Perfluorinated amide salts and their uses as ionic...

Details Perfluorinated amide salts and their uses as ionic... Perfluorinated amide salts and their uses as ionic...

1998-12-03

2001-11-20

Kopec, Mark (Department: 1751)

Compositions

Electrically conductive or emissive compositions

C429S199000, C429S200000, C429S245000, C029S623100, C564S096000, C564S098000, 56, C361S327000

Reexamination Certificate

active

06319428

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to ionic compounds in which the anionic charge is delocalized, and their uses.
2. Description of the Background
It is known and it is particularly interesting to introduce ionic groups in molecules or organic polymers having various functions. Coulombic stresses correspond, indeed, to the stronger interactions which are available at the molecular level, and the ionic groups modify in an utmost manner the molecules to which they are bonded. Coloring matters which are made soluble in water by means of sulfonate or carboxylate functions may be mentioned.
However, the groups of this types, —CO
2
−
1/mM
m+
or —SO
3
−
1/mM
m+
, are not dissociated, and they do not induce solubility in solvents other than water or certain highly polar protic solvents such as light alcohols, which considerably restrict the scope of their utilization.
On the other hand, salts of the compounds [R
F
SO
2
—N—SO
2
R
F
]
−
1/mM
m+
in which R
F
is a perfluorinated group and M
m+
is a cation of valence m+ are known, which are soluble and are dissociated in organic aprotic media or solvating polymers. It is however considered that the existence of two perfluoroalkylsulfonyl groups (in particular the existence of fluorine atoms on the &agr; atom of carbon of each sulfonyl group) which exert an important attracting power on the electrons of the ionic charge, is a necessary condition to obtaining properties of solubility and dissociation. For example, the pK
a
of the acid H[CF
3
SO
2
—N—SO
2
CF
3
] is only 1.95, which compares to that of the non-fluorinated acid CH
3
SO
3
H (pK
a
=0.3) and is clearly inferior to that of perfluorinated acid CF
3
SO
3
H (pK
a
<−9) because of the basic character of the central nitrogen atom with respect to the oxygen atom of sulfonic acids.
SUMMARY OF THE INVENTION
Surprisingly, the inventors have found that the excellent properties of solubility and dissociation of the ionic groups —SO
2
—N—SO
2
— were maintained when a single sulfonated group has fluorine atoms on atoms which are adjacent to the sulfur atom, giving an extremely wide choice of functional molecules. In a manner also quite unexpected, it has been noted that it was possible for obtaining the same properties, to omit the group —SO
2
bound to the non-perfluorinated group provided that the group which is directly bound to nitrogen has a Hammett parameter &sgr;* higher than 0.6. By way of comparison, the Hammett parameters &sgr;* of a group —SO
2
— bound to a non-perfluorinated group is 3.5 and 4.55 for a group CF
3
SO
2
—.
The present inventors have also found that the sulfonyl —SO
2
— groups could be replaced, with minor variations of properties, by sulfinyl —SO— or phosphonyl —PO═ groups.
It is consequently an object of the present invention to provide a family of ionic compounds having a good solubility and a good dissociation, without having to rely on complex modifications of the starting molecule. The precursors of the molecule of the invention are found in the form of derivatives of sulfonic acids or of amine groups on the one hand, and derivatives of perfluorosulfonyl types on the other hand, which for the most part are industrial products and/or are easily accessible. In addition, it should be noted that a decrease of the perfluorinated fraction in the compounds of the invention enables to reduce the production costs of said compounds and consequently the cost of the applications in which they are involved.


REFERENCES:
patent: 3793079 (1974-02-01), Brown et al.
patent: 4851307 (1989-07-01), Armand et al.
patent: 5072040 (1991-12-01), Armand
patent: 5273840 (1993-12-01), Dominey
patent: 5446134 (1995-08-01), Armand et al.
patent: 5502251 (1996-03-01), Pohmer et al.
patent: 5514493 (1996-05-01), Waddell et al.
patent: 5609990 (1997-03-01), Ha et al.
patent: 5654112 (1997-08-01), Itou et al.
patent: 5691081 (1997-11-01), Krause et al.
patent: 5817376 (1998-10-01), Everaerts et al.
patent: 5874616 (1999-02-01), Howells et al.
patent: 5962546 (1999-10-01), Everaerts et al.
patent: 6063522 (2000-05-01), Hamrock et al.
patent: 0 571 832 (1993-05-01), None
patent: 731 518 (1996-11-01), None
patent: 95/26056 (1995-09-01), None
patent: WO 96/24929 (1996-08-01), None
patent: WO 96/24928 (1996-08-01), None
patent: WO 97/23448 (1997-07-01), None
patent: WO 97/35930 (1997-10-01), None
patent: WO 97/35929 (1997-10-01), None
patent: WO 98/50349 (1998-11-01), None
patent: WO 00/10969 (2000-03-01), None
patent: WO 00/11742 (2000-03-01), None
Banks et al “N-AALOGENO Compounds . . . ” Journal of Fluorine Chemistry, 46 (1990) 297-305.*
Potrov et al “Synthesis of Poly Fluoro-2-alleanesulfonyl-3,3-dialkyloxaziridinos” Journal of Fluorine Chemistry, 68 (1994) 277-286.*
Lis et al “Synthesis and Antiarrhythmic Activity . . . ” J. Med. Chem. 1987, 30, 696-704.

Affiliated with

Also associated with

Rating

Perfluorinated amide salts and their uses as ionic... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Perfluorinated amide salts and their uses as ionic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Perfluorinated amide salts and their uses as ionic... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2603011