WO2023182495A1 - Composition de résine durcissable - Google Patents

Composition de résine durcissable Download PDF

Info

Publication number
WO2023182495A1
WO2023182495A1 PCT/JP2023/011812 JP2023011812W WO2023182495A1 WO 2023182495 A1 WO2023182495 A1 WO 2023182495A1 JP 2023011812 W JP2023011812 W JP 2023011812W WO 2023182495 A1 WO2023182495 A1 WO 2023182495A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy compound
curable resin
resin composition
molecule
ester bond
Prior art date
Application number
PCT/JP2023/011812
Other languages
English (en)
Japanese (ja)
Inventor
脩平 ▲高▼嶋
悠斗 小田桐
Original Assignee
太陽ホールディングス株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 太陽ホールディングス株式会社 filed Critical 太陽ホールディングス株式会社
Publication of WO2023182495A1 publication Critical patent/WO2023182495A1/fr

Links

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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • 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
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1525—Four-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C09D11/36—Inkjet printing inks based on non-aqueous solvents

Definitions

  • the present invention relates to a curable resin composition.
  • a light shielding member for a display mounted on a PC or a mobile device is required to have high light shielding properties because it is necessary to suppress the influence of backlight as much as possible. Therefore, a light-shielding ink for forming a black matrix is used as a material for such a light-shielding member.
  • a technique of manufacturing a light shielding member by applying such a light shielding ink to a substrate using an inkjet method is attracting attention.
  • Patent Document 1 discloses an active energy ray-curable ink containing a photocationic polymerization initiator, a polyfunctional epoxy compound, a monofunctional alicyclic epoxy compound, and an oxetane compound. , has proposed a technology for use in inkjet recording.
  • smartphones and smart watches are expected to be used not only at room temperature but also in various environments such as in the summer and inside cars, so it is desirable that the light-shielding ink used has high reliability. It will be done. For example, it must not only have high light blocking properties, but also maintain high adhesion to the substrate even under high temperature and high humidity conditions, have good curability, and the cured coating that is formed after curing. It is also essential for light-shielding inks to have high hardness.
  • light-shielding inks usually contain pigments for light-shielding purposes at a high concentration, and are characterized by a high OD value. Therefore, when applying light-shielding ink to a substrate using the inkjet method, there is a phenomenon in which the light used to photocure the light-shielding ink coating formed on the substrate has difficulty reaching the bottom of the coating. It inevitably happens. As a result, the curability of the entire coating film is insufficient, resulting in a problem that the hardness of the cured coating film itself and its adhesion to a substrate such as glass or metal are impaired.
  • the active energy ray-curable ink proposed in Patent Document 1 uses an alicyclic epoxy compound having an ester bond in the molecule, when the pigment concentration is increased, the coating film It is assumed that it is difficult for light to sufficiently reach the bottom. Therefore, the curing properties of the coating film are not sufficient, and it is difficult to maintain the adhesion of the cured coating film to the substrate when left under high temperature and high humidity conditions. It is expected that the hardness of the cured coating will also not meet the required standards.
  • the object of the present invention is to provide a curable resin composition that provides a highly cured coating film.
  • the present invention contains two types of epoxy compounds each having structural characteristics in a mass ratio within a specific numerical range, and further contains an oxetane compound, a photoacid generator, and a black colorant.
  • the inventors have discovered that the above problems can be solved by employing a curable resin composition, and have completed the present invention.
  • a curable resin composition comprising (A) an epoxy compound, (B) an oxetane compound, (C) a photoacid generator, and (D) a black colorant,
  • the epoxy compound (A) is (a) an alicyclic epoxy compound having an ester bond in the molecule and (b) an alicyclic epoxy compound having no ester bond in the molecule at a mass ratio in the numerical range of 5:100 to 30:100.
  • the curable resin composition of the present invention can be applied to an inkjet method.
  • the viscosity is preferably in the range of 5 to 20 mPa ⁇ s at 50°C, and preferably in the range of 5 to 15 mPa ⁇ s at 50°C. It is more preferable that it is within the range.
  • the viscosity can be measured using, for example, a cone plate viscometer (TVE-33H manufactured by Toki Sangyo Co., Ltd.).
  • a more preferred embodiment relates to a curable resin composition in which the alicyclic epoxy compound (b) having no ester bond in the molecule has a difunctional epoxy group.
  • the black colorant (D) is carbon black and is contained in an amount of 5 parts by mass or more based on a total of 100 parts by mass of the epoxy compound (A) and the oxetane compound (B).
  • the present invention relates to a synthetic resin composition.
  • Another preferred embodiment relates to a curable resin composition in which the mass ratio of the oxetane compound (B) to the epoxy compound (A) is in the numerical range of 2:100 to 40:100.
  • the epoxy compound (A) comprises (a) an alicyclic epoxy compound having an ester bond in the molecule, and (b) an alicyclic epoxy compound having no ester bond in the molecule. , in a mass ratio in the numerical range of 8:100 to 25:100. (a) By specifying the blending ratio of the alicyclic epoxy compound having an ester bond in the molecule within the above range, a cured coating film with excellent adhesion even after being left in high temperature and high humidity conditions is produced. be able to.
  • Another preferred embodiment relates to a curable resin composition in which the mass ratio of the oxetane compound (B) to the epoxy compound (A) is in the numerical range of 10:100 to 20:100.
  • B By regulating the blending ratio of the oxetane compound within the above range, the curability of the surface and bottom of the coating film can be improved in a well-balanced manner. By setting the ratio of the above-mentioned amount to be equal to or higher than the lower limit, the tackiness of the cured coating film after photocuring will be good.
  • the crosslinking density of the cured coating film can be maintained at an appropriate level, flexibility can be maintained, and the pencil hardness and adhesion after being left in high temperature and high humidity conditions can be improved.
  • Yet another preferred embodiment also relates to a curable resin composition that further contains an alkoxyanthracene derivative as a photosensitizer.
  • the OD value of the cured coating film at a film thickness of 10 to 20 ⁇ m is preferably 4 or more. , more preferably 5 or more.
  • the curable resin composition of the present invention having the above configuration not only has high light-shielding properties, but also has good curability on the surface of the coating film, and exhibits stable adhesion even under high temperature and high humidity conditions. It also has the excellent advantage of forming a cured coating film with high hardness. Furthermore, since the curable resin composition of the present invention is suitable for inkjet applications, it also has the advantage of good production efficiency in the production of various displays.
  • the curable resin composition of the present invention is also expected to be particularly suitable for use as a black light-shielding material for displays, for example, due to the above-mentioned properties.
  • the curable resin composition of the present invention contains (A) an epoxy compound in order to increase the hardness of the cured product (cured coating film) to be formed.
  • the curable resin composition of the present invention contains the (a) epoxy compound in the molecule in order to improve adhesion to the base material even when exposed to harsh environments of higher temperature and humidity. Two types of epoxy compounds are used together: an alicyclic epoxy compound having an ester bond, and (b) an alicyclic epoxy compound having no ester bond in the molecule.
  • an alicyclic epoxy compound is usually employed as one of the epoxy compounds due to its high reactivity.
  • an alicyclic epoxy compound having an ester bond it is customary to employ an alicyclic epoxy compound having an ester bond.
  • adhesion to the base material is not sufficient.
  • the present invention provides two epoxy compounds: (a) an alicyclic epoxy compound having an ester bond in the molecule; and (b) an alicyclic epoxy compound having no ester bond in the molecule.
  • a curable resin composition is prepared in which two kinds of epoxy compounds are used in combination, and in addition, these two kinds of epoxy compounds are mixed in a mass ratio in a numerical range of 5:100 to 30:100, preferably 8:100 to 25:100. By including it in the above, the above-mentioned disadvantages can be avoided.
  • an alicyclic epoxy compound having an ester bond in the molecule has one or more aliphatic ring structures in the molecule, and two carbon atoms and an oxygen atom in the aliphatic ring form an epoxy group. It refers to a compound with the following structure. And (a) the alicyclic epoxy compound having an ester bond in the molecule refers to a compound in which the above-mentioned alicyclic epoxy compound further has an ester bond in its chemical structure.
  • each compound having the following structure (In the formula, n1 represents an integer from 1 to 30) (In the formula, A represents an alkylene group having 1 to 8 carbon atoms; n2 represents an integer of 1 to 30) are preferred.
  • the alicyclic epoxy compound having an ester bond in the molecule may be used alone or in combination of two or more.
  • an alicyclic epoxy compound that does not have an ester bond in the molecule refers to the alicyclic epoxy compound described in the section of (a) the alicyclic epoxy compound that has an ester bond in the molecule above. However, it refers to a compound that does not have an ester bond in its molecule, such as an alicyclic epoxy compound that has an ether bond instead of an ester bond.
  • Examples of alicyclic epoxy compounds that do not have an ester bond in the molecule include compounds having the following structure: can be mentioned.
  • alicyclic epoxy compounds (b) having no ester bond in the molecule those having a difunctional epoxy group are more preferred in the present invention.
  • Such (b) alicyclic bifunctional epoxy compound having no ester bond in the molecule has the following structural formula in the molecule: Ethylene oxide group represented by and/or the following structural formula: It is a compound having a total of two cyclohexene oxide groups represented by Commercially available products include, for example, THI-DE, DE-102 and DE-103 (manufactured by JXTG Energy Corporation), and X-40-2678 and X-40-2669 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • the alicyclic epoxy compound having no ester bond in the molecule may be used alone or in combination of two or more.
  • the total content of (a) the alicyclic epoxy compound having an ester bond in the molecule in the curable resin composition of the present invention is determined from the viewpoints of curability and tackiness. It is preferably 3 to 60 parts by weight, more preferably 3 to 30 parts by weight, based on a total of 100 parts by weight of the compound.
  • the total content of (b) alicyclic epoxy compound that does not have an ester bond in the molecule is 100 parts by mass in total of (A) epoxy compound and (B) oxetane compound from the viewpoint of adhesion to the base material.
  • it is preferably 30 to 90 parts by weight, more preferably 40 to 80 parts by weight.
  • the respective contents of these two types of alicyclic epoxy compounds (a) and (b) need to be adjusted to a ratio within the specific numerical range as already described above.
  • the curable resin composition of the present invention comprises (a) an alicyclic epoxy compound having an ester bond in the molecule and (b) an alicyclic epoxy compound having no ester bond in the molecule, as well as
  • the epoxy compound (A) epoxy compounds other than (a) and (b), such as non-alicyclic epoxy
  • the other epoxy compounds that can be used in the present invention are commonly used, they are not all listed here, but preferable ones include Denacol EX-212 and Denacol EX-121 ( (all manufactured by Denacol), and KBM-403 (manufactured by Shin-Etsu Silicone).
  • the total content is the total of (A) epoxy compounds (including the epoxy compounds of (a) and (b) and other epoxy compounds) and (B) oxetane compounds (100 It is preferably 130 parts by weight, more preferably 3 to 20 parts by weight.
  • (B) Oxetane compound In the curable resin composition of the present invention, (B) an oxetane compound is contained as a thermosetting resin from the viewpoint of improving the hardness of the cured product.
  • the content of the (B) oxetane compound is the total amount of the above (A) epoxy compound, that is, (a) an alicyclic epoxy compound having an ester bond in the molecule; The mass ratio is adjusted to be within a specific numerical range with respect to the total amount of the alicyclic epoxy compound and other epoxy compounds that do not have an ester bond therein.
  • the content of the (B) oxetane compound is preferably such that the mass ratio of the (B) oxetane compound to the (A) epoxy compound is in the numerical range of 2:100 to 40:100. is adjusted to have a numerical value range of 10:100 to 20:100.
  • the oxetane compound (B) is not limited to monofunctional ones, but polyfunctional ones can also be used.
  • Examples of the monofunctional oxetane compound (B) include 3-methyloxetane, 3-ethyloxetane, 3-hydroxymethyloxetane, 3-methyl-3-hydroxymethyloxetane, and 3-ethyl-3-hydroxymethyloxetane. Can be mentioned.
  • polyfunctional oxetane compound (B) bis[(3-methyl-3-oxetanylmethoxy)methyl]ether, bis[(3-ethyl-3-oxetanylmethoxy)methyl]ether, 1,4-bis [(3-Methyl-3-oxetanylmethoxy)methyl]benzene, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, (3-methyl-3-oxetanyl)methyl acrylate, (3- Oxetane Examples include etherification products of alcohols with novolac resins, poly(p-hydroxystyrene), cardo-type bisphenols, calixarenes, calixresorcinarenes, or resins having hydroxyl groups such as silsesquioxane. Other examples include copolymers of unsaturated monomers having an oxetane ring and alkyl (meth)acrylates.
  • oxetane compound (B) It is of course possible to use a commercially available product as the oxetane compound (B).
  • OXT-101, OXT-121, OXT-212 and OXT-221 are preferred.
  • the curable resin composition of the present invention may contain one or more of the above (B) oxetane compounds.
  • the content of the oxetane compound (B) is preferably 3 to 40 parts by mass, and 8 to 30 parts by mass, based on the total of 100 parts by mass of the epoxy compound (A) and the oxetane compound (B), from the viewpoint of the hardness of the cured product. Parts by mass are more preferred. However, the content of the (B) oxetane compound needs to be adjusted so that the mass ratio to the mass of the contained (A) epoxy compound falls within the specific numerical range as described above.
  • the total amount of the epoxy compound (A) and the oxetane compound (B) is preferably 25 to 95% by mass, more preferably 35 to 90% by mass, based on the mass of the curable resin composition of the present invention.
  • the curable resin composition of the present invention contains (C) a photoacid generator as a compound capable of generating a substance that initiates cationic polymerization upon irradiation with ultraviolet rays.
  • C) Photoacid generators include, for example, onium salts such as diazonium salts, iodonium salts, bromonium salts, chloronium salts, sulfonium salts, selenonium salts, pyrylium salts, thiapyrylium salts, and pyridinium salts; tris(trihalomethyl)-s -halogenated compounds such as triazines and their derivatives; 2-nitrobenzyl esters of sulfonic acids; iminosulfonates; 1-oxo-2-diazonaphthoquinone-4-sulfonate derivatives; N-hydroxyimidosulfonates; tri(methanesulfonyloxy) ) benzen
  • C Commercially available products can be used as the photoacid generator, such as CPI-100P, CPI-200K, CPI-101A (manufactured by Sun-Apro), Cylacure photocuring initiator UVI-6990, Cylacure photocuring Initiator UVI-6992, Silacure photocuring initiator UVI-6976 (manufactured by Dow Chemical Japan Co., Ltd.), ADEKA OPTOMER SP-150, ADEKA OPTOMER SP-152, ADEKA OPTOMER SP-170, ADEKA OPTOMER SP -172 (manufactured by Asahi Denka Kogyo Co., Ltd.), CI-5102, CI-2855 (manufactured by Nippon Soda Co., Ltd.), Sun-Aid SI-60L, Sun-Aid SI-80L, Sun-Aid SI-100L, Sun-Aid SI-110L, Sun-Aid SI -180L, SunAid
  • CPI-100P, CPI-101A, CPI-200K, CPI-210S, or aromatic iodonium salts Omnicat 250, WPI-113, WPI-116, WPI-169 and WPI-170 are preferred.
  • the content of the photoacid generator (C) in the curable resin composition is preferably 5 to 30 parts by mass, and more preferably, It is 7 to 15 parts by mass.
  • the curable resin composition of the present invention preferably contains (D) a black colorant, particularly a black pigment, from the viewpoint that it is usually used for black light shielding.
  • black pigments such as carbon black are preferably used, but black dyes and other coloring agents may also be used within a range that does not deviate greatly from the viewpoint of the intended use, or in addition to carbon black. Of course, it may be further contained.
  • black pigments include, in addition to carbon black, inorganic pigments such as triiron tetroxide (Fe 3 O 4 ), black titanium oxide, copper manganese black, copper chrome black, and cobalt black, and cyanine black and aniline black.
  • inorganic pigments such as triiron tetroxide (Fe 3 O 4 ), black titanium oxide, copper manganese black, copper chrome black, and cobalt black, and cyanine black and aniline black.
  • organic pigments include organic pigments.
  • colorants having other colors include known and commonly used red, blue, green, and yellow pigments or dyes.
  • the content of the black colorant (D) in the curable resin composition of the present invention is adjusted in consideration of the use of the cured product to be formed, but from the viewpoint of the balance between curability and adhesion of the coating film, ( The content is preferably 5 parts by mass or more, more preferably 5 parts by mass or more and 15 parts by mass or less, based on a total of 100 parts by mass of A) the epoxy compound and (B) the oxetane compound.
  • the curable resin composition of the present invention preferably further contains a photosensitizer in order to further increase photosensitivity.
  • the photosensitizer is preferably a compound that becomes excited by light with a wavelength of 350 nm to 450 nm.
  • Examples include polynuclear aromatics such as pyrene, perylene, triphenylene, and anthracene; xanthenes such as fluorescein, eosin, erythrosin, rhodamine B, and rose bengal; xanthone such as xanthone, thioxanthone, dimethylthioxanthone, and diethylthioxanthone; Cyanines such as carbocyanine and oxacarbocyanine; merocyanines such as merocyanine and carbomerocyanine; rhodacyanines; oxonols; thiazines such as thionine, methylene blue and toluidine blue; acridines such as acridine orange, chloroflavin and acriflavin ; acridones such as acridone and 10-butyl-2-chloroacridone; anthraquinones;
  • UVS-1101 diethoxyanthracene; manufactured by Kawasaki Chemical Industries, Ltd.
  • Anthracure registered trademark
  • UVS-1221 dipropoxyanthracene; manufactured by Kawasaki Chemical Industries, Ltd.
  • alkoxyanthracene derivatives such as Anthracure (registered trademark) UVS-1331 (dibutoxyanthracene; manufactured by Kawasaki Chemical Industries, Ltd.).
  • the content of the photosensitizer is 0.1 to 2.0 parts by mass, preferably 0.2 to 1.0 parts by mass, per 1 part by mass of the photoacid generator.
  • the curable resin composition of the present invention may contain, for example, a solvent, a reactive diluent, a dispersant, a thickener, a surfactant, an antioxidant, a plasticizer, a flame retardant, within a range that does not impair its properties.
  • Other components such as antistatic agents, leveling agents, antifoaming agents, and antibacterial agents may also be contained.
  • a photoreactive diluent is preferable.
  • photoreactive diluents include (meth)acrylates, vinyl ethers, ethylene derivatives, styrene, chloromethylstyrene, ⁇ -methylstyrene, maleic anhydride, dicyclopentadiene, N-vinylpyrrolidone, N-vinylformamide, and xylene.
  • examples include compounds having an unsaturated double bond, an oxetanyl group, and an epoxy group, such as dioxetane, oxetane alcohol, 3-ethyl-3-(phenoxymethyl)oxetane, and resorcinol diglycidyl ether.
  • (meth)acrylates are preferred.
  • the curable resin composition of the present invention is applied to a target location on a substrate by an inkjet method, and is cured to form a cured product.
  • a suitable inkjet printing method is an on-demand piezo method, but the method is not particularly limited.
  • Suitable wavelengths include 365 nm, 385 nm, 395 nm, 405 nm, etc. in the ultraviolet region, but are not particularly limited. Curing is performed by irradiating the applied composition with active energy radiation.
  • Suitable light sources for irradiating active energy rays include LEDs, low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, metal halide lamps, and the like.
  • electron beams, ⁇ rays, ⁇ rays, ⁇ rays, X rays, neutron beams, etc. can also be used.
  • the number of irradiation light sources is one or two or more, and in the case of two or more, it is of course possible to use a combination of light sources of different wavelengths.
  • the amount of exposure to active energy rays is usually in the range of 10 to 10,000 mJ/cm 2 , preferably 20 to 2,000 mJ/cm 2 , and more preferably 100 to 2,000 mJ/cm 2 .
  • each component was blended and premixed using a stirrer to prepare curable resin compositions for Examples 1 to 10 and Comparative Examples 1 to 4.
  • the numerical values of the blending amounts in the table indicate parts by mass unless otherwise specified.
  • curable resin compositions of Examples 1 to 10 and Comparative Examples 1 to 4 cured products (cured coating films) with a film thickness of 5 ⁇ m were obtained, and the cured products were subjected to cross-cutting, pencil cutting, etc. as described below. Hardness and dryness to touch after UV curing were measured.
  • the viscosity of the curable resin compositions of Examples 1 to 10 and Comparative Examples 1 to 4 was determined by measuring the viscosity at an ink temperature of 50°C and 100 rpm using a cone plate viscometer (TVE-33H manufactured by Toki Sangyo Co., Ltd.). However, in all cases, the pressure was in the range of 5 to 20 mPa ⁇ s.
  • the cross-cuts were made after being left at 23°C and 50% RH for 3 hours (initial adhesion) and after being placed in a constant temperature and humidity chamber (Espec LHL-114) under the conditions of 85°C and 85% relative humidity. ) and after standing for 240 hours (85° C., 85% RH in close contact).
  • the evaluation criteria are as follows.
  • the evaluation criteria other than " ⁇ " and "x" indicate that the adhesion between the cured coating film and the test substrate is good, and the evaluation criteria of " ⁇ " indicates that the adhesion is particularly good.
  • ⁇ The grid remains 100% adhered after peeling, and no chipping is observed.
  • ⁇ The grid remains 100% adhered after peeling, and slight chipping is observed at the intersection of the grids.
  • ⁇ The squares after peeling remain 100% attached, and peeling occurs at the intersections of the squares.
  • Table 2 The results are shown in Table 2 below.
  • the OD value of each Example and each Comparative Example with a film thickness of 10 ⁇ m after curing was 4 or more and 6 or less
  • the OD value of each Example and each Comparative Example with a film thickness of 20 ⁇ m after curing was 6 or more.
  • the OD value was sufficient for use as a black light shielding agent.
  • the film thickness after curing 10 ⁇ m or 20 ⁇ m was formed by drawing on an inkjet printer every 5 ⁇ m using the same method as in [Preparation of test substrate], then curing with UV, and stacking up to a predetermined film thickness. It is.
  • the mass ratio of (a) an alicyclic epoxy compound having an ester bond in the molecule and (b) an alicyclic epoxy compound having no ester bond in the molecule is in a more preferable range of 8:100 to 25: 100, and the mass ratio of the (B) oxetane compound and the (A) epoxy compound was set to a more preferable range of 10:100 to 20:100.
  • Example 1 Example 3, Example 5, Example 6 had the best results among the evaluation criteria. In particular, the results were better than other examples in terms of cross-cutting (85° C., 85% RH adhesion) and pencil hardness under high temperature and high humidity conditions.
  • the mass ratio of (a) an alicyclic epoxy compound having an ester bond in the molecule and (b) an alicyclic epoxy compound having no ester bond in the molecule is outside the range of 43:100 to 50. :100
  • Comparative Example 3 which does not contain an alicyclic epoxy compound having an ester bond in the molecule (a) was slightly inferior in cross-cut (initial adhesion) and Regarding cross-cutting under high humidity conditions (adhesion at 85° C. and 85% RH), the cured coating film peeled off, resulting in the worst result among the evaluation criteria.
  • Comparative Examples 1 to 3 had the worst results in terms of pencil hardness among the evaluation criteria.
  • Comparative Example 4 had good cross-cut evaluation results, but pencil hardness and tack had the worst results among the evaluation criteria.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

[Problème] Fournir une composition de résine durcissable pour la protection contre la lumière noire pour un jet d'encre, la composition de résine durcissable ayant une excellente aptitude au durcissement de surface en plus de propriétés de protection contre la lumière élevées, présentant une adhérence stable dans des conditions de température élevée et d'humidité élevée, et produisant un film de revêtement durci ayant une dureté élevée après durcissement. [Solution] Composition de résine durcissable contenant (A) un composé époxy, (B) un composé oxétane, (C) un photogénérateur d'acides, et (D) un colorant noir, le composé époxy (A) contenant (a) un composé époxy alicyclique ayant une liaison ester dans chaque molécule et (b) un composé époxy alicyclique n'ayant pas de liaison ester dans chaque molécule dans un rapport de masse dans une plage numérique de 5:100 à 30:100. [Selected drawing] None
PCT/JP2023/011812 2022-03-24 2023-03-24 Composition de résine durcissable WO2023182495A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022-048515 2022-03-24
JP2022048515 2022-03-24

Publications (1)

Publication Number Publication Date
WO2023182495A1 true WO2023182495A1 (fr) 2023-09-28

Family

ID=88101663

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/011812 WO2023182495A1 (fr) 2022-03-24 2023-03-24 Composition de résine durcissable

Country Status (2)

Country Link
TW (1) TW202346404A (fr)
WO (1) WO2023182495A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1161034A (ja) * 1997-08-15 1999-03-05 Kansai Paint Co Ltd 塗料組成物およびその塗装法
JP2000144043A (ja) * 1998-11-09 2000-05-26 Toyo Ink Mfg Co Ltd 紫外線硬化型塗料、及びその利用
JP2005194453A (ja) * 2004-01-09 2005-07-21 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インクジェットインクとそれを用いた画像形成方法及びインクジェット記録装置
JP2005264098A (ja) * 2004-03-22 2005-09-29 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物とそれを用いた画像形成方法及びインクジェット記録装置
JP2008138113A (ja) * 2006-12-04 2008-06-19 Konica Minolta Medical & Graphic Inc 硬化型組成物、活性エネルギー線硬化型組成物、インク、活性エネルギー線硬化型インクジェットインク及び画像形成方法
JP2014196475A (ja) * 2013-03-04 2014-10-16 株式会社ダイセル 感光性樹脂組成物及びその硬化物、並びに光学部品
WO2021049331A1 (fr) * 2019-09-12 2021-03-18 太陽インキ製造株式会社 Composition durcissable pour jet d'encre
WO2022059395A1 (fr) * 2020-09-17 2022-03-24 株式会社Adeka Composition, produit durci et procédé de production de produit durci

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1161034A (ja) * 1997-08-15 1999-03-05 Kansai Paint Co Ltd 塗料組成物およびその塗装法
JP2000144043A (ja) * 1998-11-09 2000-05-26 Toyo Ink Mfg Co Ltd 紫外線硬化型塗料、及びその利用
JP2005194453A (ja) * 2004-01-09 2005-07-21 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インクジェットインクとそれを用いた画像形成方法及びインクジェット記録装置
JP2005264098A (ja) * 2004-03-22 2005-09-29 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物とそれを用いた画像形成方法及びインクジェット記録装置
JP2008138113A (ja) * 2006-12-04 2008-06-19 Konica Minolta Medical & Graphic Inc 硬化型組成物、活性エネルギー線硬化型組成物、インク、活性エネルギー線硬化型インクジェットインク及び画像形成方法
JP2014196475A (ja) * 2013-03-04 2014-10-16 株式会社ダイセル 感光性樹脂組成物及びその硬化物、並びに光学部品
WO2021049331A1 (fr) * 2019-09-12 2021-03-18 太陽インキ製造株式会社 Composition durcissable pour jet d'encre
WO2022059395A1 (fr) * 2020-09-17 2022-03-24 株式会社Adeka Composition, produit durci et procédé de production de produit durci

Also Published As

Publication number Publication date
TW202346404A (zh) 2023-12-01

Similar Documents

Publication Publication Date Title
JP4667145B2 (ja) 光硬化型樹脂組成物及びそれからなるプラスチック用樹脂組成物
JP6610253B2 (ja) 熱硬化性樹脂組成物、硬化膜、硬化膜付き基板および電子部品
TWI643917B (zh) 單體組成物及含有該單體組成物之硬化性組成物
KR102142179B1 (ko) 잉크젯용 적외선 투과 잉크 조성물, 이를 이용한 베젤 패턴의 형성방법, 이에 따라 제조한 베젤 패턴 및 이를 포함하는 디스플레이 기판
WO2021049331A1 (fr) Composition durcissable pour jet d'encre
JPWO2005085317A1 (ja) 紫外線硬化型組成物
KR20100065115A (ko) 공중합체 및 감광성 수지 조성물
JP2016115779A (ja) ナノインプリント用光硬化性組成物
JP6729684B2 (ja) 熱硬化性樹脂組成物、硬化膜、硬化膜付き基板および電子部品
TW201527453A (zh) 光陽離子硬化性噴墨墨水、光陽離子硬化性噴墨墨水之製造方法、印刷物及印刷物之製造方法
JPWO2008153076A1 (ja) 基板貼り合わせ用光学接着剤、及び、基板貼り合わせ用光学接着剤硬化体
JP5234562B2 (ja) 感光性組成物
KR20140111051A (ko) 활성 에너지선 경화성 조성물, 그 경화물 및 용도
WO2017177797A1 (fr) Applications de nouveau système de photodurcissement cationique, et composition associée
JP6534869B2 (ja) モノマー組成物、及びそれを含む硬化性組成物
TW201609999A (zh) 單體組成物及含有該單體組成物之硬化性組成物
JP7455669B2 (ja) インクジェット用硬化性組成物
JP2020514496A (ja) フォルダブルディスプレイの紫外線硬化型ブラックインク組成物及びそれを用いたベゼルパターンの形成方法
TWI797344B (zh) 顯示元件用密封劑及其硬化物
JP2007302808A (ja) 活性エネルギー線硬化性インクおよび印刷物
WO2023182495A1 (fr) Composition de résine durcissable
ES2349430T3 (es) Composición de revestimiento endurecibles mediante energía.
JP2005336349A (ja) カチオン重合型組成物
JP2020537016A (ja) フィルム印刷可能な紫外線硬化型インク組成物、それを用いたベゼルパターンの製造方法、それによって製造したベゼルパターン及びそれを含むフォルダブルディスプレイ基板
JP7446919B2 (ja) インクジェット用硬化性組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23775088

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2024509259

Country of ref document: JP

Kind code of ref document: A