WO2011105069A1 - 活性エネルギー線硬化性樹脂組成物と硬化物 - Google Patents

活性エネルギー線硬化性樹脂組成物と硬化物 Download PDF

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Publication number
WO2011105069A1
WO2011105069A1 PCT/JP2011/001020 JP2011001020W WO2011105069A1 WO 2011105069 A1 WO2011105069 A1 WO 2011105069A1 JP 2011001020 W JP2011001020 W JP 2011001020W WO 2011105069 A1 WO2011105069 A1 WO 2011105069A1
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meth
resin composition
curable resin
acrylate
active energy
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PCT/JP2011/001020
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English (en)
French (fr)
Japanese (ja)
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昇平 槇田
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太陽ホールディングス株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04M—TELEPHONIC COMMUNICATION
    • H04M1/00—Substation equipment, e.g. for use by subscribers
    • H04M1/02—Constructional features of telephone sets
    • H04M1/23—Construction or mounting of dials or of equivalent devices; Means for facilitating the use thereof

Definitions

  • the present invention relates to an active energy ray-curable resin composition applied to applications requiring low warpage, adhesion at high temperature and high humidity, and wear resistance.
  • a photocurable resin mainly used for a button of a mobile phone or the like is required to have transparency, low curing shrinkage, and the like. Furthermore, recently, along with the enhancement of functions of such mobile phones, high reliability that does not cause problems even under high temperature and high humidity is required. Further, when used in an outermost case such as a case, in addition to these characteristics, wear resistance, impact resistance, and the like are required.
  • a photocurable resin having low curing shrinkage there is a photosensitive resin using a bifunctional urethane acrylate resin (see Patent Document 1 and Patent Document 2). There is also a method using a tri- or higher functional photosensitive resin in order to improve scratch resistance and hardness (see Patent Document 3).
  • Monofunctional or bifunctional photosensitive resins are used to achieve low cure shrinkage, but these are inferior in wear resistance and impact resistance.
  • tri- or higher functional photosensitive resins are good for improving wear resistance and impact resistance, but these have a problem of large shrinkage in curing and cause large warpage in the molded product of the cured product. is there.
  • the present invention provides a cured product having high adhesion to a base material even under high temperature and high humidity without causing warping, and further having abrasion resistance when cured by irradiation with active energy rays.
  • An object is to provide an active energy ray-curable resin composition and a cured product obtained by curing the active energy ray-curable resin composition.
  • the present inventors have found that there is no warpage, high adhesion to the substrate even when exposed to high temperature and high humidity, and activity that can provide a cured product having wear resistance.
  • an energy ray curable resin composition the inventors have conceived an invention having the following contents.
  • the active energy ray-curable resin composition of the present invention includes a urethane resin having a plurality of (meth) acrylate groups, a photosensitive amide and / or a derivative of a photosensitive amide, and a cyclic skeleton containing no double bond. It contains a functional (meth) acrylate and a photopolymerization initiator.
  • the photosensitive amide and / or the derivative of the photosensitive amide is at least one of N- (2-hydroxyethyl) acrylamide, N- (2-hydroxyethyl) methacrylamide, N-acryloylmorpholine, and N-methacryloylmorpholine. It is characterized by comprising.
  • cured material or molded article of this invention is obtained by hardening
  • the “durometer hardness D type” refers to a value measured according to JIS K7215.
  • (meth) acrylate is a term that collectively refers to acrylate and methacrylate, and the same applies to other similar expressions.
  • an acrylate and a methacrylate may be used independently or may be used in mixture of 2 or more types.
  • an active energy ray-curable resin composition capable of obtaining a hardened product and a cured product thereof are obtained.
  • a plate having a concave portion on its surface, which is used for producing the cured product of the present invention A state in which the concave portion of the plate is filled with the active energy ray resin composition of the present invention.
  • the urethane resin having a plurality of (meth) acrylate groups contained in the active energy ray-curable resin composition of the present invention preferably has a weight average molecular weight in the range of 1,000 to 20,000.
  • the weight average molecular weight is less than 1,000, the crosslink density caused by the urethane resin having a plurality of (meth) acrylate groups is increased, and the curing shrinkage of the resin is increased, so that the warpage of the cured molded product is also increased.
  • the weight average molecular weight is 20,000 If it exceeds 0, the viscosity becomes high, which is not preferable in the application of the present invention.
  • urethane resins having a plurality of (meth) acrylate groups a bifunctional urethane (meth) acrylate resin and a trifunctional urethane (meth) acrylate resin are preferable.
  • urethane resin having a plurality of (meth) acrylate groups, bifunctional U-108A, UA-112P, UA-5201, UA-512, UA-412A, UA-4200, UA manufactured by Shin-Nakamura Chemical Co., Ltd.
  • urethane resins having a plurality of (meth) acrylate groups may be used alone or in admixture of two or more.
  • Examples of the photosensitive amide and the photosensitive amide derivative contained in the active energy ray-curable resin composition of the present invention include N-vinylformamide, N-vinylacetamide, (meth) acrylamide, N-methyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, Nn-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-methyl-Nn-propyl (meth) Acrylamide, N-methyl-N-isopropyl (meth) acrylamide, N-tetrahydrofurfuryl (meth) acrylamide, N-ethoxypropyl (meth) acrylamide, N-ethoxyethyl (meth) acrylamide, N-1-methyl-2- Methoxyethyl (meth) acrylamide, N Morpholinopropyl (meth) acrylamide, N
  • it is a photosensitive amide compound having a (meth) acryloyl group, among which N- (2-hydroxyethyl) acrylamide, N- (2-hydroxyethyl) methacrylamide, N-acryloylmorpholine, N-methacryloylmorpholine, At least one of these is particularly preferred from the viewpoint of transparency.
  • Such a photosensitive amide and / or a derivative of the photosensitive amide is preferably 15 to 200 parts by mass, more preferably 20 to 100 parts by mass with respect to 100 parts by mass of the urethane resin having a plurality of (meth) acrylate groups. Included in the ratio. If the blending amount of the photosensitive amide and / or the derivative of the photosensitive amide is less than 15 parts by mass, the adhesion is insufficient, while if it exceeds 200 parts by mass, the cured product tends to become brittle.
  • the bifunctional (meth) acrylate having a cyclic skeleton having no double bond which is contained in the active energy ray-curable resin composition of the present invention, prevents warpage by having no double bond, thereby preventing the cyclic skeleton. By having, it is possible to enhance the wear resistance.
  • the weight average molecular weight is preferably in the range of 150 to 2,000. When the weight average molecular weight is less than 150, the crosslinking density caused by the urethane resin having a plurality of (meth) acrylate groups is increased, and the curing shrinkage of the resin is increased, so that the warpage of the cured molded product is also increased. When the weight average molecular weight exceeds 2,000, the viscosity becomes high, which may not be applicable in the application of the present invention.
  • bifunctional (meth) acrylate having a cyclic skeleton having no double bond examples include cyclohexanedimethanol di (meth) acrylate, tricyclodencan dimethanol di (meth) acrylate, and hydrogenated bisphenol A di (meth).
  • Bifunctional (meth) having an alicyclic skeleton such as acrylate, hydrogenated bisphenol F di (meth) acrylate, hydrogenated hexafluorobisphenol A di (meth) acrylate, bis (2- (meth) acryloyloxy) hexahydrophthalic acid Heterocycles such as acrylate, 5-ethyl-2- (2-hydroxy-1,1dimethylethyl) -5- (hydroxymethyl) -1,3-dioxane diacrylate, 1,4-di (meth) acryloylpiperazine Bifunctional (meth) acrylate with skeleton, and even this Difunctional (meth) acrylates of ethylene oxide, propylene oxide, and a modified product such as caprolactone.
  • the bifunctional (meth) acrylate having a cyclic skeleton having no double bond is preferably 10 to 100 parts by mass, more preferably 100 parts by mass with respect to 100 parts by mass of the urethane resin having a plurality of (meth) acrylate groups. Is contained in a proportion of 20 to 50 parts by mass.
  • the blending amount of the bifunctional (meth) acrylate having a cyclic skeleton having no double bond is less than 10 parts by mass, the abrasion resistance is insufficient, and when it exceeds 100 parts by mass, the cured product becomes brittle. It tends to be unfavorable.
  • Examples of the photopolymerization initiator contained in the active energy ray-curable resin composition of the present invention include benzoin, benzyl, benzoin methyl ether, benzoin ethyl ether, benzoin n-propyl ether, benzoin isopropyl ether, and benzoin n-butyl ether.
  • Benzoins such as benzoin; benzoin alkyl ethers; benzophenones such as benzophenone, p-methylbenzophenone, Michler's ketone, methylbenzophenone, 4,4′-dichlorobenzophenone, 4,4′-bisdiethylaminobenzophenone; acetophenone, 2,2-dimethoxy -2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexyl phenylketo Acetophenones such as 2-methyl- [4- (methylthio) phenyl] -2-morpholino-1-propanone and N, N-dimethylaminoacetophenone; 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2- Thioxanthones such as chlorothioxanthone and 2,4-diisopropyl
  • photopolymerization initiators can be used alone or in combination of two or more.
  • This photopolymerization initiator is contained in a proportion of preferably 0.1 to 10 parts by mass, more preferably 0.3 to 5 parts by mass with respect to 100 parts by mass of the urethane resin having a plurality of (meth) acrylate groups. .
  • the active energy ray-curable resin composition of the present invention can be blended with an inorganic filler as necessary for the purpose of further improving properties such as adhesion, mechanical strength, and linear expansion coefficient of the cured product.
  • an inorganic filler such as barium sulfate, barium titanate, silicon oxide powder, finely divided silicon oxide, amorphous silica, talc, clay, magnesium carbonate, calcium carbonate, aluminum oxide, aluminum hydroxide, mica powder, etc.
  • Inorganic fillers can be used.
  • the blending ratio is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the present active energy ray-curable resin composition.
  • Colorants known and conventional photopolymerization inhibitors such as hydroquinone, hydroquinone monomethyl ether, t-butylcatechol, pyrogallol and phenothiazine, known and conventional thickeners such as finely divided silica, organic bentonite and montmorillonite, silicone-based, fluorine-based, high Known and commonly used additives such as defoamers and / or leveling agents such as molecular systems, silane coupling agents such as imidazole systems, thiazole systems, and triazole systems can be blended.
  • photopolymerization inhibitors such as hydroquinone, hydroquinone monomethyl ether, t-butylcatechol, pyrogallol and phenothiazine
  • known and conventional thickeners such as finely divided silica, organic bentonite and montmorillonite, silicone-based, fluorine-based, high Known and commonly used additives such as defoamers and / or leveling
  • the active energy ray-curable resin composition of the present invention preferably has a viscosity of 1 to 50 dPa ⁇ s.
  • This viscosity is preferably adjusted in the range of 1 to 100 parts by mass, more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the urethane resin having a plurality of (meth) acrylate groups. Can be provided. If the amount of reactive diluent is 1 part by mass or less, the viscosity is high and workability is lowered. On the other hand, if it is 100 parts by mass or more, the crosslink density of the cured product is reduced and sufficient wear resistance cannot be obtained.
  • hydroxyalkyl acrylates such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 4-hydroxybutyl acrylate
  • cyclic skeletons such as isobornyl acrylate, tetrahydrofurfuryl acrylate, N-acryloylmorpholine, and N-vinylpyrrolidinone.
  • Monofunctional photosensitive monomers having; mono- or diacrylates of glycols such as ethylene glycol, methoxytetraethylene glycol, polyethylene glycol, propylene glycol; N, N-dimethylacrylamide, N-methylolacrylamide, N, N-dimethylaminopropyl Acrylamides such as acrylamide; N, N-dimethylaminoethyl acrylate, N, N-dimethylaminopropyl acrylate A polyhydric alcohol such as hexanediol, trimethylolpropane, pentaerythritol, dipentaerythritol, tris-hydroxyethyl isocyanurate, or a polyhydric acrylate such as an ethylene oxide adduct or a propylene oxide adduct; Phenoxyacrylate, bisphenol A diacrylate, and acrylates such as ethylene oxide adducts or propylene oxide adducts of these phenols;
  • the active energy ray-curable resin composition according to the present invention is cured by irradiating active energy rays after being applied to a substrate or the like by the following application method.
  • the cured product or molded product preferably has a durometer hardness D type of 75 ° or more from the viewpoint of warpage prevention.
  • any method such as a dip coating method, a flow coating method, a roll coating method, a bar coater method, a screen printing method, a curtain coating method, a gravure printing method, and an offset printing method can be applied.
  • a low pressure mercury lamp As the irradiation source of the active energy ray, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp or a metal halide lamp is suitable.
  • laser beams, electron beams, and the like can be used as active energy rays.
  • a method for obtaining a molded product by filling the active energy ray-curable resin composition of the present invention using an intaglio, curing the filled resin composition with active energy rays, and taking out the cured product from the recess Illustrate.
  • FIG. 1 shows a plate having a desired shape formed on the surface.
  • a metal such as stainless steel is used.
  • FIG. 2 shows a state in which this plate is filled with the active energy ray-curable resin composition of the present invention.
  • the active energy ray-curable resin composition is filled into the concave portion of the plate using a doctor knife or the like.
  • FIG. 3 shows a state in which the active energy ray-curable resin composition of the present invention is cured by covering the base material from above and further irradiating ultraviolet light from the light source on the top.
  • a transparent polyethylene terephthalate or polycarbonate film that transmits ultraviolet rays is used as the substrate.
  • FIG. 4 shows a state in which the cured product is released from the plate to obtain a molded product.
  • a molded product can be continuously produced by using a dedicated apparatus.
  • EBECRYL 8807 Aliphatic bifunctional urethane acrylate (manufactured by Daicel-Cytec)
  • CN929 aliphatic trifunctional urethane acrylate (manufactured by Sartomer)
  • KAYARAD RM-1001 N-acryloylmorpholine (manufactured by Nippon Kayaku Co., Ltd.)
  • HEAA N- (2-hydroxyethyl) acrylamide (manufactured by Kojin Co., Ltd.)
  • Beam set 770 N-vinylformamide (Arakawa Chemical Industries)
  • Aronix M-111 1 mol of ethylene oxide addition nonylphenol acrylate (manufactured by Toagosei Co., Ltd.)
  • Light acrylate IB-XA Isoboronyl acrylate (manufactured by Kyoeisha Chemical Co., Ltd.) 4HBA: 4-hydroxybutyl
  • the active energy ray-curable resin composition thus prepared was evaluated for warpage, adhesion, and RCA wear by the following evaluation methods. The results are shown in Tables 3 and 4.
  • the resin composition is poured into a Teflon (registered trademark) mold having a length of 2 cm, a width of 2 cm, and a depth of 1 mm, covered with an easily adhesive-treated PET film, and a UV conveyor furnace (metal halide lamp, 80 W, 3 lights) is used.
  • the film was exposed at an integrated light quantity of 1000 mJ / cm 2 and released from the mold to obtain a cured coating film.
  • Warp test Place the cured coating film produced by the above method on a flat base so that the warped side faces upward, press one side with the warp against the base with your finger, and lift it from the base on the opposite side. The height was read and the warpage was measured.
  • ⁇ Warpage of cured coating film is less than 5 mm
  • Curing of cured coating film is 5 mm or more and less than 10 mm
  • Curing of cured coating film is 10 mm or more
  • RCA wear test The cured coating film produced by the above method was manufactured by NORMAN TOOL, INC. Using the RCA abrasion tester manufactured by the manufacturer and a dedicated abrasion paper for the RCA abrasion tester, it was worn 50 times under a load of 175 g, and the degree of wear of the cured coating film surface was observed with an optical microscope. ⁇ : Almost no wear ⁇ : Some wear ⁇ : Clear wear
  • the resin composition is poured into a stainless steel mold having a diameter of 2.5 cm and a depth of 3 mm, covered with a glass plate, and exposed using a UV conveyor furnace (high pressure mercury lamp, 80 W, 3 lights) at an exposure amount of 1000 mJ / cm 2 .
  • the mold was released to obtain a cured coating film.
  • the cured coating film produced by the above method was measured according to JIS K7215. The hardness value was read 30 seconds after the load surface was in close contact. At this time, the case of 75 ° or more was regarded as high hardness.
  • Examples 1 to 5 are excellent in warpage, adhesion, and wear resistance. Further, since the durometer hardness D type is 75 ° or more, the durometer hardness D type has high hardness and can suppress warpage. Since Comparative Examples 1 to 3 in Table 4 contain a photosensitive amide and / or a derivative of a photosensitive amide, the adhesion is good. However, although the durometer hardness D type is 70 ° or more, the hardness is insufficient and there is a problem with warpage. Moreover, since it does not contain a bifunctional (meth) acrylate having a cyclic skeleton that does not contain a double bond, the wear resistance is poor.
  • Comparative Examples 4 and 5 did not contain a photosensitive amide and / or a derivative of the photosensitive amide and a bifunctional (meth) acrylate having a cyclic skeleton containing no double bond, all the characteristics were inferior. Furthermore, since the durometer hardness D type is less than 75 °, the hardness is insufficient and there is a problem of warpage. Comparative Examples 6 and 7 do not contain a photosensitive amide and / or a derivative of the photosensitive amide, but have high adhesion because they contain a photosensitive monomer having a hydroxyl group that is a polar group. However, since the durometer hardness D type is less than 75 °, the hardness is insufficient, and there is a problem with warpage.

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  • Chemical Kinetics & Catalysis (AREA)
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PCT/JP2011/001020 2010-02-24 2011-02-23 活性エネルギー線硬化性樹脂組成物と硬化物 WO2011105069A1 (ja)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015151495A (ja) * 2014-02-17 2015-08-24 太陽インキ製造株式会社 光硬化性組成物および成形品
JP2020122053A (ja) * 2019-01-29 2020-08-13 株式会社日本触媒 活性エネルギー線硬化性樹脂組成物及びその硬化物

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6115100B2 (ja) 2012-11-23 2017-04-19 デクセリアルズ株式会社 光硬化性組成物
JP6455115B2 (ja) * 2014-12-10 2019-01-23 凸版印刷株式会社 光硬化性樹脂成形体、偏光板、および透過型液晶ディスプレイ
JP6826417B2 (ja) * 2015-11-20 2021-02-03 三洋化成工業株式会社 活性エネルギー線硬化型樹脂組成物

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JPH08183822A (ja) * 1994-12-28 1996-07-16 Takemoto Oil & Fat Co Ltd 光学的立体造形用樹脂
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JP3705508B2 (ja) * 1995-10-31 2005-10-12 ナブテスコ株式会社 耐熱性に優れる光硬化性樹脂組成物
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JPH08183822A (ja) * 1994-12-28 1996-07-16 Takemoto Oil & Fat Co Ltd 光学的立体造形用樹脂
JPH08183823A (ja) * 1994-12-28 1996-07-16 Takemoto Oil & Fat Co Ltd 光学的立体造形用樹脂及び光学的立体造形用樹脂組成物
JPH08183821A (ja) * 1994-12-28 1996-07-16 Takemoto Oil & Fat Co Ltd 光学的立体造形用樹脂及び光学的立体造形用樹脂組成物
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015151495A (ja) * 2014-02-17 2015-08-24 太陽インキ製造株式会社 光硬化性組成物および成形品
JP2020122053A (ja) * 2019-01-29 2020-08-13 株式会社日本触媒 活性エネルギー線硬化性樹脂組成物及びその硬化物
JP7240884B2 (ja) 2019-01-29 2023-03-16 株式会社日本触媒 活性エネルギー線硬化性樹脂組成物及びその硬化物

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