Fluorine-containing compounds and polymers derived therefrom

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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Reexamination Certificate

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06809216

ABSTRACT:

FIELD OF INVENTION
The present invention relates generally to fluorine-containing compounds, and polymers derived therefrom, for use in compositions used for treating textile substrates. The present invention further relates to methods of making fluorine-containing compounds and polymers derived therefrom, compositions comprising the compounds and/or polymers of the present invention, methods of treating substrates, and the treated products derived therefrom.
BACKGROUND
Fluorine-containing compounds have found use in a wide range of industrial applications including, for example, textile coating applications. Because such fluorine-containing compounds, and the polymers derived therefrom, form coatings which tend to increase the water repellency, oil repellency, and/or soil resistance of substrates, they are desirable for use in treating and protecting the surfaces of such substrates.
Unfortunately, such known fluorochemicals tend to be environmentally undesirable. Many of such known chemicals tend to biodegrade, at least in part, to form compounds such as perfluorocarboxylic acids. Perfluorocarboxylic acids have long and potentially damaging lifetimes in environment. Also, such compounds are not readily metabolized in the human body and tend to bioaccumulate in the liver. Thus, ingestion or inhalation of such compounds can be detrimental to human health.
Recognizing these and other drawbacks of the related art, the present inventors have perceived a need for new fluorine-containing compounds which are not only suitable for use in a variety of applications, especially textile coatings applications, but also are environmentally desirable and have relatively low toxicity. These and other objects are achieved by the present invention as described below.
SUMMARY OF THE INVENTION
The present invention is directed to a family of fluorine-containing compounds, and polymers derived therefrom, for use in the preparation of compositions used in various coatings or textile-treatment applications. The compounds of the present invention are advantageous over fluorinated compounds used conventionally to treat textiles in that the present compositions tend to biodegrade more readily, and, upon biodegradation, tend to form compounds that are more environmentally-desirable and less toxic than conventional compounds.
Accordingly, one aspect of the present invention relates to fluorine-containing compounds. In preferred embodiments, the present invention provides fluorine-containing compounds which are described by the following formula:
CH
2
═C(R
1
)C(O)O—(Y—O)
a
—CR
2
R
3
—CF
2
CHFCF
3
  (1)
wherein: R
1
, R
2
and R
3
are independently hydrogen or lower alkyl, Y is a divalent organic moiety, and a is zero or one.
Another aspect of the present invention is a family of polymers comprising at least one repeating unit derived from the compounds of the invention. In preferred embodiments, the polymers of the present invention comprise at least one repeating unit derived from a compound of formula (1).
The compounds and polymers of the present invention are useful compositions designed to impart water repellency to a substrate. Therefore, yet another aspect of the present invention is a composition comprising a polymer of the present invention.
Yet another aspect of the present invention relates to a method for treating a substrate with a composition of the present invention comprising applying a layer of the composition of the invention onto a substrate and curing the composition on the substrate.
The inventive method produces articles of manufacture having water and soil-repellent coatings. Therefore, still another aspect of the present invention is a substrate having a water-resistant and/or soil-resistant coating produced via the method of the present invention.
The compositions comprising polymers or compounds of the present invention may be cured to form films. Therefore, another aspect of the present invention includes the films produced by curing the compositions of the present invention.


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