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GPEC 2008 Student Poster Abstract #8
Title: New Polyacetal Polyols for Polyurethanes
Authors: Mihail Ionescu, Semonti Sinharoy and Zoran S. Petrovic, Pittsburg State University,
Kansas Polymer Research Center
ABSTRACT
The synthesis of new polyacetal polyols as new polyhydroxyl intermediates for elastic
polyurethanes was investigated. The synthesized polyacetal polyols are telechelic polymers with
terminal hydroxyl groups either as diols or triols of molecular weight 3000-5000. They were
obtained by the reaction of glycols with divinyl ethers in the presence of acid catalysts. New
polyols have the following general structure (Figure 1) where X is a starter molecule (diol or
triol), m = functionality and n = polycondensation degree:
CH3 CH3
X O C O R O C O R OH
H H
n m
Figure 1: General structure of polyacetal polyols
The polyacetal polyols are colorless viscous liquids. They were characterized by FT-IR, 1H and
13
C NMR, Gel Permeation Chromatography, DSC and by determination of hydroxyl number,
viscosity and acid numbers. The polyacetal polyols were transformed successfully to cast
polyurethanes by the reaction with an aromatic isocyanate, MONDUR CD (Bayer). The resulting
elastomeric cast polyurethanes were characterized by determination of glass transition
temperature (Tg), tensile strength, elongation, hardness, swelling properties and soluble fraction
in toluene as solvent. The polyacetals are well known nontoxic, bio-compatible and
biodegradable polymers
The cast polyurethanes obtained had characteristics comparable with the polyurethanes based on
conventional polyether triols, copolymers propylene oxide-ethylene oxide. The polyacetal
polyols are suitable for the synthesis of elastic polyurethanes (polyurethane elastomers, flexible
polyurethane foams. The polyacetals are well known non-toxic, biocompatible and
biodegradable polymers. It is interesting to study the biodegradability of the polyurethanes based
on polyacetal polyols which it is expected to be new biodegradable polymers
NEW POLYACETAL POLYOLS FOR
POLYURETHANES
Semonti Sinharoy, Mihail Ionescu, and Zoran S. Petrović
Pittsburg State University, Kansas Polymer Research Center
Department of Chemistry and Plastics Engineering technology
Steps of synthesis The characteristics of synthesized polyacetal polyols
Abstract Synthesis and structure of polyacetaldiols
•In a stainless steel 450 mL Parr reactor was charged
The synthesis of new polyacetal polyols as new
with 13.6 g of TMP (0.1 mols), 171g of TEGDVE (0.85
polyhydroxyl intermediates for elastic O O CH2 + HO OH H
+
HO OH +
O mols), 115 g of DPG (0.85 mols) and 0.6 g of solid
polyurethanes was investigated. The synthesized O
n
H2C O O n
CH3 CH3 CH3 CH3 oxalic acid
polyacetal polyols are telechelic polymers with
terminal hydroxyl groups either as diols or triols of CH3
•The reactor was purged with nitrogen and an inert
molecular weight 3000-5000. They were obtained O O O O H
HO O O O O atmosphere was created with the pressure of nitrogen
by the reaction of glycols with divinyl ethers in the O
CH3 CH3
CH3 CH3 CH3 n being maintained in p.s.i.
presence of acid catalysts. The polyacetal polyols
are colorless viscous liquids. The polyacetal
•The reactor was heated at 80oC, under continuous
polyols were transformed successfully to cast Synthesis in Parr reactor
stirring and maintained at this temperature around 6
polyurethanes by the reaction with an aromatic
hours.
isocyanate, MONDUR CD (Bayer). The cast
polyurethanes obtained had characteristics Conclusion
•A colorless low viscosity polyacetal triol of molecular • A facile synthesis of polyacetal polyols,
comparable with the polyurethanes based on
weight of around MW=3000 was obtained. suitable for polyurethane production, by
conventional polyether triols.
polyaddition reaction of divinyl ethers
• The catalyst was neutralized by the addition of a and diols, initiated by trimethylol
General structure of polyacetal polyol tertiary amine in a molar ratio of 1:1 tertiary nitrogen propane or dipropylene glycol has been
studied.
per one carboxyl group.
• The synthesized polyols, of molecular
weight of 2000-6000, lead by the
R' •Higher molecular weight polyacetal polyols are reaction with aromatic isocyanates to
obtained at a higher ratio of (TEGDVE+DPG)/TMP. cast polyurethanes with characteristics
HO R O CH O R OH
comparable with the polyurethanes
n based on conventional polyether
Characteristics of PU cast elastomers based on polyacetal polyols.
polyols and the isocyanate MONDUR CD (Bayer) • The polyacetal polyols are suitable for
Synthesis of the polyacetal triols the synthesis of elastic polyurethanes.
Polyol Type Tensile Elongation, Hardness Swelling • The polyacetals are well known non-
O O
+
CH2 nHO OH toxic, biocompatible and biodegradable
OH H2C O O O used strength % (Shore A) ratio (in
+
n Starting compounds polymers. It is interesting to study the
CH3 CH3 + , MPa toluene) biodegradability of the polyurethanes
H CH2OH
O O CH2 + nHO OH
based on polyacetal polyols which it is
H3C + H2C O O O
OH H 3C C CH2OH
n CH3 CH3 CH2 PA-PUR-1 Polyacetal 1.010 122 40 2.6 expected to be new biodegradable
O O
+
CH2 nHO OH triol polymers.
O O O CH2OH
OH + H2C PA-PUR-2 Polyacetal 0.850 194 26 3.75
n CH3 CH3 triol
TMP
PA-PUR-3** Polyacetal 8.930 82 34 1.40
diol (Shore D) Acknowledgement
CH3 CH3 Arcol-F-3022* Polyether 0.888 37 46 3.23
CH3
HO CH CH2 O CH2 CH OH triol
O O O O H GPEC for the opportunity to present a poster
O O O O
CH3 CH3 CH3 n
CH3
DPG
O O O
O
O H+ Dr. Zoran Petrovic and Dr. Mihail Ionescu from
H3C O O O
CH3 CH3
Kansas Polymer Research Center
CH3 CH3 n
CH3 CH3
O O O O H
O O O O HO CH CH2 O CH2 CH OH An FT-IR spectrum of polyacetal
Mrs. Rebecca Book for helping and encouraging
H3C CH3 CH3 n triol
Based on TMP, TEGDVE and DPG Mike Thurman, my friend and classmate for travel
DPG arrangements
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