Stock material or miscellaneous articles – Composite – Of fluorinated addition polymer from unsaturated monomers
Utility Patent
1998-08-19
2001-01-02
Chen, Vivian (Department: 1773)
Stock material or miscellaneous articles
Composite
Of fluorinated addition polymer from unsaturated monomers
C525S157000, C525S158000, C525S160000, C525S165000, C525S176000, C525S178000, C525S187000, C525S199000, C525S200000, C525S221000, C525S222000
Utility Patent
active
06168866
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to fluorochemical compounds and compositions for use in providing repellent properties to a substrate material. In another aspect, this invention relates to fluorochemical compounds that contain moieties derived from amino resins. This invention also relates to fluorochemical compounds that impart properties such as soil- and abrasion-resistance when applied to substrate materials. In still another aspect, this invention relates to substrates that are treated with fluorochemical compounds.
BACKGROUND OF THE INVENTION
Organofluorine compounds or fluorochemicals are substances containing portions that are fluorocarbon in nature and have properties such as hydrophobicity, oleophobicity, and chemically inertness, and portions that are organic or hydrocarbon in nature and which may be chemically reactive in organic reactions. Some fluorochemicals are familiar to the general public, such as SCOTCHGARD brand carpet protector, which imparts oil and water repellency and stain- and soil-resistance to carpet. Other fluorochemicals have other industrial uses, such as reducing the surface tension of liquids, reducing evaporation and inflammability of volatile organic liquids, and improving the leveling of organic polymer coatings.
The utility of fluorochemicals as surface-active agents and surface-treating agents is due in large part to the extremely low free-surface energy of C
6
-C
12
fluorocarbon groups, according to H. C. Fielding, “Organofluorine Compounds and Their Applications,” R. E. Banks, Ed., Society of Chemical Industry at p. 214 (1979). Generally, the fluorochemicals described above are those which have carbon-bonded fluorine in the form of a monovalent fluoroaliphatic radicals such as a perfluoroalkyl groups, such as C
n
F
2n+1
, where n is at least 3 and the terminal group is trifluoromethyl.
SUMMARY OF THE INVENTION
The invention provides a curable fluorine-containing coating composition comprising (i) an amino resin, (ii) an addition fluorocopolymer and (iii) a hardening agent capable of crosslinking with said amino resin at elevated temperature.
The invention also provides a method of preparing a coated substrate comprising the steps of: (a) coating at least part of one surface of a substrate with the curable fluorine-containing coating composition comprising: (i) an addition fluorocopolymer, (ii) amino resin, and (iii) hardening agent; and (b) curing the coating until the desired level of cure is achieved This invention also provides coated substrates prepared in accordance with the aforementioned method.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION
The fluorocopolymer contains at least one, and preferably more than one, functional group that is capable of reacting or crosslinking with the amino resin (described in more detail below) at the cure conditions of the fluorine-containing coating composition.
Typically, such copolymers comprise interpolymerized units derived from fluorinated monomers, which may or may not contain moieties that are reactive with amino resins, and nonfluorinated amino resin crosslinking monomers (non-fluorinated monomers) each of which contains at least one moiety that is reactive with the amino resin at the cure conditions of the fluorine-containing coating composition. Generally the fluorocopolymer comprises a major amount of units derived from fluorinated monomers, relative to the amount of units derived from the nonfluorinated amino resin crosslinking monomers.
The fluorocopolymer contains a plurality of fluorocarbon groups each of which contains at least 3 carbon atoms. Preferably, the fluorocarbon groups are fluoroaliphatic groups and the average number of fluoroaliphatic groups in the fluorocopolymer is 2 to about 50. Most preferably, the average number of fluoroaliphatic groups in the fluorocopolymer is 20 to about 50. Generally, the fluorocopolymer contains from about 30 to about 80 weight percent fluorinated monomer, preferably from about 50 to about 75 weight percent based on the total weight of the fluorocopolymer. Preferably, essentially all of the fluorine in the fluorocopolymer is located in fluoroaliphatic groups.
Although the fluorinated monomer may contain moieties that can react with the amino resin at the coating composition cure conditions, such monomers are not generally used in the practice of the invention because it is preferable to react the fluorocopolymer to the amino resin through the functional groups on interpolymerized units derived from the amino resin crosslinking monomer or through the functional groups, if any, incorporated into the fluorocopolymer through the chain transfer agent (described in more detail below).
The fluorinated monomers useful in the invention are addition copolymerizable with the amino resin crosslinking monomer and any optional comonomer (described in more detail below) and contain at least one fluorocarbon group generally having at least three carbon atoms. Many such monomers and their methods of preparation are known and disclosed, e.g., in U.S. Pat. Nos. 2,803,615 (Ahlbrecht et al.) and 2,841,573 (Ahlbrecht et al.) which disclosures are incorporated herein by reference.
Examples of fluorinated monomers useful in this invention include the general classes of fluorochemical olefins such as acrylates, methacrylates, vinyl ethers, and allyl compounds containing fluorinated sulfonamido groups; acrylates or methacrylates derived from fluorochemical telomer alcohols or fluorochemical thiols, and the like. Preferred fluorinated monomers include N-methyl perfluorooctanesulfonamidoethyl acrylate, N-methyl perfluorooctanesulfonamidoethyl methacrylate, N-ethyl perfluorooctanesulfonamidoethyl acrylate, N-methylperfluorohexylsulfonamidoethyl acrylate, the reaction product of isocyanatoethylmethacrylate and N-methylperfluorooctanesulfonamidoethyl alcohol, perfluorooctyl acrylate, N-methyl perfluorooctanesulfonamidoethyl vinyl ether, and C
8
F
17
SO
2
NHCH
2
CH═CH
2
, and others such as perfluorocyclohexyl acrylate, and tetrameric hexafluoropropylene oxide dihydroacrylate. A single type of fluorinated monomer or mixtures of various fluorinated monomers may be used to make the fluorocopolymer.
The amino resin crosslinking monomer can be any compound having a free radically polymerizable group capable of copolymerizing with the fluorinated monomer and, any optional comonomer, and a functional group capable of reacting with the amino resin at the coating cure conditions. Examples of such functional groups include carboxyl groups, amines, amides, epoxides, hydroxy groups and silane groups.
Generally the fluorocopolymer will comprise a minor amount of units derived from the amino resin crosslinking monomer. Preferably the fluorocopolymer contains from 5 to about 50 weight percent crosslinking monomer and most preferably 20 to 40 weight percent, based on the total weight of the fluorocopolymer.
Examples of amino resin crosslinking monomers include: N-methylol acrylamide; N-methylol methacrylamide; aziridinyl acrylate and methacrylate; diacetone acrylamide and methacrylamide; methylolated diacetone acrylamide and methacrylamide; 2-hydroxy-3-chloropropyl acrylate and methacrylate; hydroxy (C
2
to C
4
) alkyl acrylates and methacrylates; maleic anhydride; allyl alcohol; allyl glycolate; isobutenediol; allyloxyethanol; o-allyl phenol; divinyl carbinol; glycerol &agr;-allylether, acrylamide; methacrylamide; maleamide; maleimide; N-cyanoethyl acrylamide; N-isopropyl acrylamide; glyoxal bis-acrylamide; acrylic acid, methacrylic acid, and metal salts thereof; vinylsulfonic and styrene p-sulfonic acids and their metal salts; 3-aminocrotonitrile; monoallylamine; vinylpyridines; n-vinylpyrrolidone; 2-acrylamido-2-methylpropanesulfonic acid (AMPS) and its salts; vinyl azlactones; glycidylacrylate and methacrylate; allyl glycidyl ether; acrolein; methylaminoethyl acrylate and methacrylate; N-tert-butylaminoethyl methacrylate; allyl methacrylate; diallyl maleate; vinyltriethoxysilane; vinyltrichlorosilane; and the like.
A preferred class of a
3M Innovative Properties Company
Chen Vivian
Kokko Kent S.
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