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Concept
Phenol formaldehyde resin
Summary
Phenol formaldehyde resins (PF) (phenolic resins or phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commercial synthetic resins (plastics). They have been widely used for the production of molded products including billiard balls, laboratory countertops, and as coatings and adhesives. They were at one time the primary material used for the production of circuit boards but have been largely replaced with epoxy resins and fiberglass cloth, as with fire-resistant FR-4 circuit board materials.
There are two main production methods. One reacts phenol and formaldehyde directly to produce a thermosetting network polymer, while the other restricts the formaldehyde to produce a prepolymer known as novolac which can be moulded and then cured with the addition of more formaldehyde and heat. There are many variations in both production and input materials that are used to produce a wide variety of resins for special purposes.
Phenol-formaldehyde resins, as a group, are formed by a step-growth polymerization reaction that can be either acid- or base-catalysed. Since formaldehyde exists predominantly in solution as a dynamic equilibrium of methylene glycol oligomers, the concentration of the reactive form of formaldehyde depends on temperature and pH.
Phenol reacts with formaldehyde at the ortho and para sites (sites 2, 4 and 6) allowing up to 3 units of formaldehyde to attach to the ring. The initial reaction in all cases involves the formation of a hydroxymethyl phenol:
HOC6H5 + CH2O → HOC6H4CH2OH
The hydroxymethyl group is capable of reacting with either another free ortho or para site, or with another hydroxymethyl group. The first reaction gives a methylene bridge, and the second forms an ether bridge:
HOC6H4CH2OH + HOC6H5 → (HOC6H4)2CH2 + H2O
2 HOC6H4CH2OH → (HOC6H4CH2)2O + H2O
The diphenol (HOC6H4)2CH2 (sometimes called a "dimer") is called bisphenol F, which is an important monomer in the production of epoxy resins.
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Cross-link
In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural polymers (such as proteins). In polymer chemistry "cross-linking" usually refers to the use of cross-links to promote a change in the polymers' physical properties. When "crosslinking" is used in the biological field, it refers to the use of a probe to link proteins together to check for protein–protein interactions, as well as other creative cross-linking methodologies.
Thermoset polymer matrix
A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle. They were first used after World War II, and continuing research has led to an increased range of thermoset resins, polymers or plastics, as well as engineering grade thermoplastics.
Bakelite
Bakelite (ˈbeɪkəlaɪt ), formally Polyoxybenzylmethyleneglycolanhydride, is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. The first plastic made from synthetic components, it was developed by the Belgian chemist and inventor Leo Baekeland in Yonkers, New York in 1907, and patented on December 7, 1909 (). Because of its electrical nonconductivity and heat-resistant properties, it became a great commercial success.
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