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Ju

y 15-17, 2015

Polytechnic Institute of

Bragan~a 1

PCT-TMAD Brigantia EcoPark

Bragan~a

· Portugal

WORKSHOP

PROCEEDINGS

Eds.- M. F. Barreiro, 0. Ferreira, A.l. Pereira

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Title

6th Workshop- Green Chemistry and Nanotechnologies in Polymer Chemistry

Edited by

M.F. Barreiro, 0. Ferreira, A. I. Pereira

Graphic Design

Soraia Maduro- CIPweb IPB

First edition

07/2015

ISBN

978-972-745-188-3

Edition

(3)

0

c_th

Green Chemistry and Nanotechnologies

in Polymer Chemistry

Committees

Scientific Committee

Aleksander Prociak, Cracow University of Technology, Poland

Alessandro Gandini, IQSC University of Sao Paulo, Brazil

Alfonso Jimenez, University of Alicante, Spain

Allrio Rodrigues, University of Porta, Portugal

Ana Vera Machado, University of Minho, Portugal

Andrea Lazzeri, University of Pisa, Italy

Arantxa Eceiza, University of the Basque Country, Spain

Armando Silvestre, University of Aveiro, Portugal

Bela Pukansky, Budapest University, Hungary

Fernao Magalhaes, University of Porta, Portugal

Filomena Barreiro, Polytechnic Institute of

Bragan~a.

Portugal

Helena Gil, University of Coimbra, Portugal

Janusz Datta, Gdansk University of Technology, Poland

Joanna Ryszkowska, Warsaw University of Technology, Poland

Joao Mano, University of Minho, Portugal

Jose Vega Baudrit, Centra Nacional de Alta Tecnologra (CeNAT), Costa Rica

Juan Francisco Rodriguez, University of Castilla La Mancha, Spain

Luisa Carvalho, Polytechnic Institute of Viseu, Portugal

Mario Rui P.F.N. da Costa, University of Porta, Portugal

Mirta Aranguren, CONICET University of Mar de Plata, Argentina

Naceur Belgacem, Grenoble INP-Pagora, France

Tom as Vlcek, TOSEDA S.R.O.Research

&

Development Center, Czech Republic

Tomasz Sterzynski, Poznan University of Technology, Poland

Ugis Cabulis, Institute of Wood Chemistry, Latvia

Organizing Committee

Ana lsabel Pereira, Polytechnic Institute of

Bragan~a.

Portugal

Filomena Barreiro, Polytechnic Institute of

Bragan~a.

Portugal

Helder Games, Polytechnic Institute of Braganca, Portugal

lsabel Ferreira, Polytechnic Institute of

Bragan~a.

Portugal

Joana Amaral, Polytechnic Institute of Braganca. Portugal

Jose Santos, Polytechnic Institute of Braganca, Portugal

Olga Ferreira, Polytechnic Institute of

Bragan~a.

Portugal

Paulo Piloto, Brigantia Ecopark, Portugal

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6th Workshop on Green Chemistry and Nanotechnologies in Polymer Chemistry

v

Table of Contents

INVITED LECTURES ...1

IL I. THE CHEMIC AL MODIFICATION OF N ATUR AL POL YMERS BY THE DIELS-ALDER REACTION ... 2

A. Gandini

IL II. NANOSTRUCTURED MULTILAYERS OBTAINED FROM NATURAL-BASED POLYMERS:

BIOMEDICAL APPLIC ATIONS ... 2 J.F. Mano

IL III. GREEN SYNTHESIS OF POL YMERS USING SUPERCRITICAL CO2 ... 3

J.F. Rodriguez, C. Gutierrez

IL IV. APPLIC ATIONS OF NATURAL POL YMERS IN INDUSTRY AND MEDICINE ... 3

M.H. Gil, P. Alves, P. Coimbra, P. Ferreira

ORAL PRES ENTATIONS ...4

O01. INFLUENCE ON ISOCYANATE INDEX ON SELECTED PROPERTIES OF FLEXIBLE

POLYURETHANE FOAMS MODIFIED WITH VARIOUS BIO-COMPONENTS ... 5 A. Prociak, E. Malewska, S. Bąk

O02. OXYPROPYLATION OF GREY ALDER BARK AND ITS FRACTIONS TO OBTAIN POLYOLS USABLE

FOR PRODUCTION OF RIGID POLYURETH ANE FOAMS ... 7 L. Vevere, A. Arshanitsa, G. Telysheva

O03. SYNTHESIS, STRUCTURE AND PROPERTIES OF NOVEL POLYHYDROXYURETHANES OBTAINED

BY NON-ISOCYAN ATE ROUTE ... 9 M. Włoch, J. Datta

O04. RIGID POLYURETHANE FOAMS AS THERMAL INSULATION MATERIAL BASED ON RECYCLED

PET AND RAPESEED OIL ... 10 A. Paberza, A. Fridrihsone-Girone, A. Abolins, U. Cabulis

O05. BALANCE BETWEEN RENEWABLE AND RECYCLABLE FEEDSTOCK FOR RIGID POLYURETHANE

FOAMS ... 12 U. Cabulis, M. Kirpluks, A. Paberza, A. Fridrihsone-Girone, I. Vitkauskiene

O06. WATERBORNE POL YURETHANE-CELLULOSE NANOCRYSTALS N ANOCOMPOSITES ... 14

A. Santamaría-Echart, A. Saralegi, L. Martin, M.A. Corcuera, A. Eceiza

O07. BIO-BASED POL YURETHANE EL ASTOMERS - SYNTHESIS AND CHARACTERIZATION ... 16

J. Datta

O08. POLYURETHANE FOAMS OBTAINED FROM RECOVERED POLYOL THROUGH CHEMICAL

RECYCLING ... 17 P. Kopczyńska, J. Datta

O09. INFLUENCE OF PROCESS VARIABLES IN ESTOLIDE SYNTHESIS AND THEIR ESTER

DERIVATIVES FROM OLEIC ACID... 18 J.C. de Haro, M.P. Garrido, A. Pérez, M. Carmona, J.F. Rodríguez

O10. GREEN POLYMERS FROM BIOBASED-MONOMERS: KINETICS OF FREE-RADICAL

POLYMERIZATION OF ITACONIC ACID. ... 20 A. Wesołowska,S. Bednarz, D. Bogdał

O11. THE INFLUENCE OF VARIOUS CATALYSTS OF EPOXIDATION OF SOYBEAN OIL ON THE COURSE

OF EPOXY FUSION PROCESS AND THE FUNCTION ALITY OF PRODUCTS OBTAINED ... 22 A. Sienkiewicz, P. Czub

O12. PREPARATION OF NANO-HYDROXYAPATITE/CHITOSAN SPONGE-LIKE SCAFFOLDS FOR TISSUE

ENGINEERING... 24 G. Ruphuy, M.M. Dias, J.C. Lopes, M. F. Barreiro

O13. MAGNETIC AND pH RESPONSIVE MICROC APSULES WITH PROTEIN IMMOBILIZATION ... 26

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6th Workshop on Green Chemistry and Nanotechnologies in Polymer Chemistry

ix

P37. MICROENCAPSULATION OF Rosmarinus officinalis L. (ROSEMARY) AQUEOUS EXTRACT FOR

APPLIC ATION IN FUNCTION AL FOODS ...133 A. Ribeiro, C. Caleja, L. Barros, C. Santos -Buelga, I.C.F.R. Ferreira, M.F. Barreiro

P38. MICROENCAPSULATION OF FENNEL AND CHAMOMILE AQUEOUS EXTRACTS FOR APPLICATION

IN COTTAGE CHEESE...135 C. Caleja, A. Ribeiro, I.C.F.R. Ferreira, M.F. Barreiro

P39. FUNCTIONAL SYNTHETIC TURF SYSTEM WITH IMPROVED COMFORT ...137

B. Moura, S. Silva, N. Durães, D. Coelho, L. Rodrigues, F. Monteiro, R. Silva, A. Moreira

P40. CERAMIC MATERIALS WITH IMPROVED THERMAL COMFORT ...139

A. Sampaio, J. Sousa, J. Branquinho, D. Coelho

P41. MEL AMINE-FOR MALDEHYDE RESINS MODIFIED WITH GLYCEROL ...141

A. Henriques, J. Ferra, J.M. Martins, F. Magalhães, L. Carvalho

P42. MODIFYING RIGID POLYURETHANE FOAM MECHANICAL PROPERTIES BY HIGH RENEWABLE

CARBON CONTENT POL YOL MIXTURES ...143 L. Ugarte, T. Calvo-Correas, A. Santamaría-Echart, S. Gómez-Fernández, M.A. Corcuera, A. Eceiza

P43. THE USE OF BIO-BASED ADDITIVES (LIGNIN, STARCH AND CELLULOSE) IN THERMOPLASTIC

POLYURETHANE FORMULATIONS TO ENHANCE THE BIODEGRADABILITY OF FOOTWEAR

COMPONENTS ...145 I.P. Fernandes, M. Barbosa, J.S. Amaral, V. Pinto, M.J. Ferreira, M.F. Barreiro

P44. SYNTHESIS OF H YDROXYAPATITE WITH N ANOPARTICLES INCLUSIONS...147

D. Malina, A. Sobczak-Kupiec, K. Pluta, K. Bialik-Wąs, B. Tyliszczak

P45. DRYING KINETICS AS TOOL FOR DYN AMIC POROSITY OF C ATAL YST-SUPPORT MATERIALS ..149

J.F. Mata-Segreda

P46. PREPARATION OF POLY(URETHANE-UREA) MICROCAPSULES BY INTERFACIAL

POLYMERIZATION: EFFECT OF PEG MOLECULAR WEIGHT ...151 M. Silva, I.M.D. Martins, M.F. Barreiro, M.M.Q. Dias, A.E. Rodrigues

P47. BIODEGRADATION PRETREATMENT OF WOOD OF E. grandis, E. dunni, AND E. b entami TO WORK

IN BIORREFINERY PROCESSES...153 M. Lopretti, S. Baldyga, M. Gonzalez, L. Olazabal, M. Torres

P48. MICROENCAPSULATION OF Ceratonia siliqua L. EXTRACT FOR FOOD PURPOSES: EFFECT OF

EXTR ACT/ALGINATE R ATIO...155 I. Rached, I.P. Fernandes, L. Barros, A.E. Rodrigues, A. Ferchichi, I.C.F.R. Ferreira, M.F. Barreiro

P49. NATURAL ADDITIVES FOR REDUCING FORMALDEHYDE EMISSIONS IN UREA-FORMALDEHYDE

RESINS...157 F. Pereira, N. Paiva, J. Ferra, J.M. Martins, F. Magalhães, L. Carvalho

P50. PREPARATION AND CHARACTERIZATION OF POLYSACCHARIDES/PVA BLEND NANOFIBROUS

MEMBR ANES PREPARED BY ELECTROSPINNING ...160 A. Sampaio, C. Silva, D. Coelho, A. Zille

P51. VALORISATION OF ALMOND AGRO-INDUSTRIAL RESIDUES: PRODUCTION OF BIOPOLYOLS

FROM ALMOND SHELL ...162 J.A. Pinto, I.P. Fernandes, M.F. Barreiro

P52. MICROENCAPSULATION OF PLANT EXTRACTS RICH IN APIGENIN TO BE USED AS

CHEMOPREVENTIVE AGENTS IN FUNCTION AL FOODS ...164 F.S. Oliveira, R.C. Calhelha, I.P. Fernandes , B.D. Junior, I.C.F.R. Ferreira, M.F. Barreiro

P53. POLYUREAURETH ANES WITH RAP ESEED POL YOL FOR TECHNICAL APPLIC ATIONS ...166

M. Auguścik, J. Ryszkowska, M. Zieleniewska, M. Kurańska, A. Prociak, W. Karalus, K. Pietrzak

P54. INVESTIGATION OF TUNISIAN AGRICULTURAL RESIDUES TO PRODUCE CELLULOSE

NANOCRYSTALS AND NANOFIBRILLAR CELLULOSE: APPLICATION TO NANOCOMPOSITE MATERIALS ...168

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6th Workshop on Green Chemistry and Nanotechnologies in Polymer Chemistry

164

P52. MICROENCAPSULATION OF PLANT EXTRACTS RICH IN

APIGENIN TO BE USED AS CHEMOPREVENTIVE AGENTS IN

FUNCTIONAL FOODS

F.S. Oliveira

1,2

, R.C. Calhelha

2

, I.P. Fernandes

1

, B.D. Junior

3

, I.C.F.R. Ferreira

2,*

,

M.F. Barreiro

1,*

1

Laboratory of Separation and Reaction Engineering (LSRE), Associate Laboratory LSRE -LCM/IPB,

Campus de Santa Apolónia, 1134, 5301-857 Bragança, Portugal.

2

Mountain Research Centre (CIMO), ESA, IPB, Campus de Santa Apolónia, 1172, 5301-855

Bragança, Portugal.

3 Federal University of Technology – Parana (UTFPR), Campus Campo Mourão Via Rosalina Maria

dos Santos,1233,+55 44 3528-1400 Campo Mourão, Paraná, Brazil. *iferreira@ipb.pt, barreiro@ipb.pt

Introduction

Angiogenesis is the process by which new blood vessels are formed from pre-existing vasculature, being a key process that leads to tumor development. Excessive angiogenesis occurs when diseased cells produce abnormally large amounts of angiogenesis factors (e.g. vascular endothelial growth factor (VEGF)) [1]. Some studies recognize phenolic compounds as chemopreventive agents; flavonoids seem to suppress the growth of tumor cells modifying the cell cycle and inducing apoptosis in several tumor cell lines [2]. Among them, apigenin derivatives have been recognized as having antiangiogenic effects on tumor cells being this related to a decrease in VEGF expression or to a VEGFR inhibition [3]. According to Ferreira et al. previous research, Arenaria montana L. is rich in apigenin derivatives [4]. Therefore, this plant source is ideal to prepare apigenin rich extracts to be used as chemoprevent i ve agents in functional foods. However, bioactive compounds are generally recognized as presenting problems of instability, which can weaken their bioavailability and potential benefits. Therefore, the use of microencapsulation is studied here as a way to confer protection and increasing the efficacy of functional foods incorporating these extracts [5].

In this work, a hydroethanolic extract prepared from A. montana was evaluated for its in vitro antiangiogenic effects, being further microencapsulated to be used as chemopreventive agent in functional yogurts.

Experimental

The bioactive ingredient was obtained from Arenaria montana L. through an extraction with ethanol: water 80:20 (v/v). The obtained extract was evaluated in terms of inhibitory activity of the tyrosine kinase intracellular domain of the Vascular Endothelium Growth Factor Receptor-2 (VEGFR-2) through an enzymatic assay. The microspheres were prepared by using an atomization/coagulation technique where a solution of sodium alginate containing the extract (10 mL, extract/sodium alginate ratio of 50/400 (mg/mg)) was atomized through a nozzle (0.35 mm diameter) and coagulated in a calcium chloride solution (250 mL, 4% (v/v)). The forming microspheres were characterized by optical microscopy (OM) during the microencapsulation process to monitor morphology evolution. The encapsulation efficienc y

(EE) was evaluated by HPLC-DAD based on apigenin (the major extract’s aglycone). Additionally, free

and microencapsulated extracts were incorporated into yogurt samples that were thereafter evaluat ed in terms of in vitro antiangiogenic activity and nutritional composition at two different storage times (0 and 3 days).

Results and discussion

The A. montana extract showed capacity to inhibit the phosphorylation of VEGFR-2 (IC50=63.13 µg/ml),

according to the performed enzymatic fluorescence resonance energy transfer (FRET)-based assay. This extract was microencapsulated and the obtained microspheres were observed by OM immediately after the atomization and after 4 hours in contact with the coagulation solution (Fig 1). This analysis confirmed that the process was conducted successfully. The observed microspheres had a spherical morphology and no agglomeration was detected (they were presented as individualized structures). The determined EE pointed out a value reaching 100% since no apigenin (the major extract’s aglycone) was detected, both in the coagulation and washing solutions.

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6th Workshop on Green Chemistry and Nanotechnologies in Polymer Chemistry

165

Fig. 1. Optical microscopy of the microcapsules along the microencapsulation process: A - Microspheres after being sprayed (initial time of the coagulation process); B - Microspheres after coagulation; C- Microspheres after lyophilization (storage form).

The amount of the incorporated extract in the yogurt samples (free or microencapsulated) was twice the

IC50 value which is in accordance with the apigenin daily recommended dose and its relative

concentration in the extract (48%, w/w). For the yogurt added with the free form, and comparatively with the microencapsulated form, an initially higher antiangiogenic activity was observed. Nevertheless, a decrease was observed for t3 (3 days), which can be associated with the extract degradation. On the contrary, in the case of using the microencapsulated form, an increase of antiangiogenic activity was observed from t0 (initial time) to t3. This could be correlated with an effective protection provided by the used microencapsulation process, together with a sustained release of the extract with time.

Conclusions

The atomization/coagulation technique allowed the production of viable microspheres enriched with the plant extract. This final ingredient was effectively incorporated into yogurts, protecting the extract and envisaging the development of novel functional foods with chemopreventive effects. The evaluation of the nutritional composition is under progress.

Acknowledgements

FCT for financial support to CIMO (Project PEst-OE/AGR/UI0690/2014). FCT/MEC and FEDER under Program PT2020 for financial support to LSRE (Project UID/EQU/50020/2013). QREN, ON2 and FEDER (NORTE-07-0124-FE DER-000014) and PRODER (Project nº 46577- PlantLact). The authors also thank Ana Maria Carvalho for providing Arenaria montana L. samples.

References

[1] T.-P. Fan, J.-C. Yeh, K. H. Leung, P. Y. K. Yue and R. N. S Wong, Trend. Pharmacol. Sci., 27, (2006), 297-309.

[2] C. Kandaswami, L.T. Lee, P. P. Lee, J. J. Hwang, F. C. Ke, Y. T. Huang and M. T. Lee, In Vivo, 19, (2005), 895-909.

[3] M. Osada, S. Imaoka, Y. Funae, FEBS Lett. 575, (2004), 59-63.

[4] E. Pereira, L. Barros, R.C. Calhelha, M. Dueñas, A.M. Carvalho, C. Santos-Buelga, I.C.F.R. Ferreira. Food Func. 5, (2014), 1848-1855.

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