Flourinated compositions comprising phosphorus

Details Flourinated compositions comprising phosphorus Flourinated compositions comprising phosphorus

2001-08-06

2004-12-07

McAvoy, Ellen M. (Department: 1764)

Solid anti-friction devices, materials therefor, lubricant or se

Lubricants or separants for moving solid surfaces and...

Ptfe

C508S423000, C508S429000, C508S431000, C508S433000, C508S441000, C558S177000, C558S183000, C558S203000, C558S204000, C428S422000

Reexamination Certificate

active

06828284

ABSTRACT:

FIELD OF INVENTION
This invention relates to a fluorinated compound comprising phosphorus, to a composition comprising the compound, and to a process for producing the compound.
BACKGROUND OF THE INVENTION
Hereinafter trademarks are shown in upper case.
The fluorinated compounds can be used, for example, as surfactants and lubricants for example, for the computer disk industry, or as additives for perfluoropolyether (hereinafter PFPE) compositions including oil and grease lubricants to inhibit corrosion and rust of metals.
PFPEs have excellent thermal and oxidative stability and are used as greases, hydraulic fluids, and oils for service under extreme or demanding conditions under which conventional oils and greases are inadequate. Examples are uses at temperatures above 260° C. and up to 370° C. to 425° C., depending on the particular oil or grease. These oils and greases are available from a number of commercial sources, including E. I. du Pont de Nemours & Company, which markets them under the KRYTOX trademark. The term “grease” as used herein comprises one or more oils mixed with a particulate thickening agent, for instance particulate polytetrafluoroethylene.
While a PFPE grease per se is highly stable, it is permeable to oxygen and moisture. Thus, the grease does not form an effective barrier against rust and corrosion of metallic parts it contacts. Though generally the term “corrosion” refers to the oxidation of metal in contact with oxygen and “rust” refers to the oxidation of metal in contact with water, the term “corrosion” used herein, unless otherwise indicated, is interchangeable with or includes “rust”.
Sodium nitrite can be added as corrosion inhibitor to a PFPE grease, but it is not soluble in the grease. It is present as a particulate dispersion. Ideally, a rust and corrosion inhibitor is present in solution to provide better protection and to eliminate any potential problem of separation from the grease.
Many organic phosphorus compounds have been suggested as corrosion inhibitors for PFPE greases. For example, U.S. Pat. No. 3,306,855 discloses a perfluoroalkyl ether phosphate containing at least one acidic hydrogen and U.S. Pat. No. 5,550,277 discloses a variety of fully and partially esterified phosphates and phosphates, some of which are acidic. Some of these inhibitors contain large quantities of costly perfluoroalkyl substituents. Others, such as those partially esterified phosphates disclosed in U.S. Pat. No. 5,550,277, require formation of an intermediate fluoroether-substituted phenol that is very difficult to synthesize in a commercial process.
Furthermore, the use of acidic corrosion inhibitors is contraindicated in admixture with a PFPE grease containing the common sodium nitrite inhibitor because the acidic group can react with sodium nitrite to generate noxious nitrogen oxides. Since the presence of greases containing sodium nitrite has been pervasive and they are expensive to replace, there is a high probability that new greases will be placed in existing equipment lubrication reservoirs containing sodium nitrite.
Recently, U.S. Pat. No. 6,184,187 discloses many aryl-, perfluoroether-, and phosphorus-containing compounds having corrosion-inhibiting properties in admixture with PFPEs. A need remains, however, for corrosion inhibitors with higher thermal stability to match more closely the thermal stability of the PFPEs themselves.
SUMMARY OF THE INVENTION
According to a first embodiment of the invention, a composition that is or comprises a phosphorus-, perfluoropolyether-, and perfluoroalkyl-containing compound is provided wherein the compound comprises either (i) mono- or polyalkylene oxide linking groups between the phosphorus and the fluorocarbon group, or (ii) no linking group between the phosphorus and fluorocarbon group, or (iii) individual mixtures of (i) and (ii); and the fluorocarbon group can be the perfluoropolyether or perfluoroalkyl group.
According to a second embodiment of the invention, a composition that is or comprises a phosphorus-, perfluoropolyether-, and perfluoroalkyl-containing compound is provided, which is a partially esterified phosphate, a partially esterified phosphonate, a salt of a partially esterified phosphate, a salt of a partially esterified phosphonate, or mixtures of two or more thereof wherein the compound comprises either (i) mono- or poly-alkylene oxide linking groups between the phosphorus and the fluorocarbon group, or (ii) no linking group between the phosphorus and fluorocarbon group, or (iii) individual mixtures of (i) and (ii); and the fluorocarbon group can be the perfluoropolyether or perfluoroalkyl group.
DETAILED DESCRIPTION OF THE INVENTION
The following definitions, listed alphabetically, are employed herein.
a is 3 to 30;
b is zero or 1;
c and d are numbers such that the c/d ratio ranges from 0.01 to 0.5, and the formula weight ranges from 400 to 15,000;
e and f are numbers such that the e/f ratio ranges from 0.3 to 5, and the formula weight is from 400 to 15000;
E is oxygen or sulfur;
f see e and f above;
g, h and i are numbers such that (g+h) ranges from 1 to 50, the i/(g+h) ratio ranges from 0.1 to 0.05, and the formula weight is from 400 to 15,000;
j is a number such that the formula weight ranges from 400 to 15,000;
J is a fluoroalkyl group selected from the group consisting of CF
3
, C
2
F
5
, C
3
F
7
, CF
2
Cl, C
2
F
4
Cl, C
3
F
6
Cl, or mixtures of two or more thereof;
J
1
is a fluoroalkyl group selected from the group consisting of CF
3
, C
2
F
5
, CF
2
Cl, and C
2
F
4
Cl;
J
2
is C
2
F
5
or C
3
F
7
;
J
3
is selected from the group consisting of CF
3
, C
2
F
5
, and C
3
F
7
;
J
4
is CF
3
, or C
2
F
5
;
k is a number such that the formula weight ranges from 400 to 15,000;
l is a number such that the formula weight ranges from 400 to 15,000;
m has a value from 1 to 20;
M is hydrogen, alkali metal, alkaline earth metal, or ammonium;
p, q and r are numbers such that (p+q) ranges from 1 to 50, and the r/(p+q) ratio ranges from 0.1 to 0.05, and the formula weight is from 400 to 15,000;
each Q is independently F, Cl, or H;
r see p, q, and r above;
R is the same or different substituent chosen from hydrogen, alkyl, nitro, cyano, alkoxy, primary or secondary amino, sulfonyl, carboxyl, or phenoxy;
Rf is a polyether chain having a formula weight ranging from 400 to 15,000 and composed of repeating units selected from the group consisting of: (a) J-O—(CF(CF
3
)CF
2
O)
c
(CFXO)
d
CFZ, (b) J
1
-O—(CF
2
CF
2
O)
e
(CF
2
O)
f
CFZ
1
, (c) J
2
-O—(CF(CF
3
)CF
2
O)
j
CF(CF
3
), (d) J
3
-O—(CQ
2
—CF
2
CF
2
—O)
k
-CQ
2
-CF
2
—, (e) J
4
-O—(CF
2
CF
2
O)
1
CF
2
—, (f) J
3
-O—(CF(CF
3
)CF
2
O)
g
(CF
2
CF
2
O)
h
(CFX—O)
i
—CFZ-, and (g) mixtures of two or more thereof and the units with formulae CF
2
CF
2
O and CF
2
O are randomly distributed along the chain;
Rf
1
is Q-(C
m
F
2m
)— representing a monovalent branched or straight chain polyfluoroalkyl group;
Rf
2
is a divalent perfluoropolyether chain segment that can have a number average formula weight of 500 to 15,000 and can be selected from the group consisting of (i) (CF
2
CF
2
O)
e
(CF
2
O)
f
CF
2
—, (ii) (C
3
F
6
O)
p
(CF
2
CF
2
O)
q
(CFXO)
r
CF
2
—, (iii) (CF
2
CF
2
O)
k
(C
3
F
6
O)
1
CF(CF
3
)—, (iv) CF(CF
3
)O(C
3
F
6
O)
w
—Rf
3−
O—(C
3
F
6
O)
w
CF(CF
3
)—, (v) ((CQ
2
)CF
2
CF
2
O)
s
CF
2
CF
2
—, and mixtures of two or more thereof and the units with formulae CF
2
CF
2
O and CF
2
O are randomly distributed along the chain;
Rf
3
is linear or branched C
a
F
2a
;
s is a number such that the formula weight ranges from 400 to 15,000;
w is independently 2 to 20;
x is 0.05 to 1;
X is —F, —CF
3
, or mixtures thereof;
y is 0.05 to 2;
Y is (CH
2
)
z
O(CH
2
CH
2
O)
z
1
or C
6
R
4
O;
z is 1 to 4;
z
1
is 0, 1 or 2;
Z is —F, —Cl or —CF
3
;
Z
1
is —F or —Cl,
The compounds disclosed in the first embodiment of the invention are also referred to as Class A compounds. Representative compounds within Class A include those shown in Classes A(i), A(ii), and A(iii) having the formulae shown below.
Class A(i) compounds have a mono- or pol

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