Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-06-28
2004-03-23
Yoon, Tae H. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S544000, C524S806000, C526S244000, C526S247000, C526S250000, C528S042000
Reexamination Certificate
active
06710123
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to fluoropolymers and uses for these fluoropolymers In particular, the present invention relates to fluoropolymers containing organo-silane functional groups. The present invention further relates to methods of making the fluoropolymers.
Various attempts have been made to make fluorine-containing polymers for a variety of reasons. Fluoropolymers are traditionally used for applications which require special properties such as low surface energy, high resistance to chemical attack, low dielectric loss, or extreme requirements on aging resistance. However, sometimes these unusual properties are problems themselves in the use of fluoropolymers. For example, the lack of functional groups to promote: adhesion to substrates, to facilitate cross-linking, to provide sites for subsequent chemical modification, to introduce ion-exchange capacity or ionic conductivity severely limits the application of ordinary fluoropolymers. Thus, fluorinated polymers with modified properties, such as reactive functional groups which can be modified, are constantly being sought. However, to the knowledge of the present inventors, fluorine-containing polymers having an intact organo-silane moiety which can be reactive has yet to be made in aqueous media.
For example, Buning et al. [Chemical Abstract Number 72:101262 and Die Ang. Mak. Chemie 13 (1970) pp. 89-96] describes, based on the English abstract the co-polymerization of vinyl (ti-tert-butoxy) silane in emulsion or suspension with vinyl chloride or styrene in the presence of dilauroyl peroxide or Bz
2
O
2
to result in uncross-linked copolymers. The abstract further reports that when vinyl (trimethoxy)-silane was used instead of vinyl (tri-tert-butoxy) silane, an insoluble, crosslinked copolymer was obtained containing poly(vinyl chloride). There is no mention in the English abstract of fluorine containing polymers nor is there any appreciation of the use of pH controllers during suspension polymerization.
Piotrowski et al. [Chemical Abstract Number 102:167808] relates to CH
2
:CF
2
polymers which are grafted with alkenylalkoxy silanes in the presence of a peroxide to result in resins cross-linkable by silanol condensation catalysts and moisture. There is no mention of an aqueous medium being used in the reaction and specific hydrolizable organo-silane moieties which are not hindered, are grafted to the molten poly(vinylidene fluoride) in the presence of a peroxide initiator.
European Patent Application No. 0 736 583 primarily relates to aqueous dispersions of a fluorine-containing polymer which are formed by post-mixing organo-silicon compounds in the fluorine-containing polymer-dispersed aqueous composition. A co-polymerization involving an organosilane is discussed, but used as an intermediate product. Thus, according to this publication, the organo-silicon compounds are mixed with the fluoropolymer dispersion after the polymerization to form the fluoropolymer dispersion.
In addition, U.S. Pat. No. 5,621,033 to Chen et al. relates to curable compositions containing a water dispersible curable polymer containing a sterically hindered alkoxylated silane group, a water dispersible or water soluble, hydrolytically stable organometallic catalyst, and water. Chen et al. states that these compositions are useful as adhesives, sealants, and paints. Chen et al. further reports that the compositions have improved properties including solvent resistance, adhesion, hardness, abrasion resistance, and mar resistance. Chen et al. does not mention the use of fluoropolymers and requires the presence of a hydrolytically stable organometallic catalyst. U.S. Pat. No. 5,686,523 to Chen et al is similar but does not require a hydrolytically stable organometallic catalyst.
Previous fluoropolymers, while having beneficial properties with respect to chemical resistance, high temperature stability, high tensile strength, and/or low refractive index, have the disadvantage that subsequent modifications such as post cross-linking or post chemical modification were not feasible due to the possible compromising of these beneficial properties. Accordingly, there is a need to provide fluoropolymers which can be advantageously cross-linked and/or chemically modified without substantially affecting the beneficial properties typically associated with fluoropolymers.
SUMMARY OF THE INVENTION
A feature of the present invention is to provide fluoropolymers which are cross-linkable and/or can be chemically modified without substantially affecting the beneficial properties typically associated with fluoropolymers such as chemical resistance, high temperature stability, high tensile strength, and/or low refractive indices.
Another feature of the present invention is to provide fluoropolymers which are capable of being chemically bonded to a variety of substrates.
Another feature of the present invention is to provide fluoropolymers which can be functionalized.
Another feature of the present invention is to provide methods of making these types of fluoropolymers.
Additional features and advantages of the present invention will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned by practice of the present invention. The features and other advantages of the present invention will be realized and obtained by the description set for herein including the elements in combinations particularly pointed out in the written description and pending claims.
To achieve these and other advantages and in accordance with the purposes of the present invention, as embodied and broadly described herein, the present invention relates to a fluoropolymer comprising a polymer reaction product of a) at least one first alkylene co-monomer containing at least one fluorine atom; b) optionally at least one monomer selected from 1) at least one second alkylene containing at least one fluorine atom; 2) at least one alkyl alkenyl ether containing at least one fluorine atom; 3) at east one aliphatic or cyclic ketone containing at least one fluorinated alpha-alpha position; or 4) non-fluorinated alkene, alkyl alkenyl ether, or alkenyl ester; and c) at least one sterically hindered alkenyl or alkenyl ether organo-silane co-monomer with or without at least one fluorine substituent.
The present invention further relates to the fluoropolymer described above which can be cross-linked and/or can contain one or more functional groups.
The present invention also relates to a process for the production of the polymers described above by free radical polymerization techniques known in the art, such as suspension polymerization, emulsion polymerization, interfacial polymerization, solution polymerization, or non-aqueous polymerization systems, wherein one or more of liquid or super-critical carbon dioxide, liquid or super-critical SF6, liquid or super-critical fluorinated or perfluorinated hydrocarbon(s) with 1 to about 6 carbons can be used as polymerization media.
The present invention further relates to a method of making the above-described fluoropolymers and involves conducting a polymerization of the co-monomers described above for a sufficient time and at a sufficient pressure and temperature to form the fluoropolymer. Preferably, the polymerization is a free radical polymerization, and more preferably is an emulsion polymerization.
In addition, the present invention relates to the use of the fluoropolymers in a variety of applications, including, but not limited to, foamed cross-linked fluoropolymers, fluoro-elastomers, adhesives, coatings and the like. The fluoropolymers of the present invention can also be used as a membrane component as well as other applications.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide a further explanation of the present invention as claimed.
DETAILED DESCRIPTION OF THE PRESENT INVENTION
The present invention relates to fluorop
Amin-Sanayei Ramin
Granel Claude Christophe
Atofina Chemicals, Inc.
Kilyk & Bowersox, PLLC
Yoon Tae H.
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