KR20040030398A - Adhesive composition for optical disks - Google Patents

Abstract

The present invention

(A) radiation-curable oligomers obtainable by reacting polyol compounds, polyisocyanate compounds and hydroxyl group-containing (meth) acrylate compounds, for example urethane (meth) acrylates; And

(B) relates to an adhesive composition for an optical disc containing dialkylaminobenzoate, and

(C) hydroxyalkyl (meth) acrylate; And

(D) 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 1-hydroxycyclohexyl phenyl ketone A composition comprising at least one compound selected from the group together with a radiation-curable oligomer (A),

The composition of the present invention is used as an adhesive for an optical disc.

Description

Adhesive composition for optical discs {ADHESIVE COMPOSITION FOR OPTICAL DISKS}

Recent advances in information technology, represented by computer technology, computer software technology, and communication technology, enable the transfer of more information at higher speeds. Accordingly, a recording medium capable of recording more information at a higher density is required and developed. As the high-density recording medium, a DVD (digital video disc or digital versatile disk) is being developed as a next-generation multipurpose recording medium. DVDs are usually made by bonding two disks together, so that an adhesive is required to bond the two disks together. Examples of conventional adhesives include hot melt adhesives, heat-curable adhesives, and oxygen-free curable adhesives. However, these conventional adhesives have several disadvantages. For example, hot melt adhesives are poor in thermal stability and weather resistance, softening at high temperatures to reduce adhesiveness, causing the disk to separate or deform. And because of the poor transparency of the hot melt adhesive, it is difficult to apply the hot melt adhesive to a two-layer DVD having a semi-transmissive film as a recording film. A problem with heat-curable adhesives is that the substrate forming the disk is deformed by heat during curing. Alternatively, if low temperatures are used, it takes a long time to cure the adhesive. Anoxic curable adhesives exhibit poor productivity because they require a long time to cure the adhesive. Photocurable adhesives have been proposed to solve this problem. For example, Japanese Patent Application Laid-Open Nos. 142545/1986 and 89462/1994 disclose UV-curable resin adhesives containing urethane acrylate as an essential component. However, the UV-curable resin adhesives are unsatisfactory in terms of curability at disk edges, adhesion to gold to form semi-transmissive films, moisture-heat resistance, and the like. It is therefore an object of the present invention to provide a UV-curable resin composition for an optical disc having improved curability at the edge of the disc.

It is also an object to provide a resin composition having improved adhesion to gold or the like.

It is also an object of the present invention to provide a composition having improved moisture-heat resistance compared to conventional adhesives.

Summary of the Invention

As a result of extensive research, the inventors have confirmed that the above objects can be achieved by combining the radiation-curable oligomer with the following components (B) and / or (C) and (D).

Therefore, the present invention

(A) a radiation-curable oligomer prepared by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound, preferably a urethane (meth) acrylate oligomer; And

Provided is a composition comprising (B) dialkylaminobenzoate.

In addition, the present invention

(A) a radiation-curable oligomer prepared by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound, preferably a urethane (meth) acrylate oligomer;

(C) hydroxyalkyl (meth) acrylate; And

(D) 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 1-hydroxycyclohexyl phenyl ketone Provided are compositions comprising at least one compound selected from the group.

It is preferable that the composition of this invention contains all four components (A)-(D).

The invention also provides the use of the composition for use as an adhesive for optical discs, such as digital general purpose discs.

The present invention also provides an optical disc, such as a digital multipurpose disc, comprising an adhesive obtainable by curing the composition of the present invention.

The present invention relates to a photocurable composition. The present invention also relates to the use of the composition for use as an adhesive for optical discs.

The oligomers used as component (A) are suitable radiation-curable oligomers, such as (meth) acrylate oligomers. Component (A) is a urethane (meth) acrylate oligomer obtainable by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound.

Polyol compounds include polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, aliphatic hydrocarbons having two or more hydroxyl groups in the molecule, aliphatic rings having two or more hydroxyl groups in the molecule Hydrocarbons, unsaturated hydrocarbons having two or more hydroxyl groups in the molecule, and the like can be used. The polyols can be used individually or in combination of two or more.

Examples of polyether polyols may be aliphatic polyether polyols, aliphatic ring polyether polyols and aromatic polyether polyols.

Examples of aliphatic polyether polyols include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, pentaerythritol, dipentaerythritol, trimethylolpropane; Polyalcohols, such as alkylene oxide added polyols, such as ethylene oxide added triols of trimethylolpropane, ethylene oxide / propylene oxide added triols of trimethylolpropane, ethylene oxide added tetraols and pentaerythritol Ethylene oxide addition hexaol of pentaerythritol; Polyether polyols obtained by ring-opening polymerization of two or more ion-polymerizable cyclic compounds; Etc.

Examples of ion-polymerizable cyclic compounds include cyclic ethers such as ethylene oxide, propylene oxide, butene-1-oxide, isobutene oxide, 3,3-bis (chloromethyl) oxetane, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane, trioxane, tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl ether, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monoox Seeds, isoprene monooxide, vinyl oxetane, vinyl tetrahydrofuran, vinyl cyclohexene oxide, phenyl glycidyl ether, butyl glycidyl ether, and glycidyl benzoate can be provided. Specific combinations of two or more ion-polymerizable cyclic compounds include tetrahydrofuran and ethylene oxide, tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyltetrahydrofuran, tetra Combination of hydrofuran and 3-methyltetrahydrofuran, combination of ethylene oxide and propylene oxide, combination of butene-1-oxide and ethylene oxide, tetrahydrofuran, butene-1-oxide and ethylene oxide Combinations and the like can be provided.

Polyether polyols obtained by ring-opening copolymerization of such ion-polymerizable cyclic compounds with cyclic imines such as ethyleneimine, cyclic lactone acids such as β-propiolactone and glycolic acid lactide or dimethylcyclopolysiloxane Can be used.

Examples of the alicyclic polyether polyols may be provided with alkylene oxide addition diols of hydrogenated bisphenol A, alkylene oxide addition diols of hydrogenated bisphenol F, alkylene oxide addition diols of 1,4-cyclohexanediol, and the like. .

Examples of aromatic polyether polyols include alkylene oxide addition diols of bisphenol A, alkylene oxide addition diols of bisphenol F, alkylene oxide addition diols of hydroquinone, alkylene oxide addition diols of naphthohydroquinone, anthrahydroquinone Alkylene oxide addition diols and the like can be provided.

Examples of commercially available products of aliphatic polyether polyols include PTMG 650, PTMG 1000, PTMG 2000 (manufactured by Mitsuibishi Chemical Corp.), PPG 1000, EXCENOL 1020, EXCENOL 2020, EXCENOL 3020, EXCENOL 4020 (Asahi Glass Co., Ltd.). Problem), PEG 1000, Unisafe DC 1100, Unisafe DC 1800, Unisafe DCB 1100, Unisafe DCB 1800 (manufactured by Nippon Oil and Fats Co., Ltd.), PPTG 1000, PPTG 2000, PPTG 4000, PTG 400, PTG 650, PTG 2000, PTG 3000, PTGL 1000, PTGL 2000 (manufactured by Hodogaya Chemical Co., Ltd.), PPG 400, PBG 400, Z-3001-4, Z-3001-5, PBG 2000, PBG 2000B (Daiichi Kogyo Seiyaku Co , Ltd.), TMP30, PNT4 Glycol, EDA P4, EDA P8 (manufactured by Nippon Nyukazai Co., Ltd.) and Quadrol (manufactured by Asahi Denka Kogyo KK). Examples of commercially available products of aromatic polyether polyols may be provided by Uniol DA400, DA700, DA1000, DB400 (manufactured by Nippon Oil and Fats Co., Ltd.) and the like.

Polyester polyols are obtained by reacting polyhydric alcohols with polybasic acids. Examples of polyhydric alcohols include ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7 Heptanediol, 1,8-octanediol, neopentyl glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,2-bis (hydroxyethyl) cyclohexane, 2,2-di Ethylene jade of ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol, 2-methyl-1,8-octanediol, glycerol, trimethylolpropane, trimethylolpropane Seed addition products, propylene oxide addition products of trimethylolpropane, ethylene oxide and propylene oxide addition products of trimethylolpropane, sorbitol, pentaerythritol, dipentaerythritol, alkylene oxide addition polyols and the like can be provided. have. Examples of polybasic acids may be provided with phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid, sebaic acid and the like. Examples of commercially available products of polyester polyols may include Kurapol P1010, Kurapol P2010, PMIPA, PKA-A, PKA-A2, PNA-2000 (manufactured by Kuraray Co., Ltd.) and the like.

As an example of the polycarbonate polyol, a polycarbonate diol represented by the following Chemical Formula 1 may be provided:

(In Formula 1, R ¹ represents an alkylene group having 2-20 carbon atoms, a (poly) ethylene glycol residue, a (poly) propylene glycol residue, or a (poly) tetramethylene glycol residue. Is an integer)

Specific examples of the group represented by R ¹ include 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 1,7-heptanediol, 1 Hydroxyl groups at both ends from 8-octanediol, 1,9-nonanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and the like The residue obtained by removing can be provided. Examples of commercially available products of polycarbonate polyols include DN-980, DN-981, DN-982, DN-983 (manufactured by Nippon Polyurethane Industry Co., Ltd.), PC-8000 (manufactured by PPG), PNOC1000, PNOC2000 , PMC100, PMC2000 (manufactured by Kuraray Co., Ltd.), PLACCEL CD-205, CD-208, CD-210, CD-220, CD-205PL, CD-208PL, CD-210PL, CD-220PL, CD-205HL , CD-208HL, CD-210HL, CD-220HL, CD-210T, CD-221T (manufactured by Daicel Chemical Industries, Ltd.) and the like.

Examples of polycaprolactone polyols include ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1 Polycaprolactone diols obtained by addition reaction of diols such as, 4-cyclohexanedimethanol or 1,4-butanediol with ε-caprolactone can be provided. Examples of commercially available products of the polycaprolactone diol may include PLACCEL 205, 205AL, 212, 212AL, 220, 220AL (manufactured by Daicel Chemical Industries, Ltd.) and the like.

Examples of aliphatic hydrocarbons having two or more hydroxyl groups in the molecule include ethylene glycol, propylene glycol, tetramethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7 -Heptanediol, 1,8-octanediol, 1,9-nonanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-methyl -1,8-octanediol, hydrogenated polybutadiene with terminal hydroxyl groups, glycerol, trimethylolpropane, pentaerythritol, sorbitol and the like can be provided.

Examples of alicyclic hydrocarbons having two or more hydroxyl groups in the molecule include 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,2-bis (hydroxyethyl) cyclohexane, dicyclo Dimethylol compounds of pentadienes, tricyclodecanedimethanol and the like can be provided.

Examples of unsaturated hydrocarbons having two or more hydroxyl groups in a molecule may be provided with polybutadiene having terminal hydroxyl groups, polyisoprene having terminal hydroxyl groups, and the like.

Examples of polyols other than the polyols may be β-methyl-δ-valerolactonediol, castor oil-modified diols, terminal diol compounds of polydimethylsiloxane, polydimethylsiloxanecarbitol-modified diols, and the like.

The polystyrene-reduced number average molecular weight of the polyol as measured by gel permeation chromatography (GPC) is preferably 50-15,000, and particularly preferably 250-800.

As a polyisocyanate compound, a diisocyanate compound is preferable. Examples of diisocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, 1,5-naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethylphenyl Ethylene diisocyanate, 4,4'-biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, bis (2-isocyanate ethyl) fumarate, 6-isopropyl-1,3-phenyl diisocyanate, 4-diphenylpropane diisocyanate, lysine diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylene diisocyanate, tetramethyl xylene diisocyanate Oh, there are carbonate, etc. can be provided. Among the above, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated xylene diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate and the like are particularly preferable. The diisocyanates can be used individually or in combination of two or more.

The hydroxyl group-containing (meth) acrylate has a hydroxyl group in the ester moiety. 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, 1 , 4-butanediol mono (meth) acrylate, 2-hydroxyalkyl (meth) acryloyl phosphate, 4-hydroxycyclohexyl (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, neo Pentyl glycol mono (meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolethane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, (Meth) acrylates represented by the following formula (2) may be provided as an example thereof:

(In Formula 2, R ² represents a hydrogen atom or a methyl group, n is an integer of 1 to 15, preferably 1 to 4)

And compounds containing glycidyl groups, such as alkyl glycidyl ethers, allyl glycidyl ethers, or compounds obtained by addition reactions of glycidyl (meth) acrylate and (meth) acrylic acid may also be provided. have. Among the above, hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate are particularly preferred.

There is no particular limitation on the method of synthesizing urethane (meth) acrylate. For example, the following methods (i) to (i) can be used.

(Iii) A method of reacting a polyisocyanate with a hydroxyl group-containing (meth) acrylate and then reacting the product with a polyol.

(Ii) A method of reacting a polyol, a polyisocyanate and a hydroxyl group-containing (meth) acrylate together.

(Iii) A method of reacting a polyol with a polyisocyanate and then reacting the product with a hydroxyl group-containing (meth) acrylate.

Copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyltin dilaurate, triethylamine, 1,4-diazabicyclo [2.2.2] octane, or 1,4-diaza It is preferable to synthesize the urethane (meth) acrylate used in the present invention by using a urethanization catalyst such as 2-methylbicyclo [2.2.2] octane in an amount of 0.01-1 part by weight based on 100 parts by weight of the reaction product. Do.

The number average molecular weight of the urethane (meth) acrylate used in the present invention is preferably 400-20,000 and particularly preferably 700-5,000.

The proportion of urethane (meth) acrylate in the composition of the present invention is preferably 20-80 wt% in terms of adhesion and viscosity to the substrate of the composition, relative to the total weight of the composition.

Examples of component (B) used in the present invention include alkyl esters of dialkylaminobenzoic acids (alkyl dialkylaminobenzoates) (methyl esters, ethyl esters, propyl esters, butyl esters, isoamyl esters, and the like). Preferred alkyl groups for the dialkylamino group include alkyl groups having 1-6 carbon atoms. As the ester moiety, an alkyl group having 1-6 carbon atoms is preferable. The dialkylamino group and the carboxylate group are preferably bonded to the benzene ring at the p-position. When curing the composition located between two disks, component (B) prevents stickiness and improves the curability at the edges of the disks. Among the above, ethyl p-dimethylaminobenzoate is preferred.

Examples of commercially available products used as component (B) may be KAYACURE EPA, KAYACURE DMBI (manufactured by Nippon Kayaku Co., Ltd.) and the like.

The proportion of component (B) in the composition of the present invention is preferably 0.05-5 wt%, more preferably 0.1-3 wt% and particularly preferably 0.2-1 wt%, based on the total weight of the composition, in view of edge curability and moisture-heat resistance. to be.

Examples of component (C) used in the present invention include hydroxy C ₁ -C ₆ alkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Component (C) improves moisture-heat resistance. Among the above, 4-hydroxybutyl (meth) acrylate is preferable.

Examples of commercially available products used as component (C) include HEA, HPA, 4HBA (manufactured by Osaka Organic Chemical Industry Co., Ltd.), Light Ester HOA, Light Ester HOP-A, Light Ester HO, Light Ester HOP , Light Ester HOB (manufactured by Kyoeisha Chemical Co., Ltd.) and the like can be provided.

The proportion of hydroxyalkyl (meth) acrylates used as component (C) is preferably 5-70 wt% and more preferably 10-50 wt%, based on the total weight of the composition in order to improve moisture-heat resistance.

Component (D) as a photoinitiator is 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 1-hydroxycyclohexyl At least one compound selected from the group consisting of phenyl ketones. It is preferable to use a combination of 2,2-dimethoxy-1,2-diphenylethan-1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one. The proportion of component (D) in the composition of the present invention is preferably 0.01-15 wt%, more preferably 0.1-10 wt%, based on the total weight of the composition, in view of moisture-heat resistance and curability.

Examples of commercially available products used as component (D) may be provided by Irgacure 184, 500, 651, Darocur 1173, 4265 (manufactured by Ciba Specialty Chemicals Co., Ltd.) and the like.

In order to improve the adhesion to gold, it is preferred to add a methoxysilyl group-containing thiol compound to the adhesive composition for the optical disc of the present invention as component (E). Examples of the methoxysilyl group-containing thiol compound include mercaptoalkyl monomethoxysilane, mercaptoalkyldimethoxysilane, and mercaptotrimethoxysilane such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyl Methyl monomethoxysilane and γ-mercaptopropylmethyldimethoxysilane can be provided. If component (E) is used, its proportion in the composition of the present invention is 0.1-5 wt%, and more preferably 0.3-3 wt%, based on the total weight of the composition in terms of adhesion to gold and moisture-heat resistance.

Examples of commercially available products that can be used as component (E) include SH6062, AY43-062 (manufactured by Toray-Dow Corning Silicone Co., Ltd.), Sila-Ace S810 (manufactured by Chisso Corp.) and KBM803 (Shin- Etsu Chemical Co., Ltd.).

In addition to component (C), a (meth) acrylate compound containing at least one (meth) acryloyl group in the molecule may be added to the composition of the present invention. Either a monofunctional compound containing one (meth) acryloyl group and a polyfunctional compound containing two or more (meth) acryloyl groups can be used. The compounds may be used in combination in appropriate proportions.

Examples of such monofunctional compounds include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, amyl (meth) acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) Acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate , Dodecyl (meth) acrylate, lauryl (meth) acrylate, octadecyl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, butoxyethyl (meth Acrylate, ethoxydiethylene glycol (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol Mono (meth) acrylate, methoxyethylene glycol Mono (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxy Polypropylene glycol (meth) acrylate, dicyclopentadienyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, tricyclodecanyl (meth) acrylate, bor Neyl (meth) acrylate, Isobornyl (meth) acrylate, Adamantyl (meth) acrylate, Dimethylaminoethyl (meth) acrylate, Diethylaminoethyl (meth) acrylate, 7-amino-3,7-dimethoxyoctyl (meth) acrylate, (meth) acryloyl morpholine, 2- (meth) acryloyloxyethylphthalic acid, 2- (Meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxypropylphthalic acid, 2- (meth) acryloyloxypropyltetrahydrophthalic acid, 2- (meth) acryloyloxypropylhexahydro Phthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, trifluoroethyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, hexafluoropropyl (meth) acrylate, octafluoropentyl (meth ) Acrylate, heptadecafluorodecyl (meth) acrylate, mono [2- (meth) acryloyloxyethyl] phosphate, mono [2- (meth) acryloyloxyethyl] diphenyl phosphate, mono [2 -(Meth) acryloyloxypropyl] phosphate and the following formula 3-5 There are compounds represented by:

(In Formula 3, R ³ represents a hydroxyalkylene group or alkylene group having 2-6 carbon atoms, R ⁴ represents a hydrogen atom or a methyl group, R ⁵ is an alkyl group or hydrogen atom having 1-12 carbon atoms. P is an integer from 0 to 20)

(In Formula 4, R ⁶ represents a hydrogen atom or a methyl group, R ⁷ represents an alkylene group having 2-8 carbon atoms, q is an integer of 0 to 8)

(In Formula 5, R ⁸ represents a hydrogen atom or a methyl group, R ⁹ represents an alkylene group having 2-8 carbon atoms, r is an integer of 0 to 8, R ¹⁰ and R ¹¹ is 1-6 Alkyl group or hydrogen atom having a carbon atom)

Examples of commercially available products of such monofunctional compounds include Aronix M101, M102, M110, M111, M113, M114, M117, M120, M152, M154, M5300, M5400, M5500, M5600 (manufactured by Toagosei Co., Ltd.) , KAYARAD TC-110S, R-128H, R629, R644 (manufactured by Nippon Kayaku Co., Ltd.), IPAA, AIB, SBAA, TBA, IAAA, HEXA, CHA, NOAA, IOAA, INAA, LA, TDA, MSAA, CAA, HDAA, LTA, STA, ISAA-1, ODAA, NDAA, IBXA, ADAA, TCDA, 2-MTA, DMA, Viscoat # 150, # 150D, # 155, # 158, # 160, # 190, # 190D, # 192, # 193, # 220, # 320, # 2311HP, # 2000, # 2100, # 2150, # 2180, MTG (manufactured by Osaka Organic Chemical Industry Co., Ltd.), NK Ester M-20G, M-40G , M-90G, M-230G, CB-1, SA, S, AMP-10G, AMP-20G, AMO-60G, AMP-90G, A-SA, NLA (manufactured by Shin-Nakamura Chemical Co., Ltd.) , ACMO (manufactured by Kojin Co., Ltd.), Light Acrylate IA-A, LA, SA, BO-A, EC-A, MTG-A, DPM-A, PO-A, P-200A, THF-A, IB-XA, HOA-MS, HOA-MPL, HOA-MPE, HOA-HH, IO-A, BZ-A, NP-EA, NP-10EA, HOB-A, FA-108, Epoxy Ester M-600A, Light Ester PM (manufactured by Kyoeisha Chemical Co., Ltd.), FA-511, FA-512A, FA-513A (Hitac hi Chemical Co., Ltd.), AR-100, MR-100, MR-200, MR-260 (manufactured by Daihachi Chemical Co., Ltd.), JAMP-100, JAMP-514, JPA-514 (Johoku Chemical Co., Ltd.).

Examples of the multifunctional compound include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylic Latex, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, Ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, trimethylolpropanetrioxyethyl (meth) acrylate, trimethylolpropanepolyoxy Ethyl (meth) acrylate, trimethylolpropanetrioxypropyl (meth) acrylate, trimethylolpropanepolyoxyethyl (meth) acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, Tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, ethylene oxide added bisphenol A di (meth) acrylate, ethylene oxide added bisphenol F di (meth) acrylate, propylene oxide added bisphenol A di (meth) acrylate, propylene oxide addition bisphenol F di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylic Bisphenol A diepoxy di (meth) acrylate, bisphenol F diepoxy di (meth) acrylate, bis [2- (meth) acryloyl oxyethyl] phosphate, bis [2- (meth) acryloyloxy Propyl] phosphate, tris [2- (meth) acryloyloxyethyl] phosphate, and the like.

Examples of commercially available products of the multifunctional compound include SA-1002, SA-2006, SA-2007, SA-4100, SA-5001, SA-6000, SA-7600, SA-8000, SA-9000 (Mitsubishi Chemical Corp.), Viscoat # 195, # 195D, # 214HP, # 215, # 215D, # 230, # 230D, # 260, # 295, # 295D, # 300, # 310HP, # 310HG, # 312, # 335HP, # 335D, # 360, GPT, # 400, # 540, # 700, GPT, Viscoat 3PA (manufactured by Osaka Organic Chemical Industry Co., Ltd.), KAYARAD MANDA, R-526, NPGDA, PEG400DA, R-167 , HX-220, HX-620, R-551, R-712, R-604, R-684, GPO-303, TMPTA, THE-330, TPA-320, TPA-330, PET-30, RP-1040 , T-1420, DPHA, D-310, D-330, DPCA-20, DPCA-30, DPCA-60, DPCA-120 (manufactured by Nippon Kayaku Co., Ltd.), Aronix M-210, M-208, M-215, M-220, M-225, M-233, M-240, M-245, M-260, M-270, M-305, M-309, M-310, M-315, M- 320, M-350, M-360, M-400, M-408, M-450 (manufactured by Toagosei Co., Ltd.), SR-212, SR-213, SR-355 (manufactured by Sartomer Co., Ltd.) ), SP-1506, SP-1507, SP-1509, SP-1519-1, SP-1563, SP-2500, VR60, VR77, VR90 (manufactured by Showa Highpolymer Co., Ltd.), Light Ester P-2M ( Kyoeisha Ch emical Co., Ltd.), EB-169, EB-179, EB-3603, and R-DX63182 (manufactured by Daicel-UCB Co., Ltd.).

Photoinitiators other than component (D) may be added to the compositions of the present invention. Examples of such other photoinitiators include 3-methylacetophenone, 2,2-dimethoxy-2-phenylacetophenone, xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone, triphenylamine, carbazole, 3-methylaceto Phenone, benzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, benzoin ethyl ether, benzoin propyl ether, Mikler ketone, benzyl dimethyl ketal, 1 -(4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- ( 2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one, 2 , 4,6-trimethylbenzoylphenylphosphinate, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1 -One, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, methyl benzoyl fort Mate, thioxanthone, diethyl thioxanthone, 2-isopropyl thioxanthone, 2-chlorothioxanthone, and oligo [2-hydroxy-2-methyl-1- [4- (1-methylvinyl) Phenyl] propanone. The compounds can be used to increase the surface hardenability and curing rate of the composition. If used in combination with compound (D), the other photoinitiators are preferably present in an amount of up to 70 wt%, based on the total weight of the combination of compound (D) and the other photoinitiator.

Examples of commercially available products of the other photoinitiators include IRGACURE 261, 369, 907, 819, 1700, 1800, 1850, 2959, CGI-403, Darocur 953, 1116, 1664, 2273 (Ciba Specialty Chemicals Co., Ltd. Lucirin TPO, LR8728, LR8893 (BASF), Ubecryl P36 (UCB), VICURE55 (Akzo), ESACURE KIP100F, KIP150 (Lamberti), KAYACURE CTX, DETX, BP-100, BMS and 2-EAQ (Made by Nippon Kayaku Co., Ltd.).

Silane binders other than component (E) may be added to the compositions of the present invention. Examples of the silane binder include γ-mercaptopropylmethyl monoethoxysilane, γ-mercaptopropyldiethoxysilane, γ-mercaptopropyltriethoxysilane, β-mercaptoethyl monoethoxysilane, β-mercaptoethyl Triethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxylpropyltrimethoxysilane, γ-glycidoxylpropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-chloropropylmethyldimethoxysilane, γ- Chloropropyltrimethoxysilane and γ-methacryloyloxypropyltrimethoxysilane. Examples of commercially available products of the silane binder include Sila-Ace S310, S311, S320, S321, S330, S510, S520, S530, S610, S620, S710 (manufactured by Chisso Corp.), SH6060, SZ6023, SZ6030, SH6040 , SH6076, SZ6083 (manufactured by Toray-Dow Corning Silicone Co., Ltd.), KBM403, KBM503, KBM602, KBM603, KBE903 (manufactured by Shin-Etsu Chemical Industries Co., Ltd.).

In addition to the acryl group-containing compound, radically polymerizable compounds may be added to the compositions of the present invention. Examples of such compounds are N-vinylpyrrolidone, N-vinylcaprolactam, vinyl acetate, vinyl propionate, styrene, divinylbenzene and unsaturated polyesters. The unsaturated polyesters include esters of alcohols with dicarboxylic acids having radical polymerizable unsaturated double bonds. Examples of dicarboxylic acids having radically polymerizable unsaturated double bonds are maleic anhydride, itaconic acid, and fumaric acid. Examples of alcohols include polyhydric alcohols such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-hexanol, cyclohexanol And 2-ethylhexyl alcohol; (Poly) ethylene glycols such as ethylene glycol, diethylene glycol and triethylene glycol; (Poly) propylene glycols such as propylene glycol, dipropylene glycol and tripropylene glycol; Dihydric alcohols such as 1,6-hexanediol; And trihydric alcohols such as glycerol and trimethylolpropane.

And epoxy resin, polyamide, polyamideimide, polyurethane, polybutadiene, chloroprene, polyether, polyester, pentadiene derivative, SBS (styrene / butadiene / styrene block copolymer), hydrogenated SBS, SIS (styrene / isoprene Styrene block copolymers), petroleum resins, xylene resins, ketone resins, fluorine-containing oligomers, silicon-type oligomers, polysulfide-type oligomers and the like can be added as other additives to the compositions of the present invention.

In addition, paint additives such as antioxidants, UV absorbers, light stabilizers, anti-aging agents, anti-foaming agents, leveling agents, antistatic agents, surfactants, preservatives, thermal polymerization inhibitors, plasticizers and wetting enhancers may be added to the compositions of the present invention. have. Examples of antioxidants include Irganox 245, 259, 565, 1010, 1035, 1076, 1081, 1098, 1222 and 1330 (manufactured by Ciba Specialty Chemicals Co., Ltd.).

Examples of UV absorbers are benzotriol-type and triazine-type UV absorbers. Examples of commercially available products of the UV absorbers include Tinuvin P, 234, 320, 326, 327, 328, 213, 400 (manufactured by Ciba Specialty Chemicals Co., Ltd.), Sumisorb 110, 130, 140, 220, 250 , 300, 320, 340, 350 and 400 (manufactured by Sumitomo Chemical Industries Co., Ltd.).

Examples of light stabilizers include Tinuvin 144, 292, 622LD (manufactured by Ciba Specialty Chemicals Co., Ltd.), Sanol LS440, LS770 (manufactured by Sankyo Co., Ltd.), and Sumisorb TM-061 (Sumitomo Chemical Industries Co., Ltd.). There is a problem.

Examples of anti-aging agents include phenol-type anti-aging agents, allylamine-type anti-aging agents, and ketone amine-type anti-aging agents. Examples of commercially available products of the anti-aging agents include Antigene W, S, P, 3C, 6C, RD-G, FR and AW (manufactured by Sumitomo Chemical Industries Co., Ltd.).

Examples of antifoaming agents include organic copolymers containing no silicon or fluorine atoms, such as Flowlen AC-202, AC-300, AC-303, AC-326F, AC-900, AC-1190 and AC-2000 (Kyoeisha Chemical). Co., Ltd.), silicon atom-containing antifoaming agents, for example, Flowlen AC-901, AC-950, AC-1140, AO-3, AO-4OH (manufactured by Kyoeisha Chemical Co., Ltd.), FS1265, SH200, SH5500, SC5540, SC5570, F-1, SD5590 (manufactured by Toray-Dow Corning Silicone Co., Ltd.) and fluorine atom-containing antifoaming agents such as MEGAFAC F-142D, F-144D, F-178K, F-179, F -815 (manufactured by Dainippon Ink and Chemicals, Inc.).

Examples of leveling agents include PolyFlow No. 7, No. 38, No. 50E, S, 75, No. 75, No. 77, No. 90, No. 95, No. 300, No. 460, ATF and KL- 245 (manufactured by Kyoeisha Chemical Co., Ltd.). The added amount of the additive may be selectively determined as long as it does not adversely affect the purpose of the composition of the present invention.

The viscosity of the composition of the invention is preferably 10-10,000 mPa · s, more preferably 50-5,000 mPa · s and particularly preferably 150-2,000 mPa · s.

It is preferred to add each component so that the glass transition temperature of the resulting cured product is in the range of -30 ° C to 200 ° C, preferably 0 to 120 ° C. If the glass transition temperature is too low, the cured product softens in hot summers or in closed, sunny rooms, causing the substrate to move or move to reduce adhesion. If the glass transition temperature is too high, the substrate may break when the adhesion is insufficient, or when it is dropped or bent.

The term " glass transition temperature " as used herein refers to a temperature that represents the maximum value of loss tangent (tan δ) measured using dynamic viscoelasticity measurements at an oscillation frequency of 10.

It is preferable that the composition of the present invention is cured by irradiating the composition with ultraviolet rays, visible rays, electron beams, or the like. For example, the composition of the present invention applied between substrates so that the adhesive layer thickness is 10-100 μm is easily cured by irradiating the composition using a metal halogen lamp in an amount of 50-2000 mJ / cm 2 to adhere the substrate.

The photocured product of the composition of the present invention preferably has excellent transparency. For example, a 60 μm thick layer of cured product has 90% or more light transmission at 600-700 nm. If the light transmittance is less than 90%, the appearance of the optical disc may be damaged. Then, light for decrypting the information stored in the disk can be reduced by the adhesive layer of the cured product, whereby the decryption operation is interrupted. Therefore, it is preferable to prepare the composition of the present invention by combining the components so that the light transmittance of the cured product is within the above range.

It is preferable to add each component so that the photocuring product of the composition of this invention may have a refractive index of 1.51-1.70 at 25 degreeC. If the refractive index of the photocurable product is outside the above range, problems may arise when decrypting the information stored on the disc.

The composition of the present invention is well suited for various materials including plastics, metals (eg gold, silver and aluminum) and inorganic compounds (eg glass) such as polycarbonate (PC) and polymethylmethacrylate (PMMA). Adhesiveness is shown. Therefore, the composition of the present invention is suitable as an adhesive for optical discs.

The invention will be illustrated by this embodiment, which should not be considered as limiting the invention.

Synthesis of Urethane Acrylate (Component (A)):

Synthesis Example 1

A separate 1 L flask equipped with a stirrer and thermometer was charged with 209 g of isophorone diisocyanate, 0.2 g of 3,5-di-t-butyl-4-hydroxytoluene and 0.8 g of di-n-butyltin dilaurate. The mixture was stirred and cooled to 10 ° C. in a cold water bath in dry air. 109 g of 2-hydroxyethyl acrylate was added slowly at 10-35 ° C. for 1 hour and allowed to react. After adding 305.5 g of polytetramethylene glycol ("PTMG 650" manufactured by Mitsubishi Chemical Corp.) having an average molecular weight of 650, the mixture was reacted at 40-60 ° C for 5 hours with stirring. The reaction product was removed to obtain urethane acrylate (A1) having a number average molecular weight of 1300.

Synthesis Example 2

The number average molecular weight was 1650 in the same manner as in Synthesis Example 1, except that 480 g of polytetramethylene glycol ("PTMG 1000" manufactured by Mitsubishi Chemical Corp.) was used instead of the polytetramethylene glycol used in Synthesis Example 1. Urethane acrylate (A2) was obtained.

Example 1

40 g of urethane acrylate (A1) synthesized in Synthesis Example 1, 20 g of 4-hydroxybutyl acrylate (C1) ("4HBA" manufactured by Osaka Organic Chemical Industry Co., Ltd.) in a reaction vessel equipped with a stirrer, ethylene jade 15 g of seed addition bisphenol A diacrylate (F1) ("VR77" manufactured by Showa Highpolymer Co., Ltd.), 25 g of ethylene glycol diacrylate (F2) ("Light Acrylate 4EGA" manufactured by Kyoeisha Chemical Co., Ltd.), 3 g of 2,2-dimethoxy-1,2-diphenylethan-1-one ("Irgacure 651" manufactured by Ciba Specialty Chemicals Co., Ltd.), 2-hydroxy-2-methyl-1-phenylpropane-1 -One ("Darocur 1173" manufactured by Ciba Specialty Chemicals Co., Ltd.) 3 g, ethyl dimethylaminobenzoate ("KAYACURE EPA" manufactured by Nippon Kayaku Co., Ltd.) 0.5 g, gamma -mercaptopropyltrimethoxysilane ("SH6062" from Toray-Dow Corning Silicone Co., Ltd.) 1 g and 2,2-thiodiethylene bis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] 0.3 g ("Irganox 1035" manufactured by Ciba Specialty Chemicals Co., Ltd.) were charged. The mixture was stirred at 50 ° C. for 1 hour to obtain the composition of Example 1.

Example 2-9

A coating film-forming composition was prepared in Example 2-9 in the same manner as in Example 1 except for changing the components. Each component shown in Table 1 is as follows. The amounts of components in Table 1 are expressed in parts by weight.

Ingredient (B)

B1: ethyl p-dimethylaminobenzoate ("KAYACURE EPA" manufactured by Nippon Kayaku Co., Ltd.)

B2: isoamyl dimethylaminobenzoate ("KAYACURE DMBI" by Nippon Kayaku Co., Ltd.)

Ingredient (C)

C1: 4-hydroxybutyl acrylate ("4-HBA" made by Osaka Organic Chemical Industry Co., Ltd.)

Ingredient (D)

D1: 2,2-dimethoxy-1,2-diphenylethan-1-one ("Irgacure 651" manufactured by Ciba Specialty Chemicals Co., Ltd.)

D2: 2-hydroxy-2-methyl-1-phenyl-propan-1-one ("Darocur 1173" manufactured by Ciba Specialty Chemicals Co., Ltd.)

Ingredient (E)

E1: gamma -mercaptopropyltrimethoxysilane ("SH6062" manufactured by Toray-Dow Corning Silicone Co., Ltd.)

Other ingredients

Ethylene Oxide Addition Bisphenol A Di (meth) acrylate ("VR-77" manufactured by Showa Highpolymer Co., Ltd.)

Ethylene Glycol Diacrylate ("Light Acrylate 4EGA" manufactured by Kyoeisha Chemical Co., Ltd.)

Phenoxyethyl acrylate ("New Frontier PHE" by Daiichi Kogyo Seiyaku Co., Ltd.)

2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propan-1-one ("Irgacure 907" manufactured by Ciba Specialty Chemicals Co., Ltd.)

2,2-thio-diethylene bis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] ("Irganox 1035" by Ciba Specialty Chemicals Co., Ltd.)

The edge curability, moisture-heat resistance, and adhesion to the substrate of the prepared compositions (compositions of Examples 1-9) were measured and evaluated as described below.

(1) corner curability

The composition was applied between the gold substrate and the PC substrate produced by sputtering the PC substrate such that the composition film thickness was 50 μm. The substrates were adhered by irradiating the composition from the gold substrate side or the PC substrate side using a conveyor-type metal halogen lamp in an amount of 500 mJ / cm 2. When adhesiveness (viscosity) was found by placing a finger on the obtained disk edge, the edge curability of the composition was determined to be "bad". When there was no adhesiveness, the edge curability of the composition was determined to be "good". The edge curability of the non-tacky composition after irradiation in an amount of 250 mJ / cm 2 was determined to be “excellent”.

(2) moisture-resistant

The substrates were adhered by irradiating the composition in an amount of 500 mJ / cm 2 in the same manner as in (1). After being placed in a constant temperature and humidity chamber at a temperature of 90 ° C. and a relative humidity of 98% RH, if the abnormal symptoms such as bubbles or corrosion are found at the interface between the substrate and the adhesive or the adhesive layer, the moisture-heat resistance of the composition is determined to be “bad”. It became. If no abnormal symptoms were found, the moisture-heat resistance of the composition was determined to be "good".

(3) adhesion to substrates

The composition was applied to an aluminum film or gold film that was evaporated on a PC substrate using the sputtering method. The composition was irradiated in an amount of 100 mJ / cm 2 under nitrogen atmosphere to obtain a cured film of a composition having a thickness of 50 μm. Thereafter, the cured film was subjected to a cross-cut cellophane tape peeling test. When the aluminum film or the gold film was not removed from the PC substrate, the adhesion of the composition was determined to be "good". When one or more corners were removed, the adhesiveness of the composition was determined to be "bad".

Table 1 shows the result of adhering the aluminum substrate manufactured by sputtering the PC substrate and the PC substrate, and the result of adhering the gold substrate manufactured by sputtering the PC substrate and the PC substrate. The composition of Example 7 without containing component (B) exhibited relatively poor edge curability but good moisture-heat resistance. The compositions of Examples 8 and 9, which did not contain components (C) and (D) in combination, exhibited relatively poor moisture-heat resistance, but showed good edge hardenability. The composition of Example 6, which contained no component (E), exhibited relatively poor adhesion to gold.

Example One 2 3 4 5 6 7 8 9 A1 40 50 50 60 40 40 40 40 A2 40 C1 20 20 20 30 40 20 20 20 Ethylene Oxide Additives Bisphenol A Di (meth) acrylate (parts by weight) 15 15 20 20 15 15 15 15 Ethylene Glycol Diacrylate 25 25 10 25 25 25 25 Phenoxyethyl acrylate 20 B1 0.5 0.5 0.3 One 0.5 0.5 0.5 B2 0.5 D1 3 3 3 5 2 3 3 3 D2 3 3 3 2 4 3 3 3 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propane-1-one 5 E1 One 0.5 One One One One One One 2,2-thio-diethylene bis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Combination of PC Base and Aluminum Base Corner curable Great Good Good Good Good Good Bad Good Good Moisture-Resistant Good Good Good Good Good Good Good Bad Bad Combination of Gold Base and Aluminum Base Corner curable Great Good Good Good Good Good Bad Good Good Moisture-Resistant Good Good Good Good Good Good Good Bad Bad

Claims (21)

(a) radiation-curable oligomers; And (b) dialkylaminobenzoate. The method of claim 1, Wherein the composition comprises 0.05-5 wt% of the dialkylaminobenzoate by the total weight of the composition. The method according to claim 1 or 2, Selected from the group consisting of 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 1-hydroxycyclohexyl phenyl ketone The composition, characterized in that it further comprises a compound. The method according to any one of claims 1 to 3, The composition further comprises hydroxyalkyl (meth) acrylate. The method of claim 4, wherein Wherein the composition comprises 5-70 wt% of the hydroxyalkyl (meth) acrylate by weight of the composition. (a) radiation-curable oligomers; (c) hydroxyalkyl (meth) acrylates; And (d) 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 1-hydroxycyclohexyl phenyl ketone A composition comprising a compound selected from the group consisting of: The method according to any one of claims 1 to 6, Wherein said composition comprises ethyl p-dimethylaminobenzoate. The method according to any one of claims 1 to 7, (e) A composition comprising a thiol compound having a methoxysilyl group. The method of claim 8, The composition is a composition, characterized in that containing 0.1-5wt% of the thiol compound based on the total weight of the composition. The method according to any one of claims 1 to 9, Wherein said radiation-curable oligomer is prepared by reacting a polyol compound, a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate compound. The method of claim 10, The number average molecular weight of the polyol compound is 250 to 800, characterized in that the composition. The method according to any one of claims 1 to 11, Wherein said composition comprises 20-80 wt% of said radiation-curable oligomer by weight of the composition. The method according to any one of claims 1 to 12, Wherein said composition comprises hydroxy C ₁ -C ₆ alkyl (meth) acrylate. The method according to any one of claims 1 to 13, Wherein said composition comprises 4-hydroxybutyl (meth) acrylate. The method according to any one of claims 1 to 14, Wherein said composition comprises 2,2-dimethoxy-1,2-diphenylethan-1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one. The method according to any one of claims 1 to 15, A 60 μm thick layer of the composition is characterized in that it has 90% or more light transmission at 600-700 nm. The method according to any one of claims 1 to 16, Said composition having a viscosity of 150-2,000 mPa · s. Use of the composition according to any one of claims 1 to 17, characterized in that it is used as an adhesive for optical discs. The method of claim 18, And the optical disc is a digital multipurpose disc. An optical disc comprising the adhesive obtained by curing the composition according to any one of claims 1 to 17. The method of claim 20, And the optical disc is a digital multi-purpose disc.