WO2016125642A1 - Composition et article moulé - Google Patents
Composition et article moulé Download PDFInfo
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- WO2016125642A1 WO2016125642A1 PCT/JP2016/052239 JP2016052239W WO2016125642A1 WO 2016125642 A1 WO2016125642 A1 WO 2016125642A1 JP 2016052239 W JP2016052239 W JP 2016052239W WO 2016125642 A1 WO2016125642 A1 WO 2016125642A1
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- Prior art keywords
- polymer
- monomer
- acrylic
- group
- composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 229920000642 polymer Polymers 0.000 claims description 106
- 239000000178 monomer Substances 0.000 claims description 72
- 239000004593 Epoxy Substances 0.000 claims description 44
- 229920000058 polyacrylate Polymers 0.000 claims description 42
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 30
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000853 adhesive Substances 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 9
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 9
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229920006226 ethylene-acrylic acid Polymers 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000000576 coating method Methods 0.000 abstract description 75
- 239000011248 coating agent Substances 0.000 abstract description 67
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 description 56
- 239000002184 metal Substances 0.000 description 56
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 44
- 229910052802 copper Inorganic materials 0.000 description 43
- 239000010949 copper Substances 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 39
- 239000010410 layer Substances 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 34
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- 229910052709 silver Inorganic materials 0.000 description 32
- 239000004332 silver Substances 0.000 description 32
- -1 benzotriazole compound Chemical class 0.000 description 20
- 238000001723 curing Methods 0.000 description 19
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- 239000005020 polyethylene terephthalate Substances 0.000 description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- 239000002082 metal nanoparticle Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002105 nanoparticle Substances 0.000 description 8
- 239000002070 nanowire Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 7
- 239000002923 metal particle Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910052762 osmium Inorganic materials 0.000 description 7
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229910052703 rhodium Inorganic materials 0.000 description 6
- 239000010948 rhodium Substances 0.000 description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000008199 coating composition Substances 0.000 description 5
- 229910052750 molybdenum Inorganic materials 0.000 description 5
- 239000011733 molybdenum Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 238000005536 corrosion prevention Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920002313 fluoropolymer Polymers 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000010702 perfluoropolyether Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 2
- TYCFGHUTYSLISP-UHFFFAOYSA-N 2-fluoroprop-2-enoic acid Chemical group OC(=O)C(F)=C TYCFGHUTYSLISP-UHFFFAOYSA-N 0.000 description 2
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000004888 barrier function Effects 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003209 poly(hydridosilsesquioxane) Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910003445 palladium oxide Inorganic materials 0.000 description 1
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- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
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- 230000003449 preventive effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
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- 238000010345 tape casting Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Definitions
- the present invention relates to a composition containing a nitrogen-containing aromatic heterocyclic compound and a molded article comprising the composition.
- Patent Document 1 describes a composition containing a perfluoropolyether benzotriazole compound and a perfluoropolyether benzotriazole compound, and the perfluoropolyether benzotriazole compound is bonded to a metal substrate to prevent contamination. It is described that it is possible to provide at least one of properties and stain prevention properties, easy cleaning properties, water repellency, hydrophobic or oleophobic properties.
- the coating film is generally required to have adhesion with the substrate. Depending on the application, the coating film is required to have not only adhesion but also high transparency. Then, an object of this invention is to provide the composition which can form the coating film which is excellent in adhesiveness and transparency.
- the present invention includes a nitrogen-containing aromatic heterocyclic compound and component (A),
- the nitrogen-containing aromatic heterocyclic compound has the following formula (1): (In the formula, ring A is an optionally substituted 5- or 6-membered nitrogen-containing aromatic heterocyclic ring, ring B is an unsubstituted aromatic ring, and R 1 is a hydrogen atom, a halogen atom or A C 1-6 alkyl group, Q 1 is —O— or —NH—, l1 is 0 or 1, m1 is an integer of 1 to 20, and n1 is an integer of 1 to 6. However, when m1 is 1, n1 is an integer of 1 to 3, and when m1 is 2, n1 is an integer of 1 to 5).
- Component (A) provides fluorine-containing polymer, epoxy polymer, silicone polymer, urethane polymer, acrylic polymer, ethylene-vinyl acetate polymer, butadiene polymer, cellulose polymer, monomer that provides epoxy polymer, monomer that provides silicone polymer, and urethane polymer
- the composition is at least one selected from the group consisting of a monomer and a monomer that gives an acrylic polymer.
- ring A is preferably a 5-membered nitrogen-containing aromatic heterocyclic ring containing 2 or 3 nitrogen atoms.
- the ring B is preferably a benzene ring.
- Component (A) is an epoxy polymer, a silicone polymer, a urethane polymer, an acrylic polymer, an ethylene-vinyl acetate polymer, a butadiene polymer, a cellulose polymer, a monomer that provides an epoxy polymer, a monomer that provides a silicone polymer, a monomer that provides a urethane polymer, and It is preferably at least one selected from the group consisting of monomers that give acrylic polymers.
- the component (A) is at least one selected from the group consisting of an epoxy polymer, a monomer that provides an epoxy polymer, an acrylic polymer, a monomer that provides an acrylic polymer, a silicone polymer, and a monomer that provides a silicone polymer. .
- Acrylic polymers include ethylene-acrylic acid copolymer, ethylene-acrylic acid ester copolymer, ethylene-acrylic acid salt copolymer, acrylic acid ester rubber, (meth) acrylic acid ester homopolymer, and ( It is preferably at least one selected from the group consisting of copolymers of (meth) acrylic acid esters and other monomers.
- the monomer that gives the acrylic polymer is preferably at least one selected from the group consisting of (meth) acrylic acid esters and polyfunctional acrylic monomers.
- composition preferably further contains a curing agent or initiator.
- the composition preferably contains 0.01 to 30% by mass of a nitrogen-containing aromatic heterocyclic compound.
- composition preferably further contains a solvent.
- the composition is preferably an adhesive.
- the composition preferably further contains a conductive substance (C).
- the conductive substance (C) is preferably at least one selected from the group consisting of conductive particles and conductive fibers.
- the present invention is also a molded article comprising the above-described composition.
- the present invention is also a sheet made of the above-described composition.
- the present invention relates to an epoxy polymer, a silicone polymer, a urethane polymer, an acrylic polymer, an ethylene-vinyl acetate polymer, a butadiene polymer, a cellulose polymer, a monomer that provides an epoxy polymer, a monomer that provides a silicone polymer, a monomer that provides a urethane polymer, and an acrylic polymer It is also a sheet characterized in that it is formed from at least one component (A) selected from the group consisting of monomers that give a b * value of 0.8 or less and Haze is less than 1% .
- A component selected from the group consisting of monomers that give a b * value of 0.8 or less and Haze is less than 1% .
- composition of the present invention can form a coating film having high adhesion and excellent transparency. Moreover, the formed coating film is excellent also in the effect which prevents metal corrosion.
- the molded article of the present invention has high adhesion to the substrate and is excellent in transparency.
- composition of this invention contains a nitrogen-containing aromatic heterocyclic compound and a component (A).
- the nitrogen-containing aromatic heterocyclic compound has the following formula (1):
- ring A is an optionally substituted 5- or 6-membered nitrogen-containing aromatic heterocyclic ring
- ring B is an unsubstituted aromatic ring
- R 1 is a hydrogen atom, a halogen atom or A C 1-6 alkyl group
- Q 1 is —O— or —NH—
- l1 is 0 or 1
- m1 is an integer of 1 to 20
- n1 is an integer of 1 to 6.
- n1 is an integer of 1 to 3
- n1 is an integer of 1 to 5.
- the above compound is characterized in that the aromatic ring of ring B is not substituted with a substituent.
- a transparent coating such as a coating having a large b * value in the L * a * b * color system is formed. A film cannot be formed.
- the ring A is preferably a 5-membered or 6-membered nitrogen-containing aromatic heterocycle which is not substituted with a substituent other than the substituent explicitly shown in the formula (1).
- a more transparent coating film can be formed.
- ring A is substituted with a hydroxyl group or a substituent having a hydroxyl group, for example, a coating film having a large b * value in the L * a * b * color system is formed. A coating film cannot be formed.
- n1 is preferably 1 or 2.
- Ring A ′ is an optionally substituted 5- or 6-membered nitrogen-containing aromatic heterocycle. Since ring A ′ can form a highly transparent coating film, it may be a 5- or 6-membered nitrogen-containing aromatic heterocyclic ring that is not substituted with a substituent other than the substituents specified in the above formula. preferable.
- the ring A is preferably a 5-membered nitrogen-containing aromatic heterocyclic ring containing 2 or 3 nitrogen atoms, and more preferably an imidazole ring, a pyrazole ring or a triazole ring.
- l1 is preferably 0.
- the ring B is preferably a benzene ring.
- composition of the present invention preferably contains 0.01 to 30% by mass of a nitrogen-containing aromatic heterocyclic compound because it can form a coating film having excellent adhesion and transparency.
- the compound represented by the formula (1) can be produced by reacting the compound represented by the formula (7) with the compound represented by the formula (8).
- ring A is an optionally substituted 5- or 6-membered nitrogen-containing aromatic heterocycle
- ring B is an unsubstituted aromatic ring.
- L 11 is a functional group capable of reacting with a hydroxyl group or amino group
- R 1 and n1 are as described above for R 1 and n1 of formula (1).
- the amino group may be a secondary amine (—NH—) of a nitrogen-containing aromatic heterocyclic ring.
- the compound represented by formula (7) has the formula Is preferably a compound represented by the formula More preferably, the compound is represented by the formula: It is further more preferable that it is a compound shown by these.
- Ring A ′ is an optionally substituted 5- or 6-membered nitrogen-containing aromatic heterocycle. Ring A ′ is preferably an unsubstituted 5- or 6-membered nitrogen-containing aromatic heterocyclic ring. Ring A "is not substituted.
- the compound represented by the formula (8) is preferably an isocyanate compound represented by the formula (9).
- m1, n1 and R 1 are as described above as m1, n1 and R 1 of formula (1).
- the compound represented by the formula (8) has the formula It is more preferable that it is either of the compounds shown by these.
- the compound represented by the formula (8) is 0.1 to 5 mol per 1 mol of the compound represented by the formula (7). Thus, it is preferable to add two compounds into the system and react.
- the reaction of the compound represented by the formula (7) and the compound represented by the formula (8) can be allowed to proceed at 15 to 100 ° C., preferably 15 to 70 ° C., more preferably 20 to 30 ° C. is there.
- the reaction time is usually 1 to 10 hours.
- the reaction between the compound represented by the formula (7) and the compound represented by the formula (8) may proceed in the presence of a catalyst.
- Catalysts include organic titanium compounds such as tetraethyl titanate and tetrabutyl titanate, organic tin compounds such as tin octylate, dibutyltin oxide, and dibutyltin dilaurate, and halogen-based stannous such as stannous chloride and stannous bromide. Etc.
- the amount of the catalyst used is not particularly limited and may be adjusted as appropriate. For example, it is usually about 0.00001 to 3 parts by mass, preferably about 0.001 to 3 parts by mass with respect to 100 parts by mass of the compound represented by formula (8). It is about 0001 to 1 part by mass.
- the reaction of the compound represented by the formula (7) and the compound represented by the formula (8) can be performed in a solvent.
- the solvent is a solvent that does not hinder the progress of the reaction, and a conventionally known solvent that is generally used may be used.
- ketone solvents such as acetone, methyl isobutyl ketone (MIBK) and methyl ethyl ketone (MEK); ester solvents such as ethyl acetate and butyl acetate; HCFC225 (CF 3 CF 2 CHCl 2 / CClF 2 CF 2 CHClF mixture)
- a fluorine-based solvent or the like may be used.
- An alcohol solvent having an OH group is not preferable because it prevents the reaction from proceeding. Further, since the progress of the reaction is hindered even if water is present in the system, each solvent is more preferably dehydrated before use.
- composition of the present invention further comprises a component (A).
- Component (A) provides fluorine-containing polymer, epoxy polymer, silicone polymer, urethane polymer, acrylic polymer, ethylene-vinyl acetate polymer, butadiene polymer, cellulose polymer, monomer that provides epoxy polymer, monomer that provides silicone polymer, and urethane polymer It is at least one selected from the group consisting of a monomer and a monomer that gives an acrylic polymer.
- Component (A) is an epoxy polymer, a silicone polymer, a urethane polymer, an acrylic polymer, an ethylene-vinyl acetate polymer, a butadiene polymer, a cellulose polymer, a monomer that provides an epoxy polymer, a monomer that provides a silicone polymer, a monomer that provides a urethane polymer, and It is preferably at least one selected from the group consisting of monomers that give acrylic polymers.
- the component (A) is at least one selected from the group consisting of an epoxy polymer, a monomer that provides an epoxy polymer, an acrylic polymer, a monomer that provides an acrylic polymer, a silicone polymer, and a monomer that provides a silicone polymer. .
- Examples of the monomers that give the epoxy polymer and the epoxy polymer include bisphenol A type, bisphenol F type, bisphenol AD type, bisphenol S type and other bisphenol type epoxy polymers, novolak type epoxy polymers, trisphenol methane triglycidyl ether, and the like.
- Aromatic epoxy polymers such as hydrogenated products and halides, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-2 -Methylcyclohexanecarboxylate, bis (3,4-epoxycyclohexyl) adipate, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6) Alicyclic epoxies such as methylcyclohexylmethyl) adipate, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexanone-meta-dioxane, bis (2,3-epoxycyclopentyl) ether Polymer, 1,4-butanediol diglycidyl ether, 1,6-hexan
- Glycidyl ester type epoxy polymer triglycidyl isocyanurate, N, N′-diglycidyl derivative of cyclic alkylene urea, N, N—O-triglycidyl derivative of p-aminophenol, N, N, of m-aminophenol
- Glycidylamine type epoxy polymers such as O-triglycidyl derivatives and hydrogenated products thereof; polyester polymers having at least two epoxy groups in one molecule; Examples thereof include urethane-modified epoxy polymers having a ethane bond introduced therein, and polycaprolactone-modified epoxy polymers having a polycaprolactone bond introduced into the structure of the above various epoxy resins.
- 1 type may be used for the said epoxy polymer and epoxy polymer, and 2 or more types may be used for them. *
- silicone polymer and the monomer that gives the silicone polymer include a monomer having a polydimethylsiloxane structure, a polymer, an elastomer, a sol-gel polymer of tetraalkoxysilane, a sol-gel polymer of trialkoxysilane, a sol-gel polymer of methyltrialkoxysilane, and a tetraalkoxy.
- Sol-gel polymer of silane and trialkoxysilane sol-gel polymer of tetraalkoxysilane and methyltrialkoxysilane, sol-gel polymer of methyltrialkoxysilane and trialkoxysilane, sol-gel polymer of tetraalkoxysilane and dimethylalkoxysilane, hydrogen silsesquioxane, Examples thereof include methyl silsesquioxane and fluorine-containing hydrogen silsesquioxane.
- Examples of the urethane polymer and the monomer that gives the urethane polymer include 4,4′-diphenylmethane diisocyanate, 2,4- and / or 2,6-toluene diisocyanate, polymethylene polyphenyl polyisocyanate, xylylene diisocyanate, 1,3. -(Bisocyanate) methylcyclohexane, isophorone diisocyanate and dimers, trimers, carbodiimide modified products, allophanate modified products, burette modified products, prepolymers and the like of these isocyanates. These may be used alone or in combination of two or more.
- the fluoropolymer has a fluoroalkyl group ester-bonded to a carboxyl group directly or via a divalent organic group, and has an acrylate ester which may have a substituent at the ⁇ -position as a structural unit.
- a fluorine-containing polymer is mentioned.
- the monomer that gives the acrylic polymer comprises (meth) acrylic acid ester, (meth) acrylic acid, hydroxyl group-containing (meth) acrylic acid ester, amino group-containing (meth) acrylic acid ester, and polyfunctional acrylic monomer. It is preferably at least one selected from the group, more preferably at least one selected from the group consisting of (meth) acrylic acid esters, (meth) acrylic acid and polyfunctional acrylic monomers. (Meth) acrylic acid esters and polyfunctional acrylic monomers are more preferred, and (meth) acrylic acid esters are particularly preferred. Most preferably, the (meth) acrylic acid ester is used alone, or both the (meth) acrylic acid ester and the polyfunctional acrylic monomer are used.
- (meth) acrylic acid ester when simply described as “(meth) acrylic acid ester”, it does not include a hydroxyl group-containing (meth) acrylic acid ester, an amino group-containing (meth) acrylic acid ester and a polyfunctional acrylic monomer.
- Examples of (meth) acrylate esters include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, and (meth) acrylic.
- I-butyl acid t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, lauryl (meth) acrylate, cyclohexyl (meth) acrylate and benzyl (meth) acrylate It is preferably at least one selected from the group consisting of: methyl (meth) acrylate is more preferred.
- polyfunctional acrylic monomers compounds in which hydroxyl groups of polyhydric alcohols such as diols, triols, and tetraols are replaced with acrylate groups, methacrylate groups, or ⁇ -fluoroacrylate groups are generally known. . Specifically, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, tripropylene glycol, neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, etc.
- Examples thereof include compounds in which two or more hydroxyl groups of polyhydric alcohols are replaced with acrylate groups, methacrylate groups, or ⁇ -fluoroacrylate groups.
- two or more hydroxyl groups of a polyhydric alcohol having a fluorine-containing alkyl group, a fluorine-containing alkyl group containing an ether bond, a fluorine-containing alkylene group or a fluorine-containing alkylene group containing an ether bond are converted into an acrylate group, a methacrylate group, ⁇ -A polyfunctional acrylic monomer substituted with a fluoroacrylate group can also be used, and is particularly preferable because the refractive index of the molded product can be kept low.
- polyfunctional (meth) acrylic acid ester is preferable, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, 1,2-propylene Glycol di (meth) acrylate, 1,3-propylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, 1,6-hexanediol di (Meth) acrylate, neopentyl glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, polyethylene glycol di (meth) acrylate, trimethylol prop It may be at least one selected from the group consisting of tri (meth) acrylate, pentaerythritol
- acrylic polymer examples include an ethylene-acrylic acid copolymer, an ethylene-acrylic acid ester copolymer, an ethylene-acrylic acid salt copolymer, an acrylic acid ester rubber, a (meth) acrylic acid ester homopolymer, and It is preferably at least one selected from the group consisting of copolymers of (meth) acrylic acid esters and other monomers.
- copolymer of (meth) acrylic acid ester As the copolymer of (meth) acrylic acid ester, (meth) acrylic acid ester, (meth) acrylic acid, hydroxyl group-containing (meth) acrylic acid ester, amino group-containing (meth) acrylic acid ester, polyfunctional acrylic At least one selected from the group consisting of a series monomer, alkyl vinyl ether, alkyl vinyl ester, crotonic acid, maleic acid, fumaric acid, itaconic acid, (meth) acrylonitrile, vinyl chloride, vinylidene chloride and (meth) acrylamide Copolymers with monomers are preferred.
- alkyl vinyl ether examples include methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether and the like.
- alkyl vinyl ester examples include vinyl formate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl caproate, and vinyl stearate.
- Hydroxyl group-containing (meth) acrylic acid esters include hydroxyethyl methacrylate (HEMA), hydroxyethyl acrylate (HEA), 3-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 4 -Hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 6-hydroxyhexyl acrylate, 6-hydroxyhexyl methacrylate, and the like.
- HEMA and HEA are preferable.
- the (meth) acrylic acid ester homopolymer and the (meth) acrylic acid ester copolymer have 1 to 100 mol% of polymerized units based on (meth) acrylic acid ester with respect to all polymerized units.
- the polymerized units based on (meth) acrylic acid esters are more preferably 50 to 100 mol%.
- the weight average molecular weight of the acrylic polymer is preferably in the range of 10,000 to 500,000. If the weight average molecular weight is too small, the gas barrier property (water vapor barrier property) may be inferior, and if the weight average molecular weight is too large, the compatibility with the vinylidene fluoride resin (B) may be inferior.
- the weight average molecular weight is more preferably 15,000 to 300,000.
- the weight average molecular weight of the acrylic polymer (A) can be calculated by, for example, gel permeation chromatography (GPC).
- the composition includes a VdF resin and a fluorine-containing polymer selected from the group consisting of a fluorine-containing polymer containing at least one group selected from the group consisting of a polymerizable functional group and a crosslinkable functional group ( B) may be included, but the mass ratio (A / B) between component (A) and fluoropolymer (B) is preferably more than 30/70, and includes fluoropolymer (B). Preferably not.
- the composition preferably further contains a curing agent or initiator.
- a curing agent or initiator include isocyanate, amine, silicate, mercaptan, phenol, amide, Lewis acid, acid anhydride, peroxide, and active energy ray curing initiators. it can.
- Examples of the isocyanate system include tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), xylylene diisocyanate (XDI), isophorone diisocyanate (IPDI), lysine methyl ester diisocyanate, methylcyclohexyl diisocyanate, trimethylhexamethylene diisocyanate, hexamethylene.
- Examples thereof include diisocyanate (HDI), n-pentane-1,4-diisocyanate, and the like, trimers thereof, adducts, nurates, and burettes.
- the active energy ray curing initiator for example, generates radicals and cations only when irradiated with electromagnetic waves in a wavelength region of 350 nm or less, that is, ultraviolet rays, electron beams, X rays, ⁇ rays, etc.
- Those that generate radicals and cations with ultraviolet light, particularly those that generate radicals are used.
- the following can be exemplified.
- Acetophenone series acetophenone, chloroacetophenone, diethoxyacetophenone, hydroxyacetophenone, ⁇ -aminoacetophenone, hydroxypropiophenone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinepropan-1-one, etc.
- Benzoin series benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal, and the like.
- Benzophenone series benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, hydroxy-propylbenzophenone, acrylated benzophenone, Michler's ketone, etc.
- Thioxanthones thioxanthone, chlorothioxanthone, methylxanthone, diethylthioxanthone, dimethylthioxanthone and the like.
- the composition contains a curing accelerator, a curing retarder, a pigment, a pigment dispersant, an antifoaming agent, a leveling agent, an ultraviolet absorber, a light stabilizer, a thickener, an adhesion improver, a matting agent, and the like. May be.
- the composition preferably contains a solvent.
- the solvent is preferably an organic solvent, more preferably a polar organic solvent, and more preferably a ketone solvent, an ester solvent, a carbonate solvent, a cyclic ether solvent, or an amide solvent.
- MEK methyl ethyl ketone
- MIBK methyl isobutyl ketone
- acetone diethyl ketone
- dipropyl ketone ethyl acetate, methyl acetate, propyl acetate, butyl acetate, ethyl lactate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate
- Methyl ethyl carbonate tetrahydrofuran, methyl tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide (DMAc), diacetone alcohol and the like.
- the amount of the component (A) relative to 100% by mass of the total composition is preferably 1 to 95% by mass, and more preferably 5 to 70% by mass.
- the above composition can be suitably used as a coating composition.
- the coating composition may contain the solvent or may not contain the solvent.
- the application temperature may be a normal temperature condition depending on the form of application.
- knife coating method, roll coating method, gravure coating method, blade coating method, reverse method, rod coating method, air doctor coating method, curtain coating method, fakunrun coating method, kiss coating method, screen coating method , Spin coating method, spray coating method, extrusion coating method, micro gravure coating method, flow coating method, bar coating method, die coating method, dip coating method, etc. can be adopted, the type of substrate, shape, productivity, film thickness It can be selected in consideration of controllability.
- the coating film may be cured and dried. Curing and drying are carried out at 10 to 300 ° C., usually 10 to 200 ° C., for 30 seconds to 3 days. After curing and drying, curing may be performed, and curing is usually completed at 10 to 200 ° C. for 1 minute to 3 days. In addition to heating, curing can be performed by a method of photocuring by irradiating active energy rays such as ultraviolet rays, electron beams or radiation.
- active energy rays such as ultraviolet rays, electron beams or radiation.
- the said composition can be utilized suitably as an adhesive agent.
- the composition can be suitably used as an adhesive used for adhesion of optical members because it can form a coating film having excellent corrosion prevention effect, transparency and adhesion. .
- it is excellent also in adhesion
- the composition is not limited to the adhesion of optical members, but can be suitably used as an adhesive.
- the composition can also be suitably used as a conductive paste, conductive ink, conductive paint, or electrode paste.
- the said composition contains the electroconductive substance mentioned later.
- the composition contains a conductive substance.
- the conductive substance include metals or organic conductive materials such as conductive particles, conductive fibers, conductive polymers, carbon nanotubes, graphene, and graphite, and are selected from the group consisting of conductive particles and conductive fibers. It is preferable that there is at least one.
- the conductive fiber examples include metal nanowires.
- the said metal nanowire means what has electroconductivity and a long-axis direction length is long enough compared with a diameter (short-axis direction length).
- the metal nanowire may be a solid fiber or a hollow fiber.
- At least one metal selected from the group consisting of at least one metal selected from the group consisting of the fourth period, the fifth period, and the sixth period, and at least one type selected from the group 2 to group 14 Metal is more preferred, at least one metal selected from the group consisting of the fourth period, the fifth period, and the sixth period, and the second group, the eighth group, the ninth group, the tenth group, the eleventh group, At least one metal selected from Group 12, Group 13, and Group 14 is more preferable, and it is particularly preferable that it is included as a main component.
- Examples of the metal include copper, silver, gold, platinum, palladium, nickel, tin, cobalt, rhodium, iridium, iron, ruthenium, osmium, manganese, molybdenum, tungsten, niobium, tantel, titanium, bismuth, antimony, and lead. And alloys thereof. Among these, silver and an alloy with silver are particularly preferable in terms of excellent conductivity. Examples of the metal used in the alloy with silver include platinum, osmium, palladium, iridium, tin, bismuth, and nickel. These may be used alone or in combination of two or more.
- the said metal nanowire can take arbitrary shapes, such as a column shape, a rectangular parallelepiped shape, and a column shape in which a cross section becomes a polygon.
- the columnar shape or the shape of a columnar polygon having a polygonal cross section is rounded.
- the cross-sectional shape of the metal nanowire can be examined by applying a metal nanowire aqueous dispersion on a substrate and observing a cross-section produced by a microtome with a transmission electron microscope (TEM).
- TEM transmission electron microscope
- Examples of the conductive particles include metal nanoparticles or metal particle sols.
- the metal nanoparticles are silver, copper, gold, zinc, cadmium, palladium, iridium, ruthenium, osmium, rhodium, platinum, iron, nickel, cobalt, indium, silver oxide, copper oxide, gold oxide, zinc oxide, cadmium oxide.
- the metal nanoparticle population can have individual nanoparticles, particle aggregates composed of two or more individual nanoparticles, particle floe composed of two or more individual nanoparticles, or any combination thereof.
- the ratio by weight of individual metal nanoparticles population to particle aggregates ranges from about 1:99 to 99: 1, and the ratio by weight of individual metal nanoparticles population to particle floc is generally about 1: It is in the range of 99 to 99: 1.
- substantially all of the nanoparticles are aggregates.
- substantially all of the nanoparticles are discrete individual nanoparticles.
- the metal nanoparticles may be a metal particle sol.
- the metal particle sol is preferably 0.1 to 10% by weight of silver nanoparticles and at least one metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum (the metal nanoparticles). In the form of metal and / or at least one metal compound.
- the silver nanoparticles in the metal particle sol are at least 80%, preferably at least 80% of the content of at least one metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum. It accounts for 90%.
- the metal particle sol contains only a small amount of metal nanoparticles or metal compound nanoparticles having no silver of this metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum.
- the metal particle sol is less than 20%, particularly preferably less than 10% of this metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum (represented by the content of this metal).
- this metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum (represented by the content of this metal).
- this metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum (represented by the content of this metal).
- this metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum (represented by the content of this metal).
- metal nanoparticles or metal compound nanoparticles without the silver of the metal without the silver of the metal.
- the obtained sheet is a pressure-sensitive adhesive sheet or an adhesive sheet used for bonding optical members. As such, it can be suitably used. Moreover, since it is excellent also in adhesion
- the obtained sheet can be suitably used not only for adhesion of the optical member but also as an adhesive sheet or an adhesive sheet.
- the metal examples include copper, silver, aluminum, iron, SUS, nickel, molybdenum, chromium, zinc, and other various steel plates.
- copper or silver is preferable because excellent metal adhesion and rust prevention are exhibited.
- copper is particularly preferable. Therefore, the composition 3 is more suitable as a copper or silver anticorrosive coating composition.
- Copper is not limited to a copper plate, but may be copper deposited or sputtered on a substrate, or copper foil laminated on a substrate.
- Silver is not limited to a silver plate, but may be one in which silver is vapor-deposited or sputtered on a base material, or silver foil laminated on a base material.
- the composition includes various conductive materials such as printed circuit boards, conductive parts of multilayer boards, connector electrodes, silver or copper patterns, conductive films of silver or copper mesh, fine metal particles such as silver or copper, and conductive films made of metal nanowires. Since it is possible to suppress the occurrence of migration with respect to the part, it is also suitable as a coating composition for suppressing the occurrence of migration.
- compositions include touch panels, LEDs, solar cells, organic EL, electronic devices used outdoors, wiring of other electronic devices, electric wires, electrical contacts, electronic devices, antennas, protection of metal parts of elements. It is done. More specifically, protection of the touch panel take-out wiring, protection of the touch panel transparent electrode, protection of the LED lead frame, and protection of the solar battery take-out wiring made of copper or silver can be mentioned.
- a coated article comprising a substrate and a coating film formed on the substrate from the composition is also useful.
- the base material is a metal, a resin in which the metal is dispersed or partially dispersed, a metal / resin laminate in which the entire or part of the resin surface is covered with metal, glass, polyethylene terephthalate, cycloolefin polymer, polyimide polymer, It is preferably formed from a urethane polymer, an acrylic polymer, or a mixed polymer of a urethane polymer and an acrylic polymer, and a resin in which a metal is dispersed or partially dispersed, or the resin surface is entirely or partially covered with metal. It is more preferable to use a metal / resin laminate.
- the metal include copper, silver, aluminum, iron, SUS, nickel, molybdenum, chromium, and zinc. In particular, copper or silver is preferable because an excellent corrosion prevention effect and adhesion are exhibited. Furthermore, copper is particularly preferable.
- Examples of the coated article include touch panels, LEDs, solar cells, organic EL, electronic devices used outdoors, metal wiring of other electronic devices, electronic devices, antennas, elements, and the like. More specifically, a touch panel extraction wiring, a touch panel transparent electrode, an LED lead frame, a solar cell extraction wiring, and the like made of copper or silver are exemplified.
- the present invention is also a molded article characterized by being formed from the above composition.
- the present invention is also a sheet formed from the above composition.
- seat can be manufactured by apply
- Curing and drying are carried out at 10 to 300 ° C., usually 10 to 200 ° C., for 30 seconds to 3 days. After curing and drying, curing may be performed, and curing is usually completed at 10 to 200 ° C. for 1 minute to 3 days. In addition to heating, curing can be performed by a method of photocuring by irradiating active energy rays such as ultraviolet rays, electron beams or radiation.
- active energy rays such as ultraviolet rays, electron beams or radiation.
- the sheet can be attached to another layer by being pressure-bonded after being placed on the other layer or between the other two layers.
- a laminated sheet comprising a release sheet and a sheet formed on the release sheet from the composition is also useful.
- the release sheet may be provided on one side of the coating film, or may be provided on both sides of the coating film.
- the said laminated sheet can be manufactured by apply
- the conditions for drying and curing are as described above.
- the release sheet a sheet obtained by applying a release agent to a substrate, a fluororesin sheet, or the like can be used.
- the base material include those made of a polyester resin such as polyethylene terephthalate.
- the release agent include silicone-based, fluoro-based, fluorosilicone-based, and olefin-based, alkyd-based, alkyl-based, long-chain not containing silicone. Mention may be made of alkyl systems.
- the said laminated sheet can be used by peeling a peeling sheet at the time of use, and bonding the sheet
- the sheet formed from the composition is highly effective in preventing metal corrosion, has excellent adhesion to metal, and is excellent in transparency. Furthermore, the sheet can also suppress the occurrence of migration of various conductive parts such as printed circuit boards, conductive parts of multilayer boards, connector electrodes, silver or copper patterns, silver or copper mesh conductive films.
- the present invention relates to an epoxy polymer, a silicone polymer, a urethane polymer, an acrylic polymer, an ethylene-vinyl acetate polymer, a butadiene polymer, a cellulose polymer, a monomer that provides an epoxy polymer, a monomer that provides a silicone polymer, a monomer that provides a urethane polymer, and an acrylic polymer It is also a sheet characterized in that it is formed from at least one component (A) selected from the group consisting of monomers that give a b * value of 0.8 or less and Haze is less than 1% .
- A component selected from the group consisting of monomers that give a b * value of 0.8 or less and Haze is less than 1% .
- Component (A) is preferably at least one selected from the group consisting of an epoxy polymer, a monomer that provides an epoxy polymer, an acrylic polymer, a monomer that provides an acrylic polymer, a silicone polymer, and a monomer that provides a silicone polymer, More preferably, it is at least one selected from the group consisting of an epoxy polymer, a monomer that provides an epoxy polymer, an acrylic polymer, and a monomer that provides an acrylic polymer.
- the b * value is preferably 0.7 or less, and the lower limit is not particularly limited, but may be 0.1.
- the b * value can be measured using a color difference meter (CR-400, manufactured by KONIKA MINOLTA).
- the Haze is preferably 0.5% or less, and the lower limit is not particularly limited, but may be 0.1.
- the Haze can be measured using a Haze meter (HazeGard II manufactured by Toyo Seiki Seisakusho).
- seat can be suitably manufactured from the composition containing the nitrogen-containing aromatic heterocyclic compound mentioned above and a component (A).
- seat (coating film) can be manufactured by apply
- a laminate having the laminated structure shown in FIGS. 1 and 2 can be produced using the above-described composition, and the above-described sheet and laminated sheet.
- seat 12 formed from the said composition, the metal layer 13, and the insulating layer 14 are provided in this order.
- seat formed from the said composition is used as an optically transparent adhesive sheet (OCA sheet). That is, the sheet 12 firmly bonds the insulating layer 11 and the metal layer 13 and at the same time protects the metal layer 13 from corrosion.
- the insulating layers 11 and 14 are preferably transparent substrates, and can be formed from glass, polyethylene terephthalate, cycloolefin polymer, polyimide polymer, urethane polymer, acrylic polymer, or a mixed polymer of urethane polymer and acrylic polymer. .
- the metal layer 13 can be formed from copper, silver, aluminum, iron, SUS, nickel, molybdenum, chromium, zinc or the like, and among these, it is preferable to form from copper or silver.
- FIG. The primer layer may be a sheet formed from the above composition.
- the insulating layer 21, the sheet 22 formed from the above composition, the metal layer 23, the insulating layer 24, the metal layer 25, and the sheet 26 formed from the above composition are provided in this order. .
- seat formed from the said composition is used as an optically transparent adhesive sheet (OCA sheet). That is, the sheets 22 and 26 firmly bond the insulating layer 21 and the metal layer 23, and at the same time, protect the metal layers 23 and 25 from corrosion. Further, it can be bonded to another optical member via the sheet 26.
- OCA sheet optically transparent adhesive sheet
- the insulating layers 21 and 24 are preferably transparent substrates and can be formed from glass, polyethylene terephthalate, cycloolefin polymer, polyimide polymer, urethane polymer, acrylic polymer, or a mixed polymer of urethane polymer and acrylic polymer. .
- the metal layers 23 and 25 can be formed from copper, silver, aluminum, iron, SUS, nickel, molybdenum, chromium, zinc or the like, and among these, it is preferable to form from copper or silver. You may provide the primer layer which improves adhesiveness in the single side
- the primer layer may be a sheet formed from the composition of the present invention.
- the “sheet formed from the composition” in each of the embodiments described above may be a “coating film formed from the composition 2”.
- Example 1 and Comparative Examples 1 and 2 were coated on a polyethylene terephthalate (PET) film (Toray, Lumirror U-46 100 ⁇ m) with a bar coat No.
- PET polyethylene terephthalate
- Example 1 and Comparative Examples 1 and 2 were dried at 70 ° C. for 20 minutes, and Example 2 was post-cured at 60 ° C. for 1 hour and then irradiated with UV (Ushio Electric Co., Ltd., conditions; integration Light amount: 10,000 mJ / cm 2 ), a cured coating film was obtained.
- the coating solution obtained in Example 3 was coated on a PET film (Toray, Lumirror U-46 100 ⁇ m) with a bar coat No.
- UV was irradiated (conditions manufactured by Ushio Inc .; integrated light quantity: 615 mJ / cm 2 ) to obtain a cured coating film.
- b * value was measured using a color difference meter (CR-400 manufactured by KONIKA MINOLTA).
- the b * value of the coating film was obtained by subtracting the total b * value of the hiding test paper (manufactured by Nippon Test Panel Co., Ltd.) measured in the background and the PET film not coated.
- the Haze of the coating film was measured using a Haze meter (HazeGard II manufactured by Toyo Seiki Seisakusho).
- Example 1 and Comparative Examples 1 and 2 were subjected to bar coating No. 1 on the copper deposition surface of a film in which copper was deposited on PET.
- Example 1 and Comparative Examples 1 and 2 were dried at 70 ° C. for 20 minutes, and Example 2 was post-cured at 60 ° C. for 1 hour and then irradiated with UV (Ushio Electric Co., Ltd., conditions; integration Light quantity: 10,000 mJ / cm 2 ) and cured to obtain a laminate of coating film / copper / PET.
- the coating liquid obtained in Example 3 was applied to the bar coating No. 1 on the copper deposition surface of the film in which copper was deposited on PET. After coating at 10 and drying at 70 ° C.
- the dried coating film was irradiated with UV (Ushio Electric Co., Ltd .; condition: integrated light quantity: 615 mJ / cm 2 ), and a cured coating film / copper / PET laminate Got.
- UV Ushio Electric Co., Ltd .; condition: integrated light quantity: 615 mJ / cm 2
- a cured coating film / copper / PET laminate Got For each film formed on the copper vapor deposition surface of the film in which copper was vapor deposited on PET, the number of squares that were able to maintain close contact among 100 squares was examined according to JIS K5600 by a cross-cut tape method. . Of 100 squares, 70 or more squares were not peeled off and the coating film was in close contact, and those with no peeling and close contact were less than 70 squares.
- UV Ushio Electric Co., Ltd., conditions; integrated light quantity: 10000 mJ / cm 2
- Synthesis example 1 Compound a (used in Examples 1-5) In a 30 ml eggplant flask, 0.5 g of 1,2,3-benzotriazole and 10 g of acetone were weighed and stirred at room temperature for 30 minutes to dissolve 1,2,3-benzotriazole, and then acryloyloxyethyl isocyanate (Showa Denko) 0.59 g (1 equivalent to 1,2,3-benzotriazole) was added dropwise. After stirring at room temperature for 4 hours, 0.1 g of the reaction solution was dropped on a KBr plate and measured with an FT-IR (Fourier transform infrared spectrophotometer Perkin Elmer Japan Perkin Elmer Precision Spectrum 100 FT-IR Spectrometer). It was confirmed that no isocyanate group derived from acryloyloxyethyl isocyanate remained.
- FT-IR Fastier transform infrared spectrophotometer Perkin Elmer Japan Perkin Elmer Precision Spectrum 100 FT-IR Spect
- Synthesis example 2 Compound b (used in Comparative Example 1) The compound was synthesized in the same manner as in Synthesis Example 1 except that 1-hydroxy-1H-benzotriazole was used instead of 1,2,3-benzotriazole.
- Example 1 Compound a obtained in Synthesis Example 1 was added to the resin component polymethyl methacrylate (PMMA) (manufactured by Mitsubishi Rayon Co., Ltd.) so as to be 5% by mass, dissolved in 1/1 solvent of butyl acetate and methyl ethyl ketone, The total solid content was adjusted to 30% by mass to obtain a coating solution.
- PMMA polymethyl methacrylate
- Example 2 70 parts by mass of Epicoat 828 (Ebisphenol A type epoxy resin, manufactured by Mitsubishi Chemical Corporation), 28 parts by mass of Denacol EX-212 (1,6-hexanediol diglycidyl ether, manufactured by Nagase Chemtech Co., Ltd.), SP150 (photocationic curing) 2 parts by mass of a catalyst (manufactured by Adeka Industry Co., Ltd.) was mixed to obtain an epoxy composition. To the total amount of the epoxy composition obtained, compound a obtained in Synthesis Example 1 was added so as to be 5% by mass, dissolved in 1/1 solvent of butyl acetate and methyl ethyl ketone, and the total solid content was 30% by mass. The coating liquid was obtained.
- Epicoat 828 Bisphenol A type epoxy resin, manufactured by Mitsubishi Chemical Corporation
- Denacol EX-212 (1,6-hexanediol diglycidyl ether, manufactured by Nagase Chemtech Co., Ltd.
- SP150 photocationic
- Example 3 Compound a obtained in Synthesis Example 1 is added to 5% by mass with respect to dipentaerythritol hexaacrylate and dissolved in 1/1 solvent of butyl acetate and methyl ethyl ketone so that the total solid content becomes 30% by mass. To obtain a composition. Thereafter, Irgacure 184 (manufactured by BASF) is added to the composition so that the solid content in the composition (excluding butyl acetate and methyl ethyl ketone as solvents) is 3% by mass, and the coating liquid is Prepared.
- Irgacure 184 manufactured by BASF
- Example 4 Preparation of Conductive Paste Silver having an average particle size of about 0.08 ⁇ m so as to be 80% by mass with respect to the solid content of the coating liquid obtained in Example 2 (excluding butyl acetate and methyl ethyl ketone as solvents) Particles were added and stirred for 24 hours to create a silver paste.
- the obtained silver paste was applied onto a PET film with a bar coat # 10, post-cured at 60 ° C. for 1 hour, and then irradiated with UV (Ushio Denki Co., Ltd .; conditions; integrated light quantity: 10,000 mJ / cm 2 ).
- a layer containing particles / PET laminate was prepared.
- Example 5 Preparation of optical adhesive In a 250 mL eggplant flask, 25 parts by mass of 2-ethylhexyl acrylate, 30 parts by mass of acrylic acid-n-butyl ester, 30 parts by mass of 2-hydroxyethyl acrylate, acrylic acid 10 parts by mass of methyl, 5 parts by mass of compound a prepared in Synthesis Example 1, 150 parts by mass of ethyl acetate, 0.15 parts by mass of azobisisobutyronitrile (AIBN) as a polymerization initiator were added, Stir at 6 ° C. for 6 hours. Ethyl acetate was added to the resulting solution to adjust the polymer solid content concentration to 20% by mass.
- AIBN azobisisobutyronitrile
- Coronate L manufactured by Nippon Polyurethane Industry Co., Ltd.
- the coating solution contained 4.9% by mass of compound a based on the solid content.
- the obtained coating solution is applied to a release agent surface of a release sheet made of PET (GS38, manufactured by Lintec Corporation) with a silicone release agent on one side, dried at 80 ° C. for 3 minutes, and then released.
- a laminated sheet comprising a sheet / adhesive sheet was obtained. Thereafter, the adhesive sheet surface of the above laminated sheet is bonded to the copper vapor deposition surface of a film in which copper is deposited on PET having a film thickness of 100 ⁇ m, and a four-layer laminate of release sheet / adhesive sheet / copper vapor deposition layer / PET. was made.
- Comparative Example 1 Compound b prepared in Synthesis Example 2 is added to the resin component PMMA (manufactured by Mitsubishi Rayon Co., Ltd.) so as to be 5% by mass so that the total solid content becomes 30% by mass in 1/1 solvent of butyl acetate and methyl ethyl ketone. To obtain a coating solution.
- PMMA manufactured by Mitsubishi Rayon Co., Ltd.
- Comparative Example 2 RUVA-93 (manufactured by Otsuka Chemical Co., Ltd.) is added to the resin component PMMA (manufactured by Mitsubishi Rayon Co., Ltd.) so as to be 5% by mass, and the total solid content becomes 30% by mass in 1/1 solvent of butyl acetate and methyl ethyl ketone. Thus, a coating solution was obtained.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
Abstract
L'invention concerne une composition à partir de laquelle un film de revêtement présentant une excellente adhérence et une excellente transparence peut être formé. Cette composition contient un composé hétérocyclique aromatique contenant de l'azote, et un composé (A) représenté par la formule générale (1).
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JP2008274216A (ja) * | 2007-03-30 | 2008-11-13 | Fujifilm Corp | 重合性化合物、重合体、インク組成物、印刷物及びインクジェット記録方法 |
JP2010134137A (ja) * | 2008-12-04 | 2010-06-17 | Fujifilm Corp | カラーフィルタ及びその製造方法、並びに液晶表示装置 |
JP2013068814A (ja) * | 2011-09-22 | 2013-04-18 | Fujifilm Corp | 着色感放射線性組成物、カラーフィルタ及びそのカラーフィルタの製造方法、並びに、固体撮像素子 |
JP2014108986A (ja) * | 2012-12-03 | 2014-06-12 | Fujifilm Corp | 分散組成物、感光性樹脂組成物、硬化物及びその製造方法、樹脂パターン製造方法、硬化膜、有機el表示装置、液晶表示装置、並びに、タッチパネル表示装置 |
WO2015016330A1 (fr) * | 2013-08-02 | 2015-02-05 | ダイキン工業株式会社 | Nouveau composé ayant un groupe insaturé, et composition comprenant ledit composé |
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JP2008274216A (ja) * | 2007-03-30 | 2008-11-13 | Fujifilm Corp | 重合性化合物、重合体、インク組成物、印刷物及びインクジェット記録方法 |
JP2010134137A (ja) * | 2008-12-04 | 2010-06-17 | Fujifilm Corp | カラーフィルタ及びその製造方法、並びに液晶表示装置 |
JP2013068814A (ja) * | 2011-09-22 | 2013-04-18 | Fujifilm Corp | 着色感放射線性組成物、カラーフィルタ及びそのカラーフィルタの製造方法、並びに、固体撮像素子 |
JP2014108986A (ja) * | 2012-12-03 | 2014-06-12 | Fujifilm Corp | 分散組成物、感光性樹脂組成物、硬化物及びその製造方法、樹脂パターン製造方法、硬化膜、有機el表示装置、液晶表示装置、並びに、タッチパネル表示装置 |
WO2015016330A1 (fr) * | 2013-08-02 | 2015-02-05 | ダイキン工業株式会社 | Nouveau composé ayant un groupe insaturé, et composition comprenant ledit composé |
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CN111601867A (zh) * | 2018-01-17 | 2020-08-28 | 日立化成株式会社 | 粘接剂组合物、连接结构体及其制造方法 |
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