chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, cyanate esters are

chemical substance A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., wi ...

s in which the

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

atom of the phenolic

OH group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...

is substituted by a

cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...

group (). The resulting product with a

cyanate Cyanate is an anion with the structural formula , usually written . It also refers to any salt containing it, such as ammonium cyanate. It is an isomer of the much less stable fulminate anion .William R. Martin and David W. Ball (2019): "Sma ...

group is termed a cyanate

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

. Cyanate esters based on a

bisphenol The bisphenols () are a group of chemical compounds related to diphenylmethane. Most are based on two hydroxyphenyl functional groups linked by a methylene bridge. Exceptions include bisphenol S, P, and M. "Bisphenol" is a common name; the lett ...

or novolac derivative are used in the production of resins.

Use in resins

Cyanate esters can be cured and postcured by heating, either alone at elevated temperatures or at lower temperatures in presence of a suitable catalyst. The most common catalysts are transition metal complexes of cobalt, copper, manganese and zinc. The result is a

thermoset In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening (" curing") a soft solid or viscous liquid prepolymer ( resin). Curing is induced by heat or suitable radiation ...

material with a very high

glass-transition temperature The glass–liquid transition, or glass transition, is the gradual and reversible transition in amorphous materials (or in amorphous regions within semicrystalline materials) from a hard and relatively brittle "glassy" state into a viscous or rub ...

(T_g) of up to 400 °C, and a very low

dielectric constant The relative permittivity (in older texts, dielectric constant) is the permittivity of a material expressed as a ratio with the electric permittivity of a vacuum. A dielectric is an insulating material, and the dielectric constant of an insulat ...

, providing excellent long term thermal stability at elevated end use temperatures, very good fire, smoke and toxicity performance and specific suitability for

printed circuit board A printed circuit board (PCB; also printed wiring board or PWB) is a medium used in Electrical engineering, electrical and electronic engineering to connect electronic components to one another in a controlled manner. It takes the form of a L ...

s installed in critical electrical devices. This is also due to its low moisture uptake. This property, together with a higher toughness compared to epoxies, also makes it a valuable material in aerospace applications. For example, the Lynx Mark II

spaceplane A spaceplane is a vehicle that can fly and glide like an aircraft in Earth's atmosphere and maneuver like a spacecraft in outer space. To do so, spaceplanes must incorporate features of both aircraft and spacecraft. Orbital spaceplanes te ...

is primarily made of carbon/cyanate ester. The chemistry of the cure reaction is a

trimerization In chemistry, a trimer (; ) is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors ofte ...

of three CN groups to a

triazine Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common. Structure The triazines have planar six-membered benzene-like ring but ...

ring. When the monomer contains two cyanate groups the resulting structure is a 3D

polymer network In polymer chemistry, branching is the regular or irregular attachment of side chains to a polymer's backbone chain. It occurs by the replacement of a substituent (e.g. a hydrogen atom) on a monomer subunit by another covalently-bonded ch ...

. Thermoset polymer matrix properties can be fine tuned by the choice of

substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...

s in the bisphenolic compound.

Bisphenol A Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial s ...

and novolac based cyanate esters are the major products;

bisphenol F Bisphenol F (BPF; 4,4′-dihydroxydiphenylmethane) is an organic compound with the chemical formula . It is structurally related to bisphenol A (BPA), a popular precursor for forming plastics, as both belong to the category of molecules known as b ...

and

bisphenol E The bisphenols () are a group of chemical compounds related to diphenylmethane. Most are based on two hydroxyphenyl functional groups linked by a methylene bridge. Exceptions include bisphenol S, P, and M. "Bisphenol" is a common name; the lette ...

are also used. The aromatic ring of the bisphenol can be substituted with an allylic group for improved toughness of the material. Cyanate esters can also be mixed with

bismaleimide Maleimide is a chemical compound with the formula H2C2(CO)2NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Malei ...

s to form BT-resins or with epoxy resins to optimize the end use properties.

References

{{DEFAULTSORT:Cyanate Ester Cyanates Functional groups Esters