JP6855655B2 - アクリル系ポリマー及びそれを含有する帯電防止剤、帯電防止性樹脂組成物 - Google Patents
アクリル系ポリマー及びそれを含有する帯電防止剤、帯電防止性樹脂組成物 Download PDFInfo
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- JP6855655B2 JP6855655B2 JP2016097012A JP2016097012A JP6855655B2 JP 6855655 B2 JP6855655 B2 JP 6855655B2 JP 2016097012 A JP2016097012 A JP 2016097012A JP 2016097012 A JP2016097012 A JP 2016097012A JP 6855655 B2 JP6855655 B2 JP 6855655B2
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- acrylic polymer
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- 239000000203 mixture Substances 0.000 claims description 46
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- 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 6
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- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 5
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- 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 4
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
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- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- PAZHGORSDKKUPI-UHFFFAOYSA-N lithium metasilicate Chemical compound [Li+].[Li+].[O-][Si]([O-])=O PAZHGORSDKKUPI-UHFFFAOYSA-N 0.000 description 1
- 229910052912 lithium silicate Inorganic materials 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical class NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FIBUWQFQYAAXHD-UHFFFAOYSA-N n-cyclopropyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1CC1 FIBUWQFQYAAXHD-UHFFFAOYSA-N 0.000 description 1
- RGNKVBUBMHKKJP-UHFFFAOYSA-N n-methyl-n-propylprop-2-enamide Chemical compound CCCN(C)C(=O)C=C RGNKVBUBMHKKJP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Polarising Elements (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Adhesive Tapes (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
さらに、本発明は、長期保存下においても、帯電防止性能と粘着力が劣化しない、透明な帯電防止粘着剤を提供することを課題とする。
(1)以下の(A)〜(C)に相当する構成単位を含有することを特徴とするアクリル系ポリマー。
(A)2−(メタ)アクリロイルオキシアルキルフタル酸(a)が金属カチオンを含む塩基性物質によって中和された塩
(B)一般式(1)で表されるアルキレンオキシド基含有モノマー(b)
(C)モノマー(a)及びモノマー(b)と共重合可能な炭素数6〜18のアルキル基を有するアルキル(メタ)アクリルモノマー(c)
(2)アクリル系ポリマーを構成するモノマーのモル比が、(a)/(b)/(c)=5〜70/10〜70/5〜70であることを特徴とする前記(1)に記載のアクリル系ポリマー、
(3)カルボキシル基含有モノマー(d)が金属カチオンを含む塩基性物質によって中和された塩1〜70モル%を構成成分としてさらに含有することを特徴とする前記(1)又は(2)に記載のアクリル系ポリマー、
(4)(メタ)アクリルアミド系モノマー(e)((b)を除く)0.05〜10モル%を構成成分としてさらに含有することを特徴とする前記(1)〜(3)のいずれか一項に記載のアクリル系ポリマー、
(5)金属カチオンはリチウムイオン、ナトリウムイオン、カリウムイオンから選ばれる1種又は2種以上の金属カチオンであることを特徴とする前記(1)〜(4)のいずれか一項に記載のアクリル系ポリマー、
(6)前記(1)〜(5)のいずれかの項に記載のアクリル系ポリマーを0.1質量%以上含有することを特徴とする帯電防止剤、
(7)前記(1)〜(5)のいずれか一項に記載のアクリル系ポリマーを0.1質量%以上含有することを特徴とする帯電防止性コーティング組成物、
(8)前記(1)〜(5)のいずれか一項に記載のアクリル系ポリマーを0.1質量%以上含有することを特徴とする帯電防止性粘着剤用アクリル樹脂組成物、
(9)前記(1)〜(5)のいずれか一項に記載のアクリル系ポリマーを0.1質量%以上含有し、さらに不飽和基含有化合物(f)及び重合開始剤(g)を含有し、活性エネルギー線により架橋されてなることを特徴とする帯電防止性粘着剤組成物、
(10)前記(1)〜(5)のいずれか一項に記載のアクリル系ポリマーを0.1質量%以上含有し、さらに架橋剤(h)を含有し、架橋剤(h)により架橋されてなることを特徴とする帯電防止性粘着剤組成物、
(11)シート状の支持体の少なくとも片面に、前記(9)又は(10)に記載の粘着剤組成物を含有する粘着層が形成されてなる粘着シート、
(12)樹脂フィルムに、前記(9)又は(10)に記載の粘着剤組成物を含有する粘着層が形成されてなる光学部材用表面保護フィルム、
(13)偏光フィルムからなる支持体の少なくとも片面に、前記(9)又は(10)に記載の粘着剤組成物を含有する粘着層が形成されてなる偏光板
を提供するものである。
本発明のアクリル系ポリマーは、2−(メタ)アクリロイルオキシアルキルフタル酸(a)が金属カチオンを含む塩基性物質によって中和された塩に相当する構成単位と、アルキレンオキシド基含有モノマー(b)に相当する構成単位と、モノマー(a)及びモノマー(b)と共重合可能な炭素数6〜18のアルキル基を有するアルキル(メタ)アクリルモノマー(c)に相当する構成単位を含有することを特徴とするものである。アクリル系ポリマー中でフタル酸アニオン基が固定されることにより、金属カチオンのみが自由に移動することができるため、優れた帯電防止性能を発現することができる。
具体的には、アルコキシポリアルキレングリコール(メタ)アクリレート、アルコキシポリアルキレングリコール(メタ)アクリルアミド、アルコキシアルキル(メタ)アクリレート、アルコキシアルキル(メタ)アクリルアミドが挙げられ、これらの中でも、メトキシポリエチレングリコール(メタ)アクリレート、メトキシポリプロピレングリコール(メタ)アクリレート、メトキシポリエチレングリコール(メタ)アクリルアミド、メトキシポリプロピレングリコール(メタ)アクリルアミド、メトキシメチル(メタ)アクリレート、エトキシメチル(メタ)アクリレート、メトキシエチル(メタ)アクリレート、エトキシエチル(メタ)アクリレート、エトキシプロピル(メタ)アクリレート、メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、メトキシエチル(メタ)アクリルアミド、エトキシエチル(メタ)アクリルアミド、エトキシプロピル(メタ)アクリルアミドが好ましい。特に、メトキシポリエチレングリコール(メタ)アクリレートがイオン対との相溶性に優れるため、より好ましい。これらは1種類に限らず、複数の種類を組み合わせて使用してもよい。
(1)重量平均分子量(Mw)の測定
GPC測定装置((株)島津製作所製の Prominence)を用い、示差屈折計(RI計)を検出器として、以下の条件で測定した。なお、重量平均分子量は、標準ポリスチレン分子量換算により算出した。
・カラム:昭和電工社製 Shodex Asahipak GF−510HQ
・移動相:テトラヒドロフラン
・流速:0.5mL/min
・測定温度:40℃
(2)酸価測定
アクリル系ポリマーを溶剤(アセトンと水を体積比7:1に混合したもの)に溶かし、電位差自動滴定装置(京都電子工業製 AT−610)を用いて0.5mol/L水酸化カリウム・エタノール溶液を用いて滴定を行い、アクリル系ポリマー1gを中和するのに必要な水酸化カリウムの量を測定した。次いで、下記式により、酸価を求めた。
酸価(mgKOH/g)= (A x f x C)/S
A:滴定量(mL)
f:滴定液のファクター
C:濃度換算値(0.5mol/Lx56.11=28.055mg/mL)
S:試料採取量(g)
(3)溶解性
アクリル系ポリマーを、メチルエチルケトン(MEK)、アクリル酸ブチル(BA)及びアクリル酸2−エチルヘキシル(2EHA)に溶解し、溶解性を目視によって観察した。
◎:10(g/100g)以上
○:5(g/100g)以上10(g/100g)未満
△:1(g/100g)以上5(g/100g)未満
×:1(g/100g)未満
(4)帯電防止性コーティング組成物(コーティング膜)の作製
厚さ100μmのポリエチレンテレフタラート(PET)フィルムに、乾燥後の厚みが20μmとなるよう、帯電防止性コーティング組成物の溶液を塗布し、120℃で2分間乾燥させて、コーティング層を形成した。次いで、コーティング層塗布面を上向きにして紫外線照射を行って架橋させ、試験用コーティング膜を得た。紫外線照射条件は、紫外線照射装置(アイグラフィックス製 インバーター式コンベア装置ECS−4011GX、メタルハライドランプ:アイグラフィックス製 M04−L41)を使用し、紫外線照度:700mW/cm2、積算光量:1000mJ/cm2になるように試料板とランプの距離を調節した。その後、温度23℃、相対湿度50%の環境に1日置き、試験用コーティング膜を得た。
(5)コーティング膜の物性評価
コーティング膜の評価は、1)透明性、2)表面抵抗率測定、3)耐擦傷性試験、4)耐湿性試験、5)鉛筆硬度試験、により行った。
1)透明性
◎:透明で表面が平滑;
○:透明だが凹凸がある;
△:僅かな曇りや凹凸がある;
×:極度な曇りや凹凸がある
2)表面抵抗率測定
型板 (縦110×横110mm) を用い、カッターナイフでコーティング膜を裁断し、表面抵抗率測定用試料を得た。JIS K 6911 に基づき、デジタルエレクトロメーター(R8252型:エーディーシー社製)を用いて表面抵抗値を測定した。
3)耐擦傷性試験
スチールウールを#0000のスチールウールを用いて、200g/cm2の荷重をかけながらコーティング膜の上で10往復させ、傷の発生の有無を評価した。
◎:膜の剥離や傷の発生がほとんど認められない;
○:膜に僅かな細い傷が認められる;
△:膜全面に筋状の傷が認められる;
×:膜の剥離が生じる。
4)耐湿性試験
コーティング膜を40℃、90%RHの恒温槽内にて3日間保管し、膜の外観の変化を目視で評価した。
◎:外観に変化がない;
○:白化などの外観変化が僅かに認められるが問題のないレベル;
△:白化などの外観変化が僅かに認められる;
×:白化などの外観変化が著しく認められる;
5)鉛筆硬度試験
コーティング膜について、JIS K 5400 に基づき、鉛筆硬度試験を行った。
(6)粘着シートの作製
厚さ100μmのポリエチレンテレフタラート(PET)フィルムに、乾燥後の厚みが20μmとなるよう、粘帯電防止性粘着剤組成物溶液を塗布し、120℃で2分間乾燥させて、粘着剤層を形成した。次いで、
1)架橋剤を用いて架橋する場合は、40℃の恒温槽で3日間エージングさせた後、温度23℃、相対湿度50%の環境に1日置き、試験用粘着シート(タイプ1)を得た。
2)紫外線照射により架橋する場合は、以下(7)の紫外線硬化方法により、紫外線硬化膜を得、その後、温度23℃、相対湿度50%の環境に1日置き、試験用粘着シート(タイプ2)を得た。
(7)紫外線硬化
粘着剤塗布面を上向きにして紫外線照射を行って架橋させ、試験用粘着シートを得た。紫外線照射条件は、紫外線照射装置(アイグラフィックス製 インバーター式コンベア装置ECS−4011GX、メタルハライドランプ:アイグラフィックス製 M04−L41)を使用し、紫外線照度:700mW/cm2、積算光量:1000mJ/cm2になるように試料板とランプの距離を調節した。
(8)粘着シートの物性評価
粘着シートの評価は、1)表面抵抗率測定、2)粘着力、3)透明性、4)被着体汚染性、5)経時安定性試験、により行った。
1)表面抵抗率測定
型板 (縦110×横110mm) を用い、カッターナイフで粘着シートを裁断し、表面抵抗率測定用試料を得た。JIS K 6911 に基づき、デジタルエレクトロメーター(R8252型:エーディーシー社製)を用いて表面抵抗値を測定した。
2)粘着力
温度23℃、相対湿度50%の条件下、被着体として鏡面処理されたステンレス板(SUS304)に、25mm幅に裁断した粘着シートの粘着剤塗布面を重さ2kgの圧着ローラを用いて2往復することにより加圧貼付し、同雰囲気下で30分間放置した。その後、引っ張り試験機(装置名:テンシロンRTA−100 ORIENTEC社製)を用いて、剥離速度300mm/分にて180°剥離強度(N/25mm)を測定した。
3)透明性
粘着シートの透明性を目視によって観察した。
◎:透明で表面が平滑;
○:透明だが凹凸がある;
△:僅かな曇りや凹凸がある;
×:極度な曇りや凹凸がある;
4)被着体汚染性
粘着シートを前述の粘着力の測定と同様に被着体に貼り付け、80℃、24時間放置した後、粘着シートを剥がした後の被着体表面の汚染を目視によって観察した。
◎:汚染なし;
○:ごく僅かに汚染がある;
△:僅かに汚染がある;
×:糊(粘着剤)残りがある;
5)経時安定性試験
前記(6)の(1)、(2)の方法により作製した粘着シートを、温度23℃、相対湿度50%の環境に4週間放置後、(8)− 1)〜4)の方法にて帯電防止組成物の特性評価を行った。
AEF:2−アクリロイルオキシエチルフタル酸(共栄社化学社製 ライトアクリレートHOA−MPL(N))
APF:2−アクリロイルオキシプロピルフタル酸(大阪有機化学工業社製 ビスコート#2100)
AM90G:メトキシポリエチレングリコール#400アクリレート (新中村化学工業社製 NKエステルAM−90G)
AM130G:メトキシポリエチレングリコール#550アクリレート (新中村化学工業社製 NKエステルAM−130G)
M230G:メトキシポリエチレングリコール#1000メタクリレート(新中村化学工業社製 NKエステルM−230G)
AE−400:ポリエチレングリコールモノアクリレート(日油社製 ブレンマーAE−400)
PLE−1300:ラウロキシ-ポリエチレングリコール-メタクリレート(日油社製 ブレンマーPLE−1300)
EPAA:3−エトキシプロピルアクリルアミド(KJケミカルズ社製)
HEAA:N−ヒドロキシエチルアクリルアミド(KJケミカルズ社製 HEAA)
LA:ラウリルアクリレート(大阪有機化学工業社製LA)
IOA:イソオクチルアクリレート(大阪有機化学工業社製IOAA)
STA:ステアリルアクリレート(大阪有機化学工業社製STA)
HMA:ヘキシルメタクリレート(東京化成工業社製)
LMA:ラウリルメタクリレート(東京化成工業社製)
AAc:アクリル酸(東京化成工業社製)
MAAc:メタクリル酸(東京化成工業社製)
AES:2−アクリロイルオキシエチルコハク酸(共栄社化学社製 ライトアクリレートHOA−MS(N))
ACMO:アクリロイルモルホリン(KJケミカルズ社製 ACMO)
DEAA:N,N−ジエチルアクリルアミド (KJケミカルズ社製 DEAA)
PETA:ペンタエリスリトールトリアクリレート(共栄社化学社製 ライトアクリレートPE−3A)
DPHA:ジペンタエリスリトールヘキサアクリレート(新中村化学工業社製 A−DPH)
2EHA:2−エチルヘキシルアクリレート(東京化成工業社製)
2HEA:2−ヒドロキシエチルアクリレート(東京化成工業社製)
4HBA:4−ヒドロキシブチルアクリレート(東京化成工業社製)
BA:n−ブチルアクリレート(東京化成工業社製)
MEK:メチルエチルケトン(東京化成工業社製)
合成例イ−1(アクリル系ポリマー(1)の合成)
温度計、撹拌機、還流冷却器及び窒素導入管を備えた反応装置内に、AEF 29.1質量部、AM90G 100質量部、LA 52.9質量部、及びアゾイソブチロニトリル(AIBN)1.4質量部を1−メトキシ−2−プロパノール(PGME)226質量部に混合溶解し、窒素気流下90℃で13時間反応させ、共重合体(P−1)の溶液を得た。反応終了後、水酸化リチウムの2%メタノール溶液を50.3質量部(AEFに対して1モル倍)滴下し、1時間撹拌した後、減圧法により溶剤を除去し、透明な粘調体として、アクリル系ポリマー(1)を得た。酸価測定の結果、0.1mgKOH/gであった。また、赤外吸収スペクトル(IR)により分析を行い、ビニル基由来の二重結合の特有吸収(1620cm−1)が完全に消失したことにより、目的のアクリル系ポリマー(1)の生成を確認した。
表1(表1−1、表1−2)及び表2に示す単量体組成に変更する以外は、合成例イ−1と同様にしてアクリル系ポリマー(2〜18、19〜25)を得た。
実施例A−1
合成例イ−1で作製したアクリル系ポリマー(1)50質量部をメチルエチルケトン(MEK)120質量部に溶解したのち、不飽和基含有化合物としてペンタエリスリトールトリアクリレート(PETA)50質量部、光開始剤として、Darocure1173(BASF社製)3質量部を加え、均一に混合し、紫外線硬化可能な帯電防止性コーティング組成物溶液を得た。この帯電防止性コーティング組成物溶液を用い、前記の帯電防止性コーティング組成物の作成方法に従ってコーティング膜を作製し、前記の各種物性試験を行った。得られた結果を表3に示す。
実施例A−1と同様に帯電防止性コーティング組成物を作製し、前記の試験方法で各種物性を測定した。得られた結果を表3及び表4に示す。
製造例ハ−1
温度計、撹拌機、還流冷却器及び窒素導入管を備えた反応装置内に、酢酸エチル156質量部、2−エチルヘキシルアクリレート100質量部、2−ヒドロキシエチルアクリレート4質量部を加え、撹拌しながら窒素ガスを導入して装置内の空気を窒素に置換した後、アゾビスイソブチロニトリル(AIBN)0.4部を加え、還流温度まで昇温し、7時間反応させた。反応終了後、酢酸エチルで希釈して、粘着剤ベースポリマー(ハ−1)の35%溶液[固形分35%、粘度3500mPa・s(25℃)]を得た。
表5に示す単量体組成に変更する以外は、製造例ハ−1と同様にしてアクリル系粘着剤ベースポリマー(ハ−2〜5)を得た。
実施例B−1
粘着剤ベースポリマー(ハ−1)100質量部とアクリル系ポリマー(1)2質量部及び架橋剤としてトリレンジイソシアネート(TDI)2質量部を混合し、固形分濃度が20%となるようメチルエチルケトン(MEK)を加え、十分に撹拌して帯電防止粘着剤を得た。この帯電防止粘着剤を用い、前記の粘着シートの作製方法(1)に従って帯電防止粘着シート(タイプ1)を作製し、前記の各種物性試験を行った。得られた結果を表6に示す。
実施例1と同様に帯電防止粘着シートを作製し、前記の試験方法で各種物性を測定した。得られた結果を表6及び表7に示す。
合成例イ−1で作成したアクリル系ポリマー(1)3質量部を酢酸エチル50質量部に溶解したのち、製造例ハ−1で得た粘着剤ベースポリマー100質量部、不飽和基含有化合物としてジペンタエリスリトールヘキサアクリレート(DPHA)15質量部、及び光開始剤として、Darocure1173(BASF社製) 2部を加え、均一に混合し、紫外線硬化可能な帯電防止性粘着剤組成物溶液を得た。この粘着剤組成物溶液を用い、前記の粘着シートの作製方法(2)に従い、塗膜及び紫外線照射を行い、粘着シート(タイプ2)を作製し、前記の各種物性試験を行った。得られた結果を表8に示す。
実施例C−1と同様に粘着シート(タイプ2)を作製し、前記の試験方法で各物性を測定した。得られた結果を表8及び表9に示す。
Claims (13)
- 以下の(A)〜(C)に相当する構成単位を含有することを特徴とするアクリル系ポリマー。
(A)2−(メタ)アクリロイルオキシアルキルフタル酸(a)が金属カチオンを含む塩基性物質によって中和された塩
(B)化1で表されるアルキレンオキシド基含有モノマー(b)
(C)モノマー(a)及びモノマー(b)と共重合可能な炭素数6〜18のアルキル基を有するアルキル(メタ)アクリルモノマー(c)
- アクリル系ポリマーを構成するモノマーのモル比が、(a)/(b)/(c)=5〜70/10〜70/5〜70であることを特徴とする請求項1に記載のアクリル系ポリマー。
- カルボキシル基含有モノマー(d)が金属カチオンを含む塩基性物質によって中和された塩に相当する構成単位を1〜70モル%含有することを特徴とする請求項1又は2に記載のアクリル系ポリマー。
- (メタ)アクリルアミドモノマー(e)((b)を除く)に相当する構成単位を0.05〜10モル%含有することを特徴とする請求項1〜3のいずれか一項に記載のアクリル系ポリマー。
- 金属カチオンはリチウムイオン、ナトリウムイオン、カリウムイオンから選ばれる1種又は2種以上の金属カチオンであることを特徴とする請求項1〜4のいずれか一項に記載のアクリル系ポリマー。
- 請求項1〜5のいずれか一項に記載のアクリル系ポリマーを0.1質量%〜100質量%含有することを特徴とする帯電防止剤。
- 請求項1〜5のいずれか一項に記載のアクリル系ポリマーを0.1質量%〜70質量%含有することを特徴とする帯電防止性コーティング組成物。
- 請求項1〜5のいずれか一項に記載のアクリル系ポリマーを0.1質量%〜50質量%含有することを特徴とする帯電防止性粘着剤用アクリル樹脂組成物。
- 請求項1〜5のいずれか一項に記載のアクリル系ポリマーを0.1質量%〜50質量%含有し、さらに不飽和基含有化合物(f)及び重合開始剤(g)を含有し、活性エネルギー線により架橋されてなることを特徴とする帯電防止性粘着剤組成物。
- 請求項1〜5のいずれか一項に記載のアクリル系ポリマーを0.1質量%〜50質量%含有し、さらに架橋剤(h)を含有し、架橋剤(h)により架橋されてなることを特徴とする帯電防止性粘着剤組成物。
- シート状の支持体の少なくとも片面に、請求項9又は10に記載の帯電防止性粘着剤組成物を含有する粘着層が形成されてなる粘着シート。
- 樹脂フィルムに、請求項9又は10に記載の帯電防止性粘着剤組成物を含有する粘着層が形成されてなる光学部材用表面保護フィルム。
- 偏光フィルムからなる支持体の少なくとも片面に、請求項9又は10に記載の帯電防止性粘着剤組成物を含有する粘着層が形成されてなる偏光板。
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