Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From fluorine-containing reactant
Reexamination Certificate
2001-05-14
2003-12-09
Moore, Margaret G. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From fluorine-containing reactant
C528S299000, C106S003000, C106S010000, C525S437000, C525S438000, C525S934000
Reexamination Certificate
active
06660828
ABSTRACT:
FIELD OF THE INVENTION
One or more low carbon atom fluorocarbons of usually 7 carbon atoms or less are contained on a polymer generally having polar groups. The fluorocarbons generally exist as side chains with at least 25% of the hydrogen atoms being replaced by fluorine atoms. The polymer of the present invention is found unexpectedly to be an effective wetting, or flow, or leveling agent while producing little foam.
BACKGROUND OF THE INVENTION
U.S. Pat. No. 3,859,253 to Bourat et al. relates to polyoxetanes comprising a plurality of repeating units wherein the chain oxygen atoms of each recurring unit is attached to a chain methylene group of an adjacent recurring unit with, in addition, cross-linking via the other free valencies when the polymer contains repeating units.
U.S. Pat. No. 5,068,397 to Falk et al. relates to tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R
f
—E
n
—X—CH
2
)
3
CCH
2
OH prepared from halogenated neopentyl alcohols and thiols of the formula Rf—E
n
—SH, amines of the formula R
f
—E
n
—NH—R, alcohols of the formula R
f
—E
n
—OH, and perfluoro-acids or amides. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R
f
-neopentyl alcohol containing three perfluoroalkyl hetero groups.
U.S. Pat. No. 5,674,951 to Hargis et al. relates to coating compositions which use a polyoxetane polymer having —CH
2
—O —CH
2
—R
f
side chains where R
f
is a highly fluorinated alkyl or polyether. The coating compositions use polyisocyanates to create isocyanate terminated polymers from the poly(oxetane) and from various polyols from alkylene oxides or polyester polyols. These can be reacted together to form block copolymer structures or can be linked together when the coating is crosslinked. A preferred method is to use blocked isocyanate groups. Another preferred embodiment is to use the composition as an abrasion resistant coating for glass run channels.
U.S. Pat. No. 5,807,977 to Malik et al. relates to fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxide with either 3-halomethyl-3-methyloxetane premonomers. It also relates to copolymers of oxetane and tetrahydrofuran.
U.S. Pat. No. 5,998,574 to Fishback et al. relates to a polyol composition comprising: (A) a polytetramethylene ether glycol, and (2) a difunctional active hydrogen compound-initiated polyoxyalkylene polyether polyol having a degree of unsaturation of not greater than 0.04 milliequivalents per gram of said polyether polyol.
U.S. Pat. No. 6,020,451 to Fishback et al. relates to a polyol composition comprising: (A) a polytetramethylene ether glycol, and (2) a difunctional active hydrogen compound-initiated polyoxyalkylene polyether polyol having a degree of unsaturation of not greater than 0.04 milliequivalents per gram of said polyether polyol.
U.S. Pat. No. 6,127,517 to Koike et al. relates to the polymerization of hexafluoropropene oxide (HFPO) in a polymerization initiator solution of the formula: CsCF
2
—R
f
—CF
2
OCs wherein R
f
is a perfluoroalkylene group which may have an ether bond in an aprotic polar solvent provided that the initiator solution is first treated by adding a perfluoroolefin thereto at a sufficient temperature for the removal of protonic substances, cesium fluoride and hydrogen fluoride. This simple treatment restrains chain transfer reaction, and the process is successful in producing a difunctional HFPO polymer having a high degree of polymerization while suppressing formation of a monofunctional HFPO polymer.
U.S. Pat. No. 6,168,866 to Clark relates to a curable fluorine-containing coating composition comprising: (i) an amino resin; (ii) an addition fluoropolymer comprising a copolymer of a fluorinated monomer having a fluorocarbon group of at least 3 carbons, and a non-fluorinated monomer having a crosslinking group capable of reacting with said amino resin at elevated temperatures; and (iii) a hardening agent capable of crosslinking with said amino resin at elevated temperatures.
Heretofore, non-polymeric molecules containing fluorinated and polar groups were used as wetting, or flow, or leveling agents; however, many of these materials have been shown to bioaccumulate thereby greatly limiting their utility.
SUMMARY OF INVENTION
The partial or fully fluorinated short carbon atom side chain containing polymers of the present invention unexpectedly have good wetting, or flow, or leveling properties. The types of polymers are numerous and include polymers derived from cyclic ethers, poly(acrylates), poly(methacrylates), hydroxyl terminated poly(acrylates) or poly(methacrylates), polyolefins, polymers derived from vinyl substituted aromatic monomers such as styrene, polyesters, polyurethanes, polyamides, polyimides, polysiloxanes, and the like with polyoxetane being preferred. The polymers have at least one group that is polar which can be an anionic group, a cationic group, or a nonionic group. The polymer can also be amphoteric containing both anionic and cationic groups.
Furthermore, the polymers of the present invention can be caused to react with another monomer or with another polymer to impart effective wetting, or flow, or leveling properties to a coating prepared therefrom. Alternatively, the polymers of the present invention can be used as an additive with other polymers, copolymers, compositions, etc. to provide improved wetting, or flow, or leveling properties. Compared to molecules used typically as wetting, or flow, or leveling agents, the materials set forth in the present invention have relatively little propensity to cause foaming. This is often a desirable attribute of a wetting, flow, or leveling agent.
DETAILED DESCRIPTION OF THE INVENTION
The fluorinated short carbon chain compounds of the present invention are generally located on polymers as side chains thereof. These polymers, which contain one or more polar groups are generally dispersible or soluble in water and various hydrocarbon solvents and unexpectedly function as wetting, or flow, or leveling agents providing good optical properties to a coating such as high gloss and good distinctness of image, and thus can be blended with a wide variety of solutions, waxes, polishes, coatings, blends and the like.
Polymers of the present invention contain fluorinated carbon groups generally represented by the formula R
f
. The R
f
groups can be part of the monomer which is reacted to form the polymer or they can be reacted with an already formed polymer. Alternatively, a polymer containing a R
f
group such as a fluorinated polyoxetane can be reacted with a polymer or monomer to form a copolymer which thus contains a plurality of pendant short chained R
f
groups thereon. Examples of a non-R
f
containing copolymer portion are various cyclic ethers, various polyesters, various acrylic polymers, various polysiloxanes, various polyamides, various polyurethanes, and various polymers made from vinyl substituted aromatic monomers.
A wide variety of fluorine-containing polymers can be utilized as generally set forth by the following description:
The polymer can be comprised of repeat units (with repeat units being greater than or equal to 2) of a variety of monomers including cyclic ethers, acrylates, olefins and vinyl moieties. The most preferred monomers are cyclic ethers (including fluorinated cyclic ethers such as those based on hexafluoropropylene oxide) such as oxetanes, and oxiranes. Other preferred monomers include acrylates, vinyls including styrenics, silanes, and siloxanes, as well as polyester forming monomers, polyamide forming monomers, polyimide forming monomers, and polyurethane forming monomers. Th
Cartwright Brian T.
Jialanella Gary L.
Kausch Charles M.
Leising Jane E.
Medsker Robert E.
Burleson David G.
Hudak Daniel J.
Moore Margaret G.
Omnova Solutions Inc.
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