EP0908553A2 - Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln - Google Patents

Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln Download PDF

Info

Publication number
EP0908553A2
EP0908553A2 EP98811000A EP98811000A EP0908553A2 EP 0908553 A2 EP0908553 A2 EP 0908553A2 EP 98811000 A EP98811000 A EP 98811000A EP 98811000 A EP98811000 A EP 98811000A EP 0908553 A2 EP0908553 A2 EP 0908553A2
Authority
EP
European Patent Office
Prior art keywords
antimicrobial agent
process according
fibre
formula
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98811000A
Other languages
English (en)
French (fr)
Other versions
EP0908553A3 (de
Inventor
Jianwen Mao
Marcel Schnyder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Priority to EP98811000A priority Critical patent/EP0908553A3/de
Publication of EP0908553A2 publication Critical patent/EP0908553A2/de
Publication of EP0908553A3 publication Critical patent/EP0908553A3/de
Withdrawn legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/152Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • D06M13/156Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring containing halogen atoms
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144Alcohols; Metal alcoholates
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/152Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/165Ethers
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325Amines
    • D06M13/342Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402Amides imides, sulfamic acids
    • D06M13/432Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

  • the present invention relates to a process for the treatment of textile materials with antimicrobial agents, formulations comprising the antimicrobial agent and the textile material treated by this process.
  • a more advantageous method incorporates the antimicrobials into the fibre melt during the melt spinning step, preferably within the macromolecular structure. This method enables the antimicrobials to be built into the fibres and to migrate onto the surface of the fibres/textiles to provide long lasting efficacy, depending on the nature of the polymers involved. The efficacy can often last as long as the life-cycle of the relevant textile materials.
  • Nonwoven textile materials can also be prepared from such a process. Because of the high temperatures, it is not feasible to directly incorporate antimicrobials, especially organic antimicrobials, into the molten polymers required for the fibre production process. At such temperatures, organic antimicrobials tend to decompose or vaporise.
  • the present invention therefore, relates to a process for the incorporation of an antimicrobial agent into a fibre, fabric or piece goods comprising treating said material by passing said fibre into an aqueous liquor containing an antimicrobial agent selected from
  • the antimicrobial agent (a) is selected from compounds of the formula wherein
  • antimicrobial agents (a) of formula (1) are used, wherein
  • antimicrobial agent (a) is a compound of formula wherein
  • Preferred phenol derivatives (b) correspond to formula wherein
  • Such compounds are typically chlorophenols (o-, m-, p-chlorophenols), 2,4-dichlorophenol, p-nitrophenol, picric acid, xylenol, p-chloro-m-xylenol, cresols (o-, m-, p-cresols), p-chloro-m-cresol, pyrocatechin, resorcinol, orcinol, 4-n-hexylresorcinol, pyrogallol, phloroglucine, carvacrol, thymol, p-chlorothymol, o-phenylphenol, o-benzylphenol, p-chloro-o-benzylphenol and 4-phenolsulfonic acid.
  • Typical antimicrobial agents (c) correspond to the formula wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently of one another hydrogen or chloro.
  • Illustrative examples of compounds of formula (5) are benzyl alcohol, 2,4-, 3,5- or 2,6-dichlorobenzyl alcohol and trichlorobenzyl alcohol.
  • Antimicrobial agent (d) is chlorohexidine and salts thereof, for example 1,1'-hexamethylene-bis-(5-(p-chlorophenyl)-biguanide), together with organic and inorganic acids and chlorhexidine derivatives such as their diacetate, digluconate or dihydrochloride compounds.
  • Antimicrobial agent (e) is typically C 8 -C 18 cocamidopropylbetaine.
  • Amphoteric surfactants as antimicrobial agents (f) are suitably C 12 alkylaminocarboxylic and C 1 -C 3 alkanecarboxylic acids such as alkylaminoacetates or alkylaminopropionates.
  • Typical trihalocarbanilides which are useful as antimicrobial agent (g) are compounds of the formula wherein
  • the quatemary and polyquaternary compounds which correspond to antimicrobial agent (h) are of the formula wherein
  • n is an integer from 7 to 17, is very particularly preferred.
  • a further exemplified compound is cetyl trimethylethyl ammonium bromide.
  • antimicrobial agent (i) is methylchloroisotahazoline.
  • the antimicrobial agents which are used in the present process are water-soluble or only sparingly soluble in water. In the present aqueous formulation they may therefore be applied as aqueous formulation in diluted, solubilised, emulsified or dispersed form.
  • the antimicrobial agents are applied in dispersed form they are milled with an appropriate dispersant, conveniently using quartz balls and an impeller, to a particle size of 1-2mm.
  • Suitable dispersants for the antimicrobial agents in the present process are:
  • the concentration of the antimicrobial agents is from 0.1%-30%, preferably 2-10% b.w..
  • Suitable solubilizing agents are anionic, nonionic or zwitterionic and amphoteric synthetic, surface-active substances.
  • Suitable anionic surface-active substances are:
  • the anionic surfactants used may furthermore be fatty acid methyl taurides, alkylisothionates, fatty acid polypeptide condensates and fatty alcohol phosphoric acid esters.
  • the alkyl radicals in these compounds preferably contain 8 to 24 carbon atoms.
  • the anionic surfactants are usually obtained in the form of their water-soluble salts, such as the alkali metal, ammonium or amine salts.
  • Typical examples of such salts are lithium, sodium, potassium, ammonium, triethylamine, ethanolamine, diethanolamine or triethanolamine salts. It is preferred to use the sodium or potassium salts or the ammonium-(NR 1 R 2 R 3 ) salts, wherein R 1 , R 2 and R 3 are each independently of one another hydrogen, C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl.
  • Very particularly preferred anionic surfactants in the novel formulation are monoethanolamine lauryl sulfate or the alkali metal salts of fatty alcohol sulfates, preferably the sodium lauryl sulfate, sodium laureth-2 sulfate or sodium cumene sulfonate.
  • Suitable zwitterionic and amphoteric surfactants are imidazoline carboxylates, alkylamphocarboxy carboxylic acids, alkylamphocarboxylic acids (e.g. lauroamphoglycinate) and N-alkyl- ⁇ -aminopropionates or N-alkyl-b-iminodipropionates.
  • Nonionic surfactants are typically derivatives of the adducts of propylene oxide/ethylene oxide having a molecular weight of 1000 to 15000, fatty alcohol ethoxylates (1-50 EO), alkylphenol polyglycol ethers (1-50 EO), ethoxylated carbohydrates, fatty acid glycol partial esters, typically diethylene glycol monostearate, PEG5 - PEG25 glyceryl stearate, for example PEG-5 glyceryl stearate, PEG15 glyceryl stearate or PEG25 glyceryl stearate; cetearyl octanoate; fatty acid alkanolamides and fatty acid dialkanolamides, fatty acid alkanolamide ethoxylates and fatty acid amine oxides.
  • the salts of saturated and unsaturated C 8 -C 22 fatty acids may be used as solubilizing agents, either by themselves, in admixture with each other or in admixture with the other surface-active substances cited for component (c).
  • Illustrative examples of these fatty acids are typically capric, lauric, myristic, palmitic, stearic, arachic, behenic, dodecenoic, tetradecenoic, octadecenoic, oleic, eicosanic and erucic acid, as well as the technical mixtures of such acids, typically coconut fatty acid.
  • acids may be obtained in the form of salts, suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • suitable solubilizing agents in the present composition are dihydric alcohols, preferably those containing 2 to 6 carbon atoms in the alkylene radical, typically ethylene glycol, 1,2- or 1,3-propanediol, 1,3-, 1,4- or 2,3-butanediol, 1,5-pentanediol and 1 ,6-hexanediol or monohydric alcohol like methanol; ethanol or propanol; and acetone.
  • dihydric alcohols preferably those containing 2 to 6 carbon atoms in the alkylene radical, typically ethylene glycol, 1,2- or 1,3-propanediol, 1,3-, 1,4- or 2,3-butanediol, 1,5-pentanediol and 1 ,6-hexanediol or monohydric alcohol like methanol; ethanol or propanol; and acetone.
  • mixtures of anionic, nonionic, zwitterionic, amphoteric surface-active subatances and one or more of the mono- and/or dihydric alcohols mentioned above can be used for solubilising the antimicrobial agent.
  • the aqueous liquor containing the antimicrobial agent (a) to (I), is prepared by first milling and then dispersing the antimicrobial agent into fine particles, or by solubilising or dispersing or dissolving in water the antimicrobial agent without milling process.
  • the antimicrobial agent before incorporation is dissolved in surfactants, with or without a small amount of organic solvent, other ingredients and water.
  • the aqueous liquor is heated up above the melting point of the antimicrobial agent in order to support the solubilising or dispersing process.
  • the aqueous liquor prepared by this method and containing the antimicrobial agent in dispersed or solubilised form can be diluted to almost any ratio.
  • the antimicrobial agent is added to the aqueous liquor in an amount of 0.001 to 10% b.w., based on the fibre material.
  • Fibre material which can be treated with the antimicrobial agents are materials comprising for example, silk, leather, wool, polyamide, for example nylon (including nylon-6, Nylon-66), or polyurethanes, polyester, polyacrylonitrile polypropylene, polyethylene and cellulose-containing fibre materials of all kinds, for example natural cellulose fibres, such as cotton, linen, jute and hemp, and also viscose staple fibre and regenerated cellulose.
  • Polyester fibre materials which can be treated with the antimicrobial agents will be understood as including cellulose ester fibres such as cellulose secondary acetate and cellulose triacetate fibres and, preferably, linear polyester fibres which may also be acid-modified, and which are obtained by the condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis(hydroxymethyl)cyclohexane, as well as copolymers of terephthalic and isophthalic acid and ethylene glycol.
  • the linear polyester fibre material (PES) hitherto used almost exclusively in the textile industry consists of terephthalic acid and ethylene glycol.
  • the fibre materials may also be used as blends of natural fibres like cotton, wool or jute with each other or with synthetic fibre materials like PES, Nylon or polypropylene or blends of synthetic fibre materials with each other.
  • Typical fibre blends are of polyacrylonitrile-polyester, polyamide/polyester, polyester/cotton, polyester/viscose and polyester/wool.
  • the textile fibre material can be in different forms of presentation, preferably as woven or knitted fabrics or as piece goods such as knitgoods, woven fabrics nonwoven textiles, carpets, piece garments also as yarn on cheeses, warp beams and the like or finished goods in any other form, preferably T-shirts, sport wears, running bra, sweaters, coats, lingeries, underwears and socks.
  • the fibres or fibre blends can be treated batchwise or continuously.
  • the treatment of the fibre materials is carried out from an aqueous liquor by a continuous or batch process.
  • the liquor ratio may be chosen from a wide range, typically from 1:4 to 1:100, preferably from 1:5 to 1:50.
  • the treatment temperature is not lower than 50°C and is normally not higher than 140°C.
  • the preferred temperature range is from 80 to 135°C.
  • the aqueous liquor contains the antimicrobial agent in a concentration which is sufficient to cause the agent to be exhausted into the fibre.
  • concentration of the antimicrobial agent is preferably form 0.01 to 10% b.w., most preferably from 0.05 to 5% b.w., based on the weight of the fibre or fabric material.
  • the treatment liquors which may optionally contain assistants, are applied to yarns, fabric, piece goods, for example, by padding or slop-padding and are developed by thermofixation or HT steaming processes.
  • Linear polyester fibres and cellulose fibres are preferably treated by the high temperature process in closed and pressure-resistant apparatus at temperatures of >80°C, preferably in the range from 90 to 120°C, and at normal or elevated pressure.
  • Suitable closed apparatus includes typically machines which are also used for dyeing processes, like circulation dyeing machines such as cheese or beam dyeing machines, winch becks, jet or drum dyeing machines, muff dyeing machines, paddles or jiggers.
  • Cellulose secondary acetate is preferably treated in the temperature range of from 80-85°C.
  • the treatment time is from 5 to 30, preferably 10 to 20 minutes.
  • the fibre material which is treated by the present process is characterised by having an essentially homogeneous distribution of the antimicrobial agent throughout the fibre cross-section.
  • Suitable dyes are disperse dyes which are only sparingly soluble in water, metal complex dyes or acid dyes. They are therefore present in the dye liquor substantially in the form of a fine dispersion. They may belong to different dye classes, including acridone, azo, anthraquinone, coumarin, methine, perinone, naphthoquinone-imine, quinophthalone, styryl or nitro dyes. Mixtures of disperse dyes may also be used in the practice of this invention.
  • the procedure can be such that the fibre material is first treated with these compounds and then dyeing is carried out or, preferably, the fibre material is treated simultaneously in the dyebath with the antimicrobial agent and the dye.
  • the application of the antimicrobial agent can, however, also be effected subsequently to the previously prepared dyeing by thermofixation.
  • the treatment liquors may also contain further ingredients such as dyeing assistants, dispersants, carriers, wool protectives, and wetting agents as well as antifoams.
  • the treatment liquors may also contain mineral acids, typically sulphuric acid or phosphoric acid, or conveniently organic acids, typically including aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and/or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • mineral acids typically sulphuric acid or phosphoric acid
  • organic acids typically including aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and/or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids are used in particular to adjust the pH of the liquors used in the practice of this invention to 4-5.
  • the fibre material is first run into the bath which contains the antimicrobial agent, preferably the dye, and any further auxiliaries, and which has been adjusted to pH 4.5-5.5 at 20-80°C, then the temperature is raised to 80-125°C over 20 to 40 minutes, and further treatment is carried out for 10 to 100 minutes, preferably for 20-80 minutes preferably in the temperature range of 80 to 125°C.
  • the antimicrobial agent preferably the dye, and any further auxiliaries
  • the samples are finished by cooling the treatment liquor to 50-80°C, optionally washing off the dyeings with water and, if necessary, reductively clearing them in conventional manner in alkaline medium.
  • the treated samples are then again washed off and dried.
  • vat dyes for dyeing the cellulose component the goods are first treated with hydrosulfite at pH 6-12.5, then treated with an oxidising agent and finally washed off.
  • the process of this invention makes it possible to obtain antimicrobial finished textile materials having long lasting efficacy.
  • the textile materials finished by the process of the present invention are advantageous with respect to inhibition of micro-organisms, reduction of the risk of contamination, reduction of odour, increase in freshness and improvement in hygienic conditions.
  • Example 1 50ml of the formulation prepared in Example 1 are placed in a suitable vessel and are diluted with water of 1000ml, together with approximately 500g of textile materials made from poly(ethylene terephthalate). The vessel is then sealed and placed in a bath at 120°C for 1-5 hours. The treated textile is then removed from the formulation and rinsed thoroughly with water.
  • Triclosan The concentration of Triclosan in the treated textile was measured by dissolving an appropriate amount of such textile material in dichloro acetic acid followed by an appropriate separation/extraction procedure, and then HPLC analysis. The concentration is found to be 0.26% of the total weight of the textiles.
  • Triclosan is incorporated into the intermolecular structure or rather has been absorbed on the surface of the textile.
  • an extraction experiment is carried out.
  • an appropriate amount of treated textile is subjected to Soxhlet extraction by hexane, which is a good solvent of Triclosan, for 60 minutes.
  • the concentration of Triclosan in the textiles that has undergone extraction and the extractant are analysed by HPLC respectively. It is found that the concentration of Triclosan in the fibre remains almost unchanged, whereas the amount of Triclosan in the extractant is negligible.
  • Sample Polyester sample LA 45 Microbiological evaluation Determination of the bacteriostatic activity according to the bacterial growth inhibition test (modified test method CG 147). Principle Discs with 20 mm diameter are cut under sterile conditions and then applied on the top layer of the solidified agar containing the bacteria (from over-night cultures, an 1:100 (S. aureus) and an 1:1000 (E. coli) dilution is made and 3.5 ml are added to 500 ml agar). After the incubation, the inhibition zones are measured and the results obtained are set out in Table 1.
  • Example 6a 2.5 ml of the formulation as prepared in Example 6a is added to 195 ml of water. 10 g of a blend of cotton (40%) and polyester (60%) fabric are then added to the diluted formulation and the mixture is heated up to 130°C for 60 min. After that, the fabric is washed and the content of Triclosan in the fabric is found to be 0.42% in the polyester.
  • Example 8 Determination of the antimicrobial activity of 2 polyester samples treated with Triclosan
  • the PES samples containing Triclosan show excellent antibacterial effects against the gram positive Staphylococcus aureus and the gram negatives Escherichia coli and Proteus vulgaris even after 20 washes.
  • a bottom layer of 15 ml sterile agar medium is poured in petri dishes and after solidification of the agar, 6 ml of a germ-containing agar are evenly distributed on the bottom agar layer.
  • 6 ml of a germ-containing agar are evenly distributed on the bottom agar layer.
  • a 1:100 ( Staph. aureus) and 1:1000 (E. coli and Pr. vulgaris) diluted over-night cultures of the bacteria are mixed with 500 ml molten agar at 47°C.
  • the samples of the fabric (discs with 20 mm diameter) are applied in the middle of the inoculated plates (one sample on each agar plate). Each test material is tested twice.
  • Triclosan 6 g are dissolved in 4 g of propylene glycol (solution A). 0.5 g of sodium lauryl sulfate is dissolved in 200 g of water (solution B). Then 90 mg of Solution A are added to Solution B which is heated at 60°C. The resulting mixture is a clear solution (solution C) wherein Triclosan is solubilised. 10 g of polyester fabric are added to Solution C and heated to 130°C for 60 minutes. The PES fabric is then washed.
  • the concentration of Triclosan in the treated PES fabric is 0.48%.
  • Triclosan 10 g are dissolved in a mixture of 10 g of isopropanol and 20 g of propylene glycol. To this mixture 50 g of sodium lauryl sulphate and 5 g of sodium cumenesulfonate and 5 g of water are added.
  • Example 10 0.5 g of the formulation as prepared in Example 10 is added to 200 g of water. The resulting mixture is a turbid but stable emulsion. Into this mixture 10 g of Nylon 66 fabric is added and the antimicrobial treatment can be carried out at 95°C for 60 minutes.
  • the nylon 66 fabric contains 0.5% of Triclosan after treatment.
  • Example 12 Incorporation of antimicrobial into nylon fabrics in a simultaneously dyeing process
  • Example 6 This example the antimicrobial formulation is added together with dyestuff to Nylon 6 and nylon 66 fabrics, i.e. the treatment is carried together with the dyeing of the fabrics.
  • the amount of antimicrobial formulation of Example 6 added is always 1 gram.
  • the duration of treatment is always 60 minutes. Concentration of Triclosan is analysed using conditions as described in Example 3.
  • Liquor ratio used in the experiments is 1:10, thus 20 grams of fabrics in 200 ml of water bath.
  • Dyestuff used in this example are: Lanaset Green B® 1.0% owf Lanaset Blue 2R® 0.8% owf Lanaset Bordeaux® B 0.2% owf Erionyl yellow® A-R 0.6% owf
  • Example 13 Incorporation of antimicrobial into nylon carpets in a continuos process together with dyestuff
  • nylon made carpets The majority of nylon made carpets is dyed in a continuous process involving padding the undyed carpets with dyestuff dispersed/dissolved in aqueous bath followed by steam fixation at about 100°C for 2-10 minutes followed by spin drying, rinsing, spinning drying and oven drying.
  • the same antimicrobial formulation as described in example 6 is incorporated into the dye bath.
  • the dyestuffs used in this experiment are: Tectilon® Yellow 3R 200% 1.13% owf Tectilon® Red 23 200% 0.464% owf Tectilon® Blue 4R-0 200% 0.46% owf
  • Example 6 To this formulation, 11.5g /l of the formulation as described in Example 6 is added. The pickup of the bath to carpet is 450%. Carpets are prewetted with Tinovetin® Ju at 1g/l at 60°C.
  • the concentration of Triclosan fixed in the carpets is found to be around 0.4% in both samples.
  • Example 14 Incorporation of antimicrobial into nylon carpets in a continuos process together with dyestuff.
  • the majority of t nylon made carpets is dyed in a continuous process involving padding the undyed carpets with dyestuff dispersed/dissolved in aqueous bath followed by steam fixation at about 100°C for 2-10 minutes followed by spin drying, rinsing, spinning drying and oven drying.
  • the same antimicrobial formulation as described in example 6 is incorporated into the dye bath.
  • the dyestuffs used in this experiment are: Tectilon® Yellow 3R 200% 1.13% owf Tectilon® Red 23 200% 0.464% owf Tectilon® Blue 4R-0 200% 0.46% owf
  • Example 6 To this formulation, 11.5g /l of the formulation as described in Example 6 is added. The pickup of the bath to carpet is 450%. Carpets are prewetted with Tinovetin® Ju at 1g/l at 60°C.
  • the concentration of Triclosan fixed in the carpets is found to be around 0.4% in both samples.
  • Example 15 0.5 gram of the formulation as prepared in Example 15 is used to treat Nylon 66 fabrics using procedures as described in Example 11.
  • the treated fabric contains 0.5% of 4,4'-dichloro-2'-hydroxy-diphenylether.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP98811000A 1997-10-13 1998-10-05 Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln Withdrawn EP0908553A3 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98811000A EP0908553A3 (de) 1997-10-13 1998-10-05 Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP97810767 1997-10-13
EP97810767 1997-10-13
EP98810677 1998-07-15
EP98810677 1998-07-15
EP98811000A EP0908553A3 (de) 1997-10-13 1998-10-05 Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln

Publications (2)

Publication Number Publication Date
EP0908553A2 true EP0908553A2 (de) 1999-04-14
EP0908553A3 EP0908553A3 (de) 2001-03-07

Family

ID=27238771

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98811000A Withdrawn EP0908553A3 (de) 1997-10-13 1998-10-05 Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln

Country Status (1)

Country Link
EP (1) EP0908553A3 (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000026447A1 (en) * 1998-10-29 2000-05-11 Ciba Specialty Chemicals Holding Inc. Incorporation of organic anti-microbials into fibres during a fibre spinning process
WO2002055301A1 (de) * 2001-01-10 2002-07-18 Mitsubishi Polyester Film Gmbh Antimikrobiell ausgerüstete, mehrschichtige polyesterfolie mit matter oberfläche
WO2002092902A1 (fr) * 2001-05-17 2002-11-21 Ajinomoto Co., Inc. Agent de traitement de fibres, procede de fabrication d'agents antibacteriens pour fibres et procede de fabrication de fibres antibacteriennes
WO2003078367A2 (en) * 2002-03-19 2003-09-25 Ciba Specialty Chemicals Holding Inc. Benzyl alcohol derivatives and their use as antimicrobial agents
EP1591010A2 (de) * 2004-04-15 2005-11-02 Kenji Nakamura Kosmetische Werkzeug mit antibakteriellen Eigenschaften und dessen Herstellung
US7105500B2 (en) * 2000-09-14 2006-09-12 Ciba Specialty Chemicals Corp. Process for the antimicrobial treatment of fiber materials
EP1718788A2 (de) * 2004-02-25 2006-11-08 Supreme Elastic Corporation Verfahren zur herstellung von antimikrobiell ausgerüsteten verbundgarnen, verbundwaren und daraus hergestellte gegenstände
EP3808890A1 (de) * 2015-02-27 2021-04-21 Livinguard AG Textilien mit antimikrobiellen eigenschaften

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1022744A (en) * 1963-02-22 1966-03-16 Geigy Ag J R New phenolic antimicrobial compositions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59144678A (ja) * 1983-02-01 1984-08-18 三菱レイヨン株式会社 繊維への恒久抗菌性付与加工法
JPS59157376A (ja) * 1983-02-22 1984-09-06 三菱レイヨン株式会社 繊維の漂白ならびに抗菌性付与加工法
JPS59199864A (ja) * 1983-04-20 1984-11-13 三菱レイヨン株式会社 ポリオレフイン系繊維への恒久抗菌性付与加工法
JPH06116865A (ja) * 1992-10-02 1994-04-26 Mitsubishi Rayon Co Ltd セルロース系繊維の抗菌処理方法
JPH07268775A (ja) * 1994-03-25 1995-10-17 Teisan Seiyaku Kk 抗菌性薬物含有ナイロン繊維及びその製造法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1022744A (en) * 1963-02-22 1966-03-16 Geigy Ag J R New phenolic antimicrobial compositions

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch, Week 199421 Derwent Publications Ltd., London, GB; Class A35, AN 1994-174259 XP002154540 & JP 06 116865 A (MITSUBISHI RAYON CO LTD) , 26 April 1994 (1994-04-26) *
DATABASE WPI Section Ch, Week 8439 Derwent Publications Ltd., London, GB; Class A87, AN 84-241098 XP002060462 -& JP 59 144678 A (MITSUBISHI RAYON CO LTD), 18 August 1984 (1984-08-18) *
DATABASE WPI Section Ch, Week 8442 Derwent Publications Ltd., London, GB; Class A35, AN 84-259753 XP002060464 -& JP 59 157376 A (MITSUBISHI RAYON CO LTD), 6 September 1984 (1984-09-06) *
DATABASE WPI Section Ch, Week 8451 Derwent Publications Ltd., London, GB; Class A35, AN 84-316465 XP002060463 -& JP 59 199864 A (MITSUBISHI RAYON CO LTD), 13 November 1984 (1984-11-13) *
DATABASE WPI Section Ch, Week 9550 Derwent Publications Ltd., London, GB; Class A23, AN 95-390919 XP002060461 -& JP 07 268775 A (TEISAN SEIYAKU KK), 17 October 1995 (1995-10-17) *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000026447A1 (en) * 1998-10-29 2000-05-11 Ciba Specialty Chemicals Holding Inc. Incorporation of organic anti-microbials into fibres during a fibre spinning process
US7105500B2 (en) * 2000-09-14 2006-09-12 Ciba Specialty Chemicals Corp. Process for the antimicrobial treatment of fiber materials
WO2002055301A1 (de) * 2001-01-10 2002-07-18 Mitsubishi Polyester Film Gmbh Antimikrobiell ausgerüstete, mehrschichtige polyesterfolie mit matter oberfläche
WO2002092902A1 (fr) * 2001-05-17 2002-11-21 Ajinomoto Co., Inc. Agent de traitement de fibres, procede de fabrication d'agents antibacteriens pour fibres et procede de fabrication de fibres antibacteriennes
WO2003078367A2 (en) * 2002-03-19 2003-09-25 Ciba Specialty Chemicals Holding Inc. Benzyl alcohol derivatives and their use as antimicrobial agents
WO2003078367A3 (en) * 2002-03-19 2004-07-29 Ciba Sc Holding Ag Benzyl alcohol derivatives and their use as antimicrobial agents
EP1718788A2 (de) * 2004-02-25 2006-11-08 Supreme Elastic Corporation Verfahren zur herstellung von antimikrobiell ausgerüsteten verbundgarnen, verbundwaren und daraus hergestellte gegenstände
EP1718788A4 (de) * 2004-02-25 2009-12-02 Supreme Elastic Corp Verfahren zur herstellung von antimikrobiell ausgerüsteten verbundgarnen, verbundwaren und daraus hergestellte gegenstände
US7939686B2 (en) 2004-02-25 2011-05-10 Supreme Corporation Method for providing antimicrobial composite yarns, composite fabrics and articles made therefrom
EP1591010A2 (de) * 2004-04-15 2005-11-02 Kenji Nakamura Kosmetische Werkzeug mit antibakteriellen Eigenschaften und dessen Herstellung
EP1591010A3 (de) * 2004-04-15 2010-02-24 Kenji Nakamura Kosmetische Werkzeug mit antibakteriellen Eigenschaften und dessen Herstellung
EP3808890A1 (de) * 2015-02-27 2021-04-21 Livinguard AG Textilien mit antimikrobiellen eigenschaften

Also Published As

Publication number Publication date
EP0908553A3 (de) 2001-03-07

Similar Documents

Publication Publication Date Title
US20010055651A1 (en) Process for the treatment of textile materials with an antimicrobial agent
US6299651B1 (en) Fabrics comprising fibers having esterified triclosan derivatives diffused therein
US20100120311A1 (en) Method for providing textiles with desensitized silver components
US6344207B1 (en) Molded antimicrobial article and a production process thereof
US6346125B1 (en) Process for the treatment of nonwovens with antimicrobial agents
EP0908553A2 (de) Prozess zur Behandlung von Textilien mit bakterienabtötenden Mitteln
EP0474595B1 (de) Wässrige Dispersion schwerlöslicher UV-Absorber
US20040006826A1 (en) Method for the treatment of textile materials against fungi and dust mites
JP3243341B2 (ja) 未染色ならびに染色されたポリエステル繊維材料の光化学的および熱的安定化方法
US20060134446A1 (en) Non-yellowing aldehyde condensation products
JPH09194304A (ja) 繊維の抗菌処理方法
EP0964096A2 (de) Verfahren zur Verbesserung der photochemischen und thermischen Stabilität von Färbungen und Drucken auf Polyesterfasermaterialien
JPH07196631A (ja) 非染色及び染色又は捺染したポリエステル繊維材料を光化学的及び熱的に安定化する方法
US4877538A (en) Sulfomethylated stain blocking agents
MXPA98008415A (es) Proceso para el tratamiento de materiales textiles con un agente antimicrobiano
KR20010087382A (ko) 섬유 방사 공정 동안에 유기 살균제를 섬유 속으로도입하는 방법
JPH01229072A (ja) 合成繊維加工用の低起泡性組成物
TW434344B (en) Process for the treatment of textile materials with an antimicrobial agent
US4670336A (en) Laundry-stable, antimicrobially-active fibers and filaments and the production thereof
EP0064030B1 (de) Färbereihilfsmittelgemisch und seine Verwendung beim Färben von synthetischen Fasermaterialien
JPS59112070A (ja) 抗菌性を有するポリアミド系繊維製品の製造法
DE3837001A1 (de) Verfahren zum nachbehandeln von faerbungen mit anionischen farbstoffen
JP2001131255A (ja) ホルムアルデヒド縮合物及びこれを含有する繊維用処理剤
JPS59144678A (ja) 繊維への恒久抗菌性付与加工法
EP0864687A2 (de) Verfahren zur Verbesserung der photochemischen Stabilität von Färbungen und Drucken auf Polyesterfasern

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE ES FR GB GR IT LI NL

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

17P Request for examination filed

Effective date: 19990909

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

AKX Designation fees paid

Free format text: CH DE ES FR GB GR IT LI NL

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20031212