Iodonium salts and process for the preparation thereof

Details Iodonium salts and process for the preparation thereof Iodonium salts and process for the preparation thereof

1994-06-08

1995-11-21

Nazario-Gonzalez, Porfirio

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

556 7, 556 13, 556 64, 556402, 556465, 522 15, 522 25, 568 6, 568 16, 568 17, C07F 718, C07F 502, C07F 900

Patent

active

054688906

DESCRIPTION:

BRIEF SUMMARY
This application is a request for U.S. examination under 35 U.S.C. 371 of International application No. PCT/EP92/02932, filed Dec. 17, 1992.
The invention relates to novel iodonium salts and a process for the preparation thereof.
Photoactive diaryliodonium salts are known from U.S. Pat. Nos. 4,264,703, 4,279,717, 4,399,071, 4,617,238 and EP-A 334 056 and are used as photoinitiators for the polymerization of cationically polymerizable organic substances, e.g. epoxides, vinyl ethers, organopolysiloxanes containing epoxy groups, organopolysiloxanes containing vinyloxy groups and olefins. However, the cationically polymerizable substances are non-polar to slightly polar, particularly if the polymerizable groups are present in organopolysiloxanes. EP-A 334 056 (laid open on Sep. 27, 1989, J. V. Crivello et al., General Electric Company) describes diaryliodonium salts where in each case an aryl radical is substituted by a long-chain alkoxy group.
It is an object of the invention to provide photoactive iodonium salts which can be used as photoinitiators for the polymerization of cationically polymerizable organic substances and which are soluble in these substances. The object is achieved by the invention.
The invention provides iodonium salts of the general formula ##STR3## in which
C is a monovalent aromatic hydrocarbon radical having from 6 to 14 carbon atoms per radical or a monovalent aromatic hydrocarbon radical containing at least one oxygen and/or sulfur atom and having from 5 to 14 ring atoms per radical,
D, E and F are each substituents of C, where
D is a radical of the formula
E is a radical of the formula
F is a radical of the formula
a is 1, 2 or 3,
b is 0, 1 or 2,
c is 0, 1 or 2,
x is 0 or 1,
y is 0 or 1, preferably 1,
R is a divalent hydrocarbon radical having from 1 to 18 carbon atoms per radical, which is uninterrupted or interrupted by at least one oxygen atom and/or one sulfur atom and/or one carboxyl group,
R.sup.1 is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms per radical, which is uninterrupted or interrupted by at least one oxygen atom,
R.sup.2 is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms per radical, which is uninterrupted or interrupted by at least one oxygen atom, and
R.sup.3 is a monovalent hydrocarbon radical having from 1 to 10 carbon atoms per radical, which is uninterrupted or interrupted by at least one oxygen atom and/or one sulfur atom,
B is a radical of the formula ##STR4## where E and F are each a radical bound to the benzene ring in the 2-, 3-, 4-, 5- or 6-position, and the radicals E and F have the meanings specified for them above,
d is 0, 1 or 2,
e is 0, 1 or 2 and
X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group consisting of SbF.sub.6.sup.-, ClO.sub.4.sup.-, HSO.sub.4.sup.- and CF.sub.3 SO.sub.3.sup.-.
Examples of aromatic hydrocarbon radicals C are the phenyl, naphthyl and anthryl radicals.
Examples of aromatic hydrocarbon radicals C containing at least one oxygen and/or sulfur atom are the 2-furyl, 3-furyl, 2-thienyl and 3-thienyl radicals.
Preferably the radical A is a radical of the formula ##STR5## where D, E and F are each a radical bound to the benzene ring in the 2-, 3-, 4-, 5- or 6-position,
D, E and F have the meanings specified for them above and
b' is 0 or 1 and
c' is 0 or 1.
Examples of the divalent hydrocarbon radical R are --CH.sub.2 --, --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4-- and --(CH.sub.2).sub.6 --.
Examples of the divalent hydrocarbon radical R which is interrupted by at least one oxygen atom and/or sulfur atom and/or one carboxyl group, are --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --OCH.sub.2 CH.sub.2 CH.sub.2 -- and --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 --.
Examples of hydrocarbon radicals R.sup.1 are alkyl radicals such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert.-butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.-pentyl radicals; hexyl radicals

REFERENCES:
patent: 4264703 (1981-04-01), Crivello
patent: 4279717 (1981-07-01), Eckberg et al.
patent: 4399071 (1983-08-01), Crivello et al.
patent: 4513137 (1985-04-01), Koser et al.
patent: 4617238 (1986-10-01), Crivello et al.
patent: 5073643 (1991-12-01), Crivello
J. Org. Chem., vol. 45, No. 8, pp. 1543-1544 (1980).
J. Org. Chem. 1981, 46, 4324-4326, "Functionalization of Alkenes and Alkynes with [Hydroxy(tosyloxy)iodo]benzene".
Derwent Abstract 91-126486/18 (1991).

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