# US 2019/0375869 A1 · Method for providing an anti-microbial and an anti-pilling effect and for improving dye uptake to textiles, novel co-polymers and textiles

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- Number: US 2019/0375869 A1
- Document ID: US20190375869A1
- Status: Published application
- Kind: A1
- Application number: 16/434,907
- Filed: 2019-06-07
- Published: 2019-12-12
- Earliest claimed: 2018-06-11
- Assignees: Sanko Tekstil Isletmeleri San. Ve Tic. A.S.
- Applicants: Sanko Tekstil Isletmeleri San. Ve Tic. A.S.
- Inventors: Gökhan KAPLAN; Leyla ZENGI; Semih KAZANÇ; Mustafa ZEYREK
- Web page: https://patentgrep.com/patent/US20190375869A1

## CPC

- D06M 16/00: Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- A01N 37/02: Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- C08F 220/34: Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate}
- C09D 5/14: Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence)
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- D06M 13/395: Isocyanates
- D06M 15/263: of unsaturated carboxylic acids; Salts or esters thereof
- D06M 15/267: of unsaturated carboxylic esters having amino or quaternary ammonium groups
- D06N 3/04: with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06P 1/525: {Polymers of unsaturated carboxylic acids or functional derivatives thereof}
- D06P 1/6424: {Compounds containing isocyanate or isothiocyanate groups}
- D06P 3/60: Natural or regenerated cellulose
- D06P 5/002: {Locally enhancing dye affinity of a textile material by chemical means}
- D06P 5/225: {Aminalization of cellulose; introducing aminogroups into cellulose}
- D06M 2200/35: Abrasion, pilling or fibrillation resistance
- D06N 2209/1671: Resistance to bacteria, mildew, mould, fungi
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- D06N: WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06P: DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM

## Abstract

The present invention relates to a method for providing an anti-microbial and an anti-pilling effect to textiles and for improving dye uptake to textiles. The invention also relates to novel co-polymers to be used in the method of the invention and to novel textiles.

## Claims

### Claim 1

A method for providing an anti-microbial and an anti-pilling effect and for improving dye uptake to a textile, said method comprising
(i) treating said textile with an aqueous solution comprising
a) at least one co-polymer made of a monomer of general formula (I)
or mixture thereof,
and a monomer of general formula (II)
or mixture thereof,
wherein
X is, each independently selected from the following (A) or (B) chains
the stars indicate the bonds linked to the oxygen and nitrogen atoms in the monomers of formula (I) and formula (II);
n is, each independently, an integer from 1 to 10; and
Alk is a C1-C4 alkyl group;
and wherein the tertiary amino groups in formula (I) are partially quaternized with halo-long chain alkyl groups;
and
b) at least one aliphatic or cycloaliphatic diisocyanate; and
(ii) optionally drying and/or fixing said textile.

### Claim 2 (depends on 1)

The method of claim 1, wherein Alk is a linear or branched, saturated C1-C4 alkyl group.

### Claim 3 (depends on 1)

The method of claim 1, wherein n is an integer from 1 to 8.

### Claim 4 (depends on 1)

The method of claim 1, wherein the nitrogen atom in formula (I) is quaternized to provide a monomer of formula (I′)
wherein X and Alk are as above defined, Alk− is a C6 to C22 alkyl group, and
Hal− indicates a halogen counter ion.

### Claim 5 (depends on 1)

The method of claim 1, wherein said aliphatic or cycloaliphatic diisocyanate is selected from hexamethylene diisocyanate, isophorone diisocyanate, methylene-bis(4-cyclohexylisocyanate) and blocked aliphatic or cycloaliphatic diisocyanates.

### Claim 6 (depends on 1)

The method of claim 1, wherein said co-polymer is made of 2-(dimethylamino)ethyl methacrylate (DMAEMA) and 2-hydroxyethyl methacrylate (HEMA).

### Claim 7 (depends on 1)

The method of claim 1, wherein said monomer of formula (I)/monomer of formula (II) molar ratio is about 95-85/5-15.

### Claim 8 (depends on 1)

The method of claim 1, wherein 20-40% of the tertiary amino groups are quaternized in the co-polymer.

### Claim 9 (depends on 1)

The method of claim 1, wherein said textile is selected from any material suitable to prepare fabrics and garments, yarns, ready for dyeing fabrics, any textile articles, and garment articles.

### Claim 10 (depends on 9)

The method of claim 9, wherein said textile is denim.

### Claim 11 (depends on 1)

The method of claim 1, wherein the copolymer (a) and the textile are at least partially covalently linked by urethane bridges provided by the aliphatic or cycloaliphatic diisocyanate (b).

### Claim 12 (depends on 4)

A co-polymer of DMAEMA and HEMA, wherein the molar DMAEMA/HEMA ratio is 95-85/5-15, and 20-40% of the tertiary amino groups are quaternized as defined in claim 4.

### Claim 13 (depends on 1)

Method of providing an anti-microbial, anti-pilling effect to a textile and for improving dye uptake of a textile, said method comprising treating said textile with at least one co-polymer, wherein 20-40% of the tertiary amino groups are quaternized or with the aqueous solution as defined in claim 1.

### Claim 14 (depends on 13)

The method of claim 13, wherein said aqueous solution comprises
at least one co-polymer of DMAEMA and HEMA, wherein the molar DMAEMA/HEMA ratio is 95-85/5-15, and 20-40% of the tertiary amino groups are quaternized to provide a monomer of formula (I′)
wherein X and Alk are as above defined, Alk− is a C6 to C22 alkyl group, and
Hal− indicates a halogen counter ion, and
at least one aliphatic or cycloaliphatic diisocyanate.

### Claim 15 (depends on 1)

A textile, treated by the method according to claim 1.

### Claim 16 (depends on 1, 15)

A textile according to claim 15, comprising fibers or filaments having hydroxyl groups, wherein at least part of said hydroxyl groups on said textiles are covalently linked to a co-polymer made of at least a monomer of formula (I) or (I′) and at least a monomer of formula (II) or (II′), as defined in claim 1 by means of a urethane bridge.