Structural Characterization and Degradability of Poly(<scp>L</scp>‐lactic acid)s Incorporating Phenyl‐Substituted <i>α</i>‐Hydroxy Acids as Comonomers

Moon, Sung-Il; Urayama, Hiroshi; Kimura, Yoshiharu

doi:10.1002/mabi.200390038

Cited by 32 publications

(23 citation statements)

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“…Particularly, copolymers of Llactic acid and phenyl-substituted -hydroxy acids such as Land D-mandelic acids (L-, D-MA) and phenyllactic acid (Phe-LA) were prepared. 17 It was found that the glass transition temperature of the copolymers comprising L-mandelic acid became significantly higher (from 58 to 69 C) with increasing content of L-mandelic acid (from 0 to 50 mol %) although the M w decreased with it (from 87,000 to 4,000 Da). Polyglactin was also synthesized by direct co-polycondensation of glycolic acid and L-lactic acid.…”

Section: Polycondensation Approach To High-molecular-weight Pllamentioning

confidence: 99%

Molecular, Structural, and Material Design of Bio-Based Polymers

Kimura

2009

Polym. J.

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Bio-based polymers are made from bio-originated feedstocks. Among those developed thus far, polylactides (PLA) stand at the forefront of practical use and are now manufactured on a commercial scale. However, the application of PLAs has been rather limited because of their higher cost, inferior thermal and mechanical properties, and worse processability as compared to the conventional oil-based polymers. Much effort has therefore been made to address it. Our major approach is to develop a direct polycondensation method to synthesize PLA and to use stereoblock-type PLA (sb-PLA) consisting of enantiomeric poly(L-lactide) (PLLA) and poly(D-lactide) (PDLA) because it can easily form stereocomplex (sc) showing a high melting temperature. Other specialty bio-based polymers are also synthesized for application to high-value fields. Particularly, with amphiphilic copolymers consisting of PLA and poly(oxyethylene) (PEG), new morphology change and sol-gel process have been disclosed. New bio-based polymers consisting of bio-derived monomeric units have also been synthesized to demonstrate their special functions. In addition, molecular and material design has been done with other biobased polymers such as poly(butylene succinate) (PBS) and poly(3-hydroxyalkanoate)s (PHA).

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Section: Polycondensation Approach To High-molecular-weight Pllamentioning

confidence: 99%

Molecular, Structural, and Material Design of Bio-Based Polymers

Kimura

2009

Polym. J.

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“…On the other hand, the existence of water molecules leads to depolymerization of the PLA. As reported in Moon, et al [10], the best PLA product was produced using SnCl 2 catalyst. The catalyst mechanism of SnCl 2 /TSA during polymerization showed that SnCl 2 has high solubility in water and is first activated by water molecules after which the polymerization rate increases.…”

Section: Molecular Weight Of Pla Synthesized With Different Catalystsmentioning

confidence: 62%

“…In comparison with the well-established method for the catalytic ring-opening polymerization of L-lactide [4][5][6][7], the direct polycondensation of L-lactic acid has received much less attention. Studies of direct polycondensation of L-lactic acid with various catalysts [8,9], melt/solid polycondensation [10], and direct condensation polymerization of L-lactic acid in bulk state [11] have been conducted in order to investigate the production of PLA with a high molecular weight. In recent years, a breakthrough was reported by Kimura, et al [12] and Gao, et al [13], who produced high molecular weight PLA by direct melt polycondensation using binary catalysts system stannous(II) chloride dihydrate/para-toluene sulphonic acid monohydrate (SnCl 2 /TSA) in a relatively short reaction time.…”

Section: Introductionmentioning

confidence: 99%

Molecular Weight and Structural Properties of Biodegradable PLA Synthesized with Different Catalysts by Direct Melt Polycondensation

Lee

Insyani

Prasetyo

et al. 2015

J. Eng. Technol. Sci.

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Abstract. Production of biodegradable polylactic acid (PLA) from biomassbased lactic acid is widely studied for substituting petro-based plastics or polymers. This study investigated PLA production from commercial lactic acid in a batch reactor by applying a direct melt polycondensation method with two kinds of catalyst, γ-aluminium(III) oxide (γ-Al 2 O 3 ) or zinc oxide (ZnO), in reduced pressure. The molecular weight of the synthesized PLA was determined by capillary viscometry and its structural properties were analyzed by functional group analysis using FT-IR. The yields of polymer production with respect to the theoretical conversion were 47% for γ-Al 2 O 3 and 35% for ZnO. However, the PLA from ZnO had a higher molecular weight (150,600 g/mol) than that from γ-Al 2 O 3 (81,400 g/mol). The IR spectra of the synthesized PLA from both catalysts using polycondensation show the same behavior of absorption peaks at wave numbers from 4,500 cm -1 to 500 cm -1 , whereas the PLA produced by two other polymerization methods -polycondensation and ring opening polymerizationshowed a significant difference in % transmittance intensity pattern as well as peak area absorption at a wave number of 3,500 cm -1 as -OH vibration peak and at 1,750 cm -1 as -C=O carbonyl vibrational peak.

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“…In particular, the T g of poly(mandelic acid), composed of the naturally occurring substance mandelic acid, is similar to that of polystyrene . It was also demonstrated that poly(mandelic acid‐ co ‐lactic acid) can be synthesized by polycondensation of mandelic acid and lactic acid . The T g value of the obtained copolymers was reported to increase with increasing mandelic acid content as shown in Fig.…”

Section: Current High‐performance Polylactidesmentioning

confidence: 64%

Macromolecular design of specialty polylactides by means of controlled copolymerization and stereocomplexation

Masutani

Kimura

2016

Polymer International

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Among the bio-based polymers thus developed, poly-L-lactide (PLLA) has been the most widely used in many fields because of its excellent cost-property balance.However, the properties and functionalities of PLLA cannot easily be controlled as the conventional petroleum-based polymers, retarding the progress of its manufacturing in large scale. One approach to obtain high-performance and specialty polylactides is to use stereocomplex-type polylactides (sc-PLA) that can be obtained by mixing PLLA and its enantiomer poly-D-lactide (PDLA). The other approach is to use copolymers consisting of polylactides (PLA) and other types of macromolecular chains. Here we demonstrate how such high-performance and specialty PLA polymers can be designed and synthesized. These macromolecular designs and synthetic methodologies are This article is protected by copyright. All rights reserved.This article has been accepted for publication and undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record. Please cite this article as doi: 10.1002/pi.5172 Accepted Articlehighly effective for controlling the structure and properties of the PLA polymers for use as biomedical and high-end industrial materials.Key words: polylactides, stereoblock, polymer blend, copolymerization, surface immobilization 1) IntroductionPolymeric materials prepared from renewable natural resources are now being accepted as ''bio-based polymers''. These polymers are characterized by the new processing method called ''white biotechnology'' where bio-engineering using fermentation and plant biotechnology is focused as the principal technology. It is evident that the bio-synthesis of a number of key monomers (so-called platform chemicals) such as succinic and 2,5-furandicarboxylic acids has been progressing quite rapidly. Even terephthalic and adipic acids may possibly be replaced by the ones synthesized from these bio-based monomers and chemicals. This article is protected by copyright. All rights reserved. Accepted ArticleOther biomass-originated polyamides such as Nylon 11, polyesters such as poly(ethylene furanoate) (PEF), and isosorbide-based polycarbonate (Is-PC) will also be manufactured in large scale very soon. Some of these biobased polymers were once developed as biodegradable polymers that can be broken down into environmentally friendly substances by composting. However, their application was limited to temporal use at low cost, and their market has not become large enough. For replacing structural materials made of oil-based polymers, high-performance bio-based polymers ought to be developed because toughness and durability are needed for these applications.Among the bio-based polymers mentioned above, PLLA has taken a special position because of its balanced properties and cost performance. It can readily be prepared by ring-opening polymerization (ROP) of L-lactide monomer synthesized from L-lactic acid, a fe...

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Structural Characterization and Degradability of Poly(L‐lactic acid)s Incorporating Phenyl‐Substituted α‐Hydroxy Acids as Comonomers

Cited by 32 publications

References 31 publications

Molecular, Structural, and Material Design of Bio-Based Polymers

Molecular, Structural, and Material Design of Bio-Based Polymers

Molecular Weight and Structural Properties of Biodegradable PLA Synthesized with Different Catalysts by Direct Melt Polycondensation

Macromolecular design of specialty polylactides by means of controlled copolymerization and stereocomplexation

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