WO2013152251A1 - Radiation-cured adhesive composition and laminate using the same - Google Patents
Radiation-cured adhesive composition and laminate using the same Download PDFInfo
- Publication number
- WO2013152251A1 WO2013152251A1 PCT/US2013/035357 US2013035357W WO2013152251A1 WO 2013152251 A1 WO2013152251 A1 WO 2013152251A1 US 2013035357 W US2013035357 W US 2013035357W WO 2013152251 A1 WO2013152251 A1 WO 2013152251A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- radiation
- adhesive composition
- cured adhesive
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 126
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 126
- 239000000203 mixture Substances 0.000 title claims abstract description 104
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 87
- 239000000178 monomer Substances 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 14
- 238000007650 screen-printing Methods 0.000 claims abstract description 13
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 53
- -1 alkylene glycol Chemical compound 0.000 claims description 47
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 229910001220 stainless steel Inorganic materials 0.000 claims description 8
- 239000010935 stainless steel Substances 0.000 claims description 8
- 239000013008 thixotropic agent Substances 0.000 claims description 8
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000003607 modifier Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000001723 curing Methods 0.000 description 24
- 239000011347 resin Substances 0.000 description 22
- 229920005989 resin Polymers 0.000 description 22
- 239000000126 substance Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 9
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 9
- 229920006267 polyester film Polymers 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 229920002799 BoPET Polymers 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- ROPDSOYFYJCSTC-UHFFFAOYSA-N 2-phenoxyundecyl prop-2-enoate Chemical group CCCCCCCCCC(COC(=O)C=C)OC1=CC=CC=C1 ROPDSOYFYJCSTC-UHFFFAOYSA-N 0.000 description 2
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical class C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 description 1
- ZODNDDPVCIAZIQ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C=C ZODNDDPVCIAZIQ-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- VLGJYRWXOBYNOW-UHFFFAOYSA-N 1-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-2-phenoxyundecan-2-ol;prop-2-enoic acid Chemical group OC(=O)C=C.OCCOCCOCCOCC(O)(CCCCCCCCC)OC1=CC=CC=C1 VLGJYRWXOBYNOW-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- YCPMSWJCWKUXRH-UHFFFAOYSA-N 2-[4-[9-[4-(2-prop-2-enoyloxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethyl prop-2-enoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C1(C=2C=CC(OCCOC(=O)C=C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YCPMSWJCWKUXRH-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- LRRQSCPPOIUNGX-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(O)C(=O)C1=CC=C(OC)C=C1 LRRQSCPPOIUNGX-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- MGSBHCXXTFPYAJ-UHFFFAOYSA-N 2-phenoxyethyl 2-methylidenebutaneperoxoate Chemical compound CCC(=C)C(=O)OOCCOC1=CC=CC=C1 MGSBHCXXTFPYAJ-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- BQUNPXRABCSKJZ-UHFFFAOYSA-N 2-propan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3C(=O)C2=C1 BQUNPXRABCSKJZ-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical class CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 description 1
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DMKSVUSAATWOCU-HROMYWEYSA-N loteprednol etabonate Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)OCCl)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O DMKSVUSAATWOCU-HROMYWEYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
Definitions
- the present invention relates to a radiation-cured adhesive composition and a laminate using the same.
- compositions that exhibit curability when irradiated with ultraviolet or other radiation.
- Adhesive tapes, adhesive sheets, and the like are formed by applying such compositions onto substrates in a state not yet being cured by radiation and then irradiating with radiation.
- Examples of compositions used in such a field include those disclosed in Japanese Unexamined Patent
- adhesive compositions for example, solvent-based adhesives or water- based adhesives
- a fine pattern is not easy to apply because the contained adhesive is a polymer and is also adhesive. Accordingly, in the case when an adhesive layer having a specific shape is to be formed on a substrate, the common practice is to punch out and process the adhesive film.
- composition which becomes an adhesive by irradiation with radiation, is definitely superior, because a problem of production of volatile materials (organic solvents, and the like) during adhesion processing is less likely to occur compared with solvent-based adhesives, and the amount of heat, and the like, used for processing is reduced compared with water-based adhesives (emulsion- based, and the like), in which the water, having large specific heat capacity, must be volatilized.
- a radiation-cured adhesive composition can be obtained, containing from 10 to 70 wt.% of an ethylenically unsaturated monomer not containing an aromatic ring, from 1 to 10 wt.% of a photopolymerization initiator, and from 10 to 55 wt.% of a crosslinking agent; the radiation-cured adhesive composition containing from 10 to 45 wt.% of an alkyl (meth)acrylate having from 8 to 18 carbon atoms in the alkyl group as the ethylenically unsaturated monomer not containing an aromatic ring, and containing from 10 to 50 wt.% of a urethane poly(meth)acrylate having a weight average molecular weight of from 20,000 to 100,000 as the crosslinking agent.
- the radiation-cured adhesive composition of the present invention exhibits excellent adhesiveness on a wide range of adherends including stainless steel, ABS, and the like because specific components are combined in prescribed quantities. Shape processing furthermore is easy even with fine shapes because stringiness is not likely to be produced during application on an adherend by screen- printing. Also, the composition can be leveled easily after application, and therefore, for example, the adhesive layer is not likely to be formed in a swollen condition, and a desired fine shape can be obtained assuredly. Also, even if air is briefly taken in, there is a tendency for the bubbles to clear naturally, and therefore the formation of cavities in the adhesive layer and the production of roughness on the surface is prevented.
- FIG. 1 A is a perspective view illustrating a radiation-cured adhesive composition in an uncured state that is laid on a mesh, with a squeegee and a scraper having been arranged thereon;
- FIG. IB is a perspective view illustrating the radiation-cured adhesive composition being spread by the scraper on the mesh and an adherend being brought into proximity with the bottom face of the mesh;
- FIG. 1 C is a perspective view illustrating the radiation-cured adhesive composition being printed on the adherend by the squeegee;
- FIG. ID is a perspective view illustrating the state on completion of the printing
- FIG. IE is a perspective view illustrating the radiation-cured adhesive composition having been transferred onto the adherend.
- FIG. IF is a perspective view illustrating the adhesive having a desired shape as formed on the adherend 20.
- FIG. 2A is a perspective view of the end portion of an adhesive having been drawn out from a roll-form adhesive film; and FIG. 2B is a perspective view illustrating the appearance when cut by a die cutter.
- the presently disclosed radiation-cured adhesive composition contains an ethylenically unsaturated monomer not containing an aromatic ring, a polymerization inhibitor, and a crosslinking agent as necessary components, and contains an alkyl (meth)acrylate having from 8 to 18 carbon atoms in the alkyl group as the ethylenically unsaturated monomer not containing an aromatic ring, and a urethane poly(meth)acrylate having a weight average molecular weight of 20,000 to 100,000 as the crosslinking agent.
- (meth)acrylate signifies acrylate or methacrylate, and the same applies in other cases as well.
- component A ethylenically unsaturated monomer not containing an aromatic ring
- component A signifies an ethylenically unsaturated monomer in which a benzene ring, naphthalene ring, or other aromatic ring is not present in the molecule, and the ethylenically unsaturated bond contains a substituted or non-substituted vinyl bond.
- a content of component A is from 10 to 70 wt.% based on a total weight of the radiation-cured adhesive composition, and from 10 to 45 wt.% of an alkyl
- component Al (meth)acrylate having from 8 to 18 carbon atoms in the alkyl group (hereinafter referred to as "component Al "), based on the total weight of the radiation-cured adhesive composition, must be contained as component A.
- Component A 1 contributes mainly to adhesiveness after curing. Note that the number of ethylenically unsaturated groups in component A is ideally one per molecule.
- component A is preferably from 20 to 70 wt.%, and more preferably from 30 to 60 wt.%.
- component Al is preferably from 10 to 45 wt.%, and more preferably from 20 to 40 wt.%.
- the excellence of the adhesiveness is further increased by containing component A 1 to such extent.
- the number of carbon atoms in the alkyl group of component Al is preferably from 8 to 16, and more preferably from 8 to 12. This alkyl group may contain branches. 8 or more carbon atoms are preferable from the viewpoint of odor.
- component Al examples include n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth) acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, myristyl (meth)acrylate, hexyldecyl (meth)acrylate, hexadecyl (meth)acrylate, octadecyl (meth)acrylate, isostearyl (meth)acrylate, and octyldecyl (meth)acrylate.
- 2-ethylhexyl acrylate and lauryl acrylate are particularly preferable as component Al .
- At least one kind of monomer selected from a group including an alkyl (meth)acrylate other than those having 8 to 18 carbon atoms in the alkyl group (hereinafter referred to as “component A2”), an alkoxyalkyl (meth)acrylate (hereinafter referred to as “component A3”), a (meth)acrylate containing a carboxylic acid (hereinafter referred to as “component A4"), and an ethylenically unsaturated monomer containing an amide group (hereinafter referred to as “component A5") may be contained as component A.
- component A2 examples include butyl (meth)acrylate, hexyl (meth)acrylate, and other alkyl (meth)acrylates having 4 to 6 carbon atoms in the alkyl group, behenyl (meth)acrylate and other alkyl (meth)acrylates having 20 to 22 carbon atoms in the alkyl group, and cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and other alicyclic (meth)acrylates.
- component A3 examples include polyalkylene glycol mono(meth)acrylate and polyalkylene glycol monoalkyl ether (meth)acrylate.
- component A4 include (meth)acrylic acid, acrylate dimers, omega-carboxy-polycaprolactone mono(meth)acrylate, and 2- (meth)acryloyloxyethyl phthalate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-
- component A4 are omega-carboxy-polycaprolactone
- the adhesive strength can be markedly improved on adherends of stainless steel, other metals, plastic, or the like, by adding these components.
- Monomers containing amide groups are ideal as component A5.
- the cohesive force of the adhesive is improved by adding these components, and the effect of improving the adhesive strength on adherends of stainless steel, other metals, glass, or the like, is great particularly in the case when combined with the abovementioned acid-group-containing monomers.
- At least one kind of monomer selected from a group including (meth)acrylamide, N-substituted (meth)acrylamide, N,N-substituted (meth)acrylamide, aminoalkyl (meth)acrylamide, N-substituted aminoalkyl (meth)acrylamide, and N,N- substituted aminoalkyl (meth)acrylamides is preferable as component A5.
- N- methylol (meth)acrylamide N-methoxymethyl N-methylol (meth)acrylamide, N-ethoxymethyl N- methylol (meth)acrylamide, N-n-butoxymethyl N-methylol (meth)acrylamide, N-iso-butoxymethyl N- methylol (meth)acrylamide, ⁇ , ⁇ -dimethyl N-methylol (meth)acrylamide, ⁇ , ⁇ -diethyl N-methylol (meth)acrylamide, N-t-butyl N-methylol (meth)acrylamide, N-isopropyl N-methylol (meth)acrylamide, N-t-octyl N-methylol (meth)acrylamide, ⁇ , ⁇ -dimethylaminoethyl N-methylol (meth)acrylamide, N,N- dimethylaminopropyl N-methylol (meth)acrylamide, diacetone acrylamide, and other substituted
- DMAPMA Dimethylaminopropyl methacrylamide
- the radiation-cured adhesive composition can contain from 10 to 40 wt.% of an ethylenically unsaturated monomer containing an aromatic ring (hereinafter referred to as "B"), based on the total weight of the radiation-cured adhesive composition.
- Component B is an ethylenically unsaturated monomer having a benzene ring, naphthalene ring, or other aromatic ring in the molecule, and contributes mainly to cohesive force to improve adhesive strength.
- the boiling point of component A is preferably less than that of component B (that is, the boiling point of component B is at or above the boiling point of component A).
- a content of component B is preferably from 10 to 40 wt.%, and more preferably from 10 to 30 wt.%, from the fact that the effects above can be improved.
- At least one kind of monomer selected from a group including alkylene glycol mono(alkylaryl) ether mono(meth)acrylate, polyalkylene glycol mono(alkylaryl) ether mono(meth)acrylate, alkylene glycol monoaryl ether mono(meth)acrylate, and polyalkylene glycol monoaryl ether mono(meth)acrylate can be used as component B.
- alkylene glycol mono(alkylaryl) ether mono(meth)acrylate (this signifies a (meth)acrylate ester of a mono(alkylaryl) ether of alkylene glycol, and is referred to also as "oxyalkylene alkylaryl ether (meth)acrylate," "alkylaryl alcohol alkylene oxide-modified (meth)acrylate,” and the like) is ethylene glycol mono(alkylphenyl) ether mono(meth)acrylate, and the number of carbon atoms in the alkyl portion of the alkylphenyl group is preferably from 1 to 12, and more preferably from 6 to 12.
- An example of an alkylene glycol mono(alkylaryl) ether mono(meth)acrylate is nonylphenyloxyethylene acrylate (e.g., Aronix Ml 11, Toagosei Co., Ltd.).
- polyalkylene glycol mono(alkylaryl) ether mono(meth)acrylate this signifies a (meth) acrylate ester of a mono(alkylaryl) ether of polyalkylene glycol, and is referred to also as
- polyoxyalkylene alkylaryl ether (meth)acrylate is polyethylene glycol mono(alkylphenyl) ether mono(meth)acrylate, and the number of carbon atoms in the alkyl portion of the alkylphenyl group is preferably from 1 to 12, and more preferably from 6 to 12.
- mono(meth)acrylate is nonylphenoxytetraethylene glycol acrylate (e.g., Aronix Ml 13, Toagosei Co., Ltd.).
- (meth) acrylate ester of a monoaryl ether of alkylene glycol is referred to also as "oxyalkylene aryl ether (meth)acrylate," “aryl alcohol alkylene oxide-modified (meth)acrylate,” and the like) is ethylene glycol monophenyl ether mono(meth)acrylate.
- polyoxyalkylene aryl ether (meth)acrylate is polyethylene glycol monophenyl ether mono(meth)acrylate.
- polyalkylene glycol monoaryl ether mono(meth)acrylates include phenoxyethoxyethyl acrylate (e.g., Aronix M101A, Toagosei Co., Ltd.) and tetraalkylene glycol monophenyl ether monoacrylate (e.g., Aronix Ml 02,
- aryloxyalkyl mono(meth)acrylate is phenoxyethyl acrylate (e.g., Biscoat #192, Osaka Organic Chemical Industry).
- Alkylene glycol mono(alkylaryl) ether mono(meth)acrylate is preferable, and nonylphenyloxyethylene acrylate is particularly preferable, from the fact that the surface energy is lowered.
- a photopolymerization initiator (hereinafter referred to as "component C"), which is a component of the radiation-cured adhesive composition, is a substance that can bring about radical polymerization, cationic polymerization, or the like, on being irradiated with ultraviolet or other radiation, and is used for initiating a reaction with components A and B described above and a crosslinking agent to be described later.
- Component C is contained at from 1 to 10 wt.% based on the total weight of the radiation-cured adhesive composition. The content is preferably from 0.5 to 8 wt.%, and more preferably from 1 to 5 wt.%.
- Component C is preferably a photo-radical initiator, and specific examples include 1 -hydroxy- cyclohexyl-phenylketone, 2-hydroxy-2-methyl- 1 -phenyl- 1 -propanone, 2-hydroxy- 1 - [4-(2- hydroxyethoxy)phenyl] -2-methyl- 1 -propanone, 2-hydroxy- 1 - ⁇ 4- [4-(2-hydroxy-2-methyl-propionyl)- benzyl]phenyl ⁇ -2-methyl-propane-l-one (e.g., Irgacure 127, Ciba Specialty Chemicals), and other alpha- hydroxyketones; methyl benzoylformate and other phenylglyoxylates; alpha,alpha-dimethoxy-alpha- phenylacetophenone (e.g., Irgacure 651, Ciba Specialty Chemicals) and other benzyl dimethyl ketals; 2- benzyl-2
- a phosphorus-containing initiator is preferable from the viewpoint of speed of curing. Particularly in the case when curing in air, the combination of a phosphorus-containing initiator and 2-hydroxy- 1 - ⁇ 4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]phenyl ⁇ -2-methyl-propane- 1 -one is preferable from the perspective of curability.
- a crosslinking agent (hereinafter referred to as "component D"), which is a component of the radiation-cured adhesive composition, is a compound for reacting with components A and B described above to form a crosslinked structure and for adjusting the composition to a suitable viscosity.
- component D A compound having a plurality of ethylenically unsaturated bonds can be used as component D, and a poly(meth)acrylate compound is preferable as that compound.
- the poly(meth)acrylate compound should have from 1.1 to 6 (meth)acryloyl groups, more preferably from 1.1 to 4, and even more preferably from 1.1 to 2.
- a content of component D is from 10 to 55 wt.%, and preferably from 10 to 50 wt.%, based on the total weight of the radiation-cured adhesive composition.
- Component D contains from 10 to 50 wt.% of a urethane poly(meth)acrylate (hereinafter referred to as "component Dl ”) having a weight average molecular weight from 20,000 to 100,000, based on the total weight of the radiation-cured adhesive composition.
- the content of component D 1 is preferably from 20 to 45 wt.%, and more preferably from 20 to 40 wt.%.
- the weight average molecular weight (here, the value calculated by gel permeation chromatography (GPC) based on styrene) is more preferably from 20,000 to 90,000, and even more preferably from 35,000 to 85,000.
- the urethane portion of component D 1 may be a polyester urethane, a polyether urethane, or a polyester-ether urethane.
- the isocyanate forming the urethane may be an aliphatic isocyanate, an alicyclic isocyanate, or an aromatic isocyanate, and the number of isocyanate groups per molecule should be 2).
- Component Dl may also be a mixture of a multifunctional compound and a monofunctional compound. Specifically, a bifunctional compound and a monofunctional compound may be mixed to form, for example, a 1.5-functional compound.
- components D other than component Dl include 2-hydroxy-3-acryloyloxypropyl methacrylate, polyethylene glycol di(meth)acrylate, propoxylated ethoxylated bisphenol A
- component D may also contain only component D 1.
- the radiation-cured adhesive composition can contain an inorganic or organic thixotropic agent (hereinafter referred to as "component E").
- component E an inorganic or organic thixotropic agent
- examples of inorganic thixotropic agents of component E include clay (for example, bentonite) having a particle size of less than 0.1 ⁇ , silica, alumina, titania, zirconia, calcium carbonate, mica, smectite, and surface-treated materials thereof.
- organic thixotropic agents of component E include fatty acids, hydroxy fatty acids, fatty acid amines, fatty acid amides, or other aliphatic amide compounds, hydrogenated castor oil, fatty acid metal soaps, sorbitan fatty acid ester derivatives, sorbit fatty acid ester derivatives, alkylene glycol fatty acid esters, fatty acid glycerin esters, dibenzylidene sorbitol derivatives, modified acrylic polymers and copolymers, polyhydroxycarboxylic acid amines and amides, polyvinyl alcohols, and vinyl polymers (vinyl methyl ether/maleic anhydride).
- a typical content of component E is from 0.1 to 5 wt.% based on the total weight of the radiation-cured adhesive composition.
- micropowder is preferable as component E.
- the radiation-cured adhesive composition preferably further contains a leveling agent (hereinafter referred to as "component F").
- component F a leveling agent
- component F include silicone oligomers, aliphatic oils, acrylic oligomers, polyester oligomers, and liquid synthetic rubber, and BYK-Chemie Japan
- Japan Surfynol series and other commercially available leveling agents can be used.
- An ideal content is from 0.01 to 10 wt.%, and more preferably from 0.05 to 2 wt.%, based on the total weight of the radiation-cured adhesive composition.
- the radiation-cured adhesive composition may further contain a tackifying resin (hereinafter referred to as "component G").
- component G a tackifying resin
- the tackifying agent of component G is not particularly limited provided that the adhesiveness of the adhesive composition of the present invention can be improved, and examples include rosin-based resins, coumarone-indene-based resins, terpene -based resins, C5-based petroleum resins, C9-based petroleum resins, styrene-based copolymers, alkylphenol resins, xylene resins, hydrated and modified resins thereof, and the like.
- favorable results can be obtained, from the viewpoint of compatibility with the adhesive composition, when using hydrated rosin resins, terpene resins, terpene phenol resins, and alkylphenol-modified xylene resins.
- the rosin resins used in the present dislcosure can be commercially available rosins,
- rosins hydrogenated rosins, or derivatives thereof.
- examples include “Tamanol” series rosin-modified phenol resins; “Ester Gum” series, “Pensel” series, and “Super Ester” series rosin ester resins, and “Pinecrystal” rosin derivative (all manufactured by Arakawa Chemical); “Hariphenol” series rosin-modified phenol resins; “Hariester” series and “Neotall” series rosin ester resins (manufactured by Harima Chemicals), and the like.
- the terpene-based resins used in the present invention can be commercially available terpene resins or derivatives thereof.
- Examples include YS resin TO series, TR series, YS Polystar T series, 2000 series, U series, S series, N series, Mighty Ace GG series, and K series (all manufactured by Yasuhara Chemical).
- the xylene resins used in the present invention can be commercially available xylene resins and derivatives thereof. Nikanol (manufactured by Fudow Co., Ltd.), and the like, can be used.
- the softening point of component G is preferably from 60 to 150°C, and more preferably from 80 to 130°C, from the perspective of balance of properties and performance after curing.
- a content of component G is preferably from 10 to 30 wt.%, and more preferably from 10 to 20 wt.%, of the total quantity of the radiation-cured adhesive composition, from the perspective of the balance of properties and performance after curing.
- the radiation-cured adhesive composition described above can be cured in the presence of oxygen or in the presence of an inert gas to be used as an adhesive.
- the curing is preferably done by UVA and/or UVB irradiation, and the intensity is ideally from 100 to 1500 mW/cm 2 .
- an inert gas a gas that is cured in the presence of oxygen.
- the polymerization modifier is preferably included in the radiation-cured adhesive composition, and curing should be done with UV irradiation of an intensity of 20 mW/cm 2 or higher.
- the polymerization modifier is preferably a polymerization modifier by radical reaction, and specific examples include alpha- methylstyrene, alpha-methylstyrene dimers, and compounds having thiol groups. An alpha-methylstyrene dimer is particularly preferable from the perspective of odor.
- the radiation-cured adhesive composition can be obtained by mixing each component described above with the condition that light capable of bringing about a curing reaction is not introduced to the contained curing agent, and all additives that are commonly used in the field can be added in ranges that do not impede the effect of the present invention.
- additives that are commonly used in the field can be added in ranges that do not impede the effect of the present invention.
- antioxidants, photostabilizers, dyes, pigments, fragrances, and the like can be added.
- FIG. 1 is a perspective view typically illustrating states in which an adhesive having a desired shape is formed on a substrate by screen-printing using a radiation-cured adhesive composition.
- FIG. 1A is a perspective view illustrating a radiation-cured adhesive composition 1 in an uncured state that is laid on a mesh including a mesh body 10 for a square frame forming the letters "ab" to be screen printed and a holder 12 for holding the same, with a squeegee 14 having been arranged thereon.
- An adherend 20 is present at a distance from the mesh.
- FIG. IB is a perspective view illustrating the radiation-cured adhesive composition 1 being spread by the squeegee 14 on the mesh and the adherend 20 being brought into proximity with the bottom face of the mesh.
- FIG. 1A is a perspective view illustrating a radiation-cured adhesive composition 1 in an uncured state that is laid on a mesh including a mesh body 10 for a square frame forming the letters "ab" to be screen printed and a holder 12
- FIG. 1 C is a perspective view illustrating the radiation- cured adhesive composition 1 being printed on the adherend 20 by wiping off with the squeegee 14 while pressing the mesh against the adherend 20.
- FIG. ID is a perspective view illustrating the state on completion of the printing; and
- FIG. IE is a perspective view illustrating the adherend 20, which has been removed from the mesh, and with the square frame and the letters "ab" having been transferred onto the adherend 20.
- FIG. IF is a perspective view illustrating the adhesive 2 having a desired shape as formed on the adherend 20 by irradiating the radiation-cured adhesive composition 1 with ultraviolet radiation from a UV irradiation machine 30.
- a laminate having a patterned adhesive composition (radiation-cured adhesive composition 2 after curing) on a substrate (adherend 20) can be obtained thereby.
- the radiation-cured adhesive composition can be shape processed easily because occurrence of stringiness during plate removal in screen-printing (stringiness in the state in FIG. IE) is not likely to occur, and there is no situation in which the adhesive layer is cured in a swollen condition, because the radiation-cured adhesive composition can be leveled easily after application. Additionally, even if air is briefly taken in, bubbles will clear naturally.
- the adhesive after curing exhibits excellent adhesiveness on a wide range of adherends including stainless steel, ABS, or the like.
- FIG. 2 illustrates the formation of an adhesive layer by conventional die cutting.
- FIG. 2A is a perspective view illustrating the end portion of an adhesive 50 having been drawn out from a roll- form adhesive film.
- FIG. 2B is a perspective view illustrating the appearance when cut by a die cutter, and the adhesive divided into adhesive 50a to be affixed to an adherend and adhesive 50b to be discarded.
- FIG. 2C is a perspective view illustrating the adhesive 50a for affixing having been affixed to the adherend 20.
- Embodiment 1 A radiation-cured adhesive composition comprising: from 10 to 70 wt.% of an
- the radiation-cured adhesive composition comprising from 10 to 45 wt.% of an alkyl
- (meth)acrylate having from 8 to 18 carbon atoms in the alkyl group as the ethylenically unsaturated monomer not containing an aromatic ring, and from 10 to 50 wt.% of a urethane poly(meth)acrylate having a weight average molecular weight of 20,000 to 100,000 as the crosslinking agent Embodiment 2.
- Embodiment 3 The radiation-cured adhesive composition according to Embodiment 1 or 2, wherein the ethylenically unsaturated monomer not containing an aromatic ring is a monomer having a boiling point at or above that of the ethylenically unsaturated monomer containing an aromatic ring.
- Embodiment 4 The radiation-cured adhesive composition according to any one of Embodiments 1 to 3, wherein at least one kind of monomer selected from a group including an alkyl (meth)acrylate other than one having from 8 to 18 carbon atoms in the alkyl group, an alkoxyalkyl (meth)acrylate, a (meth)acrylate containing a carboxylic acid, and an ethylenically unsaturated monomer containing an amide group is contained as the ethylenically unsaturated monomer not containing an aromatic ring .
- at least one kind of monomer selected from a group including an alkyl (meth)acrylate other than one having from 8 to 18 carbon atoms in the alkyl group, an alkoxyalkyl (meth)acrylate, a (meth)acrylate containing a carboxylic acid, and an ethylenically unsaturated monomer containing an amide group is contained as the ethylenically unsaturated monomer
- Embodiment 5 The radiation-cured adhesive composition according to any one of Embodiments 1 to 4, wherein the urethane poly(meth)acrylate is a mixture of a urethane di(meth)acrylate and a urethane mono(meth)acrylate, or a urethane di(meth)acrylate, and the weight average molecular weight is from 35,000 to 850,000.
- Embodiment 6 The radiation-cured adhesive composition according to any one of Embodiments 2 to 5, wherein the ethylenically unsaturated monomer containing an aromatic ring is at least one kind selected from a group including alkylene glycol mono(alkylaryl) ether mono(meth)acrylate, polyalkylene glycol mono(alkylaryl) ether mono(meth)acrylate, alkylene glycol monoaryl ether mono(meth)acrylate, polyalkylene glycol monoaryl ether mono(meth)acrylate, and aryloxyalkyl mono(meth)acrylate.
- (meth)acrylamide aminoalkyl (meth)acrylamide, N-substituted aminoalkyl (meth)acrylamide, and N,N- substituted aminoalkyl (meth)acrylamide.
- Embodiment 8 The radiation-cured adhesive composition according to any one of Embodiments 1 to 7, further comprising an inorganic or organic thixotropic agent.
- Embodiment 9 The radiation-cured adhesive composition according to Embodiments 1 to 8, further comprising a leveling agent.
- Embodiment 10 The radiation-cured adhesive composition according to any one of Embodiments 1 to 9, wherein curing is performed by UV irradiation in the presence of oxygen.
- Embodiment 11 The radiation-cured adhesive composition according to any one of Embodiments 1 to 9, further comprising a polymerization modifier, and wherein curing is performed by UV irradiation at a strength of 20 mW/cm 2 or higher in the presence of an inert gas.
- Embodiment 12 The radiation-cured adhesive composition according to any one of Embodiments 1 to 11, wherein a peeling strength on stainless steel and ABS after curing is 4 N/cm or higher.
- Embodiment 13 An adhesive obtained by curing a radiation-cured adhesive according to any one of Embodiments 1 to 12.
- Embodiment 14 A laminate, having a layer containing an adhesive according to Embodiment 13 patterned by screen printing on a substrate.
- compositions having the compositions listed in Table 2 below were mixed in UV-cut plastic bottles.
- the composition was applied by doctor blade to a thickness of 50 ⁇ on a silicone -treated transparent polyester film, and was cured by passing three times through a Fusion FS300 curing oven (H bulb, 15 m/minute, 200 mJ/cm 2 /pass) in an oxygen atmosphere. Sufficient curing was possible thereby. Curing was then further performed seven times in an oxygen atmosphere. The total dosage of irradiation was 2000 mJ/cm 2 .
- the adhesive composition (pressure-sensitive adhesive) on the PET film obtained thereby was laminated with another silicone-treated PET film.
- peeling strength was measured by a method based on JIS Z 0237. The details are as follows.
- the adhesive sheet obtained above was cut by cutter into 25x70 mm pieces. Also, a release film was peeled from the cured surface, and the adhesive sheet was affixed to a polyester film (S-25, Unitika), which had been cut into a 30* 150 mm piece having a thickness of 25 ⁇ .
- a remaining release film was removed from the adhesive sheet, and then the adhesive sheet was affixed using a rubber roller having a weight of 2 kg to an ABS plate (manufactured by Nihon Tact Co., Ltd.) having a thickness of 2 mm, a polypropylene (PP) plate (manufactured by Nihon Tact Co., Ltd.) having a thickness of 2 mm, or a stainless steel plate (manufactured by Nihon Tact Co., Ltd.) having a thickness of 1 mm, which had been immersed in isopropyl alcohol (IPA) and wiped with a cloth.
- IPA isopropyl alcohol
- a release film was peeled from the adhesive sheet obtained above, the adhesive sheet was affixed to a polyester film (S-25, Unitika) having a thickness of 25 ⁇ , and the sheet was cut by cutter into a
- the suitability for screen-printing of the radiation-cured adhesive compositions obtained in the comparative examples was evaluated using a screen printer (SERIA, HK320).
- a screen-printing plate was applied in a pattern on a polyester film (S-100, Unitika Ltd.) having a thickness of 100 ⁇ using a patterned polyester mesh plate (Tetron #120 mesh, 54 ⁇ line width, 55% aperture, Tokai Shoji Co., Ltd.), and the stringiness when removing from the polyester film and the leveling and bubble clearing of the printed object were observed.
- compositions having the compositions listed in Tables 4 and 5 below were created in the same manner as above, and the same kinds of measurements as above were performed. The content (%) of each component and the measurement results are listed in Tables 6 and 7 below.
- compositions having the compositions listed in Table 8 below were created in the same manner as above, the same kinds of measurements as above were performed. The content (%) of each component and the measurement results are listed in Table 9 below.
- compositions having the compositions listed in Table 10 below were created in the same manner as above; the same kinds of measurements as above were performed. The content (%) of each component and the measurement results are listed in Table 11 below.
- AF90/CF10 signifies an adhesive failure of 90% and a cohesive failure of 10%.
- compositions having the compositions listed in Tables 12 and 13 below were mixed in UV-cut plastic bottles. Each composition was applied by doctor blade to a thickness of 50 ⁇ on a silicone -treated transparent polyester film, and was cured in a UV curing oven (365 nm, UV (365) N 2 purge UV irradiation device, Eye Graphics Co., Ltd.). The conditions in the curing oven were 0.5 m/s and 26 mW/cm 2 , and the total dosage of irradiation was lOOO mJ/cm 2 . The curing process was carried out in a nitrogen gas atmosphere (O2 concentration ⁇ 200 ppm). The adhesive composition (pressure-sensitive adhesive) on the PET film obtained thereby was laminated with another silicone-treated PET film.
- a UV curing oven 365 nm, UV (365) N 2 purge UV irradiation device, Eye Graphics Co., Ltd.
- the conditions in the curing oven were 0.5 m/s and 26 mW/cm 2
- compositions having the compositions listed in Table 16 below were mixed in UV- cut plastic bottles. Each composition was applied by doctor blade to a thickness of 50 ⁇ on a silicone-treated transparent polyester film, and was cured in a UV curing oven (365 nm, UV (365) N 2 purge UV irradiation device, Eye Graphics Co., Ltd.). The conditions in the curing oven were 0.5 m/s and 26 mW/cm 2 , and the total dosage of irradiation was lOOO mJ/cm 2 . The curing process was carried out in a nitrogen gas atmosphere (O2 concentration ⁇ 200 ppm). The adhesive composition (pressure-sensitive adhesive) on the PET film obtained thereby was laminated with another silicone-treated PET film.
- a UV curing oven 365 nm, UV (365) N 2 purge UV irradiation device, Eye Graphics Co., Ltd.
- the conditions in the curing oven were 0.5 m/s and 26 mW/cm 2 , and the
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012-086811 | 2012-04-05 | ||
| JP2012086811A JP5989381B2 (ja) | 2012-04-05 | 2012-04-05 | 放射線硬化性粘着組成物及びそれを用いた積層体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2013152251A1 true WO2013152251A1 (en) | 2013-10-10 |
Family
ID=48142095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2013/035357 WO2013152251A1 (en) | 2012-04-05 | 2013-04-05 | Radiation-cured adhesive composition and laminate using the same |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP5989381B2 (enrdf_load_stackoverflow) |
| WO (1) | WO2013152251A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103526596A (zh) * | 2013-10-23 | 2014-01-22 | 合肥聚合辐化技术有限公司 | 一种环保低温固化印花粘合剂及其制备方法 |
| CN109554155A (zh) * | 2017-09-25 | 2019-04-02 | 3M创新有限公司 | 可印刷、可辐射固化的粘合剂组合物及其应用 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022255308A1 (ja) | 2021-06-02 | 2022-12-08 | 積水化学工業株式会社 | 紫外線硬化型粘着剤組成物、及び、粘着剤 |
| US20240301243A1 (en) | 2021-06-02 | 2024-09-12 | Sekisui Chemical Co., Ltd. | Ultraviolet-curable composition |
| KR20240015617A (ko) | 2021-06-02 | 2024-02-05 | 세키스이가가쿠 고교가부시키가이샤 | 자외선 경화형 방열성 수지 조성물, 방열성 점착 시트, 적층체, 및 적층체의 제조 방법 |
| WO2024117229A1 (ja) | 2022-12-01 | 2024-06-06 | 積水化学工業株式会社 | 印刷用光硬化型粘着剤組成物、硬化物、及び、積層体 |
| CN119698450A (zh) | 2022-12-01 | 2025-03-25 | 积水化学工业株式会社 | 粘合片和层叠体的制造方法 |
| JP7637318B2 (ja) | 2022-12-01 | 2025-02-27 | 積水化学工業株式会社 | 粘着シート、及び、積層体の製造方法 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61209281A (ja) | 1985-03-13 | 1986-09-17 | Hitachi Chem Co Ltd | 放射線硬化型粘着剤組成物 |
| JPH04183770A (ja) | 1990-11-16 | 1992-06-30 | Osaka Organic Chem Ind Ltd | 放射線硬化型粘着剤組成物 |
| JPH06107993A (ja) * | 1992-09-25 | 1994-04-19 | Nippon Kayaku Co Ltd | スクリーン印刷インキ組成物 |
| JPH11246612A (ja) | 1998-03-03 | 1999-09-14 | Teikoku Ink Seizo Kk | 紫外線硬化性液状組成物及びこれを用いた製品 |
| WO1999050368A1 (en) * | 1998-03-27 | 1999-10-07 | Dsm N.V. | Radiation curable adhesive for digital versatile disc |
| JP2004143223A (ja) | 2002-10-22 | 2004-05-20 | Tomoegawa Paper Co Ltd | 半導体ウエハ加工用粘着シートおよびそれを用いた半導体ウエハの加工方法 |
| JP2004323796A (ja) | 2003-04-28 | 2004-11-18 | The Inctec Inc | 紫外線硬化型粘着剤組成物 |
| US20060128856A1 (en) * | 2002-09-30 | 2006-06-15 | Jrs Corporation | Liquid curable resin composition |
| US20110070433A1 (en) * | 2009-09-24 | 2011-03-24 | Lintec Corporation | Sheet and Adhesive Sheet |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4538189B2 (ja) * | 2002-12-27 | 2010-09-08 | 株式会社イーテック | 再剥離性粘着加工紙用組成物および再剥離性粘着加工紙 |
| CN103140560B (zh) * | 2010-10-01 | 2014-05-28 | 昭和电工株式会社 | 光固化性透明粘合片用组合物 |
-
2012
- 2012-04-05 JP JP2012086811A patent/JP5989381B2/ja not_active Expired - Fee Related
-
2013
- 2013-04-05 WO PCT/US2013/035357 patent/WO2013152251A1/en active Application Filing
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61209281A (ja) | 1985-03-13 | 1986-09-17 | Hitachi Chem Co Ltd | 放射線硬化型粘着剤組成物 |
| JPH04183770A (ja) | 1990-11-16 | 1992-06-30 | Osaka Organic Chem Ind Ltd | 放射線硬化型粘着剤組成物 |
| JPH06107993A (ja) * | 1992-09-25 | 1994-04-19 | Nippon Kayaku Co Ltd | スクリーン印刷インキ組成物 |
| JPH11246612A (ja) | 1998-03-03 | 1999-09-14 | Teikoku Ink Seizo Kk | 紫外線硬化性液状組成物及びこれを用いた製品 |
| WO1999050368A1 (en) * | 1998-03-27 | 1999-10-07 | Dsm N.V. | Radiation curable adhesive for digital versatile disc |
| US20060128856A1 (en) * | 2002-09-30 | 2006-06-15 | Jrs Corporation | Liquid curable resin composition |
| JP2004143223A (ja) | 2002-10-22 | 2004-05-20 | Tomoegawa Paper Co Ltd | 半導体ウエハ加工用粘着シートおよびそれを用いた半導体ウエハの加工方法 |
| JP2004323796A (ja) | 2003-04-28 | 2004-11-18 | The Inctec Inc | 紫外線硬化型粘着剤組成物 |
| US20110070433A1 (en) * | 2009-09-24 | 2011-03-24 | Lintec Corporation | Sheet and Adhesive Sheet |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE WPI Week 199420, Derwent World Patents Index; AN 1994-164188, XP002711175 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103526596A (zh) * | 2013-10-23 | 2014-01-22 | 合肥聚合辐化技术有限公司 | 一种环保低温固化印花粘合剂及其制备方法 |
| CN109554155A (zh) * | 2017-09-25 | 2019-04-02 | 3M创新有限公司 | 可印刷、可辐射固化的粘合剂组合物及其应用 |
| CN109554155B (zh) * | 2017-09-25 | 2021-04-02 | 3M创新有限公司 | 可印刷、可辐射固化的粘合剂组合物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5989381B2 (ja) | 2016-09-07 |
| JP2013216742A (ja) | 2013-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2013152251A1 (en) | Radiation-cured adhesive composition and laminate using the same | |
| TWI702272B (zh) | 黏著片材、具有黏著劑層之積層體的製造方法、具有黏著劑層之積層體、影像顯示裝置及觸控面板 | |
| TWI706016B (zh) | 光硬化型接著組成物 | |
| EP2154215B1 (en) | Method for adhering adhesive sheet to automotive coating surface | |
| JP2013166846A (ja) | 粘着シート、接着用シート、光硬化型接着剤組成物及び光学用部材 | |
| KR20190135564A (ko) | 광경화성 수지 조성물, 유기 el 표시 소자용 밀봉제, 유기 el 표시 소자, 양자 도트 디바이스용 밀봉제, 및 양자 도트 디바이스 | |
| JP6556550B2 (ja) | 光硬化性粘着剤組成物 | |
| KR20130129236A (ko) | 점착체 조성물, 점착제, 및 이를 사용하여 이루어진 점착 시트 | |
| US20140131306A1 (en) | Photocurable adhesive composition and use of the same | |
| KR102046656B1 (ko) | 점착 시트 및 점착제 조성물 | |
| TW201420718A (zh) | 光硬化型黏著劑組成物、硬化物、黏著片及顯示面板與其製造方法 | |
| CN114729237A (zh) | 双面粘合带 | |
| KR102031528B1 (ko) | 광 경화성 수지 조성물, 및 화상 표시 장치의 제조 방법 | |
| KR20150099558A (ko) | 분해성 단량체 및 중합체로부터 제조된 감압 접착제 | |
| KR20170098273A (ko) | 산 함량이 낮은 점착부여된 아크릴레이트 감압 접착제 | |
| TW201446910A (zh) | 黏著劑及使用其之圖像顯示裝置 | |
| WO2013161759A1 (ja) | 透明粘接着シート用組成物、その製造方法及び透明粘接着シート | |
| KR20180093047A (ko) | 경화성 조성물, 감압 접착제, 접착 테이프, 접착 제품 | |
| JP6074144B2 (ja) | 光学用フィルム、並びにディスプレイ装置 | |
| KR20140099187A (ko) | 자외선 경화형 아크릴계 점착제층을 갖는 점착 시트의 제조 방법 | |
| JP4656626B2 (ja) | アクリル系粘着剤層およびアクリル系粘着シート | |
| JP6612553B2 (ja) | 積層体フィルムおよび粘着シート | |
| KR20240015056A (ko) | 자외선 경화성 조성물 | |
| KR20250113984A (ko) | 광경화성 수지 조성물, 점착 시트, 및, 적층체의 제조 방법 | |
| JP7736513B2 (ja) | 光硬化型樹脂組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13717390 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 13717390 Country of ref document: EP Kind code of ref document: A1 |