JP5735279B2 - 化学線硬化型接着剤組成物 - Google Patents
化学線硬化型接着剤組成物 Download PDFInfo
- Publication number
- JP5735279B2 JP5735279B2 JP2010540913A JP2010540913A JP5735279B2 JP 5735279 B2 JP5735279 B2 JP 5735279B2 JP 2010540913 A JP2010540913 A JP 2010540913A JP 2010540913 A JP2010540913 A JP 2010540913A JP 5735279 B2 JP5735279 B2 JP 5735279B2
- Authority
- JP
- Japan
- Prior art keywords
- actinic radiation
- radiation curable
- curable adhesive
- adhesive composition
- plasticizer
- 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.)
- Expired - Fee Related
Links
- 239000000853 adhesive Substances 0.000 title claims description 94
- 230000001070 adhesive effect Effects 0.000 title claims description 94
- 239000000203 mixture Substances 0.000 title claims description 76
- 230000005855 radiation Effects 0.000 title claims description 40
- 239000004014 plasticizer Substances 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 239000012986 chain transfer agent Substances 0.000 claims description 26
- 238000011176 pooling Methods 0.000 claims description 19
- 239000003999 initiator Substances 0.000 claims description 18
- 239000011521 glass Substances 0.000 claims description 17
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 16
- 238000012360 testing method Methods 0.000 claims description 15
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims description 11
- SCABKEBYDRTODC-UHFFFAOYSA-N bis[2-(2-butoxyethoxy)ethyl] hexanedioate Chemical compound CCCCOCCOCCOC(=O)CCCCC(=O)OCCOCCOCCCC SCABKEBYDRTODC-UHFFFAOYSA-N 0.000 claims description 6
- DKWHHTWSTXZKDW-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxymethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCOCCOCCOCCCC DKWHHTWSTXZKDW-UHFFFAOYSA-N 0.000 claims description 5
- 238000010030 laminating Methods 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 16
- 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 10
- 238000000034 method Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 6
- -1 acylalkylene Chemical group 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 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 5
- 239000000126 substance Substances 0.000 description 5
- AGWWTUWTOBEQFE-UHFFFAOYSA-N 4-methyl-1h-1,2,4-triazole-5-thione Chemical compound CN1C=NN=C1S AGWWTUWTOBEQFE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940116351 sebacate Drugs 0.000 description 4
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 3
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 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
- 238000001723 curing Methods 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 1
- MKCQPZUQENGUHZ-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-1,2,3,4,4,5-hexakis-phenylimidazolidine Chemical class C1(=CC=CC=C1)C1C(N(C(N1C1=CC=CC=C1)(C=1NC=CN1)C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 MKCQPZUQENGUHZ-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- 101150108397 Abcd2 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- OSYQOBUUFRGFNG-UHFFFAOYSA-N Sebacic acid monomethyl ester Chemical compound COC(=O)CCCCCCCCC(O)=O OSYQOBUUFRGFNG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- WGOQVOGFDLVJAW-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCOC(N)=O WGOQVOGFDLVJAW-UHFFFAOYSA-N 0.000 description 1
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 239000012788 optical film Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US940607P | 2007-12-28 | 2007-12-28 | |
| US61/009,406 | 2007-12-28 | ||
| PCT/US2008/088387 WO2009086491A1 (en) | 2007-12-28 | 2008-12-29 | Actinically curable adhesive composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011511851A JP2011511851A (ja) | 2011-04-14 |
| JP2011511851A5 JP2011511851A5 (enExample) | 2012-02-23 |
| JP5735279B2 true JP5735279B2 (ja) | 2015-06-17 |
Family
ID=40437135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010540913A Expired - Fee Related JP5735279B2 (ja) | 2007-12-28 | 2008-12-29 | 化学線硬化型接着剤組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110201717A1 (enExample) |
| JP (1) | JP5735279B2 (enExample) |
| KR (1) | KR20100112148A (enExample) |
| CN (1) | CN101970590A (enExample) |
| TW (1) | TW200942562A (enExample) |
| WO (1) | WO2009086491A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120072163A (ko) | 2010-12-23 | 2012-07-03 | 제일모직주식회사 | Ｏｃａ 필름용 광학 점착제 조성물 |
| KR101362869B1 (ko) * | 2010-12-29 | 2014-02-14 | 제일모직주식회사 | 광학 점착제 조성물 |
| TWI465534B (zh) * | 2010-12-31 | 2014-12-21 | Eternal Materials Co Ltd | 可光固化之黏著組合物 |
| US8957156B2 (en) | 2010-12-31 | 2015-02-17 | Cheil Industries, Inc. | Optical adhesive composition for displays, optical adhesive film prepared from the same, and display panel including the same |
| KR101351624B1 (ko) * | 2010-12-31 | 2014-01-15 | 제일모직주식회사 | 광경화형 점착제 조성물 및 이를 이용한 모바일 폰의 모듈 조립 방법 |
| TWI490299B (zh) * | 2011-05-05 | 2015-07-01 | Eternal Materials Co Ltd | 丙烯酸系黏著組合物及其用途 |
| TWI522742B (zh) * | 2011-07-04 | 2016-02-21 | Photocurable resin composition and use thereof | |
| CN102898956A (zh) * | 2011-07-25 | 2013-01-30 | 汉高股份有限公司 | 光固化的粘合剂组合物及其用途 |
| CN102504753B (zh) * | 2011-10-18 | 2014-03-05 | 烟台德邦科技有限公司 | 一种紫外光固化胶及其制备方法 |
| WO2013057958A1 (ja) * | 2011-10-21 | 2013-04-25 | 日本化薬株式会社 | 光学部材の製造方法及びそのための紫外線硬化型樹脂組成物の使用 |
| CN104024295B (zh) * | 2011-11-21 | 2016-10-19 | 日本化药株式会社 | 紫外线固化型树脂组合物及其固化物的剥离方法 |
| JPWO2013084503A1 (ja) * | 2011-12-08 | 2015-04-27 | 日本化薬株式会社 | 光学部材、紫外線硬化型樹脂組成物及び硬化物 |
| KR20140145933A (ko) * | 2012-01-25 | 2014-12-24 | 데쿠세리아루즈 가부시키가이샤 | 화상 표시 장치의 제조 방법 |
| CN104334662B (zh) | 2012-05-21 | 2018-11-09 | 东进世美肯株式会社 | 光固化型光学透明粘合剂组合物及包含其的粘合片 |
| WO2013176436A1 (ko) * | 2012-05-21 | 2013-11-28 | 주식회사 동진쎄미켐 | 광경화형 광투명 점,접착제 조성물 및 이를 포함하는 점,접착 시트 |
| ES2835227T3 (es) * | 2012-05-22 | 2021-06-22 | Henkel IP & Holding GmbH | Proceso para la unión de sustratos con un adhesivo líquido fotopolimerizable ópticamente transparente |
| ES2871913T3 (es) | 2012-05-22 | 2021-11-02 | Henkel IP & Holding GmbH | Adhesivo líquido fotocurable ópticamente transparente |
| KR101642635B1 (ko) | 2012-05-29 | 2016-07-25 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 액체 광학 접착제 조성물 |
| CN102703020B (zh) * | 2012-06-12 | 2013-10-23 | 烟台德邦科技有限公司 | 一种具有耐冲击性能的液态光学透明胶及其制备方法 |
| WO2014028024A1 (en) * | 2012-08-16 | 2014-02-20 | E. I. Du Pont De Nemours And Company | Actinically curable adhesive composition and bonding method using same |
| WO2014029062A1 (en) * | 2012-08-20 | 2014-02-27 | Henkel (China) Company Limited | Liquid optically clear photo-curable adhesive for display application |
| CN104837938A (zh) | 2012-12-10 | 2015-08-12 | 3M创新有限公司 | 液体光学粘合剂组合物 |
| WO2014093141A1 (en) * | 2012-12-14 | 2014-06-19 | 3M Innovative Properties Company | Method of making packaged viscoelastic compositions by polymerizing ethylenically-unsaturated materials using ionizing radiation |
| CN103484051A (zh) * | 2013-09-29 | 2014-01-01 | 苏州华周胶带有限公司 | 一种热封胶带黏合剂 |
| CN105764930B (zh) * | 2013-11-27 | 2018-11-16 | 电化株式会社 | 组合物 |
| WO2015079728A1 (ja) * | 2013-11-29 | 2015-06-04 | Dic株式会社 | 光硬化性光学接着剤組成物、その硬化物、及び液晶表示装置 |
| WO2016077984A1 (en) * | 2014-11-18 | 2016-05-26 | Henkel (China) Company Limited | Photo-curable adhesive composition, preparation and use thereof |
| KR102257987B1 (ko) | 2014-12-16 | 2021-05-31 | 삼성디스플레이 주식회사 | 광학용 투명 점착 조성물 및 이를 포함하는 표시장치 |
| JP6797112B2 (ja) * | 2015-05-26 | 2020-12-09 | デンカ株式会社 | 組成物 |
| JP6649964B2 (ja) * | 2015-05-26 | 2020-02-19 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | 光硬化性接着剤組成物、その調製およびその使用 |
| US10712483B2 (en) * | 2015-08-24 | 2020-07-14 | Samsung Electronics Co., Ltd. | Photosensitive compositions, quantum dot polymer composite pattern prepared therefrom, and electronic devices including the same |
| KR102527764B1 (ko) | 2015-12-17 | 2023-05-02 | 삼성전자주식회사 | 감광성 조성물, 이를 제조하기 위한 방법, 및 이로부터 제조된 양자점-폴리머 복합체 패턴 |
| KR102359125B1 (ko) | 2016-03-15 | 2022-02-08 | 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 | 티오우레탄 중합체, 이의 제조 방법, 및 적층 제조 기술에서의 용도 |
| KR20210030895A (ko) * | 2018-03-28 | 2021-03-18 | 벤자민 룬드 | 티올-아크릴레이트 중합체, 이의 합성 방법 및 적층식 제조 기술에서의 용도 |
| US11739177B2 (en) | 2018-04-20 | 2023-08-29 | Adaptive 3D Technologies | Sealed isocyanates |
| EP3781375A4 (en) | 2018-04-20 | 2021-09-29 | Benjamin Lund | BLOCKED ISOCYANATES |
| US11911956B2 (en) | 2018-11-21 | 2024-02-27 | Adaptive 3D Technologies | Using occluding fluids to augment additive manufacturing processes |
| US12054654B2 (en) | 2019-05-15 | 2024-08-06 | Hewlett-Packard Development Company, L.P. | Re-workable adhesives for electronic devices |
| AU2020314047A1 (en) * | 2019-07-12 | 2022-02-17 | Mondofix Inc. | Thiol-based adhesive formulations for repairing windshields |
| JP7513029B2 (ja) * | 2019-07-29 | 2024-07-09 | 株式会社レゾナック | 粘着シート |
| CN115353849A (zh) * | 2022-08-05 | 2022-11-18 | Tcl华星光电技术有限公司 | 一种封装材料、显示面板及其封装方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2606569A1 (de) * | 1976-02-19 | 1977-08-25 | Degussa | Verfahren zur herstellung von beschussfesten verbund(glas)scheiben |
| JPS63260971A (ja) * | 1987-04-20 | 1988-10-27 | Hitachi Chem Co Ltd | 放射線硬化型粘着剤組成物 |
| JPH01156387A (ja) * | 1987-12-14 | 1989-06-19 | Cemedine Co Ltd | 耐水性を有する光硬化型接着剤組成物 |
| JPH0778202B2 (ja) * | 1988-10-18 | 1995-08-23 | 積水化学工業株式会社 | アクリル系粘着テープもしくはシートの製造方法 |
| DE59209143D1 (de) * | 1991-03-27 | 1998-02-26 | Ciba Geigy Ag | Photoempfindliches Gemisch auf Basis von Acrylaten |
| US5747551A (en) * | 1994-12-05 | 1998-05-05 | Acheson Industries, Inc. | UV curable pressure sensitive adhesive composition |
| JP3797628B2 (ja) * | 1995-11-08 | 2006-07-19 | 日東電工株式会社 | 感圧接着剤及びその接着シート |
| JP3177149B2 (ja) * | 1996-03-15 | 2001-06-18 | リンテック株式会社 | 粘着テープ用基材、該基材を用いた粘着テープ、および該基材の製造方法 |
| JP2000508685A (ja) * | 1996-04-05 | 2000-07-11 | ミネソタ・マイニング・アンド・マニュファクチャリング・カンパニー | 可視光線重合可能組成物 |
| JPH09291258A (ja) * | 1996-04-26 | 1997-11-11 | Lintec Corp | 粘着剤組成物およびこれを用いた粘着シート |
| US6180200B1 (en) * | 1998-06-01 | 2001-01-30 | Dsm N. V. | Cationic and hybrid radiation curable pressure sensitive adhesives for bonding of optical discs |
| JP3484985B2 (ja) * | 1998-08-17 | 2004-01-06 | 東亞合成株式会社 | 光硬化型接着剤組成物 |
| JP2000345111A (ja) * | 1999-06-07 | 2000-12-12 | Three M Innovative Properties Co | 接着剤組成物及びそれを用いた光ディスク |
| US6617371B2 (en) * | 2001-06-08 | 2003-09-09 | Addison Clear Wave, Llc | Single component room temperature stable heat-curable acrylate resin adhesive |
| US20060154169A1 (en) * | 2003-06-11 | 2006-07-13 | Hans-Joachim Timpe | Radiation-sensitive compositions comprising a 1,4-dihydropyridine sensitizer and imageable elements based thereon |
| JP2005058288A (ja) * | 2003-08-19 | 2005-03-10 | Three M Innovative Properties Co | 医療用粘着テープのための粘着剤組成物及び粘着テープ |
| JP4433181B2 (ja) * | 2004-09-22 | 2010-03-17 | 株式会社スリーボンド | 放射線硬化型マイクロカプセル含有組成物及びそれを用いたマイクロカプセル含有被覆層の形成方法。 |
| US7241636B2 (en) * | 2005-01-11 | 2007-07-10 | Freescale Semiconductor, Inc. | Method and apparatus for providing structural support for interconnect pad while allowing signal conductance |
| EP1879938B1 (en) * | 2005-05-02 | 2012-04-18 | Cytec Surface Specialties, S.A. | Radiation curable urethane (meth)acrylate polymer and adhesives formulated with them |
| US7348132B2 (en) * | 2006-01-21 | 2008-03-25 | Gary Ganghui Teng | Laser sensitive lithographic printing plate having specific photopolymer composition |
| KR20090086519A (ko) * | 2006-10-11 | 2009-08-13 | 헥시온 스페셜티 케미칼즈 인코퍼레이티드 | 방사선 경화성 및 분사성 잉크 조성물 |
-
2008
- 2008-12-29 TW TW097151327A patent/TW200942562A/zh unknown
- 2008-12-29 KR KR1020107016826A patent/KR20100112148A/ko not_active Withdrawn
- 2008-12-29 CN CN2008801267830A patent/CN101970590A/zh active Pending
- 2008-12-29 JP JP2010540913A patent/JP5735279B2/ja not_active Expired - Fee Related
- 2008-12-29 WO PCT/US2008/088387 patent/WO2009086491A1/en not_active Ceased
- 2008-12-29 US US12/810,175 patent/US20110201717A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101970590A (zh) | 2011-02-09 |
| JP2011511851A (ja) | 2011-04-14 |
| KR20100112148A (ko) | 2010-10-18 |
| WO2009086491A1 (en) | 2009-07-09 |
| US20110201717A1 (en) | 2011-08-18 |
| TW200942562A (en) | 2009-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5735279B2 (ja) | 化学線硬化型接着剤組成物 | |
| JP2011508814A (ja) | 熱および化学線硬化型接着剤組成物 | |
| KR101966479B1 (ko) | 방사선 경화성 감압 접착제 시트 | |
| JP6065002B2 (ja) | 画像表示装置用粘着シート、画像表示装置の製造方法及び画像表示装置 | |
| CN102144009B (zh) | 用于粘贴光学功能材料的光固化型树脂组合物 | |
| WO2014176209A1 (en) | Method of producing a laminate comprising a cured adhesive sheet | |
| JP7282687B2 (ja) | 光学透明粘着シート、これを製造するための組成物およびこれを用いた平板表示装置 | |
| WO2014028024A1 (en) | Actinically curable adhesive composition and bonding method using same | |
| JP7778830B2 (ja) | 光学用粘着剤組成物、粘着フィルム、粘着シート、及び粘着剤層付き光学フィルム | |
| US20130284360A1 (en) | Actinically curable adhesive composition | |
| JP2025089395A (ja) | 粘着剤組成物、タッチパネル用粘着フィルム、粘着剤層付き光学フィルム | |
| JP6687655B2 (ja) | 粘着剤組成物及び粘着フィルム | |
| KR102104663B1 (ko) | 터치패널용 점착제 조성물 및 점착필름 | |
| JP7079808B2 (ja) | 粘着剤層の製造方法、及び粘着フィルムの製造方法 | |
| JP2018083851A (ja) | 画像表示装置用粘着シート、画像表示装置用粘着積層体及び画像表示装置 | |
| JP7278967B2 (ja) | 光学透明粘着シート | |
| JP6904926B2 (ja) | 粘着剤層及び粘着フィルム | |
| JP2020114923A (ja) | 粘着フィルム | |
| KR20200052038A (ko) | Oca 필름용 점착 조성물, 및 그로부터 제조된 oca 필름 및 터치 스크린 패널 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120104 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120104 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130515 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130531 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130827 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130903 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130930 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131007 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131031 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140624 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140924 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141001 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141024 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141031 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20141125 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20141202 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141224 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150317 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150416 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5735279 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees | ||
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |