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US4450360A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkylaryliodonium salts and method for making

Assignee: General Electric Co
•
Filing: 1982-03-12
•
Granted: 1984-05-22
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Expires: 2002-03-12
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Abstract

Abstract Arylalkyliodonium salts are provided which can be used as thermal or photoinitiators for polymerization of a wide variety of cationically polymerizable organic materials. Reaction is effected between an aryliodonium tosylate and an active hydrogen aliphatic organic compound, such as dimedone, to produce an intermediate arylalkyliodonium tosylate salt which is thereafter reacted with a polyfluoro metal or metalloid salt of an alkali or alkaline earth metal to produce the desired arylalkyliodonium polyfluoro metal or metalloid salt, such as dimedonylphenyliodonium hexafluoroarsenate.

Inventors

  • 👤 James V. Crivello
  • 👤 Julia L. Lee

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 16:49
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/673; C07C49/00; C07C49/20; C07C49/24; C07C49/245; C07C49/248; C07C49/255; C07C49/587; C07C49/703; C07C49/747; C07C49/753; C07C49/76; C07C49/82; C07C49/835; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/60; C07D319/00; C07D319/04; C07D319/06; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G85/00; C08L; C08L61/00; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/118

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 142 words
Arylalkyliodonium salts having the formula, [R-I-Y].sup.+ MF.sub.d.sup.- where R is a C.sub.(6-13) aryl radical, Y is a monovalent aliphatic or cycloaliphatic group selected from ##STR11## R 1 and R 4 are selected from hydrogen and C.sub.(1-8) alkyl radical R 2 and R 3 are ##STR12## or a mixture of ##STR13## where R 7 and R 8 are selected from C.sub.(1-13) organic radicals which together can form a C.sub.(6-13) aromatic radical, C.sub.(5-13) heterocyclic radical, or two C.sub.(6-13) aryl radicals, a mixture of C.sub.(1-8) alkyl and C.sub.(6-13) aryl, and a mixture of alkyl and oxyalkyl or alkyl and oxyaryl, and R 5 and R 6 are monovalent electron withdrawing groups selected from nitrile and a mixture of nitro and C.sub.(6-13) aryl M is a metal or metalloid selected from antimony, arsenic, phosphorus and boron, and d is an integer equal to from 4-6 inclusive.
Claim 2
Dependent Claim 142 words
Arylalkyliodonium salts having the formula, [R-I-Y].sup.+ MF.sub.d.sup.- where R is a C.sub.(6-13) aryl radical, Y is a monovalent aliphatic or cycloaliphatic group selected from ##STR11## R 1 and R 4 are selected from hydrogen and C.sub.(1-8) alkyl radical R 2 and R 3 are ##STR12## or a mixture of ##STR13## where R 7 and R 8 are selected from C.sub.(1-13) organic radicals which together can form a C.sub.(6-13) aromatic radical, C.sub.(5-13) heterocyclic radical, or two C.sub.(6-13) aryl radicals, a mixture of C.sub.(1-8) alkyl and C.sub.(6-13) aryl, and a mixture of alkyl and oxyalkyl or alkyl and oxyaryl, and R 5 and R 6 are monovalent electron withdrawing groups selected from nitrile and a mixture of nitro and C.sub.(6-13) aryl M is a metal or metalloid selected from antimony, arsenic, phosphorus and boron, and d is an integer equal to from 4-6 inclusive.
Claim 3
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR14##
Claim 4
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR14##
Claim 5
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR15##
Claim 6
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR15##
Claim 7
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR16##
Claim 8
Dependent Claim 7 words
An arylalkyliodonium salt having the formula, ##STR16##
Claim 9
Independent Claim 244 words
A method for making an alkylaryliodonium salt which comprise (A) effecting contact between substantially equal molar amounts of an alkylaryliodonium organic sulfonic acid salt having the formula, [RIY].sup.+ [QSO.sub.3 ].sup.- and a polyfluoroalkali metal or alkaline earth metal metalloid salt of the formula, XMF.sub.d in the presence of water, or an organic solvent, (B) recovering the resulting arylalkylpolyfluoro metalloid iodonium salt from the mixture of (1), and (C) washing the resulting arylalkyliodonium salt with a sufficient amount of water to eliminate alkali metal or alkaline earth metal organic sulfonic acid salts from the resulting arylalkyliodonium polyfluoro metalloid iodonium salt, where R is a C.sub.(6-13) aryl radical, Y is a monovalent aliphatic or cycloaliphatic group selected from ##STR17## R 1 and R 4 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 2 and R 3 are ##STR18## or a mixture of ##STR19## where R 7 and R 8 are selected from C.sub.(1-13) organic radicals which together can form a C.sub.(6-13) aromatic radical, C.sub.(5-13) heterocyclic radical, or two C.sub.(6-13) aryl radicals, a mixture of C.sub.(1-8) alkyl and C.sub.(6-13) aryl, and a mixture of alkyl and oxyalkyl, or a mixture of alkyl and oxyaryl, and R 5 and R 6 are monovalent electron withdrawing groups selected from nitrile and a mixture of nitro and C.sub.(6-13) aryl, Q is a C.sub.(1-13) organic radical, M is a metal or metalloid selected from antimony, arsenic, phosphorus and boron, and d is an integer equal to from 4-6 L inclusive.
Claim 10
Independent Claim 244 words
A method for making an alkylaryliodonium salt which comprise (A) effecting contact between substantially equal molar amounts of an alkylaryliodonium organic sulfonic acid salt having the formula, [RIY].sup.+ [QSO.sub.3 ].sup.- and a polyfluoroalkali metal or alkaline earth metal metalloid salt of the formula, XMF.sub.d in the presence of water, or an organic solvent, (B) recovering the resulting arylalkylpolyfluoro metalloid iodonium salt from the mixture of (1), and (C) washing the resulting arylalkyliodonium salt with a sufficient amount of water to eliminate alkali metal or alkaline earth metal organic sulfonic acid salts from the resulting arylalkyliodonium polyfluoro metalloid iodonium salt, where R is a C.sub.(6-13) aryl radical, Y is a monovalent aliphatic or cycloaliphatic group selected from ##STR17## R 1 and R 4 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 2 and R 3 are ##STR18## or a mixture of ##STR19## where R 7 and R 8 are selected from C.sub.(1-13) organic radicals which together can form a C.sub.(6-13) aromatic radical, C.sub.(5-13) heterocyclic radical, or two C.sub.(6-13) aryl radicals, a mixture of C.sub.(1-8) alkyl and C.sub.(6-13) aryl, and a mixture of alkyl and oxyalkyl, or a mixture of alkyl and oxyaryl, and R 5 and R 6 are monovalent electron withdrawing groups selected from nitrile and a mixture of nitro and C.sub.(6-13) aryl, Q is a C.sub.(1-13) organic radical, M is a metal or metalloid selected from antimony, arsenic, phosphorus and boron, and d is an integer equal to from 4-6 L inclusive.
Claim 11
Dependent Claim 16 words
A method in accordance with claim 5, where the arylalkyliodonium arylsulfonic acid salt is dimedonylphenyliodonium tosylate.
Claim 12
Dependent Claim 16 words
A method in accordance with claim 5, where the arylalkyliodonium arylsulfonic acid salt is dimedonyltolyliodonium tosylate.
Claim 13
Dependent Claim 17 words
A method in accordance with claim 5, where the alkali metal polyfluoro metalloid salt is potassium hexafluoroarsenate.
Claim 14
Dependent Claim 17 words
A method in accordance with claim 5, where the alkali metal polyfluoro metalloid salt is potassium hexafluorophosphate.
Claim 15
Dependent Claim 17 words
A method in accordance with claim 5, where the alkali metal polyfluoro metalloid salt is potassium hexafluoroantimonate.

References Cited (Backward Citations)

US3981897A Cited
US4238394A Cited
US4238619A Cited
US4329300A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-05-22 1987-11-21 1988-05-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-05-22 1991-11-21 1992-05-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-05-22 1995-11-21 1996-05-22 $7700.00 Window Closed / Lapsed

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