# US 5,348,769 A · Fluorosilicone compositions as wash durable soil and stain repellent finishes

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- Number: US 5,348,769 A
- Document ID: US5348769A
- Status: Granted
- Kind: A
- Application number: 08/040,872
- Filed: 1993-03-31
- Granted: 1994-09-20
- Earliest claimed: 1993-03-31
- Assignees: OSi Specialties, Inc.
- Inventors: Ronald J. Gambale; Bruce C. J. Barbera
- Web page: https://patentgrep.com/patent/US5348769A

## CPC

- D06M 15/657: containing fluorine
- Y10T 442/2287: Fluorocarbon containing
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

This invention provides a method of using perfluoroalkyl hydroxyalkyl siloxanes to impart wash durable soil and stain repellency to a fibrous substrate such as cotton and cotton/polyester fabric.

## Claims

### Claim 1

A method for imparting wash durable soil and stain repellency to a fibrous substrate, which method comprises contacting a fibrous substrate with durable press resin, a catalyst, and a perfluoroalkyl hydroxyalkyl siloxane selected from the group consisting of
(i) linear siloxanes having the general formula: ##STR6## wherein a=0 to 100;
b=1 to 100;
c=1 to 100; and
(ii) cyclic siloxanes having the general formula: ##STR7## wherein d=0 to 10;
e=1 to 10;
f=1 to 10
with the proviso that d+e+f is greater than or equal to 3;
and wherein in the formulae
each R.sup.1 and R.sup.2 is selected from the group consisting of hydrogen, hydroxy, and an alkyl group having 1 to 6 carbon atoms;
R.sup.3 is selected from the group consisting of (CH.sub.2).sub.y CHOHCHR.sup.2 and (CH.sub.2).sub.g Q.sub.j, wherein Q is selected from the group consisting of --NH--, --S--, and --O--; i is 0 or 1; y is 2 to 4; and g is 1 to 6;
R.sup.4 is selected from the group consisting of CH.sub.3, (CH.sub.2).sub.m CHR.sup.1 (CH.sub.2).sub.n O.sub.h (CH.sub.2).sub.i CHR.sup.2 (CH.sub.2).sub.r OH, and R.sup.3 ZR.sup.F ;
Z is selected from the group consisting of --NHCO--, --NHSO.sub.2 --, --O.sub.2 C--, --O.sub.3 S--, --OCH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 --, and --CH.sub.2 CHOHCH.sub.2 --;
m is 1 to 6;
n is 0 to 6;
R.sup.F is a perfluoro alkyl group, C.sub.p F.sub.2p+1, wherein p is 1 to 20;
h is 0 or 1;
i is 0 to 6;
r is 0 to 4; and
each R.sup.5 is independently selected from the group consisting of methyl group, ethyl group, and a phenyl group.

### Claim 2 (depends on 1)

The method of claim 1 wherein in the linear siloxane, a is 0; b is 1 to 20; c is 1 to 20; R.sup.3 is (CH.sub.2).sub.3 ; Z is --NHSO.sub.2 --; R.sup.F is C.sub.8 F.sub.17 ; m is 1; each R.sup.1, R.sup.4, and R.sup.5 is a methyl group; n is 0; R.sup.2 is a hydrogen, r is 0; h is 0; and i is 0.

### Claim 3 (depends on 1)

The method of claim 1, wherein in the cyclic siloxane, d is 0; e is 1 to 5; f is 1 to 5; R.sup.3 is (CH.sub.2).sub.3 ; Z is --NHSO.sub.2 --; R.sup.F is C.sub.8 F.sub.17 ; m is 1; each R.sup.1 and R.sup.5 is a methyl group; n is 0; R.sup.2 is a hydrogen, r is 0; h is 0; and i is 0.

### Claim 4 (depends on 1)

The method of claim 1 wherein the fibrous substrate is a natural fiber selected from the group consisting of cotton and cotton/polyester blends.

### Claim 5 (depends on 1)

The method of claim 1 wherein the durable press resin ##STR8## moiety.

### Claim 6 (depends on 1)

The method of claim 1 wherein the catalyst is an acid catalyst selected from the group consisting of p-toluenesulfonic acid, zinc chloride, zinc tetrafluoroborate, aluminum chloride, magnesium chloride, aluminum chlorohydroxide and mixtures thereof.

### Claim 7 (depends on 1)

The method of claim 1 wherein an organic solvent is employed.

### Claim 8 (depends on 7)

The method of claim 7 wherein the organic solvent is selected from the group consisting of (i) a low molecular weight alcohol having 1 to 5 carbon atoms; (ii) a ketone having 1 to 6 carbon atoms and (iii) a polyalkylene glycol or glycol ether having the formula: RO(CH.sub.2 CHR'O ).sub.n R", wherein n ranges from about 1 to 10, R' is selected from the group consisting of hydrogen and a methyl group, and each R and R" is independently selected from the group consisting of a hydrogen, an alkyl having 1 to 4 carbon atoms, and an aryl having 6 to 8 carbon atoms.

### Claim 9 (depends on 1)

The method of claim 1 wherein the durable press resin is selected from the group consisting of N,N-dimethylol-4,5-dihydroxyethyleneurea, 1,3-bis-(methoxymethyl)-4,5-dihydroxy-2-imidazolidinone, 1,3-dimethylolethyleneurea, dimethylol isopropyl carbamate, and 1,3-dimethyl-4,5-dihydroxy-2-imidazolidinone.