Functional trifluorovinyl monomers and their...

Details Functional trifluorovinyl monomers and their... Functional trifluorovinyl monomers and their...

2001-07-31

2004-06-22

Lipman, Bernard (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S245000, C526S246000, C525S276000

Reexamination Certificate

active

06753392

ABSTRACT:

The present invention relates to fluoromonomers. It also relates to processes for the copolymerization of fluoromonomers with fluoroolefins, to the resulting copolymers and to the use of these monomers in forming in particular fluoroelastomers. In addition, the present invention relates to a process for the crosslinking of these copolymers.
A large number of fluoromonomers have already been disclosed in the literature.
The synthesis of fluoroolefins corresponding to the general formula CF
2
═CF(CF
2
)
m
(CH
2
)
n
OH (with m=0 to 10 and n=1 to 4) is disclosed in Patent Application EP 0 138 091. The use of fluoroolefins as comonomers of vinylidene fluoride is also envisaged.
Patent Application EP 0 135 917 discloses fluorocopoymers formed by copolymerization of vinylidene fluoride with fluoroolefins of general formula CF
2
═CF(CF
2
)
m
(CH
2
)
n
X (with X=OH, COOH or an epoxide group, m=0 to 10 and n=1 to 4). The copolymerization of some of these compounds with vinylidene fluoride is described therein.
Patent U.S. Pat. No. 3,483,263 discloses the synthesis of unsaturated haloalcohols corresponding to the formula CX
1
X
2
═CX
3
—A—OH in which X
1
to X
3
represent halogen atoms and A represents an alkylene group comprising at least two carbon atoms.
T. Nguyen et al., in J. Organic. Chem., 54(23), 5640-5642, 1989, disclose the synthesis of a compound corresponding to the formula CF
2
═CFCH
2
OH by addition of methyllithium to 2,2,3,3-tetrafluoropropanol.
The document SU 375298 discloses the use of CF
2
═CFCH
2
OH in the preparation of O-(2,3,3-trifluoroalkyl) phosphonates.
The document WO 86/07590 relates to pesticides corresponding to the general formula CF
2
═CF—(CH
2
)
n
—X—R in which X can be O, N, S or CH
2
and n can have the values from 1 to 4, the value of R depending on the meaning of X.
The use of compounds of formula CF
2
═CF—CH
2
Q as pesticides is revealed in United States of America Patent U.S. Pat. No. 5,514,717.
W. R. Dolbier et al., in J. Chem. Soc. Perkin Trans., 2, 219-232, 1998, analysed the cyclization activities of hex-5-enyl radicals and disclosed, inter alia, the synthesis of the compound 4,5,5-trifluoropent-4-enol.
T. Dubuffet et al., in J. Organomet. Chem., 341, 11-18, 1998, reveal a process for the opening of oxetanes under the action of fluorinated organolithium derivatives. Test 13 gives access to the compound 4,5,5-trifluoropent-4-enol.
An object of the present invention consists in making available novel fluoromonomers.
This object is achieved by compounds corresponding to the formula I
CF
2
═CF—(CH
2
)
m
—W  (I)
in which
m has the value 1, 2 or 3,
W represents a CH(OH)CH
2
OH group, a
group,
in which
R
1
, R
2
, R
3
and R
4
independently represent a hydrogen atom, a C
1
-C
20
alkyl group or an optionally substituted aryl group
R
5
and R
6
independently represent a hydrogen atom, a C
1
-C
20
alkyl group or an optionally substituted aryl group, with the proviso that, when R
5
represents a hydrogen atom, R
6
is other than a phenyl group when m has the value 1
R
7
and R
8
independently represent a hydrogen atom, a C
1
-C
20
alkyl group or an optionally substituted aryl group, with the proviso that R
7
and R
8
do not both represent a hydrogen atom or an ethyl group when m has the value 1
Y represents an oxygen atom or a sulphur atom and
Z represents a hydrogen atom, a CH
2
CH
2
OH group, a CH
2
COOH group or a COCH
3
group,
with the proviso that, when W represents CH(OH)CH
2
OH, m has the value 1, when Y represents an oxygen atom, Z is not a hydrogen atom and, when Y represents S, m has the value 3.
More particularly, the present invention provides compounds corresponding to the formula II
CF
2
═CF—C
3
H
6
—Y—Z  (II)
in which Y and Z are as defined above.
Another compound according to the present invention corresponds to the formula
CF
2
═CF═CH
2
—CH(OH)—CH
2
OH.
Another object of the present invention is a copolymerization process comprising the reaction of a compound corresponding to the formula I′
CF
2
═CF—(CH
2
)
m
—W′  (I′)
in which
m has the value 1, 2 or 3,
W′ represents a CH(OH)CH
2
OH group, a CH═CH
2
group,
in which
R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
independently represent a hydrogen atom, a C
1
-C
20
alkyl group or an optionally substituted aryl group
Y represents an oxygen atom or a sulphur atom and
Z′ represents a hydrogen atom, a CH
2
CH
2
OH group, a CH
2
COOH group or a COCH
3
group,
with a compound corresponding to the formula III
CF
2
═CX
2
  (III)
in which
X independently represents a hydrogen atom or a fluorine atom
with the proviso that, when m has the value 1 and X represents a hydrogen atom, W′ does not represent a
group,
so as to obtain a fluorocopolymer.
One embodiment of the present invention is a copolymerization process comprising the reaction of a compound corresponding to the formula I′
in which
m has the value 1, 2 or 3,
W′ represents Y—Z′ and Y represents an oxygen atom and Z′ represents a hydrogen atom
with a compound corresponding to the formula III in which X independently represents a hydrogen atom or a fluorine atom
so as to obtain a copolymer corresponding to the formula IV
n, p and r independently representing natural integers.
An additional aspect of the present invention is a copolymerization process comprising the reaction of a compound corresponding to the formula I′
in which
m has the value 1, 2 or 3,
W′ represents Y—Z′ and Y represents an oxygen atom and Z′ represents a COCH
3
group
with a compound corresponding to the formula III in which X independently represents a hydrogen atom or a fluorine atom
so as to obtain a copolymer corresponding to the formula V
n, p and r independently representing natural integers.
The present invention also envisages a copolymerization process comprising the reaction of a co compound corresponding to the formula I′
in which
m has the value 1, 2 or 3,
W′ represents Y—Z′ and Y represents a sulphur atom and Z′ represents a COCH
3
group
with a compound corresponding to the formula III in which X independently represents a hydrogen atom or a fluorine atom
so as to obtain a copolymer corresponding to the formula VI
n, p and r independently representing natural integers.
According to yet another preferred embodiment, a copolymerization process is provided comprising the reaction of a compound corresponding to the formula I′
CF
2
═CF—(CH
2
)
m
—W′  (I′)
in which
m has the value 1, 2 or 3,
W′ represents a CH(OH)CH
2
OH group, a CH═CH
2
group,
in which
R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
independently represent a hydrogen atom, a C
1
-C
20
alkyl group or an optionally substituted aryl group
Y represents an oxygen atom or a sulphur atom and
Z′ represents a hydrogen atom, a CH
2
CH
2
OH group, a CH
2
COOH group or a COCH
3
group,
with a compound corresponding to the formula III
CF
2
═CX
2
  (III)
in which
X independently represents a hydrogen atom or a fluorine atom
and with an olefinic compound
so as to obtain a copolymer.
More particularly, the invention relates to a copolymerization process comprising the reaction of a compound corresponding to the formula I′
in which
m has the value 1, 2 or 3,
W′ represents Y—Z′ and Y represents an oxygen atom and Z′ represents a hydrogen atom
with a compound corresponding to the formula III in which X independently represents a hydrogen atom or a fluorine atom
and with an olefinic compound of formula CH
2
═CHR′ with R′ representing a hydrogen atom or a C
1
-C
4
alkyl group so as to obtain a copolymer corresponding to the formula VII
l, n, p and r independently representing natural integers. Examples of C
1
-C
4
alkyl groups are ethylene, propylene and butylene.
Fluoropolymers possess outstanding properties, such as their hydro- and ble

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