27.1 Polymerization

Learning Objectives

By the end of this section, you will be able to:

  • Define the terms monomer and polymer.
  • Know some different examples of synthetic and natural polymers.

A polymer is a large molecule, or macromolecule, composed of many repeated subunits. The term “polymer” derives from the Greek word polus (meaning “many, much”) and meros (meaning “part”) and refers to a molecule whose structure is composed of multiple repeating units, from which originates a characteristic of high relative molecular mass and attendant properties. An example of a polymer is shown in Figure 27.1a.

Monomers undergo polymerization to form polymers, longer chains of individual units.
Figure 27.1a. Polymer formation during a polymerization reaction, a large number of monomers become connected by covalent bonds to form a single long molecule, a polymer. (Credit left: General Chemistry, CC BY-NC-SA 3.0, right: Image by K.R Roshith, CC BY-SA 4.0)

Due to their broad range of properties, both synthetic and natural polymers play essential and ubiquitous roles in everyday life. Polymers range from familiar synthetic plastics such as polystyrene to natural biopolymers such as DNA and proteins that are fundamental to biological structure and function. Polymers, both natural and synthetic, are created via polymerization of many small molecules, known as monomers. Their consequently large molecular mass relative to small molecule compounds produces unique physical properties, including toughness, viscoelasticity, and a tendency to form glasses and semicrystalline structures rather than crystals. The terms polymer and resin are often synonymous with plastic.

Natural Polymers

Some very important biological materials are polymers. Of the three major food groups, polymers are represented in two: proteins and carbohydrates. Proteins are polymers of amino acids, which are monomers that have an amine functional group and a carboxylic acid functional group. Proteins play a crucial role in living organisms.

Another example of a natural polymer involves linking hundreds of glucose molecules together to make a relatively common material known as starch.  Starch is an important source of energy in the human diet. Note, in Figure 27.1b., how the individual glucose units are joined together to form starch.

Repeating glucose units (each in a chair formation) are connected together by oxygen bonds forming a polymer structure known as starch.
Figure 27.1b. Polymer structure of starch with repeating glucose units. (Credit: Introductory Chemistry, CC BY-NC-SA 3.0)

Glucose molecules can also be joined together in another way, as shown in Figure 27.1c., to form a polymer known as cellulose.  Cellulose forms the strands found in cotton that we use in clothing.

The general structural formula of cellulose. There are two repeating units of glucose (each in the chair formation) connected by an oxygen bond to represent the polymer structure of cellulose contained with square brackets and a subscript n
Figure 27.1c. Polymer structure of cellulose with repeating glucose units. (Credit: Introductory Chemistry, CC BY-NC-SA 3.0)

Cellulose is a major component in the cell walls of plants. Curiously, despite the similarity in the building blocks between starch and cellulose, some animals (such as humans) cannot digest cellulose; those animals that can digest cellulose typically rely on symbiotic bacteria in the digestive tract for the actual digestion. Animals do not have the proper enzymes to break apart the glucose units in cellulose, so it passes through the digestive tract and is considered dietary fiber.

Deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) are also polymers, composed of long, three-part chains consisting of phosphate groups, sugars with 5 C atoms (ribose or deoxyribose), and N-containing rings referred to as bases. Each combination of the three parts is called a nucleotide; DNA and RNA are essentially polymers of nucleotides that have rather complicated but intriguing structures (Figure 27.1d.). DNA is the fundamental material in chromosomes and is directly responsible for heredity, while RNA is an essential substance in protein synthesis.  These natural polymers, or biopolymers (polymers produced by living organisms), are discussed further in Chapter 28.

An animation that shows a DNA double helix structure rotating.
Figure 27.1d. Nucleotides in DNA double helix (credit: animation by brian0918, PDM).

 

Synthetic Polymers

Synthetic polymers are often formed from monomers derived from fossil fuels and petroleum products.  Current research is focused on finding other more renewable sources of monomers.

Celluloid: Billiard Balls

Celluloids are a class of compounds created from nitrocellulose (partially nitrated cellulose) and camphor, with added dyes and other agents. Generally considered the first thermoplastic, it was first created as Parkesinein (by Alexander Parkes of Birmingham England) in 1856 and as Xylonite in 1869. In the 1860s, an American, John Wesley Hyatt, acquired Parkes’s patent and began experimenting with cellulose nitrate with the intention of manufacturing billiard balls, which until that time were made from ivory. In the 1870s the modified plastic was registered as “celluloid”.  The formation and structure of celluloid is shown in Figure 27.1e.

The main use was in movie and photography film industries, which used only celluloid film stock prior to the adoption of acetate safety film in the 1950s. Celluloid is highly flammable, difficult and expensive to produce and no longer widely used; its most common uses today are in table tennis balls, musical instruments, and guitar picks.

 

A box of 15 billiard balls specifically designed to commemorate the Bicentennial. This set is series #0001 of a limited edition. The Q ball has the dates “1776 / 1976” printed on its surface; the other balls are numbered one through 14.
Figure 27.1e. Billard balls representing the Bicentennial. (Credit right: work by MaChe, PDM; left: modification of work courtesy of the Gerald R. Ford Presidential Museum, PDM)

Bakelite

Bakelite (sometimes spelled Baekelite) or polyoxybenzylmethylenglycolanhydride was the first plastic made from synthetic components. It is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. It was developed by the Belgian-American chemist Leo Baekeland in Yonkers, New York, in 1907.

Bakelite was patented on December 7, 1909. The creation of a synthetic plastic was revolutionary for its electrical non conductivity and heat-resistant properties in electrical insulators, radio and telephone casings and such diverse products as kitchenware, jewelry, pipe stems, children’s toys, and firearms.  Figure 27.1f. shows examples of products made from Bakelite.

 

The figure on the left is a set of 24 Phenol formaldehyde resin buttons of various shapes, sizes, and colours; colours include different shades of green, red, white, and amber; some have brass fasteners. The one in the middle is a photo of a black telephone with a rotary dial and the image on the right is a photo of a marble-effect cocktail shaker with lid removed beside it.
Figure 27.1f. Examples of products made from Bakelite (credit a: “Set of Phenol formaldehyde resin buttons” by Gregory Tobias, CC BY-SA 3.0; b: work by William Warby, CC BY 2.0; c: work by Tangerineduel, CC BY-SA 4.0).

Watch Polymers: Crash Course Chemistry #45 – YouTube (10 min)

Video source: Crash Course. (2014, January 6). Polymers: Crash Course Chemistry #45 – YouTube [Video]. YouTube.

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Organic and Biochemistry Supplement to Enhanced Introductory College Chemistry Copyright © 2024 by Gregory Anderson; Caryn Fahey; Adrienne Richards; Samantha Sullivan Sauer; David Wegman; and Jen Booth is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

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