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Types of Step-Growth Polymers: Polyesters01:20

Types of Step-Growth Polymers: Polyesters

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The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Thermoset elastomers derived from carvomenthide.

Jinyoung Yang1, Sangjun Lee, Woo Jin Choi

  • 1Center for Biobased Chemistry, ‡Chemical Materials Solutions Center, Korea Research Institute of Chemical Technology (KRICT) , 141 Gajeong-ro, Yuseong-gu, Daejeon 305-600, Korea.

Biomacromolecules
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Summary
This summary is machine-generated.

Researchers developed renewable thermoset elastomers from plant-based carvomenthide. These novel materials exhibit excellent thermal and mechanical properties, showing promise for soft tissue engineering applications.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biomaterials Engineering

Background:

  • Development of sustainable and biocompatible elastomers is crucial for advanced applications.
  • Plant-derived monomers offer a renewable alternative to petroleum-based feedstocks.
  • Thermoset elastomers require specific functionalization for tailored properties.

Purpose of the Study:

  • To synthesize and characterize novel renewable thermoset elastomers from carvomenthide.
  • To investigate the thermal, mechanical, and biocompatibility properties of the developed elastomers.
  • To evaluate the potential of these elastomers for soft tissue engineering.

Main Methods:

  • Ring-opening transesterification polymerization of carvomenthide to poly(carvomenthide) (PCM).
  • Esterification to create carboxy-telechelic PCM (HOOC-PCM-COOH).
  • Thermal curing of prepolymers with trifunctional aziridine.
  • Characterization using DSC, TGA, DMA, tensile testing, and cell adherence assays.

Main Results:

  • Successfully synthesized functionalized polyester prepolymers (HOOC-PCM-COOH) with high viscosity and thermal resistance.
  • Achieved cross-linked PCM elastomers with no crystallinity and low glass transition temperature.
  • Demonstrated favorable thermal stability, mechanical resilience, and good cell adherence.

Conclusions:

  • Renewable thermoset elastomers derived from carvomenthide offer a promising new class of biomaterials.
  • The synthesized elastomers possess properties suitable for soft tissue engineering.
  • Further development could lead to advanced medical devices and regenerative medicine solutions.