Nylon 12 is a

nylon polymer Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from petro ...

with the formula CH₂)₁₁C(O)NHsub>n. It is made from ω-aminolauric acid or

laurolactam Laurolactam is an organic compound from the group of macrocyclic lactams. Laurolactam is mainly used as a monomer in engineering plastics, such as nylon-12 and copolyamides.T. Schiffer, G. Oenbrink: ''Cyclododecanol, Cyclododecanone, and Laurolacta ...

monomers that each have 12 carbons, hence the name ‘Nylon 12’. It is one of several

nylon Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from pet ...

polymers.

Synthesis

Nylon 12 can be produced through two routes. The first being

polycondensation In polymer chemistry, condensation polymers are any kind of polymers whose process of polymerization involves a condensation reaction (i.e. a small molecule, such as water or methanol, is produced as a byproduct). Condensation polymers are for ...

of ω-aminolauric acid, a bifunctional

monomer In chemistry, a monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification ...

with one

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

and one

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...

group. n H₂N(CH₂)₁₁CO₂H → CH₂)₁₁CONHsub>n + n H₂O The second route is

ring-opening polymerization In polymer chemistry, ring-opening polymerization (ROP) is a form of chain-growth polymerization, in which the terminus of a polymer chain attacks cyclic monomers to form a longer polymer (see figure). The reactive center can be radical, anio ...

at 260-300˚C. Ring opening can be carried out by cationic or anionic initiators, although cationic initiators have not been used commercially due to the product being less stable and

oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

relatively quickly in comparison to those produced by activated anionic polymerization (monomer casting). Ring-opening polymerization is the preferred route for commercial production. :n CH₂)₁₁CONH → CH₂)₁₁CONHsub>n

Properties

Nylon 12 exhibits properties between short chain aliphatic nylons (e.g.,

nylon 6 Nylon 6 or polycaprolactam is a polymer, in particular semicrystalline polyamide. Unlike most other nylons, nylon 6 is not a condensation polymer, but instead is formed by ring-opening polymerization; this makes it a special case in the compari ...

and

nylon 66 Nylon 66 (loosely written nylon 6-6, nylon 6/6, nylon 6,6, or nylon 6:6) is a type of polyamide or nylon. It, and nylon 6, are the two most common for textile and plastic industries. Nylon 66 is made of two monomers each containing 6 carbon atoms, ...

) and

polyolefin A polyolefin is a type of polymer with the general formula (CH2CHR)n where R is an alkyl group. They are usually derived from a small set of simple olefins (alkenes). Dominant in a commercial sense are polyethylene and polypropylene. More speciali ...

s. At 178-180 °C, the melting point of nylon 12 is the lowest among the important

polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made th ...

s. Its mechanical properties, such as hardness, tensile strength, and resistance to abrasion, are similar to those of nylon 6 and nylon 66. Low water absorption and density, 1.01 g/mL, result from its relatively long hydrocarbon chain length, which also confers it dimensional stability and an almost paraffin-like structure. Nylon 12 is also chemical resistant and insensitive to stress cracking.

Applications

Nylon 12 has a broad range of applications as polyamide additives. Nylon 12 is mainly used for films for packing material in the food industry and sterilized films and bags for use in the pharmaceutical and medical fields. When added to

polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including b ...

films, it improves water vapor permeability and aroma impermeability. It is also prepared as sheets and sintered powder for coating metals. In the electronics field, it is used for covering cables and insulating material, while in the automobile industry it is used to prepare oil and gasoline resistant tubes. In the cosmetic and personal care industries, it is used as bulking and opacifying agents in the face and body powders, and skin creams.{{cite web, title=Regenerist Micro-Sculpting Cream Moisturizer, url=http://www.olay.com/en-us/skin-care-products/regenerist-micro-sculpting-cream-moisturizer, website=Olay, publisher=

Procter & Gamble The Procter & Gamble Company (P&G) is an American multinational consumer goods corporation headquartered in Cincinnati, Ohio, founded in 1837 by William Procter and James Gamble. It specializes in a wide range of personal health/consumer he ...

, accessdate=10 December 2015 Nylon 12 has also found uses in the textile industry and for producing sporting and leisure goods among other applications.

Manufacturers

Significant suppliers of nylon 12 include EMS-Chemie, the

Marl Chemical Park Marl Chemical Park (german: Chemiepark Marl) is an industrial park in Marl, North Rhine-Westphalia, Germany. It is the third largest industrial cluster in Germany and among the largest chemical production facilities in Europe. The site occupie ...

operated by

Evonik Evonik Industries AG is a stock-listed German specialty chemicals company headquartered in Essen, North Rhine-Westphalia, Germany. It is the second largest chemicals company in Germany, and one of the largest specialty chemicals companies in the ...

Arkema Arkema S.A. is a publicly listed, multi-national manufacturer of specialty materials, headquartered in Colombes, near Paris, France. It has three specialty materials segments (or divisions); adhesives, advanced materials and coatings. A furt ...

and SH Energy & Chemical

References

Polyamides