JP2011522074A - (メタ)アクリレートを主成分とするシリル官能化abaトリブロックコポリマーを製造する方法 - Google Patents
(メタ)アクリレートを主成分とするシリル官能化abaトリブロックコポリマーを製造する方法 Download PDFInfo
- Publication number
- JP2011522074A JP2011522074A JP2011510918A JP2011510918A JP2011522074A JP 2011522074 A JP2011522074 A JP 2011522074A JP 2011510918 A JP2011510918 A JP 2011510918A JP 2011510918 A JP2011510918 A JP 2011510918A JP 2011522074 A JP2011522074 A JP 2011522074A
- Authority
- JP
- Japan
- Prior art keywords
- block
- silyl
- meth
- block copolymer
- acrylates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 17
- 229920000428 triblock copolymer Polymers 0.000 title abstract description 11
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 53
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 52
- 229920000642 polymer Polymers 0.000 claims description 45
- 229920001400 block copolymer Polymers 0.000 claims description 44
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 239000003999 initiator Substances 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 15
- 238000009826 distribution Methods 0.000 claims description 14
- 239000003446 ligand Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000007306 functionalization reaction Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000565 sealant Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 150000003623 transition metal compounds Chemical class 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004026 adhesive bonding Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- 239000012943 hotmelt Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- 238000004132 cross linking Methods 0.000 description 16
- 239000011230 binding agent Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- -1 cyclic dienes Chemical class 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 229920000193 polymethacrylate Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229940090181 propyl acetate Drugs 0.000 description 7
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 6
- 238000006459 hydrosilylation reaction Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical group 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- LHZBJSPSWKIJKZ-UHFFFAOYSA-N 4-(2-bromo-2-methylpropanoyl)oxybutyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCCCOC(=O)C(C)(C)Br LHZBJSPSWKIJKZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 229920006250 telechelic polymer Polymers 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010550 living polymerization reaction Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 238000007342 radical addition reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- PGMMQIGGQSIEGH-UHFFFAOYSA-N 2-ethenyl-1,3-oxazole Chemical compound C=CC1=NC=CO1 PGMMQIGGQSIEGH-UHFFFAOYSA-N 0.000 description 2
- JDCUKFVNOWJNBU-UHFFFAOYSA-N 2-ethenyl-1,3-thiazole Chemical compound C=CC1=NC=CS1 JDCUKFVNOWJNBU-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 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
- 150000001412 amines Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
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- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 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
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- JVPKLOPETWVKQD-UHFFFAOYSA-N 1,2,2-tribromoethenylbenzene Chemical compound BrC(Br)=C(Br)C1=CC=CC=C1 JVPKLOPETWVKQD-UHFFFAOYSA-N 0.000 description 1
- DDPGLQRMAQYQEQ-UHFFFAOYSA-N 1-butoxypropyl 2-methylprop-2-enoate Chemical compound CCCCOC(CC)OC(=O)C(C)=C DDPGLQRMAQYQEQ-UHFFFAOYSA-N 0.000 description 1
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- LEWNYOKWUAYXPI-UHFFFAOYSA-N 1-ethenylpiperidine Chemical compound C=CN1CCCCC1 LEWNYOKWUAYXPI-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- WIWZLDGSODDMHJ-UHFFFAOYSA-N 1-ethoxybutyl 2-methylprop-2-enoate Chemical compound CCCC(OCC)OC(=O)C(C)=C WIWZLDGSODDMHJ-UHFFFAOYSA-N 0.000 description 1
- HVBADOTWUFBZMF-UHFFFAOYSA-N 1-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOC(C)OC(=O)C(C)=C HVBADOTWUFBZMF-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- RUZAHKTXOIYZNE-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid;iron(2+) Chemical compound [Fe+2].OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O RUZAHKTXOIYZNE-UHFFFAOYSA-N 0.000 description 1
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- XIXWTBLGKIRXOP-UHFFFAOYSA-N 2-ethenyloxolane Chemical compound C=CC1CCCO1 XIXWTBLGKIRXOP-UHFFFAOYSA-N 0.000 description 1
- ZDHWTWWXCXEGIC-UHFFFAOYSA-N 2-ethenylpyrimidine Chemical compound C=CC1=NC=CC=N1 ZDHWTWWXCXEGIC-UHFFFAOYSA-N 0.000 description 1
- YQGVJKSRGWEXGU-UHFFFAOYSA-N 2-ethenylthiolane Chemical compound C=CC1CCCS1 YQGVJKSRGWEXGU-UHFFFAOYSA-N 0.000 description 1
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- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
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- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
- UIRSDPGHIARUJZ-UHFFFAOYSA-N 3-ethenylpyrrolidine Chemical compound C=CC1CCNC1 UIRSDPGHIARUJZ-UHFFFAOYSA-N 0.000 description 1
- DHNFGUDLVOSIKJ-UHFFFAOYSA-N 3-methyl-1-(3-methylbuta-1,3-dienoxy)buta-1,3-diene Chemical compound CC(=C)C=COC=CC(C)=C DHNFGUDLVOSIKJ-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- JBENUYBOHNHXIU-UHFFFAOYSA-N 4-ethenyl-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C=C JBENUYBOHNHXIU-UHFFFAOYSA-N 0.000 description 1
- LKLNVHRUXQQEII-UHFFFAOYSA-N 5-ethenyl-2,3-dimethylpyridine Chemical compound CC1=CC(C=C)=CN=C1C LKLNVHRUXQQEII-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
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- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
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- 230000000415 inactivating effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-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
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- XTTBHNHORSDPPN-UHFFFAOYSA-J naphthalene-1-carboxylate;tin(4+) Chemical compound [Sn+4].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 XTTBHNHORSDPPN-UHFFFAOYSA-J 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- QGZWYBQTXJMHIW-UHFFFAOYSA-N octane-3-thiol Chemical compound CCCCCC(S)CC QGZWYBQTXJMHIW-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- XGRBZUSXGVNWMI-UHFFFAOYSA-N phenylmethoxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOCC1=CC=CC=C1 XGRBZUSXGVNWMI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material 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
- 125000001424 substituent group Chemical group 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
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- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/005—Modified block copolymers
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Graft Or Block Polymers (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
DE3832466では、特にグループ・トランスファー重合(GTP)によるP(AMA)−(MMA)−(AMA)トリブロックコポリマーの製造を記載している。しかし、本特許明細書で記載した材料は、これらのポリマーが早期に架橋反応を起こしやすく、安定化した場合であっても貯蔵においては安定ではないことが当業者には明らかである。さらに、シリル官能化ポリマーを得るには、さらにヒドロシリル化のさらなる段階を実行する必要がある。GTPを用いてシリル官能化ポリメタクリレートを直接合成する方法は、文献には見当たらない。
H2C=CR3C(O)O−R4−Si(OR1)bR2 aXc
この式において、有機基R1およびR2はそれぞれ同一であるか互いに異なっていてよい。さらに、有機基R1およびR2は、1〜20個の炭素原子からなる脂肪族炭化水素基の群から選択される。これらの群は、直鎖、分枝鎖または環状のいずれかであってよい。この場合、R1は排他的に水素であってもよい。
数平均分子量Mn、重量平均分子量Mwおよび分子量分布Mw/Mnは、ゲル透過クロマトグラフィー(GPC)によってテトラヒドロフラン中でPMMA基準にて測定する。
攪拌機、温度計、還流冷却器、窒素導入管および滴下漏斗を備え付けたジャケット付き容器中に、N2雰囲気下で、モノマー1a(正確な名称および量は第1表に記載)、酢酸プロピル125mL、酸化銅(I)0.5gおよびN,N,N’,N’’,N’’−ペンタメチルジエチレントリアミン(PMDETA)1.3gを装填した。この溶液を80℃で15分間攪拌した。引き続き、同じ温度で、酢酸プロピル25mL中に溶解した開始剤1,4−ブタンジオール−ジ(2−ブロモ−2−メチルプロピオネート)(BDBIB;量は第1表を参照のこと)を滴下した。3時間の重合の後に試料を取り出して平均モル質量Mnを測定し(SEC)、モノマー2aおよびモノマー3aの混合物(正確な名称および量は第1表に記載)を添加した。この混合物を予測される少なくとも95%の反応率まで重合し、n−ドデシルメルカプタン2.1gの添加によって反応を停止させた。この溶液を、シリカゲルで濾過し、その後、蒸留により揮発性成分を除去することにより後処理した。最後に平均分子量をSEC測定により測定した。導入されたモノマー3aの量を、1H−NMR測定により定量した。
実施例1と同様に、モノマー1b、2bおよび3b(正確な名称および量は第1表に記載)を使用した。
実施例1と同様に、モノマー1c、2cおよび3c(正確な名称および量は第1表に記載)を使用した。
実施例1と同様に、モノマー1d、2dおよび3d(正確な名称および量は第1表に記載)を使用した。
攪拌機、温度計、還流冷却器、窒素導入管および滴下漏斗を備え付けたジャケット付き容器中に、N2雰囲気下で、モノマーIa(正確な名称および量は第2表に記載)、酢酸プロピル145mL、酸化銅(I)0.62gおよびN,N,N’,N’’,N’’−ペンタメチルジエチレントリアミン(PMDETA)1.6gを装填した。この溶液を80℃で15分間攪拌した。引き続き、同じ温度で、酢酸プロピル30mL中に溶解した開始剤1,4−ブタンジオール−ジ(2−ブロモ−2−メチルプロピオネート)(BDBIB;量は第1表を参照のこと)を滴下した。3時間の重合の後に試料を取り出して平均モル質量Mnを測定し(SEC)、モノマーIIa(正確な名称および量は第2表に記載)を添加した。95%の反応率を算出した後、最後にモノマーIIa’とモノマーIIIa(正確な名称および量は第2表を参照のこと)の混合物を添加した。この混合物を予測される少なくとも95%の反応率まで重合し、n−ドデシルメルカプタン2.4gの添加によって反応を停止させた。この溶液を、シリカゲルで濾過し、その後、蒸留により揮発性成分を除去することにより後処理した。最後に平均分子量をSEC測定により測定した。導入されたモノマー3aの量を、1H−NMR測定により定量した。
攪拌機、温度計、還流冷却器、窒素導入管および滴下漏斗を備え付けたジャケット付き容器中に、N2雰囲気下で、モノマーIb(正確な名称および量は第2表に記載)、酢酸プロピル150mL、酸化銅(I)0.60gおよびN,N,N’,N’’,N’’−ペンタメチルジエチレントリアミン(PMDETA)1.6gを装填した。この溶液を80℃で15分間攪拌した。引き続き、同じ温度で、酢酸プロピル35mL中に溶解した開始剤1,4−ブタンジオール−ジ(2−ブロモ−2−メチルプロピオネート)(BDBIB;量は第1表を参照のこと)を滴下した。3時間の重合の後に試料を取り出して平均モル質量Mnを測定し(SEC)、モノマーIIbとモノマーIIIb(正確な名称および量は第2表に記載)の混合物を添加した。95%の反応率を算出した後、最後にモノマーIIb’(正確な名称および量は第2表を参照のこと)を添加した。この混合物を予測される少なくとも95%の反応率まで重合し、n−ドデシルメルカプタン2.4gの添加によって反応を停止させた。この溶液を、シリカゲルで濾過し、その後、蒸留により揮発性成分を除去することにより後処理した。最後に平均分子量をSEC測定により測定した。導入されたモノマー3aの量を、1H−NMR測定により定量した。
Claims (17)
- 個々のAブロックに1個以上4個以下のシリル基を有する組成ABAのブロックコポリマーであって、シリル官能化(メタ)アクリレートおよび(メタ)アクリレートまたはその混合物の群から選択される非シリル官能性モノマーを含有するコポリマーであるブロックA、および付加的なシリル官能基を有さず、その組成がブロックAの非シリル官能性モノマーの組成とは異なる(メタ)アクリレートまたはその混合物を含有する1個のブロックBが、ABAブロックコポリマーとして重合されることを特徴とするブロックコポリマー。
- ABAブロックコポリマーの個々のAブロックが、1個以上2個以下のシリル基を含む組成を有することを特徴とする、請求項1に記載のブロックコポリマー。
- 個々のAブロックがそれぞれABAブロックコポリマーの合計質量の25%未満を構成することを特徴とする、請求項1または2に記載のブロックコポリマー。
- 個々のAブロックがそれぞれABAブロックコポリマーの合計質量の10%未満を構成することを特徴とする、請求項3に記載のブロックコポリマー。
- 個々のBブロックが同様に本質的にCDCトリブロック構造を有するためACDCAペンタブロックコポリマーが形成されることを特徴とする、請求項1から4に記載のブロックコポリマー。
- Cブロックの組成がAブロック中の非シリル官能化成分の組成に該当することを特徴とする、請求項5に記載のブロックコポリマー。
- 個々のAブロックが同様に本質的にCA’ジブロック構造を有して、ブロックA’が(メタ)アクリレートまたはその混合物の群から選択されるモノマーを包み、Cブロックが非シリル官能化(メタ)アクリレートを含有するほかはA’ブロックの組成に合致することから、CA’BA’Cペンタブロックコポリマーが形成されることを特徴とする、請求項1に記載のブロックコポリマー。
- Aセグメントの官能化に用いるモノマーが不飽和のフリーラジカル重合が可能な基およびシリル基を含有し、この付加的なシリル基が
−Si(OR1)bR2 aXc
[式中、
有機基R1およびR2はそれぞれ同一であるか互いに異なっており、1〜20個の炭素原子からなる直鎖、分枝鎖または環状脂肪族炭化水素基の群から選択され、R1は排他的に水素であってもよく、
Xはアルコキシおよびヒドロキシル以外の加水分解可能な基の群から選択され、
a、bおよびcはそれぞれ0〜3の整数であって、a、bおよびcの合計は3である]
の形態を有することを特徴とする、請求項1に記載のブロックコポリマー。 - ハロゲン非含有の溶剤中で、開始剤および触媒の存在下にて原子移動ラジカル重合(ATRP)を連続的に実施することにより、ブロックAをシリル官能化(メタ)アクリレートと(メタ)アクリレートまたはその混合物の群から選択されるモノマーとの混合物から得て、ブロックBを付加的なシリル官能基を有さない(メタ)アクリレートまたはその混合物から得ることを特徴とする、個々のAブロックに4個以下のシリル基を有する組成ABAのブロックコポリマーの作製方法。
- 開始剤が二官能性開始剤であることを特徴とする、請求項9に記載のブロックコポリマーの作製方法。
- 触媒として遷移金属化合物、好ましくは銅化合物を使用し、配位子としてN含有キレート配位子を使用することを特徴とする、請求項9および10に記載のブロックコポリマーの作製方法。
- ブロックコポリマーの数平均分子量が5000g/モル〜100000g/モルであることを特徴とする、請求項9に記載のブロックコポリマーの作製方法。
- ブロックコポリマーの数平均分子量が好ましくは7500g/モル〜50000g/モルであることを特徴とする、請求項9に記載のブロックコポリマーの作製方法。
- ブロックコポリマーの分子量分布が1.6未満であることを特徴とする、請求項9に記載のブロックコポリマーの作製方法。
- 重合後にメルカプタンまたはチオール基を含有する化合物を添加することにより触媒が沈殿し、濾過によってポリマー溶液から除去されることを特徴とする、請求項9に記載のペンタブロックコポリマーの作製方法。
- シリル官能化(メタ)アクリレートおよび(メタ)アクリレートまたはその混合物の群から選択されるモノマーを含有するコポリマーであるブロックA、および付加的なシリル官能基を有さず、(メタ)アクリレートまたはその混合物を含有する1個のブロックBが、ABAブロックコポリマーとして重合されることを特徴とする、個々のAブロックに4個以下のシリル官能化基を有する組成ABAのブロックコポリマーの、反応性ホットメルト接着剤、接着結合組成物または封止剤における使用。
- シリル官能化(メタ)アクリレートおよび(メタ)アクリレートまたはその混合物の群から選択されるモノマーを含有するコポリマーであるブロックA、および付加的なシリル官能基を有さず、(メタ)アクリレートまたはその混合物を含有する1個のブロックBが、ABAブロックコポリマーとして重合されることを特徴とする、個々のAブロックに4個以下のシリル官能化基を有する組成ABAのブロックコポリマーの、ヒートシール応用例における使用。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019208386A1 (ja) * | 2018-04-27 | 2019-10-31 | 東亞合成株式会社 | 硬化性樹脂組成物、並びに、ブロック共重合体及びその製造方法 |
JP2021066811A (ja) * | 2019-10-24 | 2021-04-30 | 東亞合成株式会社 | 硬化性樹脂組成物及び接着剤組成物 |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2009225508A1 (en) | 2008-03-20 | 2009-09-24 | Avery Dennison Corporation | Acrylic polymers having controlled placement of functional groups |
DE102008025575A1 (de) | 2008-05-28 | 2009-12-03 | Evonik Röhm Gmbh | Mit Wasser vernetzbare Dichtmasse |
DE102008043674A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit einer bimodalen Molekulkargewichtsverteilung |
DE102008043662A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit breiter Molekulargewichtsverteilung |
DE102008043669A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem breit verteilten B-Block |
DE102008043666A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem bimodalen verteilten A-Block |
DE102008043658A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem breit verteilten A-Block |
DE102008043668A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem bimodalen B-Block |
DE102009001771A1 (de) | 2009-03-24 | 2010-09-30 | Henkel Ag & Co. Kgaa | Erstarrende Klebstoffe mit Silanvernetzung |
DE102009027620A1 (de) | 2009-07-10 | 2011-01-13 | Evonik Röhm Gmbh | Copolymerisation von Silyl-funktionellen Komponenten in wässrigen Polymerisationssystemen |
DE102009046190A1 (de) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Kaschierklebstoff mit Silanvernetzung |
WO2011139573A2 (en) * | 2010-04-28 | 2011-11-10 | 3M Innovative Properties Company | Silicone-based material |
WO2011146450A1 (en) | 2010-05-19 | 2011-11-24 | Avery Dennison Corporation | Ordered architectures in acrylic polymers |
US8436094B2 (en) * | 2010-08-25 | 2013-05-07 | Henkel Corporation | Curable compositions with moisture-curable functionality clusters near the chain ends |
EP2766404B1 (en) * | 2011-10-14 | 2019-11-13 | Avery Dennison Corporation | Controlled architecture polymers |
WO2014148552A1 (ja) * | 2013-03-21 | 2014-09-25 | 横浜ゴム株式会社 | プライマー |
EP2993194B1 (en) * | 2013-05-02 | 2019-07-03 | LG Chem, Ltd. | Multi-block copolymer |
CN104415740B (zh) * | 2013-09-04 | 2017-02-08 | 北京蛋白质组研究中心 | 亲水色谱填料及其制备方法与应用 |
BR112016014668A2 (pt) | 2013-12-23 | 2017-08-08 | Cytec Ind Inc | Método para sintetizar um polímero de poliacrilonitrila, polímero de poliacrilonitrila, e, método para produzir uma fibra de carbono |
US9587062B2 (en) | 2014-12-15 | 2017-03-07 | Henkel IP & Holding GmbH and Henkel AG & Co. KGaA | Photocrosslinkable block copolymers for hot-melt adhesives |
CN108417836B (zh) * | 2018-01-31 | 2021-05-04 | 闽南师范大学 | 一种锂离子电池的电极粘结剂及其制备方法 |
CN109251284A (zh) * | 2018-08-02 | 2019-01-22 | 常州大学 | 一种可常温交联聚丙烯酸酯弹性体及其制备方法 |
JP2022537506A (ja) * | 2019-06-14 | 2022-08-26 | ザ ガバメント オブ ザ ユナイテッド ステイツ オブ アメリカ, アズ リプレゼンテッド バイ ザ セクレタリー オブ ザ ネイビー | シリル含有アクリレートおよびそれらの分解性ラジカル硬化ネットワーク |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001200026A (ja) * | 1999-11-12 | 2001-07-24 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体の製法およびその製法で得られたブロック共重合体 |
JP2002060449A (ja) * | 2000-08-11 | 2002-02-26 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体を含有する硬化性組成物 |
WO2002092696A1 (fr) * | 2001-05-14 | 2002-11-21 | Kaneka Corporation | Composition de resine thermoplastique |
JP2002338625A (ja) * | 2001-05-14 | 2002-11-27 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体 |
WO2008021500A2 (en) * | 2006-08-17 | 2008-02-21 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Modification of surfaces with polymers |
JP2009509014A (ja) * | 2005-09-22 | 2009-03-05 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | (メタ)アクリレートベースのaba−トリブロックコポリマーの製造方法 |
JP2010539265A (ja) * | 2007-09-12 | 2010-12-16 | コンストラクション リサーチ アンド テクノロジー ゲーエムベーハー | シラン変性コポリマーの製造方法 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR900003910B1 (ko) | 1987-09-26 | 1990-06-04 | 한국과학기술원 | 비스실록산 중합개시제를 이용한 중합체의 제조방법 |
US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
CA2258006C (en) | 1996-06-12 | 2008-07-29 | University Of Warwick | Polymerisation catalyst and process |
EP0910587B1 (en) | 1996-07-10 | 2001-12-12 | E.I. Du Pont De Nemours And Company | Polymerization with living characteristics |
TW593347B (en) | 1997-03-11 | 2004-06-21 | Univ Carnegie Mellon | Improvements in atom or group transfer radical polymerization |
EP1637544A3 (en) | 1997-04-18 | 2006-05-17 | Kaneka Corporation | Polymers, process for processing the same, and curable compositions produced therefrom |
DE69829063T2 (de) | 1997-09-22 | 2006-03-23 | Kaneka Corp. | Polymer, verfahren zu dessen herstellung und härtbare zusammensetzung, die dieses polymer enthält |
CN1152061C (zh) | 1998-02-27 | 2004-06-02 | 钟渊化学工业株式会社 | 丙烯酰基或甲基丙烯酰基封端的乙烯基聚合物及其用途 |
WO1999050315A1 (fr) | 1998-03-27 | 1999-10-07 | Kaneka Corporation | Polymere et procede de production de polymere |
EP2028197A1 (en) | 1998-09-02 | 2009-02-25 | Kaneka Corporation | Polymer, process for producing polymer and composition |
EP1652884B1 (en) | 1998-10-08 | 2009-07-08 | Kaneka Corporation | Curable compositions |
US6855780B1 (en) | 1999-01-28 | 2005-02-15 | Kaneka Corporation | Polymer, process for producing the polymer, and curable composition containing the polymer |
DE60024605T2 (de) * | 1999-03-23 | 2006-08-24 | Carnegie Mellon University | Katalytische prozesse für die kontrollierte polymerisation von freiradikalischen, copolymerisierbaren monomeren und funktionellpolymersysteme hergestellt davon |
EP1197498B1 (en) | 1999-04-02 | 2006-03-22 | Kaneka Corporation | Method of treating polymer |
WO2001059011A1 (fr) | 2000-02-08 | 2001-08-16 | Kaneka Corporation | Compositions durcissables |
EP1205492A1 (en) | 2000-11-08 | 2002-05-15 | ETHZ, Laboratorium für Technische Chemie LTC | Process for producing homo- and co-polymers by RAFT miniemulsion polymerization |
EP1510550A4 (en) | 2002-05-31 | 2005-11-16 | Asahi Denka Co Ltd | ACRYLSOLZUSAMMENSETZUNG |
US20050113543A1 (en) | 2002-06-03 | 2005-05-26 | Koberstein Jeffrey T. | Alpha, omega-allyl terminated linear poly(methacrylic acid) macromonomers for end-linked hydrogels and method of preparation |
DE10350786A1 (de) | 2003-10-29 | 2005-06-02 | Röhm GmbH & Co. KG | Mischungen zur Herstellung von Reaktivschmelzklebstoffen sowie daraus erhältliche Reaktivschmelzklebstoffe |
DE102006015846A1 (de) | 2006-04-03 | 2007-10-04 | Röhm Gmbh | Kupferentfernung aus ATRP-Produkten mittels Zugabe von Schwefelverbindungen |
DE102006037350A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von halogenfreien ATRP-Produkten |
DE102006037351A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von hydroxytelecheler ATRP-Produkten |
DE102006037352A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von säureterminierten ATRP-Produkten |
DE102006048154A1 (de) | 2006-10-10 | 2008-04-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von silyltelechelen Polymeren |
-
2008
- 2008-05-28 DE DE102008002016A patent/DE102008002016A1/de not_active Withdrawn
-
2009
- 2009-04-14 US US12/992,430 patent/US8431652B2/en not_active Expired - Fee Related
- 2009-04-14 JP JP2011510918A patent/JP5661611B2/ja not_active Expired - Fee Related
- 2009-04-14 AU AU2009253311A patent/AU2009253311A1/en not_active Abandoned
- 2009-04-14 KR KR1020107026535A patent/KR20110030438A/ko not_active Application Discontinuation
- 2009-04-14 EP EP09753737.7A patent/EP2285849B1/de not_active Not-in-force
- 2009-04-14 WO PCT/EP2009/054364 patent/WO2009144082A1/de active Application Filing
- 2009-04-14 CN CN201510092308.8A patent/CN104710585A/zh active Pending
- 2009-04-14 CA CA2725584A patent/CA2725584A1/en not_active Abandoned
- 2009-04-14 CN CN200980119477.9A patent/CN102046678A/zh active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001200026A (ja) * | 1999-11-12 | 2001-07-24 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体の製法およびその製法で得られたブロック共重合体 |
JP2002060449A (ja) * | 2000-08-11 | 2002-02-26 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体を含有する硬化性組成物 |
WO2002092696A1 (fr) * | 2001-05-14 | 2002-11-21 | Kaneka Corporation | Composition de resine thermoplastique |
JP2002338625A (ja) * | 2001-05-14 | 2002-11-27 | Kanegafuchi Chem Ind Co Ltd | ブロック共重合体 |
JP2009509014A (ja) * | 2005-09-22 | 2009-03-05 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | (メタ)アクリレートベースのaba−トリブロックコポリマーの製造方法 |
WO2008021500A2 (en) * | 2006-08-17 | 2008-02-21 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Modification of surfaces with polymers |
JP2010539265A (ja) * | 2007-09-12 | 2010-12-16 | コンストラクション リサーチ アンド テクノロジー ゲーエムベーハー | シラン変性コポリマーの製造方法 |
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JP7239901B2 (ja) | 2018-04-27 | 2023-03-15 | 東亞合成株式会社 | 硬化性樹脂組成物、並びに、ブロック共重合体及びその製造方法 |
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CA2725584A1 (en) | 2009-12-03 |
US20110086984A1 (en) | 2011-04-14 |
US8431652B2 (en) | 2013-04-30 |
WO2009144082A1 (de) | 2009-12-03 |
EP2285849A1 (de) | 2011-02-23 |
CN102046678A (zh) | 2011-05-04 |
KR20110030438A (ko) | 2011-03-23 |
AU2009253311A1 (en) | 2009-12-03 |
DE102008002016A1 (de) | 2009-12-03 |
EP2285849B1 (de) | 2014-06-18 |
JP5661611B2 (ja) | 2015-01-28 |
CN104710585A (zh) | 2015-06-17 |
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