WO2014156813A1 - Composition durcissable par rayon d'énergie active, film de revêtement durci de celle-ci et article ayant ledit film de revêtement durci - Google Patents

Composition durcissable par rayon d'énergie active, film de revêtement durci de celle-ci et article ayant ledit film de revêtement durci Download PDF

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Publication number
WO2014156813A1
WO2014156813A1 PCT/JP2014/057282 JP2014057282W WO2014156813A1 WO 2014156813 A1 WO2014156813 A1 WO 2014156813A1 JP 2014057282 W JP2014057282 W JP 2014057282W WO 2014156813 A1 WO2014156813 A1 WO 2014156813A1
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Prior art keywords
meth
acrylate
active energy
curable composition
energy ray
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PCT/JP2014/057282
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English (en)
Japanese (ja)
Inventor
卓 村川
隆志 安村
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Dic株式会社
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Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to CN201480019076.7A priority Critical patent/CN105073809B/zh
Priority to JP2014532748A priority patent/JP5686228B1/ja
Priority to KR1020157030792A priority patent/KR20150138281A/ko
Publication of WO2014156813A1 publication Critical patent/WO2014156813A1/fr

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Classifications

    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
    • C08F299/065—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes from polyurethanes with side or terminal unsaturations

Definitions

  • the present invention relates to an active energy ray-curable composition capable of imparting soft feel to the surface of various articles and capable of obtaining a coating film having high adhesion to a substrate, and an article using the same.
  • plastic molded products have been widely used in the body of home appliances such as refrigerators, televisions, air conditioners and the like, as well as remote controllers, mobile phones, smartphones, personal computer cases such as personal computers.
  • these plastic molded products may be used as they are, but are often painted to impart design properties.
  • an isocyanate compound obtained by reacting a polyester polyol having two or more hydroxyl groups in one molecule and hexamethylene diisocyanate is further reacted with a (meth) acrylate having a hydroxyl group.
  • An active energy ray-curable topcoat composition containing the obtained active energy ray-curable urethane (meth) acrylate and a photopolymerization initiator has been proposed (see, for example, Patent Document 1).
  • this active energy ray-curable topcoat composition has a problem that the tactile sensation such as high elasticity and low grip necessary for soft feel is insufficient.
  • the problem to be solved by the present invention is to provide an active energy ray-curable composition capable of imparting excellent tactile soft feel to the surface of various articles and obtaining a coating film having high adhesion to the substrate. It is to provide a product and an article using the product.
  • the inventors of the present invention contain an isocyanurate ring, a polyoxyalkylene chain having an average repeating unit number of 4 to 20 and a (meth) acrylate (A) having a caprolactone structure.
  • an active energy ray-curable composition characterized by the above it has been found that a soft feel can be imparted to the surface of various articles, and a coating film having high adhesion to a substrate can be obtained. Was completed.
  • the present invention includes an active energy ray-curable composition
  • an active energy ray-curable composition comprising an isocyanurate ring, a polyoxyalkylene chain having an average number of repeating units of 4 to 20 and a (meth) acrylate (A) having a caprolactone structure, and It relates to an article using the same.
  • the active energy ray-curable composition of the present invention can impart soft feel to the surface of various articles and can provide a coating film with high adhesion to the substrate. Therefore, soft feel can be imparted to the surface of a wide range of plastic molded products such as a main body of home appliances such as a refrigerator, a TV, an air conditioner, and a remote controller, a mobile phone, a smartphone, a personal computer, and other information terminals.
  • the active energy ray-curable composition of the present invention contains an isocyanurate ring, a polyoxyalkylene chain having an average repeating unit number of 4 to 20 and a (meth) acrylate (A) having a caprolactone structure.
  • (meth) acryloyl refers to one or both of acryloyl and methacryloyl groups
  • (meth) acrylate refers to one or both of acrylate and methacrylate
  • (meth) acrylic “Acid” refers to one or both of acrylic acid and methacrylic acid.
  • the (meth) acrylate (A) has in its structure an isocyanurate ring, a polyoxyalkylene chain having an average number of repeating units of 4 to 20 and a caprolactone structure.
  • Examples of the method for producing the (meth) acrylate (A) include the following methods (1) to (7).
  • the urethanization reaction and esterification reaction performed by the above methods (1) to (7) can be performed by known methods.
  • the urethanization reaction is preferably performed in the presence of a urethanization catalyst.
  • the urethanization catalyst include amine compounds such as triethylamine, dibutyltin dilaurate, dioctyltin dilaurate, octyltin trilaurate, dioctyltin dineodecanate, dibutyltin diacetate, dioctyltin diacetate, organotin compounds such as dioctyltin, And organometallic compounds such as zinc octylate (zinc 2-ethylhexanoate).
  • the polyisocyanate compound (a1) is not particularly limited as long as it has an isocyanurate ring on its structure, and examples thereof include diisocyanate trimers.
  • diisocyanate examples include hexamethylene diisocyanate, phenylene diisocyanate, toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, and isophorone diisocyanate.
  • Polyisocyanates obtained by reacting these diisocyanate trimers with polyols can also be used as the polyisocyanate compound (a1).
  • polystyrene resin examples include aliphatic diols such as 2,2,4-trimethyl-1,3-pentanediol, 1,3-hexanediol, and 1,6-hexanediol, and dimers of unsaturated aliphatic alcohols. Etc.
  • these polyisocyanate compounds (a1) can be used alone or in combination of two or more.
  • polyisocyanate compounds (a1) those containing a trimerized product of hexamethylene diisocyanate are preferable because a soft feel with better tactile sensation can be obtained.
  • the polyoxyalkylene mono (meth) acrylate (a2) is a compound having a polyoxyalkylene chain having an average number of repeating units of 4 to 20 and one (meth) acryloyl group.
  • the following general formula (1) The compound represented by these is mentioned.
  • R represents a hydrogen atom or a methyl group
  • A represents an alkylene group
  • n represents an average number of repetitions, and the range thereof is 4 to 20.
  • A is one or two.
  • the repeating units may be arranged in a random manner or in a block manner.
  • A is preferably an alkylene group having 1 to 6 carbon atoms, and A is a propylene group.
  • Polyoxypropylene mono (meth) acrylate and polyoxyethylene mono (meth) acrylate in which A is an ethylene group are more preferable.
  • the range of n representing the average number of repeating oxyalkylenes is preferably 5 to 14, more preferably 6 to 13.
  • these polyoxyalkylene mono (meth) acrylates (a2) can be used alone or in combination of two or more.
  • Examples of the caprolactone-modified alkyl (meth) acrylate (a3) include compounds represented by the following general formula (2).
  • R represents a hydrogen atom or a methyl group
  • m represents an integer of 1 to 6
  • n represents an average number of repeating units, and the range thereof is 1 to 10.
  • the (meth) acrylate (a3) is preferably a (meth) acrylate having an average number of repeating units of a caprolactone structure of 2 to 10 because adhesion and soft feel are improved.
  • Examples of the compound (a4) having an isocyanate group and a (meth) acryloyl group include 2- (meth) acryloyloxyethyl isocyanate and 1,1- (bis (meth) acryloyloxymethyl) ethyl isocyanate.
  • the number of equivalents (NCO) of isocyanate groups of the polyisocyanate compound (a1) and the polyoxyethylene mono (meth) Equivalent ratio (NCO / OH) of equivalent number (OHa2) of total number of equivalents of hydroxyl group (OHa2) possessed by acrylate (a2) and equivalent number of hydroxyl groups (OHa3) possessed by caprolactone-modified alkyl (meth) acrylate (a3) ) Is preferably in the range of 0.8 to 1.1, more preferably in the range of 0.9 to 1.05, and still more preferably in the range of 0.95 to 1.02.
  • the active energy ray-curable composition of the present invention is not limited as long as it contains the (meth) acrylate (A). Since the adhesion to the substrate is improved, the ester in the solid content of the composition
  • the group concentration is preferably in the range of 1.9 to 6.5 mmol / g, more preferably in the range of 2.2 to 6 mmol / g.
  • the photopolymerization initiator is not included in the solid content of the composition.
  • Examples of the active energy ray-curable monomer (B) include N- (2-hydroxyethyl) (meth) acrylamide, N-isopropyl (meth) acrylamide, (meth) acryloylmorpholine, dimethylaminopropyl (meth). Examples include acrylamide, dimethyl (meth) acrylamide, diethyl (meth) acrylamide, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Moreover, these active energy ray-curable monomers (B) can be used alone or in combination of two or more.
  • the active energy ray-curable composition of the present invention can be formed into a cured coating film by irradiating active energy rays after being applied to a substrate.
  • the active energy rays refer to ionizing radiation such as ultraviolet rays, electron beams, ⁇ rays, ⁇ rays, and ⁇ rays.
  • a photopolymerization initiator (C) to the active energy ray-curable composition of the present invention.
  • a photosensitizer can be further added to improve curability.
  • ionizing radiation such as electron beam, ⁇ -ray, ⁇ -ray, and ⁇ -ray
  • it cures quickly without using a photopolymerization initiator (C) or a photosensitizer. It is not necessary to add an initiator (C) or a photosensitizer.
  • Examples of the photopolymerization initiator (C) include intramolecular cleavage type photopolymerization initiators and hydrogen abstraction type photopolymerization initiators.
  • Examples of the intramolecular cleavage type photopolymerization initiator include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy.
  • examples of the hydrogen abstraction type photopolymerization initiator include benzophenone, methyl 4-phenylbenzophenone o-benzoylbenzoate, 4,4′-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4′-methyl-diphenyl sulfide.
  • Benzophenone compounds such as acrylated benzophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 3,3′-dimethyl-4-methoxybenzophenone; 2-isopropylthioxanthone, 2,4 -Thioxanthone compounds such as dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone; Aminobenzophenone compounds such as Michler-ketone, 4,4'-diethylaminobenzophenone; -2-chloro acridone, 2-ethyl anthraquinone, 9,10-phenanthrenequinone, camphorquinone, and the like.
  • These photopolymerization initiators (C) can be used alone or in combination of two or more.
  • the photosensitizer examples include amines such as aliphatic amines and aromatic amines, ureas such as o-tolylthiourea, sulfur such as sodium diethyldithiophosphate, s-benzylisothiuronium-p-toluenesulfonate, and the like. Compound etc. are mentioned.
  • photopolymerization initiators and photosensitizers are preferably used in an amount of 0.05 to 20 parts by mass with respect to 100 parts by mass of the non-volatile component in the active energy ray-curable aqueous coating material of the present invention, respectively. More preferred is 10% by mass.
  • silica particles (D) it is preferable to add silica particles (D) to the active energy ray-curable composition of the present invention in order to impart a good tactile sensation.
  • the silica particles (D) include dry silica and wet silica. Among these, dry silica is preferable because tactile sensation is further improved, and dry silica whose surface is modified with an organic compound is more preferable.
  • the average particle diameter of the silica particles is preferably in the range of 1 to 20 ⁇ m, more preferably in the range of 5 to 15 ⁇ m. The average particle diameter is measured with a laser diffraction / scattering particle size analyzer.
  • a silicone-based surface conditioner (E) examples include polysiloxane-modified acrylic resin and polyether-modified polydimethylsiloxane.
  • an organic solvent such as a stabilizer, a heat stabilizer, an ultraviolet absorber, an antioxidant, a leveling agent, an organic pigment, an inorganic pigment, and a pigment dispersant can be used.
  • the coating method of the active energy ray-curable composition of the present invention varies depending on the article to be coated, for example, gravure coater, roll coater, comma coater, knife coater, air knife coater, curtain coater, kiss coater, shower
  • the method include a coater, a wheeler coater, a spin coater, dipping, screen printing, spraying, an applicator, and a bar coater.
  • the active energy ray-curable composition of the present invention is preferably diluted with an organic solvent in order to adjust the viscosity to be suitable for the above coating method.
  • organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; methanol, ethanol, isopropanol, t-butanol, propylene glycol monomethyl ether, propylene glycol normal propyl ether, ethylene glycol monobutyl ether, diacetone alcohol, and the like.
  • Alcohol solvents such as ethyl acetate, butyl acetate, isobutyl acetate, normal propyl acetate, and propylene glycol monomethyl ether acetate; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone. These solvents can be used alone or in combination of two or more.
  • the active energy ray for curing the active energy ray-curable composition of the present invention is an ionizing radiation such as an ultraviolet ray, an electron beam, an ⁇ ray, a ⁇ ray, and a ⁇ ray.
  • an ionizing radiation such as an ultraviolet ray, an electron beam, an ⁇ ray, a ⁇ ray, and a ⁇ ray.
  • a curing device for example, a germicidal lamp, an ultraviolet fluorescent lamp, a carbon arc, a xenon lamp, a high pressure mercury lamp for copying, an intermediate or high pressure mercury lamp, an ultrahigh pressure mercury lamp, an electrodeless lamp, a metal halide lamp, natural light, etc.
  • the electron beam include ultraviolet rays, a scanning type, and a curtain type electron beam accelerator.
  • the active energy ray-curable composition of the present invention can impart soft feel to the surface of various articles.
  • the active energy ray-curable composition of the present invention may be applied directly to an article to be coated, or after applying a primer coating material suitable for the article to be coated, A wire curable composition may be applied.
  • primer coating material examples include various types such as a one-component type in which an acrylic resin or the like is diluted with an organic solvent, a two-component type in which a polyol is diluted with an organic solvent and a polyisocyanate is diluted with an organic solvent. Can be used.
  • PC polycarbonate
  • ABS acrylonitrile-butadiene-styrene copolymer
  • PMMA polymethyl methacrylate
  • Various resins such as polyethylene terephthalate (PET), polyamide (PA), polypropylene (PP); fiber reinforced plastics (FRP) in which fillers such as glass fibers are added to these resins; iron, copper, zinc, aluminum, magnesium, etc.
  • the article of the present invention has a cured coating film of the active energy ray-curable composition of the present invention.
  • the main body of home appliances such as a refrigerator, a TV, and an air conditioner and its remote controller, mobile phone, smartphone, personal computer
  • a casing of an information terminal such as a plastic molded product such as an automobile interior material.
  • Example 1 Preparation of active energy ray-curable composition (1)
  • a photopolymerization initiator BASF Japan Stock Co., Ltd.
  • 112.5 parts by mass ((90 parts by mass as polyfunctional acrylate (1)) of the polyfunctional acrylate (1) obtained in Synthesis Example 1 (non-volatile content: 80% by mass).
  • Examples 2 to 5 Preparation of active energy ray-curable compositions (2) to (5)
  • Active energy ray-curable compositions (2) to (5) were prepared in the same manner as in Example 1 except that the compositions shown in Table 1 were changed.
  • Table 1 shows the compositions of the active energy ray-curable compositions (1) to (5) and (R1) to (R2) obtained above.
  • Example 6 Evaluation of active energy ray-curable composition (1)
  • the active energy ray-curable composition (1) obtained above on the surface of an ABS resin plate (thickness 1 mm) is thinner (diacetone alcohol / methyl isobutyl ketone / ethyl acetate / After diluting with butyl acetate 30/30/20/20 (mass%), spray coating was performed. Then, after leaving at room temperature (25 ° C.) for 10 minutes, after preliminary drying at 60 ° C. for 10 minutes in a dryer, using a high-pressure mercury lamp with an output of 80 W / cm, an irradiation amount of 0.8 J / cm 2 Ultraviolet irradiation was performed to produce a cured coating film for evaluation.
  • Examples 7 to 10 Evaluation of active energy ray-curable compositions (2) to (5)
  • the active energy ray-curable compositions (2) to (5) obtained in Examples 2 to 5 were used. Except that each was used, it carried out similarly to Example 6, produced the cured coating film for evaluation, and evaluated the coating-film external appearance, adhesiveness, and soft feel property.
  • Table 2 shows the evaluation results of Examples 6 to 10 and Comparative Examples 3 to 4 described above.
  • Comparative Example 1 was an example having no polycaprolactone structure in (meth) acrylate (A), but it was found that the adhesion to the substrate was poor (Comparative Example 3).
  • Comparative Example 2 was an example having no polyoxyalkylene chain in (meth) acrylate (A), but it was found that the soft feel was insufficient (Comparative Example 4).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)

Abstract

L'invention concerne une composition durcissable par rayon d'énergie active caractérisée en ce qu'elle contient un (méth)acrylate (A) ayant une structure caprolactone, une chaîne polyoxyalkyle ayant un nombre moyen d'unités de répétition de 4-20 et un noyau isocyanurate. La composition durcissable par rayon d'énergie active peut conférer des propriétés de toucher doux de telle sorte que la douceur peut être ressentie lorsque l'on touche la surface de divers articles avec les doigts et peut former un film de revêtement ayant une adhérence supérieure à un substrat en matière plastique. Comme article, divers articles moulés en matière plastique peuvent être cités par exemple comprenant des corps principaux d'appareils électroménagers tels que des réfrigérateurs, des télévisions, des conditionneurs d'air et similaires, des boîtiers pour des terminaux d'informations tels que des ordinateurs personnels, des téléphones intelligents, des téléphones cellulaires, des télécommandes pour les appareils et similaires, des matières d'intérieur d'automobile et similaires.
PCT/JP2014/057282 2013-03-27 2014-03-18 Composition durcissable par rayon d'énergie active, film de revêtement durci de celle-ci et article ayant ledit film de revêtement durci WO2014156813A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201480019076.7A CN105073809B (zh) 2013-03-27 2014-03-18 活性能量射线固化性组合物、其固化涂膜、和具有该固化涂膜的物品
JP2014532748A JP5686228B1 (ja) 2013-03-27 2014-03-18 活性エネルギー線硬化性組成物、その硬化塗膜、及び該硬化塗膜を有する物品
KR1020157030792A KR20150138281A (ko) 2013-03-27 2014-03-18 활성 에너지선 경화성 조성물, 그 경화 도막, 및 당해 경화 도막을 갖는 물품

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JP2013-066363 2013-03-27
JP2013066363 2013-03-27

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WO2014156813A1 true WO2014156813A1 (fr) 2014-10-02

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JP (1) JP5686228B1 (fr)
KR (1) KR20150138281A (fr)
CN (1) CN105073809B (fr)
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KR20180133911A (ko) * 2016-04-19 2018-12-17 더 셔윈-윌리암즈 캄파니 2 성분 폴리우레탄 탑코트

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JP2017535625A (ja) * 2014-12-01 2017-11-30 エルジー・ケム・リミテッド 自己復元特性を有するコーティング層形成用組成物、コーティング層およびフィルム
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KR20180133911A (ko) * 2016-04-19 2018-12-17 더 셔윈-윌리암즈 캄파니 2 성분 폴리우레탄 탑코트
KR102196529B1 (ko) 2016-04-19 2020-12-30 더 셔윈-윌리암즈 캄파니 2 성분 폴리우레탄 탑코트

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