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Nylon 6,6

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Nylons are some of the most important fibers produced commercially. A lot of the nylon produced ends up as clothing. But nylon can be more than just fibers. 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 reinforcement for tires for aircraft, trucks and off-road vehicles are often made of nylon. Nylon-clay composites are used to make under-hood automobile parts. Nylon is used for self-lubricating gears and bearings.

One of the most important kinds of nylon is nylon 6,6. It was invented in the late 1930s in the United States by Wallace Carothers who was working for DuPont. Nylon can be synthesized by polycondensation. Polycondensation is polymerization in which monomers combines and a small molecule by-product is produced. The by-product is usually something like water, HCl, or once in awhile NaCl. The simplest polycondensation for making nylons is the reaction of a diamine and a diacid: O O ║ ║
H2N-CH2-CH2-CH2-CH2-CH2-CH2-NH2 + HOC-CH2-CH2-CH2-CH2-COH ↔

This reaction might not normally go to high conversions: H O O │ ║ ║
↔ H2N-CH2-CH2-CH2-CH2-CH2-CH2-N-C-CH2-CH2-CH2-CH2-COH + H20

Removing water (usually by carrying out the reaction under vacuum and/or at elevated temperature so the water evaporates), makes the reaction go to high conversion thanks to LeChatlier's Principle:

H HO O H H O O H H O O │ │║ ║ │ │ ║ ║ │ │ ║ ║ -N-(CH2)6-N-C-(CH2)4-C-N-(CH2)6-N-C-(CH2)4-C-N-(CH2)6-N-C-(CH2)4-C- + H20

Because two different chemical were uses, one that has two amine groups and another that has two acid groups, the polymer can be represented by two different segments:

-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-

Making nylon 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"

It is possible to prepare a polymer from only one type of monomer that has an acid group at one side and an amino group at another side. Amino acid is an example of such monomer. The polycondensation of amino acids produces poly(amino acid) or, if natural amino acids used, proteins.

The name of the polymer includes the word "nylon" followed by either one number or two numbers. If the nylon is made from one type of monomer (like amino acid) there will only be one number. But if there are two numbers, then you know that the nylon was made from two types of monomer system. For nylons made from one type of monomer, the number tells you how many carbon atoms are in the monomer. Hence, if nylon is named "nylon 6", you know that it is made from a monomer that has six carbon atoms. For nylons made from two types of 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 6,6" 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 six carbon atoms.

Nylon 6,10 Experiment
Materials:
Hexamethylene diamine (1g)
Sebacoyl chloride (1g)
Hexane (25ml)
100 ml beaker
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.
3. Gently pour the sebacoyl chlorie in hexane solution on top of the hexamethylene diamine in 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 forceps, and draw the thread out of the beaker. Using a glass rod 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 dry.
6. Unwind the dry thread and let the students examine its physical properties. Rarely will this material display any significant strength.

Of course, the monomers are two small to see and even if they have different color you will not get a rope colored as it is shown on the picture.

Source: Department of Polymer Science, University of Southern Mississippi: http://pslc.ws/macrog/lab/lab01.htm

Nylons are some of the most important fibers produced commercially. A lot of the nylon produced ends up as clothing. But nylon can be more than just fibers. 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 reinforcement for tires for aircraft, trucks and off-road vehicles are often made of nylon. Nylon-clay composites are used to make under-hood automobile parts. Nylon is used for self-lubricating gears and bearings.

-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-A-B-…...

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