may use multiple types.
  • a full orange (meth) acrylate represented by the following formula (2) can be preferably used.
  • R 3 and R 4 each independently represent a hydrogen atom or a methyl group
  • X 1 and X 2 each independently represent a C 2 or C 3 alkylene group
  • m 1 and m 2 each independently represent an integer of 0 or more.
  • the compound represented by the above formula (2) used in the present invention preferably has a refractive index of 1.50 or more, and more preferably 1.53 or more. Moreover, the viscosity is 15000. It is preferably mPa ⁇ s or less, and more preferably 3000 mPa ⁇ s or less. In the above formula (2), m 1 + m 2 is preferably 2 to 30.
  • the polyfunctional compound in the active energy ray-polymerizable compound (A) contained in the inkjet ink composition of the present invention is, from the viewpoint of maintaining a low viscosity,
  • the content is preferably 20% by mass or less, and more preferably 10% by mass or less.
  • a compound having an active energy ray polymerizable group other than the above (meth) acrylate can also be used.
  • compounds other than these (meth) acrylates it is preferable to use at 20 mass% or less in an active energy ray polymeric compound, and it is more preferable to use at 10 mass% or less.
  • Photopolymerization initiator As the photopolymerization initiator used in the present invention, various initiators used in ink jet ink compositions can be used, such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one.
  • the amount is preferably 0.05 to 20 parts by mass, particularly preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the active energy ray polymerizable compound.
  • the inkjet ink composition of the present invention is a composition containing the compound represented by the above formula (1), having a viscosity of 100 mPa ⁇ s or less and a liquid refractive index of 1.57 or more. With this configuration, the ink composition of the present invention can be applied to inkjet, and can realize a high refractive index and excellent wet heat adhesion.
  • the ink-jet ink composition of the present invention has a viscosity at 25 ° C. of preferably 100 mPa ⁇ s or less, more preferably 50 mPa ⁇ s or less. It becomes easy to apply and form to thickness. Moreover, it is more preferable to set it as 30 mPa * s or less, and it is further more preferable to set it as 20 mPa * s or less.
  • the inkjet ink composition of the present invention preferably has a liquid refractive index of 1.57 or more, more preferably 1.575 or more, and further preferably 1.58 or more.
  • a high refractive index can be imparted to the cured product obtained by setting the liquid refractive index, and it can be suitably applied to various optical articles.
  • the surface tension of the inkjet ink composition of the present invention is preferably 20 to 50 mN / m, and more preferably 30 to 50 mN / m.
  • the surface tension is an ink-jet ink composition in this range, it becomes easy to appropriately adjust to suitable ink-jet aptitude by using a leveling agent or the like as necessary.
  • components other than the active energy ray polymerizable compound may be contained.
  • a resin or the like may be used in combination for the purpose of improving viscosity or adhesion to a transparent substrate.
  • the resin include acrylic resins such as methyl methacrylate resin and methyl methacrylate copolymer; polystyrene, methyl methacrylate-styrene copolymer; polyester resin; polyurethane resin; polybutadiene and butadiene-acrylonitrile copolymer. Polybutadiene resin; bisphenol type epoxy resin, epoxy resin such as phenoxy resin and novolac type epoxy resin, and the like.
  • components other than these active energy ray polymerizable compounds it is preferably used at 20 parts by mass or less, preferably at 10 parts by mass or less, relative to 100 parts by mass of the active energy ray polymerizable compound. .
  • inorganic filler In this invention, it is possible to mix
  • the inorganic nanoparticles having a high refractive index include alumina, zirconia, titania, compounds thereof, mixed oxides thereof, and metal oxides thereof.
  • These inorganic nanoparticles (fillers) are effective as a means of increasing the refractive index of cured products because they have a higher refractive index than general organic materials, but considering the balance between the strength of the molded product and adhesion to the substrate.
  • the inorganic nanoparticles are 1 to 20% by mass with respect to the total amount of the active energy ray polymerizable compound (A) and the inorganic nanoparticles is practical. Among them, 1 to 10% by mass is more preferable in order to have both a high refractive index and a low viscosity.
  • additives in the inkjet ink composition of this invention.
  • the additive include an ultraviolet absorber, an antioxidant, a silicon-based additive, a fluorine-based additive, a rheology control agent, a defoaming agent, a release agent, a silane coupling agent, an antistatic agent, and an antifogging agent.
  • coloring agents are preferably 0.05 to 20 parts by mass, and preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the active energy ray polymerizable compound in the inkjet ink composition for optical articles. Particularly preferred.
  • the ink-jet ink composition of the present invention may contain a solvent as necessary, but a lower solvent content is preferable because an ink-jet ink composition that is less likely to contaminate the working environment is obtained.
  • the solvent content in the inkjet ink composition of the present invention is preferably 100 ppm or less, and is preferably substantially not contained.
  • the ink-jet ink composition of the present invention can be formed into a cured product by irradiating with active energy rays after being applied or molded onto a substrate or the like by an ink-jet apparatus according to the intended use.
  • active energy rays include electron beams, ultraviolet rays, and visible rays.
  • an electron beam is used as the active energy beam, a Cochloft Walton type accelerator, a bandegraph type electron accelerator, a resonant transformer type accelerator, an insulated core transformer type, a dynamitron type, a linear filament type, a high frequency type, etc.
  • the curable composition of the present invention can be cured using a generator.
  • mercury lamps such as ultra-high pressure mercury lamp, high pressure mercury lamp, low pressure mercury lamp, metal height lamp, fusion lamp, xenon lamp, carbon arc, high output LED-UV lamp, It can be cured.
  • the cured product of the inkjet ink composition of the present invention preferably has a refractive index of 1.60 or more, more preferably 1.61 or more, and further preferably 1.62 or more. Since the said hardened
  • the hardness of the cured product of the present invention may be appropriately designed according to various uses.
  • the elastic modulus at 25 ° C. is preferably 200 to 800 MPa, and 300 to More preferably, it is 500 MPa.
  • the elastic modulus is measured by dynamic viscoelasticity measurement using “RSAII” manufactured by Rheometric Scientific as a viscoelasticity measuring device, with a temperature rising speed of 3 ° C./Min and a frequency of 3.5 Hz. Value obtained.
  • the glass transition temperature Tg of the cured product is preferably 30 ° C. or higher, It is particularly preferable that the temperature is 35 ° C. or higher. By setting it as the glass transition temperature, it becomes easy to have both a high refractive index and good wet heat adhesion.
  • the upper limit of Tg is not particularly limited, but a higher Tg is humidified in the elastic region in wet heat treatment (accelerated test) at a high temperature, and below Tg (rubbery region). Compared to the exposure, it is more preferable because the water absorption can be reduced.
  • the said glass transition temperature is the value which read the temperature of the peak position of tan-delta represented by ratio of the storage elastic modulus E 'obtained by viscoelasticity measurement, and the complex elastic modulus E "as Tg.
  • the ink jet ink composition of the present invention can suitably produce an optical member by forming a prism or a lens on a transparent resin film or conductive film using an ink jet apparatus.
  • optical members such as prism members used for displays such as liquid crystal display devices, lenticular lenses used for stereoscopic photographs and projection screens, condenser lenses for overhead projectors, diffraction gratings used for color filters, etc. It can be illustrated.
  • optical members of various shapes can be arbitrarily manufactured, so that small-lot and multi-item optical members can be manufactured at low cost.
  • a film-like, sheet-like, or plate-like transparent substrate can be used as the substrate on which the ink-jet ink composition is discharged during the formation of the optical member.
  • the material of the base material may be appropriately selected according to the use, for example, polyester resin such as polyethylene terephthalate (PET) or polyethylene naphthalate (PEN), triacetyl cellulose, polycarbonate resin, methyl methacrylate copolymer, etc.
  • an inorganic substrate such as a glass substrate, a conductive film provided with a conductive layer such as a metal vapor deposition film, and the like can be used in the same manner.
  • the ink-jet ink composition for optical articles of the present invention can be suitably applied to prism lenses and lenticular lenses used in various displays among various optical members, and can prevent reflection of a laminate using a material having a plurality of refractive indexes. It can also be used for applications.
  • the lens has a plurality of fine prism-shaped portions on one side of a sheet-like molded body, and is usually disposed on the back surface (light source side) of the liquid crystal display element so that the prism surface faces the element side.
  • These lenses are sheets having a prism layer made of a cured product of the inkjet ink composition for optical articles on a transparent film, and the prism layer has a prism apex angle ⁇ of 70 to 110 °.
  • ⁇ prism apex angle
  • the pitch of the prism is preferably 100 ⁇ m or less, and particularly preferably 70 ⁇ m or less from the viewpoint of preventing the generation of moire patterns on the screen and further improving the definition of the screen, and is 10 to 30 ⁇ m. Is more preferable.
  • the height of the projections and depressions of the prism is determined by the prism apex angle ⁇ and the prism pitch value, but is preferably 50 ⁇ m or less.
  • the sheet thickness of the prism lens is preferably thick from the viewpoint of strength, but optically is preferably thin in order to suppress the absorption of light, and is preferably 50 ⁇ m to 150 ⁇ m from the viewpoint of these balances.
  • the resin composition was applied to a glass plate, sandwiched between release PET films, and irradiated with UV (1000 mJ / cm 2 : metal halide lamp) from the release PET film side to cure the resin composition. Thereafter, the cured resin film (100 ⁇ m thickness) obtained by peeling off the release PET film and glass plate was measured at a reference wavelength (589 nm) using a multi-wavelength Abbe refractometer (DR-M2) manufactured by ATAGO. did.
  • DR-M2 multi-wavelength Abbe refractometer
  • Viscosity measurement> The viscosity at 25 ° C. of the resin compositions prepared in Examples and Comparative Examples was measured using an E-type viscometer (DV-II + VISCOMETER) manufactured by BROOKFIELD.
  • ⁇ Storage modulus> Using “RSAII” manufactured by Rheometric Scientific as a viscoelasticity measurement device, dynamic viscoelasticity measurement is performed under the measurement conditions of a temperature rising speed of 3 ° C./Min and a frequency of 3.5 Hz, and the elastic modulus at 25 ° C. is measured. It was measured.
  • ⁇ Moist heat adhesion> The resin composition was coated on a glass plate, sandwiched between PET films, and irradiated with UV (1000 mJ / cm 2 : metal halide lamp) from the PET film side to cure the resin composition. Thereafter, the glass plate was peeled off to obtain a test piece having a cured resin film thickness of 100 ⁇ m. The obtained test piece is allowed to stand for 1 week under conditions of a temperature of 40 ° C. and a humidity of 90% RH, and then a 10 ⁇ 10 cross cut is performed with a cutter knife, and the cross cut part is peeled off with an adhesive tape. An eye test was performed. With respect to the square 100, the number of residual masses after the adhesive tape was peeled was measured.
  • Examples 1 to 3 Comparative Examples 1 and 2
  • the compound was melt-mixed with the formulation shown in Table 1 below to prepare a resin composition.
  • the above-mentioned evaluation was performed about the obtained resin composition.
  • surface is a mass part.
  • EO-modified acrylate of o-phenylphenol ethylene oxide-modified (n ⁇ 1) acrylate of o-phenylphenol
  • the resin composition of the present invention has a high refractive index, but can be applied to inkjet and has excellent wet heat adhesion.
  • the ink-jet ink composition of the present invention is a composition having a high refractive index and excellent wet heat adhesion, it can be suitably used for optical articles.
  • Suitable articles include display materials such as liquid crystal displays and organic EL displays, illumination members such as fluorescent lamps, LED lamps, and organic EL lamps, measuring / sensing devices such as cameras, sensors, and microscopes, and lenses such as glasses. .
  • display materials such as liquid crystal displays and organic EL displays
  • illumination members such as fluorescent lamps, LED lamps, and organic EL lamps
  • measuring / sensing devices such as cameras, sensors, and microscopes
  • lenses such as glasses.

Abstract

Provided is an inkjet ink composition which contains an active energy ray-curable compound (A) and a photopolymerization initiator (B), wherein a monofunctional (meth)acrylate compound represented by formula (1) (in formula (1), R1 is a hydrogen atom or a methyl group, R2 groups are each independently a hydrogen atom, a fluorine atom, a chlorine atom or bromine atom, and n1 and n2 are each 1-4) is contained at a quantity of 60 mass% or more of the active energy ray-curable compound (A).

Description

インクジェットインク組成物Inkjet ink composition
　本発明は、光学物品に使用するインクジェットインク組成物、該組成物を硬化させた硬化物に関する。 The present invention relates to an inkjet ink composition used for an optical article and a cured product obtained by curing the composition.
　近年、レンチキュラーレンズやコンデンサーレンズ等、液晶ディスプレイや有機ＥＬディスプレイ等の画像表示装置に使用する光学部材をインクジェット法によって形成する試みが各種検討されている（例えば、特許文献１参照）。 In recent years, various attempts to form an optical member used for an image display device such as a lenticular lens and a condenser lens such as a liquid crystal display and an organic EL display by an ink jet method have been studied (for example, see Patent Document 1).
　画像表示装置の光学部材をインクジェット法によって形成するために用いられるインクジェットインク組成物としては、例えば、フルオレン系（メタ）アクリレートと特定の希釈剤とを含有する低粘度の光硬化性インクジェットインクが開示されている（例えば、特許文献２参照）。 As an ink-jet ink composition used for forming an optical member of an image display device by an ink-jet method, for example, a low-viscosity photo-curable ink-jet ink containing fluorene-based (meth) acrylate and a specific diluent is disclosed. (For example, refer to Patent Document 2).
特開２０１０－２２４２００号公報JP 2010-224200 A 特開２０１３－１８５０４０号公報JP 2013-185040 A
　上記特許文献２においては、フルオレン系（メタ）アクリレートと共に特定の希釈剤や重合開始剤を特定配合にて含有する低粘度の光硬化性インクジェットインクにより、高い屈折率と優れた密着性を実現できることが開示されている。 In the said patent document 2, a high refractive index and the outstanding adhesiveness can be implement | achieved with the low-viscosity photocurable inkjet ink which contains a specific diluent and a polymerization initiator with a specific mixing | blending with a fluorene type (meth) acrylate. Is disclosed.
　しかし、画像表示装置は用途に応じて各種の環境下で使用されることから、常態のみならず湿熱環境下での高い密着性の実現も求められていた。 However, since the image display device is used in various environments depending on applications, it has been required to realize high adhesion not only in a normal state but also in a humid heat environment.
　本発明の課題は、インクジェットへの適用が可能でありながら、高い屈折率と優れた湿熱密着性とを有するインクジェットインク組成物を提供することにある。 An object of the present invention is to provide an ink-jet ink composition having a high refractive index and excellent wet heat adhesion while being applicable to ink-jet.
　活性エネルギー線硬化性化合物（Ａ）及び光重合開始剤（Ｂ）を含有するインクジェットインク組成物であって、活性エネルギー線硬化性化合物（Ａ）として、下記式（１） An inkjet ink composition containing an active energy ray-curable compound (A) and a photopolymerization initiator (B), wherein the active energy ray-curable compound (A) is represented by the following formula (1):
Figure JPOXMLDOC01-appb-C000002
 （式（１）中、Ｒ１は、水素原子又はメチル基である。Ｒ２は、それぞれ独立に、水素原子、フッ素原子、塩素原子、臭素原子を表す。またｎ１及びｎ２は、１～４を表す。）
で表される単官能（メタ）アクリレート化合物を含有し、
　インクジェットインク組成物に含まれる活性エネルギー線硬化性化合物（Ａ）中の式（1）で表される単官能（メタ）アクリレート化合物の含有量が６０質量％以上であるインクジェットインク組成物により、上記課題を解決するものである。
Figure JPOXMLDOC01-appb-C000002
 (In Formula (1), R 1 is a hydrogen atom or a methyl group. R 2 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom. N 1 and n 2 are 1 Represents 4)
Containing a monofunctional (meth) acrylate compound represented by
By the inkjet ink composition in which the content of the monofunctional (meth) acrylate compound represented by the formula (1) in the active energy ray-curable compound (A) contained in the inkjet ink composition is 60% by mass or more, It solves the problem.
　本発明のインクジェットインク組成物は、上記式（１）で表されるフェニルベンジルアクリレートを活性エネルギー線硬化性化合物として含有することで、インクジェットに適用可能な低粘度と高屈折率を保持しながら、優れた湿熱密着性を実現できる。当該組成物は高屈折率の部材をインクジェット方式にて任意に形成できることから、各種光学物品用、例えば、液晶表示装置等のディスプレイに使用されるプリズムシート、立体写真や投影スクリーン等に使用されるレンチキュラーレンズシート、オーバーヘッドプロジェクターのコンデンサーレンズ等に使用されるフレネルレンズシート、カラーフィルタ等に用いられる回折格子等の各種光学シートの形成に好適に適用できる。 The ink-jet ink composition of the present invention contains phenylbenzyl acrylate represented by the above formula (1) as an active energy ray-curable compound, thereby maintaining a low viscosity and a high refractive index applicable to ink-jet. Excellent wet heat adhesion can be realized. Since the composition can arbitrarily form a high refractive index member by an ink jet method, it is used for various optical articles, for example, prism sheets used for displays such as liquid crystal display devices, stereoscopic photographs, projection screens, etc. It can be suitably applied to the formation of various optical sheets such as lenticular lens sheets, Fresnel lens sheets used for condenser lenses of overhead projectors, diffraction gratings used for color filters and the like.
（活性エネルギー線重合性化合物）
　本発明のインクジェットインク組成物は、インクジェット装置により吐出が可能なインク組成物であり、活性エネルギー線の照射により硬化するインク組成物である。当該インク組成物は、活性エネルギー線硬化性化合物（Ａ）及び光重合開始剤（Ｂ）を含有し、活性エネルギー線硬化性化合物（Ａ）として、下記式（１）で表される単官能（メタ）アクリレート化合物を含有することで、インクジェット装置による吐出が可能な低い粘度を有しつつ、高い屈折率や被着体との好適な密着性を実現できる。 (Active energy ray polymerizable compound)
The ink-jet ink composition of the present invention is an ink composition that can be ejected by an ink-jet apparatus, and is an ink composition that is cured by irradiation with active energy rays. The ink composition contains an active energy ray-curable compound (A) and a photopolymerization initiator (B), and the active energy ray-curable compound (A) is a monofunctional compound represented by the following formula (1) ( By containing a meth) acrylate compound, it is possible to realize a high refractive index and suitable adhesion to an adherend while having a low viscosity that can be discharged by an ink jet apparatus.
Figure JPOXMLDOC01-appb-C000003
 （式（１）中、Ｒ１は、水素原子又はメチル基である。Ｒ２は、それぞれ独立に、水素原子、フッ素原子、塩素原子、臭素原子を表す。またｎ１及びｎ２は、１～４を表す。）
Figure JPOXMLDOC01-appb-C000003
 (In Formula (1), R 1 is a hydrogen atom or a methyl group. R 2 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom. N 1 and n 2 are 1 Represents 4)
　本発明のインクジェットインク組成物においては、当該組成物に含まれる活性エネルギー線重合性化合物（Ａ）中の式（１）で表される化合物の含有量が６０質量％以上であり、７０質量％以上であることが好ましく、８０質量％以上であることがより好ましく、９０質量％以上であることがさらに好ましい。式（１）で表される化合物の含有量を上記範囲とすることで、低い粘度を有しつつ、高い屈折率や被着体との好適な密着性を確保しやすくなる。また、配合が容易であることから、当該式（１）で表される化合物の含有量を９５質量％以上とすることもでき、１００質量％とすることも好ましい。 In the inkjet ink composition of the present invention, the content of the compound represented by the formula (1) in the active energy ray polymerizable compound (A) contained in the composition is 60% by mass or more and 70% by mass. It is preferable that the amount is 80% by mass or more, and more preferably 90% by mass or more. By making content of the compound represented by Formula (1) into the said range, it becomes easy to ensure favorable adhesiveness with a high refractive index and a to-be-adhered body, having a low viscosity. Moreover, since mixing | blending is easy, content of the compound represented by the said Formula (1) can also be 95 mass% or more, and it is also preferable to set it as 100 mass%.
　本発明のインクジェットインク組成物は、上記式（１）で表される化合物以外の他の活性エネルギー線重合性化合物を含有してもよい。当該他の活性エネルギー線重合性化合物としては、活性エネルギー線重合性基を一つ有する単官能の化合物、当該重合性基を二つ以上有する多官能の化合物を適宜使用できる。 The ink-jet ink composition of the present invention may contain an active energy ray polymerizable compound other than the compound represented by the above formula (1). As the other active energy ray-polymerizable compound, a monofunctional compound having one active energy ray-polymerizable group and a polyfunctional compound having two or more polymerizable groups can be appropriately used.
　単官能の化合物としては、例えば、ｎ－ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｔｅｒｔ－ブチル（メタ）アクリレート、ｎ－ペンチル（メタ）アクリレート、ｎ－ヘキシル（メタ）アクリレート、ｎ－オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、２－エチルヘキシル（メタ）アクリレート、ベンジル（メタ）アクリレート、フェノキシエチル（メタ）アクリレート、フェノキシベンジルアクリレート、フェノキシジエチレングリコール（メタ）アクリレート、グリシジル（メタ）アクリレート、モルホリン（メタ）アクリレート、２－ヒドロキシエチル（メタ）アクリレート、２－ヒドロキシプロピル（メタ）アクリレート、４－ヒドロキシブチル（メタ）アクリレート、ジエチレングリコールモノ（メタ）アクリレート、トリエチレングリコールモノ（メタ）アクリレート、ジプロピレングリコールモノ（メタ）アクリレート、２－メトキシエチル（メタ）アクリレート、メトキシジエチレングリコール（メタ）アクリレート、メトキシトリエチレングリコール（メタ）アクリレート、メトキシポリエチレングリコール（メタ）アクリレート、２－ブトキシエチル（メタ）アクリレート、ブトキシトリエチレングリコール（メタ）アクリレート、２－エトキシエチル（メタ）アクリレート、２－（２－エトキシエトキシ）エチル（メタ）アクリレート、エトキシポリエチレングリコール（メタ）アクリレート、４－ノニルフェノキシエチレングリコール（メタ）アクリレート、テトラヒドロフルフリル（メタ）アクリレート、カプロラクトン変性テトラヒドロフルフリル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、２－ヒドロキシ－３－フェノキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、シクロヘキシルメチル（メタ）アクリレート、シクロヘキシルエチル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンタニロキシエチル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ジシクロペンテニロキシエチル（メタ）アクリレート、フェニルフェノールのエチレンオキサイド変性アクリレート等の単官能（メタ）アクリレートを好ましく使用できる。これら単官能（メタ）アクリレートは、一種を使用しても複数種を使用してもよい。 Examples of monofunctional compounds include n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, and n-octyl. (Meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybenzyl acrylate, phenoxydiethylene glycol (meth) acrylate, glycidyl (meth) acrylate, morpholine (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, diethylene Recall mono (meth) acrylate, triethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, Methoxypolyethylene glycol (meth) acrylate, 2-butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, ethoxy Polyethylene glycol (meth) acrylate, 4-nonylphenoxyethylene glycol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate , Caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, cyclohexylmethyl (meth) acrylate, cyclohexyl Ethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, ethylene oxide of phenylphenol Monofunctional (meth) acrylates such as modified acrylates can be preferably used. These monofunctional (meth) acrylates may be used alone or in combination.
　本発明に併用する単官能化合物としては、２５℃における粘度が３００ｍＰａ・ｓ以下の化合物を使用することが好ましく、２００ｍＰａ・ｓ以下の化合物であることがより好ましい。また、その屈折率が２５℃、５８９ｎｍにおいて、１．４以上であることが好ましく、１．５以上であることがより好ましく、１．５５以上であることがさらに好ましい。 As the monofunctional compound used in combination with the present invention, a compound having a viscosity at 25 ° C. of 300 mPa · s or less is preferably used, and a compound having a viscosity of 200 mPa · s or less is more preferable. Further, the refractive index is preferably 1.4 or more at 25 ° C. and 589 nm, more preferably 1.5 or more, and further preferably 1.55 or more.
　上記の単官能化合物のなかでも、フェノキシベンジルアクリレートやｏ－フェニルフェノールのエチレンオキサイド変性アクリレートは、組成物の粘度を好適に保持しつつ、得られる硬化物の屈折率を向上させやすいため好ましい。 Among the monofunctional compounds described above, phenoxybenzyl acrylate and o-phenylphenol ethylene oxide-modified acrylate are preferable because they easily maintain the viscosity of the composition and easily improve the refractive index of the resulting cured product.
　これら単官能化合物を併用する場合には、本発明のインクジェットインク組成物に含まれる活性エネルギー線重合性化合物（Ａ）中の式（１）で表される化合物以外の単官能化合物の含有量が５０質量％以下であることが好ましく、３０質量％以下であることがより好ましく、１０質量％以下であることが、屈折率を維持する上で、特に好ましい。 When these monofunctional compounds are used in combination, the content of the monofunctional compound other than the compound represented by the formula (1) in the active energy ray polymerizable compound (A) contained in the inkjet ink composition of the present invention is high. It is preferably 50% by mass or less, more preferably 30% by mass or less, and particularly preferably 10% by mass or less from the viewpoint of maintaining the refractive index.
　本発明においては、更に、多官能の化合物を併用しても構わない。多官能の化合物としては、例えば、フルオレンジ（メタ）アクリレート、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート、ブチレングリコールジ（メタ）アクリレート、テトラブチレングリコールジ（メタ）アクリレート、１，４－ブタンジオールジ（メタ）アクリレート、１，６－ヘキサンジオールジ（メタ）アクリレート、１，９－ノナンジオールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、ビスフェノールＡのエチレンオキサイド付加物のジ（メタ）アクリレート、ビスフェノールＡのプロピレンオキサイド付加物のジ（メタ）アクリレート、ビスフェノールＦのエチレンオキサイド付加物のジ（メタ）アクリレート、ビスフェノールＦのプロピレンオキサイド付加物のジ（メタ）アクリレート、ジシクロペンタニルジ（メタ）アクリレート、グリセロールジ（メタ）アクリレート、ネオペンチルグリコールヒドロキシピバリン酸エステルジ（メタ）アクリレート、カプロラクトン変性ヒドロキシピバリン酸ネオペンチルグリコールジ（メタ）アクリレート、テトラブロモビスフェノールＡジ（メタ）アクリレート、ヒドロピバルアルデヒド変性トリメチロールプロパンジ（メタ）アクリレート、１，４－シクロヘキサンジメタノールジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、トリメチロールプロパンのエチレンオキサイド付加物のトリ（メタ）アクリレート、トリメチロールプロパンのプロピレンオキサイド付加物のトリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、グリセロールトリ（メタ）アクリレート、アルキル変性したジペンタエリスリトールのトリ（メタ）アクリレート、ジトリメチロールプロパンテトラ（メタ）アクリレート、ジトリメチロールプロパンのエチレンオキサイド付加物のテトラ（メタ）アクリレート、ジトリメチロールプロパンのプロピレンオキサイド付加物のテトラ（メタ）アクリレート等の多官能（メタ）アクリレートを例示できる。また、多官能（メタ）アクリレートとしては、例えばウレタン（メタ）アクリレート、ポリエステル（メタ）アクリレート、エポキシ（メタ）アクリレートなどのアクリロイル基を有する多官能オリゴマーも含まれる。これらは、一種を使用しても複数種を使用してもよい。 In the present invention, a polyfunctional compound may be used in combination. Examples of polyfunctional compounds include full orange (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, and propylene glycol. Di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, tetrabutylene glycol di (meth) acrylate, 1,4-butanediol di (meth) ) Acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, bisphenol Di (meth) acrylate of ethylene oxide adduct of diol A, di (meth) acrylate of propylene oxide adduct of bisphenol A, di (meth) acrylate of ethylene oxide adduct of bisphenol F, propylene oxide adduct of bisphenol F Di (meth) acrylate, dicyclopentanyl di (meth) acrylate, glycerol di (meth) acrylate, neopentyl glycol hydroxypivalate ester di (meth) acrylate, caprolactone-modified hydroxypivalate neopentyl glycol di (meth) acrylate, Tetrabromobisphenol A di (meth) acrylate, hydropivalaldehyde-modified trimethylolpropane di (meth) acrylate, 1,4-cyclohexanedimethanol di ( ) Acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane ethylene oxide adduct tri (meth) acrylate, trimethylolpropane propylene oxide adduct tri (meth) acrylate, pentaerythritol tri (meth) acrylate , Glycerol tri (meth) acrylate, alkyl-modified dipentaerythritol tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, ditrimethylolpropane ethylene oxide adduct tetra (meth) acrylate, ditrimethylolpropane propylene A polyfunctional (meth) acrylate such as tetra (meth) acrylate of an oxide adduct can be exemplified. Moreover, as a polyfunctional (meth) acrylate, the polyfunctional oligomer which has acryloyl groups, such as urethane (meth) acrylate, polyester (meth) acrylate, an epoxy (meth) acrylate, is also contained, for example. These may use 1 type, or may use multiple types.
　上記の中でも、高い屈折率の硬化物を得るに際しては、下記式（２）で表されるフルオレンジ（メタ）アクリレートを好ましく使用できる。 Among the above, when obtaining a cured product having a high refractive index, a full orange (meth) acrylate represented by the following formula (2) can be preferably used.
Figure JPOXMLDOC01-appb-C000004
 （式（２）中、Ｒ３及びＲ４は、互いに独立して水素原子又はメチル基を表し、Ｘ１及びＸ２は、互いに独立して炭素原子数２又は３のアルキレン基を表し、ｍ１及びｍ２は互いに独立して０以上の整数を表す。）
Figure JPOXMLDOC01-appb-C000004
 (In Formula (2), R 3 and R 4 each independently represent a hydrogen atom or a methyl group, X 1 and X 2 each independently represent a C 2 or C 3 alkylene group, m 1 and m 2 each independently represent an integer of 0 or more.)
　本発明に使用する上記式（２）で表される化合物は、その屈折率が１．５０以上であることが好ましく、１．５３以上であることがより好ましい。また、その粘度は１５０００
ｍＰａ・ｓ以下であることが好ましく、３０００ｍＰａ・ｓ以下であることがより好ましい。また、上記式（２）中のｍ１＋ｍ２が２～３０であることが好ましい。 The compound represented by the above formula (2) used in the present invention preferably has a refractive index of 1.50 or more, and more preferably 1.53 or more. Moreover, the viscosity is 15000.
It is preferably mPa · s or less, and more preferably 3000 mPa · s or less. In the above formula (2), m 1 + m 2 is preferably 2 to 30.
　これら多官能の（メタ）アクリレートを使用する場合には、本発明のインクジェットインク組成物に含まれる活性エネルギー線重合性化合物（Ａ）中の多官能化合物は、低粘度を維持する観点から、その含有量は、２０質量％以下とすることが好ましく、１０質量％以下とすることがより好ましい。 When these polyfunctional (meth) acrylates are used, the polyfunctional compound in the active energy ray-polymerizable compound (A) contained in the inkjet ink composition of the present invention is, from the viewpoint of maintaining a low viscosity, The content is preferably 20% by mass or less, and more preferably 10% by mass or less.
　また、本発明のインクジェットインク組成物においては、上記（メタ）アクリレート以外の活性エネルギー線重合性基を有する化合物を使用することもできる。また、これら（メタ）アクリレート以外の化合物を使用する場合には、活性エネルギー線重合性化合物中の２０質量％以下で使用することが好ましく、１０質量％以下で使用することがより好ましい。なお、高い屈折率や湿熱密着性を調整しやすいことから、実質的に含有しないことも好ましい。 Further, in the ink-jet ink composition of the present invention, a compound having an active energy ray polymerizable group other than the above (meth) acrylate can also be used. Moreover, when using compounds other than these (meth) acrylates, it is preferable to use at 20 mass% or less in an active energy ray polymeric compound, and it is more preferable to use at 10 mass% or less. In addition, since it is easy to adjust a high refractive index and wet heat adhesiveness, it is also preferable not to contain substantially.
（光重合開始剤）
　本発明に使用する光重合開始剤は、インクジェットインク組成物に用いられる各種開始剤を使用でき、例えば、１－ヒドロキシシクロヘキシルフェニルケトン、２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン、１－〔４－（２－ヒドロキシエトキシ）フェニル〕－２－ヒドロキシ－２－メチル－１－プロパン－１－オン、チオキサントン及びチオキサントン誘導体、２，２’－ジメトキシ－１，２－ジフェニルエタン－１－オン、２，４，６－トリメチルベンゾイルジフェニルホスフィンオキシド、ビス（２，４，６－トリメチルベンゾイル）フェニルホスフィンオキシド、２－メチル－１－［４－（メチルチオ）フェニル］－２－モルホリノ－１－プロパノン、２－ベンジル－２－ジメチルアミノ－１－（４－モルホリノフェニル）－ブタン－１－オン等を好ましく使用できる。これら開始剤は一種のみを使用しても二種以上を混合して使用してもよい。 (Photopolymerization initiator)
As the photopolymerization initiator used in the present invention, various initiators used in ink jet ink compositions can be used, such as 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one. 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2′-dimethoxy-1,2-diphenylethane 1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino- 1-propanone, 2-benzyl-2-dimethylamino-1- (4-morpholinov Enyl) -butan-1-one and the like can be preferably used. These initiators may be used alone or in combination of two or more.
　光重合開始剤の使用量は特に制限はないが、好適な硬化性や、得られる硬化物の好適な耐スクラッチ性や自己治癒性等を得やすいことから、光学物品用インクジェットインク組成物中の活性エネルギー線重合性化合物１００質量部に対して０．０５～２０質量部であることが好ましく、０．１～１０質量部であることが特に好ましい。 Although there is no restriction | limiting in particular in the usage-amount of a photoinitiator, Since it is easy to obtain suitable sclerosis | hardenability, the suitable scratch resistance of the hardened | cured material obtained, self-healing property, etc., in the inkjet ink composition for optical articles The amount is preferably 0.05 to 20 parts by mass, particularly preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the active energy ray polymerizable compound.
（インクジェットインク組成物）
　本発明のインクジェットインク組成物は、上記式（１）で表される化合物を含有し、粘度が１００ｍＰａ・ｓ以下、液屈折率が１．５７以上の組成物である。本発明のインク組成物は当該構成により、インクジェットへの適用が可能で、かつ高い屈折率と優れた湿熱密着性とを実現できる。 (Inkjet ink composition)
The inkjet ink composition of the present invention is a composition containing the compound represented by the above formula (1), having a viscosity of 100 mPa · s or less and a liquid refractive index of 1.57 or more. With this configuration, the ink composition of the present invention can be applied to inkjet, and can realize a high refractive index and excellent wet heat adhesion.
　本発明のインクジェットインク組成物は、２５℃での粘度を好ましくは１００ｍＰａ・ｓ以下、より好ましくは５０ｍＰａ・ｓ以下とすることで、インクジェット装置での吐出による各種光学物品用途での所望の形状や厚さへの塗布・成形がしやすくなる。また、３０ｍＰａ・ｓ以下とすることがより好ましく、２０ｍＰａ・ｓ以下とすることがさらに好ましい。 The ink-jet ink composition of the present invention has a viscosity at 25 ° C. of preferably 100 mPa · s or less, more preferably 50 mPa · s or less. It becomes easy to apply and form to thickness. Moreover, it is more preferable to set it as 30 mPa * s or less, and it is further more preferable to set it as 20 mPa * s or less.
　本発明のインクジェットインク組成物は、その液屈折率が１．５７以上であることが好ましく、１．５７５以上であることがより好ましく、１．５８以上であることがさらに好ましい。当該液屈折率とすることで得られる硬化物に、高い屈折率を付与でき、各種光学物品に好適に適用できる。 The inkjet ink composition of the present invention preferably has a liquid refractive index of 1.57 or more, more preferably 1.575 or more, and further preferably 1.58 or more. A high refractive index can be imparted to the cured product obtained by setting the liquid refractive index, and it can be suitably applied to various optical articles.
　また、本発明のインクジェットインク組成物は、その表面張力が２０～５０ｍＮ／ｍであることが好ましく、３０～５０ｍＮ／ｍであることがより好ましい。表面張力が当該範囲のインクジェットインク組成物であると、必要に応じてレベリング剤等を使用することで好適なインクジェット適性に適宜調整しやすくなる。 Further, the surface tension of the inkjet ink composition of the present invention is preferably 20 to 50 mN / m, and more preferably 30 to 50 mN / m. When the surface tension is an ink-jet ink composition in this range, it becomes easy to appropriately adjust to suitable ink-jet aptitude by using a leveling agent or the like as necessary.
　本発明のインクジェットインク組成物においては、上記活性エネルギー線重合性化合物以外の成分を含有してもよく、例えば、粘度や透明基板への接着性改良等を目的に樹脂等を併用してもよい。当該樹脂としては、例えば、メチルメタクリレート樹脂、メチルメタクリレート系共重合物等のアクリル樹脂；ポリスチレン、メチルメタクリレート－スチレン系共重合物；ポリエステル樹脂；ポリウレタン樹脂；ポリブタジエンやブタジエン－アクリロニトリル系共重合物などのポリブタジエン樹脂；ビスフェノール型エポキシ樹脂、フェノキシ樹脂やノボラック型エポキシ樹脂などのエポキシ樹脂等が挙げられる。これら活性エネルギー線重合性化合物以外の成分を使用する場合には、活性エネルギー線重合性化合物１００質量部に対して２０質量部以下で使用することが好ましく、１０質量部以下で使用することが好ましい。 In the ink-jet ink composition of the present invention, components other than the active energy ray polymerizable compound may be contained. For example, a resin or the like may be used in combination for the purpose of improving viscosity or adhesion to a transparent substrate. . Examples of the resin include acrylic resins such as methyl methacrylate resin and methyl methacrylate copolymer; polystyrene, methyl methacrylate-styrene copolymer; polyester resin; polyurethane resin; polybutadiene and butadiene-acrylonitrile copolymer. Polybutadiene resin; bisphenol type epoxy resin, epoxy resin such as phenoxy resin and novolac type epoxy resin, and the like. When using components other than these active energy ray polymerizable compounds, it is preferably used at 20 parts by mass or less, preferably at 10 parts by mass or less, relative to 100 parts by mass of the active energy ray polymerizable compound. .
（無機フィラー）
　本発明においては、必要に応じて無機材料（ナノ粒子）を配合することが可能である。
屈折率の高い無機ナノ粒子としては、アルミナ、ジルコニア、チタニア、それらの化合物、若しくはそれらの混合酸化物を含むか、又はそれらの金属酸化物が挙げられる。これら無機ナノ粒子（フィラー）は、一般的な有機材料よりも屈折率が高いので硬化物の屈折率を上げる手段としては有効であるが、成型物の強度や基材密着性とのバランスを考慮する必要があり、配合量としては、活性エネルギー線重合性化合物（Ａ）と無機ナノ粒子の合計量に対して、無機ナノ粒子が１～２０質量％となる範囲が実用的である。また、その中でも、更に高屈折率と低粘度を兼備するためには、１～１０質量％がより好ましい。 (Inorganic filler)
In this invention, it is possible to mix | blend an inorganic material (nanoparticle) as needed.
Examples of the inorganic nanoparticles having a high refractive index include alumina, zirconia, titania, compounds thereof, mixed oxides thereof, and metal oxides thereof. These inorganic nanoparticles (fillers) are effective as a means of increasing the refractive index of cured products because they have a higher refractive index than general organic materials, but considering the balance between the strength of the molded product and adhesion to the substrate. As a blending amount, a range in which the inorganic nanoparticles are 1 to 20% by mass with respect to the total amount of the active energy ray polymerizable compound (A) and the inorganic nanoparticles is practical. Among them, 1 to 10% by mass is more preferable in order to have both a high refractive index and a low viscosity.
（添加剤）
　また、本発明のインクジェットインク組成物においては、各種添加剤を使用してもよい。当該添加剤としては、例えば、紫外線吸収剤、酸化防止剤、シリコン系添加剤、フッ素系添加剤、レオロジーコントロール剤、脱泡剤、離型剤、シランカップリング剤、帯電防止剤、防曇剤、着色剤等が挙げられる。これら添加剤は、光学物品用インクジェットインク組成物中の活性エネルギー線重合性化合物１００質量部に対して０．０５～２０質量部であることが好ましく、０．１～１０質量部であることが特に好ましい。 (Additive)
Moreover, you may use various additives in the inkjet ink composition of this invention. Examples of the additive include an ultraviolet absorber, an antioxidant, a silicon-based additive, a fluorine-based additive, a rheology control agent, a defoaming agent, a release agent, a silane coupling agent, an antistatic agent, and an antifogging agent. And coloring agents. These additives are preferably 0.05 to 20 parts by mass, and preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the active energy ray polymerizable compound in the inkjet ink composition for optical articles. Particularly preferred.
　本発明のインクジェットインク組成物には必要に応じて溶剤を含有させても良いが、溶剤の含有率は少ないほうが作業環境を汚染しにくいインクジェットインク組成物が得られることから好ましい。具体的には、本発明のインクジェットインク組成物中の溶剤含有率は１００ｐｐｍ以下が好ましく、実質的に含有しないことが好ましい。 The ink-jet ink composition of the present invention may contain a solvent as necessary, but a lower solvent content is preferable because an ink-jet ink composition that is less likely to contaminate the working environment is obtained. Specifically, the solvent content in the inkjet ink composition of the present invention is preferably 100 ppm or less, and is preferably substantially not contained.
（硬化物）
　本発明のインクジェットインク組成物は、目的用途に応じてインクジェット装置により基材等へ塗布や、成型した後、活性エネルギー線を照射して硬化物とすることができる。活性エネルギー線としては、電子線、紫外線、可視光線等が挙げられる。活性エネルギー線として、電子線を用いる場合には、コックロフトワルトン型加速器、バンデグラフ型電子加速器、共振変圧器型加速器、絶縁コア変圧器型、ダイナミトロン型、リニアフィラメント型および高周波型などの電子線発生装置を用いて本発明の硬化性組成物を硬化させることができる。また、活性エネルギー線として紫外線を用いる場合は、超高圧水銀灯、高圧水銀灯、低圧水銀灯等の水銀灯、メタルハイトランプ、フュージョンランプ、キセノンランプ、カーボンアーク、高出力のＬＥＤ－ＵＶランプ等により照射し、硬化させることができる。 (Cured product)
The ink-jet ink composition of the present invention can be formed into a cured product by irradiating with active energy rays after being applied or molded onto a substrate or the like by an ink-jet apparatus according to the intended use. Examples of active energy rays include electron beams, ultraviolet rays, and visible rays. When an electron beam is used as the active energy beam, a Cochloft Walton type accelerator, a bandegraph type electron accelerator, a resonant transformer type accelerator, an insulated core transformer type, a dynamitron type, a linear filament type, a high frequency type, etc. The curable composition of the present invention can be cured using a generator. Also, when using ultraviolet rays as active energy rays, irradiate with mercury lamps such as ultra-high pressure mercury lamp, high pressure mercury lamp, low pressure mercury lamp, metal height lamp, fusion lamp, xenon lamp, carbon arc, high output LED-UV lamp, It can be cured.
　本発明のインクジェットインク組成物の硬化物は、屈折率が１．６０以上であることが好ましく、１．６１以上であることがより好ましく、１．６２以上であることがさらに好ましい。当該硬化物は、高い屈折率を有し、また好適な靭性等を有することから、各種光学物品に好適に適用できる。 The cured product of the inkjet ink composition of the present invention preferably has a refractive index of 1.60 or more, more preferably 1.61 or more, and further preferably 1.62 or more. Since the said hardened | cured material has a high refractive index and suitable toughness etc., it can be applied suitably for various optical articles.
　本発明の硬化物の硬さは、各種用途に応じて適宜設計すればよいが、例えば、プリズムシートに使用する場合には、２５℃における弾性率が２００～８００ＭＰａであることが好ましく、３００～５００ＭＰａであることがより好ましい。弾性率を当該範囲とすることで機械強度と靭性（伸び）のバランスが良好となり、クラックの発生も抑制しやすくなる。 The hardness of the cured product of the present invention may be appropriately designed according to various uses. For example, when used for a prism sheet, the elastic modulus at 25 ° C. is preferably 200 to 800 MPa, and 300 to More preferably, it is 500 MPa. By setting the elastic modulus within the above range, the balance between mechanical strength and toughness (elongation) is improved, and the occurrence of cracks is easily suppressed.
　なお、当該弾性率は、粘弾性測定装置としてＲｈｅｏｍｅｔｏｒｉｃ　Ｓｃｉｅｎｔｉｆｉｃ社製の「ＲＳＡII」を用いて、測定条件として、昇温スピード３℃／Ｍｉｎ、周波数は３．５Ｈｚの条件で動的粘弾性測定して得られる値とする。 In addition, the elastic modulus is measured by dynamic viscoelasticity measurement using “RSAII” manufactured by Rheometric Scientific as a viscoelasticity measuring device, with a temperature rising speed of 3 ° C./Min and a frequency of 3.5 Hz. Value obtained.
　本発明においては、硬化物のガラス転移温度Ｔｇが３０℃以上であることが好ましく、
３５℃以上であることが特に好ましい。当該ガラス転移温度とすることで、高い屈折率と良好な湿熱密着性とを兼備しやすくなる。Ｔｇの上限は特に制限されるものではないが、Ｔｇが高い方が、高温下での湿熱処理（加速試験）に於いて、弾性領域で加湿されることとなり、Ｔｇ以下（ゴム状領域）での暴露に比べて、吸水率が低減できることからより好ましい。なお、本発明においては、上記式（１）や式（２）で表される化合物の使用や好適な範囲での配合により、当該Ｔｇの範囲に調整しやすくなる。 In the present invention, the glass transition temperature Tg of the cured product is preferably 30 ° C. or higher,
It is particularly preferable that the temperature is 35 ° C. or higher. By setting it as the glass transition temperature, it becomes easy to have both a high refractive index and good wet heat adhesion. The upper limit of Tg is not particularly limited, but a higher Tg is humidified in the elastic region in wet heat treatment (accelerated test) at a high temperature, and below Tg (rubbery region). Compared to the exposure, it is more preferable because the water absorption can be reduced. In addition, in this invention, it becomes easy to adjust to the said Tg range by use of the compound represented by the said Formula (1) or Formula (2), and the mixing | blending in a suitable range.
　なお、当該ガラス転移温度は、粘弾性測定で得られる貯蔵弾性率Ｅ’と複素弾性率Ｅ”の比で表されるｔａｎδのピーク位置の温度をＴｇとして読み取った値のことである。 In addition, the said glass transition temperature is the value which read the temperature of the peak position of tan-delta represented by ratio of the storage elastic modulus E 'obtained by viscoelasticity measurement, and the complex elastic modulus E "as Tg.
（光学部材）
　本発明のインクジェットインク組成物は、透明な樹脂フィルムや導電フィルム等の上にインクジェット装置を用いて、プリズムやレンズを形成することで、光学部材を好適に製造できる。具体的には、液晶表示装置等のディスプレイに使用されるプリズム部材、立体写真や投影スクリーン等に使用されるレンチキュラーレンズ、オーバーヘッドプロジェクターのコンデンサーレンズ、カラーフィルタ等に用いられる回折格子等の光学部材が例示できる。 (Optical member)
The ink jet ink composition of the present invention can suitably produce an optical member by forming a prism or a lens on a transparent resin film or conductive film using an ink jet apparatus. Specifically, optical members such as prism members used for displays such as liquid crystal display devices, lenticular lenses used for stereoscopic photographs and projection screens, condenser lenses for overhead projectors, diffraction gratings used for color filters, etc. It can be illustrated.
　本発明のインクジェットインク組成物によれば、各種形状の光学部材を任意に製造できることから、小ロット、多品目の光学部材を低コストで製造できる。 According to the ink-jet ink composition of the present invention, optical members of various shapes can be arbitrarily manufactured, so that small-lot and multi-item optical members can be manufactured at low cost.
　光学部材の形成に際してインクジェットインク組成物を吐出する基材としては、フィルム状、シート状、板状の透明基材を使用できる。当該基材の材料は用途等に応じて適宜選択すればよく、例えば、ポリエチレンテレフタレート（ＰＥＴ）、ポリエチレンナフタレート（ＰＥＮ）等のポリエステル樹脂、トリアセチルセルロース、ポリカーボネート樹脂、メチルメタクリレート系共重合物などのアクリル樹脂、スチレン樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリカーボネート樹脂、塩化ビニル樹脂、ポリメタクリルイミド樹脂等が挙げられる。また、ガラス基材などの無機基材や、金属蒸着膜等の導電層が設けられた導電フィルム等も同様に用いることが可能である。 As the substrate on which the ink-jet ink composition is discharged during the formation of the optical member, a film-like, sheet-like, or plate-like transparent substrate can be used. The material of the base material may be appropriately selected according to the use, for example, polyester resin such as polyethylene terephthalate (PET) or polyethylene naphthalate (PEN), triacetyl cellulose, polycarbonate resin, methyl methacrylate copolymer, etc. Acrylic resin, styrene resin, polysulfone resin, polyethersulfone resin, polycarbonate resin, vinyl chloride resin, polymethacrylimide resin, and the like. In addition, an inorganic substrate such as a glass substrate, a conductive film provided with a conductive layer such as a metal vapor deposition film, and the like can be used in the same manner.
　本発明の光学物品用インクジェットインク組成物は、各種光学部材のなかでも各種ディスプレイに使用されるプリズムレンズやレンチキュラーレンズに好適に適用できるほか、複数の屈折率を有する材料による積層体の反射防止の用途などにも用いることが出来る。当該レンズは、シート状成形体の片面に微細なプリズム形状部を複数有するものであって、通常、液晶表示素子の背面（光源側）に、該素子側にプリズム面が向くように配設される。 The ink-jet ink composition for optical articles of the present invention can be suitably applied to prism lenses and lenticular lenses used in various displays among various optical members, and can prevent reflection of a laminate using a material having a plurality of refractive indexes. It can also be used for applications. The lens has a plurality of fine prism-shaped portions on one side of a sheet-like molded body, and is usually disposed on the back surface (light source side) of the liquid crystal display element so that the prism surface faces the element side. The
　これらレンズは、透明フィルム上に上記光学物品用インクジェットインク組成物の硬化物からなるプリズム層を有するシートであり、当該プリズム層の形状は、プリズム頂角の角度θが７０～１１０°であることが、集光性に優れ輝度が向上する点から好ましく、７５～１００°であることがより好ましく、８０～９５°であることが特に好ましい。 These lenses are sheets having a prism layer made of a cured product of the inkjet ink composition for optical articles on a transparent film, and the prism layer has a prism apex angle θ of 70 to 110 °. However, it is preferable from the viewpoint of excellent light-collecting properties and improved luminance, more preferably 75 to 100 °, and particularly preferably 80 to 95 °.
　また、プリズムのピッチは、１００μｍ以下であることが好ましく、特に７０μｍ以下であることが、画面のモアレ模様の発生防止や、画面の精細度がより向上する点から好ましく、１０～３０μｍであることがより好ましい。また、プリズムの凹凸の高さは、プリズム頂角の角度θとプリズムのピッチの値によって決定されるが、好ましくは５０μｍ以下であることが好ましい。さらに、プリズムレンズのシート厚さは、強度面からは厚い方が好ましいが、光学的には光の吸収を抑えるため薄い方が好ましく、これらのバランスの点から５０μｍ～１５０μｍであることが好ましい。 The pitch of the prism is preferably 100 μm or less, and particularly preferably 70 μm or less from the viewpoint of preventing the generation of moire patterns on the screen and further improving the definition of the screen, and is 10 to 30 μm. Is more preferable. The height of the projections and depressions of the prism is determined by the prism apex angle θ and the prism pitch value, but is preferably 50 μm or less. Further, the sheet thickness of the prism lens is preferably thick from the viewpoint of strength, but optically is preferably thin in order to suppress the absorption of light, and is preferably 50 μm to 150 μm from the viewpoint of these balances.
　以下に実施例及び比較例を挙げて、本発明をより具体的に説明する。例中の部及び％は、特に記載のない限り、すべて質量基準である。なお、実施例及び比較例における特性等の測定及び評価は、以下のとおり行った。 Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples. Unless otherwise indicated, all parts and percentages in the examples are based on mass. In addition, measurement and evaluation, such as a characteristic in an Example and a comparative example, were performed as follows.
＜屈折率測定＞
　実施例及び比較例にて調製した樹脂組成物の屈折率を、ＡＴＡＧＯ社製多波長アッベ屈折率計（ＤＲ－Ｍ２）を用いて、基準波長（５８９ｎｍ）にて測定した。表の数値は、配合組成物の屈折率を示した。 <Refractive index measurement>
The refractive indexes of the resin compositions prepared in Examples and Comparative Examples were measured at a reference wavelength (589 nm) using a multi-wavelength Abbe refractometer (DR-M2) manufactured by ATAGO. The numerical values in the table indicate the refractive index of the blended composition.
＜膜屈折率の測定＞
　ガラス板に樹脂組成物を塗工し、離型ＰＥＴフィルムに挟んで、離型ＰＥＴフィルム側からＵＶ照射（１０００ｍＪ／ｃｍ２：メタルハライドランプ）を行い、樹脂組成物を硬化させた。　その後、離型PETフィルムおよびガラス板を剥離し得られた樹脂硬化膜（１００μｍ厚）を、ＡＴＡＧＯ社製多波長アッベ屈折率計（ＤＲ－Ｍ２）を用いて、基準波長（５８９ｎｍ）にて測定した。 <Measurement of film refractive index>
The resin composition was applied to a glass plate, sandwiched between release PET films, and irradiated with UV (1000 mJ / cm 2 : metal halide lamp) from the release PET film side to cure the resin composition. Thereafter, the cured resin film (100 μm thickness) obtained by peeling off the release PET film and glass plate was measured at a reference wavelength (589 nm) using a multi-wavelength Abbe refractometer (DR-M2) manufactured by ATAGO. did.
＜粘度測定＞
　実施例及び比較例にて調製した樹脂組成物の２５℃における粘度を、ＢＲＯＯＫＦＩＥＬＤ社製Ｅ型粘度計（ＤＶ－ＩＩ＋ＶＩＳＣＯＭＥＴＥＲ）を用いて測定した。 <Viscosity measurement>
The viscosity at 25 ° C. of the resin compositions prepared in Examples and Comparative Examples was measured using an E-type viscometer (DV-II + VISCOMETER) manufactured by BROOKFIELD.
＜表面張力＞
　実施例及び比較例にて調整した樹脂組成物の２５℃における表面張力を、協和界面科学社製「ＣＢＶＰ－Ａ３」を用いて測定した。 <Surface tension>
The surface tension at 25 ° C. of the resin compositions prepared in Examples and Comparative Examples was measured using “CBVP-A3” manufactured by Kyowa Interface Science Co., Ltd.
＜貯蔵弾性率＞
　粘弾性測定装置としてＲｈｅｏｍｅｔｏｒｉｃ　Ｓｃｉｅｎｔｉｆｉｃ社製の「ＲＳＡII」を用いて、昇温スピード３℃／Ｍｉｎ、周波数は３．５Ｈｚでの測定条件にて動的粘弾性測定を行い、２５℃における弾性率を測定した。 <Storage modulus>
Using “RSAII” manufactured by Rheometric Scientific as a viscoelasticity measurement device, dynamic viscoelasticity measurement is performed under the measurement conditions of a temperature rising speed of 3 ° C./Min and a frequency of 3.5 Hz, and the elastic modulus at 25 ° C. is measured. It was measured.
＜湿熱密着性＞
　ガラス板に樹脂組成物を塗工し、ＰＥＴフィルムに挟んで、ＰＥＴフィルム側からＵＶ照射（１０００ｍＪ／ｃｍ２：メタルハライドランプ）を行い、樹脂組成物を硬化させた。　その後ガラス板を剥離し樹脂硬化膜の厚みが１００μｍである試験片を得た。得られた試験片を、温度４０℃、湿度９０％ＲＨの条件下に１週間静置した後、カッターナイフにて１０×１０のクロスカットを行い、クロスカット部を粘着テープにて剥離する碁盤目試験を行った。マス目１００に対して、粘着テープ剥離後の残存マス数を測定した。 <Moist heat adhesion>
The resin composition was coated on a glass plate, sandwiched between PET films, and irradiated with UV (1000 mJ / cm 2 : metal halide lamp) from the PET film side to cure the resin composition. Thereafter, the glass plate was peeled off to obtain a test piece having a cured resin film thickness of 100 μm. The obtained test piece is allowed to stand for 1 week under conditions of a temperature of 40 ° C. and a humidity of 90% RH, and then a 10 × 10 cross cut is performed with a cutter knife, and the cross cut part is peeled off with an adhesive tape. An eye test was performed. With respect to the square 100, the number of residual masses after the adhesive tape was peeled was measured.
（実施例１～３、比較例１～２）
　下表１に示した配合で化合物を溶融混合し、樹脂組成物を調整した。得られた樹脂組成物につき、上記評価を行った。なお、表中の組成物配合量の数値は質量部である。 (Examples 1 to 3, Comparative Examples 1 and 2)
The compound was melt-mixed with the formulation shown in Table 1 below to prepare a resin composition. The above-mentioned evaluation was performed about the obtained resin composition. In addition, the numerical value of the compounding quantity in a table | surface is a mass part.
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
　上記表中に記載の化合物は下記のとおりである。
　フェニルベンジルアクリレート：下式（ｉ）で表されるアクリレート（ｏ－フェニルベンジルアクリレート：ｐ－フェニルベンジルアクリレート＝８：２の混合物） The compounds described in the above table are as follows.
Phenylbenzyl acrylate: acrylate represented by the following formula (i) (a mixture of o-phenylbenzyl acrylate: p-phenylbenzyl acrylate = 8: 2)
Figure JPOXMLDOC01-appb-C000006
 　ｏ－フェニルフェノールのＥＯ変性アクリレート：ｏ－フェニルフェノールのエチレンオキサイド変性（ｎ≒１）アクリレート
Figure JPOXMLDOC01-appb-C000006
 EO-modified acrylate of o-phenylphenol: ethylene oxide-modified (n≈1) acrylate of o-phenylphenol
　上記表から明らかなとおり、本発明の樹脂組成物は高い屈折率を有しながらも、インクジェットへの適用が可能であり、更に優れた湿熱密着性を有するものであった。 As is apparent from the above table, the resin composition of the present invention has a high refractive index, but can be applied to inkjet and has excellent wet heat adhesion.
　本発明のインクジェットインク組成物は、高い屈折率と優れた湿熱密着性とを有する組成物であることから、光学物品に対し好適に使用可能である。好適物品としては、液晶ディスプレイや有機ＥＬディスプレイと言った表示材料、蛍光灯やＬＥＤ電灯、有機ＥＬ電灯といった照明部材、カメラ、センサー、顕微鏡等の測定・センシング機器、眼鏡等のレンズ等が挙げられる。具体的にはそれらの物品において、レンズ、反射防止材、フィルター、保護膜、封止材等で使用すると好適である。 Since the ink-jet ink composition of the present invention is a composition having a high refractive index and excellent wet heat adhesion, it can be suitably used for optical articles. Suitable articles include display materials such as liquid crystal displays and organic EL displays, illumination members such as fluorescent lamps, LED lamps, and organic EL lamps, measuring / sensing devices such as cameras, sensors, and microscopes, and lenses such as glasses. . Specifically, in these articles, it is preferable to use them in lenses, antireflection materials, filters, protective films, sealing materials and the like.

Claims (4)

  1. 　活性エネルギー線硬化性化合物（Ａ）及び光重合開始剤（Ｂ）を含有するインクジェットインク組成物であって、
    　活性エネルギー線硬化性化合物（Ａ）として、下記式（１）
    Figure JPOXMLDOC01-appb-C000001
     （式（１）中、Ｒ１は、水素原子又はメチル基である。Ｒ２は、それぞれ独立に、水素原子、フッ素原子、塩素原子、臭素原子を表す。またｎ１及びｎ２は、１～４を表す。）
    で表される単官能（メタ）アクリレート化合物を含有し、
    　インクジェットインク組成物に含まれる活性エネルギー線硬化性化合物（Ａ）中の式（1）で表される単官能（メタ）アクリレート化合物の含有量が６０質量％以上であることを特徴とするインクジェットインク組成物。     An inkjet ink composition comprising an active energy ray-curable compound (A) and a photopolymerization initiator (B),
    As the active energy ray-curable compound (A), the following formula (1)
    Figure JPOXMLDOC01-appb-C000001
     (In Formula (1), R 1 is a hydrogen atom or a methyl group. R 2 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom. N 1 and n 2 are 1 Represents 4)
    Containing a monofunctional (meth) acrylate compound represented by
    Inkjet ink characterized in that the content of the monofunctional (meth) acrylate compound represented by the formula (1) in the active energy ray-curable compound (A) contained in the inkjet ink composition is 60% by mass or more. Composition.
  2. 　粘度が１００ｍＰａ・ｓ以下であり、且つ液屈折率が１．５７以上である請求項１に記載のインクジェットインク組成物。 The inkjet ink composition according to claim 1, wherein the viscosity is 100 mPa · s or less and the liquid refractive index is 1.57 or more.
  3. 　表面張力が２０～５０ｍＮ／ｍである請求項１又は２に記載のインクジェットインク組成物。 The inkjet ink composition according to claim 1 or 2, wherein the surface tension is 20 to 50 mN / m.
  4. 　硬化物のガラス転移温度が３０℃以上である請求項１～３のいずれかに記載のインクジェットインク組成物。 The inkjet ink composition according to any one of claims 1 to 3, wherein the cured product has a glass transition temperature of 30 ° C or higher.
PCT/JP2017/040371 2016-11-09 2017-11-09 Inkjet ink composition WO2018088461A1 (en)

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