Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as “Other”, 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

Structure[edit]

Carbonate esters have planar OC(OC)₂ cores, which confers rigidity. The unique O=C bond is short (1.173 Å in the depicted example), while the C-O bonds are more ether-like (the bond distances of 1.326 Å for the example depicted). Polycarbonates received their name because they are polymers containing carbonate groups (−O−(C=O)−O−). A balance of useful features, including temperature resistance, impact resistance and optical properties, positions polycarbonates between commodity plastics and engineering plastics.

Production

Phosgene route

The main polycarbonate material is produced by the reaction of bisphenol A (BPA) and phosgene COCl
₂. The overall reaction can be written as follows:

The first step of the synthesis involves treatment of bisphenol A with sodium hydroxide, which deprotonates the hydroxyl groups of the bisphenol A.^[6]

(HOC₆H₄)₂CMe₂ + 2 NaOH → Na₂(OC₆H₄)₂CMe₂ + 2 H₂O

The diphenoxide (Na₂(OC₆H₄)₂CMe₂) reacts with phosgene to give a chloroformate, which subsequently is attacked by another phenoxide. The net reaction from the diphenoxide is:

Na₂(OC₆H₄)₂CMe₂ + COCl₂ → 1/n [OC(OC₆H₄)₂CMe₂]_n + 2 NaCl

In this way, approximately one billion kilograms of polycarbonate is produced annually. Many other diols have been tested in place of bisphenol A, e.g. 1,1-bis(4-hydroxyphenyl)cyclohexane and dihydroxybenzophenone. The cyclohexane is used as a comonomer to suppress crystallisation tendency of the BPA-derived product. Tetrabromobisphenol A is used to enhance fire resistance. Tetramethylcyclobutanediol has been developed as a replacement for BPA.^[6]

Transesterification route

An alternative route to polycarbonates entails transesterification from BPA and diphenyl carbonate:

(HOC₆H₄)₂CMe₂ + (C₆H₅O)₂CO → 1/n [OC(OC₆H₄)₂CMe₂]_n + 2 C₆H₅OH^[6]

Properties and processing

Polycarbonate is a durable material. Although it has high impact-resistance, it has low scratch-resistance. Therefore, a hard coating is applied to polycarbonate eyewear lenses and polycarbonate exterior automotive components. The characteristics of polycarbonate compare to those of polymethyl methacrylate (PMMA, acrylic), but polycarbonate is stronger and will hold up longer to extreme temperature. Thermally processed material is usually totally amorphous,^[7] and as a result is highly transparent to visible light, with better light transmission than many kinds of glass.

Polycarbonate has a glass transition temperature of about 147 °C (297 °F),^[8] so it softens gradually above this point and flows above about 155 °C (311 °F).^[9] Tools must be held at high temperatures, generally above 80 °C (176 °F) to make strain-free and stress-free products. Low molecular mass grades are easier to mold than higher grades, but their strength is lower as a result. The toughest grades have the highest molecular mass, but are more difficult to process.

Unlike most thermoplastics, polycarbonate can undergo large plastic deformations without cracking or breaking. As a result, it can be processed and formed at room temperature using sheet metal techniques, such as bending on a brake. Even for sharp angle bends with a tight radius, heating may not be necessary. This makes it valuable in prototyping applications where transparent or electrically non-conductive parts are needed, which cannot be made from sheet metal. PMMA/Acrylic, which is similar in appearance to polycarbonate, is brittle and cannot be bent at room temperature.

Main transformation techniques for polycarbonate resins:

• extrusion into tubes, rods and other profiles including multiwall
• extrusion with cylinders (calenders) into sheets (0.5–20 mm (0.020–0.787 in)) and films (below 1 mm (0.039 in)), which can be used directly or manufactured into other shapes using thermoforming or secondary fabrication techniques, such as bending, drilling, or routing. Due to its chemical properties it is not conducive to laser-cutting.
• injection molding into ready articles