Structure property relationship of aliphatic segmented poly(ester amide)s [Elektronische Ressource] / vorgelegt von Priya Garg
224 pages
English

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Structure property relationship of aliphatic segmented poly(ester amide)s [Elektronische Ressource] / vorgelegt von Priya Garg

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224 pages
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Structure-property relationship of aliphatic segmented poly(ester amide)s Von der Fakultät für Mathematik, Informatik und Naturwissenschaften der RWTH Aachen University zur Erlangung des akademischen Grades einer Doktorin der Naturwissenschaften genehmigte Dissertation vorgelegt von Priya Garg, M.Sc. aus Neu Delhi, Indien Berichter: Universitätsprofessor Dr. rer. nat. Martin Möller apl. Prof. Dr. rer. nat Doris Klee Tag der mündlichen Prüfung: 26. Januar 2010 Diese Dissertation ist auf den Internetseiten der Hochschulbibliothek online verfügbar. List of Publications Parts of this thesis are published, submitted to be published, presented at conferences: Articles: Priya Garg, Doris Klee, Helmut Keul, Martin Möller ‘Electrospinning of novel poly(ester amide)s’ Macromolecular Materials and Engineering, 2009, 294, 679 - 690. Priya Garg, Helmut Keul, Doris Klee, Martin Möller ‘Concept and synthesis of poly(ester amide)s with one isolated, two or three consecutive amide bonds randomly distributed along the polyester backbone’ Designed Monomers and Polymers, 2009, 12, 405 – 424. Priya Garg, Helmut Keul, Doris Klee, Martin Möller ‘Thermal properties of poly(ester amide)s with isolated, two adjacent and three adjacent amide groups within a polyester chain’ Macromolecular Chemistry and Physics, 2009, 210, 1754 - 1765.

Informations

Publié par
Publié le 01 janvier 2010
Nombre de lectures 35
Langue English
Poids de l'ouvrage 37 Mo

Extrait




Structure-property relationship of aliphatic
segmented poly(ester amide)s





Von der Fakultät für Mathematik, Informatik und
Naturwissenschaften der RWTH Aachen University zur
Erlangung des akademischen Grades einer Doktorin der
Naturwissenschaften genehmigte Dissertation

vorgelegt von


Priya Garg, M.Sc.
aus Neu Delhi, Indien


Berichter: Universitätsprofessor Dr. rer. nat. Martin Möller
apl. Prof. Dr. rer. nat Doris Klee

Tag der mündlichen Prüfung: 26. Januar 2010


Diese Dissertation ist auf den Internetseiten der Hochschulbibliothek online verfügbar.

List of Publications

Parts of this thesis are published, submitted to be published, presented at conferences:

Articles:

Priya Garg, Doris Klee, Helmut Keul, Martin Möller ‘Electrospinning of novel poly(ester
amide)s’ Macromolecular Materials and Engineering, 2009, 294, 679 - 690.
Priya Garg, Helmut Keul, Doris Klee, Martin Möller ‘Concept and synthesis of poly(ester
amide)s with one isolated, two or three consecutive amide bonds randomly distributed along
the polyester backbone’ Designed Monomers and Polymers, 2009, 12, 405 – 424.
Priya Garg, Helmut Keul, Doris Klee, Martin Möller ‘Thermal properties of poly(ester amide)s
with isolated, two adjacent and three adjacent amide groups within a polyester chain’
Macromolecular Chemistry and Physics, 2009, 210, 1754 - 1765.
Priya Garg, Pratiksha Lohakare, Petra Mela, Martin Möller, Bernhard Blümich, Alina Adams
‘Morphology of novel poly(ester amide)s containing two consecutive amide bonds randomly
distributed along the polyester backbone’ Macromolecular Chemistry and Physics, 2010,
DOI: 10.1002/macp.200900464.
13Alina Adams, Priya Garg, Pratiksha Lohakare, Martin Möller ‘ C solid-state NMR analyses
of poly(ester amide)s containing two consecutive amide bonds randomly distributed along
the polyester backbone’ in preparation.

Posters:

Priya Garg, Helmut Keul, Doris Klee, Martin Möller ‘Degradation and in-vitro biocompatibility
tests of novel poly(ester amide)s’ at Bio & Polymers, GDCh biannual meeting, Aachen 28-30
September 2008.
Pratiksha Lohakare, Alina Adams, Priya Garg, Helmut Keul, Martin Möller, Bernhard
Blümich ‘Structural and morphological studies of novel poly(ester amide)s by solid state
thNMR’ at the 30 Trinational annual discussion meeting ‘Magnetic Resonance in Biology and
Chemistry’, Regensburg, 22-25 September 2008.
Priya Garg, Pratiksha Lohakare, Alina Adams, Doris Klee, Helmut Keul, Martin Möller,
Bernhard Blümich ‘Synthesis of novel poly(ester amide)s and their characterization by solid-
thstate NMR’ at the 14 Rolduc Polymer Meeting, Kerkrade, 18-21 May 2008.
Table of contents


List of symbols and abbreviations i
Summary iv
Zusammenfassung vi


Chapter 1 Introduction and contents of this thesis 1

Chapter 2 Synthesis and characterization of tailor made α,ω-amino 7
alcohols, diols and diamines for the synthesis of
poly(ester amide)s with random distribution of one amide
bond, two consecutive or three consecutive amide bonds

Chapter 3 Synthesis and characterization of poly(ester amide)s with 43
one, two consecutive or three consecutive amide bonds
randomly distributed along the polyester backbone

Chapter 4 Morphology of poly(ester amide)s containing two adjacent 95
amide groups randomly placed along the polyester
backbone

Chapter 5 Degradation and in-vitro biocompatibility of segmented 137
poly(ester amide)s

Chapter 6 Electrospinning of poly(ester amide)s containing two 167
adjacent amide groups randomly placed along the polyester
backbone

Chapter 7 Dispersion of silica nanoparticles in polyamide 187


Acknowledgements 211
Curriculum Vitae 213

List of symbols and abbreviations:

1-A isolated amide series
2-aA 2-adjacent amide series
3-aA 3-adjacent amide series
α cut-off parameter of the Lorentzian line (NMR)
Å angstrom
A amide
ACA 6-aminocaproic acid
AFM atomic force microscopy
CDCl deuterated chloroform 3
CHCl cholorofm 3
CPMAS cross polarization magic angle spinning
° degree
°C degree Celcius
δ chemical shift (NMR)
H enthalpy of crystallization c
H enthalpy of melting m
ν full line width at half height 1/2
DD dipolar decoupling
DMSO dimethyl suphoxide
DMSO-d6 deuterated dimethyl suphoxide
DSC differential scanning calorimetry
DQ double quantum
E ester
EA ester-amide sequence
et al. et alii; et aliae
Eq equation
FDA Food and Drug Administration
FT-IR Fourier transform infra-red spectroscopy
g gram
h hour
HCOOH formic acid
J/g joules per gram
kDa kilodaltons
kHz kilohertz
kV kilovolts
- i - λ wavelength
L litre
M monomer
MAS magic angle spinning
mA microampere
mbar millibar
MeOH methanol
MHz megahertz
μL microlitre
mL millilitre
μm micrometer
mm millimeter
M number average molecular weight n
mol moles
mp melting point
MQ multiple quantum
μs microsecond
μS microSiemens
M weight average molecular weight w
N newton
nm nanometer
NMR nuclear magnetic resonance spectroscopy
Pa Pascals
PA polyamide
PAOS polyalkoxysiloxane
PBA poly(butylene adipate)
PDI polydispersity index
PEAs poly(ester amide)s
PGA poly(glycolic acid)
PLA poly(lactic acid)
PLGA poly(lactic-co-glycolic acid)
ppm parts per million
2r mean square distance between the nearest spins (NMR)
s second
SEC size exclusion chromatography
SEM scanning electron microscopy
Si silicon
- ii - SPMAS single pulse magic angle spinning
θ theta
τ excitation/reconversion time
T tonnes
T crystallization temperature c
TCPS tissue culture polystyrene
TEM transmission electron microscopy
t diffusion time (NMR) d
t evolution time of the DQ coherences DQ
TFA-d deuterated trifluoro acetic acid
T glass transition temperature g
TGA thermal gravimetric analysis
THF tetrahydrofuran
T melting temperature m
t mixing times (NMR) m
v/v volume by volume
WAXD wide angle x-ray diffraction
wt% weight percent


Synthesized monomers

HO-(εClon/C )-NH 5-(4-Amino-butylcarbamoyl)-pentanol; Monomer M1 4 2
HO-(εClon/C )-OH 5-(4-Hydroxy-butylcarbamoyl)-pentanol; Monomer M2 4
HO-(εClon/C )-OH 5-(2-Hydroxy-ethylcarbamoyl)-pentanol; Monomer M3 2
H N-(εClam/C )-NH 6-amino-N-(4-aminobutyl)hexanamide; Monomer M4 2 4 2
H N-(εClam/C )-OH 6-amino-N-(4-hydroxybutyl)hexanamide; Monomer M5 2 4
H N-(εClam/C )-OH 6-amino-N-(3-hydroxypropyl)hexanamide; Monomer M6 2 3
H N-(εClam/C )-OH 6-amino-N-(2-hydroxyethyl)hexanamide; Monomer M7 2 2
HO-(δVal/C )-NH 4-(4-Amino-butylcarbamoyl)-butanol; Monomer M8 4 2


- iii - Summary

This thesis focuses on the synthesis, characterization and applications of aliphatic
segmented poly(ester amide)s (PEA)s for use as potential biomaterials. Three different
series of PEAs with different microstructures containing isolated, two and three adjacent
amide groups within a polybutylene adipate (PBA) chain have been synthesized. Analytical
techniques such as NMR (liquid and solid-state), SEC, DSC, FT-IR, WAXD and microscopy
(AFM, SEM, optical) have been extensively used to characterize the synthesized monomers
and PEAs. Thermal properties have been determined and correlated to features like
morphology and crystallization behaviour; structure-property relationship of these polymers
were established.
The preparation of tailor made monomers for the synthesis of PEAs was carried out by ring
opening of ε-caprolactam, ε-caprolactone or δ-valerolactone with 1,4-diaminobutane, 4-
aminobutanol, 3-aminopropanol and/or 2-aminoethanol. These preformed monomers which
are α,ω-diamines, α,ω-amino alcohols or α,ω-diols, each containing an in-built amide bond,
were obtained in high purity and yields.
Synthesis of the PEAs containing an isolated amide group, two or three adjacent amide
groups was achieved by a two-step melt polycondensation of the preformed monomers with
1,4-butanediol and dimethyl adipate. In the first step, trans-esterification was carried out so
as to avoid a random microstructure and hence, PEAs with segmented microstructure could
be obtained. In the second step, polycondensation took place. Further, the amide content in
each series could be varied by taking different ratios of the preformed monomer to 1,4-

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