IP Library Granted Patent US 9,284,403
Granted Patent B2
US 9,284,403 · App. 14/343,912 · Granted Mar 15, 2016

Method to produce semi-crystalline polylactides

Inventors: Hisanori Kishida (Osaka, JP); Takashi Hasegawa (Osaka, JP); Nobuyoshi Nomura (Nagoya, JP); Makoto Takahashi (Nagoya, JP); Joseph Schroeder (Minnetonka, MN); Manuel Natal (Minnetonka, MN)
Assignees: Hitachi Zosen Corporation; Tohoku Electric Power Co., Inc.; National University Corporation Nagoya University; NatureWorks LLC
C08G63/08C08G63/823
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Quick Facts
Patent No.
US 9,284,403
App. No.
14/343,912
Granted
Mar 15, 2016
Kind
B2
Abstract

This invention provides a method for synthesizing semi-crystalline polylactides (PLA) even from a lactide mixture including meso-LA and rac-LA. According to the invention, when a mixture of racemic lactide and meso-lactide ispolymerized using a catalyst capable of iso-selectively polymerizing L-lactide and D-lactide, an amorphous poly (meso-lactide) block is formed from meso-lactide and a semi-crystalline poly (racemic lactide) block is formed from racemic lactide by separately polymerizing racemic lactide and meso-lactide by taking advantage of a difference in physicochemical properties between racemic lactide and meso-lactide, whereby polylactide which is semi-crystalline as a whole is produced.

Claims (4)

1. A method for producing semi-crystalline polylactide from a mixture of racemic lactide and meso-lactide, wherein when the mixture is polymerized using a catalyst capable of iso-selectively polymerizing L-lactide and D-lactide, an amorphous poly (meso-lactide) block is formed from meso-lactide and a semi-crystalline poly(racemic lactide) block is formed from racemic lactide by separately polymerizing racemic lactide and meso-lactide by taking advantage of a difference in physicochemical properties between racemic lactide and meso-lactide, whereby polylactide which is semi-crystalline as a whole is produced.

2. The method according to claim 1 , wherein meso-lactide and racemic lactide are separately polymerized in such a manner that meso-lactide in the mixture is polymerized by adding a small amount of a solvent to the mixture to preferentially dissolve meso-lactide having a higher solubility in the solvent, and thereafter racemic lactide is polymerized, whereby semi-crystalline polylactide is produced.

3. The method according to claim 1 , wherein meso-lactide and racemic lactide are separately polymerized in such a manner that first polymerization is performed for the mixture at a temperature in a first temperature range in which meso-lactide having a low melting point melts so as to preferentially melt and polymerize meso-lactide until meso-lactide is consumed, and thereafter second polymerization is performed at a temperature in a second temperature range which is higher than the first temperature range and in which racemic lactide having a high melting point melts so as to melt and polymerize residual racemic lactide, whereby semi-crystalline polylactide is produced.

4. The method according to claim 3 , wherein the first temperature range is 50° C. or higher and 130° C. or lower, and the second temperature range is 55° C. or higher and 250° C. or lower.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Aug 11, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: NATUREWORKS, LLC
Reel/Frame 072412/0844 →
SECURITY INTEREST Recorded Oct 20, 2021
From: NATUREWORKS LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057879/0338 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THIRD ASSIGNOR'S NAME PREVIOUSLY RECORDED AT REEL: 050638 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 4, 2019
From: HITACHI ZOSEN CORPORATION; TOHOKU ELECTRIC POWER CO., INC.; NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY
To: NATUREWORKS LLC
Reel/Frame 050917/0825 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2019
From: HITACHI ZOSEN CORPORATION; TOHOKU ELECTRIC POWER CO., INC.; NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSIT
To: NATUREWORKS LLC
Reel/Frame 050638/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2014
From: KISHIDA, HISANORI; HASEGAWA, TAKASHI; NOMURA, NOBUYOSHI; TAKAHASHI, MAKOTO; SCHROEDER, JOSEPH; NATAL, MANUEL
To: HITACHI ZOSEN CORPORATION; TOHOKU ELECTRIC POWER CO., INC.; NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY; NATUREWORKS LLC
Reel/Frame 034229/0880 →
Priority Claims (1)
JP 2011-198712 · Sep 12, 2011 · national
Continuity (1)
Related Publication 20150087799A1 · Mar 26, 2015