KR20050039675A - 방향족 아미드 블록 공중합체 및 그 제조 방법 - Google Patents
방향족 아미드 블록 공중합체 및 그 제조 방법 Download PDFInfo
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- KR20050039675A KR20050039675A KR1020040085070A KR20040085070A KR20050039675A KR 20050039675 A KR20050039675 A KR 20050039675A KR 1020040085070 A KR1020040085070 A KR 1020040085070A KR 20040085070 A KR20040085070 A KR 20040085070A KR 20050039675 A KR20050039675 A KR 20050039675A
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- South Korea
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- compound
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- poly
- aromatic amide
- residues
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- 150000008430 aromatic amides Chemical class 0.000 title claims abstract description 86
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title description 14
- 230000008569 process Effects 0.000 title description 3
- -1 aromatic amide compound Chemical group 0.000 claims abstract description 224
- 239000004793 Polystyrene Substances 0.000 claims abstract description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 5
- 229920002223 polystyrene Polymers 0.000 claims abstract description 5
- 150000001875 compounds Chemical group 0.000 claims description 64
- 150000003077 polyols Chemical group 0.000 claims description 61
- 229920005862 polyol Polymers 0.000 claims description 46
- 239000004970 Chain extender Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 230000001588 bifunctional effect Effects 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 20
- 229920000728 polyester Polymers 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 150000002430 hydrocarbons Chemical group 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 125000005375 organosiloxane group Chemical group 0.000 claims description 7
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
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- 239000000243 solution Substances 0.000 description 36
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 21
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- 150000001993 dienes Chemical group 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 8
- 229920001610 polycaprolactone Chemical group 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- 239000002685 polymerization catalyst Substances 0.000 description 8
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical group O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 7
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000002009 diols Chemical group 0.000 description 7
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 7
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GVKORIDPEBYOFR-UHFFFAOYSA-K [butyl-bis(2-ethylhexanoyloxy)stannyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)O[Sn](CCCC)(OC(=O)C(CC)CCCC)OC(=O)C(CC)CCCC GVKORIDPEBYOFR-UHFFFAOYSA-K 0.000 description 6
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000009864 tensile test Methods 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- IOGGBUVFUGPCLQ-UHFFFAOYSA-N 1-[4-(2-oxoazepane-1-carbonyl)benzoyl]azepan-2-one Chemical compound C=1C=C(C(=O)N2C(CCCCC2)=O)C=CC=1C(=O)N1CCCCCC1=O IOGGBUVFUGPCLQ-UHFFFAOYSA-N 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
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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 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical group O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
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- 239000011541 reaction mixture Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical group O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 description 3
- RNQBCZCPNUHWLV-UHFFFAOYSA-N 1,8-dioxacyclotetradecane-2,7-dione Chemical group O=C1CCCCC(=O)OCCCCCCO1 RNQBCZCPNUHWLV-UHFFFAOYSA-N 0.000 description 3
- UHQZGWJEFFDHSR-UHFFFAOYSA-N 1-(2-oxoazepane-1-carbonyl)azepan-2-one Chemical compound C1CCCCC(=O)N1C(=O)N1CCCCCC1=O UHQZGWJEFFDHSR-UHFFFAOYSA-N 0.000 description 3
- HXZRLUTUNSQNCG-UHFFFAOYSA-N 1-[3-(2-oxoazepane-1-carbonyl)benzoyl]azepan-2-one Chemical compound C=1C=CC(C(=O)N2C(CCCCC2)=O)=CC=1C(=O)N1CCCCCC1=O HXZRLUTUNSQNCG-UHFFFAOYSA-N 0.000 description 3
- SPEHEHYVDRYEDX-UHFFFAOYSA-N 3-methyloxan-2-one Chemical group CC1CCCOC1=O SPEHEHYVDRYEDX-UHFFFAOYSA-N 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229960000380 propiolactone Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 description 2
- ANLVEXKNRYNLDH-UHFFFAOYSA-N 1,3-dioxonan-2-one Chemical compound O=C1OCCCCCCO1 ANLVEXKNRYNLDH-UHFFFAOYSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- KRPHHCIWLYCQHY-UHFFFAOYSA-N 1,4-bis(2-oxoazepan-1-yl)butane-1,4-dione Chemical compound C1CCCCC(=O)N1C(=O)CCC(=O)N1CCCCCC1=O KRPHHCIWLYCQHY-UHFFFAOYSA-N 0.000 description 2
- LBIFWKFJCOUADQ-UHFFFAOYSA-N 1-(4-aminobenzoyl)azepan-2-one Chemical compound C1=CC(N)=CC=C1C(=O)N1C(=O)CCCCC1 LBIFWKFJCOUADQ-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- CIABOKKWRWAZRS-UHFFFAOYSA-N 1-n,4-n-bis[4-(1-hydroxypropan-2-yloxy)phenyl]benzene-1,4-dicarboxamide Chemical compound C1=CC(OC(CO)C)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(OC(C)CO)=CC=2)C=C1 CIABOKKWRWAZRS-UHFFFAOYSA-N 0.000 description 2
- JRGIQVOUTAGJJA-UHFFFAOYSA-N 1-n,4-n-bis[4-(2-hydroxyethoxy)phenyl]benzene-1,4-dicarboxamide Chemical compound C1=CC(OCCO)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(OCCO)=CC=2)C=C1 JRGIQVOUTAGJJA-UHFFFAOYSA-N 0.000 description 2
- VBFBNFABWFQYPL-UHFFFAOYSA-N 1-n,4-n-bis[4-(2-hydroxypropoxy)phenyl]benzene-1,4-dicarboxamide Chemical compound C1=CC(OCC(O)C)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(OCC(C)O)=CC=2)C=C1 VBFBNFABWFQYPL-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- ASKDNKAURXFDOL-UHFFFAOYSA-N 4-(sulfinylamino)benzoyl chloride Chemical compound ClC(=O)C1=CC=C(N=S=O)C=C1 ASKDNKAURXFDOL-UHFFFAOYSA-N 0.000 description 2
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical group C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PHLZDCSVSDSPPH-UHFFFAOYSA-N pentanedioyl dibromide Chemical compound BrC(=O)CCCC(Br)=O PHLZDCSVSDSPPH-UHFFFAOYSA-N 0.000 description 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003199 poly(diethylsiloxane) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-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
- GKIVTXLMSMDQJI-UHFFFAOYSA-N propanedioyl dibromide Chemical compound BrC(=O)CC(Br)=O GKIVTXLMSMDQJI-UHFFFAOYSA-N 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyamides (AREA)
Abstract
Description
Claims (7)
- 하기 일반식(1)로 나타내는 방향족 아미드 화합물 단위, 하기 일반식(2) 및/또는 (3)으로 나타내는 구조 단위를 포함하여 이루어지고, 겔 투과 크로마토그래피로 측정된 표준 폴리스티렌 환산 중량 평균 분자량이 10,000~1,000,000인 것을 특징으로 하는 방향족 아미드 블록 공중합체:(1)여기에서, R1과 R2는 각각 독립적으로 탄소수 1~20의 2가 알킬렌기를 나타내고; Ar1과 Ar2는 각각 독립적으로 탄소수 6~20의 2가 아릴렌기를 나타낸다.-G1-X-G2- (2)-X-G3-X- (3)여기에서, G1과 G2는 폴리에스테르 잔기를 나타내고; G3는 디올 화합물 잔기 또는 폴리올 화합물 잔기를 나타내고; X는 하기 일반식(4)~(5)로 나타낸 군으로부터 선택된 1종 이상의 사슬 연장 성분 단위를 나타낸다:(4)여기에서, R3는 각각 독립적으로 탄소수 2~20의 2가 알킬렌기를 나타내고;R4는 카르보닐기 또는 탄소수 2~20의 2가 유기기를 나타내고;p와 q는 각각 0 또는 1을 나타내고,(5)여기에서 R5는 탄소수 2~20의 2가 탄화수소기를 나타낸다.
- 제 1 항에 있어서, 일반식(2)에서, G1과 G2로 나타낸 상기 폴리에스테르 잔기가 폴리락톤잔기인 것을 특징으로 하는 방향족 아미드 블록 공중합체.
- 제 1 항에 있어서, 일반식(3)에서, G3로 나타낸 디올 화합물 잔기 또는 폴리올 화합물 잔기가 폴리(옥시알킬렌)계 폴리올 잔기, 폴리(오가노실록산)계 폴리올 잔기, 지방족 탄화수소계 디올 잔기, 지방족 탄화수소계 폴리올 잔기, 지환식 탄화수소계 폴리올 잔기, 폴리에스테르계 폴리올 잔기, 폴리카르보네이트계 폴리올 잔기 및 폴리(비닐 에테르)계 폴리올 잔기를 구성하는 군으로부터 선택된 1종 이상의 디올 화합물 잔기 또는 폴리올 화합물 잔기인 것을 특징으로 하는 방향족 아미드 블록 공중합체.
- 하기 일반식(6)으로 나타낸 디히드록시 방향족 아미드 화합물의 존재하에서, 하기 일반식(7)로 나타내는 락톤 화합물을 가열 개환 중합 하여 얻은 폴리락톤과 사슬연장제를 반응시키는 단계를 포함하여 이루어지는 하는 제 1항 또는 제 2 항에 기재된 방향족 아미드 블록 공중합체의 제조 방법:(6)여기에 R6과 R7은 각각 독립적으로 탄소수 1~20의 2가 알킬렌기를 나타내고; Ar3과 Ar4는 각각 독립적으로 탄소수 6~20의 2가 아릴렌기를 나타낸다.(7)여기에 R8은 탄소수 2~20의 2가 지방족 탄화수소기를 나타낸다:
- 하기 일반식(6)으로 나타내는 디히드록시 방향족 아미드 화합물과 하기 일반식(8)로 나타내는 디올 화합물 또는 폴리올 화합물과 사슬연장제를 반응시키는 단계를 포함하여 이루어지는 제 1 항 또는 제 3 항에 기재된 방향족 아미드 블록 공중합체의 제조방법:(6)여기에 R6과 R7은 각각 독립적으로 탄소수 1~20의 2가 알킬렌기를 나타내고; Ar3과 Ar4는 각각 독립적으로 탄소수 6~20의 2가 아릴렌기를 나타낸다.HO-R9-OH (8)여기에서 R9는 폴리(옥시알킬렌), 폴리(오가노실록산), 지방족 탄화수소기, 지환식 탄화수소기, 폴리에스테르, 폴리카르보네이트 및 폴리(비닐 에테르)로 구성된 군으로부터 선택된 1종 이상의 2가 유기기를 나타낸다.
- 제 4 항에 있어서, 상기 사슬연장제는 2관능성 산 할라이드 화합물, 2관능성 이소시아네이트 화합물, 2관능성 카르보네이트 화합물, 2관능성 에스테르 화합물, 2관능성 아실락탐 화합물, 2관능성 에폭시 화합물 및 2관능성 테트라카르복시산 무수물로 구성된 군으로부터 선택된 1종 이상의 화합물인 것을 특징으로 하는 방향족 아미드 블록 공중합체의 제조방법.
- 제 5 항에 있어서, 상기 사슬 연장제는 2관능성 산 할라이드 화합물, 2관능성 이소시아네이트 화합물, 2관능성 카르보네이트 화합물, 2관능성 에스테르 화합물, 2관능성 아실락탐 화합물, 2관능성 에폭시 화합물 및 2관능성 테트라카르복시산 무수물로 구성된 군으로부터 선택된 1종 이상의 화합물인 것을 특징으로 하는 제 방향족 아미드 블록 공중합체의 제조방법.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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JP2003364290 | 2003-10-24 | ||
JPJP-P-2003-00364290 | 2003-10-24 | ||
JPJP-P-2003-00375508 | 2003-11-05 | ||
JP2003375508 | 2003-11-05 | ||
JPJP-P-2004-00218645 | 2004-07-27 | ||
JP2004218645 | 2004-07-27 |
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KR20050039675A true KR20050039675A (ko) | 2005-04-29 |
KR100793195B1 KR100793195B1 (ko) | 2008-01-10 |
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Country Status (4)
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US (1) | US7129314B2 (ko) |
EP (1) | EP1526149B1 (ko) |
KR (1) | KR100793195B1 (ko) |
DE (1) | DE602004006575T2 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20200062231A (ko) * | 2017-10-16 | 2020-06-03 | 로께뜨프레르 | 디안하이드로헥시톨 디알킬카보네이트 또는 디안하이드로헥시톨 카보네이트의 이량체로부터 수득된 올리고카보네이트 폴리올, 이의 제조 방법 및 이의 용도 |
KR20200062232A (ko) * | 2017-10-16 | 2020-06-03 | 로께뜨프레르 | 올리고카보네이트 폴리올을 사용하여 합성된 다중블록 중합체 |
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DE102006016322A1 (de) * | 2006-04-06 | 2007-10-11 | Wacker Chemie Ag | Verfahren zur Herstellung von Polyamid-Polysiloxan-Blockcopolymeren |
US9562127B2 (en) | 2014-05-16 | 2017-02-07 | International Business Machines Corporation | Methods of forming block polymers for directed self-assembly |
US9574107B2 (en) | 2015-02-16 | 2017-02-21 | International Business Machines Corporation | Fluoro-alcohol additives for orientation control of block copolymers |
CN114716674B (zh) * | 2022-03-02 | 2023-07-25 | 江苏环峰电工材料有限公司 | 一种稳定性优异的线型聚合物及其应用 |
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EP0608976B1 (en) * | 1993-01-08 | 1997-11-12 | Tosoh Corporation | Esteramide copolymers and production thereof |
JP3385756B2 (ja) | 1994-11-16 | 2003-03-10 | 東ソー株式会社 | エステルアミドブロック共重合体 |
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2004
- 2004-10-04 US US10/956,088 patent/US7129314B2/en active Active
- 2004-10-13 DE DE602004006575T patent/DE602004006575T2/de active Active
- 2004-10-13 EP EP04024414A patent/EP1526149B1/en not_active Ceased
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KR20200062231A (ko) * | 2017-10-16 | 2020-06-03 | 로께뜨프레르 | 디안하이드로헥시톨 디알킬카보네이트 또는 디안하이드로헥시톨 카보네이트의 이량체로부터 수득된 올리고카보네이트 폴리올, 이의 제조 방법 및 이의 용도 |
KR20200062232A (ko) * | 2017-10-16 | 2020-06-03 | 로께뜨프레르 | 올리고카보네이트 폴리올을 사용하여 합성된 다중블록 중합체 |
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US7129314B2 (en) | 2006-10-31 |
EP1526149B1 (en) | 2007-05-23 |
DE602004006575D1 (de) | 2007-07-05 |
US20050090639A1 (en) | 2005-04-28 |
DE602004006575T2 (de) | 2008-01-31 |
KR100793195B1 (ko) | 2008-01-10 |
EP1526149A1 (en) | 2005-04-27 |
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