EP0960355A1 - Photocurable resin composition - Google Patents

Photocurable resin composition

Info

Publication number
EP0960355A1
EP0960355A1 EP98905865A EP98905865A EP0960355A1 EP 0960355 A1 EP0960355 A1 EP 0960355A1 EP 98905865 A EP98905865 A EP 98905865A EP 98905865 A EP98905865 A EP 98905865A EP 0960355 A1 EP0960355 A1 EP 0960355A1
Authority
EP
European Patent Office
Prior art keywords
meth
composition
acrylate
urethane
cured
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98905865A
Other languages
German (de)
English (en)
French (fr)
Inventor
Hideaki Takase
Ryoji Furuta
Toshihiko Takahashi
Takashi Ukachi
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
Original Assignee
JSR Corp
Japan Fine Coatings Co Ltd
DSM NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JSR Corp, Japan Fine Coatings Co Ltd, DSM NV filed Critical JSR Corp
Publication of EP0960355A1 publication Critical patent/EP0960355A1/en
Withdrawn legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/256—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers improving adhesion between layers
    • 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
    • C08F290/08—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 side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/147—Polyurethanes; Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/675—Low-molecular-weight compounds
    • C08G18/677—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
    • C08G18/6785—Low-molecular-weight compounds containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups containing phosphorus
    • 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
    • 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
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2531—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising glass
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2532—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising metals
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
    • G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers

Definitions

  • the present invention relates to a photocurable resin composition and, in particular, to a photocurable resin composition useful as an adhesive for the manufacture of optical disks.
  • DVD digital versatile disk
  • a DVD can record a greater amount of information than a CD (compact disk) , even though these disks are almost the same in size.
  • DVDs are mainly manufactured by a so called bonding method, which comprises forming recording layers on at least one plastic disk by depositing metal using a sputtering technique. The disks are then lamented together with an adhesive to form a mult-layer DVD.
  • a hot-melt type or a heat hardening type adhesive have been conventionally used in this method. These adhesives, however, have exhibited problems in the length of time required for manufacturing optical disks. These adhesives not only require a long working time to obtain sufficient adhesion characteristics but also experience decreased adhesion under high temperature-high humidity conditions, because these adhesives are easily softened and melted under such conditions. As a result, DVD disks bonded by conventional adhesives have a tendency to become displaced when the optical disks are preserved under high temperature-high humidity conditions after manufacture, which is unacceptable.
  • ultraviolet radiation (UV) curable type adhesives comprising urethane acrylate as a major component have recently been proposed (for example, Japanese Patent Applications Laid-open No. 142545/1986, No. 89462/1994) . However, these recently proposed adhesives much like the other conventional adhesives provide unsatisfactory photo-curability and adhesive properties .
  • UV adhesives have resulted in corrosion of the metal used in the recording layer because of moisture attack.
  • TAn object of the present invention is to provide a photocurable resin composition possessing superior curability, producing cured products which exhibit excellent adhesive properties under high temperature-high humidity conditions, and which are free from metal corrosion.
  • a specific photocurable resin composition which comprises : (A) an oligomer comprising a polymeric backbone, linked via urethane bonds to (meth) acrylate terminal groups (hereinafter referred to as a urethane (meth) acrylate (A) ) ,
  • the urethane (meth) acrylate of component (A) comprises a polymeric backbone, urethane bonds and (meth) acrylate terminal groups .
  • This oligomer containing an urethane bond preferably is obtained by condensation of (a) at least one polymeric polyol compound selected from a group consisting of polyester polyols and polycarbonate polyols, (b) a polyisocyanate compound, and (c) a hydroxyl group-containing (meth) acrylate compound.
  • the polyol compound constitutes the backbone, which is connected to the (meth) acrylate terminal groups through the urethane groups that, are formed by reaction of the isocyanates with the hydroxyl groups.
  • polyester polyols obtained by the reaction of a polyhydric alcohol, such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1, 4.-butanediol, 1,6- hexanediol, neopentyl glycol, 1,4-cyclohexane- dimethanol, 3-methyl-l, 5-pentanediol, 1, 9-nonanediol, 2-methyl-l, 8-octanediol, or trimethylolpropane, and a dibasic acid, such as phthalic acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid, or sebasic acid; and polyester polyols obtained by reaction of e -caprolactone, ⁇ -methyl- ⁇ -valerolact
  • polyester polyols may be used either individually or in combinations of two or more.
  • Kurapol A-1010, 1510 and 2010, L-1010 and 2010, P-1010, 1510 and 2010, Adeka New Ace YG-108, YG-226, YG-240 and YG-214 are particularly desirable.
  • An example of useful polycarbonate polyols include those represented by the following formula (1) :
  • each R 1 independently represents usually an alkylene group having 2-20, preferably 4-15, carbon atoms, or a residual group (excluding the two hydroxyl groups) from (poly) ethylene glycol, (poly) propylene glycol, or (poly) tetramethylene glycol, wherein the plurality of R ⁇ s may be the same or different.
  • m denotes an integer from 1-30, preferably an integer from 3-20.
  • R 1 residual groups, after exclusion of the two hydroxyl groups, from 1,4-butanediol, 3 -methyl- ⁇ , 5-pentanediol, neopentyl glycol, 1, 6-hexanediol, 1,4- cyclohexanedimethanol, 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, and tetrapropylene glycol.
  • PNOC1000, 2000, Nipporan 982, 983, PLACCEL CD- 205HL, CD-210HL, and CD-220HL are particularly desirable .
  • the average number of hydroxy groups in the polyol generally will be between 1.8 and 4, preferable between about 2 and 3. Most preferably, the number of hydroxy groups of the polyol is about 2.
  • the number average molecular weight of the polyol compounds measured by the terminal group method is usually in the range of 200- 20,000. To ensure adequate hardness and ease of handling of resulting adhesives, a molecular weight in the range of 300-10,000, particularly 400-5,000, is preferred.
  • polyisocyanate compounds examples include diisocyanate compounds such as 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, 1,5- naphthalene diisocyanate, m-phenylene diisocyanate, p- phenylene diisocyanate, 3 , 3 ' -dimethyl-4, 4 ' - diphenylmethane diisocyanate, 4 " , 4' -diphenylmethane diisocyanate, 3 , 3 ' -dimethyl phenylene diisocyanate, 4,4 ' -biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, methylenebis (4-cyclo
  • Lysine triisocyanate is given as an example of (useful) triisocyanate compound.
  • useful polyisocyanate compounds 2,4-tolylene diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, and norbornane diisocyanate methyl are particularly desirable in view of reactivity of isocyanate groups, selectivity, and the characteristics of the resulting oligomers.
  • These polyisocyanate compounds may be used either individually or in combinations of two or more.
  • the proportion of polyisocyanate compound used should be such that the isocyanate group contained in the polyisocyanate compound is usually 1-4 equivalents, preferably 1.1-3 equivalents, for one equivalent of the hydroxyl group contained in the above-mentioned polyol compound.
  • hydroxyl group- containing (meth) acrylate compounds are 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-hydroxy alkyl (meth) acryloyl phosphates (here, alkyl is methyl, ethyl, or propyl, for example), 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, dipentaeryth
  • CH 2 C - C-0-CH 2 CH 2 - (0- C- CH 2 CH 2 CH 2 CH 2 ) L -OH ( 2 ) R 2 0 0
  • R 2 is a hydrogen atom or methyl group and L is an integer usually from 1-15, and preferably 1-4; and addition reaction products obtained from a glycidyl group-containing compound, such as alkyl glycidyl ether, allyl glycidyl ether, or glycidyl (meth) acrylate, and a (meth) acrylic acid.
  • a glycidyl group-containing compound such as alkyl glycidyl ether, allyl glycidyl ether, or glycidyl (meth) acrylate, and a (meth) acrylic acid.
  • a glycidyl group-containing compound such as alkyl glycidyl ether, allyl glycidyl ether, or glycidyl (meth) acrylate, and a (meth) acrylic acid.
  • the amount of the hydroxyl group-containing (meth) acrylate compound used is such that the hydroxyl groups in the hydroxyl group-containing (meth) acrylate compound is usually 0.1-2 equivalents, preferably 0.1- 1.5 equivalents, for one equivalent of the hydroxyl groups contained in the above polyol compound.
  • reaction temperature in these reactions is usually 10-90°C, and preferably 30-80°C.
  • the reactions (I) -(III) are preferably carried out in the presence of a urethanization catalyst, such as copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyl tin- dilaurate, triethylamine, 1,4-diaza-bicyclo [2.2.2] octane, or 1, 4-diaza-2-methylbicyclo [2.2.2] octane.
  • a urethanization catalyst such as copper naphthenate, cobalt naphthenate, zinc naphthenate, di-n-butyl tin- dilaurate, triethylamine, 1,4-diaza-bicyclo [2.2.2] octane, or 1, 4-diaza-2-methylbicyclo [2.2.2] octane.
  • the catalysts are employed in an amount of 0.01-1 part by weight for 100 parts by weight of the total reactant .
  • the average functionality of the urethane (meth) acrylate (A) preferably is between about 1.8 and 8, more preferably lower than 4, and particularly preferred, about 2.
  • the urethane (meth) acrylate (A) typically has a number average molecular weight of 200-30,000. It has been found that urethane (meth) acrylates (A) having a number average molecular weight in the range of 400- 20,000, particularly in the range of 600-10,000, provides photocurable resin compositions that are easier to handle and result in cured compositions having higher mechanical characteristics.
  • the amount of the component (A) to be incorporated into the resin composition is usually 1-94 wt%, and preferably 5-80 wt%, of the total amount of the resin composition. To ensure superior adhesive properties, an amount of 10-70 wt% is particularly preferred. If the amount of the component (A) is too small, adequate adhesive properties cannot be obtained in the substrates; if too large, on the other hand, the viscosity of the composition is increased so that it becomes difficult for the resin composition to be processed with ease.
  • the (meth) acryloyl phosphates employed as component (B) are phosphates possessing at least one, preferably one to three, (meth) acryloyl groups in one molecule.
  • the compounds represented by the following general formula (3) can be given as examples of the (meth) acryloyl phosphate (B) .
  • Y is a monovalent organic group.
  • Y if present, represents an organic group with a molecular weight of about 1000 or less, preferably about 500 or less.
  • the group Y may independently be alkyl, aryl and may comprise ether, amine, hydroxyl, urethane and ethylenically unsaturated groups.
  • Suitable examples of group Y are a group which possesses (1) at least one urethane bond (-NHC00-) and a te ⁇ t ⁇ inal (meth) acryloyl group, (2) a group represented by the formula, -0C a H 2a+1 , wherein a is an integer usually from 0-10, preferably 0-5, or (3) a group represented by the formula, -OC 6 H s , provided a plurality of Ys may be the same or different, "n” is an integer from 1-10, preferably 1-5. "q” is an integer from 1-10, preferably 1-5. And “r” is an integer from 1-3, preferably 2-3.
  • a preferred example of Y includes groups represented by the following formula (4) :
  • n, q, and R 2 have the same meanings as defined above and A denotes a residual group excluding two -NCO groups from a diisocyanate compound.
  • B the (meth) acryloyl phosphate
  • B include mono [2- (meth) acryloyloxyethyl] - phosphate, di [2- (meth) acryloyloxyethyl] phosphate, diphenyl-2-methacryloyloxyethyl phosphate, mono [2- (meth) acryloyloxypolypropyloxy] phosphate , di [2 - (meth) acryloyloxypolypropyoxy] phosphate , tris (acryloyloxyethyl) phosphate, and the compounds represented by the above formula 3 wherein Y is represented by formula (4) , wherein A is the residual group of toluene diisocyanate or isophorone diisocyanate, and wherein
  • (meth) acryloyl phosphates (B) may be used either individually or in combinations of two or more.
  • the (meth) acryloyl phosphate (B) including the monovalent organic group represented by formula (4) may be prepared, for example, by condensing compound of the general formula (3) (which contains at least one -OH group bonded to a phosphorus atom, hereinafter referred to as " (meth) acryloyl acidic phosphate"), a diisocyanate compound, and a hydroxyl group-containing (meth) acrylate compound.
  • component (A) preferably 2,4- tolylene diisocyanate and isophorone diisocyanate, are given as the diisocyanate compound.
  • the amount of the diisocyanate compound used is such that the amount of isocyanate groups contained in the diisocyanate compound is usually 1-4, preferably 1.1-3, equivalents for one equivalent of the OH group bonded to phosphorus atom in the (meth) acryloyl acidic phosphate .
  • the amount of the hydroxyl group-containing (meth) acrylate compound used is usually 0.1-3, preferably 0.5-2, equivalents for one equivalent of the OH group bonded to the phosphorus atom in the (meth) acryloyl acidic phosphate.
  • an amine-type urethanization catalyst such as triethylamine, 1, 4-diazabicyclo [2.2.2] octane, or l,4-diaza-2-methylbicyclo [2.2.2] octane, can preferably be used in an amount of 0.01-1 parts by weight for 100 parts by weight of the total reaction components.
  • the reaction temperature is usually 10-90°C, and preferably 30-80°C.
  • examples of commercially available products which can be used as the component (B) are Light Ester P-M, and P-2M (manufactured by Kyoeisha Chemical Co., Ltd.), Viscoat 3PA (manufactured by Osaka Organic Chemical Industry, Ltd.), EB-169, EB-170, EB-3603, and R-DX63182
  • the (meth) acryloyl phosphate (B) has a molecular weight of 150-2000, more preferably 200-1500.
  • the (meth) acryloyl phosphate (B) has, before mixing this compound with the other constituents of the adhesive composition, a low amount of free acid groups.
  • the acid number of compound (B) is lower than 50, more preferably lower than 25 and most preferred lower than 10.
  • the acid number represent the number of KOH mg required neutralize 100 g of the (meth) acryloylphosphate (B) .
  • a (meth) acryloyl phosphate (B) having a higher acid number than required can be reacted with isocyanate compounds, epoxy compounds and the like to have the amount of phosphoric acid groups reduced. It is also possible to simply esterify the acid groups.
  • Suitable reactants for reaction with the acidic phosphate include mono-isocyanates, acrylate group comprising isocyanate compounds, glycidyl acrylate, bisphenyldiglycidyl ether, propene-oxide, cyclohexene- oxide, derivatives therefrom and the like.
  • the amount of (meth) acryloyl phosphate (B) present in the resin composition should be sufficient to provide adequate adhesive properties, particularly adhesion properties with metal but not excessive so as to cause the cured product to experience increased water absorption and/or exhibit decreased adhesive properties under high temperature - high humidity conditions .
  • (B) incorporated in the resin composition of the present invention is usually 0.1-30 wt%, preferably 0.1-20 wt%, and particularly preferably 0.5-10 wt%.
  • the component (C) is a polyfunctional (meth) acrylate having a plurality functional groups, and free of urethane and phosphate groups . With this component it is possible e.g. to adjust the viscosity, the cure speed of the photo-curable resin composition, and the hardness of the resulting cured products.
  • polyfunctional (meth) acrylate (C) are 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) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) crylate, hydroxypivalic acid neopentyl glycol diacrylate, trimethylolpropane tri (meth) acrylate,
  • These compounds may be used either individually or in combinations of two or more.
  • Commercially available products can also be used as the component (C) . Examples which can be given include Yupimer UV SA1002 and SA2007 (manufactured by Mitsubishi Chemical Corp.), Viscoat #195, #215, #230, #260, #295, #300, #310, #312, #360, #400 and #700 (manufactured by Osaka Organic Chemical Industry, Ltd.), KAYARAD MANDA, DPHA, NPGDA, R-604, DPCA20,-30,- 60,-120, HX-620, D-310 and D-330 ( manufactured by Yupimer UV SA1002 and SA2007 (manufactured by Mitsubishi Chemical Corp.), Viscoat #195, #215, #230, #260, #295, #300, #310, #312, #360, #400 and #700 (manufactured by Osaka Organic Chemical Industry, Ltd.), KAYARAD MANDA, DPHA, NPGDA, R-604,
  • the molecular weight of the polyfunctional (meth) acrylate (C) is usually 100-3,000, and preferably 200-2,000.
  • Component (C) should be present in the resin composition in an amount sufficient to provide a cured product that is sufficiently hard to avoid gaps and/or displacement between laminated- substrates joined by the cured product. On the other hand, the amount of component (C) present in the composition should not be too high so as to provide a cured product having inadequate adhesive properties.
  • the amount of the component (C) incorporated into the composition of the present invention is usually 5-85 wt%, preferably 10-80 wt%, and particularly preferably 15-70 wt%.
  • Photopolymerization initiators commonly used with conventional photocurable resin compositions can be used as component (D) in the present invention without specific restrictions.
  • Such commonly used photo-initiators include 1-hydroxycyclohexyl phenyl ketone, 2, 2-dimethoxy-2-phenylacetophenone, xanthone, fluorenone, benzaldehyde, fluorene, anthraquinone , triphenylamine, carbazole, 3-methylacetophenone, 4- chlorobenzophenone, 4,4' -dimethoxybenzophenone, 4,4'- diaminobenzophenone, Michler's ketone, benzoin propyl ether, benzoin ethyl ether, benzyl methyl ketal, l-(4- isopropylphenyl) -2-hydroxy-2-methylpropan-l-one, 2- hydroxy-2 -methyl-1-phenylpropan-l-one, thioxaneth
  • Lucirin TPO and Lucirin LR8728 manufactured by BASF
  • Irgacure 184, 907 and 369 and CGI-1700 and 1850 manufactured by Ciba-Geigy Ltd.
  • Darocur 1116, 1173 and 4265 manufactured by Merck Co.
  • Ubecryl P36 manufactured by UCB Co.
  • Kayacure ITX, QTX, DETX and BMS manufactured by Nippon Kayaku Co., Ltd.
  • Lucirin TPO, Irgacure 184 and 369, CGI-1850, Kayacure ITX and DETX are especially desirable.
  • the amount of the component (D) used in the composition of the present invention is usually 0.1-15 wt%, preferably 0.5-10 wt%, and particularly preferably 1 - 5 Wt% .
  • various components such as a photopolymerization accelerator, monofunctional (meth) acrylates, vinyl compounds, and various additives can be incorporated into the composition of the present invention as necessary for the particular application.
  • a photopolymerization accelerator such as a photopolymerization accelerator, monofunctional (meth) acrylates, vinyl compounds, and various additives
  • the following compounds are given as examples of photopolymerization accelerators. Triethylamine, diethylamine, N-methyldiethanoleamine, ethanolamine, 4- dimethylaminobenzoate , 4-methyldimethylaminobenzoate , 4-ethyldimethylaminobenzoate, and 4-isoamyldimethyl- amino-benzoate .
  • Ubecryl P102, 103, 104 and 105 are given as commercially available products of these photopolymerization accelerators.
  • KAYACURE DMBI and EPA manufactured by Nippon Kayaku Co., Ltd.
  • the photopolymerization accelerators are added to the composition in an amount usually of 0-10 wt%, and preferably 0-5 wt%.
  • the monofunctional acrylates are 2 -hydroxyethyl (meth) acrylate, 2- hydroxypropyl (meth) acrylate, 2 -hydroxy butyl (meth) acrylate, methyl (meth) acrylate, ethyl
  • R 2 has the same meaning as defined above, R 3 is an alkylene group having 2-6 carbon atoms, R 4 is an alkyl or aryl group having 1-25 carbon atoms, and is preferably a phenyl group, optionally substituted with an alkyl group having 1-12 carbon atoms, and b is an integer from 0-12;
  • R 2 has the same meaning defined above, R 5 is an alkylene group having 2-8 carbon atoms, THF is a tetrahydrofuryl group and d is an integer from 0 - 8 ; and
  • CH 2 CR 2 - CO- ( -0R 5 C0 ) e -0-CH 2 -C ( CH 3 ) 2 -CH C (R 6 ) 2 ( 7 ) ⁇ /
  • R 2 and R 5 have the same meanings as defined above, e is an integer from 0-8, and each R 6 independently is a hydrogen atom, an alkyl group having 1-6 carbon atoms, or the group represented by -R 7 -B, wherein R 7 is an alkylene group having 1-6 carbon atoms and B indicates a (meth) acryloyloxy group.
  • R 7 is an alkylene group having 1-6 carbon atoms and B indicates a (meth) acryloyloxy group.
  • N-vinyl caprolactam and N-vinyl pyrrolidone are given as examples of a preferred vinyl compound.
  • silane coupling agents antioxidants, UV absorbers, light stabilizers, aging preventives, polymerization inhibitors, preservatives, plasticizers, and the like are given.
  • silane coupling agents are N- (2-aminoethyl) -3-aminopropylmethyl- dimethoxysilane, N- (2-aminoethyl) -3-aminopropyl- methylmethoxysilane, N- (2-amino ethyl) -3-amino- propyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyl- 5 trimethoxysilane, 3-aminopropyltriethoxysilane, 3- glycidoxypropyltrimethoxysilane , 3-glycidoxypropyl- methyldimethoxysilane, 2- (3 ,4-epoxycyclohexyl) - ethyltrimethoxy-silane , 3 -chloropropylmethyl- dimethoxysilane, 3-chloropropyl- trimethoxysilane, 3-
  • SH6040, SH6062, SH6076 and SZ6083 manufactured by Toray-Dow Corning Silicone Co.
  • KBM403, KBM503, KBM603, KBM602, KBM803 and KBE903 manufactured by Shin-Etsu Silicone Co., Ltd.
  • antioxidants phenol-based antioxidants
  • UV absorbers benzotriazole-type UV absorbers
  • UV absorbers and the like can be given.
  • Tinuvin P, 234, 320, 326, 327, 328 and 213 manufactured by Ciba-Geigy Ltd.
  • Sumisorb 110, 130, 140, 220, 250, 300, 320, 340, 350 and 400 manufactured by Sumitomo Chemical
  • hindered amine-type light stabilizers are given.
  • Tinuvin 292, 144, 35 622LD manufactured by Ciba Geigy
  • Sanol LS-700, 765, 292, 2626, 1114 and 744 manufactured by Sankyo Co., Ltd.
  • aging preventives phenol- based aging preventives, allylamine-based aging preventives, and ketone amine-based aging preventives are given.
  • Commercially available products of aging preventives include /Antigen W, S, P, 3C, 6C, RD-G, FR and AW (manufactured by Sumitomo Chemical Industries Co. , Ltd.) .
  • additives may be present in amount provided that the addition of these additives does not adversely affect the objects of the present invention.
  • the composition of the present invention can be prepared by blending the above-described components by a conventional method.
  • the resulting composition may have a viscosity of 20-20,000 mPa.s at 25°C.
  • the various components are blended in proportions such that the glass transition temperature of the resulting cured products is in the range of 10-150°C, and preferably 30-120°C. If the glass transition temperature is too low, the cured products becomes so soft that substrates may be displaced when bonded; if the amount is excessive, on the other hand, sufficient adhesion cannot be obtained and substrates may bend.
  • the glass transition temperature is defined to be the temperature at which the loss tangent (tan ⁇ ) is maximum at a vibration frequency of 10 Hz in a dynamic viscoelasticity measuring instrument.
  • the composition of the present invention can be cured by irradiating with ultraviolet light, visible rays, electron beams, or the like in the same manner as conventional photocurable resin compositions are cured.
  • the composition may be applied to a substrate to make a film with a thickness of about 50 ⁇ m and can be substantially cured by irradiating with ultraviolet light from a metal halide lamp with a dominant wavelength of 365 nm at a suitable dose.
  • a dose of less than 1000 mJ/cm 2 is sufficient, and the dose may be as low as 10 mJ/cm 2 . In practise, a dose of between 50-500 mJ/cm 2 often ' will be used to cure the composition of the present invention.
  • a cured product with a thickness of about 100 ⁇ m should have a trans ittance of 90% or more at a wavelength of 500-600 nm. If the transmittance is less than 90%, not only the external appearance of the disks is impaired, but also there may be problems in reading the recording layer by laser beams. Therefore, when the composition of the present invention is manufactured, the various components should be blended at proportions to provide a transmittance in this range.
  • the proportion of various components should be determined so as to make the refractive index of the cured products 1.50-1.60 at 25°C. If the refractive index is outside this range, errors may occur in reading the recording layer by laser beams .
  • the cured products of the composition of the present invention exhibit high adhesive properties to substrates made of a plastic such as polycarbonate (PC) or polymethyl methacrylate (PMMA) , a metal such as aluminum or gold, and an inorganic compound such as glass, and the like.
  • the adhesion is excellent in a wide temperature range (for example 0-60°C) and is stable under high temperature-high humidity conditions, indicating superior durability of the composition. Even when compositions of the present invention experience water absorption as high as conventional adhesives, the corrosion exhibited by the adjacent metal susbtrate is slight or none.
  • Photocurable resin compositions of the present invention typically provide an adhesion property test value of greater than about 70, preferably 75-100 squares remaining.
  • the photocurable resin composition of the present invention will provide at least about 90, preferably 95-100, squares remaining when tested on a PC substrate; greater than about 70, preferably 80-100, squares remaining when test on an Aluminium sputtered PC substrate; greater than about 70, preferably 75-100, squares remaining when tested on a gold sputtered PC substrate; and/or greater than about 90, preferably 95- 100, squares remaining when tested on quartz substrate.
  • Photocurable resin composition of the present invention typically provide an adhesion property test value of greater than 50, preferably greater than 75, squares remaining when measured under high temperature
  • the photocurable resin compositions of the present invention should provide a light transmittance of less than about 50%, preferably less than 20%, when an aluminium sputtered PC board is exposed to high temperature - high humidity conditions in accordance with the Aluminium corrosion test set forth in the Examples . Accordingly, the composition of the present invention is particularly useful as an adhesive for optical disks requiring high adhesive properties to plastics, metals, inorganic compounds, and the like.
  • This compound is designated as methacryloyl phosphate (B-1) and served as a material to prepare the composition in Example 2.
  • a vessel equipped with a stirrer was charged with 30.-0 g of urethane acrylate (A-l) , 29.0 g of isobornyl acrylate, 15.0 g of phenoxyethyl acrylate, 20.0 g of bisphenol A diepoxy acrylate, 2.0 g of tris (acryloyloxyethyl) phosphate as an acryloyl phosphate, 3.0 g of 1-hydroxycyclohexylphenyl ketone as a photopolymerization initiator, and 1.0 g of 3- mercaptopropyltrimethoxysilane as a silane coupling agent.
  • the mixture was blended at 50-60°C to obtain the composition of the present invention.
  • the viscosity of the composition was 600 mPa.s at 25°C.
  • the composition prepared in (1) above was coated on to a polycarbonate (PC) board, an aluminum sputtered PC board, a gold sputtered PC board, and a quartz substrate to produce a film with a thickness of 50 ⁇ m.
  • the composition were irradiated with ultraviolet light (light source: metal halide lamp) at a dose of 50 mJ/cm 2 in a nitrogen atmosphere to obtain cured test specimens.
  • the cross-cut test according to JIS D0202 was carried out using the cured test specimens, wherein the number of squares of cross-cut cured film left on the board without being peeled off was counted. The results are shown in Table 2. The total number of squares initially existing on the board was 100.
  • the glass transition temperature of the cured films was measured using a compulsory resonance vibration type dynamic viscoelasticity measuring instrument (manufactured by Orientech Co., Ltd.) using the cured test specimens (substrate: quartz glass) prepared in the same manner as in 2.1 above .
  • the temperature at which the loss tangent (tan ⁇ ) is maximum at a vibration frequency of 10 Hz was measured. The results are shown in Table 2.
  • One drop of the composition was placed between two sheets of slide glass with a thickness of 1 mm each to produce a film.
  • the thickness of the cured film was adjusted to 1 mm using a spacer.
  • the composition was irradiated with ultraviolet light at a dose of 50 mJ/cm 2 to obtain a cured test specimen.
  • the transmittance of light with a wavelength of 500 nm or 600 nm of the cured test specimen was measured using the same spectrophotometer as the used in the above experiment. The results are shown in table 2.
  • Example 2 A composition of the present invention was prepared in the same manner as in Example 1, except that 2.0 g of methacryloyl phosphate (B-1) was used instead of 2.0 g of the tris (acryloyloxyethyl) - phosphate. The viscosity of the resulting composition was 600 mPa.s. The composition was evaluated in the same manner as Example 1. The results are shown in Table 2.
  • Example 3
  • a vessel equipped with a stirrer was charged with 30.0 g of urethane acrylate (A-2) , 29.0 g of dicyclopentenyl acrylate, 15.0 g of phenoxyethyl acrylate, 20.0 g of hydroxypivalic acid glycol diacrylate, as the polyfunctional acrylate, 2.0 g of tris (acryloyloxy ethyl) phosphate as an acryloyl phosphate, 3.0 g of 2 , 4, 6-trimethylbenzoyl diphenylphosphine oxide as a photopolymerization initiator, and 1.0 g of 3-methacryloyloxypropyl- trimethoxysilane as a silane coupling agent.
  • the mixture was blended at 50-60°C to obtain a composition of the present invention.
  • the viscosity of the composition was 700 mPa.s.
  • the composition was evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • a composition of the present invention was prepared in the same manner as in Example 3, except that 3.0 g of di (2 -acryloyloxyethyl) phosphate was used instead of 2.0 g of the tris (acryloyloxyethyl) phosphate and the addition of the 3- methacryloyloxypropyl-trimethoxysilane was omitted.
  • the viscosity of the resulting composition was 700 mPa.s.
  • the composition was evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • Example 5 A composition of the present invention was prepared in the same manner as in Example 1, except that the amount of the urethane acrylate (A-l) was changed to 15.0 g and 15.0 g of urethane acrylate (A-2) was added. The viscosity of the resulting composition was 700 mPa.s. The composition was evaluated in the same manner as in Example 1. The results are shown in Table 2. Comparative Example 1
  • a vessel equipped with a stirrer was charged with 34.0 g of isobornyl acrylate, 20.0 g of phenoxyethyl acrylate, 40.0 g of bisphenol A diepoxy acrylate, 2.0 g of trisacryloyloxyethyl phosphate as an acryloyl group-containing phosphate, 3.0 g of l- hydroxycyclohexylphenyl ketone as a photopolymerization initiator, and 1.0 g of 3- mercaptopropyltrimethoxysilane as a silane coupling agent.
  • the mixture was blended at 50-60°C to obtain a composition of the present invention.
  • the viscosity of the composition was 800 mPa.s.
  • the composition was evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • a composition of the present invention was prepared in the same manner as in Example 1, except that the addition of trisacryloyloxyethyl phosphate was omitted and the amount of the bisphenol A diepoxy acrylate was changed from 20.0 g to 22.0 g.
  • the viscosity of the resulting composition was 650 mPa.s.
  • the composition was evaluated in the same manner as in Example 1. The results are shown in Table 2.
  • Substrate Aluminum sputtered PC substrate
  • Substrate Aluminum sputtered PC substrate
  • the photocurable resin composition of the present invention exhibits a faster cure speed than any conventional resin compositions on exposure to radiation such as ultraviolet light, visible light, and electron beams.
  • the cured product exhibits high adhesion to plastic substrates such as polycarbonate, metals such as aluminum or gold, or inorganic compounds such as glass.
  • the adhesion of the cured product is excellent in a wide temperature range and stable even under high temperature-high humidity conditions.
  • the cured product exhibits water absorption of the same level as conventional products, the resulting amount of corrosion of sputtered metal is slight or none.
  • the resin composition therefore is useful as an adhesive for optical disks, for example, particularly as an adhesive for manufacturing bonding- type optical disks such as digital-versatile-disks, in which high adhesion to plastics, metals, inorganic compounds, and the like is required.

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* Cited by examiner, † Cited by third party
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See references of WO9836325A1 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103525356A (zh) * 2013-10-23 2014-01-22 南宁珀源化工有限公司 一种蓝宝石切割用固定胶
CN103555252A (zh) * 2013-10-23 2014-02-05 南宁珀源化工有限公司 一种陶瓷玻璃切割用固定胶
CN103525356B (zh) * 2013-10-23 2015-04-15 南宁珀源化工有限公司 一种蓝宝石切割用固定胶

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WO1998036325A1 (en) 1998-08-20
KR20000070986A (ko) 2000-11-25
CN1252136A (zh) 2000-05-03
KR100539141B1 (ko) 2005-12-26

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