Attachment 1
1.5-Naphthalene Diisocvanate (NDI) vs. 1.6-Hexamethvlene Diisocvanate (HDD
The two polyurethane raw materials 1,5-naphthalene diisocyanate (NDI) and
1,6-hexamethylene diisocyanate (HDI) are both chemically classified as
organic diisocyanates and both undergo reactions typical of this highly
reactive group of compounds, but it is only in these aspects where
similarities exist. The physical properties of the two monomeric
polyurethane building blocks, the application areas in which they are used,
and most characteristics of the final polyurethanes obtained are
significantly different. Many of the differences are documented in a book
entitled "Polyurethane Handbook" which was edited by Guenter Oertel,
published by Hanser Publishers of Munich in 1985, and is distributed in the
USA by Macmillan Publishing Co., Inc. located at 866 Third Avenue on New
York, N.Y. 10022, and in references cited therein.
The physical properties of the two materials are considerably different, an
.attribute which is dependent on not only the wide gap between the molecular
weight of the two pure compounds, but also the chemical structure
classifications of the two compounds. NDI has a significantly higher
molecular weight of 210 compared with 168 for HDI. NDI has aromatic rings in
its structure, whereas HDI is a linear molecule. These two features cause
NDI to be a relatively high melting solid (m.p. 127°C or 260°F) with a
relatively low concentration of saturated vapor in air (0.16 mg/m3 at 50°C)
while HDI is a low viscosity liquid at room temperature and has a relatively
high concentration of saturated vapor in air (47.7 mg/m3 at 20 - C). The
differences in the vapor pressure and thus toxicitv are so dramatic that the
compounds are even classified differently for transport as well as for
handling: NDI is classified as "harmful to health" and the guidelines for
^transport are not as stringent as those for HDI which is classified as
'toxic." These differences in physical properties of the two materials lead
to differences in the way they are used, as well as differences in
application areas where the diisocyanates are used and the characteristics of
the final polyurethanes obtained.
NDI is a highly reactive compound and is used almost exclusively as a monomer
for the production of high quality elastomeric materials. It is sold into
the market in the form of the monomer without any modification. It is
typically combined with polyesters and a chain extender (usually 1,4-butane
diol) in a hot cure polyurethane casting system. It forms elastomers with
excellent tear resistance and low temperature performance properties but it
has relatively poor weathering resistance. Due to the presence of aromatic
rings in the monomeric compound, materials based on NDI have a tendency to
yellow on exposure to sunlight.
HDI is less reactive than NDI and is used almost exclusively in the form of
adducts (i.e., not in the monomeric form) for the production of high quality
coatings. HDI monomer is chemically modified in order to form less toxic
coating raw materials prior to entering the marketplace. It is typically
spray applied after combining it with polyester or acrylic polyols in two
-component coatings systems. It forms relatively hard, yet flexible coatings,
which have good low temperature performance properties. The coatings have
~*excellent weathering resistance.
The low temperature performance properties of polyurethanes in general are
excellent. However, materials based on HDI have rather significantly lower
softening points than those based on NDI; therefore, the higher temperature
erformance properties of the NDI-based polymers is better. The major
differences in the characteristics of the final polyurethanes obtained is the
light stability of the HDI-based materials vs. the superior properties of NDI
in the preparation of polyurethane elastomers.
Most chemists would agree that one cannot make valid comparisons between
compounds with such structural dissimilarities. It is like comparing apples
and oranges.
