Bis(tert-butylphenyl)iodonium 10-camphorsulfonate
[CAS# 193345-23-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Salt of carboxylic acid ester and its derivatives
• Name: Bis(tert-butylphenyl)iodonium 10-camphorsulfonate
• Synonyms: bis(2-tert-butylphenyl)iodanium;(7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl)methanesulfonate
• Molecular Formula: C₃₀H₄₁IO₄S
• Molecular Weight: 624.61
• CAS Registry Number: 193345-23-2
• EC Number: 682-849-2
• SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)[O-])C.CC(C)(C)C1=CC=CC=C1[I+]C2=CC=CC=C2C(C)(C)C

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

Bis(tert-butylphenyl)iodonium 10-camphorsulfonate is an organoiodonium salt that has attracted attention due to its utility in photoinitiation and as a key reagent in photopolymerization processes. The discovery of this compound stems from the need for highly efficient photoinitiators that can enable rapid and controlled polymerization reactions, especially under ultraviolet (UV) light exposure. The development of iodonium salts as photoinitiators revolutionized the field of polymer chemistry by offering compounds that release reactive species when exposed to light, initiating polymerization without the need for elevated temperatures.

This compound belongs to a class of iodonium salts that are known for their ability to generate reactive intermediates, such as cations and free radicals, upon light exposure. The iodonium cation in Bis(tert-butylphenyl)iodonium 10-camphorsulfonate acts as a strong electron acceptor, which undergoes homolytic cleavage when subjected to UV radiation. This reaction results in the formation of active species that can catalyze the polymerization of various monomers, making it especially useful in applications such as coatings, adhesives, and 3D printing materials.

The use of 10-camphorsulfonate as the counterion in this compound is strategic, as it enhances the solubility of the iodonium salt in a range of organic solvents and increases its compatibility with different monomer systems. Camphorsulfonate is also a relatively non-toxic and stable anion, which makes the resulting salt suitable for a variety of industrial applications. This combination of the iodonium cation with the camphorsulfonate anion creates a robust photoinitiator that can efficiently drive polymerization reactions with minimal by-product formation.

In industrial applications, Bis(tert-butylphenyl)iodonium 10-camphorsulfonate is used predominantly in the manufacturing of UV-curable coatings and inks. Its ability to initiate rapid polymerization under UV light makes it ideal for applications that require quick setting times, such as in automotive coatings, electronics, and optical materials. The compound is also employed in the production of photoresists, which are essential in the fabrication of microelectronic devices. Photoresists require precise control over polymerization to create the intricate patterns necessary for semiconductor devices, and iodonium salts like this one provide the reliability needed for these advanced processes.

In recent years, the compound has also been explored for its use in biomedical applications, particularly in dental materials. UV-cured resins containing Bis(tert-butylphenyl)iodonium 10-camphorsulfonate as a photoinitiator are commonly used in dental restorations, where fast curing times and strong adhesion are critical. The low toxicity of the camphorsulfonate counterion makes the material safe for use in medical applications, while the high reactivity of the iodonium cation ensures effective polymerization of dental resins.

The synthesis of this compound generally involves the reaction of diphenyliodonium salts with tert-butylphenyl derivatives, followed by the introduction of the camphorsulfonate anion. The reaction conditions are carefully controlled to ensure the formation of a stable iodonium salt with the desired photoinitiating properties. The resulting compound is then purified and tested for its efficacy in various polymerization systems, with particular attention paid to its absorption properties and the efficiency of radical generation under UV light.