General Methodology for Chemical Synthesis of Polyesters

Seppälä, Jukka; Korhonen, Harri; Kylmä, Janne; Tuominen, Jukka

doi:10.1002/3527600035.bpol3b11

Cited by 5 publications

(13 citation statements)

References 149 publications

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“…The properties of the lactic acid based polymers can be easily modified through copolymerization, e.g. with glycolide or ε ‐caprolactone 1,2,7,8. Copolymerization is possible in both preparation methods, polycondensation and ROP.…”

Section: Preparation Of Prepolymersmentioning

confidence: 99%

“…In our laboratory, the chain extending methods for lactic acid based prepolymers have been developed 7,17,22,24–28. Two routes are shown in Figure 3.…”

Section: Chain Linking With Chain Extendersmentioning

confidence: 99%

“…Poly(lactic acid) has the advantage of being not only biodegradable but also renewable, since lactic acid is produced through microbial fermentation of biomass. Poly(glycolide) and poly( ε ‐caprolactone) are also commonly used aliphatic polyesters in biomedical applications 1–8…”

Section: Introductionmentioning

confidence: 99%

“…ROP of lactide can be carried out in melt or in solution by cationic, anionic or coordination‐insertion mechanisms, depending on the catalyst used. Stannous octoate (SnOct 2 ) is the most commonly used catalyst in ROP due to its high effectivity, low tendency for racemization, and low toxicity 7,8…”

Section: Introductionmentioning

confidence: 99%

“…An alternative route to achieve high‐molecular‐weight polyester is to extend oligomeric prepolymers with chain extenders 7,9,10. Chain extenders are usually difunctional low‐molecular‐weight chemicals that can increase the molecular weight of polymers in a fast reaction without producing any byproducts requiring a separate purification step.…”

Section: Introductionmentioning

confidence: 99%

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Degradable Polyesters through Chain Linking for Packaging and Biomedical Applications

Seppälä

Helminen

Korhonen

2004

Macromolecular Bioscience

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The major route to convert lactic acid to high-molecular-weight polymers is ring-opening polymerization of lactide. We have investigated alternative synthesis routes based on oligomerization and chain linking to produce high-molecular-weight thermoplastic degradable polymers cost-effectively. Chain linking also offers new possibilities to prepare degradable polyesters for biomedical applications by extending the range of polymer properties achievable. In this paper, we briefly review different chain linking techniques used in our laboratory. Typically, lactic acid prepolymers with molecular weights of around 3,000-15,000 g x mol(-1) have been prepared by direct polycondensation. Hydroxyl terminated oligomers have been chain linked by using diisocyanate coupling agents, preferably 1,4-butane diisocyanate, forming poly(ester-urethanes). Poly(ester-amides) have been prepared by using 2,2'-bis(2-oxazoline) as coupling agent for carboxylic acid telechelic oligomers. Chain linking by end functionalization has been used in the preparation of poly(ester-anhydrides). In addition, a variety of crosslinked degradable polymers and copolymers have been synthesized through different crosslinking routes, by using methacrylic, itaconic or maleic double bonds or triethoxysilane moieties. A biodegradation test and ecotoxicological evaluation of the degradation products were carried out in addition to hydrolysis tests. Lactic acid based chain linked polymers were biodegradable and the degradation products were harmless. In hydrolysis tests, enzymatic degradation was pronounced in the chain linked poly(epsilon-caprolactone).

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Section: Preparation Of Prepolymersmentioning

confidence: 99%

“…In our laboratory, the chain extending methods for lactic acid based prepolymers have been developed 7,17,22,24–28. Two routes are shown in Figure 3.…”

Section: Chain Linking With Chain Extendersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Degradable Polyesters through Chain Linking for Packaging and Biomedical Applications

Seppälä

Helminen

Korhonen

2004

Macromolecular Bioscience

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Polymeric Biomaterials for Scaffold-Based Bone Regenerative Engineering

Ogueri

Jafari

Ivirico

et al. 2018

Regen. Eng. Transl. Med.

114

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Reconstruction of large bone defects resulting from trauma, neoplasm, or infection is a challenging problem in reconstructive surgery. The need for bone grafting has been increasing steadily partly because of our enhanced capability to salvage limbs after major bone loss. Engineered bone graft substitutes can have advantages such as lack of antigenicity, high availability, and varying properties depending on the applications chosen for use. These favorable attributes have contributed to the rise of scaffold-based polymeric tissue regeneration. Critical components in the scaffold-based polymeric regenerative engineering approach often include 1. The existence of biodegradable polymeric porous structures with properties selected to promote tissue regeneration and while providing appropriate mechanical support during tissue regeneration. 2. Cellular populations that can influence and enhance regeneration. 3. The use of growth and morphogenetic factors which can influence cellular migration, differentiation and tissue regeneration in vivo. Biodegradable polymers constitute an attractive class of biomaterials for the development of scaffolds due to their flexibility in chemistry and their ability to produce biocompatible degradation products. This paper presents an overview of polymeric scaffold-based bone tissue regeneration and reviews approaches as well as the particular roles of biodegradable polymers currently in use.

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Novel Preparation Method for Poly(l-lactide)-Based Block Copolymers: Extended Chain Crystallites as a Solid-State Macro-Coinitiator

et al. 2007

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A novel synthetic method for poly(L-lactide) (PLLA)-based diblock copolymers was developed by the use of PLLA extended chain crystallites (or crystalline residues) as a solid-state macro-coinitiator. In this study, we showed one example, i.e., a synthesis of diblock copolymer composed of a crystalline PLLA chain and an amorphous poly(DL-lactide) chain by ring-opening polymerization of DL-lactide initiated with stannous octoate (i.e., tin(II) 2-ethylhexanoate) in the presence of PLLA extended chain crystallites. The PLLA extended chain crystallites were prepared by hydrolytic degradation of crystallized PLLA films at 97 degrees C for 70 h. The chains inside the extended chain crystallites are expected to be protected from transesterfication reaction. Gel permeation chromatography, polarimetry, 1H NMR spectroscopy, wide-angle X-ray scattering, and differential scanning calorimetry revealed that the diblock copolymer poly(L-lactide-block-DL-lactide) was successfully prepared without significant transesterification.

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General Methodology for Chemical Synthesis of Polyesters

Abstract: Introduction Condensation Polymerization Condensation of Hydroxy Acids Condensation of Aliphatic Diols with Dicarboxylic Acids or Anhydrides Ester Exchange Reactions Polycondensation of Diols and Acyl Chlorides Polycondensation of Aromatic Copolyesters E… Show more

Cited by 5 publications

References 149 publications

Degradable Polyesters through Chain Linking for Packaging and Biomedical Applications

Degradable Polyesters through Chain Linking for Packaging and Biomedical Applications

Polymeric Biomaterials for Scaffold-Based Bone Regenerative Engineering

Novel Preparation Method for Poly(l-lactide)-Based Block Copolymers: Extended Chain Crystallites as a Solid-State Macro-Coinitiator

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