JP6248337B2 - マルチブロック共重合体 - Google Patents
マルチブロック共重合体 Download PDFInfo
- Publication number
- JP6248337B2 JP6248337B2 JP2016511684A JP2016511684A JP6248337B2 JP 6248337 B2 JP6248337 B2 JP 6248337B2 JP 2016511684 A JP2016511684 A JP 2016511684A JP 2016511684 A JP2016511684 A JP 2016511684A JP 6248337 B2 JP6248337 B2 JP 6248337B2
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- Prior art keywords
- block
- block copolymer
- group
- catalyst
- weight
- Prior art date
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- 229920006030 multiblock copolymer Polymers 0.000 title claims description 20
- 239000000178 monomer Substances 0.000 claims description 85
- 229920001400 block copolymer Polymers 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 48
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 31
- 239000003446 ligand Substances 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 29
- 125000000524 functional group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 230000009477 glass transition Effects 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 239000003431 cross linking reagent Substances 0.000 claims description 23
- 239000003999 initiator Substances 0.000 claims description 23
- 239000003638 chemical reducing agent Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000004973 liquid crystal related substance Substances 0.000 claims description 11
- 230000000379 polymerizing effect Effects 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000010410 layer Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- ZPBJLEZUJMQIHC-UHFFFAOYSA-N 2-(2-bromo-2-methylpropanoyl)oxyethyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCOC(=O)C(C)(C)Br ZPBJLEZUJMQIHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- UEBFCIQDWYULRW-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O.CC(C)(Br)C(O)=O.CC(C)(Br)C(O)=O.CC(C)(Br)C(O)=O.OCC(CO)(CO)CO UEBFCIQDWYULRW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- XXSPGBOGLXKMDU-UHFFFAOYSA-M 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C([O-])=O XXSPGBOGLXKMDU-UHFFFAOYSA-M 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- VLRDGSDXAISNJF-UHFFFAOYSA-N [3-(2-bromo-2-methylpropanoyl)oxy-2-[(2-bromo-2-methylpropanoyl)oxymethyl]-2-methylpropyl] 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCC(C)(COC(=O)C(C)(C)Br)COC(=O)C(C)(C)Br VLRDGSDXAISNJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 57
- -1 2-hydroxypropyl Chemical group 0.000 description 34
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 18
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 15
- 239000000853 adhesive Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 101100425892 Danio rerio tpma gene Proteins 0.000 description 11
- 101150048952 TPM-1 gene Proteins 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- VGUWFGWZSVLROP-UHFFFAOYSA-N 1-pyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 VGUWFGWZSVLROP-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 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 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 3
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 3
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- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
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- 230000000977 initiatory effect Effects 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
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- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
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- 235000000346 sugar Nutrition 0.000 description 3
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 2
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 2
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
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- 125000004104 aryloxy group Chemical group 0.000 description 2
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- FFBZKUHRIXKOSY-UHFFFAOYSA-N aziridine-1-carboxamide Chemical compound NC(=O)N1CC1 FFBZKUHRIXKOSY-UHFFFAOYSA-N 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/005—Modified block copolymers
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/06—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the coordination type
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
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Description
(R1)nSi(R2)(4−n)
(R3)nSi(R2)(4−n)
C−X
Mn+Xn
−O−C(O)−(R13R14)C−X
X−C(R13R14)−C(O)−O−Y−O−(O)C−(R15R16)C−Z
2以上のハロゲン元素を含有する化合物を使用したブロック共重合体の製造
エチレンビス(2−ブロモイソブチレート)(Ethylene bis(2−bromoisobutyrate))0.1g及びメチルメタクリレート(methyl methacrylate)17.3gを酢酸エチル(EAc)17.3gに混合した混合物を準備する。その後、触媒0.003gのCuBr2及びリガンドTPMA(トリス(2−ピリジルメチル)アミン:tris(2−pyridylmethyl)amine)0.008gを反応させてCu(II)を形成した後、V−65(2,2’−アゾビス(2,4−ジメチルバレロニトリル):2,2'−azobis−(2,4−dimethyl valeronitrile))0.028gを前記混合物に投入し、これらを一緒に混合する。前記混合物が入っている反応フラスコをゴム膜で阻んで、約25℃で約30分間窒素でパージング(purging)し、バブリング作業を通じて溶存酸素を除去する。酸素が除去された前記反応混合物を、約67℃のオイルバスに浸して反応を開始する。前記単量体の転換率が約75%になると、予め窒素でバブリングしておいたブチルアクリレート(BA:buthyl acrylate)181g、ヒドロキシブチルアクリレート(HBA:hydroxy buthyl acrylate)1.8g及び酢酸エチル(EAc)183gの混合物を窒素存在下で投入する。その後、前記反応フラスコに酸素を除去した触媒0.007gのCuBr2、リガンドTPMA0.018g及び0.034gのV−65を入れた後、鎖延長反応(chain extention reation)を実施する。単量体の転換率が80%以上に到逹すると、前記混合物を酸素に露出し適切な溶媒に希釈して反応を終了することで、メチルメタクリレートで重合された第2ブロック、ブチルアクリレートとヒドロキシブチルアクリレートで重合された第1ブロック及び第3ブロックを含むマルチブロック共重合体を製造する。但し、前記V−65は、その半減期を考慮して、反応終了時点まで適切に分けて入れる。
2以上のハロゲン元素を含有する化合物を使用したブロック共重合体の製造
エチレンビス(2−ブロモイソブチレート)(Ethylene bis(2−bromoisobutyrate))0.1g、メチルメタクリレート(methyl methacrylate)13g及びブチルメタクリレート(buthyl methacrylate)5.6gを酢酸エチル(EAc)7.9gに混合した混合物を準備する。その後、触媒0.003gのCuBr2及びリガンドTPMA(tris(2−pyridylmethyl)amine)0.008gを反応させてCu(II)を形成した後、V−65(2,2'−azobis−(2,4−dimethyl valeronitrile))0.023gを前記混合物に投入し、これらを一緒に混合する。前記混合物が入っている反応フラスコをゴム膜で阻んで、約25℃で約30分間窒素でパージング(purging)し、バブリング作業を通じて溶存酸素を除去する。酸素が除去された前記反応混合物を、約67℃のオイルバスに浸して反応を開始する。 前記単量体の転換率が約75%になると、予め窒素でバブリングしておいたブチルアクリレート(BA:buthyl acrylate)180g、ヒドロキシブチルアクリレート(HBA:hydroxy buthyl acrylate)1.8g及び酢酸エチル(EAc)125gの混合物を窒素存在下で投入する。その後、前記反応フラスコに酸素を除去した触媒0.007gのCuBr2、リガンドTPMA0.018g及び0.038gのV−65を入れた後、鎖延長反応(chain extention reation)を実施する。単量体の転換率が80%以上に到逹すると、前記混合物を酸素に露出し適切な溶媒に希釈して反応を終了することで、メチルメタクリレート及びブチルアクリレートで重合された第2ブロック、ブチルアクリレートとヒドロキシブチルアクリレートで重合された第1ブロック及び第3ブロックを含むマルチブロック共重合体を製造する。但し、前記V−65は、その半減期を考慮して、反応終了時点まで適切に分けて入れる。
一つのハロゲン元素を含有する化合物を使用したブロック共重合体の製造
エチル2−ブロモイソブチレート(EBiB:ethyl 2−bromoisobutyrate)0.29g及びメチルメタクリレート(methyl methacrylate)44.3gを酢酸エチル(EAc)17gに混合した混合物を準備する。その後、触媒0.0048gのCuBr2及びリガンドTPMA(tris(2−pyridylmethyl)amine)0.0123gを反応させてCu(II)を形成した後、V−65(2,2'−azobis−(2,4−dimethyl valeronitrile))0.08gを前記混合物に投入し、これらを一緒に混合する。前記混合物が入っている反応フラスコをゴム膜で阻んで、約25℃で約30分間窒素でパージング(purging)し、バブリング作業を通じて溶存酸素を除去する。酸素が除去された前記反応混合物を、約67℃のオイルバスに浸して反応を開始する。前記単量体の転換率が約75%になると、予め窒素でバブリングしておいたブチルアクリレート(BA:buthyl acrylate)151g、ヒドロキシブチルアクリレート(HBA:hydroxy buthyl acrylate)4.7g及び酢酸エチル(EAc)116gの混合物を窒素存在下で投入する。その後、前記反応フラスコに酸素を除去した触媒0.005gのCuBr2、リガンドTPMA0.014g及び0.07gのV−65を入れた後、鎖延長反応(chain extention reation)を実施する。単量体の転換率が80%以上に到逹すると、前記混合物を酸素に露出し適切な溶媒に希釈して反応を終了することで、メチルメタクリレートで重合された第2ブロック及びブチルアクリレートとヒドロキシブチルアクリレートで重合された第1ブロックを含むブロック共重合体を製造する。但し、前記V−65は、その半減期を考慮して、反応終了時点まで適切に分けて入れる。
一つのハロゲン元素を含有する化合物を使用したブロック共重合体の製造
エチル2−ブロモイソブチレート(EBiB:ethyl 2−bromoisobutyrate)0.14g及びメチルメタクリレート(methyl methacrylate)21.3gを酢酸エチル(EAc)21gに混合した混合物を準備する。その後、触媒0.0023gのCuBr2及びリガンドTPMA(tris(2−pyridylmethyl)amine)0.0098gを反応させてCu(II)を形成した後、V−65(2,2'−azobis−(2,4−dimethyl valeronitrile))0.03gを前記混合物に投入し、これらを一緒に混合する。前記混合物が入っている反応フラスコをゴム膜で阻んで、約25℃で約30分間窒素でパージング(purging)し、バブリング作業を通じて溶存酸素を除去する。酸素が除去された前記反応混合物を、約67℃のオイルバスに浸して反応を開始する。前記単量体の転換率が約75%になると、予め窒素でバブリングしておいたブチルアクリレート(BA:buthyl acrylate)222g、ヒドロキシブチルアクリレート(HBA:hydroxy buthyl acrylate)6.8g及び酢酸エチル(EAc)145gの混合物を窒素存在下で投入する。その後、前記反応フラスコに酸素を除去した触媒0.01gのCuBr2、リガンドTPMA0.04g及び0.08gのV−65を入れた後、鎖延長反応(chain extention reation)を実施する。単量体の転換率が80%以上に到逹すると、前記混合物を酸素に露出し適切な溶媒に希釈して反応を終了することで、メチルメタクリレートで重合された第2ブロック及びブチルアクリレートとヒドロキシブチルアクリレートで重合された第1ブロックを含むブロック共重合体を製造する。但し、前記V−65は、その半減期を考慮して、反応終了時点まで適切に分けて入れる。
一つのハロゲン元素を含有する化合物を使用したブロック共重合体の製造
エチル2−ブロモイソブチレート(EBiB:ethyl 2−bromoisobutyrate)0.06g、メチルメタクリレート(methyl methacrylate)12.6g及びブチルメタクリレート(buthyl methacrylate)5.4gを酢酸エチル(EAc)7.1gに混合した混合物を準備する。その後、触媒0.003gのCuBr2及びリガンドTPMA(tris(2−pyridylmethyl)amine)0.08gを反応させてCu(II)を形成した後、V−65(2,2'−azobis−(2,4−dimethyl valeronitrile))0.08gを前記混合物に投入し、これらを一緒に混合する。前記混合物が入っている反応フラスコをゴム膜で阻んで、約25℃で約30分間窒素でパージング(purging)し、バブリング作業を通じて溶存酸素を除去する。酸素が除去された前記反応混合物を、約67℃のオイルバスに浸して反応を開始する。前記単量体の転換率が約75%になると、予め窒素でバブリングしておいたブチルアクリレート(BA:buthyl acrylate)180g、ヒドロキシブチルアクリレート(HBA:hydroxy buthyl acrylate)1.8g及び酢酸エチル(EAc)118gの混合物を窒素存在下で投入する。その後、前記反応フラスコに酸素を除去した触媒0.007gのCuBr2、リガンドTPMA0.02g及び0.04gのV−65を入れた後、鎖延長反応(chain extention reation)を実施する。単量体の転換率が80%以上に到逹すると、前記混合物を酸素に露出し適切な溶媒に希釈して反応を終了することで、メチルメタクリレート及びブチルアクリレートで重合された第2ブロック、ブチルアクリレートとヒドロキシブチルアクリレートで重合された第1ブロックを含むブロック共重合体を製造する。但し、前記V−65は、その半減期を考慮して、反応終了時点まで適切に分けて入れる。
<粘着剤組成物の製造>
前記実施例1、実施例2及び比較例1〜比較例3で製造したブロック共重合体を適用した樹脂に、架橋剤(トルエンジイソシアネート:toluene diisocyanate、Soken社製)、シランカップリング剤(シアノアセトキシプロピルトリメトキシシラン:cyanoacetoxypropyl trimethoxy silane、(株)LG化学製)及び硬化促進剤(ジブチルスズジラウレート:dibutyltindilaulate、Aldrich社製)を、下記表2の重量部の割合で混合し、コーティング固形分を30重量%で調節して、粘着剤組成物を製造した。
前記実施例1、実施例2及び比較例1〜比較例3で製造された粘着剤組成物を乾燥させた後、これを厚さが23μmになるようにして、離型処理された厚さ38μmのPET(ポリエチレンテレフタレート:poly(ethyleneterephthalate)、三菱社製)フィルムにコーティングした後、約 110℃で約3分間再乾燥させた。その後、片面にWV(wide view)液晶層をコーティングさせた偏光板のWVコーティング層及び前記フィルム上にコーティングさせた粘着剤層を付着させて偏光板を製造した。
ブロック共重合体の各ブロックなどのガラス転移温度(Tg)は、下記数式によって算出した。
1/Tg = ΣWn/Tn
数平均分子量(Mn)は、GPCを使用し、以下の条件で測定した。検量線の製作には、Agilent systemの標準ポリスチレンを使用し、測定結果を換算した。
測定器:Agilent GPC(Agilent 1200 series、U.S.)
カラム:PL Mixed B 2個連結
カラム温度:40℃
溶離液:THF(Tetrahydrofuran)
流速:1.0mL/min
濃度:〜1mg/mL(100μL injection)
前記製造された偏光板を180cm×320cm(縦×横)の大きさで裁断して試片を製造し、これを19インチの市販パネルに付着した。その後、前記パネルを約50℃及び約5気圧で約20分間保管して、サンプル偏光板を製造した。
前記製造されたサンプル偏光板に対する耐湿熱耐久性を評価するため、前記製造されたサンプル偏光板を約60℃の温度及び約90%の相対湿度の条件下で約300時間の間放置した後、粘着界面での気泡または剥離現象の発生有無を目視で観察した。
前記製造されたサンプル偏光板に対する耐熱耐久性を評価するため、前記製造されたサンプル偏光板を約90℃の温度条件下で約300時間の間放置した後、粘着界面での気泡または剥離現象の発生有無を目視で観察した。
前記製造されたサンプル偏光板に対する常温/低湿耐久性を評価するため、前記耐湿熱及び耐熱耐久性を満足するサンプル偏光子を、約25℃及び約25%の相対湿度条件下で30日間放置した後、粘着界面での気泡または剥離現象の発生有無を目視で観察した。
O:気泡及び剥離発生なし
△:気泡及び/または剥離多少発生
X:気泡及び/または剥離多量発生
Claims (19)
- ガラス転移温度が−10℃以下の第1ブロックと、
ガラス転移温度が50℃以上の第2ブロックと、
ガラス転移温度が−10℃以下の第3ブロックと、を含み、
前記第1ブロック及び第3ブロックは、第2ブロックの両末端に各々連結されており、架橋性官能基が前記第1ブロックまたは第3ブロックの側鎖に存在し、
前記第1ブロックまたは第3ブロックは、アクリル酸エステル単量体90〜99.9重量部及び前記架橋性官能基を有する共重合性単量体0.1〜10重量部から誘導された重合された単位を含む、マルチブロック共重合体。 - 前記架橋性官能基が第1ブロック及び第3ブロックの側鎖に含まれる、請求項1に記載のマルチブロック共重合体。
- 前記第1ブロックまたは第3ブロックに含まれる架橋性官能基は、ヒドロキシ基、カルボキシル基、イソシアネート基及びグリシジル基からなる群より選択された1種以上である、請求項1に記載のマルチブロック共重合体。
- 数平均分子量が160,000以上である、請求項1に記載のマルチブロック共重合体。
- 請求項1に記載のマルチブロック共重合体、及び前記マルチブロック共重合体の架橋性官能基と反応できる官能基を2個以上有する架橋剤を含む、粘着剤組成物。
- 前記架橋剤が、イソシアネート架橋剤、エポキシ架橋剤、アジリジン架橋剤又は金属キレート架橋剤である、請求項5に記載の粘着剤組成物。
- 触媒、前記触媒と配位結合することができるリガンド及び構造内に下記化学式3の結合を2個以上有する開始剤の存在下で重合性単量体を重合する段階を含む、請求項1に記載のマルチブロック共重合体の製造方法:
[化学式3]
C−X
〔前記化学式3で、Cは、炭素原子であり、Xは、ハロゲン原子、CN、SR1、N3、S−C(=S)R2及びS−C(=S)N(R3)2で構成される群から選択され、ここで、R1〜R3は、各々独立的にCN;炭素数6〜20のアリール;炭素数1〜20のアルキル;または炭素数1〜20アルキルチオであり、N(R3)2基の場合、2個のR3基が連結されて5または6員のヘテロサイクリック環を形成することができる。また、前記R1〜R3は、一つ以上のハロゲンで置換されることができる〕。 - 触媒は、下記化学式5で表示される化合物である、請求項7に記載のマルチブロック共重合体の製造方法:
[化学式5]
Mn+Xn
〔Mn+は、Cu+1、Cu+2、Fe+2、Fe+3、Ru+2、Ru+3、Cr+2、Cr+3、Mo+2、Mo+3、W+2、W+3、Mn+3、Mn+4、Rh+3、Rh+4、Re+2、Re+3、Co+、Co+2、V+2、V+3、Zn+、Zn+2、Au+、Au+2、Ag+及びAg+2で構成された群より選択され、Xは、ハロゲン原子を示し、nは、金属の形式電荷として、1〜4の整数を示す〕。 - 触媒は、Cu(II)Cl2、Cu(II)Br2、Cu(II)I2またはこれらの混合物である、請求項8に記載のマルチブロック共重合体の製造方法。
- 触媒の含量は、重合性単量体100重量部に対して、0.001〜1重量部である、請求項7に記載のマルチブロック共重合体の製造方法。
- リガンドは、σ−結合を通じて触媒と配位できる窒素、酸素、リン及び硫黄原子を1個以上有するリガンド;またはπ−結合を通じて触媒と配位できる2個以上の炭素原子を含有するリガンドである、請求項7に記載のマルチブロック共重合体の製造方法。
- 構造内に化学式3の結合を2個以上有する開始剤は、下記化学式6で表示される単位を2個以上有する化合物である、請求項7に記載のマルチブロック共重合体の製造方法:
[化学式6]
−O−C(O)−(R13R14)C−X
〔前記化学式6で、R13及びR14は、各々独立的に水素または炭素数1〜8のアルキルであり、Xは、ハロゲン原子である〕。 - 構造内に化学式3の結合を2個以上有する開始剤は、下記化学式7で表示される化合物である、請求項7に記載のマルチブロック共重合体の製造方法:
[化学式7]
X−C(R13R14)−C(O)−O−Y−O−(O)C−(R15R16)C−Z
〔前記化学式7で、R13乃至R16は、各々独立的に水素または炭素数1〜8のアルキルであり、X及びZは、各々独立的にハロゲン原子であり、Yは、炭素数1〜8のアルキレンを示す〕。 - 開始剤は、エチレンビス(2−ブロモイソブチレート)、1,1,1−トリス(2−ブロモイソブチリルオキシメチル)エタン、ペンタエリスリトールテトラキス(2−ブロモイソブチレート)、ジペンタエリスリトールヘキサキス(2−ブロモイソブチレート)またはこれらの混合物である、請求項12または請求項13に記載のマルチブロック共重合体の製造方法。
- 開始剤の含量は、重合性単量体100重量部に対して、0.01〜5重量部である、請求項7に記載のマルチブロック共重合体の製造方法。
- 重合性単量体を重合する段階は、
開始剤、触媒、リガンド及び還元剤の存在下で重合性単量体を重合してマクロ開始剤を製造する段階と、
前記マクロ開始剤、触媒、リガンド及び還元剤の存在下で重合性単量体を重合してマルチブロック共重合体を製造する段階と、
を含む、請求項7に記載のマルチブロック共重合体の製造方法。 - 還元剤は、有機還元剤または無機還元剤である、請求項16に記載のマルチブロック共重合体の製造方法。
- 偏光子;及び
前記偏光子の一面または両面に存在し、請求項5に記載の粘着剤組成物から形成された粘着剤層
を有する、粘着型偏光板。 - 液晶パネルの一面または両面に付着されている請求項18に記載の粘着型偏光板を含む、液晶表示装置。
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