Stock material or miscellaneous articles – Coated or structually defined flake – particle – cell – strand,... – Rod – strand – filament or fiber
Reexamination Certificate
1999-09-24
2002-05-07
Thibodeau, Paul (Department: 1773)
Stock material or miscellaneous articles
Coated or structually defined flake, particle, cell, strand,...
Rod, strand, filament or fiber
C428S393000, C428S395000, C428S421000, C428S480000, C428S537500, C442S088000, C442S082000, C442S092000, C442S094000, C526S242000, C526S243000, C526S247000, C526S248000, C560S250000, C564S153000
Reexamination Certificate
active
06383633
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to fluorochemical compositions for the treatment of substrates, in particular fibrous substrates such as textiles to impart stain release properties to those substrates.
BACKGROUND OF THE INVENTION
Fluorochemical compositions for the treatment of substrates such as leather, textiles and paper, are well known and are used to impart various properties to the substrate such as water and/or oil repellency, waterproofness, anti-staining, and soil-resistance. For example, U.S. Pat. No. 5,100,954 discloses a soil resisting agent containing, as an effective component, a copolymer of (I) a fluorine-containing urethane compound containing a (meth)acryloyl group or an allyl group, and a polyfluoroalkyl group, obtained by reacting (a) a polyfunctional isocyanate having at least trifunctionality, (b) a hydroxy compound containing a (meth)acryloyl group or an allyl group, and (c) a hydroxy compound having a polyfluoroalkyl group, and (II) a copolymerizable compound other than said fluorine-containing urethane compound.
U.S. Pat. No. 4,920,190 describes certain fluorochemical compositions that are based on polymers of fluorinated acrylic monomers in which a perfluoroalkyl group is linked by 2,4-toluenediisocyanate to an acrylate or methacrylate. Amongst useful acrylates and methacrylates are mentioned mono-(meth)acrylates of polyalkyleneglycols. The fluorochemical compositions are said to be suitable as water or oil-repellents for various substrates and in particular leather. U.S. Pat. No. 4,778,915 describes certain polymers of fluorinated acrylic monomers that contain a perfluoroalkyl group linked to an acrylate or methacrylate by a di-isocyanate, for use as water or oil repellents.
Fluorochemical compositions are also used to facilitate stain or soil release from a substrate such as, for example, a fabric. Routine treatments of fabrics with various modifying additives such as softeners, stiffeners, and lubricants, to impart desired properties to a commercial fabric typically increase the oleophilicity of the fabric, thereby significantly increasing its tendency to accept oily stains and reducing its ability to release such stains after laundering. Fluorochemical compositions based on a mixture of a fluorinated compound and a non-fluorinated hydrophilic compound or a chemical “hybrid” compound containing fluorochemical oleophobic segments (“F”) and non-fluorinated hydrophilic segments (“H”) 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 as well as facilitate soil release during laundering.
For example, U.S. Pat. No. 4,859,754 describes certain water and oil repellent treatments having desoiling properties that are composed of a polyfluorinated group containing copolymer obtained by copolymerizing a first and second monomer wherein the first monomer contains a polyfluorinated group and the second monomer is an amphiphatic monomer having a hydrophilic moiety and a lipophilic moiety.
U.S. Pat. No. 3,920,614 describes certain high soil release oil-and water repellent copolymers prepared by copolymerization of at least 25% by weight of a fluoroalkyl monomer and 5 to 50% by weight of poly(oxyethylene) acrylate or methacrylate.
U.S. Pat. No. 4,695,488 describes certain polymers obtained by homopolymerization of poly(oxyalkylene) monomers terminated by fluorinated groups. According to the disclosure, a composition based on this polymer could impart stainproofing properties with good durability to a substrate such as plastics, fabric and paper.
Despite the many fluorochemical compositions known to impart stain release properties to a substrate, there continues to be a desire for fluorochemical compositions with improved properties. Desirable properties include easy cleanability of substrates based on natural fibers such as cotton and blends of cotton and polyester, particularly with respect to oil type stains (dirty motor oil, vegetable oil) and water based stains (tea, coffee, wine); low manufacturing cost; high storage stability; easy emulsifiability and high performance even if applied in low quantities. It is also desired that the fluorochemical compositions provide good stain release properties and oil and/or water repellency properties to the substrate.
SUMMARY OF THE INVENTION
The present invention provides a method of treatment of a substrate comprising the step of contacting said substrate with a fluorochemical composition comprising a polymer derived from polymerization of monomer corresponding to the following general formula (I):
wherein:
R
f
is selected from the group consisting of perfluorinated or partially fluorinated aliphatic groups;
L
1
and L
2
are each independently an organic divalent linking group and they may be the same or different;
L
3
represents an organic linking group with a valence of n+1;
t is 0 or 1;
n is an integer of 2 to 20;
A
1
and A
2
are each independently selected from the group consisting of divalent residues obtained by removing 2 —NCO groups from a corresponding diisocyanate;
X
1
is selected from the group consisting of O, NH and S;
X
2
is selected from the group consisting of O, NH and S;
B
1
represents a hydrophilic residue obtained by removing the groups HX
1
and HX
2
from a compound HX
1
—B
1
—X
2
H that comprises a poly(oxyalkylene) group;
G represents a free radical polymerizable group; and
s is 0 or 1 with the proviso that when s is 0, L
2
represents a hydrophilic segment comprising a poly(oxyalkylene) group or said polymer is derived from a copolymerization of a monomer according to formula (I) and a poly(oxyalkylene) group containing monomer.
Also provided is a fluorochemical composition comprising a polymer derived from a polymerization of a monomer corresponding to the following general formula (I):
wherein:
R
f
is selected from the group consisting of perfluorinated or partially fluorinated aliphatic groups;
L
1
and L
2
are each independently selected from the group consisting of organic divalent linking groups;
L
3
is an organic linking group with a valence of n+1;
t is 0 or 1;
n is an integer of 2 to 20;
A
1
and A
2
are each independently selected from the group consisting of divalent residues obtained by removing twp —NCO groups from a corresponding diisocyanate;
X
1
is selected from the group consisting of O, NH and S;
X
2
is selected from the group consisting of O, NH and S;
B
1
represents a hydrophilic segment comprising a poly(oxyalkylene) group;
G represents a free radical polymerizable group; and
s is 0 or 1 with the proviso that when s is 0, L
2
represents a hydrophilic segment comprising a poly(oxyalkylene) group or said polymer is derived from a copolymerization of a monomer according to formula (I) and a poly(oxyalkylene) group containing monomer.
There is further provided a use of the fluorochemical composition to provide good stain release properties to a substrate and a substrate comprising on at least one of its surfaces, the fluorochemical composition.
Further provided are a monomer according to formula (I) above and a monomer composition including a monomer according to formula (I) and a poly(oxyalkylene)-containing monomer.
DETAILED DESCRIPTION OF THE INVENTION
The polymer used in the fluorochemical composition is derived from at least one monomer according to formula (I) above. If the monomer according to formula (I) includes a poly(oxyalkylene) group, i.e. s is 1, and/or L
2
contains a polyoxyalkylene a homopolymer of the monomer of formula (I) can be used as well as a copolymer of that monomer. The polyoxyalkylene group is typically of a sufficient length such that sufficient wetting of the substrates occurs during laundering thereby facilitating removal of stain. Preferably, the number of oxyalkylene moieties in the poly(oxyalkylene) group is between about 18 and 275 or between about 20 and 190 and more preferably between about 23 and 95. In case the monomer according to formula (I) does not include the
Allewaert Kathy E. M. L. A.
Vander Elst Pierre J.
3M Innovative Properties Company
Kokko Kent S.
Thibodeau Paul
Zacharia Ramsey
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