Fluorinated polymers and methods for their preparation

Details Fluorinated polymers and methods for their preparation Fluorinated polymers and methods for their preparation

1999-12-02

2002-08-13

Lipman, Bernard (Department: 1713)

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

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S332300, C525S359100, C525S359500

Reexamination Certificate

active

06433101

ABSTRACT:

BACKGROUND
The incorporation of fluorine into synthetic and biologically relevant macromolecules leads to materials with unique properties such as low surface energies, low dielectric constants, and resistance to harsh chemical environments. Because of these characteristics, fluorinated materials are used in contexts where chemical resistance or other special surface characteristics is desired (e.g. chemical resistant coatings, non-stick coatings, non-corrosive materials, anti-fouling coatings, and interlayer dielectrics).
As polymers have become increasingly important in the commercial context, methods for incorporating fluorine into polymeric materials have been investigated. These efforts can be categorized into either post-polymerization processing or the direct polymerization of fluorine-containing monomers. Post-polymerization fluorination routes are inherently limited to polymers that include accessible reaction sites. Moreover, available post-polymerization fluorination methods tend to be chemically aggressive (e.g. treatment with F
2
, SF
6
under electrical discharge, BF
3
—Et
2
O, SF
6
/HF, fluorinated peroxides, and HF electrochemically) and typically result in low product yield, loss of pendant functionality, degradation of the polymeric molecular weight, and unproductive cross-linking reactions. Because of these difficulties, most fluorinated polymers are prepared by the polymerization of fluorine-containing monomers. Unfortunately, this route can be exorbitantly expensive and thus not generally viable for most commercial contexts.
Therefore, a need exists for a simple, low cost method of preparing fluorinated polymers and polymeric products.
SUMMARY
The present invention relates to fluorinated polymeric products and methods of making the same. More particularly, the present invention relates to fluorinated poly-dicyclopentadiene (“poly-DCPD”) and methods for making the same. In general, the inventive polymers are produced by the reaction of a source of difluorocarbene (:CF
2
) and a polymer product formed by the ring opening metathesis polymerization (“ROMP”) of a cyclic olefin. The fluorination reaction of the ROMP polymer product may optionally include a radical inhibitor. The difluorocarbene quantitatively adds to the population of double bonds that are inherently found in ROMP-derived polymers. As a result, post-polymerization fluorination provides synergistic benefits to the physical characteristics of ROMP polymers by removing reactive surface sites while at the same time incorporating fluorine atoms therein.


REFERENCES:
patent: 3933768 (1976-01-01), Yukuta et al.
patent: 5069943 (1991-12-01), Hara et al.
Yu, et al. “A New Class of Fluorinated Polymers by a Mild, Selective, and Quantitative Fluorination.” Journal of the American Chemical Society, vol. 120, No. 27, pp. 6830-6831.

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