The use of different diols in the synthesis of low-molecular-weight lactic-acid-based telechelic prepolymers

Hiltunen, Kari; Seppälä, Jukka

doi:10.1002/(sici)1097-4628(19980207)67:6<1017::aid-app8>3.0.co;2-l

Cited by 12 publications

(7 citation statements)

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“…Hiltunen et al . [27, 28]used different diols in the synthesis of low molecular weight hydroxyl‐terminated telechelic prepolymers, such as aliphatic diol, several aromatic diols with different structures and an aromatic diol that contains a heteroatom. The results showed that aliphatic diol produced hydroxyl‐terminated prepolymer with quite good molecular weights and the prepolymer were amorphous and low glass transition temperature.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and chain extension of hydroxyl‐terminated poly(lactic acid) oligomers and application in the blends

Junshao¹,

Chen²,

Huihua³

et al. 2013

Polymer Composites

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Hydroxyl‐terminated poly(lactic acid) prepolymer (LA prepolymer) were prepared via L‐lactic acid as monomer, 1,4‐butanediol as blocking agent and Sn(II) octoate as catalyst by direct melt polymerization. Then the LA prepolymer was blended with starch followed by in situ chain extending reaction using different content of TDI as chain extender, producing the high molecular weight of poly(ester urethane) in the blends. The LA prepolymer/starch‐TDI blends were characterized by GPC, 1H‐NMR, SEM, DSC, tensile strength testing, and water resistance. The SEM results of cross‐section show that, compared with the simple PLA/starch blends, almost the starch granules were completely covered by ploy(ester urethane) in the LA prepolymer/starch‐TDI blends system. In comparison to the simple PLA/starch blends, the mechanical properties of LA prepolymer/starch‐TDI blends were increased, such as tensile strength increasing from 18.6 ± 3.8 to 44.2 ± 6.2 Mpa, tensile modulus increasing from 510 ± 62 to 1,850 ± 125 Mpa and elongation at break increasing from 1.8 ± 0.4 to 4.0 ± 0.5 %, respectively. This is attributed to high weight of poly (ester urethane) was formed via in situ reaction of the end of hydroxyl (LA prepolymer) and isocyanate groups and the starch granules were easily covered by ploy(ether urethane) via in situ polymerization in the blends. Moreover, covalent linkage was formed between the two phases interfaces. As a result, the interfacial adhesion was enhance and improved the mechanical property. In addition, the water resistance of LA prepolymer/starch‐TDI blends was much better that of the simple PLA/starch blends. POLYM. COMPOS., 2013 © 2013 Society of Plastics Engineers

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Section: Resultsmentioning

confidence: 99%

Synthesis and chain extension of hydroxyl‐terminated poly(lactic acid) oligomers and application in the blends

Junshao¹,

Chen²,

Huihua³

et al. 2013

Polymer Composites

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“…Kylmä and Seppälä [97] applied the two-step process by copolymerizing εcaprolactone with lactic acid, which was followed by chain linking, thus introducing thermoplastic poly(ester-urethane) (PEU) elastomer. The incorporation of various comonomers can impede rotation of the molecule and stiffen the polymer chain, which cause an increase in T g [98].…”

Section: Reactions: a Reviewmentioning

confidence: 99%

Novel green biodegradable polylactide based polyurethane triblock copolymers reinforced with cellulose nanowhiskers

Hady¹

2021

Preprint

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Novel green classes of biodegradable polylactide-based triblock polyurethane (TBPU) polymers were synthesized. Owing to their tailored mechanical properties, improved degradation rates, and the enhance cell attachment potential compared with polylactide-homopolymer, they tested for biomedical applications. Triblock copolymers (TB) of different lactide and polyethylene glycol composition were first fabricated by ring-opening polymerization using tin octoate as catalyst. Afterwich polycaprolactone diole (PCL-diole) is reacted with TB copolymers using 1,4-butane diisocyanate (BDI) as nontoxic chain extender to form the final TBPUs. Final composition, molecular weight, thermal properties, hydrophilicity and biodegradation of the obtained TB and TBPU were studied and characterized using 1H-NMR, GPC, FTIR, DSC, SEM and contact angle measurements. Results obtained from the high molecular weight members of TBPUs showed improved hydrophilicity and degradation rates along with tailored mechanical properties. Nanocomposites obtained by reinforcing TBPU3 with 7% (w/w) BCNW showed ~16% increase in tensile strength and 330% in % elongation compared with PL-homopolymer. Those polymers and their nanocomposites demonstrated promising potential to be used as bone cement, and in regenerative medicin.

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“…The excess of solvent was evaporated under vacuum, and the viscous liquid oligomer was placed in a vacuum oven, at 40°C, for four days. [17,18] PLA-OH 1:…”

Section: Synthesis Of L-la Telechelic Oligomersmentioning

confidence: 99%

“…It is expected that the diols react with a molecule of L-LA or a small L-LA oligomeric chain, yielding oligomeric chains with hydroxyl terminal groups. [17,18] As the polymerization proceeds, the carboxylic groups of L-LA monomer or L-LA oligomeric chain react with the hydroxyl groups of the telechelic chain. As a result, at the end of the polymerization, the final product should have only one type of terminal group.…”

Section: Synthesis Of L-la Telechelic Oligomers and Their Chemical Stmentioning

confidence: 99%

Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties

Fonseca

Coelho

Valente

et al. 2013

Journal of Biomaterials Science, Polymer Edition

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Novel biodegradable and low cytotoxic poly(ester amide)s (PEAs) based on α-amino acids and (L)-lactic acid (L-LA) oligomers were successfully synthesized by interfacial polymerization. The chemical structure of the new polymers was confirmed by spectroscopic analyses. Further characterization suggests that the α-amino acid plays a critical role on the final properties of the PEA. L-phenylalanine provides PEAs with higher glass transition temperature, whereas glycine enhances the crystallinity. The hydrolytic degradation in PBS (pH = 7.4) at 37 °C also depends on the α-amino acid, being faster for glycine-based PEAs. The cytotoxic profiles using fibroblast human cells indicate that the PEAs did not elicit an acute cytotoxic effect. The strategy presented in this work opens the possibility of synthesizing biodegradable PEAs with low citotoxicity by an easy and fast method. It is worth to mention also that the properties of these materials can be fine-tuned only by changing the α-amino acid.

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The use of different diols in the synthesis of low-molecular-weight lactic-acid-based telechelic prepolymers

Cited by 12 publications

References 1 publication

Synthesis and chain extension of hydroxyl‐terminated poly(lactic acid) oligomers and application in the blends

Synthesis and chain extension of hydroxyl‐terminated poly(lactic acid) oligomers and application in the blends

Novel green biodegradable polylactide based polyurethane triblock copolymers reinforced with cellulose nanowhiskers

Poly(ester amide)s based on (L)-lactic acid oligomers and α-amino acids: influence of the α-amino acid side chain in the poly(ester amide)s properties

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