JP2000302852A5 - - Google Patents
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- Publication number
- JP2000302852A5 JP2000302852A5 JP1999117778A JP11777899A JP2000302852A5 JP 2000302852 A5 JP2000302852 A5 JP 2000302852A5 JP 1999117778 A JP1999117778 A JP 1999117778A JP 11777899 A JP11777899 A JP 11777899A JP 2000302852 A5 JP2000302852 A5 JP 2000302852A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- catalyst
- aliphatic
- ppm
- reaction
- 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
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- 239000003054 catalyst Substances 0.000 description 46
- 229920003232 aliphatic polyester Polymers 0.000 description 32
- 125000001931 aliphatic group Chemical group 0.000 description 27
- 238000006116 polymerization reaction Methods 0.000 description 22
- 239000007790 solid phase Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000018044 dehydration Effects 0.000 description 18
- 238000006297 dehydration reaction Methods 0.000 description 18
- 238000006068 polycondensation reaction Methods 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 13
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- -1 sulfonic acid compound Chemical class 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FJPATRZRCOLKEC-UHFFFAOYSA-N 4,4-bis(carboxymethyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)CC1(CC(O)=O)CCC(C(O)=O)CC1 FJPATRZRCOLKEC-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 1
- LOGBRYZYTBQBTB-UHFFFAOYSA-N butane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)CC(O)=O LOGBRYZYTBQBTB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- DTGRIEIJTWNZQF-UHFFFAOYSA-N cyclohexane-1,2,3,4,5,6-hexacarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C(C(O)=O)C(C(O)=O)C1C(O)=O DTGRIEIJTWNZQF-UHFFFAOYSA-N 0.000 description 1
- RWLDAJMGAVDXSH-UHFFFAOYSA-N ethane-1,1,2-tricarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(O)=O RWLDAJMGAVDXSH-UHFFFAOYSA-N 0.000 description 1
- IREPGQRTQFRMQR-UHFFFAOYSA-N furantetracarboxylic acid Chemical compound OC(=O)C=1OC(C(O)=O)=C(C(O)=O)C=1C(O)=O IREPGQRTQFRMQR-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001432 poly(L-lactide) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11777899A JP4139516B2 (ja) | 1998-04-28 | 1999-04-26 | ポリエステルの製造方法 |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11958198 | 1998-04-28 | ||
| JP28429198 | 1998-10-06 | ||
| JP36953698 | 1998-12-25 | ||
| JP10-284291 | 1999-02-17 | ||
| JP10-119581 | 1999-02-17 | ||
| JP3829099 | 1999-02-17 | ||
| JP10-369536 | 1999-02-17 | ||
| JP11-38290 | 1999-02-17 | ||
| JP11777899A JP4139516B2 (ja) | 1998-04-28 | 1999-04-26 | ポリエステルの製造方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008074076A Division JP4421657B2 (ja) | 1998-04-28 | 2008-03-21 | ポリエステルの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2000302852A JP2000302852A (ja) | 2000-10-31 |
| JP2000302852A5 true JP2000302852A5 (enrdf_load_stackoverflow) | 2006-03-02 |
| JP4139516B2 JP4139516B2 (ja) | 2008-08-27 |
Family
ID=27521935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11777899A Expired - Lifetime JP4139516B2 (ja) | 1998-04-28 | 1999-04-26 | ポリエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4139516B2 (enrdf_load_stackoverflow) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5291273B2 (ja) * | 1999-07-09 | 2013-09-18 | 三井化学株式会社 | 脂肪族ポリエステルの製造方法 |
| JP4651802B2 (ja) * | 1999-10-27 | 2011-03-16 | 三井化学株式会社 | 安定性に優れた脂肪族ポリエステルの製造方法 |
| JP4612239B2 (ja) * | 2001-07-18 | 2011-01-12 | 三井化学株式会社 | 生体吸収性ポリヒドロキシカルボン酸の製造方法 |
| EP1440992A1 (fr) * | 2003-01-21 | 2004-07-28 | Société de Conseils de Recherches et d'Applications Scientifiques ( S.C.R.A.S.) | Système catalytique de (co)polymérisation du lactide et du glycolide |
| WO2009142196A1 (ja) | 2008-05-21 | 2009-11-26 | 東レ株式会社 | 脂肪族ポリエステル樹脂の製造方法および脂肪族ポリエステル樹脂組成物 |
| US20120095169A1 (en) | 2009-06-30 | 2012-04-19 | Ryohei Ogawa | Polylactic acid-based resin, process for producing polylactic acid-based resin, polylactic acid resin composition, stereocomplex polylactic acid resin composition and process for producing stereocomplex polylactic acid resin composition |
| JP5737182B2 (ja) * | 2010-09-28 | 2015-06-17 | 東レ株式会社 | ポリ乳酸系樹脂の製造方法 |
| FR2967415B1 (fr) * | 2010-11-15 | 2012-11-30 | Ipsen Pharma Sas | Procede de preparation de polymeres etoiles |
| JP5858387B2 (ja) * | 2011-02-02 | 2016-02-10 | 国立大学法人 名古屋工業大学 | 有機触媒によるポリエステル合成方法 |
| JP2012188464A (ja) * | 2011-03-08 | 2012-10-04 | Asahi Kasei Chemicals Corp | 脂肪族ポリヒドロキシカルボン酸及びその製造方法 |
| CN102807671A (zh) | 2011-05-31 | 2012-12-05 | 东丽纤维研究所（中国）有限公司 | 一种制备高分子量脂肪族聚酯的固相聚合方法 |
| US9080008B2 (en) | 2011-07-28 | 2015-07-14 | Toray Industries, Inc. | Polylactic acid resin and method for producing same |
-
1999
- 1999-04-26 JP JP11777899A patent/JP4139516B2/ja not_active Expired - Lifetime
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