Coating processes – With post-treatment of coating or coating material – Heating or drying
Reexamination Certificate
1999-09-24
2002-11-26
Reddick, Judy M. (Department: 1713)
Coating processes
With post-treatment of coating or coating material
Heating or drying
C252S008620, C008S115560, C008S115640, C427S385500, C427S386000, C427S388100, C427S388400, C427S389900, C427S391000, C427S392000, C427S393000, C524S503000, C525S056000, C525S058000
Reexamination Certificate
active
06485789
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to fluorochemical compositions for the treatment of substrates, in particular fibrous substrates such as textile to impart stain release properties to those substrates.
BACKGROUND OF THE INVENTION
Certain fluorochemical compositions have been used to impart various properties, such as water and/or oil repellency, waterproofness, stain release and anti-staining to various substrates like leather, textiles and paper. For example, U.S. Pat. No. 4,563,493 describes the use of certain omega-perfluoroalkyl-1,2-epoxy-alkane copolymers as water and oil repellent treatments.
U.S. Pat. No. 4,399,077 discloses the use of certain polyoxy perfluorinated surface active oligomers in cosmetic compositions for hair to slow down the flow of sebum and the rate at which hair becomes greasy again.
EP 331307 discloses certain perfluoroalkyl polyether glycols derived from 3-perfluoroalkyl-1,2-epoxy propane. It is stated that these polyether glycols are useful for making polyurethanes in a condensation reaction with a di- or polyisocyanate.
U.S. Pat. No. 4,540,765 discloses certain fluorochemical polyurethanes that it alleges impart permanent oil and/or water repellency to inorganic and organic objects. The polyurethanes disclosed in this patent are obtained by a condensation of a fluorochemical diol and a di- or polyisocyanate.
Certain fluorochemical compositions are also used to facilitate stain release from substrates such as fabrics. Such compositions may also include various modifying additives such as softeners, stiffeners and lubricants which are added to the composition to impart desired properties to a fabric. These additives typically increase the oleophilicity of the fabric, thereby significantly increasing the fabric's tendency to accept oily stains and reducing its ability to release such stains after laundering.
An improvement to such compositions are fluorochemical treatments consisting of certain fluorinated compound and a non-fluorinated hydrophilic compound mixtures as well as treatments containing certain “chemical hybrid” fluorochemical compounds which contain fluorochemical oleophobic segments (“F”) and non-fluorinated hydrophilic segments (“H”). Such improvement treatments are known to act as stain release compositions since they provide oil repellency during normal wear and inhibit wicking or diffusion of oily soils into the fabric or fiber bundles and facilitate soil release during laundering.
U.S. Pat. No. 3,574,791 discloses certain block-copolymers consisting of F and H segments and alleges that such polymers are useful as stain-release agents. The “F” segments are substantially free of hydrophilic groups whereas the “H” segments are substantially free of fluorinated aliphatic groups. The patent teaches that this segmentation of the polymer renders it “autoadaptable”, i.e., a fabric treated with the polymer will perform as an oil and water repellent in an atmospheric environment and will become hydrophilic when laundered thereby facilitating stain removal. The patent contemplates various chemical linkages for connecting the “F” and “H” segments, and amongst them is a urethane linkage derived from the reaction of an alcohol and an isocyanate.
U.S. Pat. No. 4,046,944 discloses certain fluorochemical compositions containing block-copolymers that contain a fluorinated polyurethane segment linked to a hydrophilic polyethyleneoxide block via a urea linkage. The patent teaches that the fluorochemical composition can be used to impart stain release properties to a fabric.
U.S. Pat. No. 5,841,027 discloses certain fluorocarbamate soil-release agents. The urea linkage-containing alkoxypolyoxyalkylene fluorocarbamates are prepared by reacting (a) at least one polyisocyanate containing at least three isocyanate groups, with (b) at least one fluorochemical reagent containing one functional group having at least one hydrogen atom and at least two carbon atoms each of which is substituted with at least two fluorine atoms, (c) at least one hydrophilic, water-solvatable reagent containing a single functional group having at least one reactive hydrogen atom, and (d) at least one reagent containing one reactive hydrogen atom and, which on reaction with an isocyanate group, yields functionality which has abeyant chemical reactivity with fibrous substrates and then reacting the product with water. The patent discloses that reactants (b), (c) and (d) react with 55% to 95% of the isocyanate groups, and water reacts with the remainder.
JP-A-08-225493 discloses certain polymers derived from fluorine containing monomers and alleges such polymers are useful as stain releasing water and oil repellents. The monomers are fluorochemical acrylates or methacrylates that are prepared by first reacting, e.g., an alkyl ether of a polyglycol with a perfluoroalkyl epoxypropane and subsequently reacting the obtained alcohol with (meth)acryloyl chloride to obtain the fluorochemical monomer.
Despite the many fluorochemical compositions taught by the art to impart stain release properties to a substrate, there continues to be a desire for new fluorochemical compositions with improved properties. Properties like easy cleanability of natural fiber-based substrates (e.g., cotton and blends of cotton and polyester) are desired. In particular, it is especially desired to have treatments that will permit the easy removal of oil-type stains (like dirty motor oil and vegetable oil) and water-based stains (like tea and coffee) from such substrates. Also desired are fluorochemical compositions having low manufacturing cost, high storage stability, easy emulsifiability and high performance even if applied in low concentrations.
SUMMARY OF THE INVENTION
The present invention provides a method of treating of a substrate comprising the step of contacting the substrate with a fluorochemical composition which comprises a condensation product of a di- or tri-isocyanate and at least one polyether. The polyether being obtainable by reacting a fluorochemical substituted epoxide according to formula (I) with a compound of formula (II) or formula (III):
HX
1
—B—X
2
H (II)
(R
f
′)
k
—L
2
—X
2
H (III)
wherein:
B represents an organic residue obtained by removing the groups HX
1
and HX
2
from the compound in formula (II);
X
1
and X
2
are each independently selected from the group consisting of O, NH and S;
L
1
represents an organic divalent linking group;
L
2
represents an organic linking group having a valence of k+1;
k is an integer of 1 to 10;
R
f
and R
f
′ are each independently selected from the group consisting of perfluorinated and partially fluorinated aliphatic groups;
s is 0 or 1, and
a is 0 or 1, and preferably is 1.
Substrates treated in accordance with the invention have good stain release properties, particularly to oil stains or tea stains, so stains can be more easily removed from the treated substrate in a laundering procedure.
In another aspect, the invention provides certain fluorochemical compositions for use in the method, a process for the preparation of the fluorochemical compositions and the polyether used to prepare the fluorochemical compositions.
Detailed Description of the Invention
The condensation product used in the fluorochemical composition is prepared by reacting a di- or tri-isocyanate with certain polyether obtainable by reacting a fluorochemical substituted epoxide of formula (I) with a compound of according to formula (II) or (III). Mixtures of compounds of formula (I), (II) or (III) may also be used to practice the invention.
The molar ratio of the fluorochemical substituted epoxide to the compound according to formula (II) is preferably between about 2 and 50 and more preferably between about 5 and 20. The molar ratio of the fluorochemical substituted epoxide to the compound according to formula (III) is preferably between about 2 and 30 and more preferably between about 4 and 15. Preferably, the molecular weight of the polyethers obtainable from a reaction of a compound of formula (I) with
Allewaert Kathy E. M. L. A.
Dams Rudolf J.
Vander Elst Pierre J.
Kokko Kent S.
Reddick Judy M.
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