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WO2006046864A1 - Composition de resine photodurcissable et adhesif pour disque optique - Google Patents

Composition de resine photodurcissable et adhesif pour disque optique Download PDF

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Publication number
WO2006046864A1
WO2006046864A1 PCT/NL2005/000766 NL2005000766W WO2006046864A1 WO 2006046864 A1 WO2006046864 A1 WO 2006046864A1 NL 2005000766 W NL2005000766 W NL 2005000766W WO 2006046864 A1 WO2006046864 A1 WO 2006046864A1
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WIPO (PCT)
Prior art keywords
meth
acrylate
resin composition
curable resin
adhesive
Prior art date
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Ceased
Application number
PCT/NL2005/000766
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English (en)
Inventor
Satoshi Futami
Takayoshi Tanabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JSR Corp
Japan Fine Coatings Co Ltd
DSM IP Assets BV
Original Assignee
JSR Corp
Japan Fine Coatings Co Ltd
DSM IP Assets BV
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Publication of WO2006046864A1 publication Critical patent/WO2006046864A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Definitions

  • the present invention relates to a UV-curable resin composition suitable as an adhesive for a polymer material or the like. More particularly, the present invention relates to an adhesive curable liquid composition used in the field of optical disks (e.g. DVD), building materials, packaging materials, printing materials, display materials, electric/electronic materials, optical materials, liquid crystal panels, and the like.
  • optical disks e.g. DVD
  • building materials e.g., packaging materials, printing materials, display materials, electric/electronic materials, optical materials, liquid crystal panels, and the like.
  • Various display devices have been proposed accompanying development of information communication equipment.
  • a display device using a CRT a display device using a liquid crystal panel, a display device which projects an image onto a screen, a display device using a PDP panel, and the like can be given.
  • the display performance of such display devices is obtained by attaching members having various optical properties, such as a polymer film and a polymer lens.
  • a method of optically treating the surface of a lens using a polymer film has been proposed. This method requires that the polymer film be bonded to the lens substrate.
  • Polymer materials may be bonded by using various adhesives.
  • PVC polyvinyl chloride
  • PET polyethylene terephthalate
  • a solvent-free adhesive which can cause polymer materials to adhere upon application of radiation has been expected to become a material which can satisfy such a demand.
  • An adhesive used to cause materials having optical properties to adhere must not change in hue due to heating, UV exposure, or the like. However, a material which satisfies this demand has not yet been obtained.
  • a photocurable resin composition containing (1 ) a urethane (meth)acrylate, (2) a silane compound having a mercapto group, (3) a photoinitiator, (4) an ethylenically unsaturated monomer having an amino group, and (5) a (meth)acrylate compound has been reported to be useful as a coating layer for a copper-coated wire used as a tension member for an optical fiber unit (see Japanese Patent Application Laid-open No. 2000-198824).
  • Japanese Patent Application Laid-open No. 2002-264276 describes that yellowing caused by a fluorescent lamp is reduced by using a specific phenolic compound in a multilayer coating. However, the patent document 3 does not describe use of this compound for an adhesive.
  • the hot-melt adhesive has insufficient thermal stability and weatherability and softens at a high temperature, disks bonded using the hot-melt adhesive may be separated or deformed due to a decrease in bond strength.
  • the hot-melt adhesive has low transparency, it is difficult to use the hot-melt adhesive for a two-layered DVD having a translucent film as a recording film.
  • the heat-curable adhesive also has a problem such as causing deformation of a substrate forming a disk due to heat applied when curing the heat-curable adhesive or requiring a long time for curing.
  • the anaerobic curable adhesive also has a problem in which a long time is required for curing so that productivity is decreased.
  • a photocurable adhesive has been proposed in order to solve these problems.
  • Japanese Patent Application Laid-open No. 61-142545, Japanese Patent Application Laid-open No. 6-89462 and Japanese Patent Application Laid-open No. 2004-139706 disclose UV-curable resin adhesives containing a urethane acrylate as the major component.
  • compositions disclosed in the patent documents 1 and 2 have problems such as insufficient bond strength.
  • An LED light source having a sharp emission spectrum at 365 nm has long life in comparison with a mercury lamp or a metal halide lamp, and significantly reduces variation in irradiation intensity. Therefore, the LED light source is useful for manufacturing a DVD utilizing a photocurable adhesive.
  • photocurable resins disclosed in the patent documents 4 and 5 suffer from insufficient curability when using the LED light source.
  • a photocurable resin which can prevent corrosion of a metal-deposited film (DVD recording layer) caused by moisture has not yet been obtained.
  • An objective of the present invention is to provide a UV-curable resin composition exhibiting excellent photocurability and adhesion and showing only a small degree of yellowing.
  • the inventors of the present invention have conducted extensive studies in order to achieve the above objective. As a result, the inventors have found that, while a known photocurable resin has an absorbance at 365 nm of 5% to exhibit inferior curability, the curability of a photocurable resin is improved by increasing the absorbance to 20% or more by adding a polymerization initiator having a high absorbance at 365 nm. This finding has led to the completion of the present invention.
  • UV-curable resin composition is obtained:
  • a UV-curable resin composition comprising:
  • the photoinitiator (C) a photoinitiator of which the 0.1 wt% solution has an absorbance (optical length: 1 cm) at 365 nm of 0.2 or more, the amount of the photoinitiator being 0.1 to 15 wt% of the composition.
  • the photoinitiator (C) preferably includes at least one compound selected from the group consisting of 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-methyl-1-[4- methylthiophenyl]-2-morpholinopropan-1-one, and 2-benzyl-2- dimethylamino-1 -(4-morphorinophenyl)-butanone-1.
  • the invention also relates to a DVD adhesive comprising the above
  • UV-curable resin composition The UV-curable resin composition.
  • the photocurability of the resin composition is improved when using the LED light source, so that a DVD adhesive exhibiting excellent curability and useful for DVD lamination (attachment) operation using the LED light source can be obtained.
  • a UV-curable resin composition which has a viscosity suitable for application without using a solvent, exhibits sufficient adhesion to a polymer material, and shows only a small change in color due to heating or exposure to UV light, can be obtained.
  • UV-curable resin composition (1) Urethane (meth)acrylate (A)
  • the urethane (meth)acrylate (A) used in the present invention is produced by reacting (a) a diisocyanate, (b) a hydroxyl group-containing (meth)acrylate, and (c) a diol. Specifically, the urethane (meth)acrylate (A) is produced by reacting isocyanate groups of the diisocyanate with hydroxyl groups of the diol and the hydroxyl group-containing (meth)acrylate.
  • reaction method a method of reacting the diol, the diisocyanate, and the hydroxyl group-containing (meth)acrylate all together; a method of reacting the diol with the diisocyanate, and reacting the resulting product with the hydroxyl group-containing (meth)acrylate; a method of reacting the diisocyanate with the hydroxyl group-containing (meth)acrylate, and reacting the resulting product with the diol; a method of reacting the diisocyanate with the hydroxyl group-containing (meth)acrylate, reacting the resulting product with the diol, and reacting the resulting product with the hydroxyl group-containing (meth)acrylate; and the like can be given.
  • the diol and the diisocyanate are reacted so that the number of diol repeating units in one molecule is included as preferably two or more, and still more preferably three or more. Specifically, the molar ratio of the diol to the diisocyanate is adjusted so that the number of moles of the diisocyanate is 1.5 or less for one mole of the diol.
  • the hydroxyl group-containing (meth)acrylate is preferably used so that the hydroxyl group-containing (meth)acrylate is 1.0 to 1.5 equivalents for the remaining isocyanate equivalent calculated from the molar ratio of the diol to the diisocyanate.
  • a urethanization catalyst such as copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyltin laurate, di-n-butyltin acetate, di-n-butyltin maleate, di-n- octyltin laurate, di-n-octyltin acetate, di-n-octyltin maleate, di-n-butyltin dilaurate, triethylamine, 1 ,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-1 ,4- diazabicyclo[2.2.2]octane, di-n-octyltin neodecanoate, or quartenary zirconium salt such as zirconium tetraacetylacetnate, in an amount from 0.01 to 1 part by
  • the reaction temperature is usually 10 to 9O 0 C, and preferably 30 to 8O 0 C.
  • diisocyanate used as the component (a)
  • aliphatic compounds such as 2,4-tolylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, and methylenebis(4-cyclohexylisocyanate) are preferable.
  • the aliphatic compound used as the diisocyanate component can reduce yellowing due to heating. The degree of yellowing due to heating can be further reduced by using isophorone diisocyanate or methylenebis(4-cyclohexylisocyanate).
  • the diisocyanate may be used either individually or in combination of two or more.
  • hydroxyl group-containing (meth)acrylate used as the component (b), 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2- hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenyloxypropyl (meth)acrylate, 1 ,4- butanediol mono(meth)acrylate, 2-hydroxyalkyl(meth)acryloyl phosphate, 4- hydroxybutyl (meth)acrylate, 4-hydroxycyclohexyl (meth)acrylate, 1 ,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolethane di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, compounds obtained by the addition reaction of (
  • the hydroxyl group-containing (meth)acrylate may be used either individually or in combination of two or more.
  • the diol (c) is at least one diol selected from the group consisting of polypropylene glycol, polybutylene glycol, a copolymer of 1 ,2- butylene oxide and ethylene oxide, and a copolymer of propylene oxide and ethylene oxide.
  • a polyol other than the above diol or a mixture of polyols may be used in addition to the component (c).
  • the number average molecular weight of the diol (c) is preferably 300 to 15,000, still more preferably 1,000 to 12,000, and particularly preferably 2,000 to 12,000.
  • Commercially available products which may be used as the component (c) are given below.
  • Polypropylene glycol is commercially available as PPG400, PPG1000, PPG2000, PPG3000, Excenol 720, 1020, 2020, Preminol PMLS- X4001 , PMLS-4003, PMLS-X4004, PMLS-X4008, PMLS-X4011 , PMLS-X4016, NPML- 4002A (manufactured by Asahi Glass Urethane Co., Ltd.), and the like.
  • a copolymer diol of 1 ,2-butylene oxide and ethylene oxide is commercially available as EO/BO500, EO/BO1000, EO/BO2000, EO/BO3000, EO/BO4000 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and the like.
  • the diol (c) may be used either individually or in combination of two or more.
  • a polyol other than the diol (c) or a mixture of polyols an aliphatic or cyclic polyether diol, polyester diol, polycarbonate diol, polycaprolactone diol, and the like can be given.
  • the polyol may be a random polymer, a block polymer, or a graft polymer.
  • polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, polyether diols obtained by the ring-opening copolymerization of two or more ion- polymerizable cyclic compounds, and the like can be given.
  • cyclic ethers such as ethylene oxide, propylene oxide, 1 ,2-butylene oxide, butene-1 -oxide, isobutene oxide, 3,3-bischloromethyloxetane, tetrahydrofuran, 2-methyltetrahydrofuran, 3-methyltetrahydrofuran, dioxane, trioxane, tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl methacrylate, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monoxide, isoprene monoxide, vinyloxetane, vinyltetrahydrofuran, vinylcyclohexene oxide, phenyl glycidyl ether, butyl glycidyl ether, and glycid
  • a polyether diol obtained by the ring-opening copolymerization of the ion-polymerizable cyclic compound with a cyclic imine such as ethyleneimine, a cyclic lactonic acid such as ⁇ -propyolactone or lactide glycolate, or a dimethylcyclopolysiloxane may also be used.
  • tetrahydrofuran and propylene oxide examples of specific combinations of the ion-polymerizable cyclic compounds, tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyltetrahydrofuran, tetrahydrofuran and 3- methyltetrahydrofuran, tetrahydrofuran and ethylene oxide, propylene oxide and ethylene oxide, butene-1 -oxide and ethylene oxide, a ternary copolymer of tetrahydrofuran, butene-1 -oxide, and ethylene oxide, and the like can be given.
  • the ring-opening copolymer of the ion-polymerizable cyclic compounds may be a random copolymer or a block copolymer.
  • polyether diols are commercially available as PTMG650, PTMG1000, PTMG2000 (manufactured by Mitsubishi Chemical Corp.), PEG1000, Unisafe DC1100, DC1800 (manufactured by Nippon Oil and Fats Co., Ltd.), PPTG2000, PPTG1000, PTG400, PTGL2000 (manufactured by Hodogaya Chemical Co., Ltd.), Z-3001-4, Z-3001-5, PBG2000A, PBG2000B (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and the like.
  • alkylene oxide addition diol of bisphenol A alkylene oxide addition diol of bisphenol F, hydrogenated bisphenol A, hydrogenated bisphenol F, alkylene oxide addition diol of hydrogenated bisphenol A, alkylene oxide addition diol of hydrogenated bisphenol F, alkylene oxide addition diol of hydroquinone, alkylene oxide addition diol of naphthohydroquinone, alkylene oxide addition diol of anthrahydroquinone, 1 ,4-cyclohexanediol and alkylene oxide addition diol thereof, tricyclodecanediol, tricyclodecanedimethanol, pentacyclopentadecanediol, pentacyclopentadecanedimethanol, and the like can be given.
  • alkylene oxide addition diol of bisphenol A alkylene oxide addition diol of hydrogenated bisphenol A, and tricyclodecanedimethanol are preferable.
  • These polyols are commercially available as Uniol DA400, DA700, DA1000, DB400 (manufactured by Nippon Oil and Fats Co., Ltd.), N1162 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), tricyclodecanedimethanol (manufactured by Mitsubishi Chemical Corp.), and the like.
  • polyester diol polyester diols obtained by reacting a diol with a dibasic acid and the like can be given.
  • polyester diols are commercially available as Kurapol P-2010, PMIPA, PKA-A, PKA-A2, PNA-2000 (manufactured by Kuraray Co., Ltd.), and the like.
  • polycarbonate diol polycarbonate of polytetrahydrofuran and polycarbonate of 1 ,6-hexanediol can be given.
  • commercially available products of the polycarbonate diol DN-980, 981 , 982, 983
  • PC-8000 manufactured by PPG
  • PC-THF-CD manufactured by BASF
  • polycaprolactone diols obtained by reacting epsilon-caprolactone and a diol such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1 ,2-polybutylene glycol, 1 ,6-hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, or 1 ,4-butanediol can be given.
  • diols are commercially available as Placcel 205, 205AL, 212, 212AL, 220, 220AL (manufactured by Daicel Chemical Industries, Ltd.), and the like.
  • diols other than those mentioned above may also be used.
  • diols ethylene glycol, 1 ,4-butanediol, 1 ,5-pentanediol, 1 ,6- hexanediol, neopentyl glycol, 1 ,4-cyclohexanedimethanol, dimethylol compound of dicyclopentadiene, tricyclodecanedimethanol, ⁇ -methyl- ⁇ -valerolactone, hydroxy- terminated polybutadiene, hydroxy-terminated hydrogenated polybutadiene, castor oil- modified polyol, diol-terminated compound of polydimethylsiloxane, polydimethylsiloxanecarbitol-modified diol, and the like can be given.
  • a diamine may be used in combination with the above diol.
  • the diamine ethylenediamine, tetramethylenediamine, hexamethylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, diamines containing a hetero atom, polyether diamines, and the like can be given.
  • polyether diol alkylene oxide addition diol of bisphenol A, and alkylene oxide addition diol of hydrogenated bisphenol A are preferable.
  • diols are commercially available as PTMG650, PTMG1000, PTMG2000 (manufactured by Mitsubishi Chemical Corp.), Uniol DA400, DA700, DA1000, DB400 (manufactured by Nippon Oil and Fats Co., Ltd.), and N1162 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
  • the number average molecular weight of such a diol component is 300 to 5,000, preferably 300 to 2,000, and still more preferably 300 to 1 ,000.
  • the urethane (meth)acrylate used as the component (A) is contained in an amount of preferably 1 to 95 wt%, and still more preferably 30 to 60 wt% for the total amount of the UV-curable resin composition in the present invention. If the amount is less than 1 wt% or exceeds 95 wt%, applicability may be impaired.
  • a cured product (adhesive) having high adhesion can be obtained by using the component (A).
  • the UV-curable resin composition of the present invention may contain a urethane (meth)acrylate obtained by reacting one mol of diisocyanate with two mol of hydroxyl group-containing (meth)acrylate.
  • a urethane (meth)acrylate obtained by reacting one mol of diisocyanate with two mol of hydroxyl group-containing (meth)acrylate.
  • a reaction product of hydroxyethyl (meth)acrylate and 2,4-tolylene diisocyanate a reaction product of hydroxyethyl (meth)acrylate and 2,5(2,6)- bis(isocyanatemethyl)-bicyclo[2.2.1]heptane
  • a reaction product of hydroxyethyl (meth)acrylate and isophorone diisocyanate a reaction product of hydroxypropyl (meth)acrylate and 2,4-tolylene diisocyanate
  • the radically polymerizable compounds (B) are used in the UV- curable resin composition of the present invention.
  • the monofunctional compound used as the radically polymerizable compound (B) N-vinylpyrrolidone, lactams containing a vinyl group such as N-vinylcaprolactam, (meth)acrylates containing an alicyclic structure such as isobomyl (meth)acrylate, bornyl (meth)acrylate, tricyclodecanyl (meth)acrylate, and dicyclopentanyl (meth)acrylate, benzyl (meth)acrylate, 4-butylcyclohexyl (meth)acrylate, acryloylmorpholine, vinylimidazole, vinylpyridine, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (
  • R 2 represents a hydrogen atom or a methyl group
  • R 3 represents an alkylene group having 2 to 6, and preferably 2 to 4 carbon atoms
  • R 4 represents a hydrogen atom or an alkyl group having 1 to 12, and preferably 1 to 9 carbon atoms
  • I represents an integer of 0 to 12, and preferably of 1 to 8.
  • R 5 represents a hydrogen atom or a methyl group
  • R 6 represents an alkylene group having 2 to 8, and preferably 2 to 5 carbon atoms
  • R 7 represents a hydrogen atom or a methyl group
  • p represents an integer of 1 to 4.
  • vinyl group-containing lactams such as N-vinylpyrrolidone and N-vinylcaprolactam, isobomyl (meth)acrylate, lauryl acrylate, acryloylmorpholine, and the compound of the formula (3) are preferable.
  • lactams such as N-vinylpyrrolidone and N-vinylcaprolactam
  • isobomyl (meth)acrylate isobomyl (meth)acrylate
  • lauryl acrylate acryloylmorpholine
  • compound of the formula (3) are preferable.
  • These monofunctional compounds are commercially available as
  • IBXA manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • Aronix M-111 manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • M-113 manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • M-114 manufactured by Osaka Organic Chemical Industry Co., Ltd.
  • M-117 manufactured by TO-1210
  • Aronix M-110 manufactured by Toagosei Co., Ltd.
  • TO-1210 manufactured by Toagosei Co., Ltd.
  • a cured product of the UV-curable resin composition prepared as described above exhibits such a bond strength for a polymer material as a peel strength of 10 N/m or more obtained for a PET film, for example.
  • a polymerizable polyfunctional compound may further be added to the UV-curable resin composition of the present invention as the component (B).
  • the polymerizable polyfunctional compound trimethylolpropane tri(meth)acrylate, trimethylolpropanetrioxyethyl (meth)acrylate, pentaerythritol tri(meth)acrylate, ethylene glycol di(meth)acrylate, triethylene glycol diacrylate, tetraethylene glycol di(meth)acrylate, tricyclodecanediyldimethanol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 1 ,4-butanediol di(meth)acrylate, 1 ,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, both terminal (me
  • tricyclodecanediyldimethanol di(meth)acrylate di(meth)acrylate of ethylene oxide addition diol of bisphenol A
  • tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate tri(meth)acrylate
  • 1 ,6-hexanediol di(meth)acrylate are preferable.
  • the polymerizable polyfunctional compound contained in the component (B) is commercially available as Yupimer UV, SA-1002 (manufactured by Mitsubishi Chemical Corp.), Aronix M-215, M-315, M-325, TO-1210 (manufactured by Toagosei Co., Ltd.), GX-8345(manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and the like.
  • the polymerizable polyfunctional compound is used in an amount of preferably 20 to 80 wt%, and more preferably 40 to 70 wt% for 100 wt% of the component (B) in total.
  • the photoinitiator (C) added to the UV-curable resin composition of the present invention is a component which increases the absorbance at 365 nm of the UV-curable resin composition of the present invention.
  • the absorbance at 365 nm of the resin composition is increased by adding the photoinitiator (C).
  • the photoinitiator (C) (0.1 wt% solution) must have an absorbance (optical length: 1 cm) at 365 nm of 0.2 or more.
  • the absorbance at 365 nm of the resin composition of the present invention is increased by using a photoinitiator having an absorbance within the above-mentioned range, whereby excellent curability can be obtained when using an LED light source having a sharp emission spectrum at 365 nm.
  • the absorbance at 365 nm of a 0.1 wt% solution is determined by measuring the absorbance of a sample, which is prepared by dissolving the component (C) in an appropriate organic solvent (e.g.
  • toluene or acetonitrile which does not substantially absorb light having a wavelength of 365 nm, at a concentration of 0.1 wt%, and measuring the absorbance of a reference sample (organic solvent used) by using a UV spectrophotometer using a measurement cell having an optical length of 1 cm.
  • a reference sample organic solvent used
  • the compounds (i), (ii), and (iii) respectively have an absorbance (optical length: 1 cm) at 365 nm as high as about 0.7, about 0.4, and 1 or more (0.1 wt% solution).
  • the optical absorption characteristics of such a compound increase the absorbance at 365 nm of the UV-curable resin composition of the present invention including such a compound.
  • the compounds (i), (ii), and (iii) used as the photoinitiator (C) commercially available products may be used.
  • these compounds (i) Lucirin TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide; manufactured by BASF), (ii) lrgacure 907 (2-methyl-1-[4-methylthiophenyl]-2- morpholino-propan-1-one; manufactured by Ciba Specialty Chemicals Inc.), and (iii) lrgacure 369 (2-benzyl-2-dimethylamino-1-(4-morphorinophenyl)-butanone-1 , manufactured by Ciba Specialty Chemicals Inc.) can be given.
  • a photoinitiator which has an absorbance (optical length: 1 cm) at 365 nm of less than 0.2 (0.1 wt% solution) and therefore does not fall under the component (C), benzyl methyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and the like can be given.
  • the photoinitiator (C) is added in an amount of 0.1 to 15 wt%, and preferably 0.3 to 10 wt%, provided that the total amount of the UV-curable resin composition of the present invention is 100 wt%. If the amount of the photoinitiator is 0.1 to 15 wt%, the absorbance at 365 nm of the UV-curable resin composition of the present invention can be increased, whereby the curability can be improved when using the LED light source.
  • UV-curable resin composition of the present invention Various components may be added to the UV-curable resin composition of the present invention insofar as the effect of the present invention is not impaired.
  • an antioxidant, UV absorber, light stabilizer, aging preventive, silane coupling agent, anti-foaming agent, leveling agent, antistatic agent, surfactant, preservative, thermal polymerization inhibitor, plasticizer, and wettability improver can optionally be added to the UV-curable resin composition of the present invention.
  • the UV-curable resin composition of the present invention is prepared as follows.
  • a reaction vessel equipped with a stirrer is charged with the components (A) to (C), and the mixture is stirred at 20 to 60 0 C until a homogenous solution is obtained.
  • the UV-curable resin composition of the present invention exhibits particularly excellent curability when cured by application of light (UV light) having a wavelength of 365 nm.
  • UV light light
  • the UV-curable resin composition of the present invention may also be cured by application of UV light, visible rays, electron beams, or the like in the same manner as a photocurable resin composition.
  • the UV-curable resin composition of the present invention exhibits excellent adhesion to plastic such as polycarbonate (PC) or polymethyl methacrylate (PMMA), a metal such as gold, aluminum, or silver, silicon, a mixture thereof, or an inorganic compound such as glass. Therefore, the composition is suitable as an optical disk adhesive.
  • plastic such as polycarbonate (PC) or polymethyl methacrylate (PMMA)
  • metal such as gold, aluminum, or silver, silicon, a mixture thereof, or an inorganic compound such as glass. Therefore, the composition is suitable as an optical disk adhesive.
  • the UV-curable resin composition of the present invention exhibits excellent curability and adhesion when bonding optical disks using an LED light source having a sharp emission spectrum at 365 nm. Therefore, the composition is useful as a optical disk (DVD) adhesive.
  • DVD optical disk
  • the composition of the present invention is provided between the optical disks to form an adhesive layer with a thickness of 10 to 100 ⁇ m.
  • the adhesive layer is then cured by applying light having a wavelength of 365 nm (UV light) from an LED light source to cause the optical disks to adhere.
  • the UV-curable resin composition of the present invention is suitable as an adhesive for a DVD, a polymer film, a resin sheet, and the like.
  • the UV-curable resin composition is particularly suitable for bonding a film or a resin sheet for which optical properties are required. Moreover, since the UV-curable resin composition of the present invention exhibits excellent adhesion, heat resistance, water resistance, and formability, the UV-curable resin composition is useful as an adhesive composition. In particular, since the UV-curable resin composition of the present invention exhibits excellent adhesion to an MS film or a PET film, the composition is suitably used to laminate an MS film or a PET film on a vinyl chloride sheet. Moreover, the composition is also useful as a building material, packaging material, printing material, display material, electric/electronic material, optical material, liquid crystal panel material, and the like.
  • a reaction vessel equipped with a stirrer was charged with 12.4 g of isophorone diisocyanate and 0.009 g of 2,6-di-t-butyl-p-cresol. Since the viscosity of the mixture is increased in the second half of the reaction, 20.4 g of ethylene glycol diacrylate (manufactured by Kyoeisha Chemical Co., Ltd.) was added to the mixture as a diluting component. Then, the mixture was cooled with ice to 1O 0 C with stirring.
  • Example 1 preparation of UV-curable resin composition
  • Examples 2 to 4 and Comparative Example 1 A resin composition was produced in the same manner as in Example 1 except for using components in amounts shown in Table 1. The curability of the resulting resin composition was evaluated by measuring the absorbance (%) at 365 nm. The evaluation results of the compositions of the examples and comparative example are shown in Table 1.
  • the absorbance measurement method and the curability evaluation method are as follows. ⁇ Absorbance (%) at 365 nm>
  • the resin composition was applied to a quartz plate to a thickness of 50 ⁇ m by spin coating to obtain a sample.
  • a quartz plate to which the resin composition was not applied was used as a reference sample.
  • the transmittance (%) of the sample at 365 nm was measured by using a spectrophotometer ("U-3410" manufactured by Hitachi Ltd.). The absorbance was calculated as follows.
  • the resin composition was applied to an aluminum-deposited PC substrate to a thickness of 50 ⁇ m by spin coating, and a PC substrate was placed over the applied composition.
  • the composition was then irradiated from the PC side by using an LED lamp having an emission peak at 365 nm, to cause the substrates to adhere.
  • the aluminum-deposited PC substrate and the cured resin were separated by using a utility knife, and the presence or absence of tackiness on the surface of the cured resin was confirmed with the finger to evaluate the curability.
  • a cured resin which exhibited no tackiness over the entire surface including the end face was evaluated as "excellent”, a cured resin which exhibited tackiness only at the end face was evaluated as “good”, and a cured resin which exhibited tackiness over the entire surface was evaluated as "bad”.
  • Component (B) Epoxy diacrylate: "VR-77” manufactured by Showa Highpolymer Co., Ltd.
  • the UV-curable resin composition of the present invention is suitable for a polymer film and a resin sheet, particularly suitable for a film or a resin sheet for which optical properties are required. Since the UV-curable resin composition of the present invention exhibits excellent adhesion, heat resistance, water resistance, and formability, the UV-curable resin composition is useful as an adhesive composition.
  • the UV-curable resin composition exhibits excellent adhesion to an MS film or a PET film
  • the composition is suitably used to laminate an MS film or a PET film on a vinyl chloride sheet.
  • the UV-curable resin composition is also useful for building materials, packaging materials, printing materials, display materials, electric/electronic materials, optical materials, liquid crystal panel materials, and the like.
  • the UV-curable resin composition of the present invention is particularly useful as a photocurable adhesive used when bonding optical disks (DVD) utilizing an LED light source having a sharp emission spectrum at 365 nm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition de résine durcissable par rayonnement UV, appropriée comme adhésif pour un matériau polymère ou similaire. Plus particulièrement, la présente invention concerne une composition d'adhésif liquide durcissable utilisée dans les domaines des disques optiques (DVD), des matériaux de construction, d'emballage, d'impression, d'affichage, de pièces électriques et électroniques, de pièces optiques, de panneaux à cristaux liquides et similaire.
PCT/NL2005/000766 2004-10-29 2005-10-26 Composition de resine photodurcissable et adhesif pour disque optique Ceased WO2006046864A1 (fr)

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JP2004315794A JP2006124549A (ja) 2004-10-29 2004-10-29 光硬化性樹脂組成物及び光ディスク用接着剤
JP2004-315794 2004-10-29

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EP2174781A4 (fr) * 2007-07-30 2011-02-23 Asahi Glass Co Ltd Composition de résine durcissable, stratifié transparent l'utilisant et procédé pour produire le stratifié transparent
WO2011092200A1 (fr) 2010-01-28 2011-08-04 Bayer Materialscience Ag Dvd haute vitesse
CN110305589A (zh) * 2019-07-23 2019-10-08 新纶科技（常州）有限公司 一种uv型耐水煮的丙烯酸酯胶黏剂及其胶带的制备方法
CN112662318A (zh) * 2020-12-22 2021-04-16 上海康达化工新材料集团股份有限公司 一种用于小家电粘接抗摔的uv胶

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JP5069662B2 (ja) * 2007-11-12 2012-11-07 リンテック株式会社 粘着シート
US20090123746A1 (en) 2007-11-12 2009-05-14 Lintec Corporation Adhesive sheet
CN101245179B (zh) * 2008-03-13 2011-01-12 武汉理工大学 一种改善热塑性塑料成型工艺性与性能的方法
KR20100009473A (ko) * 2008-07-18 2010-01-27 주식회사 엘지화학 편광판 및 액정표시장치
KR20100009472A (ko) 2008-07-18 2010-01-27 주식회사 엘지화학 액정표시장치
RU2554650C2 (ru) * 2009-12-17 2015-06-27 ДСМ АйПи ЭССЕТС Б.В. Светодиодное отверждение радиационно-отверждаемых покрывных композиций оптических волокон
CN102898958B (zh) * 2011-07-25 2016-11-02 汉高股份有限公司 一种粘合剂组合物
WO2017168699A1 (fr) * 2016-03-31 2017-10-05 日立化成株式会社 Composition de résine photosensible, film de résine photosensible, procédé de production de produit durci, stratifié et composant électronique
KR102139462B1 (ko) * 2018-11-28 2020-07-30 에이케이켐텍 주식회사 Uv 경화형 유리 접착용 아크릴 수지 조성물 및 이로부터 제조되는 성형체
KR20250078437A (ko) * 2022-10-03 2025-06-02 디아이씨 가부시끼가이샤 경화성 조성물, 그 경화물, led 소자, 전자 디바이스 및 광학 소자

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EP2174781A4 (fr) * 2007-07-30 2011-02-23 Asahi Glass Co Ltd Composition de résine durcissable, stratifié transparent l'utilisant et procédé pour produire le stratifié transparent
US8268447B2 (en) 2007-07-30 2012-09-18 Asahi Glass Company, Limited Curable resin composition, transparent laminate using the same, and process for producing the transparent laminate
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WO2011092200A1 (fr) 2010-01-28 2011-08-04 Bayer Materialscience Ag Dvd haute vitesse
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CN110305589A (zh) * 2019-07-23 2019-10-08 新纶科技（常州）有限公司 一种uv型耐水煮的丙烯酸酯胶黏剂及其胶带的制备方法
CN112662318A (zh) * 2020-12-22 2021-04-16 上海康达化工新材料集团股份有限公司 一种用于小家电粘接抗摔的uv胶

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