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.

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 co-polymer is made of 2-(dimethylamino)ethyl methacrylate (DMAEMA) and 2-hydroxyethyl methacrylate (HEMA).

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

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

9. 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.

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

11. 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).

12. 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.

13. 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.

14. 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) ##STR00011## 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, and at least one aliphatic or cycloaliphatic diisocyanate.

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

16. 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.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0068] 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.

[0069] FIGS. 2A and 2B show the anti-microbial effect of a representative quaternized co-polymer of the invention.

EXPERIMENTAL SECTION

Example 1

[0070] Preparation of the Co-Polymer 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

Quaternizing Process

[0071] 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

Coating Process

[0072] 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

Anti-Microbial Effect

[0073] The anti-bacterial effects of the co-polymer of Example 2 and the fabrics coated therewith were tested according to ASTM E2149-01 on: [0074] ATCC 35218 (Escherichia coli) [0075] ATCC 6538 (Staphylococcus aureus)

[0076] 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.

[0077] 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. 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.