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US 4,399,071 AGranted
Method for making diaryliodonium salts
AssigneeGeneral Electric Company
InventorsJames V. Crivello, Julia L. Lee
Life of this patent
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Abstract
A method is provided for making certain diaryliodonium salts which are useful as photoinitiators for a variety of cationic polymerizable organic materials. Reaction is effected between an aromatic iodo compound and an arylorganic aromatic compound in the presence of a peroxy organic acid and an organic sulfonic acid.
Claims8
A method for making a diaryliodonium salt which comprises,
- (1) incrementally adding a peracid to a C.sub.(1-13) iodo aryl compound to provide a mixture of from about 1-3 moles of peracid per mole of iodo aryl compound,
- (2) combining the mixture of (1) with a mixture of a C.sub.(1-13) organic sulfonic acid and a C.sub.(6-13) aryl organic compound selected from a substituted and unsubstituted aromatic hydrocarbon to produce a mixture having about 1 mole of the C.sub.(1-13) organic sulfonic acid and about 1 mole of the aryl organic compound per mole of the iodo aryl compound,
- (3) allowing the ingredients of (2) to react to produce a diaryliodonium organosulfonic acid salt,
- (4) recovering the diaryliodonium organic sulfonic acid salt from (3),
- (5) effecting a metathesis between the diaryliodonium organic acid salt of (4) and a polyfluoro metal or metalloid salt of the formula,
- XMF.sub.d,
- (6) recovering the resulting diaryliodonium polyfluoro metalloid salt from the mixture of (5), and
- (7) washing the recovered diaryliodonium polyfluoro metalloid salt of (6) to effect removal therefrom of the by-product organic sulfonic acid metal salt,
- where M is a metal or metalloid, X is an ion of an element selected from hydrogen, alkali metals and alkaline earth metals, and d is an integer equal to 4-6 inclusive.
6 more elements
A method for making 4-methoxydiphenyliodonium hexafluoroantimonate which comprises
- (1) incrementally adding peracetic acid to iodobenzene at a temperature of below about 40.degree. C. to provide a mixture having from about 1 to 3 moles of peracetic acid per mole of iodobenzene,
- (2) combining the mixture of (1) with p-toluene sulfonic acid monohydrate and anisole to produce a mixture having about 1 mole of the p-toluene sulfonic acid monohydrate and anisole, per mole of the iodobenzene,
- (3) allowing the ingredients of the mixture of (2) to react to produce 4-methoxyphenyliodonium tosylate,
- (4) recovering the 4-methoxyphenyliodonium tosylate of (3),
- (5) effecting methathesis between the 4-methoxyphenyliodonium tosylate and sodium hexafluoroantimonate,
- (6) recovering the 4-methoxydiphenyliodonium hexafluoroantimonate from the mixture of (5) and
- (7) washing the 4-methoxydiphenyliodonium hexafluoroantimonate to effect the removal therefrom of sodium p-toluene sulfonic acid monohydrate.
4 more elements
Dependencies are inferred from the claim text.