SYNTHESIS OF

ANTIBACTERIAL POLYESTERS

Author:
Carlos David Cumba Burgos

Organic Chemistry II P1

Ph. D. Haci Baykara

21/01/2019

GUAYAQUIL - ECUADOR
 Table of contents

Summary
1. Introduction ............................................................................................................... 2

1.1. Purpose............................................................................................................... 3

1.2. Scope .................................................................................................................. 3

2. Method ...................................................................................................................... 3

2.1. Literature review ................................................................................................ 4

3. Conclusions ............................................................................................................... 8

4. Recommendations and implementation .................................................................... 8

5. Declaration/Disclaimer.............................................................................................. 9

List of figures
Illustration I. Synthesis of the monomer. Drawnby Chemsketch. .................................... 5
Illustration II. Synthesis of the polymer. Drawn in Chemsketch ..................................... 6

List of tables

Table I. Permeability properties of released gases ........................................................... 6

Table II. Diffusivity and solubility data of the released gases ......................................... 7

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 Summary

This document deals with the synthesis of antibacterial polyester, applying a simple
ultrasonic irradiation process, which allows to improve the gas separation performance,
together with the cellulose and bionanocomposite silica mixture, where the antibacterial
activity of the synthesized polyester is explained in detail. together with its applications,
and identifying the factors that allow the synthesis to be given in the best way. The
prediction of 1 H-NMR of one of the molecules studied and the expected mass fragments
thereof was included.

1. Introduction

Nowadays, studies have been made to synthesize polymers with antibacterial activity, by
modifying their structure with antibacterial agents. At present, there are many fibers in
the market that consist of antibacterial activity, these are divided into: products where the
fibers are treated with alkoxysilane, and products containing inorganic substances.1

Currently, it seeks to reduce the impact of pollution to the environment caused by the use
of polymers, modifying their structures with substances that are biodegradable. As it is in
the case of the formation of polymers that have cellulose in their composition. Cellulose
is a renewable and natural biopolymer, which is found in abundance in plants, has an
important feature where it does not melt before thermal degradation. The properties of
cellulose will depend on its type, whether for its density, state or the capacity to be
biodegradable.2

Archaeological analysis of samples. The use of nanometric cellulose is linked both to its
dimensions and to the different types of chemical processes used for its isolation, since
depending on the final product the presence of traces of other chemical substances can
generate harmful or counterproductive effects. That is why cellulose of bacterial origin
has been privileged for use in biomedical applications, particularly because thanks to its
surface it allows the fixation and proliferation of different types of cells, while that of
plant origin has been in used in various fields of use including food or electronic.3

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 1.1. Purpose

To know in detail the application and utility of polyester synthesis with antibacterial
activity, identifying a higher performance method, which involves modifying the
structure of polyester with cellulose and bionanocomposite silicon, in such a way that it
has a better environmental impact at the moment of its degradation.
Finally, analyze the characterization of a polyester by predicting 1 H-NMR and the
expected mass fragments.

1.2. Scope

To inform students about organic chemistry II in ESPOL, on the importance of

antibacterial polyester synthesis, considering the factors that influence to obtain a
synthesis of higher performance.

2. Method

This document will focus on the process for the synthesis of a polyester with antibacterial
activity, considering the main factors that influence the reaction, taking into account that
it seeks to modify its structure with cellulose and silicon bianocomposite so that in this
way decrease the environmental impact, at the time of its degradation.4

The knowledge that was compiled to elaborate this document was found in several
external sources, such as documents, Scientifics documents and articles that talk about
the different methods and factors that influence the synthesis of antibacterial polyester,
as well as its importance within society. The characterization by 1H-NMR of a polyester
with specific antibacterial activity is mentioned and analyzed, using the spectroscopic IR

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of a compound that will be used to explain the behavior of this functional group in this
characterization.5

The information acquired in this document will serve to clarify doubts about future
research or experiments related to the synthesis of antibacterial polyester and
corresponding infrared spectroscopy.6

2.1. Literature review

To synthesize an antibacterial polyester, in this case, first proceed to synthesize the

monomer 1- (4- (3,5-bis (trifluoromethyl) phenoxy) phenyl) -3,4 dihydroxypyrrolidine-
2,5-dione chiral, from of the reaction of 3,5-bis (trifluoromethyl) phenol and 1-chloro-4-
nitrobenzene, using potassium carbonate in the medium, with DMAc, then it was poured
into methane and recrystallized from glacial acetic acid to obtain the nitro monomer .
In the second step, 4- (3,5-bis (trifluoromethyl) phenoxy) benzenamine and the chiral
reagent L (-) - tartaric acid are reacted with DMF to obtain the monomer C18H11F6NO5.

Once the monomer is obtained, the polymerization is carried out in the following manner.
The monomer is reacted with a solution of Pyridine and tosyl chloride (TsCl), and then
treated with DMF, a solution of diacid was added to the mixture, to give rise to the
polymerization.7

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Illustration I. Synthesis of the monomer. Drawnby Chemsketch.

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 Illustration II. Synthesis of the polymer. Drawn in Chemsketch

As a next step, it is necessary to modify nanofiber cellulose and silica by means of

ultrasonic irradiation. Once the surface functionalization of silica nanoparticles with
cellulose nanofibers was obtained. The synthesis of polyester / cellulose / silica is carried
out.

Properties of permeation gases

The permeability of gases present in polyester / cellulose / silica, are oxygen, carbon
dioxide, methane and nitrogen, which have the following order of permeability: CH4 <N2
<O2 <CO2.8

The permeation of the molecules by means of fabrics of polymers is given by diffusion,

considering that the polyester is conductive, we can say that the isolation of gases is given
as a sieving.

Gas Condensability Kinetic diameter (A)

temperatura (K)
CO2 195 3,30
O2 107 3,46
N2 71 3,64
CH4 149 3,80
Table I. Permeability properties of released gases

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From the addition of cellulose particles and silicon to polyester, the selectivity for
solubility levels varies much more than diffusivity, in other words it improves the
insulation properties of polyester gases. 9

Membrane Diffusivity selectivity Solubility selectivity

DO2/DN2 DCO2/DN2 DCO2/DCH4 SO2/SN2 SCO2/SN2 SCO2/SCH4
Pure Poliester 4.25 3.66 3.96 3.35 19.43 9.98
Poliéster/cellu 4.77 3.45 3.85 3.26 21.53 10.33
losa/silica
(4%)
Poliéster/cellu 4.81 3.25 3.87 3.23 22.75 11.87
losa/silica
(8%)
Poliéster/cellu 4.92 3.29 3.76 3.25 24.97 12.32
losa/silica
(12%)
Table II. Diffusivity and solubility data of the released gases

Characterization of polyester

The expected FT-IR spectra of Polyester are:

- the bands of C = O ester at 1755, 1727 cm-1

- 1352 cm-1 stretch of C - N
- 733 cm-1 for C = O flexion.

Also in the 1H NMR spectrum of Polyester, there should be no hydroxyl or acid ions at
10-12 ppm, which would indicate that the polyester was completely formed.

Characterization of polyester / cellulose / silica

The FT-IR spectra for cellulose, silica and cellulose / silica nanocomposites are expected
following peaks:

- -the main absorption bands at 3400, 1560 and 1365 cm-1, belonging to OH
- -the 450 cm-1 peak for Si - O bond.

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In the cellulose spectrum:
- -The stretch and flexion modes of the -OH group would be between 3455 and
1525 cm-1.
- The peak of 1030 cm-1 would correspond to the C - O stretch of the cellulose.

3. Conclusions

Once the polyester is obtained it is treated with ultrasonic irradiation of a high level of
intensity, in this way the BNC particles were modified with the cellulose.

Cellulose / BNC is used to increase the thermal resistance capacity of polyester fabrics.
The gas permeability varies as follows: PCH4 (38%) <PN2 (58%) <PCO2 (88%) <PO2
(98%).

Link silica nanoparticles to polyester, increase the insulation performance of gases

The diffusion coefficient for gases is directly proportional to the kinetic diameter, less for
CO2.

One of the most important factors is the temperature, as could be observed was a factor
that influenced a lot in regard to the reactions, and also influenced significantly to certain
properties of the compound.

4. Recommendations and implementation

- The cellulose / silica nanoparticles allow the polyester substance to have a

degradation that causes a lower environmental impact.

- When performing any type of reaction that involves the synthesis of:
polymerization, and the addition of cellulose / silica nanoparticles to polyester, it
is important to consider that temperature is a factor that influences the results.

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 - For the spectroscopic characterization by 1H NMR, it is important to analyze all
the peaks that are present in the spectra that appear the functional groups and
certain interferences that may occur.

The implementations that could be considered for the synthesis of antibacterial

polyester are the following:

- In spite of having several methods to give an antibacterial use to a polymer, in

this case polyester, the function of the present method is that it is easy to be
degraded.

- It is the cellulose / silica particles that allow the polyester to fulfill an

antibacterial function, due to its properties.

5. Declaration/Disclaimer

I accept that I have not been able to use the information or the subject of the present
document for some kind of future work and I accept that Ph.D. Haci Baykara could use it
for whatever purpose he wants.

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Observations by Diana Angelica Velastegui Nieve

 Your papers lack the spacing between lines and paragraph that should be 1.5

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