The synthesis of a new class of high-barrier polymers,
poly(hydroxy amide ethers), is
described. The polymers are formed by the reactions of bisphenol-A
diglycidyl ether,
OCH2CHCH2OC6H4C(CH3)2C6H4OCH2CHCH2O,
and amide-containing bisphenols of the general formula
HOC6H4NHC(O)RC(O)NHC6H4OH [R
= −(CH2)
n
−,
−CH2C6H4CH2−,
or −C6H4−] or
HOC6H4NHC(O)C6H4OH
at
140−160 °C in propylene glycol monophenyl ether solvent using
ethyltriphenylphosphonium acetate as
initiator. High-molecular-weight poly(hydroxy amide ethers)
of the general structure
[−CH2CH(OH)CH2OC6H4C(CH3)2C6H4OCH2CH(OH)CH2OC6H4NHC(O)RC(O)NHC6H4O−]
n
or
[−CH2CH(OH)CH2OC6H4C(CH3)2C6H4OCH2CH(OH)CH2OC6H4NHC(O)C6H4O−]
n
are readily prepared. The amorphous thermoplastics have glass transition temperatures
(T
g) of 90−133 °C and oxygen transmission
rates (O2TR)
which range from 0.7 to 4.6 cc·mil/100
in.2·atm·day (barrier units or BU) at 23 °C
and 47−85% relative
humidity. The effect that polymer structure has on oxygen barrier
properties and T
g is described.
The
characterization, structure determination, and properties of the
poly(hydroxy amide ethers), as well as
the amide-containing bisphenol precursors, are also
presented.
The synthesis of a series of new high-barrier poly(hydroxy
amide ethers) is described. The
polymers are formed by the reactions of Bisphenol A diglycidyl
with a series of
N,N‘-alkylenebis(4-hydroxybenzamides) of
general formula HOC6H4CONHRNHCOC6H4OH [R =
−(CH2)2
-
6−,
−CH2CH(OH)CH2−,
−CH2C6H4CH2−,
or −C6H4−] at 140−160 °C in propylene glycol monophenyl ether solvent using
ethyltriphenylphosphonium acetate as initiator.
Poly(hydroxy amide ethers) of general structure
[−CH2CH(OH)CH2OC6H4C(CH3)2C6H4OCH2CH(OH)CH2OC6H4CONHRNHCOC6H4O−]
n
are readily prepared in high molecular weight. These
amorphous
thermoplastics have glass transition temperatures
(T
g) of 110−152 °C and oxygen transmission
rates
(O2TR) which range from 1.0 to 2.8 cc·mil/(100
in.·atm·day) (barrier units or BU) at 23 °C and
58−86%
relative humidity. The effect that polymer structure has on
O2TR and T
g is discussed. Of
special interest
is the poly(hydroxy amide ether) in which R =
m-C6H4−. This polymer combines a
good oxygen barrier
(1.5 BU) with the T
g of an engineering
thermoplastic (152 °C).
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