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Objectives
Background
Nomenclature
Theory
Nylon 6,10 Experimental
Pre-lab Quiz
Nylon 6 Experimental
Extension topics
Safety considerations
Notes
References
Self-test
Goals
The primary goal of this exercise is to teach you the student the
fundamental laboratory skills necessary for making nylons.
That's right, YOU are going to be able to make nylon when we're
through here. In addition, this exercise seeks to teach you the
fundamental concepts and theories involved with nylon synthesis.
We're going to do this so that you know just WHY you're doing
what you're doing, and not just following instructions like little
obedient sheep. Furthermore, by the time you're done we hope
that by having a firm grasp of the theory behind nylon synthesis,
and having mastered the hands-on skills involved, you'll know
how to alter the properties of your nylon by altering the
appropriate reaction conditions, plus be able to troubleshoot your
reaction should things go awry, all without having to go running
to your TA to ask what to do at every little step. You're here to
learn how to be independent, not codependent!
Objectives
The objectives to be reached in achieving the above stated goals
fall into two categories. First are the lab skills to be obtained, and
second are fundamental concepts to be learned. Let's list them:
Lab skills you will learn, if you don't already know them
Weighing out quantities of reactants
Preparing of solutions of known concentrations
Using a Bunsen burner without burning yourself and
without producing deadly amounts of carbon monoxide
The proper technique for heating a test tube in a flame
without shooting the contents at your lab partner
Safe handling of pyrophobic materials such as NaH
Drawing fibers from a molten polymer without burning
yourself
The Nylon Rope Trick, a neat visual demonstration
Concepts to be learned, if you don't already know them
The structure of nylons
The different kinds of nylon and how they differ
The monomers from which nylons are produced
The reactions by which nylons are produced
Which reaction variables affect the properties of the
product (e.g., molecular weight, tensile strength) and how.
What features of nylons make them good fibers
Background
Commercial Importance
Nylons are some of the most important fibers produced
commercially. If you've ever slept in a tent or used a toothbrush,
you've used nylon fibers. But nylon can be more than just fibers.
It's also used for self-lubricating gears and bearings. Nylon-clay
composites are used to make under-hood automobile parts.
The two most important kinds of nylon are nylon 6,6 and nylon 6.
These two nylons have almost identical properties. Both were
invented in the late 1930s. Nylon 6,6 was discovered first. It was
invented in the United States by Wallace Carothers who was
working for DuPont.10 Not long after that Nylon 6 was invented in
Germany by Paul Schlack who was working for I.G. Farben. 11
Physical Properties
You may ask yourself, "Why does nylon act as it does?" You may
ask yourself, "Why does nylon make such good fibers?" The
answer to both is pretty simple: intermolecular forces. Just for
review, Table 1 lists the different kinds of intermolecular forces.
When we're talking about nylons, the most important
intermolecular force is hydrogen bonding. The nitrogen-bonded
hydrogens of one nylon chain will hydrogen bond very strongly
with the carbonyl oxygens of another nylon chain. These
hydrogen bonds make crystals of nylon very strong, because they
hold the nylon chains together very tightly. Of course, these
strong crystals make strong fibers.
Unless it has been drawn into fibers, only about 20-30% of the
nylon in a given sample is crystalline when in solid form. The rest
is in the amorphous phase. But even though it's non-crystalline,
the chains are still bound strongly to each other by hydrogen
bonds. This combination of crystalline and strongly associated
amorphous phases is what makes nylon thermoplastics so tough.
(This onlyapplies to nylons used as thermoplastics, mind you.
When drawn into fibers nylons become almost entirely
crystalline.
Nylon Nomenclature
There are several systems for naming nylons. There is the
traditional system, the monomer system, and some newer
systems, like the IUPAC method, which is the method Chemical
Abstracts uses.2
Theory
Step-growth Polymerizations and Chain-growth Polymerizations
All polymerizations fall into two categories: step-growth
polymerizations and chain-growth polymerizations. Both stepgrowth polymerizations and chain-growth polymerizations are
used to make nylons. Making nylon from a diacid and a diamine
is a step-growth polymerization. So is making nylon from an
amino acid. Making nylon from lactams is usually a chain-growth
polymerization.
So what is the difference between the two types of
polymerization? That would take a long time to explain, so if you
want to know, go read the Macrogalleria page called Putting Them
Together. But there are some practical differences you should
know about for this experiment...
In a step-growth system, we start off with monomers. The
monomers combine and grow into dimers, trimers, tetramers,
and so forth. The molecules get bigger and bigger, but only when
Take a look at the above two reactions. Because the first one uses
two different types of monomers, one which has two amine
groups and one with two acid group, we call this an AA-BB
system. Think of the amine groups as A's and the acid groups as
B's, and you can figure out why. Likewise, the second reaction,
the one using the amino acid, is called an AB system. This is
obviously because the monomer contains both an amine group
(A) and an acid group (B) in the same molecule.
AB systems have an advantage over AA-BB systems. The
advantage is that in an AB system, one always has the same
amount amine groups and acid groups. As we all know,
stoichiometric balance of amine and acid groups is absolutely
critical when making nylons. With AA-BB systems, the amounts
of the two monomers must be measured very carefully to ensure
perfect stoichiometric balance.
Interfacial Polymerizations
Making nylon 6,6 is even easier if you use a diamine and a diacid
chloride instead of a diacid. This is because acid chlorides are
much more reactive than acids. The reaction is done in a twophase system. The amine is dissolved in water, and the diacid
chloride in an organic solvent. The two solutions are placed in the
same beaker. Of course, the two solutions are immiscible, so there
will be two phases in the beaker. At the interface of the two
phases, the diacid chloride and diamine can meet each other, and
will polymerize there. There is special way to do this called the
"Nylon Rope Trick"4, and we'll show you how to do that in just a
minute.
While this is a neat party trick, it isn't used commercially
because, first, acid chlorides are a lot more expensive than acids,
and second, acid chlorides stink horribly, and are much more
toxic than acids. And third, the fibers produced by this trick
aren't very strong, anyway.
Ring-Opening Polymerization
The ring opening-polymerization of lactams is a chain-growth
polymerization. It is also a polyaddition reaction, that is, no
Order of Polymerizability
(ring sizes)
7>5>6
7 > 8 > 9 >> 5 > 6
8 > 7 > 11 > 5 > 6
Now the leftover sodium cation can form a salt with the
negatively charged nitrogen that is left behind when the hydrogen
is extracted. But we don't want that. We want the nitrogen to be a
This step is faster than the that first ring opening step, the one in
Figure 3, because the starting species involved this time is much
more reactive. You see, the reacting compound this time is
an imide, a compound with a nitrogen atom bonded
to two carbonyl carbons. The last time we were reacting an amide,
which is a compound with a nitrogen bonded to only one carbonyl
carbon. Imides are much more reactive than amides.
Part of the reason why imides are more reactive than amides is
the fact that when an imide ring-opens we get an amide anion,
whereas the product of an amide ring-opening is an amineanion.
Amine anions are very unstable, but amide anions are more
stable because the negative charge is stabilized by the carbonyl
group bonded to the nitrogen atom.
This reaction won't work well without poly(ethylene oxide) or Nacetylcaprolactam. But add both of them and you can get high
molecular weight nylon 6 after heating the mixture for 2-3
minutes. Just don't heat it longer, because your polymer will
thermally degrade. The molecular weight will drop, and then you
won't be able to draw good fibers from your polymer. Your fibers
will be hard to draw and they will also be brittle, so don't let it
cook for too long!
Nylon 6,10 Experimental
Materials:
hexamethylene diamine (1g)
sebacoyl chloride (1g)
hexane (25ml)
two 100 ml beakers
glass stirring rod
balance
Procedure:
1. Dissolve about 1 g of hexamethylene diamine in 25 ml of water
in a 100 ml beaker.
2. Make solution of about 1 g of sebacoyl chloride in 25 ml
hexane.
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Nylon 6,6 is a polyamide fiber synthesized by combining adipic acid with hexamethylene diamine.
The 6,6 notation indicates that both reactants donate six carbons each to the polymer they form,
unlike nylon 6, which is produced through a different process. Nylon 6,6 is one of the most versatile
man-made fibers and finds a host of applications -- everything from carpet material to parachute
cords. Its distinctive physical properties are responsible for its success.
Uses of Nylon 6
1.
o
Structure
In nylon 6,6, there are six carbons intervening between two amide groups. (An amide
group involves an oxygen double-bonded to a carbon directly next to a nitrogen bonded to a hydrogen
and another carbon.) Nitrogen and oxygen are both very electronegative elements, meaning they are
"selfish" when sharing electrons with another atom and the electrons tend to spend more time around
the nitrogen/oxygen atoms. Consequently, hydrogen bonds form where the partially positivelycharged hydrogen atom bonded to a nitrogen interacts with the oxygen atom in an amide group on a
neighboring chain. This feature accounts for many of nylon 6,6's remarkable properties.
One of nylon 6,6's most valuable properties is its high tensile strength -- greater than
that of wool, silk or cotton. Its strength derives from hydrogen bonds between neighboring chains,
which enable the nylon to form tough, durable fibers that hold together under stress. The specific
gravity of nylon 6,6 ranges from 1.02 grams per cubic centimeter to 1.49 grams per cubic centimeter,
depending on its amount of crystallinity -- which in turn depends on how it is formed.
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Nylon 6,6's heat capacity -- the amount of heat energy needed to raise its temperature
by 1 degree Celsius -- is 1.67 joules per grams Celsius, only about 40 percent of the heat capacity of
water. Its thermal conductivity (the rate at which it conducts heat) ranges from 0.200 to 0.290 watts
per meter Kelvins; although this value is much higher than many insulating materials, it is lower than
glass and far lower than good conductors like metals. Nylon 6,6 is also a poor conductor of electricity.
Other Properties
o
Polyamide nylon 6
Engineering Polyamide nylon 6 Supply,
Modified Granules,Flame Retardant.
www.ShunYanplas.com/PA
Annealing Ovens
Despatch ovens and furnaces
for annealing metals and plastics
www.despatch.com
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