JP5675586B2 - 生分解可能なポリエステルを連続的に製造する方法 - Google Patents
生分解可能なポリエステルを連続的に製造する方法 Download PDFInfo
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- JP5675586B2 JP5675586B2 JP2011504419A JP2011504419A JP5675586B2 JP 5675586 B2 JP5675586 B2 JP 5675586B2 JP 2011504419 A JP2011504419 A JP 2011504419A JP 2011504419 A JP2011504419 A JP 2011504419A JP 5675586 B2 JP5675586 B2 JP 5675586B2
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- Prior art keywords
- acid
- component
- mixture
- aliphatic
- phosphate
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- 238000000034 method Methods 0.000 title claims description 29
- 229920000229 biodegradable polyester Polymers 0.000 title claims description 17
- 239000004622 biodegradable polyester Substances 0.000 title claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 46
- 229920000728 polyester Polymers 0.000 claims description 45
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 34
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 22
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 20
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 18
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 8
- 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 claims description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 7
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 claims description 6
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 6
- 150000001718 carbodiimides Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011552 falling film Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 claims description 4
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 claims description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 3
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 3
- 229960002684 aminocaproic acid Drugs 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 229910001382 calcium hypophosphite Inorganic materials 0.000 claims description 2
- 229940064002 calcium hypophosphite Drugs 0.000 claims description 2
- 239000001506 calcium phosphate Substances 0.000 claims description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 2
- 235000011010 calcium phosphates Nutrition 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 claims description 2
- 150000003609 titanium compounds Chemical class 0.000 claims description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 2
- XWKBMOUUGHARTI-UHFFFAOYSA-N tricalcium;diphosphite Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])[O-].[O-]P([O-])[O-] XWKBMOUUGHARTI-UHFFFAOYSA-N 0.000 claims description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 2
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 2
- 239000003925 fat Substances 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000010936 titanium Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000012190 activator Substances 0.000 description 5
- 239000002361 compost Substances 0.000 description 5
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 4
- 229920001634 Copolyester Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 229920003232 aliphatic polyester Polymers 0.000 description 4
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
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- 229920000747 poly(lactic acid) Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 2
- KKKKCPPTESQGQH-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=NCCO1 KKKKCPPTESQGQH-UHFFFAOYSA-N 0.000 description 2
- QEEZSWGDNCHFKC-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-ylmethyl)-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CC1=NCCO1 QEEZSWGDNCHFKC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KFNAHVKJFHDCSK-UHFFFAOYSA-N 2-[2-(4,5-dihydro-1,3-oxazol-2-yl)ethyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCC1=NCCO1 KFNAHVKJFHDCSK-UHFFFAOYSA-N 0.000 description 2
- XRMPKRMBDKCXII-UHFFFAOYSA-N 2-[3-(4,5-dihydro-1,3-oxazol-2-yl)propyl]-4,5-dihydro-1,3-oxazole Chemical compound N=1CCOC=1CCCC1=NCCO1 XRMPKRMBDKCXII-UHFFFAOYSA-N 0.000 description 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- SIDXWBLTDUJVLZ-UHFFFAOYSA-N n'-(2-methylphenyl)-n-octadecylmethanediimine Chemical compound CCCCCCCCCCCCCCCCCCN=C=NC1=CC=CC=C1C SIDXWBLTDUJVLZ-UHFFFAOYSA-N 0.000 description 1
- GICIQDIJBUWIEW-UHFFFAOYSA-N n'-benzylmethanediimine Chemical compound N=C=NCC1=CC=CC=C1 GICIQDIJBUWIEW-UHFFFAOYSA-N 0.000 description 1
- QNUWNUVBCQVXQV-UHFFFAOYSA-N n'-decylmethanediimine Chemical compound CCCCCCCCCCN=C=N QNUWNUVBCQVXQV-UHFFFAOYSA-N 0.000 description 1
- SQEHYBILZVXINP-UHFFFAOYSA-N n'-tert-butyl-n-propan-2-ylmethanediimine Chemical compound CC(C)N=C=NC(C)(C)C SQEHYBILZVXINP-UHFFFAOYSA-N 0.000 description 1
- JCNCSCMYYGONLU-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NC1=CC=CC=C1C JCNCSCMYYGONLU-UHFFFAOYSA-N 0.000 description 1
- JEQPWXGHMRFTRF-UHFFFAOYSA-N n,n'-bis(2-methylpropyl)methanediimine Chemical compound CC(C)CN=C=NCC(C)C JEQPWXGHMRFTRF-UHFFFAOYSA-N 0.000 description 1
- NASVTBDJHWPMOO-UHFFFAOYSA-N n,n'-dimethylmethanediimine Chemical compound CN=C=NC NASVTBDJHWPMOO-UHFFFAOYSA-N 0.000 description 1
- ATYQZACNIHLXIS-UHFFFAOYSA-N n,n'-dinaphthalen-2-ylmethanediimine Chemical compound C1=CC=CC2=CC(N=C=NC3=CC4=CC=CC=C4C=C3)=CC=C21 ATYQZACNIHLXIS-UHFFFAOYSA-N 0.000 description 1
- NWBVGPKHJHHPTA-UHFFFAOYSA-N n,n'-dioctylmethanediimine Chemical compound CCCCCCCCN=C=NCCCCCCCC NWBVGPKHJHHPTA-UHFFFAOYSA-N 0.000 description 1
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 1
- IDVWLLCLTVBSCS-UHFFFAOYSA-N n,n'-ditert-butylmethanediimine Chemical compound CC(C)(C)N=C=NC(C)(C)C IDVWLLCLTVBSCS-UHFFFAOYSA-N 0.000 description 1
- LEWFYLHNCUJXQT-UHFFFAOYSA-N n-benzyl-n'-(2-methylphenyl)methanediimine Chemical compound CC1=CC=CC=C1N=C=NCC1=CC=CC=C1 LEWFYLHNCUJXQT-UHFFFAOYSA-N 0.000 description 1
- VQMQCAXAELDDRE-UHFFFAOYSA-N n-benzyl-n'-phenylmethanediimine Chemical compound C=1C=CC=CC=1CN=C=NC1=CC=CC=C1 VQMQCAXAELDDRE-UHFFFAOYSA-N 0.000 description 1
- ATQZPTJEJUAUPY-UHFFFAOYSA-N n-octadecyl-n'-phenylmethanediimine Chemical compound CCCCCCCCCCCCCCCCCCN=C=NC1=CC=CC=C1 ATQZPTJEJUAUPY-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/785—Preparation processes characterised by the apparatus used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/247—Suited for forming thin films
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08154537.8 | 2008-04-15 | ||
| EP08154537 | 2008-04-15 | ||
| PCT/EP2009/054114 WO2009127555A1 (de) | 2008-04-15 | 2009-04-07 | Verfahren zur kontinuierlichen herstellung von biologisch abbaubaren polyestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011516708A JP2011516708A (ja) | 2011-05-26 |
| JP2011516708A5 JP2011516708A5 (enExample) | 2012-05-31 |
| JP5675586B2 true JP5675586B2 (ja) | 2015-02-25 |
Family
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| JP2011504419A Expired - Fee Related JP5675586B2 (ja) | 2008-04-15 | 2009-04-07 | 生分解可能なポリエステルを連続的に製造する方法 |
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| Country | Link |
|---|---|
| US (1) | US20110034662A1 (enExample) |
| EP (2) | EP2628758B1 (enExample) |
| JP (1) | JP5675586B2 (enExample) |
| KR (1) | KR20110007186A (enExample) |
| CN (1) | CN102007160B (enExample) |
| WO (1) | WO2009127555A1 (enExample) |
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| CA2737582C (en) | 2008-09-29 | 2018-05-15 | Basf Se | Method for coating paper |
| BRPI0919438A2 (pt) * | 2008-09-29 | 2015-12-15 | Basf Se | mistura de poliésteres, e, uso das misturas de poliésteres |
| EP2331634B1 (de) | 2008-09-29 | 2016-12-14 | Basf Se | Biologisch abbaubare polymermischung |
| JP5858786B2 (ja) | 2008-09-29 | 2016-02-10 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 脂肪族ポリエステル |
| WO2010069804A1 (de) | 2008-12-19 | 2010-06-24 | Basf Se | Verfahren zur herstellung eines verbundbauteils durch mehrkomponentenspritzguss |
| BR112012008514A2 (pt) | 2009-10-15 | 2016-04-05 | Basf Se | processo para a produção contínua de misturas de poliéster |
| IT1399031B1 (it) * | 2009-11-05 | 2013-04-05 | Novamont Spa | Copoliestere alifatico-aromatico biodegradabile |
| BR112012010877A2 (pt) | 2009-11-09 | 2016-04-05 | Basf Se | processo para a produção de filmes com encolhimento |
| US9212270B2 (en) | 2010-01-14 | 2015-12-15 | Basf Se | Method for producing expandable granulates containing polylactic acid |
| US8604101B2 (en) | 2010-03-24 | 2013-12-10 | Basf Se | Process for producing aqueous dispersions of thermoplastic polyesters |
| US20110237750A1 (en) * | 2010-03-24 | 2011-09-29 | Basf Se | Process for film production |
| JP2013527263A (ja) * | 2010-03-24 | 2013-06-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 熱可塑性ポリエステルの水性分散液の製造方法 |
| CA2792845A1 (en) | 2010-03-24 | 2011-09-29 | Basf Se | Process for producing clingfilms |
| US20110237743A1 (en) * | 2010-03-24 | 2011-09-29 | Basf Se | Process for producing clingfilms |
| CA2792699A1 (en) | 2010-03-24 | 2011-09-29 | Basf Se | Process for film production |
| JP2013542292A (ja) | 2010-10-27 | 2013-11-21 | ビーエーエスエフ ソシエタス・ヨーロピア | スリットフィルムテープを製造するためのポリマー混合物の使用 |
| US8546472B2 (en) | 2011-03-23 | 2013-10-01 | Basf Se | Polyesters based on 2-methylsuccinic acid |
| EP2688956A1 (de) | 2011-03-23 | 2014-01-29 | Basf Se | Polyester auf basis von 2-methylbernsteinsaeure |
| US9156943B2 (en) * | 2011-04-26 | 2015-10-13 | Taiwan Textile Research Institute | Modified polyesters and processes for manufacturing the same |
| US9334360B2 (en) | 2011-07-15 | 2016-05-10 | Sabic Global Technologies B.V. | Color-stabilized biodegradable aliphatic-aromatic copolyesters, methods of manufacture, and articles thereof |
| US8933162B2 (en) * | 2011-07-15 | 2015-01-13 | Saudi Basic Industries Corporation | Color-stabilized biodegradable aliphatic-aromatic copolyesters, methods of manufacture, and articles thereof |
| US8946345B2 (en) | 2011-08-30 | 2015-02-03 | Saudi Basic Industries Corporation | Method for the preparation of (polybutylene-co-adipate terephthalate) through the in situ phosphorus containing titanium based catalyst |
| EP2573142A1 (de) | 2011-09-21 | 2013-03-27 | Basf Se | Thermoplastische Formmasse mit verbesserter Kerbschlagzähigkeit |
| EP2573138A1 (de) | 2011-09-21 | 2013-03-27 | Basf Se | Polyamid-Formmassen |
| ES2537988T3 (es) | 2012-02-17 | 2015-06-16 | Sociedad Anónima Minera Catalano-Aragonesa | Poliestereteramida biodegradable |
| DE102012003417A1 (de) * | 2012-02-17 | 2013-08-22 | Uhde Inventa-Fischer Gmbh | Verfahren zur Herstellung eines hochmolekularen, heteroaromatischen Polyesters oder Copolyesters |
| US9034983B2 (en) | 2012-03-01 | 2015-05-19 | Saudi Basic Industries Corporation | Poly(butylene-co-adipate terephthalate), method of manufacture and uses thereof |
| US9540661B2 (en) | 2012-07-09 | 2017-01-10 | Basf Se | Method for the complete anaerobic digestion of polymer mixtures |
| WO2014009176A1 (de) | 2012-07-10 | 2014-01-16 | Basf Se | Verfahren zum vollständigen anaeroben abbau von polymermischungen |
| WO2014029645A2 (de) | 2012-08-24 | 2014-02-27 | Basf Se | Verwendung von polymermischungen zur herstellung von kartuschen, pipetten, cuvetten oder pipettenhalter |
| KR101992391B1 (ko) | 2012-09-04 | 2019-09-30 | (주)새한폴리머 | 생분해성 지방족/방향족 폴리에스테르 공중합체의 연속 제조방법 |
| KR20140031011A (ko) * | 2012-09-04 | 2014-03-12 | 삼성정밀화학 주식회사 | 생분해성 지방족 폴리에스테르의 연속 제조방법 |
| ES2599165T3 (es) | 2012-10-29 | 2017-01-31 | Uhde Inventa-Fischer Gmbh | Procedimiento para la preparación de un poliéster o un copoliéster de alto peso molecular así como mezclas poliméricas que los contienen |
| KR20140076354A (ko) * | 2012-12-12 | 2014-06-20 | 삼성정밀화학 주식회사 | 생분해성 지방족/방향족 폴리에스테르 공중합체의 연속 제조방법 |
| KR20140076355A (ko) | 2012-12-12 | 2014-06-20 | 삼성정밀화학 주식회사 | 생분해성 지방족/방향족 폴리에스테르 공중합체의 연속 제조방법 |
| JP2014114417A (ja) * | 2012-12-12 | 2014-06-26 | Mitsubishi Chemicals Corp | 脂肪族ポリエステル |
| KR101992392B1 (ko) * | 2012-12-12 | 2019-09-30 | (주)새한폴리머 | 생분해성 지방족/방향족 폴리에스테르 공중합체의 연속 제조방법 |
| KR20140143045A (ko) * | 2013-06-05 | 2014-12-15 | 삼성정밀화학 주식회사 | 생분해성 폴리에스테르 수지 및 이를 포함하는 물품 |
| CN103408739B (zh) * | 2013-08-08 | 2016-01-06 | 山东汇盈新材料科技有限公司 | 低端羧基含量聚己二酸-对苯二甲酸丁二醇酯的制备方法 |
| US20160326305A1 (en) * | 2013-12-30 | 2016-11-10 | Lotte Fine Chemical Co., Ltd. | Composition for producing biodegradable polyester resin, and production method for biodegradable polyester resin |
| DK3467005T3 (da) | 2016-05-30 | 2020-09-28 | Sa Minera Catalano Aragonesa | Fremgangsmåde til opnåelse af bionedbrydeligt polyesteretheramid |
| TWI609919B (zh) * | 2016-11-24 | 2018-01-01 | 共聚彈性體之製備方法及其應用 | |
| DE102017128847A1 (de) | 2016-12-08 | 2018-06-14 | Basf Se | Biologisch abbaubare Fußbekleidung basierend auf Polymilchsäure |
| JP2018145413A (ja) * | 2017-03-02 | 2018-09-20 | 三菱ケミカル株式会社 | 脂肪族芳香族ポリエステルの製造方法 |
| ES2876266T5 (en) | 2017-05-31 | 2025-03-05 | Basf Se | Aliphatic-aromatic polyesters having an increased white level index |
| CN110869414A (zh) | 2017-07-06 | 2020-03-06 | 德希尼布吉玛股份有限公司 | 使用添加剂制备聚酯的方法 |
| WO2019096918A1 (de) | 2017-11-20 | 2019-05-23 | Basf Se | Kontinuierliches verfahren zur herstellung eines aliphatischen polyesters |
| WO2019096920A1 (de) | 2017-11-20 | 2019-05-23 | Basf Se | Verfahren zur reinigung eines aliphatischen polyesters |
| JP7600136B2 (ja) * | 2019-03-19 | 2024-12-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 少なくとも２種の目標生成物の組合せ製造方法 |
| KR101992393B1 (ko) * | 2019-04-03 | 2019-06-24 | (주)새한폴리머 | 생분해성 지방족 폴리에스테르의 연속 제조방법 |
| WO2020234294A1 (en) | 2019-05-22 | 2020-11-26 | Basf Se | Continuous process for producing an aliphatic-aromatic polyester |
| WO2020234293A1 (en) | 2019-05-22 | 2020-11-26 | Basf Se | Process for purifying an aliphatic-aromatic polyester |
| CN114479039B (zh) * | 2020-10-26 | 2024-11-29 | 中国石油化工股份有限公司 | 一种耐水解聚酯催化剂及其制备方法和应用 |
| CN112280026B (zh) * | 2020-12-31 | 2021-03-09 | 江苏金发科技新材料有限公司 | 一种半芳香族聚酯及其制备方法和应用 |
| IT202100002135A1 (it) * | 2021-02-02 | 2022-08-02 | Novamont Spa | Poliesteri ramificati per extrusion coating |
| CN112940233B (zh) * | 2021-04-13 | 2021-12-07 | 四川大学 | 一种高熔点生物可降解共聚酯及其制备方法 |
| CN113354799B (zh) * | 2021-04-26 | 2022-07-05 | 浙江恒逸石化研究院有限公司 | 一种长链支化可降解聚酯及其制备方法 |
| CN113717356B (zh) * | 2021-09-14 | 2023-04-07 | 珠海万通化工有限公司 | 一种半芳香族聚酯及其制备方法和应用 |
| US20230124025A1 (en) | 2021-09-27 | 2023-04-20 | University Of Massachusetts | Compositions and methods for biodegradable, biomass-based polyesters |
| CN116023636B (zh) * | 2021-10-26 | 2025-03-25 | 江苏金发科技新材料有限公司 | 一种半芳香族聚酯及其制备方法和应用 |
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| WO2024074562A1 (en) | 2022-10-06 | 2024-04-11 | Basf Se | Thermoplastic polymer blend and use thereof |
| CN115926128B (zh) * | 2022-12-08 | 2025-07-11 | 金发科技股份有限公司 | 一种脂肪族-芳香族聚酯组合物、聚酯纤维及其制备方法和应用 |
| KR20240177276A (ko) * | 2023-06-19 | 2024-12-27 | 코오롱인더스트리 주식회사 | 생분해성 폴리에스테르 수지 및 이의 제조 방법 |
| CN117887048B (zh) * | 2023-12-29 | 2025-07-15 | 金发科技股份有限公司 | 一种可生物降解脂肪族聚酯及其制备方法和应用 |
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| SG47853A1 (en) | 1990-11-30 | 1998-04-17 | Eastman Chem Co | Aliphatic-aromatic copolyesters and cellulose ester/polymer blend |
| DE4430634A1 (de) * | 1994-08-29 | 1996-03-07 | Hoechst Ag | Verfahren zur Herstellung thermostabiler, farbneutraler, antimonfreier Polyester und die danach herstellbaren Produkte |
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| DE59505196D1 (de) | 1994-12-30 | 1999-04-08 | Fischer Karl Ind Gmbh | Reaktorvorrichtung für fliessfähige und höherviskose Medien |
| DE19500757A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| JPH11236442A (ja) * | 1998-02-20 | 1999-08-31 | Nippon Ester Co Ltd | ポリエステルの製造方法 |
| EP1046662B1 (en) * | 1999-04-22 | 2003-03-12 | Zimmer Aktiengesellschaft | Process of producing polytrimethylene terephthalate (PTT) |
| JP2000309631A (ja) * | 1999-04-27 | 2000-11-07 | Toray Ind Inc | ポリエステルの製造方法 |
| DE19929790A1 (de) | 1999-06-29 | 2001-01-04 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Polybutylenterephthalat aus Terephthalsäure und Butandiol |
| JP2003073466A (ja) * | 2001-06-19 | 2003-03-12 | Toray Ind Inc | ポリブチレンテレフタレートの製造法 |
| DE10155419B4 (de) | 2001-11-12 | 2005-06-16 | Inventa-Fischer Gmbh & Co. Kg | Verfahren zur kontinuierlichen Herstellung von hochmolekularem Polyester sowie Vorrichtung zur Durchführung des Verfahrens |
| JP3996876B2 (ja) * | 2002-06-24 | 2007-10-24 | 三菱化学株式会社 | ポリエステル樹脂の製造方法 |
| DE10246251A1 (de) * | 2002-10-02 | 2004-04-15 | Zimmer Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Polyestern |
| DE10351085A1 (de) | 2003-10-31 | 2005-06-16 | Inventa-Fischer Gmbh & Co. Kg | Turmreaktor sowie dessen Verwendung zur kontinuierlichen Herstellung von hochmolekularem Polyester |
| EP1818352A4 (en) * | 2004-11-30 | 2011-12-21 | Asahi Kasei Chemicals Corp | POLYESTER RESIN, FORM BODY AND MANUFACTURING METHOD THEREFOR |
| DE102005053068B4 (de) | 2005-11-04 | 2017-05-11 | Basf Se | Sebazinsäurehaltige Polyester und Polyestermischung, Verfahren zu deren Herstellung sowie ein Verzweigerbatch und die Verwendung der Polyestermischung |
| WO2007088074A1 (en) * | 2006-02-03 | 2007-08-09 | Saudi Basic Industries Corporation | Process for the preparation of polyethylene terephthalate |
| DE102006025942B4 (de) * | 2006-06-02 | 2011-07-07 | Uhde Inventa-Fischer GmbH & Co. KG, 13509 | Verfahren zur kontinuierlichen Herstellung von hochmolekularen Polyestern durch Veresterung von Dicarbonsäuren und/oder Umesterung von Dicarbonsäuren mit Diolen und/oder deren Mischungen sowie Vorrichtung hierzu |
| JP5176415B2 (ja) * | 2006-07-18 | 2013-04-03 | 三菱化学株式会社 | 脂肪族ポリエステルの製造方法 |
| JP5200531B2 (ja) * | 2007-12-27 | 2013-06-05 | 三菱化学株式会社 | 脂肪族ポリエステルの製造方法 |
-
2009
- 2009-04-07 WO PCT/EP2009/054114 patent/WO2009127555A1/de not_active Ceased
- 2009-04-07 CN CN2009801131002A patent/CN102007160B/zh active Active
- 2009-04-07 KR KR1020107025424A patent/KR20110007186A/ko not_active Abandoned
- 2009-04-07 EP EP13167642.1A patent/EP2628758B1/de not_active Not-in-force
- 2009-04-07 JP JP2011504419A patent/JP5675586B2/ja not_active Expired - Fee Related
- 2009-04-07 US US12/988,102 patent/US20110034662A1/en not_active Abandoned
- 2009-04-07 EP EP09732629A patent/EP2268704A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009127555A1 (de) | 2009-10-22 |
| EP2628758A1 (de) | 2013-08-21 |
| US20110034662A1 (en) | 2011-02-10 |
| KR20110007186A (ko) | 2011-01-21 |
| JP2011516708A (ja) | 2011-05-26 |
| EP2268704A1 (de) | 2011-01-05 |
| CN102007160B (zh) | 2013-05-29 |
| CN102007160A (zh) | 2011-04-06 |
| EP2628758B1 (de) | 2014-10-08 |
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