Poly(3-hydroxyalkanoate) sulfonate: From nanoparticles toward water soluble polyesters

Modjinou, Tina; Lemechko, Pierre; Babinot, Julien; Versace, Davy‐Louis; Langlois, Valérie; Renard, Estelle

doi:10.1016/j.eurpolymj.2015.05.018

Cited by 18 publications

(20 citation statements)

References 30 publications

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“…The presence of the signals relating to the two CH 2 methylene (c, d), which are characteristic of sulfonate groups, appeared at 2.66 ppm and the total disappearance of the peaks relating to the terminal alkene group of side chains (7) and (8) indicated the success of the formation of PHOSO 3 − . We previously showed that no chain scission occurred during this thiol-ene reaction and the PHOSO 3 − is water soluble [ 26 , 27 ].…”

Section: Resultsmentioning

confidence: 99%

“…A copolymer based on unsaturated PHAs was functionalized with the polar SO 3 − sulfonate groups to promote, on the one hand, its solubility in water [ 26 , 27 ], and on the other hand, ionic interactions with cations. An efficient and reproducible method for the synthesis of copolymer of water soluble PHOSO 3 − was developed by thiol-ene reaction in the presence of sodium-3-mercapto-1-ethanesulfonate.…”

Section: Discussionmentioning

confidence: 99%

“…Amphiphilic PHAs-PEG copolymers that were synthesized by esterification [ 18 , 19 , 20 ] and by click chemistry [ 21 , 22 , 23 , 24 ] have shown the ability to self-associate in aqueous medium to form micelles, vesicular structures or polymersomes. Water soluble PHAs obtained by introducing PEG [ 18 ], ammonium groups [ 25 ], or sulfonate functions [ 26 , 27 ] retained their biocompatible and non-cytotoxic character and the presence of PEG and propyleneglycol (PPG) segments provided hydrophilicity, blood compatibility [ 28 ], and thermo-sensitivity respectively [ 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

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Antioxidant Network Based on Sulfonated Polyhydroxyalkanoate and Tannic Acid Derivative

2021

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A novel generation of gels based on medium chain length poly(3-hydroxyalkanoate)s, mcl-PHAs, were developed by using ionic interactions. First, water soluble mcl-PHAs containing sulfonate groups were obtained by thiol-ene reaction in the presence of sodium-3-mercapto-1-ethanesulfonate. Anionic PHAs were physically crosslinked by divalent inorganic cations Ca2+, Ba2+, Mg2+ or by ammonium derivatives of gallic acid GA-N(CH3)3+ or tannic acid TA-N(CH3)3+. The ammonium derivatives were designed through the chemical modification of gallic acid GA or tannic acid TA with glycidyl trimethyl ammonium chloride (GTMA). The results clearly demonstrated that the formation of the networks depends on the nature of the cations. A low viscoelastic network having an elastic around 40 Pa is formed in the presence of Ca2+. Although the gel formation is not possible in the presence of GA-N(CH3)3+, the mechanical properties increased in the presence of TA-N(CH3)3+ with an elastic modulus G’ around 4200 Pa. The PHOSO3−/TA-N(CH3)3+ gels having antioxidant activity, due to the presence of tannic acid, remained stable for at least 5 months. Thus, the stability of these novel networks based on PHA encourage their use in the development of active biomaterials.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antioxidant Network Based on Sulfonated Polyhydroxyalkanoate and Tannic Acid Derivative

2021

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“…The combination of tunable properties through chain length and branching control, co‐monomer composition, biodegradability, biocompatibility and thermoplastic properties has contributed to the large interest in PHA materials . It is even possible to produce PHAs with different functionalities including unsaturated groups, carboxyl, hydroxyl, epoxy and halogens, which enables numerous further reactions and modifications . It has also been suggested that organic waste via syngas fermentation could be a potential raw material for production of PHAs .…”

Section: Introductionmentioning

confidence: 99%

Polyhydroxyalkanoate-based drug delivery systems

2016

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Microbial polyhydroxyalkanoates (PHAs) have been a subject of significant research interest in the past few decades. The recent development of novel functionalized PHAs has opened up new possibilities to combine the good biocompatibility of PHA-based drug delivery systems to, for example, improve drug loading and release properties, targeting or imaging functionalities. This mini-review presents some recent scientific developments in the preparation of functionalized PHAs, PHA-drug and PHA-protein conjugates, multifunctional PHA nanoparticles and micelles as well as biosynthetic PHA particles for drug delivery. These developments in combination with the generally excellent biocompatibility of PHA materials are expected to further expand the interest in PHA materials for drug delivery and other therapeutic applications.

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“…With the existence of similar groups to polyester, WSP can bond well with polyester fibers and thus improve its adhesion to polyester. Since WSP has better sizing performance for polyester than other normal sizes, such as starch, polyvinyl alcohol and polyacrylic, 21,22 synthesis of WSP has been the focus of research in relevant fields. Making a survey of the synthetic methods at home and abroad, 22–27 it is found that the main reactants to create WSP include dicarboxylic acid, poly(ethylene glycol) and monomer components substituted with the sulfonate metal salt group, so it is reasonably to think that the glycolysis product of PET, that is, BHET, can be used to produce WSP.…”

mentioning

confidence: 99%

Synthesis and sizing performances of water-soluble polyester based on bis(2-hydroxyethyl) terephthalate derived from depolymerized waste poly(ethylene terephthalate) fabrics

Lü

et al. 2018

Textile Research Journal

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This work aimed at effective chemical recycling of waste poly(ethylene terephthalate) (PET) fabrics into water-soluble polyester (WSP). For this, PET fabric waste was depolymerized using excess ethylene glycol (EG) in the presence of zinc acetate as catalyst. The glycolysis product of PET, bis(2-hydroxyethyl) terephthalate (BHET) was then used to synthesize WSP by a three-step method, that is, transesterification, esterification and polycondensation. The structures of BHET and WSP were identified by Fourier transform infrared spectra. Sizing performances of WSP were studied, and it was found that the surface tension of WSP size (57 mN/m, 22℃, 0.5% of weight) was lower than common sizes, the viscosity of WSP size was 1–2 mPa·S (95℃, 6% of weight) and the viscosity stability was larger than 90% at this temperature. The mixture of WSP and starch showed stronger adhesion to polyester–cotton roving and polyester roving than onefold starch. K/S values of fibers before sizing and after desizing showed a slightly difference, which indicated that WSP would not influence the color of yarns when used as the sizing agent.

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Poly(3-hydroxyalkanoate) sulfonate: From nanoparticles toward water soluble polyesters

Cited by 18 publications

References 30 publications

Antioxidant Network Based on Sulfonated Polyhydroxyalkanoate and Tannic Acid Derivative

Antioxidant Network Based on Sulfonated Polyhydroxyalkanoate and Tannic Acid Derivative

Polyhydroxyalkanoate-based drug delivery systems

Synthesis and sizing performances of water-soluble polyester based on bis(2-hydroxyethyl) terephthalate derived from depolymerized waste poly(ethylene terephthalate) fabrics

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