JP2010519347A - 多官能性アジリジンで架橋された針状シリカ粒子を含有する感圧性接着剤 - Google Patents
多官能性アジリジンで架橋された針状シリカ粒子を含有する感圧性接着剤 Download PDFInfo
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- JP2010519347A JP2010519347A JP2009549660A JP2009549660A JP2010519347A JP 2010519347 A JP2010519347 A JP 2010519347A JP 2009549660 A JP2009549660 A JP 2009549660A JP 2009549660 A JP2009549660 A JP 2009549660A JP 2010519347 A JP2010519347 A JP 2010519347A
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 98
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims description 36
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
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- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical class CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 2
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- 239000001530 fumaric acid Substances 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011976 maleic acid Substances 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 claims description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
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- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002759 woven fabric Substances 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
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- 239000004814 polyurethane Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
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- 235000007586 terpenes Nutrition 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical class CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- LSFGICLHZZSFEN-UHFFFAOYSA-N 2-(aziridin-1-yl)butanoic acid 2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCC(C(O)=O)N1CC1.CCC(C(O)=O)N1CC1.CCC(C(O)=O)N1CC1.CCC(CO)(CO)CO LSFGICLHZZSFEN-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- VFUYUMOOAYKNNO-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-(2-methylaziridin-1-yl)propanoic acid Chemical compound CCC(CO)(CO)CO.CC1CN1CCC(O)=O.CC1CN1CCC(O)=O.CC1CN1CCC(O)=O VFUYUMOOAYKNNO-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 1
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 description 1
- UWHCZFSSKUSDNV-UHFFFAOYSA-N 3-(aziridin-1-yl)propanoic acid;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound OC(=O)CCN1CC1.OC(=O)CCN1CC1.OC(=O)CCN1CC1.CCC(CO)(CO)CO UWHCZFSSKUSDNV-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 235000008098 Oxalis acetosella Nutrition 0.000 description 1
- 240000007930 Oxalis acetosella Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
- AVUYXHYHTTVPRX-UHFFFAOYSA-N Tris(2-methyl-1-aziridinyl)phosphine oxide Chemical compound CC1CN1P(=O)(N1C(C1)C)N1C(C)C1 AVUYXHYHTTVPRX-UHFFFAOYSA-N 0.000 description 1
- 239000004775 Tyvek Substances 0.000 description 1
- 229920000690 Tyvek Polymers 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920006271 aliphatic hydrocarbon resin Polymers 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000009820 dry lamination Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011049 pearl Substances 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- HJLBIRSYZDPPIR-UHFFFAOYSA-M sodium;4-dodecoxy-1,4-dioxo-1-prop-2-enoxybutane-2-sulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCC=C HJLBIRSYZDPPIR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
「エマルション」は、1つ以上の界面活性剤により懸濁液中に保持された2つ又はそれ以上の不混和性液体の安定混合物を指し、より詳細には、本発明の重合性モノマー混合物、又は得られたポリマー、及び水との安定混合物を指し、
「ラテックス」は、ポリマーの水性懸濁液又はエマルションを指し、より詳細には、本発明のポリマーの水性エマルションを指し、
「水中油型エマルション」は、水が連続層を形成し、モノマー(油)が不連続液滴である混合物を指し、
水中油型エマルション中の「油相」は、水相中でのその溶解度の限界を個々に超える処方中の全ての成分を指し、これらは一般に、蒸留水中で1%未満の溶解度を有する材料であるが、塩などの水相成分は、特定の油の溶解度を低下させ油相中への分配をもたらすことができ、
水中油型エマルション中の「水相」は、存在する水及び水溶性である成分(すなわち、水中でのその溶解度の限界を超えない)を指し、
「(メタ)アクリレートモノマー」は、アルコールのアクリル酸エステル又はメタクリル酸エステルであり、
本明細書で使用する時、用語「シリカゾル」は、液体中、典型的には水中における分離性非晶質シリカ粒子の分散を指す。
(a)
(i)90〜99重量部の、好ましくは90〜95重量部の、非三級アルコールの(メタ)アクリル酸エステル(該アルコールは1〜14個の炭素原子を有し、好ましくは炭素原子の平均個数が約4〜約12個である)と、
(ii)1〜10重量部の、好ましくは2〜7重量部の酸官能性モノマーと、
(iii)0〜10重量部の第2の非酸官能性極性モノマーと、
(iv)0〜5重量部のビニルモノマーと、
(v)任意に、0.01〜1重量部の多官能性アクリレートと、を含むポリマーと、
(b)100重量部のポリマー(a)を基準として0.001〜1重量部の多官能性アジリジン架橋剤と、
(c)100重量部のポリマーを基準として1〜8重量部の、好ましくは2〜5重量部の針状シリカナノ粒子と、を含む感圧性接着剤を提供する。好ましくは、粒子は、9〜25nmの平均粒径と40〜300nmの長さとを有する。
(a)
(i)90〜99重量部の、好ましくは90〜95重量部の、非三級アルコールの(メタ)アクリル酸エステル(該アルコールは1〜14個の炭素原子を有し、好ましくは炭素原子の平均個数が約4〜約12個である)と、
(ii)1〜10重量部、好ましくは2〜7重量部の酸官能性モノマーと、
(iii)0〜10重量部の第2の非酸官能性極性モノマーと、
(iv)0〜5重量部のビニルモノマーと、
(v)任意に、0.01〜1重量部の多官能性アクリレートと、
(vi)0〜0.5重量部の連鎖移動剤、の反応生成物を含み、
(i)〜(vi)の合計が100重量部であるポリマーと、
(b)100重量部のポリマー(a)を基準として0.001〜1重量部の多官能性アジリジン架橋剤と、
(c)100重量部のポリマーを基準として1〜8重量部の、好ましくは2〜5重量部の針状シリカナノ粒子と、を含む。ナノ粒子は、好ましくは9〜25nmの平均粒径と40〜300nmの長さとを有し、
(d)エマルションの総重量を基準として、0.5〜約8重量パーセントの界面活性剤、好ましくはアニオン性界面活性剤を含む、30〜70重量パーセントの水相と、を有する。
R1はポリオールの残基であり、
R2は−H又は−OHであり、
R3は−H又は−CH3であり、
xは2を超え、好ましくは少なくとも3であり、
yは0〜3である。
(a)
(i)アクリル酸エステルと、
(ii)酸官能性モノマーと、
(iii)任意の極性モノマーと、
(iv)任意のビニルモノマーと、
(v)任意の多官能性アクリレートと、
(vi)任意の連鎖移動剤と、を含むモノマープレミックスを製造する工程と、
(b)
(i)水と、
(ii)アニオン性界面活性剤、非イオン性界面活性剤、カチオン性界面活性剤、両性界面活性剤、高分子界面活性剤、及びこれらの混合物からなる群から選択される界面活性剤と、
(iii)フリーラジカル反応開始剤と、を含む水相と前記プレミックスとを混合する工程と、
(c)前記エマルションを撹拌しながら、温度約30℃〜約80℃まで加熱し、ポリマーラテックスが形成されるまで水中油型エマルション中の前記モノマーを重合させる工程と、を含む。その他の混合物が使用されてもよいことが理解されるであろう。例えば、酸官能性モノマー、又はその他の親水性モノマーが、水溶液に添加されてもよい。更に、一旦エマルション混合物が調製されると、モノマーは、それらのそれぞれの分配係数により油相及び水相の間を分割し得る。
剥離接着試験
使用した試験方法は、ガラス基材がステンレス鋼の代わりに使用されたことを除いて、試験法ASTM D 3330−78と同様であった。テープ試料は、50.8マイクロメートル(2ミル)の厚さのポリエステルフィルムに接着剤をコーティングし、乾燥することにより調製し、約38マイクロメートル(1.5ミル)の接着剤の乾燥コーティングした厚さを設けた。これらのテープの2つの1.3cm(0.5インチ)ストリップを、2kg(4.5ポンド)ローラーをテープ上で転がすことによりガラスプレートに付着した。2つのテープ試料を平均した。圧盤速度は、229cm/分(90インチ/分)であった。剥離力を0.5インチ当たりのオンス単位で測定し、デシメートル当たりのニュートンに変換した。
試験方法は、試験法ASTM D−3654−78、PSTC−7と同様であった。テープ試料は、50.8マイクロメートル(2ミル)の厚さのポリエステルフィルムに接着剤をコーティングし、乾燥することにより調製し、約38マイクロメートル(1.5ミル)の接着剤の乾燥コーティングした厚さを設けた。1.3cm(0.5インチ)幅のこれらのテープのストリップをステンレス鋼プレートに付着して切断し、1.3cm×1.3cm(0.5インチ×0.5インチ)正方形を鋼プレート上に残した。2kg(4.5ポンド)の重量を接着部分上で転がした。1,000gの重量を各試料に取り付け、試料が破壊するまで吊るした。破壊時間並びに破壊状態を書きとめた。試料は、3度試験し、平均した。試験は、23℃、50%相対湿度で行った。
1リットルのステンレス鋼ワーニング(Waring)ブレンダー容器に、360gの脱イオン水、8gのローダカルDS−10、1.0gの水酸化リチウム、1.2gのトリエタノールアミン、344gの2−オクチルアクリレート(2−OA)、15gのアクリル酸(AA)、及び15gのメチルメタクリレート(MMA)を添加した。内容物をブレンダーにより低速度設定で2分間均質化し、その後温度計、テフロン(登録商標)インペラを備える機械的攪拌器、凝縮器及び窒素入口管を備えた2リットル樹脂フラスコに注いだ。続いて、0.8gの過硫酸カリウムを加えた。反応混合物を窒素ブランケット下で250rpmで攪拌し、62℃まで加熱した。攪拌及び窒素ブランケットを反応時間全体にわたって維持した。発熱が約90℃でピークに達した後、82gの脱イオン水を添加した。バッチを4時間にわたって75℃に維持し、冷却してチーズクロスによりろ過し、固形分47.3%、ブルックフィールド(Brookfield)粘度0.84パスカル秒(840cps)、及びpH4.3のラテックス接着剤を得た。平均粒径をコールター(Coulter)N4MD粒子分析器で測定すると、0.14マイクロメートルであった。
PFAZ 322を、PSA−1エマルション接着剤に重量比0.05%で添加した。架橋剤を溶液内に混合すると、接着剤はゲル化し、コーティングや試験をすることができなかった。
電磁攪拌器で攪拌中に濃水酸化アンモニウムを溶液に添加することにより、PSA−1のpHが上昇した。pHの上昇をpHメーターを用いて観測し、pHが9.0に達した時点で塩基の添加を中止した。この塩基性接着剤溶液は、0.05%のPFAZ 322添加によりゲル化しなかった。以下のPSA−1について言及する全てのものは、pHを9.0まで上昇させたものを指す。
PSA−1を様々な濃度のスノーテックス・アップ(SNOWTEX UP)と混合した。表1に示すように、PFAZ 322添加及び無添加の接着剤溶液も調製した。PFAZ 322無添加の試料は比較例C3A〜C3Cである。比較例C2から比較試料も調製した。上記試験方法に記載したように、これらの接着剤エマルション溶液から調製されたテープの剥離接着及び剪断強度を測定した。記載した重量パーセントは乾燥ポリマーに対して算出される。比較例C8は、針状ナノ粒子を含まない多官能性アジリジン架橋剤の効果を示すために含める。
PSA−2を様々な濃度のスノーテックス・アップ(SNOWTEX UP)と混合した。表2に示すように、PFAZ 322添加及び無添加の接着剤溶液も調製した。PFAZ 322無添加の試料は比較例C5A〜C5Cである。スノーテックス・アップ(SNOWTEX UP)を含まない比較試料も調製した(比較例C4)。上記試験方法に記載したように、これらの接着剤エマルション溶液から調製されたテープの剥離接着及び剪断強度を測定した。記載した重量パーセントは乾燥ポリマーに対して算出される。
電磁攪拌器で攪拌中に濃水酸化アンモニウムを溶液に添加することにより、PSA−3のpHが上昇した。pHの上昇をpHメーターを用いて観測し、pHが9.0に達した時点で塩基の添加を中止した。この塩基性接着剤溶液は、0.05%のPFAZ 322添加によってゲル化しなかった。以下のPSA−3について言及する全てのものは、pHを9.0まで上昇させたものを指す。PSA−3を様々な濃度のスノーテックス・アップ(SNOWTEX UP)と混合した。表3に示すように、PFAZ322添加及び無添加の接着剤溶液も調製した。PFAZ 322無添加の試料は比較例C7A〜C7Bである。スノーテックス・アップ(SNOWTEX UP)を含まない比較試料も調製した(比較例C6)。上記試験方法に記載したように、これらの接着剤エマルション溶液から調製されたテープの剥離接着及び剪断強度を測定した。記載した重量パーセントは乾燥ポリマーに対して算出される。
Claims (19)
- (a)
(i)90〜99重量部の、非三級アルコールの(メタ)アクリル酸エステル(該アルコールは1〜14個の炭素原子を有し、好ましくは炭素原子の平均個数が約4〜約12個である)と、
(ii)1〜10重量部の酸官能性モノマーと、
(iii)0〜10重量部の第2の非酸官能性極性モノマーと、
(iv)0〜5重量部のビニルモノマーと、
(v)任意に、0.01〜1重量部の多官能性アクリレートと、を含むポリマーと、
(b)100重量部のポリマー(a)を基準として0.001〜1重量部の多官能性アジリジン架橋剤と、
(c)100重量部のポリマー(a)を基準として1〜8重量部の、9〜25nmの平均粒径と40〜300nmの長さとを有するシリカナノ粒子と、
を含む感圧性接着剤。 - 前記シリカナノ粒子が針状である、請求項1に記載の感圧性接着剤。
- 前記針状シリカナノ粒子が表面改質されていない、請求項2に記載の感圧性接着剤。
- 前記針状シリカナノ粒子が親水性表面改質剤で表面改質されている、請求項2に記載の感圧性接着剤。
- 前記酸官能性モノマーの酸官能基がポリマー中で少なくとも部分的に中和されている、請求項1に記載の感圧性接着剤。
- 前記第2の極性モノマーが、2−ヒドロキシエチル(メタ)アクリレート;N−ビニルピロリドン;N−ビニルカプロラクタム;アクリルアミド;t−ブチルアクリルアミド;ジメチルアミノエチルアクリルアミド;N−オクチルアクリルアミド;2−(2−エトキシエトキシ)エチルアクリレート、2−エトキシエチルアクリレート、2−メトキシエトキシエチルアクリレート、2−メトキシエチルメタクリレート、ポリエチレングリコールモノ(メタ)アクリレートを含むポリ(アルコキシアルキル)アクリレート;ポリ(ビニルメチルエーテル);及びこれらの混合物から選択される、請求項1に記載の感圧性接着剤。
- 前記ポリマーが1〜5重量部のアクリル酸及び1〜5重量部の第2の極性モノマーを含む、請求項1に記載の感圧性接着剤。
- 前記ポリマーが水性エマルションポリマーとして調製される、請求項1に記載の感圧性接着剤。
- 前記酸官能性モノマーが、アクリル酸、メタクリル酸、イタコン酸、フマル酸、クロトン酸、シトラコン酸、マレイン酸、オレイン酸、β−カルボキシエチルアクリレート、2−スルホエチルメタクリレート、スチレンスルホン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、ビニルホスホン酸、及びこれらの混合物から選択される、請求項1に記載の感圧性接着剤。
- ビニルエステル、スチレン、置換スチレン、ビニルハロゲン化物、プロピオン酸ビニル、及びこれらの混合物から選択される1〜5重量部のビニルモノマーを含む、請求項1に記載の感圧性接着剤。
- 前記ポリマー成分がポリマーの混合物を含む、請求項1に記載の組成物。
- 前記非第三級アルコールの炭素原子の平均個数が約4〜約12個である、請求項1に記載の組成物。
- 0〜8重量部の、20ナノメートル以下の平均粒径を有する球形状シリカナノ粒子を更に含む、請求項2に記載の組成物。
- 50重量%以下の前記針状シリカナノ粒子が、20ナノメートル以下の平均粒径を有する球形状シリカナノ粒子によって置換される、請求項2に記載の組成物。
- 請求項1に記載の感圧性接着剤、及び可撓性裏層を含む、接着剤物品。
- 前記可撓性裏層が、紙、ラテックス含浸紙、高分子フィルム、ポリラクチド、酢酸セルロースフィルム、エチルセルロースフィルム、織布又は不織布、金属フォイル、及びセラミックシートから選択される、請求項16に記載の接着剤コーティングされたシート物品。
- (a)エマルションの総重量を基準として30〜約70重量パーセントの請求項1に記載の接着剤と、
(b)エマルションの総重量を基準として30〜70重量パーセントの、界面活性剤を含む水相と、
を含むエマルション。 - 前記組成物のpHが7を超える、請求項18に記載のエマルション。
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EP2886620B1 (en) | 2013-12-18 | 2019-11-27 | 3M Innovative Properties Company | Post-curable pressure-sensitive adhesive |
JP6310731B2 (ja) * | 2014-03-07 | 2018-04-11 | スリーエム イノベイティブ プロパティズ カンパニー | 熱硬化性感圧接着剤 |
KR101882563B1 (ko) * | 2015-11-30 | 2018-07-27 | 삼성에스디아이 주식회사 | 편광판용 점착 필름, 이를 위한 편광판용 점착제 조성물, 이를 포함하는 편광판 및 이를 포함하는 광학표시장치 |
CN109749671B (zh) * | 2017-11-02 | 2020-12-08 | 3M创新有限公司 | 含纳米硅氧烷缩合物的丙烯酸酯压敏胶粘合剂、粘合片及其制备方法 |
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Also Published As
Publication number | Publication date |
---|---|
DE602008003760D1 (de) | 2011-01-13 |
CN101646739B (zh) | 2012-03-14 |
EP2121864B1 (en) | 2010-12-01 |
KR20100014409A (ko) | 2010-02-10 |
CN101646739A (zh) | 2010-02-10 |
EP2121864A1 (en) | 2009-11-25 |
ATE490296T1 (de) | 2010-12-15 |
WO2008100713A1 (en) | 2008-08-21 |
US20080200587A1 (en) | 2008-08-21 |
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