Ingeniería y Tecnología

Artículo arbitrado

Synthesis of an unconventional cationic

surfactant precursor

Síntesis del precursor de un surfactante catiónico

no convencional

KARLA LIZETTE TOVAR-CARRILLO , ROSA ALICIA SAUCEDO-ACUÑA , ALEJANDRO MARTÍNEZ-

1,4

MARTÍNEZ , FERNANDO PLENGE-TELLECHEA , ERASTO ARMANDO ZARAGOZA-CONTRERAS

Y TAKAOMI KOBAYASHI

Recibido: Agosto 23, 2010

Aceptado: Noviembre 23, 2010

Resumen

Abstract

Este trabajo consiste en el desarrollo de un precursor de

surfactante catiónico no convencional empleando el método

estándar de síntesis de éteres de Williamsom. Tratamos de

diseñar un nuevo tipo de surfactantes heterogéminis con un

espaciador rígido y grupos de cabeza no idénticos en la

estructura del surfactante. En la síntesis sugerida establecemos

el paso preliminar para la obtención un surfactante con dos

anillos aromáticos como espaciador rígido. El precursor

sintetizado proporciona a la estructura del surfactante un

espaciador rígido debido a la presencia del grupo bifenilo,

esperando que el surfactante presente una reducción tanto de

la curvatura de los agregados micelares, así como de la

concentración micelar crítica (CMC), en comparación con

reportes previos, donde emplean surfactantes convencionales.

Para establecer los pasos de la síntesis se varía la temperatura

en el tiempo de reacción, así como la velocidad de adición del

compuesto que contiene el grupo de cabeza, deseado que se

pretende añadir a la estructura del surfactante propuesto. Para

la caracterización se emplearon las técnicas de espectroscopia

de infrarrojo (FT-IR) y resonancia magnética nuclear (RMN).

The present research is about the development of a precursor

of unconventional cationic surfactant by using the standard

procedures of the Williamson ether synthesis. It has been

intended to design a new type of heterogemini surfactant with

a rigid spacer and non identical head groups in the structure of

the surfactant. In the synthesis suggested, the preliminary step

to obtain a surfactant structure with two aromatic rings as rigid

spacer has been established. This synthesized precursor

provides with a rigid spacer to the structure of the surfactant

due to the presence of a biphenyl group; it is expected that,

with this surfactant, it further presents a reduction on both the

curvature of micellar aggregates as well as the Critical Micelle

Concentration (CMC) in respect of those previous reports where

conventional surfactants are used. To establish the steps of

the synthesis, the temperature during the time of reaction has

been varied, as well as the velocity of addition of the compound

containing the head group which is pretended to be added to

the surfactant structure proposed. For the characterization,

the infrared spectroscopy technique (FT-IR) and the Nuclear

Magnetic Resonance (NMR) were used.

Palabras clave: surfactante, síntesis, precursor, CMC.

Keywords: surfactants, synthesis, precursor, CMC.

Introduction

emini surfactants are a new kind of surfactants. They have amphiphiles composed of

two identical hydrophobic chains linked with a spacer moiety at the two head groups,

(

Menger et al., 1991). Since they have amphiphilic behaviour and form micelles, surface

properties of Gemini surfactants were studied and described in several reviews (Borse et al., 2006).

Many studies have shown that the spacer group has much effect on the properties of the solution in

this kind of surfactants. In a comparison with ordinary monomeric surfactants, the CMC of the

Gemini surfactants is considerably lower than ordinary surfactants.

________________________________

UACJ. Instituto de Ciencias Biomédicas. Ave. Anillo envolvente del Pronaf y Estocolmo S/N. Cd.Juárez, Chih.México

CIMAV. Grupo de Polímeros. Miguel de Cervantes. Num. 120. Complejo Industrial Chihuahua, Chih. México

Department of Materials Science and Technology, Nagaoka University of Technology, 1603-1 Kamitomioka, Nagaoka, Niigata 940-2188, Japan

Dirección electrónica del autor de correspondencia: Fernando Plenge-Tellechea, fplenge@uacj.mx

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KARLA LIZETTE TOVAR-CARRILLO, ROSA ALICIA SAUCEDO-ACUÑA, ALEJANDRO MARTÍNEZ-MARTÍNEZ, FERNANDO PLENGE-TELLECHEA, ERASTO

ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

A Gemini surfactant with two hydrocarbon

chains and two hydrophilic head groups in a

molecule is commonly known for exhibiting the

following unusual properties: a CMC lower than

one or two orders of magnitude, more efficiency

in lowering the surface tension of water, the

properties of the theoretical bases at a relatively

low concentration, comparing with monomeric

and ordinary surfactants. Most Gemini

surfactants have a symmetrical structure

comprising identical hydrocarbon chain lengths

and hydrophilic regions. Our current area of

interest is a new generation of Gemini

surfactants, which would have better properties

and unique characteristics in the adsorption and

micellization process. In recent research,

carried out with Gemini surfactants in which the

head groups were chemically non identical,

showed good surface-active properties, such as

low CMC and high efficiency in lowering the

surface tension, and aggregation behavior in the

solution.

molecular assemblies, called micelles. The

formed micelles are of various types, shapes

and sizes, such as globular, cylindrical and

spherical (Maiti et al., 2000). The characteristics

of these aggregates are governed by the

molecular structure and the conditions of the

solution of the surfactant, in addition to physical

parameters (Borse et al., 2006). In recent years,

several researchers designed newer molecular

structures of surfactants with greater surface

activity; these molecules were called bis-

surfactants, later, they were called «gemini»

surfactants (Menger et al., 2000; Oda et al.,

2001). This kind of surfactants is considerably

more surface active than the conventional

surfactants called «monomeric» surfactants (Li

et al., 1991; Rosen et al., 1994), the difference

stems from the structure of a conventional

surfactant has a single hydrophobic tail

connected to an ionic group or polar head group,

whereas a gemini surfactant has in a sequence

a hydrocarbon chain, an ionic group, a spacer,

a second ionic group and another hydrocarbon

tail (Zana et al, 1995; Menger et al., 2001). The

spacer can be formed of different natures such

as short or flexible chains as methylene groups,

rigid as stilbene, polar as polyether, and non polar

as aliphatic or aromatic groups (Bunton et al.,

A new family of materials based on

unconventional structure of surfactants is

undergoing an exploration in several laboratories.

These surfactants present a different structure

from the surfactants named geminis. The

resulting materials can be self-assembled into

both side-chain-like polymers (Edlund et al.,

971). The ionic groups can be positive as

ammonium or negative as phosphate. The

majority of geminis have symmetrical structures

with two identical polar groups and two identical

chains.

1996). The most recent research on surfactants

are focused in obtaining high-performance on

areas of high-technology such as electronics,

printing, magnetic recording, biotechnology and

microelectronics (Lee et al., 1995).

Moreover, some unsymmetrical geminis and

geminis with three or more polar groups or tails

have been recently reported. One type of these

unsymmetrical geminis is the bis-quaternary

surfactants with a general molecular formula

C H N+(CH ) – (CH )-N+(CH ) C H₂_n₊₁, 2Br-

Although cationic surfactant complies with

only a small portion of the market, its importance

in practical applications continues to grow. It is

used as antibacterial, liquid crystals, gene

transfection agents, in road repairs, for reactions

and in preparation of crystalline mesoporous

materials (Esumi et al., 1998).

2n+1

3 2

and are referred as m-s-m DMA (DMA = dimethyl

ammonium bromide) surfactants (Srivastava et

al., 1998; Deacon et al., 2003). These surfactants

possess unique properties in their solution such

as very low critical micellar concentration (CMC),

high detergency, high solubilization and high

surface wetting capability; these properties give

them a wide range of applications in diverse areas

Conventional surfactants molecules are

generally composed of two parts: one polar head

and one alkyl chain, incompatible with one

another. They are known for their tendency to

complete self-association and to develop super

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ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

such as mining, petroleum, chemical,

pharmaceutical industries, and biochemical

research. They are also used as preservatives

during the refluxing of the wise drop solution, and

the refluxing continued for 72 h; the synthesis

scheme is shown in Figure 1. The amount of

products was registered after changing the time

and temperature of reaction, as well as the velocity

in which the compound contained the head group

of the surfactant.

(Bakshi et al., 2005), anticorrosive (Koopal et al.,

1995; Sharma et al., 2005) and antimicrobial

agents (Menger et al., 1991).

In the early 1990s, (Menger et al., 1991), the

term gemini was assigned to these bis-

surfactants that have a rigid spacer such as

benzene or stilbene. The term was, then,

extended to other bis or double tailed surfactants,

irrespective of the nature of the spacer.

Furthermore, it was examined the effect of the

heterocyclic head group and the acetylenic

spacer on the aggregation properties of cationic

geminis (Menger et al., 2000). Surfactants

containing rigid hydrophobic groups are also

called unconventional surfactants. The synthesis

and behavior of these surfactants have been

widely reported, however, the use of this new

amphiphiles in the synthesis of polymers through

heterogeneous polymerization techniques

Most of the bi-substituted product was

precipitated during this time and was collected after

the mixture cooled at 2°C. The remaining solution

contained most of the mono-substituted product.

HCl concentrated was added to this solution, upon

which an emulsion was formed. The emulsion was

stirred for 30 min and then filtered and washed

with water three times. The resulting white paste

was dried at 80°C during three days. The dried

paste was stirred for 20 min in chloroform and then

filtered five times (during this step, the entire mono-

substituted product was removed from the white

paste), and re-crystallized.

In the second step, two equivalents of KOH

reagent (Baker) were dissolved into dry methanol,

to give a 5% (v/v) solution. The mono-substituted

product was added, and a clear colorless solution

was obtained on refluxing. An equivalent of 1,6-

dibromopentane was added all at once to the

refluxing solution. The refluxing continued for 72

h after overnight refluxing, the bi-substituted

product precipitated; as a result, the volume of

the mixture was reduced. The resulting

precipitated product was collected and washed

with 99.55% (v/v) of ethanol.

(

emulsion or mini-emulsion) has been hardly

studied (Zaragoza et al., 2003). It has been

recently reported that this surfactants can be

used as potential gene delivery agents. Due to

this application, the number of research on the

molecular structure and their effect on solution

of these surfactants have been increased today

because these compounds offer an important

tool for different fields as biotechnology,

biochemistry, genetics, and molecular biology.

The aim of this work and its originality establish

the preliminary step of an unconventional cationic

surfactant synthesis, with a rigid spacer structure

provided from the molecule of bisphenol.

Figure 1. Scheme of unconventional cationic surfactant

precursor synthesis. A, B, C and D are important steps carried

out on the synthesis previously described.

Materials and Methods

Synthesis. The precursor of this surfactant

was prepared in two steps, by using the standard

procedures of the Williamson ether synthesis

(Brandys et al., 1996). In the first step, the starting

reactant, 4,4’-bisphenol 97% (Aldrich), was

neutralized with two equivalent of 5% (p/v) sodium

solution 3-8 mm spheres (Aldrich) in water. 1

equivalent of 1-bromopentane 99% (Aldrich) was

dissolved separately in 99.5% ethanol and added

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KARLA LIZETTE TOVAR-CARRILLO, ROSA ALICIA SAUCEDO-ACUÑA, ALEJANDRO MARTÍNEZ-MARTÍNEZ, FERNANDO PLENGE-TELLECHEA, ERASTO

ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

Figure 2. Summary of the amount of compound obtained when

the reaction temperature was varying.

Analysis. By using the infrared

spectroscopy equipment Perkin Elmer brand

GXATR model, infrared spectra were obtained.

The 1H NMR spectra were obtained by JNM

GX400 FT-MNR.

Results and Discussion

Synthesis. To establish the optimum

conditions to synthesize the mentioned

surfactant, it was necessary to evaluate the

effects of the reaction temperature, reaction

time, and the adding velocity of the compound,

which are going to give the head group to the

structure of the surfactant. The analysis of these

conditions was based on the impact of the

amount of synthesized product. To analyze the

effect of change in the conditions of the reaction,

the amount of the obtained compound during

the synthesis was registered and the interaction

between the conditions was examined. The

obtained data on the references suggested a

starting temperature of 70ˆC, due to this result,

the effect of the temperature was analyzed firstly

Another experiments show the summary of

the amount of compound in grams obtained

when the time reaction was varying (Figure 3).

If the reaction time is less than 48 h the amount

of compound decreases and the un-reacted

reactant amount increases. If the reaction time

is more than 48 h the amount of compound does

not change.

Figure 3. Summary of the amount of compound obtained when

the time reaction was varying.

(Bradys and Bazuin. 1998).

A summary of the results obtained in the

experiments is shown below, only with the

variation in the reaction temperature (Figure 2).

The amount of compound did not change at

higher temperatures than 120°C. However, at

lower temperatures than 90°C, the amount of

compound decreases significantly. This

phenomenon could happen because at lower

temperature it is more difficult for the

molecules of bisphenol to be out of phase when

a molecule of a reactant is attached, and more

time available makes possible the substitution

of the second -OH bond on the molecule,

decreasing the amount of mono substituted

compound, which is needed for the surfactant

structure proposed.

Through the bisphenol has two -OH bounds

which can participate in the reaction and the

main point is obtained the substitution of only

one group, it was expected that decreasing the

velocity in which the reactant is adding into the

reaction the amount of mono-substituted

compound will increase. For this, the adding

velocity of the reactant was analyzed. It was

found that, when the adding velocity decreases

the amount of compound increases significantly.

This might be, because the number of the

molecules in the reactant is lower than the

molecules of the bisphenol available, increasing

the possibility of reaction of only one -OH bond

with the reactant. On the other hand, if the adding

First of all, the effect of the temperature

was analyzed as well as the reaction time,

leaving constant the temperature at which the

maximum of compound was obtained. The

minimum time reaction was taken from

references (Bradys and Bazuin. 1998).

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KARLA LIZETTE TOVAR-CARRILLO, ROSA ALICIA SAUCEDO-ACUÑA, ALEJANDRO MARTÍNEZ-MARTÍNEZ, FERNANDO PLENGE-TELLECHEA, ERASTO

ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

velocity increases the opposite effect is obtained,

since the number of molecules in the reactant

increases and the second -OH bond can be

easily substituted (Figure 4).

The results during the infrared spectra of

the substitute compound by only one hydroxyl

group (Figure 6) show a region near to 3300 cm

representing a free hydroxyl group of the

molecule. Aromatic C-H stretching bands occur

between 3100 and 3000 cm . Skeletal vibrations

Figure 4. Summary of the amount of compound obtained when

the adding velocity was varying.

-1

involving carbon-carbon stretching within the

ring, absorb in the 1600-1585 and 1500-1400

Figure 6. Infrared spectra analyzed at room temperature of

substitute compound by only one hydroxyl group.

Infrared Analysis. The obtained products

were filtered and dried to analyze them with

infrared spectroscopy. The two important areas

for preliminary analysis of infrared spectra are

the regions at 4000 – 1300 and 900 – 650 cm .

Figure 5 shows the spectra of the starting

reactant. This spectrum has illustrated important

infrared bands, which are very important for the

synthesis. The non-hydrogen-bonded or free

hydroxyl group of alcohols and phenols absorbs

The decrease of the intensity of the infrared

strongly around 3500 cm region. The C-O

stretching vibrations in phenols produce a strong

spectrum around 3300 cm of the starting

reactant, was caused by the substitution of a

hydroxyl group of the molecule. Bands near to

band in the 1200 – 1000 cm region of the

spectrum. The C-O stretching mode is coupled

with the adjacent C-C stretching vibration. The

-1

930 cm are attributed to bonds C-O-C of the

nucleophilic substitution between the starting

reactant and 1-bromoalcane.

regions around 1580, 1494, 1100 and 900 cm

are typically of bisphenoles compounds.

-1

The infrared bands near to 1494 cm involve

the next non-aromatic bonds: C-C and C-H.

Figure 5. Infrared spectra at room temperature of the starting

reagent 4,4’-bisphenol.

What is more, the region around 809 cm is

caused by the substitution of the 4,4-bisphenol;

the figure 2 shows a low intensity variation

caused by these groups on the molecule. Finally,

the appearance of the infrared band near to 590

cm involves stretching C-C and C-H bonds that

confirm the substitution on the molecule of

bisphenol bond to C-O. This suggest that the

interaction of C-O bonding out-of-plane with C-

C stretching and the C-H of the aliphatic chain

as result of the substitution of the molecule of

bisphenol, to analyze the spectrum regions near

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KARLA LIZETTE TOVAR-CARRILLO, ROSA ALICIA SAUCEDO-ACUÑA, ALEJANDRO MARTÍNEZ-MARTÍNEZ, FERNANDO PLENGE-TELLECHEA, ERASTO

ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

to 2930, 1490, 809 and 509 cm reported (Zhao

et al., 2007). This experiment also shows the

infrared spectra of the sub- product in the first

part of the synthesis (Figure 6). In this spectrum

it can be appreciated an increase in the intensity

Infrared spectra in figure 7 are similar to

infrared spectra in figure 3, due to the aliphatic

chains in the molecule of bisphenol. The region

near to 2900-2800 represents the stretching C-

H of the aromatic ring, and typical stretching

bands C-O-C of aril ester compounds. The band

of the infrared band near to 2940 cm (Figure

), in which the C-O-C stretching bonding was

involved. This increase is caused by the

elimination of the molecule of bisphenol free

hydroxyl groups forming bonds C-O-C.

near to 1600 cm is attributed to the stretching

C=C of the aromatic ring, infrared bands close

to 1500 cm are attributed to aliphatic chains

bonding to the compounds of bisphenol.

On the other hand, the increase in the

intensity of the infrared band near to 1490 cm

is attributed to the growing interaction between

the C-C and the C-H bonds of the aliphatic chain

with the molecule of bisphenol shown in Figure

The region near to 1300-1200 cm shows

the stretching C-O out-of-plane, this band

increases its intensity shown in the spectrum

of figure 3. Bands around 1100 cm are

attributed to the stretching C-H in-the-plane

of the aromatic ring, like in the infrared

spectrum (Figure 3). The most important

difference between the spectrum in figure 3

and the one shown in figure 4 is the decrease

, through the elimination of another free

hydroxyl group within the molecule.

Another region that support the bi-

substitution of the molecule of bisphenol, is the

appearance of the infrared bands near to 1034

of the bands near to 700 – 500 cm , due to

the difference of the aliphatic chain added to

the molecule of bisphenol (Chorro et al.,

1998).

cm , that involves stretching C-O-C bonding to

asymmetric C-O of the compound.

Furthermore, the intensity of the infrared band

near to 825 cm is attributed to the bi-

substitution of the 4,4-bisphenol for aliphatic

chains, which intensity shows a low intensity due

to the deference of the groups bonding to the

molecule of bisphenol. To conclude, the increase

NMR analysis. The obtained products were

filtered and re-crystallized twice with diluted

ethanol, as a result, 1H NMR spectra by JNM

GX400 FT-MNR was obtained.

Figure 8. 1H NMR spectra of the substitute compound by only

of the infrared band near to 590 cm is attributed

to the stretching of the C-C and the C-H of the

aliphatic chains bonding to the C-O out-of-plane

of the bi-substitute molecule.

one hydroxyl group.

Figure 7. Infrared spectra analyzed at room temperature of

substitute compound, substitution of the free hydroxyl groups.

Figure 8 shows the 1H NMR spectra of the

obtained compound during the first part on the

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KARLA LIZETTE TOVAR-CARRILLO, ROSA ALICIA SAUCEDO-ACUÑA, ALEJANDRO MARTÍNEZ-MARTÍNEZ, FERNANDO PLENGE-TELLECHEA, ERASTO

ARMANDO ZARAGOZA-CONTRERAS Y TAKAOMI KOBAYASHI: Synthesis of an unconventional cationic surfactant precursor

synthesis of the surfactant. These spectra

show that the analyzed compound has the

number of hydrogen expected for the molecule

in the first part of the synthesis. This spectrum

also shows that the substitutions of the carbons

that form the chemical structure of the

compound are also the expected on the

structure of the substitute compound by only

one hydroxyl group during the synthesis

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Este artículo es citado así:

Tovar-Carrillo, K. L., R.A. Saucedo-Acuña, A. Martínez-Martínez, F. Plenge-Tellechea, E. A. Zaragoza-

Contreras and T. Kobayashi. 2011: Synthesis of an unconventional cationic surfactant precursor.

TECNOCIENCIA Chihuahua 5(1): 19-26.

Resúmenes curriculares de autor y coautores

KARLA LIZETTE TOVAR CARRILLO. Miembro de la UACJ desde 2005, actualmente estudiante de doctorado de Nagaoka University of

Technology, ha sido profesor de química y auxiliar de laboratorio de química. Ha trabajado en el desarrollo de materiales con fines

biomédicos de 2007 a la fecha, contribuyendo a la obtención y caracterización de los mismos. Ha participado en 6 proyectos de

investigación y tiene 7 publicaciones en revistas nacionales e internacionales.

ROSA ALICIA SAUCEDO ACUÑA. Miembro del Instituto de Ciencias Biomédicas de la UACJ, trabaja en el desarrollo y adecuación de

materiales con fines biomédicos, contribuyendo con el desarrollo de dos matrices poliméricas que han regenerado con éxito tejido

adiposo y muscular en murinos. Es miembro fundador del Consorcio JAP-MEX-USA, miembro del SNI y del CAEC de Diagnóstico

Molecular de la UACJ.

ALEJANDRO MARTÍNEZ MARTÍNEZ. Tiene una amplia trayectoria en bioquímica y neurociencias. Es miembro de la Sociedad Mexicana de

Bioquímica AC, y de la American Society of Neurosciences. En 1991 obtuvo la licenciatura en Biología en la Universidad de

Guadalajara (UDG). Obtuvo el grado de Maestría en Neuroquímica en el Departamento de Química de la UNAM en 1994. En 1997,

culminó sus estudios de Doctorado en Biología en la Universidad de Murcia, España. Realizó varias estancias académicas de

posgrado, entre las que destacan su postdoctorado en la Universidad de California en San Diego (Irving), con una beca de la

fundación hispana PEW, culminando en el 2003. El mismo año, ingresó como Profesor Investigador de tiempo completo a la

Universidad Autónoma de Ciudad Juárez. Cuenta con múltiples publicaciones y capítulos de libros, así como dirección individual de

tesis de pregrado y de grado. Imparte cátedra de ingeniería genética en el programa de química y bioinformática en la Maestría en

Ciencias con orientación en genómica (PNP) y Maestría en Ciencias Químico- Biológicas (PNP).

LUIS FERNANDO PLENGE TELLECHEA. Desde 1990 ingresó como becario interno del laboratorio de reproducción en la Facultad de Ciencias

de la Universidad Autónoma de Baja California. En 1992 culminó sus estudios de Biología en la misma dependencia. Posteriormente

realizó sus estudios de Doctorado en Ciencias Biológicas por la Universidad de Murcia, culminando en 1998. El Dr. Plenge se ha

caracterizado por sus estudios bioquímicos en la rama de proteínas asociadas en membranas. Actualmente labora como profesor

investigador de tiempo completo en la Universidad Autónoma de Ciudad Juárez. Cuenta con múltiples publicaciones y dirección de

tesis de pregrado y de grado. Es actual director en jefe de la revista de ciencias, Ciencia en la Frontera, e imparte la cátedra de

Bioquímica en el programa de Biología y de Estructura y función proteínas en la Maestría en Ciencias con orientación en genómica

(PNP). Actualmente se encuentra en una estancia Posdoctoral en el Border Biomedical Research de la Universidad de Texas en El

Paso desde 2010 al presente, estudiando mecanismos bioquímicos de neurotransportadores.

TAKAOMI KOBAYASHI. Miembro del Departamento de Química de la Nagaoka University of Technology. Ha recibido el premio al mejor

investigador joven en polímeros de Japón, actualmente es presidente del Consorcio JAP-MEX-USA. Su área de investigación es

el desarrollo de materiales poliméricos. Entre los logros más recientes de su equipo de colaboradores es el desarrollo de una nueva

técnica de impresión molecular en la preparación de membranas porosas.

• Vol. V, No. 1 • Enero-Abril 2011 •