Method for providing an anti-microbial and an anti-pilling effect and for improving dye uptake to textiles, novel co-polymers and textiles

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

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) ##STR00007## or mixture thereof, and a monomer of general formula (II) ##STR00008## or mixture thereof, wherein X is, each independently selected from the following (A) or (B) chains ##STR00009## 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 C.sub.1-C.sub.4 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, wherein said treating (i) creates urethane bridges which covalently bind said co-polymer to the textile; and wherein the aqueous solution comprises a co-polymer that is made up of 2-(dimethylamino)ethyl methacrylate (DMAEMA) and 2-hydroxyethyl methacrylate (HEMA) and wherein the molar DMAEMA/HEMA ratio is 95-85/5-15 and 20-40% of the tertiary amino groups are quaternized.

2. The method of claim 1, wherein Alk is a linear or branched, saturated C.sub.1-C.sub.4 alkyl group.

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

4. The method of claim 1, wherein the nitrogen atom in formula (I) is quaternized to provide a monomer of formula (I′) ##STR00010## wherein X and Alk are as above defined, Alk.sup.− is a C.sub.6 to C.sub.22 alkyl group, and Hal.sup.− indicates a halogen counter ion.

5. 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.

6. 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.

7. The method of claim 6, wherein said textile is denim.

Description

BRIEF DESCRIPTION OF THE FIGURES

(1) FIG. 1 shows a schematic representation of the reaction which occurs in the method of the invention, wherein n and m represent the number of monomers present in the co-polymer.

(2) FIGS. 2A and 2B show the anti-microbial effect of a representative quaternized co-polymer of the invention.

EXPERIMENTAL SECTION

Example 1

(3) Preparation of the Co-Polymer

(4) A monomer solution containing 100 mmol HEMA and 900 mmol DMAEMA is prepared and 10% of (v/v) said solution is added the reactor that is set 70° C. Then, 50 ml of distilled water is added in the reactor and stirred while monomer mixture, ammonium persulfate (22 g of ammonium persulfate is dissolved in 100 ml of water), and sodium metabisulfate (19 g sodium metabilsulfate is dissolved in 100 ml of water) solutions are being fed with the 2 ml/min rate. The co-polymer is collected from the reactor and washed with hot water (70-80° C.) to remove unreacted monomer, ammonium persulfate and sodium metabisulfite.

Example 2

(5) Quaternizing Process

(6) 25-30% of DMAEMA residues present in the co-polymer of Example 1 were quaternized with alkyl halides by following procedure: 50 g of the co-polymer is dissolved in 300 ml dry ethanol, and 75 mmol of an alkyl halide, preferably 1-bromodecane, is added, then the solution is stirred for 24 hour at room temperature. Ethanol is evaporated to collect the quaternized co-polymer by a conventional work-up step.

Example 3

(7) Coating Process

(8) A coating solution is prepared with water, the quaternized co-polymer of Example 2, hexamethylene diisocyanate, a wetting agent and a thickener according to the following: 2.5 g of quaternized co-polymer (10% of HEMA in co-polymer) is dissolved in 1 L of water with 50-75 mg of the diisocyanate, 6-8 g of wetting agent, and an amount of thickener which allows a 20-24 d.cP viscosity. The solution is then applied onto the fabric. This can be made for instance by coating or impregnation. In coating method, it is useful to add a thickener to the solution in order to have desired viscosity, whereas in impregnation process a thickener is not necessary. A sanforizing machine can also be used for applying the solution to the fabric. The coated fabric is dried at 150° C. for about 3 minutes and subsequently fixed at 170° C. for about 1 minute.

Example 4

(9) Anti-Microbial Effect

(10) The anti-bacterial effects of the co-polymer of Example 2 and the fabrics coated therewith were tested according to ASTM E2149-01 on: ATCC 35218 (Escherichia coli) ATCC 6538 (Staphylococcus aureus)

(11) The results showed that, the quaternized co-polymer of Example 2 shows an antimicrobial effect against Staphylococcus aureus and Escherichia coli, as reported in FIGS. 2A and 2B.

(12) FIGS. 2A and 2B show two petri dishes, each one divided into eight portions. In both FIGS. 2A and 2B, each one of the eight portions of the petri dishes corresponds to a different concentration of co-polymer tested. As can be observed from FIGS. 2A and 2B, the tested concentrations of the quaternized co-polymer of Example 2 were: 0.0195 g/L, 0.039 g/L, 0.078 g/L, 0.156 g/L, 0.3125 g/L, 0.625 g/L, 1.25 g/L and 2.5 g/L.

(13) As it can be seen from the Figures, the antimicrobial effect on Staphylococcus aureus is achieved even with very low concentrations of the co-polymer (starting from 0.0195 g/L) and the effect on Escherichia coli starts from 1.25 g/L and is very satisfying at 2.5 g/L.