Martinez de Ilarduya Saez de Asteasu, Antxon
Total activity: 216
Research group
POL - Polymers
Department
Department of Chemical Engineering
School
Barcelona School of Industrial Engineering (ETSEIB)
E-mail
antxon.martinez.de.ilarduiaupc.edu
Contact details
UPC directory Open in new window
Orcid
0000-0001-8105-2168 Open in new window
ResearcherID
E-4034-2012 Open in new window
Scopus Author ID
6701794765 Open in new window

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1 to 50 of 216 results
  • Thermal behavior of long-chain alkanoylcholine soaps

     Tolentino Chivite, Ainhoa; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Font-Bardía, Mercè; León Cabanillas, Salvador; Muñoz Guerra, Sebastian
    RSC Advances
    Date of publication: 2014-06-02
    Journal article

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    Long-chain alkanoylcholines prepared from fatty acids (nACh) are fully sustainable cationic surfactants that are known for their biological and medicinal properties. In the present work the thermal behavior of the homologous series of alkanoylcholine iodides with n = 12, 14, 16 and 18, has been examined within the 25¿200 °C range of temperatures. Up to three thermotropic phases have been identified, and the thermal transitions implied in their interconversion have been characterized by DSC and simultaneous WAXS and SAXS analysis carried out in real-time. All three phases consist of a bilayered structure with alkanoyl chains confined in the space between the head group layers and interdigitated to a greater or lesser extent. Melting¿crystallization of either the polymethylene segments or the choline iodide groups is involved in such transitions. Additionally, a crystal phase consisting also of a bilayered structure but excluding side chain interdigitation was observed upon crystallization from solution and its structure was elucidated by single-crystal X-ray diffraction direct methods. The close correlation existing between thermal properties, phase structure and n has been brought into evidence.

  • Partially renewable copolyesters prepared from acetalized d-glucitol by solid-state modification of poly(butylene terephthalate)

     Gubbels, Erik; Lavilla, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Noordover, Bart A. J.; Koning, Cor E.; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2014-01-15
    Journal article

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    The backbone of poly(butylene terephthalate) (PBT) was modified with 2,4:3,5-di-O-methylene-D-glucitol (Glux) using solid-state modification (SSM). The obtained copolyesters proved to have a non-random overall chemical microstructure. The thermal properties of these semicrystalline, block-like, Glux-based materials were extraordinary, showing higher melting points, and glass transition temperatures compared with other sugar-based copolyesters prepared by SSM. These remarkable thermal properties were a direct result of the inherently rigid structure of Glux and the relatively slow randomization of the block-like chemical microstructure of the Glux-based copolyesters in the melt. SSM proved to be a versatile tool for preparing partially biobased copolyesters with superior thermal properties.

  • Comblike Ionic Complexes of Poly(gamma-glutamic acid) and Alkanoylcholines Derived from Fatty Acids

     Tolentino Chivite, Ainhoa; León Cabanillas, Salvador; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Macromolecules
    Date of publication: 2013-02-15
    Journal article

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    A series of ionic complexes with almost stoichio- metric composition have been “ synthesized ” from bacterial poly( γ - glutamic acid) and alkanoylcholines derived from fatty acids with 12, 14, 16, and 18 carbon atoms. The complexes were stable up to temperatures close to 200 ° C and were non-water-soluble but readily soluble in organic solvents. In the solid state they adopted the biphasic structure typical of comblike systems with the polypeptide chains arranged in sheets and periodically separated by a para ffi nic phase which was partially crystallized for C14, C16, and C18. The window width of the layered structure was estimated by SAXS to be within the 3.6 − 4.5 nm range, and WAXS showed that the alkyl tails were crystallized in a hexagonally packed lattice with a d 100 spacing of 0.41 nm. These complexes displayed reversible melting of the para ffi nic phase in the 40 − 65 ° C range at temperatures with values increasing with the length of the alkanoyl group. A slight expansion of the intersheet distance occurred at melting followed by contraction upon heating at higher temperatures but without signi fi cant alteration of the layered structure. The 13 C CP-MAS NMR analysis revealed the underlying polymethylene anti -to- gauche conformational conversion that takes place at the thermal transition. An energy-based simulation study of the crystallization process a ff orded a molecular picture of the complex and evidenced the favoring e ff ect of the choline structure on the packing of the alkyl side

  • D-Glucose-derived PET copolyesters with enhanced Tg

     Japu, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Polymer Chemistry
    Date of publication: 2013-06-21
    Journal article

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    2,4:3,5-Di-O-methylene-D-glucitol and dimethyl 2,4:3,5-di-O-methylene-D-glucarate have been copolymerized with ethylene glycol and dimethyl terephthalate by polycondensation in the bulk to produce PET copolyesters as well as their respective homopolyesters. The PET copolyesters with either the diol or the diacid counterpart partially replaced by Glux had molecular weights in the 20 000¿40 000 range and a random microstructure, and they were stable well above 300 C. The PET copolyesters containing more than 10¿15% of sugar-based units wereamorphous while those displaying crystallinity were observed to crystallize from the melt at much lower rates than PET. The glass transition temperature of PET dramatically increased with the incorporation of Glux, whichever unit, diol or diacid, was replaced, but the enhancing effect was stronger in the former case. the copolyesters exhibited a higher hydrolysis rate and an appreciable susceptibility towards biodegradation.

  • Solid-state modification of PBT with cyclic acetalized galactitol and D-mannitol: Influence of composition and chemical microstructure on thermal properties

     Lavilla Aguilar, Cristina; Gubbels, Erik; Martinez de Ilarduya Saez de Asteasu, Antxon; Noordover, Bart A. J.; Koning, Cor E.; Muñoz Guerra, Sebastian
    Macromolecules
    Date of publication: 2013-06-11
    Journal article

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    Two bicyclic carbohydrate-based diols, 2,3:4,5-di-O-methylene-galactitol or 2,4:3,5-di-O-methylene-D-mannitol, were introduced into the backbone of poly(butylene terephthalate) using the solid-state modification technique. The resulting copolyesters had a unique block-like chemical microstructure that endows them with superior thermal properties when compared with their random counterparts obtained by melt copolymerization. The materials prepared by SSM displayed higher melting points, crystallization temperatures, and crystallinity due to the presence of long PBT sequences in the copolyester. The glass-transition temperatures also increased upon incorporation of the bicyclic comonomers, this effect being more pronounced for Manx units. SSM was demonstrated to be a very suitable technique for the incorporation of rigid monomers into the amorphous phase of PBT, leading to bio-based non-random copolyesters with remarkable thermal properties

    Two bicyclic carbohydrate-based diols, 2,3:4,5- di- O -methylene-galactitol (Galx) or 2,4:3,5-di- O -methylene- D - mannitol (Manx), were introduced into the backbone of poly(butylene terephthalate) using the solid-state modi fi cation technique (SSM). The resulting copolyesters had a unique block-like chemical microstructure that endows them with superior thermal properties when compared with their random counterparts obtained by melt copolymerization. The materials prepared by SSM displayed higher melting points, crystal- lization temperatures, and crystallinity due to the presence of long PBT sequences in the copolyester. The glass-transition temperatures also increased upon incorporation of the bicyclic comonomers, this e ff ect being more pronounced for Manx units. The melting points of these block-like copolyesters decreased after melting due to the occurrence of randomization, but they remained higher than those of copolyesters prepared from the melt. SSM was demonstrated to be a very suitable technique for the incorporation of rigid monomers into the amorphous phase of PBT, leading to bio-based non-random copolyesters with remarkable thermal properties

  • The structure of poly(gamma-glutamic acid)/nanoclay hybrids compatibilized by alkylammonium surfactants

     Tolentino Chivite, Ainhoa; León, Salvador; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    European polymer journal
    Date of publication: 2013-09-01
    Journal article

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    Stoichiometric ionic complexes of bacterial poly(c-glutamic acid) with the cationic N-octadecyland N-docosyl-N,N,N-trimethylammonium surfactants were mixed with alkylammonium modified bentonite (Cloisite 30B) to generate hybrid compounds covering a wide range of clay/polymer compositions. The structure of these compounds was examined by XRD and cryoTEM, which indicated extensive penetration of the biopolymer into the nanoclay galleries with widening or even destruction of the layered arrangement of the complex and the clay. Simultaneous SAXS/WAXS analysis in real time showed that hybrids with moderate inorganic contents displayed melting/crystallization upon heating/cooling within the 40¿70 C interval with concomitant expansion/contraction of the intersheet spacing. 13C CP-MAS NMR revealed that an anti-to-gauche conformational interconversionof the alkyl chains was involved in the melting/crystallization process. The results providedby energy-based dynamical simulations proved the feasibility of the polyacid and thenanoclay to be homogenized in the hybrid due to the compatibilizing effect of the surfactant.

  • Sulfonated Poly(hexamethylene terephthalate) copolyesters

     Bautista Betancur, Mayka Irina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Conferencia Internacional de Polímeros para Investigadores Noveles
    Presentation's date: 2013-11-07
    Presentation of work at congresses

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  • Bio-Based PET Copolyesters from a D-Mannitol-derived Bicyclic Diol

     Lavilla, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Conferencia Internacional de Polímeros para Investigadores Noveles
    Presentation's date: 2013-11-04
    Presentation of work at congresses

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  • High Tg bio-based aliphatic polyesters from bicyclic D-mannitol

     Lavilla Aguilar, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Biomacromolecules
    Date of publication: 2013-03-11
    Journal article

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    The carbohydrate-based diol 2,4:3,5-di-O-methylene-d-mannitol (Manx) has been used to obtain aliphatic polyesters. Manx is a symmetric bicyclic compound consisting of two fused 1,3-dioxane rings and bearing two primary hydroxyl groups. In terms of stiffness, it is comparable to the widely known isosorbide, but it affords the additional advantages of being much more reactive in polycondensation and capable of producing stereoregular polymers with fairly high molecular weights. A fully bio-based homopolyester (PManxS) has been synthesized by polycondensation in the melt from dimethyl succinate and Manx. The high thermal stability of PManxS, its relatively high glass transition temperature (Tg = 68 °C) and elastic modulus, and its enhanced sensitivity to the action of lipases point to PManxS as a polyester of exceptional interest for those applications where biodegradability and molecular stiffness are priority requirements. In addition, random copolyesters (PBxManxyS) covering a broad range of compositions have been obtained using mixtures of Manx and 1,4-butanediol in the reaction with dimethyl succinate. All PBxManxyS were semicrystalline and displayed Tg values from -29 to +51 °C steadily increasing with the content in Manx units. The stress¿strain behavior of these copolyesters largely depended on their content in Manx and they were enzymatically degraded faster than PBS.

    The carbohydrate-based diol 2,4:3,5-di- O -methylene- D -mannitol (Manx) has been used to obtain aliphatic polyesters. Manx is a symmetric bicyclic compound consisting of two fused 1,3-dioxane rings and bearing two primary hydroxyl groups. In terms of sti ff ness, it is comparable to the widely known isosorbide, but it a ff ords the additional advantages of being much more reactive in polycondensation and capable of producing stereoregular polymers with fairly high molecular weights. A fully bio-based homopolyester (PManxS) has been synthesized by polycondensation in the melt from dimethyl succinate and Manx. The high thermal stability of PManxS, its relatively high glass transition temperature ( T g =68 ° C) and elastic modulus, and its enhanced sensitivity to the action of lipases point to PManxS as a polyester of exceptional interest for those applications where biodegradability and molecular sti ff ness are priority requirements. In addition, random copolyesters (PB x Manx y S) covering a broad range of compositions have been obtained using mixtures of Manx and 1,4-butanediol in the reaction with dimethyl succinate. All PB x Manx y S were semicrystalline and displayed T g values from − 29 to +51 ° C steadily increasing with the content in Manx units. The stress − strain behavior of these copolyesters largely depended on their content in Manx and they were enzymatically degraded faster than PBS.

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    Isocyanate toughened pCBT: reactive blending and tensile properties  Open access

     Abt, Tobias Martin; Martinez de Ilarduya Saez de Asteasu, Antxon; Bou Serra, Jorge; Sanchez Soto, Miguel Angel
    Express polymer letters
    Date of publication: 2013-02-01
    Journal article

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    Cyclic butylene terephthalate oligomers (CBT) were reacted in a ring-opening polymerization with three types of isocyanates: a bifunctional aromatic type, a bifunctional aliphatic type and a polymeric aromatic isocyanate. All reactions took place in a batch mixer. The use of 0.5 to 1 wt% isocyanate led to a dramatic increase in elongation at break of polymerized cyclic butylene terephthalate (pCBT), from 8 to above 100%. The stiffness and strength of the modified pCBT, however, were found to slightly decrease. Proton nuclear magnetic resonance (NMR) analysis shows that the formation of thermally stable amide groups is the dominant chain extension reaction mechanism. Gel content measurements suggest a linear structure for samples containing bifunctional isocyanates while pCBT modified with polyfunctional isocyanate exhibited some gel formation at higher isocyanate content. Melting and crystallization temperatures as well as degree of crystallinity were found to decrease with increasing isocyanate content. No phase separation was detected by scanning electron microscopy (SEM) analysis. Moreover, a high degree of polymerization is deduced due to the absence of CBT oligomer crystals.

    Electronic version of an article published as "Express polymer letters" vol. 7, nº. 2, February 2013, p. 172-185.

  • Sulfonated poly(hexamethylene terephthalate) copolyesters: enhanced thermal and mechanical properties

     Bautista Betancur, Mayka Irina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Journal of applied polymer science
    Date of publication: 2013-09-15
    Journal article

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    A series of poly(hexamethylene terephthalate-co-hexamethylene 5-sodium sulfoisophthalate) copolyesters containing from 5 to 50 mol % of sulfonated units as well as the two parent homopolymers are prepared by melt polycondensation. The polyesters are obtained with high molecular weights, which decrease with the increased content of sulfonated units in the copolymer. Polyesters with 5 and 10 mol % of sulfonated units are semicrystalline whereas for contents equal or above 20 mol % they are unable to crystallize from the melt. Thermogravimetric analysis show that the thermal stability decreases with the content in sulfonated units. Isothermal crystallizations of semicrystalline copolyesters show that the insertion of the sulfonated units causes a reduction of crystallizability, most probably due to the occurrence of ionic aggregations. It is observed a synergistic effect on the mechanical properties for copolymers with contents of around 5 mol % where the elongation at break increases drastically. Moreover, the hydrolytic degradationof the copolymer is enhanced with the content in sulfonated units.

    A series of poly(hexamethylene terephthalate- co -hexamethylene 5-sodium sulfoisophthalate) copolyesters containing from 5 to 50 mol % of sulfonated units as well as the two parent homopolymers are prepared by melt polycondensation. The polyesters are obtained with high molecular weights, which decrease with the increased content of sulfonated units in the copolymer. Polyesters with 5 and 10 mol % of sulfonated units are semicrystalline whereas for contents equal or above 20 mol % they are unable to crystal- lize from the melt. Thermogravimetric analysis show that the thermal stability decreases with the content in sulfonated units. Isother- mal crystallizations of semicrystalline copolyesters show that the insertion of the sulfonated units causes a reduction of crystallizabil- ity, most probably due to the occurrence of ionic aggregations. It is observed a synergistic effect on the mechanical properties for copolymers with contents of around 5 mol % where the elongation at break increases drastically. Moreover, the hydrolytic degrada- tion of the copolymer is enhanced with the content in sulfonated units

  • Bio-based poly(hexamethylene terephthalate) copolyesters containing cyclic acetalized tartrate units

     Japu, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Polymer
    Date of publication: 2013-03-08
    Journal article

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    A cyclic acetal of dimethyl l-tartrate (dimethyl 2,3-di-O-methylene l-threarate, Thx) was used as comonomer of dimethyl terephthalate (DMT) in the polycondensation with 1,6-hexanediol (HD) in the melt. Random copolyesters PHTxThxy with contents in tartrate units up to 50% were obtained with satisfactory molecular weights (Mw between 20,000 and 50,000) and dispersities slightly above 2, and without apparent discoloration. The copolyesters started to decompose above 300 °C. The Tg of the copolyesters oscillated between +9 and -9 °C with values steadily decreasing with increasing contents in Thx units. All the copolyesters as well as the homopolyester entirely made of tartrate units were semicrystalline with Tm falling from ~145 °C for PHT to ~70 °C for PHThx with intermediate values decreasing as the content in Thx increased. Copolyesters containing up to 30% of tartrate units were able to crystallize from the melt at crystallization rates that were delayed by the presence of tartrate units. The PHT70Thx30 copolyester displayed significant hydrodegradability when incubated in aqueous buffer and also certain biodegradability when subjected to the action of porcine pancreas lipases.

    A cyclic acetal of dimethyl l-tartrate (dimethyl 2,3-di-O-methylene l-threarate, Thx) was used as comonomer of dimethyl terephthalate (DMT) in the polycondensation with 1,6-hexanediol (HD) in the melt. Random copolyesters PHTxThxy with contents in tartrate units up to 50% were obtained with satisfactory molecular weights (Mw between 20,000 and 50,000) and dispersities slightly above 2, and without apparent discoloration. The copolyesters started to decompose above 300 °C. The Tg of the copolyesters oscillated between +9 and −9 °C with values steadily decreasing with increasing contents in Thx units. All the copolyesters as well as the homopolyester entirely made of tartrate units were semicrystalline with Tm falling from ∼145 °C for PHT to ∼70 °C for PHThx with intermediate values decreasing as the content in Thx increased. Copolyesters containing up to 30% of tartrate units were able to crystallize from the melt at crystallization rates that were delayed by the presence of tartrate units. The PHT70Thx30 copolyester displayed significant hydrodegradability when incubated in aqueous buffer and also certain biodegradability when subjected to the action of porcine pancreas lipases.

  • Comb-like ionic complexes of hyaluronic acid with alkyltrimethylammonium surfactants

     Tolentino Chivite, Ainhoa; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Carbohydrate polymers
    Date of publication: 2013-01-30
    Journal article

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    Stoichiometric complexes of hyaluronic acid with alkyltrimethylammonium surfactants bearing octadecyl, eicosyl and docosyl groups were prepared by ionic coupling in aqueous solution. The complexes were non soluble in water but soluble in organic solvents. In the solid state they self-assembled in a biphasic layered structure with the alkyl side chains forming a separate phase that melted in the 50–60 °C range. They were stable to heating up to above 200 °C.

  • PET copolyesters made from a D-mannitol-derived bicyclic diol

     Lavilla Aguilar, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Polymer Chemistry
    Date of publication: 2013-01-14
    Journal article

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  • Toughening of in situ polymerized cyclic butylene terephthalate by chain extension with a bifunctional epoxy resin

     Abt, Tobias Martin; Sanchez Soto, Miguel Angel; Martinez de Ilarduya Saez de Asteasu, Antxon
    European polymer journal
    Date of publication: 2012-01-01
    Journal article

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  • Carbohydrate-based polyurethanes: A comparative study of polymers made from isosorbide and 1,4-butanediol

     Marin Bernabe, Romina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Journal of applied polymer science
    Date of publication: 2012-01-15
    Journal article

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    A set of linear polyurethanes containing isosorbide units were synthesized by polymerization in solution from HDI and MDI diisocyanates and 1,4-butanediol(BD), isosorbide (Is) or diisosorbide diurethanes (Is2HDI and Is2MDI) as diols. The thermal transitions, thermal stability, and crystal structure of the polyurethane homopolymers and copolymers containing isosorbide were evaluated and compared with those displayed by their polyurethane analogues entirely made of BD. It was found that incorporation of Is units in the polyurethane chain produced significant changes in Tg, Tm, and Td but no significant differences were noticed between copolymers made from Is or Is2 monomers. Degradation assays revealed that the presence of Is units increased slightly the hydrolysis rate of polyurethanes.

  • Biodegradable aromatic copolyesters made from bicyclic acetalized galactaric acid

     Lavilla Aguilar, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Benito, Elena; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2012-08-15
    Journal article

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    Random poly(hexamethylene terephthalate-co-galactarate) s and poly(dodecamethylene terephthalate-co-galactarate) s copolyesters covering the whole range of compositions were obtained with weight-average molecular weights of 30,000–50,000 g mol 1 by melt polycondensation. They were thermally stable above 300 C, and displayed Tg in the þ20 to 20 C range with values steadily decreasing with the content in galactarate units. All the copolyesters were semicrystalline with Tm between 50 and 150 C and those made from dodecanediol were able to crystallize from the melt at a crystallization rate depending on composition. Copolyesters containing up to 50% of galactaric units retained the crystal structure of their respective polyterephthalate homopolyesters, whereas they adopted the structure of the respective polygalactarates when the content in Galx units reached 70%. Stress-strain essays revealed decay in the mechanical parameters as the aromatic units were replaced by Galx. Incubation in aqueous buffer revealed that hydrolysis of the polyesters were largely enhanced by copolymerization and evidenced the capacity of the Galx unit for making aromatic polyesters susceptible to biodegradation. A detailed NMR analysis complemented by SEM observations indicated that hydrolysis took place by preferred splitting of galactarate ester bonds with releasing of alkanediol and Galx-diacid.

  • Modification of microbial polymalic acid with hydrophobic amino acids for drug-releasing nanoparticles

     Lanz Landazuri, Alberto; García Álvarez, Montserrat; Portilla Arias, Jose Antonio; Martinez de Ilarduya Saez de Asteasu, Antxon; Holler, Eggehard; Ljubimova, Julia Y.; Muñoz Guerra, Sebastian
    Macromolecular chemistry and physics
    Date of publication: 2012-08-14
    Journal article

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    Microbial poly( β , L -malic acid) was modifi ed with either L -leucine ethyl ester (L) or L -phenylalanine methyl ester (F) to produce amphiphylic copolymers. The degradation of these copolymers in aqueous buffer took place under physiological conditions in a few weeks by hydrolysis of the side chain ester group followed by cleavage of the main chain. Spherical nanoparticles with diameters ranging between 70 and 230 nm were prepared from these copolymers by the dialysis-precipitation method. No alteration of the cell viability was observed after incubation of these nanoparticles in different cell lines. Anticancer drugs temozolomide and doxorubicin were encapsulated in the nanoparticles. Temozolomide was released within several hours whereas doxorubicin took several weeks to be completely liberated.

  • Bio-based poly(butylene terephthalate) copolyesters containing bicyclic diacetalized galactitol and galactaric acid: Influence of composition on properties

     Lavilla Aguilar, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Benito, Elena; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Polymer
    Date of publication: 2012-07-19
    Journal article

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    Copolyesters from 1,4-butanediol, dimethyl terephthalate and either 2,3:4,5-di-O-methylene-galactitol or dimethyl 2,3:4,5-di-O-methylene-galactarate with compositions of 10, 20, 30, 40 and 50% of either galactitol or galactarate units were prepared by melt-polycondensation. The copolyesters had Mw in the 32,000¿41,000 g mol-1 range and had a random microstructure. They displayed Tg from 20 to 70 °C with values steadily decreasing with the content in galactarate units but increasing with the content in galactitol units. All the copolyesters were semicrystalline with Tm between 115 and 210 °C and they adopted the crystal structure of PBT. Copolyesters containing up to 20% of galactitol units as well as all galactarate copolyesters were able to crystallize from the melt, at a crystallization rate that decreased with the content in carbohydrate-based units. Stress-strain essays revealed an increment in the tensile strength and elastic modulus with increasing contents in galactitol units whereas these parameters decreased when galactarate units were the replacing ones.

    Copolyesters from 1,4-butanediol, dimethyl terephthalate and either 2,3:4,5-di-O-methylene-galactitol or dimethyl 2,3:4,5-di-O-methylene-galactarate with compositions of 10, 20, 30, 40 and 50% of either galactitol or galactarate units were prepared by melt-polycondensation. The copolyesters had Mw in the 32,000–41,000 g mol−1 range and had a random microstructure. They displayed Tg from 20 to 70 °C with values steadily decreasing with the content in galactarate units but increasing with the content in galactitol units. All the copolyesters were semicrystalline with Tm between 115 and 210 °C and they adopted the crystal structure of PBT. Copolyesters containing up to 20% of galactitol units as well as all galactarate copolyesters were able to crystallize from the melt, at a crystallization rate that decreased with the content in carbohydrate-based units. Stress-strain essays revealed an increment in the tensile strength and elastic modulus with increasing contents in galactitol units whereas these parameters decreased when galactarate units were the replacing ones.

  • Bio-based aromatic copolyesters made from 1,6-hexanediol and bicyclic diacetalized D-glucitol

     Japu, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; García-Martín, M.G.; Benito, Elena; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Polymer Chemistry
    Date of publication: 2012-08-01
    Journal article

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    Bio-based aromatic polyesters from a novel bicyclic diol derived from D-mannitol  Open access

     Lavilla Aguilar, Cristina; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Macromolecules
    Date of publication: 2012-10-23
    Journal article

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    2,4:3,5-Di-O-methylene-D-mannitol, abbreviated as Manx, is a D-mannitol-derived compound with the secondary hydroxyl groups acetalized with formaldehyde. The bicyclic structure of Manx consists of two fused 1,3-dioxane rings, with two primary hydroxyl groups standing free for reaction. A homopolyester made of Manx and dimethyl terephthalate as well as a set of copolyesters of poly(butylene terephthalate) (PBT) in which 1,4-butanediol was replaced by Manx up to 50% were synthesized and characterized. The polyesters had Mw in the 30 000−52 000 g mol−1 range and a random microstructure and were thermally stable up to nearly 370 °C. They displayed outstanding high Tg with values from 55 to 137 °C which steadily increased with the content in Manx. Copolyesters containing up to 40% of Manx were semicrystalline and adopted the crystal structure of PBT. Their stress− strain parameters were sensitively affected by the presence of carbohydrate-based units with elongation at break decreasing but tensile strength and elastic moduli steadily increasing with the degree of replacement.

  • Poly(ethylene terephthalate) terpolyesters containing 1,4-cyclohexanedimethanol and isosorbide

     Quintana Vicente, Roberto; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    High performance polymers
    Date of publication: 2012-02-01
    Journal article

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    A series of poly(ethylene terephthalate) terpolyesters containing varying amounts of both 1,4-cyclohexylenedimethylene and isosorbide units were prepared by melt phase polycondensation. These terpolymers were obtained with high molecular weights and polydispersities around 2.0-2.5. The nuclear magnetic resonance data revealed that they were all random terpolymers and that small amounts of isosorbide were lost during the polycondensation reaction. Thermal data showed that terpolymers with 90 mol% of ethylene units were crystalline, whereas the two other series containing 80 and 70 mol% were unable to crystallize from the melt. For the three series studied, it was observed that the glass transition temperature increased steadily with the content of isosorbide units, and that they had similar thermal stability.

    A series of poly(ethylene terephthalate) terpolyesters containing varying amounts of both 1,4-cyclohexylenedimethylene and isosorbide units were prepared by melt phase polycondensation. These terpolymers were obtained with high molecular weights and polydispersities around 2.0–2.5. The nuclear magnetic resonance data revealed that they were all random terpolymers and that small amounts of isosorbide were lost during the polycondensation reaction. Thermal data showed that terpolymers with 90 mol% of ethylene units were crystalline, whereas the two other series containing 80 and 70 mol% were unable to crystallize from the melt. For the three series studied, it was observed that the glass transition temperature increased steadily with the content of isosorbide units, and that they had similar thermal stability.

  • Carbohydrate-based copolyesters made from bicyclic acetalized galactaric acid

     Lavilla Aguilar, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Benito, Elena; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2012-04-15
    Journal article

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    Mixtures of the dimethyl esters of adipic acid and 2,3:4,5-di-O-methylene-galactaric acid (Galx) were made to react in the melt with either 1,6-hexanediol or 1,12-dodecanediol to produce linear polycyclic copolyesters with aldarate unit contents varying from 10 up to 90 mole %. The copolyesters had weight–average molecular weights in the ∼35,000–45,000 g mol−1 range and a random microstructure, and were thermally stable up to nearly 300 °C. They displayed Tg in the -50 to -7 °C range with values largely increasing with the content in galactarate units. All the copolyesters were semicrystalline with Tm between 20 and 90 °C but only those made from 1,12-dodecanediol were able to crystallize from the melt at a crystallization rate that decreased as the contents in the two comonomers approached each other. Copolyesters containing minor amounts of galactarate units adopted the crystal structure characteristic of aliphatic polyesters but a new crystal polymorph was formed when the cyclic sugar units became the majority. Stress–strain parameters were sensitively affected by composition of the copolyesters with the mechanical behavior changing from flexible/ductile to stiff/brittle with the replacement of adipate units by the galactarate units.

  • Poly(gamma-glutamic acid) esters with reactive functional groups suitable for orthogonal conjugation strategies

     Pacini, Aurora; Caricato, Marco; Ferrari, Stefania; Capsoni, Doretta; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian; Pasini, Dario
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2012-11-15
    Journal article

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    We report on a series of novel poly(c-glutamic acid) (PGGA) esters, in which the chemical structure and composition, and the molecular weight are systematically changed. Modification of PGGA of microbial origin, used either as the sodium salt or in the free acid form, by means of alkylation with highly reactive bromides under SN2 conditions, affords copolymers with an essentially random microstructure. These reaction conditions are applied iteratively to achieve full esterification, obtaining allyl or propargyl ester functionalities within the polymer backbone, diluted with inert functional groups, such as benzyl, ethyl, or hexyl ester functionalities. The copolymers have been characterized regarding their chemical structure and thermal and bulk properties using nuclear magnetic resonance, thermogravimetry, differential scanning calorimetry, and X-ray diffraction techniques. We demonstrate that allyl and propargyl ester groups can be efficiently transformed using click chemistries, such as thiol-ene or copper(I)- catalyzed azide–alkyne cycloaddition reactions; such efficient conjugation strategies will be required to transformthe native bacterial biopolymer into a material with tailored properties for bulk scale or biomedical applications.

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    Carbohydrate-based polyesters made from bicyclic acetalized galactaric acid  Open access

     Lavilla Aguilar, Cristina; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Benito, Elena; García Martín, Maria de Gracia; Galbis Pérez, Juan Antonio; Muñoz Guerra, Sebastian
    Biomacromolecules
    Date of publication: 2011-07-11
    Journal article

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    The dimethyl ester of 2,3:4,5-di-O-methylene-galactaric acid (Galx) was made to react in the melt with 1,n-alkanediols HO(CH2)nOH containing even numbers of methylenes (n from 6 to 12) to produce linear polycyclic polyesters. Two sets of poly(alkylene 2,3:4,5-di-O-methylenegalactarate) polyesters (PE-nGalx) with weight-average molecular weights in the ∼5000 - 10000 and ∼35000 - 45000 ranges were obtained using TBT and DBTO catalysts, respectively. For comparative purposes a set of poly(alkylene adipate) polyesters (PE-nAd) was also synthesized with molecular weights in the higher range using a similar procedure. The thermal stability of PE-nGalx was greater than that of PE-nAd although it notably decayed as molecular weight decreased. The replacement of Ad by Galx in the polyesters caused increases in Tg of up to 70ºC, and almost doubled the tensile mechanical parameters. All PE-nGalx were semicrystalline but only those made from 1,12-dodecanediol were able to crystallize from the melt with a crystallization rate that diminished as the molecular weight increased. In general, the galactarate containing polyesters displayed higher solubility and wettability than polyadipates, they hydrolyzed faster and exhibited comparable sensitivity to the action of lipases.

  • Polyterephthalates made from ethylene glycol, 1,4-cyclohexanedimethanol, and isosorbide

     Quintana, Robert; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2011-05-15
    Journal article

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    Three series of terephthalate polyesters (copolyesters and terpolyesters) containing 70, 80, and 90 mol % of ethylene glycol respectively, 1,4-cyclohexanedimethanol (CHDM) and isosorbide in varying ratios, were synthesized by melt polycondensation. It was found that only ~75 mol % of the feeding isosorbide was incorporated in the resulting polyesters and that their content in diethylene glycol oscillated between 2 and 4 mol %. The polyesters had weight-average molecular weights in the 25,000–33,000 g mol~1 range and polydispersities between 2 and 2.5. The combined 1H and 13C NMR analysis revealed that the microstructure of all these polyesters was at random. They showed good thermal stability with decomposition temperatures above 400ºC. Their glass-transition temperatures were observed to increase with the content in cyclic diols, this effect being more pronounced when isosorbide was the replacing comonomer. Only the series containing 90 mol% of ethylene terephthalate units was able to crystallize upon cooling from the melt. Compared isothermal crystallizations revealed that isosorbide was more effective than CHDM in repressing the crystallizability of PET.

  • Polyesters based on cyclohexanedimethanol

     Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Date of publication: 2011-06-01
    Book chapter

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  • Comb-like ionic complexes of pectinic and alginic acids with alkyltrimethylammonium surfactants

     Tolentino Chivite, Ainhoa; Alla Bedahnane, Abdelilah; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Carbohydrate polymers
    Date of publication: 2011-08-15
    Journal article

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    Ionic coupling of both polygalacturonic and alginic acids with alkyltrimethyl ammonium surfactants containing 18, 20 and 22 carbon atoms in the alkyl side chain was conducted in water solution to prepare non-soluble comb-like complexes. These amphiphilic complexes are arranged in a biphasic layered structure with the paraffinic phase made of alkyl side chains alternating with the hydrophilic phase made of polyuronic chains. The complexes displayed the thermal behaviour typical of comb-like systems carrying long polymethylene groups, which melt at temperatures between 40 and 80 ◦C without significant disruption of the layered arrangement. Melting temperature, crystallinity and thermal stability were slightly higher for the polygalacturonic complexes and all they increased almost steadily with the length of the alkyl chain within each series. The melting-crystallization process was followed by combined WAXS/SAXS and 13C CP-MAS NMR, which revealed that the transition involves an expansion-contraction of the structure that may attain up to 20% of the original dimension. The transition takes place without large conformational changes and is not fully reversible.

  • Poly(methyl malate) nanoparticles: formation, degradation, and encapsulation of anticancer drugs

     Lanz, Alberto; García Álvarez, Montserrat; Portilla Arias, Jose Antonio; Martinez de Ilarduya Saez de Asteasu, Antxon; Patil, Rameshwar; Holler, Eggehard; Ljubimova, Julia Y.; Muñoz Guerra, Sebastian
    Macromolecular bioscience
    Date of publication: 2011-10-10
    Journal article

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    PMLA nanoparticles with diameters of 150–250nm are prepared, and their hydrolytic degradation is studied under physiological conditions. Degradation occurs by hydrolysis of the side chain methyl ester followed by cleavage of the main-chain ester group with methanol and L-malic acid as the final degradation products. No alteration of the cell viability is found after 1 h of incubation, but toxicity increases significantly after 3 d, probably due to the noxious effect of the released methanol. Anticancer drugs temozolomide and doxorubicin are encapsulated in the NPs with 20–40% efficiency, and their release is monitored using in vitro essays. Temozolomide is fully liberated within several hours, whereas doxorubicin is steadily released from the particles over a period of 1 month.

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    Poly(hexamethylene terephthalate-co-caprolactone) copolymers: influence of cycle size on ring-opening polymerization  Open access

     González Vidal, Nathalie; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    European polymer journal
    Date of publication: 2010-04-01
    Journal article

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    Poly(hexamethylene terephthalate) was cyclo-depolymerized in solution by heating to yield a fraction of cyclic oligomers of hexamethylene terephthalate (c(HT)2-5) with a content around to 95% in dimer to pentamer. Ring-opening polymerization in the melt of c(HT)2-5, either neat or in mixtures with ε-caprolactone (CL) covering a range of HT/CL ratios from 9/1 to 1/9 was carried out to produce polyesters with molecular weights above 30,000 in high yields. The copolyesters had a comonomer composition according to the feed and the microstructure evolved from random to blocky as the content in CL increases. The thermal and mechanical properties of the copolyesters were evaluated for a variety of compositions. Results obtained in this work were compared to those previously obtained by us in the ring-opening copolymerization of CL with a cyclic oligomeric fraction enriched in hexamer and heptamer (c(HT)6-7). Although the polyesters resulting from the use of these two fractions were similar, significant differences were found in polymerization rate evidencing a lower reactivity of c(HT)n with decreasing values of n.

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  • Ionic complexes of polyacids and cationic surfactants

     Tolentino Chivite, Ainhoa; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Macromolecular symposia
    Date of publication: 2010-10-01
    Journal article

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    Comb-like ionic complexes were prepared from polyuronic acids (pectinic and alginic acids) and alkyltrimethylammonium surfactants bearing linear alkyl chains with 18, 20 and 22 carbon atoms. In the condensed state, these complexes were able to self-assemble in ordered structures which were thermally stable up to ~200ºC. The complexes were analysed by DSC and WAXS/SAXS and compared to their analogous made from poly(γ-glutamic acid). They all adopt a biphasic layered structure in which the main chain and the alkyl side chain alternate with a nanometric periodicity. Alkyl side chains were partially crystallized in these complexes and they show reversible melting at temperatures within the 60-80ºC range depending on the length of the polymethylene segment.

  • Hydrolizable aromatic copolyesters of p-dioxanone

     Giammanco, Giuseppe; Martinez de Ilarduya Saez de Asteasu, Antxon; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Biomacromolecules
    Date of publication: 2010-09-13
    Journal article

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    Entropically driven ring-opening copolymerization of mixtures of a fraction of cyclic oligo(hexamethylene terephthalate)s composed of cycle sizes from 2 to 5 and p-dioxanone was used to prepare random copolyesters covering a range of aromatic (HT) to aliphatic (DO) units ratios from 9 to 1.3. The composition and microstructure of the copolyesters were accurately determined by 1H and 13C NMR, respectively. The copolyesters showed thermal degradation and glass transition temperatures in good agreement with their comonomeric composition and microstructure, and they crystallized for contents in DO less than 30%, adopting the same crystal structure as poly(hexamethylene terephthalate). The copolyesters appeared to be sensitive to hydrolytic degradation, which was observed to take place superficially with the generation of non-water-soluble degraded fragments and with the release of water-soluble dioxanoic acid to the aqueous medium.

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    Synthesis and properties of poly(hexamethylene terephthalate)/multiwall carbon nanotubes nanocomposites  Open access

     González Vidal, Nathalie; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian; Castell, Pere; Martínez, Maria Teresa
    Composites science and technology
    Date of publication: 2010-05-01
    Journal article

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    Poly(hexamethylene terephthalate) (PHT)/carbon nanotubes (CNT) nanocomposites containing 1% and 3% (w/w) of filler were prepared by two procedures: in situ ring-opening polymerization of hexamethylene terephthalate cyclic oligomers in the presence of CNT and melt blending of PHT/CNT mixtures. Arc discharge multiwalled carbon nanotubes, both pristine (MWCNT) and hydroxyl functionalized (MWCNT-OH), were used. The objective was to evaluate the effect of preparation procedure, nanotube sidewall functionalization and amount of nanotube loaded on properties of PHT. All nanocomposites showed an efficient distribution of the carbon nanotubes within the PHT matrix but interfacial adhesion and reinforcement effect was dependent on both functionalization and nanotubes loading. Significant differences in thermal stability and mechanical properties ascribable to functionalization and processing were observed among the prepared nanocomposites. All the prepared nanocomposites showed enhanced crystallizability due to CNT nucleating effects although changes in melting and glass transition temperatures were not significant.

    Postprint (author’s final draft)

  • Sequence analysis of polyether-based thermoplastic polyurethane elastomers by 13C NMR

     Martinez de Ilarduya Saez de Asteasu, Antxon; Carvalho, Erica; Alla Bedahnane, Abdelilah; Muñoz Guerra, Sebastian
    Macromolecules
    Date of publication: 2010-04-27
    Journal article

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    In this Note we would like to report on the analysis of the microstructure of segmented polyurethanes by 13CNMRmaking use of the signals arising from nonprotonated aromatic carbons which appear to be sensitive to dyads sequence distribution. The polyurethanes here studied were obtained from poly(tetramethylene glycol) (PTMG) as macrodiol soft segment, 1,4-butanediol (BD) chain extender, and 4,40'-methylenediphenyl diisocyanate (MDI) as hard segment.The results obtained in this work provide a relatively simple and reliable method to determine the microstructure of MDI-based thermoplastic polyurethanes by means of the NMR technique.

  • Poly(hexamethylene terephthalate)-layered silicate nanocomposites

     González Vidal, Nathalie; Muñoz Guerra, Sebastian; Martinez de Ilarduya Saez de Asteasu, Antxon; Benalia, Samira; Peeterbroeck, Sophie; Dubois, Philippe
    European polymer journal
    Date of publication: 2010-02-01
    Journal article

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  • Terephthalate copolyesters and nanocomposites produced by ring opening polymerization

     González Vidal, Nathalie
    Defense's date: 2010-06-04
    Department of Chemical Engineering, Universitat Politècnica de Catalunya
    Theses

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    Copolímeros poli(etilen-co-ciclohexanodimetilen tereftalato) obtenidos mediante copolimerización por apertura de anillo  Open access

     Muñoz Guerra, Sebastian; Martinez de Ilarduya Saez de Asteasu, Antxon; González Vidal, Nathalie
    Date: 2010-06-16
    Report

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  • POLÍMEROS Y NANOPOLÍMEROS DE FUENTES RENOVABLES PARA APLICACIONES BIOMÉDICAS

     Alla Bedahnane, Abdelilah; Bermúdez Hermida, Marta María; García Álvarez, Montserrat; Herranz Agustin, Concepcion; Majo Roca, Maria Antonia; Martinez de Ilarduya Saez de Asteasu, Antxon; Japu, Cristina; Tolentino Chivite, Ainhoa; Lavilla Aguilar, Cristina; Muñoz Guerra, Sebastian
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    Poly(ethylene terephthalate-co-isophthalate) copolyesters obtained from ethylene terephthalate and isophthalate oligomers  Open access

     Ubach, Joan; Martinez de Ilarduya Saez de Asteasu, Antxon; Quintana Vicente, Roberto; Alla Bedahnane, Abdelilah; Rudé, Elisabet; Muñoz Guerra, Sebastian
    Journal of applied polymer science
    Date of publication: 2010-02-05
    Journal article

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    A series of poly(ethylene terephthalate-co-isophthalate) copolyesters containing up to 50%-mole of isophthalic units were prepared by polycondensation from ethylene terephthalate and ethylene isophthalate fractions of linear oligomers containing from 5 to 6 repeating units in average. The polyesters were obtained in good yields and with high molecular weights. The microstructure of the copolyesters was studied as a function of reaction time by 13C-NMR showing that a random distribution of the comonomers was achieved since the earlier stages of polycondensation. The melting temperature and enthalpy of the copolyesters decreased with the content of isophthalic units so that copolyesters containing more than 25% of these units were amorphous. Isothermal crystallization studies made on crystalline copolyesters revealed that the crystallization rate of copolyesters decreased with the content in isophthalic units.

    Postprint (author’s final draft)

  • Butylene copolyesters based on aldaric and terephthalic acids. Synthesis and characterization

     Zamora, F; Hakkou, Khalid; Alla Bedahnane, Abdelilah; Rivas, M; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian; Galbis, J A
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2009-02
    Journal article

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  • Linear polyurethanes made from naturally occurring tartaric acid

     Marín, R; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2009-04
    Journal article

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  • Contribution to make poly(butylen terephthalate) (PBT) biodegradable

     Martinez de Ilarduya Saez de Asteasu, Antxon
    Les VIèmes Journées sur les Polymères Organiques et leurs Applications (JPOA VI)
    Presentation's date: 2009-05-15
    Presentation of work at congresses

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  • Nanoparticles Made of Microbial Poly(gamma-glutamate)s for Encapsulation and Delivery of Drugs and Proteins

     Portilla Arias, Jose Antonio; Camargo, B; García Álvarez, Montserrat; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Journal of biomaterials science. Polymer edition
    Date of publication: 2009-07
    Journal article

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  • POLÍMERS INDUSTRIALS AVANÇATS I BIOPOLÍMERS

     Alla Bedahnane, Abdelilah; Bermúdez Hermida, Marta María; García Álvarez, Montserrat; Majo Roca, Maria Antonia; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
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    Poly(ethylene-co-1,4-cyclohexylenedimethylene terephthalate) copolyesters obtained by ring opening polymerization  Open access

     González Vidal, Nathalie; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2009-11-15
    Journal article

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    Cyclic oligomer fractions of ethylene terephthalate c(ET)n and 1,4-cyclohexylenedimethylene terephthalate c(CT)n were obtained by yclodepolymerization of their respective polyesters, the former containing around 80 mol % of trimer and the latter with around 70 mol % of trimer to pentamer. Mixtures of these fractions at selected compositions were subjected to ring opening copolymerization to give a series of poly(ethylene-co-cyclohexylenedimethylene terephthalate) copolyesters with ET/CT comonomer ratios ranging from 90/10 to 10/90. The copolyesters were characterized by GPC and NMR, and their thermal properties were evaluated by DSC and TGA. They had essentially the same composition as the feed from which they were produced and had an average-weight molecular weights between 30,000 and 40,000 g/mol with polydispersities between 2 and 2.7. The distribution of the monomeric units in these copolyesters was essentially at random although it evolved to be a blocky microstructure as the contents in the two comonomers became more dissimilar. Their thermal behavior was the expected one for these types of copolyesters with crystallinity and heating stability decreasing with the content in CT units.

    Postprint (author’s final draft)

  • Spectroscopic Evidence for Stereocomplex Formation by Enantiomeric Polyamides Derived from Tartaric Acid

     Marín, R; Martinez de Ilarduya Saez de Asteasu, Antxon; Romero, P; Sarasua, J R; Meaurio, E; Zuza, E; Muñoz Guerra, Sebastian
    Macromolecules
    Date of publication: 2008-05
    Journal article

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  • Synthesis, Degradability, and Drug Releasing Properties of Methyl Esters of Fungal Poly(beta,L-malic acid)

     Portilla Arias, Jose Antonio; García Álvarez, Montserrat; Martinez de Ilarduya Saez de Asteasu, Antxon; Holler, E; Galbis, J A; Muñoz Guerra, Sebastian
    Macromolecular bioscience
    Date of publication: 2008-06
    Journal article

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  • Polyesters analogous to PET and PBT based on O-benzyl ethers of xylitol and L-arabinitol

     Zamora, F; Hakkou, Khalid; Alla Bedahnane, Abdelilah; Marín-Bernabé, R; Paz, M V De; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian; Galbis, J A
    Journal of polymer science. Part A, polymer chemistry
    Date of publication: 2008-08
    Journal article

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  • Biodegradable nanoparticles of partially methylated fungal poly(beta-L-malic acid) as a novel protein delivery carrier

     Portilla Arias, Jose Antonio; García Álvarez, Montserrat; Galbis, J A; Muñoz Guerra, Sebastian; Martinez de Ilarduya Saez de Asteasu, Antxon
    Macromolecular bioscience
    Date of publication: 2008-06
    Journal article

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  • Synthesis and Rheological Features and Flow-Induced Crystallization of Branched Poly[ethylene-co-(1,4-cyclohexanedimethylene terephthalate)] Copolyesters

     Quintana, Robert; Martinez de Ilarduya Saez de Asteasu, Antxon; Muñoz Guerra, Sebastian; Fernández, M; Santamaría, A
    Macromolecular materials and engineering
    Date of publication: 2008-10
    Journal article

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