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A Review On Naylon - 6

Pambhar Yash C.
Shree M.&N. Virani Science College
(Autonomous) - Rajkot

ABSTRACT

Nylon is one of the synthetic polymers which have large applications in environment. It is found to be a hard
plastic for degradation. Present study has examined the feasibility of a fungus, Trametes versicolor NCIM 1086
for actively degrading synthetic polymer Nylon 6. The analysis was carried out using I. R. spectroscopy and
mechanical techniques. Nylon sheets were inserted in fermentation broth which was incubated on a rotary
o
shaker at 30 C and 90 rpm for 90 days. Nylon 6 was the sole source of nitrogen in the medium. A colony of
fungus was developed that resulted in substantial degradation of Nylon 6. Weakening and breaking of
polyamide bond have been confirmed by weakening in I. R. band. The degradation led to formation of new
functional groups CH3, CHO and COOH.

Keywords: Trametes versicolor, Biodegradation, Nylon 6, Plastic waste management.

Introduction

Plastic is the most versatile synthetic manmade substance, created out of the fossil fuel resources. Plastic offer a
number of advantages over alternative materials – they are lightweight, low cost, extremely durable and
relatively unbreakable. Plastics are composed of petroleum based materials called resins (e.g., polythene and
polypropylene) – materials that are resistant to biodegradation. Discarded plastics, besides being highly visible
are a rapidly increasing percentage of solid waste in landfills, resistant to biodegradation leading to pollution,
harmful to the natural environment. In recent years there has been growing public concern over environmental
deterioration associated with the disposal of conventional plastics. (Kumar S. et. al., 2007).

Research on degradable synthetic polymers begins in the early 1980’s. The recognized lack of biodegradability
of large volume of commercial polymers, particularly commodity plastics used in packaging (e.g. fast food),
industry and agriculture, focused public attention on a potentially huge environmental accumulation and
pollution problem that could persist for centuries.(Yüksel et.al.,2004). Biodegradation is therefore considered as
a subset of degradation, which is defined here as any physical or chemical change in a material caused by any
environmental factor, including light, heat, moisture, wind, chemical conditions or biological activity. Polymers
bearing recurring amide groups in their backbone are defined as polyamides. Polyamide types of polymer have
been considered as a long standing existence. Therefore find, diversifies applications by all commodities. Nylon
6, one of the polyamide polymers finds its application in the bristles, ropes, fabrics, fishing nets, automobile
parts etc.

Figure 1: Formation of nylon 6 from ε caprolactam


Nylon 6 is a polymer obtained by ring – opening polymerization of ε caprolactam and has several commercial
names including perlon, nylon and steelon. (Szostak et. al., 2004). Biodegradation of polymers is seen as one of
the solution for current plastic waste management problems. By definition biodegradable polymers are those
that are degraded into carbon dioxide, water and biomass as a result of the action of living organism or
enzymes. A degradation of polymers may proceed by one or more mechanisms, including microbial
degradation in which microorganisms such as fungi and bacteria consume the material. The rate of
biodegradation may vary substantially and depends on the molecular structure, morphology, surface area etc.
(Ursa et al., 2003). Among polymer category polyamide types of polymer have been considered as a long
standing existence. Therefore, find diversifies applications by all commodities. Polymers bearing recurring
amide groups in their backbone are defined as polyamide. Aliphatic polyamides, such as nylon 66 and nylon 6
have been produced industrially since the late 1930s and continue to be important materials. (Jozefa et. al.,
2007).

Due to its strong intermolecular cohesive force caused by hydrogen bonds between molecular chains of nylon,
the rate of degradation is less compared to polyesters (Tomita et. al., 2003). Nylon 6 monomer is metabolized
by numerous microorganisms, including the bacterial genera pseudomonas, Achromobacter and
corynebacterium and fungal genera Bjerkundera adusta. (Mohee R. et. al., 2007) So far, several investigations
on nylon degradation using microorganisms have been reported. Temita K. in 2003 reported thermophilic
bacterium degradation of some kinds of nylon.

In this paper we report on nylon biodegradation using fungi Trametes versicolor NCIM 1086 in a submerged
cultivation using nitrogenous nutrient broth as stimulator. The extent and nature of degradation of the polymer
was evaluated using several physical and chemical measurements namely, weight reduction tests, Fourier
Transform Infrared spectroscopy (FTIR).

Nylon-6:

Nylon-6, Nylon-11, Nylon-12 are all homopolymers. But Nylon-11 and Nylon-12 are formed by condensation
po- lymerization because their monomers (11-aminoundeca- noic acid and ω-aminolauric acid respectively)
contain both amine and acid functionalities in a single molecule (mon- omer) itself. [7] Nylon-12 can also be
produced by ring- opening polymerization of laurolactam at 260-300 ̊C. [8] Nylon-6 however is only formed by
ring opening polymeri- zation of ε-Caprolactam [9] as shown in figure 2.

Figure 2: polymerization reaction of nylon-6


CHEMISTRY

Nylon 6 is the linear addition polymer of caprolactam (6-amino-caproic acid). The polymerization process for
nylon 6 can be batch or continuous, however, the state-of-the-art process for its manufacture is continuous
polymerization. Three reversible reactions, hydrolysis, polycondensation, and polyaddition are the main steps
in nylon 6 production. The overall reaction is illustrated as follows:

Figure 3: polymerization reaction of nylon-6

The first step is a hydrolysis reaction to open the caprolactam ring, forming ε-aminocaproic acid:

This reaction proceeds in molten caprolactam in the presence of a small weight percent water. Although the
reaction will proceed with only caprolactam and water present, a material such as phosphoric acid is added at
low concentration to act as a chain stabilizer and help achieve the desired final viscosity (molecular weight).

Polyaddition is the reaction which is mainly responsible for the growth of the linear polymer chains. It is the
most important reaction as soon as a certain amount of end groups has been made available by the hydrolysis of
caprolactam. Thus, final polymerization occurs by the following caprolactam addition reaction:

The polymer dissolves in the unreacted caprolactam. The polymer end groups affect the stability and final
molecular weight of the polyamide. Organic acids (such as acetic acid) can be added as chain stabilizers.
Monofunctional organic amines can also be added.

The linear polymer chain formed in the polyaddition reaction can further increase its molecular weight via a
polycondensation reaction. The reactive end groups polycondensate forming linear chain molecules and
byproduct water. Thus, two linear chain molecules condense producing a longer chain molecule with higher
molecular weight. In other words, the polycondensation is regarded as the most important reaction in the last
phase of nylon 6 formation in which the distribution of polymer chain lengths is adjusted. Caprolactam can also
be polymerized in-situ in a mold. A typical procedure uses the sodium salt of caprolactam as a catalyst. A brief
discussion of the raw materials – caprolactam, additives, initiators, catalysts, and chain stabilizers and
additional ingredients used during production of nylon 6 is given.

Nylon 6,6 chemistry and raw materials are also discussed.

PRODUCTION PROCESSES

Nylon 6 Batch & Continuous Processes

Commercially, the ring-opening polymerization of caprolactam to nylon 6 can be accomplished by both


hydrolytic and anionic mechanisms. However, nylon 6 is produced almost exclusively by hydrolytic
polymerization of caprolactam because it is easier to control and better adapted for large-scale operation. The
polymerization process for nylon via the hydrolytic mechanism can be batch or continuous. The hydrolytic
process for nylon 6 contains the following steps: caprolactam and additives addition, hydrolysis, addition,
condensation, pelletizing, leaching/extraction of monomers, drying, and packaging.

Process flow diagrams and process descriptions for both the batch and continuous process are given in the
report.

Nylon 6,6 Batch Process

A batch nylon 6,6 process is described in this section and illustrated with a process flow diagram.

Nylon 6,6 Continuous Process

To solve the limitations inherent in the batch process, the continuous polymerization process was developed.
The main steps of the continuous process include salt preparation, and polymerization. Solid phase
polymerization is an additional step used to increase molecular weight of the polymer without damaging
properties of the polymer.

A conceptual process design for the Salt Preparation process is schematically illustrated, coupled with a brief
description.

The concentrated nylon salt solution is pumped from storage into the first-stage polymerization reactor, and this
is schematically illustrated along with a brief description.

A brief description of solid-phase polymerization (SPP) is given.

CURRENT COMMERCIAL TECHNOLOGIES

This section reviews the technical features of modern commercial processes offered by the major licensors of
polyamide technology. In the polyamide market, most producers have developed their own technology know-
how and the advantage stay with the developers. DuPont, for instance, has developed its own proprietary
technology. The basic production steps in manufacturing nylon have not changed significantly through the
years and several technology holders generally hold similar production features for most commercially
produced nylon: nylon 6 and nylon 6,6. Manufacturing technology, however, has improved from year to year in
terms of production efficiency, reduction in utility requirement, special features in reactor design to improve
quality and to minimize raw material. Major commercial licensors for polymer production process includes
Zimmer AG and Uhde Inventa-Fischer.

Lurgi Zimmer Gmbh process flow diagram and process description are given. 


Uhde Inventa-Fischer process is described along with schematic illustrations. 
 TECHNOLOGY


DEVELOPMENTS 
 Nylon 6 and nylon 6,6 have been commercially produced for almost seventy years. The
technology for producing nylon today is considered to be mature. However, every one of the many steps used
in nylon production has been the subject of numerous improvements over the years and important
developments are constantly being made with respect to process and equipment design and catalysts
improvements. 
 The technology developments for nylon 6 continuous productions have been focused on
further process advancements and cost reduction if a way can be found to avoid the lactam wash extraction
step. 
 Other trends in technology can be characterized as evolutionary – there does not appear to be a
revolutionary advance on the horizon. Areas where design improvements are being sought with the existing
continuous processes are improvements in energy utilization, improvements in quality, increases in scale, and
further improvements in capital utilization. The advances in technology and engineering of polyamide products
will lead to the development of differentiated new products, offering valuable solutions in existing and new
markets. 
 Most commercial improvements and developments for nylon production are generally treated as
confidential information. This technology section reviews recent published patents on process improvements,
new production technologies, new methods of recycling raw materials, and many more. However, it is not
known if these patents will be effectively applied in a commercial scale production or not. 


• PRODUCT AND END-USE


• Resins and Compounds
• The usefulness of nylons rests upon their combination of properties and their susceptibility to modification.
The key properties of nylon include resistance to oil and solvents, toughness, fatigue and abrasion
resistance, low friction and creep resistance, high tensile strength, thermal stability, fire resistance,
drawability, good appearance and good processability.
• Resins properties and additives and fillers are discussed; recycling, storage, and compounding are
mentioned in brief.
• Fabrication Methods
• Processability is another advantage that nylon has over thermosets and other engineering plastics. Nylon
can be processed via a variety of techniques including injection molding, extrusion, blow molding,
monomer casting, solution coating, fluidized-bed or electrostatic coating, or forming. The large proportion
of nylon is processed by injection molding, extrusion and blow molding.
• Injection Molding and Extrusion are briefly discussed; Blow Molding, Rotomolding, Reaction Injection
Molding, Assembly Techniques are also mentioned in brief.
• Nylon Major Markets
• Polyamide 6 and 6,6 are highly versatile materials that are consumed in a host of applications including
fibers, films, and molded articles. This section in the report focuses only on the technical, or engineering
polymer applications of polyamide 6 and 6,6.
• Automotive, electronics and electrical, consumer & other applications are briefly discussed; new
developments in Nylon 6 and 6,6 products are mentioned in brief.

Figure : 4

ECONOMIC ANALYSIS

Costs of production estimates for the following have been developed:

Production of Nylon 6 via batch process 


Production of Nylon 6,6 via batch process 


Production of Nylon 6 via continuous process 


Production of Nylon 6,6 via continuous process 
 In the petrochemical industry, feedstock integration is an
important consideration in assessing the competitive position of participants in a given value chain. This is true,
even though there is still a high-value added component to compounded nylon resin selling prices. With a
number of alternative routes to caprolactam and HMDA production under development, an understanding of
the potential impact of alternative pricing for these raw materials is important. 
 To test the effect of alternative
caprolactam or HMDA prices on nylon 6 and nylon 6,6 production costs, sensitivities have been prepared that
looked at these raw materials at alternative prices. Also, a sensitivity analysis was performed to test the impact
of larger sized lines on the economics of continuous units. 


MARKET ANALYSIS

Nylon was introduced to the market in the 1940s as the first synthetic fiber. From the 1950s onwards, nylon
demand for resin has steadily grown accounting for 38 percent of the global demand for nylon nowadays (as
shown in the Figure below). Among most types of polyamide, approximately 85-90 percent of nylon in the
global market are nylon 6 and nylon 6,6.

Global Nylon Consumption by End-Use

Injection Molding Resin
 30%

Extrusion Resin 8%

Fiber 62%

Supply and demand for North America, Europe Japan, and China are discussed. 


Nylon 6 and Nylon 6,6 engineering thermoplastics demand by end use for 2005-2007, 
 estimate for
2008 and forecast to 2012 is given for each of the regions above. 


Structure and related properties:

As the separation of the amide groups increases (by adding more methyl groups) and the polarity of the amide
groups is reduced, moisture absorbance is decreased. Resistance to thermal deformation is lowered due to more
flexibility and mobility in the methyl unit sections of the chain. In the case of Nylon-6,6 and Nylon-6,12, one
can clearly see this relationship. Nylon-6,12 has a lower modulus, higher elongation, lower strength, lower
thermal distortion tem- perature, lower hardness, and lower melting point than Nylon-6,6. However, Nylon-
6,12 absorbs half as much water on Nylon-6,6. Thus, even though the properties may not be as good as Nylon-
6,6 in dry conditions; the proper- ties of Nylon-6,12 will be much more consistent when it is used in
applications in which water may be present. The absorption of water has a significant effect on the proper- ties
of nylon.

Chemical and Physical properties:

Acid: Nylon 6, 6 is attacked by mineral acids is dis- integrated or dissolved almost. But is inert to dilute acetate
acid and formic acids even of the boil. It is dissolved in the concentrated formic acid. Nylon 6 is attacked by
mineral acid but resistant to dilute boiling organic acid.

Bleaches: Not attacked by oxidizing and reducing bleaches but may be harmed by chlorine and strong
oxidizing bleaches.

Alkali: Nylon is substantially inert to alkalis.

Organic solvent: Most of the solvent have little or no effect on nylon. Phenol metacressol and formic acid
dissolve the fibre but solvents used in stain removal 
 and dry cleaning do not damage

Light: No discoloration. Nylon 6 gradually loss of 
 strength on prolonged extension. 


Biological: Neither micro organism nor moth, larvae 
 attack nylon.

Electrical: High insulating properties leads to static 
 charges on the fibre. 


Flammability: Burns slowly. 


• Nylon-6, 6 shows greater strength as compared to Nylon-6 because of the greater hydrogen bonding shown in
Nylon-6, 6 as
 Melting point and crystallinity increase because of this greater hydrogen bonding
between adjacent chains. But this effect is not a regular one. The increase in melting point also depends
on whether the number of -CH2 groups present in between the CONH groups is even or odd. The odd
number of -CH2 groups between the amide groups in Nylon-6 allows complete hydrogen bonding when
the amides in the adjacent chains have an opposed or an an- tiparallel orientation but not when they
have the same or parallel orientation (as shown in the figure 4). Changing from a parallel to an
antiparallel array requires inverting the entire molecular chain in the odd numbered case. But only a
segment lateral movement is needed if there is an even number of -CH2 groups, as in the case of Nylon-
6, 6 with its intervening number of 4 and 6 -CH2 groups. It is this odd-even feature that accounts for the
lower melting point and percent crystallinity of Nylon-6 versus Nylon-6, 6. It is this reason in general
why Nylon-odd and Nylon- odd-even have lower melting points than comparable or similar Nylon-
even-even. 


• Material and methods


• Materials
• Commercial grade Nylon 6 was provided by Sigma Aldrich. The material is in the form of pellet. All
chemicals and solvents used in all experiment were AR grade. A thin sheet of nylon 6 was prepared from
nylon 6 pellets by melting and pressing the pellets of Nylon 6.

The fungus selected in the study was a white rot fungus Trametes versicolor NCIM 1086 that is well known for
its lignolytic activity. The tested fungal strain of the species Trametes versicolor NCIM 1086 was obtained
from the National Collection of Industrial

Microorganisms (NCIM) NCL, pune, Maharashtra, India.

Disinfection of the sample


The sample sheets were sterilized before they were inoculated into the test medium. The nylon sheets were
dipped in 1 % hypochlorite for a few hours. Washed with distilled water thoroughly in order to remove all the
hypochlorite and later dried. No physical or chemical changes were observed in the sample after hypochlorite
treatment.

Submerged cultivation procedure

A nylon sheet was exposed to submerged cultivation process Microbial degradation was performed in
Erlenmeyer flasks in shaker condition. Each flask containing small sheet of nylon 6 and 100 ml of the liquid
glucose – salt medium at a pH 6.25. The medium contained per liter of deionised water, 10 gm of glucose, 1 g
,
KH2PO4 0.5 gm of MgSO4 7H2O and 0.5 gm of (NH4)2 SO4 and 0.1 gm of CaCl2. Aliquots (100 ml) of
o
medium were poured into 500 ml Erlenmeyer flask and sterilized in an autoclave for 20 min at 121 C and 1.2
atm, after cooling the medium was inoculated with 5 ml of the fungi spore suspension obtained by suspending
spores from one agar slant tube in 20 ml sterile water. The fermentation broth was incubated on a rotary shaker
o
at 30 C and 90 rpm. Nylon 6 was the sole source of nitrogen in the medium. Degradation was left to proceed
for a period up to 90 days.

Results and discussion

Degradation of Nylon 6 sheets in submerged cultivation using Trametes versicolor NCIM 1086 was carried out
for 15, 30, 45, 60 ,75 and 90 days. Parallel to samples inoculated with the fungus (biotic sample) blank
experiment was carried out with Nylon 6 sheets placed equally composed media without the fungus (a biotic
sample). Results presented in the following sections were obtained from two independent sets of degradation
experiments.

• Increasing crystallinity increases 


• Stiffness


• Density

• 
 Tensile and yield stress

• 
 Chemical and abrasion resistance

• Better dimensional properties. 


However increasing crystallinity decreases

Elongation


Impact resistance
Thermal expansion

Permeability.

Water absorption as discussed earlier is characteristic of nylons. Unless compensated for by increased
crystallinity, a higher proportion of amide groups leads to higher water absorption. Increased water content has
an effect analogous to that of increased temperature, i.e., enhanced seg- mental mobility with concomitant loss
in stiffness and ten- sile strength, gain in toughness and growth in dimensions (elongation).

At very low temperature, however, water stiffens the nylon. Thus the brittleness temperature (ASTM D746) of
Nylon-6, 6 is-80°c if dry and - 65°c if conditioned to 50% relative humidity. Properties are frequently reported
in the “dry”, as- molded condition corresponding to about 0.2% water or less, and after equilibration to a
specified relative humidity such as 50 or 65% and occasionally to 100%.

Also nylons with fewer CONH groups and lower water ab- sorption have a lower dry Tg, but shows less change
of Tg with relative humidity. Thus we see that the mechanical properties of nylon depend greatly on the
crystallinity and water absorption.

.
Applications:

1. Nylon is a high strength fibre. It is used for making fishing nets, ropes, parachutes and type cords.

2. It is used for making fabrics in textile industry. Nylon creates draperies, flame-resistant products, and
clothes. It is often used for carpets.

3. Crinkled nylon fibres are used for making elastic hosiery. Most stockings for women are made from nylon.
Used to make and design clothing.

4. Nylon is widely used as plastic for making machine parts.

5. It is blended with wool to increase the strength.

6. Military applications such as parachutes, flak vests, and tires for vehicles.

7. Nylon threads are used for surgical suture, dresses, un- der garments, ties, tapestry.

Conclusion

Fungus Trametes versicolor NCIM 1086 mediated biodegradation of nylon 6. FTIR spectra for the polymer
nylon 6 indicate formation of new groups such as CH3, CHO and COOH. This group may be formed due to
process of hydrolysis and oxidation. This may be caused due to cleavage of C-C bond in CH2-CH2 adjacent to
Nitrogen atom, (Deguchi et. al 1997, Negoro et al., 1992,). Also the C=N stretching get weaker here.
Degradation of polymer was also confirmed by weight loss of nylon sheets and decrease in thickness of nylon
sheet. The color of sheets becomes brownish and surface morphology become rough when sheets are exposed
to fungi which shows effect of enzymatic activity on nylon 6. Therefore, the data indicates the potential for
degrading recalcitrant polymer such as nylon 6 by Trametes versicolor NCIM 1086.

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 9 | September 2016 • ISSN
No 2277 - 8179 | IF :e : 9 | September 2016 • ISSN No 2277 - 8179 | IF : 3.508 | IC Value : 69.48