Polyaramid comprising fluorovinylether functionalized aromatic moieties
AssigneeE. I. Du Pont de Nemours and Company
InventorsNeville Everton Drysdale, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
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Abstract
The invention is directed to polyaramid polymers, comprising repeat units of the condensation product of a fluorovinylether functionalized aromatic diacid chloride and an aromatic diamine, and methods to make said polyaramid polymers. The polymers of this invention are useful as high strength fibers or solution cast films with reduced surface susceptibility to oil.
Claims33
a polymer comprising a fluorovinyl ether functionalized aromatic repeat unit represented by the structure (I)
- wherein,
- Ar represents a benzene or naphthalene radical;
- each R is independently H, C1-C10 alkyl, C5-C15 aryl, C6-C20 arylalkyl;
- OH, or a radical represented by the structure (II)
- with the proviso that only one R can be OH or the radical represented by the structure (II);
- each R1 is independently H, C1-C10 alkyl, C5-C15 aryl, C6-C20 arylalkyl;
- X is O or CF2;
- Z is H, Cl, or Br;
- a=0 or 1;
- and,
- Q is represented by the structure (Ia)
- wherein q=0-10;
- Y is O or CF2;
- Rf1 is (CF2)n, wherein n is 0-10;
- and,
- Rf2 is (CF2)p, wherein p is 0-10, with the proviso that when p is 0, Y is CF2.
A process, comprising combining a fluorovinyl ether functionalized aromatic diacid chloride with an aromatic diamine to form a reaction mixture, heating to a temperature between 180-240° C. followed by heating to 250-300° C., and, extracting volatiles by subjecting said mixture to evacuation;
- wherein the fluorovinyl ether functionalized aromatic diacid chloride is represented by the structure (III),
- wherein,
- Ar represents a benzene or naphthalene radical;
- each R is independently H, C1-C10 alkyl, C5-C15 aryl, C6-C20 arylalkyl;
- OH, or a radical represented by the structure (II)
- with the proviso that only one R can be OH or the radical represented by the structure (II);
- X is O or CF2;
- Z is H, Cl, or Br;
- a=0 or 1;
- and,
- Q is represented by the structure (Ia)
- wherein q=0-10;
- Y is O or CF2;
- Rf1 is (CF2)n, wherein n is 0-10;
- and,
- Rf2 is (CF2)p, wherein p is 0-10, with the proviso that when p is 0, Y is CF2.
In one embodiment of the process hereof, each R is H.
In one embodiment of the process hereof, one R is reperesented by the structure (II) and the remaining two Rs are each H.
In one embodiment of the process hereof, X is O.
In an alternative embodiment, X is CF2.
In one embodiment of the process hereof, Y is O.
In an alternative embodiment, Y is CF2.
In a further embodiment, Z is Cl.
In an alternative embodiment one R is represented by the structure (II), one Z is H, and one Z is Cl.
In one embodiment of the process hereof, Rf1 is CF2.
In one embodiment of the process hereof, Rf2 is CF2.
In one embodiment of the process hereof, p=0 and Y is CF2.
In one embodiment of the process hereof, the aromatic diamine is 1,4-diaminobenzene, Ar is a benzene radical, each R is H, Z is Cl, X is O, Y is O, Rf1 is CF2, and Rf2 is perfluoropropenyl, and q=1.
In another embodiment the reaction mixture further comprises an aromatic diacid chloride represented by the structure (VI)
- wherein Ar is an aromatic radical;
- each R is independently H or C1-C10 alkyl.
In a further embodiment, each R is H.
In one embodiment Ar is a benzene radical.
Dependencies are inferred from the claim text.