GoalsNylon 6 Experimental
ObjectivesExtension topics
BackgroundSafety considerations
NomenclatureNotes
TheoryReferences
Nylon 6,10 ExperimentalSelf-test
Pre-lab Quiz
For background information, visit these
fun-filledMacrogalleriapages:NylonsMaking Nylon 6,6Making Nylon
6GoalsThe 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!ObjectivesThe 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 themWeighing out quantities
of reactantsPreparing of solutions of known concentrationsUsing a
Bunsen burner without burning yourself and without producing deadly
amounts of carbon monoxideThe proper technique for heating a test
tube in a flame without shooting the contents at your lab
partnerSafe handling of pyrophobic materials such as NaHDrawing
fibers from a molten polymer without burning yourselfThe Nylon Rope
Trick, a neat visual demonstrationConcepts to be learned, if you
don't already know themThe structure of nylonsThe different kinds
of nylon and how they differThe monomers from which nylons are
producedThe reactions by which nylons are producedWhich reaction
variables affect the properties of the product (e.g., molecular
weight, tensile strength) and how.What features of nylons make them
good fibersBackgroundCommercial ImportanceNylons 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.10Not long after that Nylon 6
was invented in Germany by Paul Schlack who was working for I.G.
Farben.11Physical PropertiesYou 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.
We all know that a lot of the nylon produced ends up as
clothing. But it also ends up as other everyday things like rope,
tents, and toothbrush bristles. Sometimes nylon is used to make the
belts that reinforce tires. Most passenger car tires have steel
belts, but tires for aircraft, trucks and off-road vehicles are
often made of nylon. Under the hood of your car you'll find nylon
fibers reinforcing rubber belts, too.Table 1
Nylon NomenclatureThere 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.2In the traditional system, the name includes the
word "nylon" followed by either one number or two numbers. If the
nylon is made from an A-B monomer there will only be one number.
But if there are two numbers, then you know that the nylon was made
from an A-A/B-B monomer system. For nylons made from A-B monomers,
the number tells you how many carbon atoms are in the monomer,
which of course is also the number of carbon atoms in the repeat
unit of the nylon. Hence, if a nylon is named "nylon 6", you know
that it is made from an A-B monomer, and that A-B monomer has six
carbon atoms. For nylons made from A-A/B-B monomer systems, the two
numbers tell you how many carbon atoms are in the diamine monomer,
and how many carbons are in the diacid or diacid chloride monomer.
For example, if your nylon is called "nylon 6,10", you know that it
is made from an A-A/B-B monomers system, you know that the diamine
from which it was made has six carbons, and that the diacid or
diacid chloride from which it was made has ten carbon atoms.The
monomer system, also calledsource basednomenclature, is not used
very often. It is confusing because different monomers can be used
to make the same nylon. For example, you can polymerize-caprolactam
to get poly(-caprolactam), and you can polymerize aminohexanoic
acid to get poly(aminohexanoic acid). But in fact, you get the same
polymer each time: nylon 6. So don't waste a lot of time worrying
about this system. just know how to interpret its names so you
won't be confused if you ever come across them.Finally, there are
the structure-based names. The two main ones are the IUPAC and the
non-IUPAC systems. Both attempt to unambiguously describe the
repeat unit, but the non-IUPAC is much simpler.Take a look at Table
2 to see examples of all of these nomenclature systems.Table
2Naming Conventions for Alkyl Polyamides3
TheoryStep-growth Polymerizations and Chain-growth
PolymerizationsAll polymerizations fall into two categories:
step-growth polymerizations and chain-growth polymerizations. Both
step-growth 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 calledPutting 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 we're done (when the polymerization reaches high
conversion) do we have high molecular weight polymers.But in a
chain growth system, we start off with monomers, and the monomers
quickly form high molecular weight polymers. There are high
molecular weight polymers present in your test tube just after you
start the polymerization. What's more, you won't have dimers,
trimers, and other oligomers hanging around. A growing polymer
chain grows so fast that it reaches high molecular weight quickly,
and it doesn't spend any real length of time as an
oligomer.PolycondensationsPlease don't get confused, but there is
another way to describe polymerizations other than the
step-growth/chain-growth system. There is also the
condensation/addition system. To know more about this system, again
go visit the Macrogalleria pagePutting Them Together. The most
important thing you need to know about this system is that it
classifies all polymerizations as polycondensations or
polyadditions. Polycondensations are polymerizations in which a
small molecule by-product is produced. The by-product is usually
something like water, HCl, or once in awhile NaCl. Polyadditions on
the other hand are polymerizations in which no by-product is
produced.We're going to talk now about using polycondensations to
make nylons. The simplest polycondensation for making nylons is the
polymerization of a diacid and a diamine. This reaction might not
normally go to high conversions, but by removing the water
by-product (usually by carrying out the reaction under vacuum so
the water evaporates), we can force this reaction go to higher
conversions.
Removing water makes the reaction go to high conversion thanks
toLeChatlier's Principle. The self-condensation of an amino acid is
a simple modification of the above reaction. Again, this reaction
is forced to high conversion by removing the water formed with a
vacuum.
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 PolymerizationsMaking 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 two-phase 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 PolymerizationThe ring
opening-polymerization of lactams is a chain-growth polymerization.
It is also a polyaddition reaction, that is, no byproducts are
produced. The thermodynamic driving force for ring-opening
polymerizations is ring strain. Cyclic molecules polymerize in
order to relieve the strain. Take a look at Table 3, and you'll see
that 5- and 6-membered rings don't have very much ring strain, so
they don't polymerize well. But 7-membered rings, like-caprolactam,
are much more strained and polymerize easily. As you can see in
Table 3, so do many larger cyclic monomers.Table 3Polymerizability
of Lactams5Type ofOrder of Polymerizability
Polymerization(ring sizes)
anionic (strong base)7 > 5 > 6
hydrolytic (water initiated)7 > 8 > 9 >> 5 >
6
cationic8 > 7 > 11 > 5 > 6
There are two ways to carry out a ring-opening polymerization
of-caprolactam. Down at the nylon factory, nylon 6 is made using a
water-initiated process. Read about it on the Macrogalleria
pageMaking Nylon 6The second way to make nylon 6 is to use a strong
base as an initiator.6How strong a base? Very strong. A normal
strong base like NaOH isn't going to work here. We'll need an extra
strong base like sodium hydride (NaH). The hydride anion is an
incredibly strong base, and when it sees caprolactam, it runs
straight to the amide hydrogen and pulls it right off, as you can
see in Figure 1.Figure 1
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
free anion, because it will be more reactive that way. So we're
going to throw some poly(ethylene oxide) into the reaction mixture.
This will complex the sodium cation, keeping it from associating
with the anionic nitrogen. You can see this in Figure 2.Figure
2
So the nitrogen, free to react, will donate an unshared pair of
electrons to the carbonyl carbon of another caprolactam molecule.
(Remember, carbonyl carbons are electron deficient, and are easily
attacked by anions.) After some electron-shuffling in which the
electrons in the bond between the carbonyl carbon and the amide
nitrogen shift to the nitrogen, the second caprolactam molecule
ring-opens, as you can see in Figure 3.Figure 3
The new molecule formed also has a negatively-charged nitrogen,
an amine anion. This is an unstable species, so the activation
energy is high for this step. This makes this the slow step of the
reaction. For this reason, there is an induction period at the
beginning of the reaction before polymerization begins.Being
unstable, that anionic nitrogen will abstract a proton
fromanothermolecule of-caprolactam, as Figure 4 clearly
shows.Figure 4
We have an anion of-caprolactam once again, and the negatively
charged nitrogen attacks the ring carbonyl carbon of the species we
just formed. Take a look at Figure 5 and you'll see what's
happening.Figure 5
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
animide, a compound with a nitrogen atom bonded totwocarbonyl
carbons. The last time we were reacting anamide, 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 anamideanion, whereas
the product of an amide ring-opening is anamineanion. 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.
Of course, this gives us another unstable nitrogen negative
charge, and it takes a proton from another-caprolactam molecule,
which then adds to the growing chain in the same way as we saw
before. This keeps happening over and over until we get high
molecular weight nylon 6.Just one more thing...remember that the
first ring-opening step was so slow? We can get around this slow
step by throwing a little bit ofN-acetylcaprolactam into the
reaction mixture. Not only is this is a reactive imide, just like
the rings in our growing chain, but it produces an amide anion when
it ring-opens rather than an unstable amine anion. It takes the
place of-caprolactam in the first step, so the slow step is
eliminated, and so is that annoying induction period.
This reaction won't work well without poly(ethylene oxide)
orN-acetylcaprolactam. 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 ExperimentalMaterials:hexamethylene diamine
(1g)sebacoyl chloride (1g)hexane (25ml)two 100 ml beakersglass
stirring rodbalanceProcedure: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.3. Gently pour the
sebacoyl chlorie/hexane solution on top of the hexamethylene
diamine/water solution in the beaker, using a glass rod to pour
down. A film will form at the interface.4. Draw a thread out of
this interface using a glass rod, and draw the thread out of the
beaker. Using a second 100 ml beaker as a spool, slowly wind up the
thread as you draw it out.5. After all the polymer has been
collected, wash it thoroughly with water, dry it superficially with
a towel, then let it air dry.6. Unwind the dry thread and let the
students examine its physical properties. Rarely will this material
display any significant strength.Nylon 6
ExperimentalMaterials:disposable test tube, 18 x 150 mm or
largertest tube holderBunsen burnerdisposable Pasteur
pipettebalance-caprolactam (recrystalized from cyclohexane)sodium
hydride (NaH), 60% dispersion in oilpolyoxyethylene [also called
poly(ethylene glycol)]N-acetylcaprolactamProcedure:Weigh out the
following:caprolactam (10g)polyoxyethylene (POE) (molecular weight
= 2000-7500) (0.2 g)N-acetylcaprolactam (3-5 drops)1. Mix the above
in a test tube. Hold the tube with a test tube holder. (Don't hold
it with your hands; it's going to getHOT!)2. Light your Bunsen
burner and adjust the flame to about 1 inch. Heat the tube in the
flame, moving it around, passing it in and out of the flame. This
is to ensure even heating. Uneven heating can cause an explosion,
which would mean you'd lose your reactants when they shoot out of
the tube, and the hot reactants wil splatter all over your lab
partner causing severe burns.3. When the mixture in the tube melts,
add a spatula tip of NaH (move NaH from large contaner to smaller
vials to prevent the whole can of NaH from burning up). Make sure
all of your NaH reacts bycarefullytilting your test tube so that
any NaH stuck to the sides of the tube comes into contact with the
reaction mixture. Be careful not to spill the contents when you
tilt the tube!4. Keep heating the test tube for 2-4 more minutes.
Be careful to keep moving the tube to ensure even heating. If you
don't, you can get hot spots, which will boil. This will lead to
"bumping", which is when your reaction mixture shoots out of the
tube. The liquid is very hot (220-230oC) and will cause severe
burns.5. The reaction should be done about the time the reaction
mixture starts to reflux, or simmer. You will know it has
polymerized because the mixture will become much more viscous. If
polymerization does not occur within several minutes, cool to just
above the solidification temperature, add more NaH, and
reheat.Caution!Adding too much initiator or heating too long will
lead to low molecular weight and brittle fibers. Also, heating too
slowly allows the active species (the sodium salt of caprolactam)
to react with moisture in the air, andit will no longer be abel to
initiate polymerization.You may not get it right on the first try.
After several attempts, you will figure out just how much NaH to
add and how long to heat it (Note 3).The most exciting part of the
experiment involves pulling fibers from the molten polymer. The
polymer is ready when the viscous mass no longer bubbles freely and
barely flows at the polymerization temperature. Fibers are drawn by
dipping a glass rod into the polymer and rapidly drawing out the
solidifying material. It may be necessary to let the polymer cool
some to get just the right combination of viscosity and strength.
With two students working together and one of them walking down the
hallway trailing barely-visible fiber behind him, thin strands
75-100 feet long have been made with this method. These fibers will
stretch under tension to complete polymer orientation and are then
very tough. You should be able to make material similar to
commercial nylon thread or fishing line (Note 4).Extension
OptionsAs the ratio of NaH to monomer increases, the molecular
weight of the polymer decreases. The experiment can be extended by
having the same or different students use varying ratios of NaH to
caprolactam. The polymers synthesized can then be tested in one of
two ways. A rough test is based on the fact that as the molecular
weight of the polymer decreases, the fibers become weaker and
finally the polymer cannot be drawn into fibers at all. A more
quantitative approach is to make a capillary viscometer9,10. Either
method should show an inverse relationship between amount of NaH
used and the molecular weight of the polymer synthesized.Safety
ConsiderationsDo not point the test tubes at a fellow student when
heating it since heating too rapidly can cause splattering.The test
tube and the molten polymer are hot. Don't touch the test tube or
the fiber with their hands until they are cool.The NaH must be kept
away from water. Hydrolysis will generate hydrogen gas which will
burn or explode!Both caprolactam andN-acetylcaprolactam are
slightly toxic chemicals. Don't eat them (duh!) or touch them with
your hands.Wear safety goggles or glasses at all times.Notes1.
18-Crown-6 may be used instead of POE in the procedure. With the
crown ether, the reaction is even faster and the final polymer is
lighter in color. However, 18-crown-6 is expensive when compared to
the linear polyether. Also, poly(ethylene oxide) is very safe,
while crown ethers are toxic and easily absorbed through the
skin!2. Although weighing out the reactants is good practice, this
procedure is versatile enough to work even with rough estimates of
the reactant amounts.3. If repeated attempts at polymerization
fail, the caprolactam may be impure. Caprolactam may be
recrystallized from cyclohexane.84. The experiment can be made more
challenging for a by including the synthesis of caprolactam as the
first part of the experiment. Caprolactam can be synthesized be the
Beckman rearrangement of cyclohexanone oxime. An excellent lab
experiment for this synthesis has been reported8. Final
purification by recrystallization followed by polymerization makes
this a sequence of experiments representing the complete commercial
synthesis of nylon, and giving a product with excellent "hands-on"
properties.References1.a. B. F. Greek, Chem. Eng. News, May 30,
1983, p.14; b.Chem. Eng. News, April 18, 1983, p. 6.2. R. B. Fox,J.
Chem. Educ., 1974,51, 41 and 113.3. B. Odian,Principles of
Polymerization, 2nd edition, John Wiley & Sons, Publishers, New
York, 1981, p. 12.4. P. W. Morgan and S. L. Kwolek,J. Chem. Educ.,
1959,36, 1982.5. Ref. 3, p. 5426. H. R. Allcock and F. W.
Lampe,Contemporary Polymer Chemistry, Prentice-Hall, Inc. Englewood
Cliffs, N.J., 1981, pp. 128-129.7. B. Z. Shakhashiri,Chemical
Demonstrations, Vol. 1, University of Wisconsin Press, Madison,
Wisconsin, p. 213.8. Procedures and References cited in L. J.
Mathias,J. Chem. Educ., 1983,60, 990.9. E. Pearce, C. E. Wright and
B. K. Bordolo,Laboratory Experiments in Polymer Synthesis and
Characterization, Pennsylvania State University Press, University
Park, PA, 1982, pp. 133-152.10. Carrothers, W.H. (to E.I. DuPont de
Nemours and Co.), U.S. Patent 2,130,523 (1938).11. Schlack, P.,
German Patent 748,253 (1938), U.S. Patent 2,241,321
(1941).Self-Test1. Name five common uses for Nylons in general and
Nylon 6 in particular.2. Name the following polyamides with Nylon,
source and structure names.
3.Why would you expect the following two polyamides (aramids) to
have better thermal and mechanical properties than aliphatic
nylons?
4. Which of the above aramids would you expect to have better
properties? Why? (Hint: What is Kevlar and what is it used for?)5.
Why are nylon ropes better in many applications than cotton, jute,
and metal cables? (A good example is on boats, barges, and
ships.)
Return to USM Polymer Science Online Laboratory Directory
Copyright 1998|Department of Polymer Science|University of
Southern Mississippi
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Nylon 66The Physical Properties of Nylon 66By John Brennan, eHow
Contributor Print this articleMany ropes are made from nylon
6,6.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.Other People Are Reading How Is Nylon
Made? Uses of Nylon 61. 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
positively-charged 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.Strength and Density 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.
Sponsored Links Plastic mouldSpecialized in Plastic mould high
quality and competitive pricewww.Win-Industry.comHeat Capacity and
Conductivity 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 Nylon 6,6 is abrasion-resistant and resistant to attack
by many chemicals; it is easy to wash and can be dyed during
preparation, making it even more valuable for use in clothing and
accessories. Its melting point is 263 degrees Celsius. The melting
point for nylon 6,6 is much higher than the melting point for nylon
6, which is otherwise fairly similar to nylon 6,6 in terms of its
physical properties. The lower melting point of nylon 6 is a
disadvantage since garments made from nylon 6 poorly tolerate
ironing.Sponsored Links Get New Customers OnlineAdvertise On
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PropertiesReferences UT Knoxville College of Engineering: Nylon
Fibers MaterialsWeb: Overview of Materials for Nylon 66,
Unreinforced Engineering Toolbox: Thermal Conductivity of Some
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