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Notes on Nylon 6: Ring Opening Polymerization | PSC 720, Exams of Chemistry

University of Southern Mississippi (USM)Chemistry

Material Type: Exam; Class: Polymer Techniques I; Subject: Polymer Science; University: University of Southern Mississippi; Term: Unknown 2009;

Typology: Exams

Pre 2010

Uploaded on 02/24/2010

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Drs. D.A.Savin, D.L. Patton Techniques PSC341L/720
Electronic Handout
©
2009 D. L. Patton
Nylon 6: Ring Opening Polymerization
Polyamides
Nylon is the term commonly used to describe aliphatic polyamides. Common aliphatic
polyamides such as Nylon 6, Nylon 6,6 and Nylon 6,10 exhibit high mechanical strength,
toughness, and chemical resistance, and can be drawn to form high-strength fibers. These
nylons are commonly used in fiber and textile applications as well as in injection molding
applications requiring chemical resistance and tight tolerance. Aromatic polyamides (or
aramids) form ultra-high strength, high temperature fibers1.
Kevlar® was developed at DuPont in 1965 by research scientists Stephanie L. Kwolek2,3
and Herbert Blades4,5. Kevlar® has a strength-to-weight ratio five times that of steel. In
addition to its high strength, Kevlar® exhibits properties useful for a wide range of high
performance applications, including excellent chemical resistance, wear and friction
resistance, dimensional stability, and flame retardancy. Applications include: personal
protection: bullet proof vests, body armor, cut-resistant gloves, thermal and cut-resistant
protective clothing, motorcycle apparel, and helmets; sports equipment: composites for
tennis rackets, hockey sticks, cast and spin rods, scuba dry suits, and kayaks; ropes and
cables: high strength ropes to moor Navy vessels and to secure Mars Pathfinder, fishing
line, fiber optic and electro-mechanical cables; and high performance tires: aircraft, off-
road, “run-flat” tires, and many more.
Nomex® fiber was also developed over thirty years ago by DuPont scientists6. Nomex®
exhibits excellent flame and thermal resistance, and is used in applications such as flame-
retardant racing apparel, firefighter protective clothing and industrial protective clothing;
insulating material for generators and transformers; flexible high-temperature hoses for
automotive under-the-hood applications; and lightweight honeycomb composite
structures used in aircraft and naval applications.
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Electronic Handout © 2009 D. L. Patton

Nylon 6: Ring Opening Polymerization

Polyamides

Nylon is the term commonly used to describe aliphatic polyamides. Common aliphatic polyamides such as Nylon 6, Nylon 6,6 and Nylon 6,10 exhibit high mechanical strength, toughness, and chemical resistance, and can be drawn to form high-strength fibers. These nylons are commonly used in fiber and textile applications as well as in injection molding applications requiring chemical resistance and tight tolerance. Aromatic polyamides (or aramids) form ultra-high strength, high temperature fibers^1.

Kevlar ® was developed at DuPont in 1965 by research scientists Stephanie L. Kwolek2, and Herbert Blades4,5^. Kevlar® has a strength-to-weight ratio five times that of steel. In addition to its high strength, Kevlar® exhibits properties useful for a wide range of high performance applications, including excellent chemical resistance, wear and friction resistance, dimensional stability, and flame retardancy. Applications include: personal protection: bullet proof vests, body armor, cut-resistant gloves, thermal and cut-resistant protective clothing, motorcycle apparel, and helmets; sports equipment: composites for tennis rackets, hockey sticks, cast and spin rods, scuba dry suits, and kayaks; ropes and cables: high strength ropes to moor Navy vessels and to secure Mars Pathfinder, fishing line, fiber optic and electro-mechanical cables; and high performance tires: aircraft, off- road, “run-flat” tires, and many more.

Nomex® fiber was also developed over thirty years ago by DuPont scientists 6. Nomex® exhibits excellent flame and thermal resistance, and is used in applications such as flame- retardant racing apparel, firefighter protective clothing and industrial protective clothing; insulating material for generators and transformers; flexible high-temperature hoses for automotive under-the-hood applications; and lightweight honeycomb composite structures used in aircraft and naval applications.

Electronic Handout © 2009 D. L. Patton

Ring Opening Polymerization

Polymerizations may be classified as condensation, vinyl, or ring opening polymerizations. Ring opening polymerizations differ from the other types in that there is no elimination of a small molecule, as in condensation, and there is no loss of multiple- bonding enthalpy, as in vinyl polymerization. Ring opening polymerization is the primary commercial route to produce inorganic polymers^7.

Cyclic amides (or lactams ) may be polymerized to form nylons.

The polymerization may be initiated by base, acid or water, but water initiator is most commonly used industrially^8. Typically ε-caprolactam (6-hexanolactam) is polymerized at 250-270°C with 5 – 10% water. After hydrolysis of the lactam to the amino acid:

polymerization can occur by step polymerization of the amino acid with itself, or by ring- opening polymerization by attack of the amine nitrogen on the lactam. Ring opening polymerization is the primary route for polymerization.

n CO – NH – (CH 2 )m Æ [ NH – (CH 2 )m – CO ]n

CO – NH – (CH 2 ) 5 + H 2 O Æ HO 2 C(CH 2 ) 5 NH 2

nHO 2 C(CH 2 ) 5 NH 2 [ NH – (CH 2 ) 5 – CO ] (^) n + H 2 O

HO 2 C(CH 2 ) 5 NH 2 + CO – NH – (CH 2 ) 5 HO 2 C(CH) 5 NHCO(CH 2 ) 5 NH 2