# US 10,308,898 B2 · Method of imparting water repellency with non-fluorinated laundry treatment compositions

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- Number: US 10,308,898 B2
- Document ID: US10308898B2
- Status: Granted
- Kind: B2
- Application number: 14/851,484
- Filed: 2015-09-11
- Published: 2016-03-31
- Granted: 2019-06-04
- Earliest claimed: 2014-09-26
- Assignees: The Chemours Company Fc, LLC
- Applicants: The Chemours Company Fc LLC
- Inventors: John Christopher Sworen; Gerald Oronde Brown; Sara Lyons; Ewa Kohler
- Web page: https://patentgrep.com/patent/US10308898B2

## CPC

- C11D 3/323: {urea or derivatives thereof}
- C09D 175/06: from polyesters
- C09D 175/08: from polyethers
- C11D 3/0005: {Other compounding ingredients characterised by their effect}
- C11D 3/0036: {Soil deposition preventing compositions; Antiredeposition agents}
- C11D 3/32: Amides; Substituted amides
- C11D 3/349: {additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea}
- C11D 3/3726: {Polyurethanes}
- D06M 13/144: Alcohols; Metal alcoholates (D06M13/11 takes precedence)
- D06M 15/564: Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M 15/568: Reaction products of isocyanates with polyethers
- D06M 15/572: Reaction products of isocyanates with polyesters or polyesteramides
- C08G 18/281: {Monocarboxylic acid compounds}
- C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds}
- C08G 18/284: {Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids}
- C08G 18/3221: {hydroxylated esters of carboxylic acids other than higher fatty acids}
- C08G 18/36: Hydroxylated esters of higher fatty acids
- C08G 18/706: {the liquid medium being water}
- C08G 18/73: acyclic
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/7831: {containing biuret groups}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C11D 3/3454: {containing sulfone groups, e.g. vinyl sulfones}
- D06M 2200/12: Hydrophobic properties
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention discloses a method of imparting water repellency and optionally stain release to fibrous substrates by contacting a fibrous substrate with a non-fluorinated laundry treatment composition inside a laundry machine. The laundry treatment composition contains a hydrophobic organic urethane compound having a urethane linkage and the residue of a substituted cyclic or acyclic sugar alcohol. Laundry additive compositions containing a first laundry treatment composition, having a hydrophobic organic urethane compound, and a second laundry treatment composition are also included.

## Claims

### Claim 1

A method of imparting water repellency and optionally stain release to fibrous substrates comprising contacting a fibrous substrate with a laundry treatment composition inside a laundry machine,
wherein the laundry treatment composition comprises a hydrophobic compound having at least one linkage of Formula I:
—NHC(O)—X— (I)
wherein
X is selected from Formulas (IIa) or (IIb):
wherein each R is independently a direct bond to NHC(O) of Formula I; —H; —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)CH2O)mR2;
or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1;
each n is independently 0 to 20;
each m is independently 0 to 20;
m+n is greater than 0;
r is 1 to 3;
a is 0 or 1;
p is independently 0 to 2;
provided that a is 0 when r is 3;
each R1 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond;
each R2 is independently —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond;
or mixtures thereof,
provided when X is Formula (IIa), then at least one R is a direct bond to NHC(O) of Formula 1; and at least two R groups are a —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)mR2; or —(CH2CH2O)n(CH(CH3 )CH2O)mC(O)R1;
each R4 is independently a direct bond to NHC(O) of Formula I; —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or combinations thereof;
—(CH2CH2O)n(CH(CH3)CH2O)mR2; or
—(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1; and
provided when X is Formula (IIb), then at least one R or R4 is a direct bond to NHC(O) of Formula 1; and at least two of R or R4 are a linear or branched alkyl group optionally comprising at least 1 unsaturated bond, or combinations thereof; —(CH2CH2O)n(CH(CH3)CH2O)mR2; or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1.

### Claim 2 (depends on 1)

The method of claim 1 wherein X is 100% bio-based derived.

### Claim 3 (depends on 1)

The method of claim 1, wherein the hydrophobic compound further comprises at least one moiety Q to form Formula (I′):
—Q—NHC(O)—X— (I′)
where Q is a monovalent, divalent, or polyvalent moiety selected from linear or branched, cyclic or acyclic, alkylene groups optionally containing at least one group selected from alkoxy, phenyl, siloxane, urethane, urea, biuret, uretdione, cyclized isocyanate, allophanate, or isocyanurate.

### Claim 4 (depends on 1)

The method of claim 1, wherein the hydrophobic compound further comprises at least one linkage selected from Formulas (IVa), (IVb), (IVc), or mixtures thereof:
R6—D (IVa),
R15—(OCH2CH(OR16)CH2)z—OR17 (IVb),
—NH—C(O)—NH—X (IVc)
wherein D is selected from —N(R12)—C(O)—NH—, —OC(O)NH—, —C(O)NH—, —SC(O)NH—, —O—(CH2CH2O)s(CH(CH3)CH2O)t—C(O)NH—, or —[C(O)]—O—(CH2CH2O)s(CH(CH3)CH2O)t—C(O)NH—;
X is defined as above;
R6 is selected from a —C1 to C30 linear or branched alkyl optionally comprising at least one unsaturated group, a hydroxyl- or urethane-functional C1 to C30 linear or branched alkyl, a hydroxyl- or urethane-functional linear or branched C1 to C30 polyether, a hydroxyl- or urethane-functional linear or branched polyester having a polyester polymer backbone, a hydroxyl- or urethane-functional linear or branched organosiloxane, an amine- or urea-functional linear or branched organosiloxane, a thiol- or thiocarbonate functional C1 to C30 linear or branched alkyl, an amine- or urea-functional C1 to C30 linear or branched alkyl,
wherein
R7, R8, and R9 are each independently, —H, —C1 to C6 alkyl, or combinations thereof;
R10 is a divalent alkyl group of 1 to 20 carbons;
R12 is —H or a monovalent C1 to C6 alkyl group;
R15, R16, and R17 are each independently a —H; —C(O)NH—, —R18; —C(O)R18 provided that at least one R15, R16, or R17 is a —C(O)NH—;
R18 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond;
z is 1 to 15;
Y is Cl;
s is an integer of 0 to 50;
t is an integer of 0 to 50; and
s+t is greater than 0.

### Claim 5 (depends on 1)

The method of claim 1 wherein X is selected from Formula (IIa) to be Formula (IIa′):
wherein R is further limited to independently a direct bond to NHC(O), —H; —R1; or —C(O)R1.

### Claim 6 (depends on 1)

The method of claim 1 wherein X is selected from Formula (IIa) to be Formula (IIa′):
wherein R is further limited to independently a direct bond to NHC(O), —H; —(CH2CH2O)n(CH(CH3)CH2O)mR2; or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1.

### Claim 7 (depends on 1)

The method of claim 1 wherein X is selected from Formula (IIb).

### Claim 8 (depends on 1)

The method of claim 1, where the laundry treatment composition further comprises a wax.

### Claim 9 (depends on 8)

The method of claim 8, where the wax is selected from beeswax; microcrystalline wax; oxidized microcrystalline wax; paraffin wax; montan wax; ozokerite wax; carnauba wax; candililla wax; palm wax; whale wax; lanolin; sugar cane wax; sugar esters; polyolefin wax; mono-, di, or tri-glyceride esters; fatty acid ester waxes; or blends thereof.

### Claim 10 (depends on 1)

The method of claim 1 wherein the contacting step occurs during a laundry machine wash cycle or rinse cycle.

### Claim 11 (depends on 1)

The method of claim 1 wherein the fibrous substrate is contacted prior to starting a laundry machine wash cycle or rinse cycle.

### Claim 12 (depends on 1)

The method of claim 1 further comprising a step of curing the hydrophobic compound with heat.

### Claim 13 (depends on 12)

The method of claim 12, where the step of curing is completed by machine drying in a dryer, ironing, steaming, blow drying, drying under a heat lamp, or drying near a radiative source of heat.

### Claim 14 (depends on 1)

A substrate treated according to the method of claim 1.