WO2015115293A1 - Composition durcissable par rayons actiniques pour un matériau de plancher - Google Patents

Composition durcissable par rayons actiniques pour un matériau de plancher Download PDF

Info

Publication number
WO2015115293A1
WO2015115293A1 PCT/JP2015/051641 JP2015051641W WO2015115293A1 WO 2015115293 A1 WO2015115293 A1 WO 2015115293A1 JP 2015051641 W JP2015051641 W JP 2015051641W WO 2015115293 A1 WO2015115293 A1 WO 2015115293A1
Authority
WO
WIPO (PCT)
Prior art keywords
active energy
energy ray
curable composition
flooring
compound
Prior art date
Application number
PCT/JP2015/051641
Other languages
English (en)
Japanese (ja)
Inventor
川合　一成
晋吾 草野
Original Assignee
Dic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 Dic株式会社 filed Critical Dic株式会社
Publication of WO2015115293A1 publication Critical patent/WO2015115293A1/fr

Links

Classifications

    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
    • E04F15/00—Flooring
    • E04F15/02—Flooring or floor layers composed of a number of similar elements
    • E04F15/10—Flooring or floor layers composed of a number of similar elements of other materials, e.g. fibrous or chipped materials, organic plastics, magnesite tiles, hardboard, or with a top layer of other materials
    • E04F15/105—Flooring or floor layers composed of a number of similar elements of other materials, e.g. fibrous or chipped materials, organic plastics, magnesite tiles, hardboard, or with a top layer of other materials of organic plastics with or without reinforcements or filling materials

Definitions

  • the present invention relates to an active energy ray-curable composition for flooring and a construction method using the same.
  • the active energy ray-curable composition is a composition that is instantly cured by a crosslinking reaction when irradiated with an active energy ray, and can impart excellent stain resistance by being coated on a flooring material.
  • an apparatus that requires high power such as a high-pressure mercury lamp or a metal halide lamp as an active energy ray source. The running cost was high because it was cured with
  • UV-LED light emitting diode
  • the UV-LED light source has a longer light source life and is greatly superior in energy saving compared with existing UV lamp light sources such as low-pressure, high-pressure mercury lamps, xenon lamps, metal halide lamps and other ultraviolet lamps. The practical application of this is strongly requested by various companies in various industries.
  • a disadvantage of the UV-LED light source is that the film drying property of the active energy ray-curable composition is greatly inferior to that of the lamp light source, and this method is an obstacle that does not spread.
  • the reason for this is that although there are diodes with shorter wavelengths for testing at present, practical UV-LED light sources have a light emission wavelength range limited to 365 to 420 nm, and emit conventional ultraviolet light having a wide wavelength range. The total amount of ultraviolet energy is smaller than that of the UV lamp light source, and the amount of radicals generated from the photopolymerization initiator is small, so that the polymerization reaction is susceptible to oxygen inhibition.
  • the active energy ray-curable composition obtained by irradiating the active energy ray from the UV-LED light source generally tends to have poor curability on the surface of the film. Has been confirmed.
  • the reason for the poor curing of the active energy ray-curable composition for flooring is that many photopolymerization initiators that react favorably with UV-LEDs tend to turn yellow during the reaction and contain pigments.
  • the effect of yellowing is not a major problem with colored active energy ray-curable compositions, but it is practical for active and transparent ray energy curable compositions for colorless and transparent flooring, since the yellowing of the coating film is noticeable. In order to suppress yellowing to such a range, the type and amount of the photopolymerization initiator are greatly limited.
  • the object of the present invention is to provide sufficient physical properties and robust physical properties by irradiating active energy rays with a UV-LED light source having a peak wavelength at 350 to 420 nm while maintaining the conventional physical performance. It is providing the active energy ray-curable composition for flooring agents for obtaining. Moreover, it is providing the construction method which uses the said active energy ray curable composition for flooring.
  • the present inventors have found that the above problems can be achieved by employing a combination of an active energy ray polymerizable compound having an ethylenic double bond and a specific photopolymerization initiator. It came to.
  • the present invention comprises an active energy ray-curable composition for flooring, which comprises an active energy ray-polymerizable compound (A) having an ethylenic double bond and an acylphosphine oxide photopolymerization initiator (B). Offer things.
  • the present invention also provides an active energy ray-curable composition for flooring, further containing a thioxanthone compound (C).
  • the present invention further provides an active energy ray-curable composition for flooring, which further contains a tertiary amine compound (D) selected from aliphatic amine derivatives and / or benzoic acid amine derivatives.
  • D tertiary amine compound
  • the present invention provides an active energy ray in which the total of the acylphosphine oxide photopolymerization initiator (B), the thioxanthone compound (C), and the tertiary amine compound (D) has the ethylenic double bond.
  • an active energy ray-curable composition for flooring that is 5 to 15% by weight based on the total amount of the polymerizable compound (A).
  • the weight ratio of the total content of the acylphosphine oxide photopolymerization initiator (B), the thioxanthone compound (C) and the tertiary amine compound (D) is 1: 1 to 15: 1.
  • the present invention provides the acylphosphine oxide photopolymerization initiator (B) wherein 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and / or bis (2,4,6-trimethylbenzoyl) -phenylphosphine.
  • An active energy ray-curable composition for flooring that is a fin oxide is provided.
  • this invention also provides the construction method which hardens the said floor material active energy ray curable composition using a movable active energy ray irradiation apparatus.
  • the present invention also provides a flooring obtained by the construction method.
  • the present invention also provides a floor using the floor material obtained by the construction method.
  • the floor material having sufficient curability equivalent to the case of curing with a conventional UV lamp light source.
  • An active energy ray-curable composition can be obtained.
  • an active energy ray-polymerizable compound (A) having an ethylenic double bond is an essential component.
  • Specific examples thereof include the following active energy ray polymerizable compounds.
  • active energy ray-polymerizable compound having an ethylenic double bond As the active energy ray-polymerizable compound (A) having an ethylenic double bond used in the present invention, known (meth) acrylic monomers and / or (meth) acrylic that are usually used in active energy ray-curable compositions. Any oligomer can be selected and used. In the present invention, “(meth) acryl” is a general term for acrylic and methacrylic.
  • (meth) acrylic monomers include unsaturated carboxylic acids such as acrylic acid and methacrylic acid or esters thereof, such as alkyl-, cycloalkyl-, halogenated alkyl-, alkoxyalkyl-, hydroxyalkyl-, aminoalkyl-, allyl.
  • the (meth) acrylic monomer polyethylene glycol having an ethylene glycol unit in the molecule (n is 3 or more, approximately 14 or less) di (meth) acrylate, trimethylolpropane EO modification (n is 3 or more) And approximately 14 or less) tri (meth) acrylate, phenol EO-modified (n is 3 or more and approximately 14 or less) (meth) acrylate, 2-hydroxyethyl (meth) acrylate having a hydroxyl group in the molecule, 2 -Hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, pentaerythritol tri (meth) acrylate, monohydroxyethyl (meth) acrylate phthalate and the like.
  • These (meth) acrylic monomers may be used alone or in combination of two or more.
  • cyclopentadienyl (meth) acrylate dicyclopentadienyl oxyethyl (meth) acrylate, dihydrodicyclopentadienyl (meth) acrylate such as a (meth) acrylic monomer.
  • active energy ray polymerizable compounds may be used alone or in combination of two or more.
  • Examples of the active energy ray polymerizable compound particularly suitable for the composition include methyl, ethyl, propyl, butyl, amyl, 2-ethylhexyl, isooctyl, nonyl, dodecyl, hexadecyl, octadecyl, cyclohexyl, benzyl, methoxyethyl, and butoxyethyl.
  • the oligomer contained in the active energy ray-curable composition for flooring according to the embodiment is a compound that is crosslinked or polymerized by irradiation with light. Moreover, although it is a compound which has a polymer of a monomer as a principal chain, the number of monomers which comprise a principal chain is not limited. The molecular weight of the oligomer is preferably in the range of 500 to 20,000.
  • the number of functional groups of the oligomer is preferably 2-20, more preferably 4-20, and even more preferably 6-20.
  • the functional group possessed by the oligomer is a photopolymerizable functional group.
  • the photopolymerizable functional group is a carbon-carbon double bond such as an acryloyl group.
  • the glass transition temperature (Tg) of the oligomer is preferably 40 ° C. or higher, more preferably 50 ° C. or higher, and even more preferably 70 ° C. or higher.
  • the glass transition temperature (Tg) can be measured by differential scanning calorimetry (DSC), thermomechanical analysis (TMA), or the like.
  • the viscosity of the oligomer is not particularly limited, but the viscosity at 25 ° C. is preferably from 100 to 10000 mPa ⁇ s in consideration of the influence on the handleability of the active energy ray-curable composition and the viscosity, and 5000 mPa ⁇ s. The following is preferable, and 1000 mPa ⁇ s or less is more preferable.
  • the main chain of the oligomer can be polyepoxy, aliphatic polyurethane, aromatic polyurethane, aliphatic polyester, aromatic polyester, polyamine, polyacrylate and the like.
  • the aforementioned photopolymerizable functional group is preferably added to the main chain of the oligomer.
  • the functional group of the oligomer can be introduced by reacting the following (photopolymerizable) functional group-containing compound with the main chain of the oligomer.
  • (photopolymerizable) functional group-containing compounds include (meth) acrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid and other unsaturated carboxylic acids and their salts or esters, urethanes, amides and anhydrides thereof.
  • an N-vinyl compound may be included.
  • N-vinyl compounds include N-vinylformamide, N-vinylcarbazole, N-vinylacetamide, N-vinylpyrrolidone, N-vinylcaprolactam, acryloylmorpholine, and derivatives thereof.
  • Tg glass transition temperature
  • the oligomer may be a linear oligomer, a branched oligomer, or a dendritic oligomer, but may be preferably a branched oligomer or a dendritic oligomer. Since the branched-chain oligomer and the dendritic oligomer have a relatively low viscosity, the hardness of the cured film can be increased although it is difficult to increase the viscosity of the active energy ray-curable composition for flooring.
  • a dendritic oligomer means an oligomer having a plurality of branched chains in one molecule.
  • dendritic oligomers examples include dendrimers, hyperbranched oligomers, star oligomers and graft oligomers.
  • Dendrimers, hyperbranched oligomers, star oligomers and graft oligomers may be known compounds. Among these, a dendrimer and a hyperbranched oligomer are preferable, and a hyperbranched oligomer is more preferable. Dendrimers and hyperbranched oligomers are less likely to increase the viscosity of the active energy ray-curable composition.
  • Hyperbranched oligomer refers to an oligomer in which a plurality of photopolymerizable functional groups are bonded to an oligomer in which two or more monomers are bonded as repeating units. Hyperbranched oligomers generally contain a large number of photopolymerizable functional groups. Therefore, the hyperbranched oligomer can further increase the curing rate of the active energy ray-curable composition for flooring, and can further increase the hardness of the cured film.
  • the number of photopolymerizable functional groups in one molecule of hyperbranched oligomer is preferably 6 or more.
  • hyperbranched oligomers examples include polyester 6-functional acrylate, polyester 9-functional acrylate, polyester 16-functional acrylate, and the like.
  • Examples of commercially available oligomer products include the following. CN131B, CN292, CN2272, CN2303, CN2304, CN509, CN551, CN790, CN2400, CN2401, CN2402, CN9011, CN9026 (all manufactured by Sartomer Company, Inc.), EBECRYL600, EBECRYL605, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL1830, EBECRYL80, EBECRYL8210, EBECRYL 8301 (above Daicel Cytec), Ecure 6147, Ecure 6172-1, Ecure 6153-1, Ecure 6175-3, Ecure 6234, Ecure 6237 (Eternal Chemical co., LT) )
  • hyperbranched oligomers examples include the following. CN2300, CN2301, CN2302, CN2303 (above Sartomer), Ecure 6361-100, Ecure 6362-100 (above Eternal Chemical co., LTD), V # 1000, V # 1020 (Osaka Organic Chemical Industries, Ltd.)
  • the active energy ray-curable composition for flooring of the present invention must contain the acylphosphine oxide polymerization initiator (B) as a photopolymerization initiator.
  • Acylphosphine oxide polymerization initiators include bis- (2,6-dichlorobenzoyl) phenylphosphine oxide, bis- (2,6-dichlorobenzoyl) -2,5-dimethylphenylphosphine oxide, bis- ( 2,6-dichlorobenzoyl) -4-propylphenylphosphine oxide, bis- (2,6-dichlorobenzoyl) -1-naphthylphosphine oxide, bis- (2,6-dimethoxybenzoyl) phenylphosphine oxide, bis -(2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis- (2,6-dimethoxybenzoyl) -2,5-dimethylphenylphosphine oxide, bis- (2,4,4) 6-Trimethylbenzoyl
  • 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and bis- (2,4,6-trimethylbenzoyl) -phenylphosphine oxide are By having a UV absorption wavelength which matches the emission wavelength region of the diode, suitable curing property is obtained, and, more preferred from the viewpoint yellow cured film variable is small.
  • a more suitable curability can be obtained by using a photosensitizer in combination.
  • the photosensitizer capable of reacting with a 350-420 nm UV-LED include thioxanthone compounds (C).
  • thioxanthone, 2,4-diethylthioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 1- Chloro-4-propoxythioxanthone and the like can be mentioned, and the amount used is limited to a small amount in consideration of the yellowing property. However, when used in combination, the film curability can be preferably improved.
  • a tertiary amine compound (D) other than the above-described amine-modified acrylate as a hydrogen donor.
  • Active energy ray curing can be obtained.
  • amines of aniline derivatives include N, N-dihydroxyethylaniline, N, N-dimethylaniline, N, N-diethylaniline, and N, N-dimethyl-p-toluidine.
  • the amount of these photosensitizers used is 2.0 mass% or less in the active energy ray-curable composition for flooring in the case of the thioxanthone compound (C).
  • the content is preferably 4% by mass or less.
  • the total of the acylphosphine oxide photopolymerization initiator (B), the thioxanthone compound (C), and the tertiary amine compound (D) is the active energy ray-polymerizable having the ethylenic double bond. It is preferably in the range of 5 to 15% by weight relative to the total amount of compound (A).
  • the addition amount is less than 5% by weight, it is difficult to obtain good curability, and when the addition amount exceeds 15% by weight, the initiator amount becomes excessive, the solubility is lowered, and the fluidity of the composition is also lowered.
  • the weight ratio of the total content of the acylphosphine oxide photopolymerization initiator (B), the thioxanthone compound (C) and the tertiary amine compound (D) is in the range of 1: 1 to 15: 1. It is preferable.
  • Mixture of tic acid 2- [2 [oxo-2-phenyl-acetoxy-ethoxy-]-ethyl ester and oxy-phenyl-acetic acid 2- [2-hydroxy-ethoxy] -ethyl ester, phenylglyoxylic acid methyl examples include esters and the like, and although there is some degree of yellowing, the acylphosphine oxide polymerization initiator (A) can be used in combination.
  • a photopolymerization initiator that absorbs light other than the emission wavelength of the UV-LED may be added as necessary.
  • benzoin isobutyl ether and other molecular cleavage types include 1-hydroxycyclohexyl phenyl ketone, benzoin ethyl ether, benzyl dimethyl ketal, methyl benzoyl formate, 2-hydroxy-2-methyl-1- Phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one and 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1- ON or the like may be used in combination, and hydrogen abstraction type photopolymerization initiators such as benzophenone, 4-phenylbenzophenone, isophthalphenone, 4-benzoyl-4′-methyl-diphenyl sulfide, etc. may be used in combination.
  • the active energy ray-curable composition for flooring of the present invention can be made more excellent in scratch resistance by adding organic particles or inorganic particles.
  • organic particles used in the present invention include acrylic resin, urethane resin, fluororesin, silicone, melamine resin, styrene resin, and inorganic particles include calcium carbonate, silica, alumina, titanium oxide, magnesium hydroxide, zinc oxide. , Calcium silicate, aluminum hydroxide, and the like. These can be used alone or in combination, but alumina is preferably used.
  • the average particle size of the organic particles and inorganic particles is preferably 10 ⁇ m or less.
  • the organic particles and inorganic particles may be added as a single particle, or may be added after being dispersed in a suitable dispersion medium in advance.
  • the addition amount of the organic particles and the inorganic particles is preferably 10 parts by weight or less, more preferably 1 to 5 parts by weight with respect to 100 parts by weight of the active energy ray polymerizable compound.
  • the active energy ray-curable composition for flooring can be colored to impart design properties.
  • inorganic pigments and organic pigments can be used as known and commonly used colorants.
  • an inorganic pigment or an organic pigment can be used.
  • Inorganic pigments include silicas such as alkaline earth metal sulfates, carbonates, finely divided silicic acid, synthetic silicates, calcium silicates, alumina, hydrated alumina, titanium oxide, zinc oxide, talc, clay, etc.
  • An inorganic pigment, iron oxide, or carbon black produced by a known method such as a contact method, a furnace method, or a thermal method can be used.
  • Organic pigments include azo pigments (including azo lakes, insoluble azo pigments, condensed azo pigments, chelate azo pigments), polycyclic pigments (for example, phthalocyanine pigments, perylene pigments, perinone pigments, anthraquinone pigments, quinacridone pigments, dioxazines). Pigments, thioindigo pigments, isoindolinone pigments, quinofullerone pigments, etc.), dye chelates (for example, basic dye chelates, acidic dye chelates, etc.), nitro pigments, nitroso pigments, aniline black, and the like.
  • azo pigments including azo lakes, insoluble azo pigments, condensed azo pigments, chelate azo pigments
  • polycyclic pigments for example, phthalocyanine pigments, perylene pigments, perinone pigments, anthraquinone pigments, quinacridone pigments, dioxazines.
  • pigments include carbon black, No. manufactured by Mitsubishi Chemical Corporation. 2300, no. 900, no. 960, MCF88, No. 33, no. 40, no. 45, no. 52, MA7, MA8, MA100, no. 2200B, etc. are Raven 5750, 5250, 5000, 3500, 1255, 700, etc. manufactured by Columbia, and Regal 400R, 330R, 660R, Mogulu L, 700, Monarch 800, 880, manufactured by Cabot, The same 900, 1000, 1100, 1300, 1300, 1400, etc.
  • the pigment used for the yellow color is C.I. I. Pigment Yellow 1, 2, 3, 12, 13, 14, 16, 17, 73, 74, 75, 83, 93, 95, 97, 98, 109, 110, 114, 120, 128, 129, 138, 150, 151, 154, 155, 180, 185, 213 and the like.
  • pigments used for magenta color C.I. I. Pigment Red 5, 7, 12, 48 (Ca), 48 (Mn), 57 (Ca), 57: 1, 112, 122, 123, 168, 184, 202, 209, C.I. I. And CI Pigment Violet 19.
  • pigments used for cyan C.I. I. And CI Pigment Blue 1, 2, 3, 15: 3, 15: 4, 60, 16, and 22.
  • C.I. I. Pigment White 6, 18, 21 and the like can be used depending on the purpose, but titanium oxide having a high hiding power is preferable.
  • titanium oxide having a high hiding power is preferable.
  • additives such as photosensitizers, antifoaming agents, leveling agents, ultraviolet absorbers, light stabilizers, lubricants, and matting materials are added to the active energy ray-curable composition for flooring. be able to.
  • an antibacterial agent, an antistatic agent, etc. can be suitably added as needed for the purpose of providing functionality.
  • the active energy ray-curable composition for flooring of the present invention includes hydroquinone, methoquinone, hindered amine light stabilizer, hindered phenol light stabilizer, di-t-butyl hydroquinone, P—
  • a polymerization inhibitor such as methoxyphenol, butylhydroxytoluene or nitrosamine salt may be added to the active energy ray-curable composition for flooring in the range of 0.01 to 2% by mass.
  • Dispersants include Ajimoto PB821, PB822, PB881, PB817 manufactured by Ajinomoto Fine-Techno Co., Ltd., Solspers 24000GR manufactured by Lubrizol Co., Ltd., 32000, 33000, 36000, 39000, 41000, 71000, EFKA-7701 manufactured by BASF Corporation Examples include, but are not limited to, Disparon DA-703-50, DA-705, DA-725, etc.
  • the amount of the dispersant used is preferably in the range of 10 to 80% by weight, particularly preferably in the range of 20 to 60% by weight with respect to the filler.
  • the amount used is less than 10% by weight, the dispersion stability tends to be insufficient, and when it exceeds 80% by weight, the viscosity of the active energy ray-curable composition for flooring tends to be high, The leveling property of the active energy ray-curable composition for flooring is lowered.
  • non-reactive resins such as acrylic resin, epoxy resin, terpene phenol resin, rosin ester, and the like can be blended for the purpose of imparting adhesiveness to the substrate to be printed.
  • An active energy ray-curable composition can be obtained by blending the necessary active energy ray-polymerizable compound and heating while stirring and mixing the photopolymerization initiator and the photopolymerization inhibitor.
  • an additive such as a surface tension adjusting agent or a lubricant necessary for the active energy ray-curable composition for flooring is further added and stirred.
  • an active energy ray-curable composition can be obtained.
  • the viscosity of the active energy ray-curable composition for flooring in the present invention is preferably 50 to 1000 mPa ⁇ sec, and is preferably 100 to 1000 mPa ⁇ sec, because if the viscosity is too high, streaks may occur in the finished product after curing. 400 mPa ⁇ sec is most preferable.
  • the application method of the active energy ray-curable composition for flooring is applied using a roller, a brush or the like.
  • the active energy ray-curable composition for flooring can be used for various inks and coating applications.
  • Coating methods include, for example, roll coaters, gravure coaters, flexo coaters, air doctor coaters, blade coaters, air knife coaters, squeeze coaters, impregnation coaters, transfer roll coaters, kiss coaters, curtain coaters, cast coaters, spray coaters, die coaters, and offsets.
  • Known means such as a printing machine or a screen printing machine can be appropriately employed.
  • the active energy ray-curable composition for flooring is subjected to a curing reaction by irradiation with active energy rays, preferably light such as ultraviolet rays.
  • active energy rays preferably light such as ultraviolet rays.
  • a light source such as an ultraviolet ray
  • a light source usually used for a UV curable coating agent for example, a metal halide lamp, a xenon lamp, a carbon arc lamp, a chemical lamp, a low pressure mercury lamp, a high pressure mercury lamp can be cured without any problem.
  • a commercially available product such as an H lamp, D lamp, or V lamp manufactured by Fusion System can be used.
  • an active energy ray-curable composition for flooring by using an active energy ray irradiation source such as a UV-LED or an ultraviolet light emitting semiconductor laser.
  • an active energy ray irradiation source such as a UV-LED or an ultraviolet light emitting semiconductor laser.
  • the active energy ray is irradiated with an active energy ray having a wavelength peak in the range of 365 to 420 nm using a light emitting diode (LED). It is possible to form a flooring by curing the linear curable composition.
  • LED light emitting diode
  • a light source that emits the active energy ray preferably ultraviolet rays
  • a main body supported by two or more frames and at least a wheel that contacts a flooring. It is fixed to the frame.
  • the wheel that contacts the floor material passes through the area where the active energy ray is irradiated and passes over the active energy ray-curable composition cured by the active energy ray, so there is no defect such as a wheel mark. .
  • the light source of the movable active energy ray irradiation apparatus used in the present invention uses a UV-LED.
  • UV-LEDs are preferably water-cooled because UV-LEDs generate heat more easily, but are preferably air-cooled when the movable active energy ray irradiation device is small.
  • the movable active energy ray irradiation apparatus preferably includes a mechanism for satisfying the curing condition when the active energy ray is irradiated. For that purpose, it is more preferable to provide a mechanism capable of automatically controlling the moving speed, or a mechanism for notifying when the moving speed is too fast.
  • Example 1 Preparation of active energy ray-curable composition (1) for flooring
  • a high-pressure mercury lamp is applied to the U -Active energy ray curing for flooring by irradiating active energy rays (irradiation amount: 500 mJ / cm 2 ) with a movable active energy ray irradiation device TIGER made by HIDUltraviolet, LLC, replaced with FirePower, a UV-LED made by VIX
  • the flooring composition was obtained by curing the composition.
  • Oligo (2-hydroxy-2-methyl-1- (4- (methylvinyl) phenyl) propanone manufactured by Lamberti) Chemcure-JETX ... CHEMBRIDGE INTERNATIONAL CORP. Photopolymerization initiator 2,4-diethylthioxanthone SB-PI704 ... Shuang-Bang Industrial Corp. Photopolymerization initiator 4-Methylquinone, dimethylaminobenzoate manufactured by Seiko Chemical Co., Ltd. Polymerization inhibitor p-methoxyphenol BYK-350, acrylic leveling agent CC7610 manufactured by BYK-CHMIE, polyethylene dispersion manufactured by Lubrizol body
  • the active energy ray-curable composition for flooring of Example or Comparative Example was applied to a hard PVC board (Mitsubishi Resin Co., Ltd .: Hishi Plate 303GE) with a film thickness of 6 ⁇ m by the aforementioned printing method, Next, irradiation is performed with an LED irradiation device (emission wavelength: 385 nm, peak intensity: 500 mW / cm 2) manufactured by Hamamatsu Photonics Co., Ltd. equipped with a stage moving device so that the amount of irradiation energy per irradiation is 50 mJ / cm 2. And the integrated value of the irradiation energy amount until it became tack-free was measured.
  • the sensitivity of the active energy ray-curable composition for flooring is preferably a sensitivity that cures with an integrated light amount of up to 500 mJ / cm 2 in order to correspond to practical curing conditions.
  • the active energy ray curable composition for flooring obtained in the examples can be sufficiently cured even when a movable curing device having a UV-LED light source is used.
  • the construction method which hardens the composition and the composition was able to be obtained.

Abstract

La présente invention concerne une composition durcissable par rayons actiniques pour des matériaux de plancher, ladite composition conservant une performance physique classique et qui, malgré ceci, présente une aptitude au durcissement suffisante lorsqu'elle est irradiée avec des rayons actiniques par une source de lumière UV-DEL ayant une longueur d'onde maximale comprise entre 350 et 420 nm de sorte à présenter des propriétés physiques durables. La composition durcissable par rayons actiniques pour des matériaux de plancher comprend un composé polymérisable par rayons actiniques (A) ayant une double liaison éthylénique, et un initiateur de photopolymérisation de l'oxyde acylphosphine (B).
PCT/JP2015/051641 2014-01-29 2015-01-22 Composition durcissable par rayons actiniques pour un matériau de plancher WO2015115293A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-014319 2014-01-29
JP2014014319 2014-01-29

Publications (1)

Publication Number Publication Date
WO2015115293A1 true WO2015115293A1 (fr) 2015-08-06

Family

ID=53756869

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/051641 WO2015115293A1 (fr) 2014-01-29 2015-01-22 Composition durcissable par rayons actiniques pour un matériau de plancher

Country Status (1)

Country Link
WO (1) WO2015115293A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003113668A (ja) * 2001-07-24 2003-04-18 Waado:Kk 床面の装飾方法および床面用装飾材
JP2008265236A (ja) * 2007-04-24 2008-11-06 Matsushita Electric Works Ltd 機能性材料
JP2010150464A (ja) * 2008-12-26 2010-07-08 Toyo Ink Mfg Co Ltd Ｕｖ−ｌｅｄ用活性エネルギー線硬化型スクリーンインキおよび印刷物
JP2011256331A (ja) * 2010-06-11 2011-12-22 Dic Corp 活性エネルギー線硬化型樹脂組成物、その硬化物の製造方法、及び成形品。
JP2012241116A (ja) * 2011-05-20 2012-12-10 Dnp Fine Chemicals Co Ltd 活性エネルギー線硬化型組成物、塗膜の形成方法、及び塗膜
JP2013057185A (ja) * 2011-09-07 2013-03-28 Sanyu Rec Co Ltd 滑り止め部材の形成シート、滑り止め部材の形成シートの製造方法、および、滑り止め部材の形成方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003113668A (ja) * 2001-07-24 2003-04-18 Waado:Kk 床面の装飾方法および床面用装飾材
JP2008265236A (ja) * 2007-04-24 2008-11-06 Matsushita Electric Works Ltd 機能性材料
JP2010150464A (ja) * 2008-12-26 2010-07-08 Toyo Ink Mfg Co Ltd Ｕｖ−ｌｅｄ用活性エネルギー線硬化型スクリーンインキおよび印刷物
JP2011256331A (ja) * 2010-06-11 2011-12-22 Dic Corp 活性エネルギー線硬化型樹脂組成物、その硬化物の製造方法、及び成形品。
JP2012241116A (ja) * 2011-05-20 2012-12-10 Dnp Fine Chemicals Co Ltd 活性エネルギー線硬化型組成物、塗膜の形成方法、及び塗膜
JP2013057185A (ja) * 2011-09-07 2013-03-28 Sanyu Rec Co Ltd 滑り止め部材の形成シート、滑り止め部材の形成シートの製造方法、および、滑り止め部材の形成方法

Similar Documents

Publication Publication Date Title
JP5846336B2 (ja) 床材用活性エネルギー線硬化性組成物
JP5800212B1 (ja) 床材用活性エネルギー線硬化性組成物とその施工方法
JP5910799B2 (ja) 床材用活性エネルギー線硬化性組成物の硬化方法、及びその硬化方法を用いた硬化装置
JP7101938B2 (ja) インクジェット用活性エネルギー線硬化型インク、インク収容容器、２次元又は３次元の像形成装置、硬化物の製造方法及び硬化物
TW201739850A (zh) 光硬化型噴墨印刷用墨水組成物及噴墨印刷方法
WO2012172973A1 (fr) Composition d'encre durcissable par rayonnement d'énergie active pour impression à jet d'encre et procédé de formation d'images
KR20130108634A (ko) 활성 에너지선 경화형 잉크젯 기록용 잉크 조성물 및 화상 형성 방법
JP5815913B1 (ja) 活性エネルギー線硬化型オフセットインキ組成物
JP2016079190A (ja) 硬化装置
WO2015163184A1 (fr) Procédé pour le durcissement d'une encre offset durcissable par un rayonnement d'énergie active
EP3303488B1 (fr) Encre d'impression
TW201903079A (zh) 胺基（甲基）丙烯酸酯
JP2017105877A (ja) 床材用活性エネルギー線硬化性組成物
JP5809780B2 (ja) 紫外線硬化性コーティングニス
JP2014181281A (ja) 活性エネルギー線硬化型インクジェット記録用インク組成物及びその製造方法
JP2014189753A (ja) 活性エネルギー線硬化型インクジェット記録用インク組成物の製造方法
JP2011001449A (ja) 紫外線発光ダイオード硬化性コーティングニス及び該コーティングニスを用いた印刷物
WO2015115293A1 (fr) Composition durcissable par rayons actiniques pour un matériau de plancher
JP6657973B2 (ja) 建材用インクジェットインク白色受理層用活性エネルギー線硬化性組成物
JP6861282B2 (ja) 活性エネルギー線硬化型インキ、インキ硬化物の製造方法及び印刷物
JP2023163470A (ja) 放射線硬化型インクジェット組成物
JP5769019B2 (ja) トリメリット酸トリアリル重合体、及びその重合体を含む光硬化性樹脂組成物とその用途
JP2023097117A (ja) 活性エネルギー線硬化性インク組成物及び印刷物の製造方法
JP2023131699A (ja) 組成物および印刷方法
JP2023146160A (ja) 活性エネルギー線硬化型オフセット印刷インキ、これを用いた印刷物、及び印刷物の製造方法

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: 15743051

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 15743051

Country of ref document: EP

Kind code of ref document: A1