EP1141453A1 - Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres - Google Patents

Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres

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Publication number
EP1141453A1
EP1141453A1 EP99952595A EP99952595A EP1141453A1 EP 1141453 A1 EP1141453 A1 EP 1141453A1 EP 99952595 A EP99952595 A EP 99952595A EP 99952595 A EP99952595 A EP 99952595A EP 1141453 A1 EP1141453 A1 EP 1141453A1
Authority
EP
European Patent Office
Prior art keywords
condensates
formaldehyde
acid
process according
mol
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Withdrawn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
EP99952595A
Other languages
German (de)
English (en)
Inventor
Jianwen Mao
Clement Gui Min Zhang
Frank Chao Ma
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.)
BASF Schweiz AG
Ciba SC Holding AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC 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 Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP99952595A priority Critical patent/EP1141453A1/fr
Publication of EP1141453A1 publication Critical patent/EP1141453A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0058—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/02—Cellulose; Modified cellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/22—Cellulose xanthate
    • C08L1/24—Viscose

Definitions

  • the present invention relates to a process for the incorporation of antimicrobial agents, antifungal agents or mixtures thereof into fibres and the fibres resulting from this process.
  • Antimicrobial textile finishing in the form of a surface treatment of the textiles is already known, however the antimicrobials can be easily washed off in the subsequent use of such textiles.
  • a preferable incorporation method would be to add antimicrobial active ingredients into the fibres.
  • the only feasible means of such an incorporation involves adding antimicrobials into the soluble form of the cellulose followed by extrusion from the spinneret to form soft filaments which are then regenerated into cellulose. Rayon's are wet spun which means that the filaments emerging from the spinneret pass directly into chemical baths for solidifying or regeneration.
  • Another rational approach would be to dissolve the antimicrobial in a solvent which is compatible with the soluble form of the cellulose. But the difficulty is that when the soluble form of cellulose is extruded from the spinneret, it passes directly into chemical baths in which the chemical reactions take place for regeneration of cellulose. If the antimicrobial is dissolved in an organic solvent, the antimicrobial would remain in the organic phase after regeneration. If the antimicrobial is dissolved in an aqueous solvent, the antimicrobial would remain in solution and leach out of the fibre during regeneration. Therefore unsatisfactory incorporation of the antimicrobial into the fibre usually occurs.
  • fibres with improved antimicrobial and/or antifungal activity are provided by a process in which antimicrobials, antifungals or a mixture thereof and one or more surface active agents are added into the soluble form of the cellulose, then the fibres are formed by extrusion from a spinneret and finally the fibres are regenerated into cellulose.
  • This invention relates to a process for finishing regenerated cellulose fibres with antimicrobial agents, antifungal agents, or a mixture thereof wherein in the first step, a formulation comprising an anti-microbial agent, an anti-fungal agent or a mixture thereof and one or more surface active agents are added to the soluble form of the fibres prior to regeneration and in a second step this mixture is extruded from a spinneret to form the regenerated fibre.
  • the antimicrobial agents are selected from the group consisting of
  • the antimicrobial agent (a) is selected from compounds of the formula whe rein
  • X is oxygen, sulfur or -CH2-
  • Y is chloro or bromo
  • z is SO2H, NO2 or C ⁇ -C4-Alkyl
  • r is 0 to 3
  • o is 0 to 3
  • P is 0 or 1 , m is 0 or 1 and n is 0 or 1 ; and at least one of r or o is ⁇ 0.
  • antimicrobial agents (a) of formula (1) are used, wherein
  • X is oxygen, sulfur or -CH2-
  • Y is chloro or bromo, m is O, n is O or l ,
  • 0 is 1 or 2
  • r is 1 or 2
  • p is O
  • antimicrobial agent (a) is a compound of formula
  • Formula (3) shows the antimicrobial 2,4,4'-trichloro-2-hydroxydiphenyl ether, otherwise known as Triclosan.
  • Formula (4) shows the antimicrobial 4,4'-trichloro-2-hydroxydiphenyl ether, otherwise known as Diclosan.
  • Preferred phenol derivatives (b) correspond to formula
  • Rl is hydrogen, hydroxy, C-
  • R2 is hydrogen, hydroxy, C-
  • R3 is hydrogen, C-
  • 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-benzylphenoi, p-chloro-o-benzylphenol and 4-phenolsulfonic acid.
  • Typical antimicrobial agents (c) correspond to the formula wherein l , R2. R3. R4 and R5 are eacn independently of one another hydrogen or chloro.
  • Illustrative examples of compounds of formula (6) 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 Cs-C-i ⁇ cocamidopropylbetaine.
  • Amphoteric surfactants as antimicrobial agents (f) are suitably C-
  • Typical trihalocarbanilides which are usefull as antimicrobial agent (g) are compounds of the formula
  • Hal is chloro or bromo, n and m are 1 or 2, and the sum of n plus m equals 3.
  • quaternary and polyquaternary compounds which correspond to antimicrobial agent (h) include those of the formula wherein
  • R ⁇ and Rg are each independently of one another C-
  • Hal is chloro or bromo.
  • 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.
  • a combination of antimicrobial agents that provide antibacterial and antifungal activities are advantageous in that they provide the treated fibres with further functions such as antibacterial, antifungal, anti-dustmite and deodorising properties.
  • benzylimidazol derivatives for example those known as Protectol BCM, of the formula:
  • benzoate derivatives preferably benzyl benzoate:
  • the process uses a formulation which is compatible with the aqueous solution of cellulose and which also facilitates incorporation into the fibres.
  • the antimicrobial agents or antifungal agents which are used in the present process are water-soluble or only sparingly soluble in water. These compounds are therefore applied in dispersed form. To this end, they are milled with an appropriate surfactant, conveniently using quartz balls and an impeller, to a particle size of about 1 -2mm or less. Antimicrobial agents so prepared could then be made into stable formulations by the addition of suitable dispersing or emulsifying agents.
  • the antimicrobials, antifungals or mixtures thereof can be dissolved in a surfactant at a concentration ranging from 1 to 60%.
  • a homogeneous mixture can be formed when the formulation is added to the soluble form of the cellulose.
  • the incorporation can be achieved by diluting the antimicrobial and/or antifungal surfactant solution to form a dispersion which is pumped into the cellulose solution just before extrusion.
  • concentration of antimicrobials and/or antifungals ranges from 10g to 100g per litre of solution, preferably 40g to 60 g per litre of solution.
  • concentrated antimicrobial and/or antifungal surfactant solution is directly pumped into the cellulose solution just before extrusion. This process requires precise metering and also very good mixing as the amount of antimicrobial and/or antifungal being incorporated into the fibres is very small.
  • Suitable surfactants for use in the present process are:
  • acid esters or their salts of alkylene oxide adducts typically acid esters or their salts of a polyadduct of 4 to 40mol of ethylene oxide with 1mol of a phenol, or phosphated polyadducts of 6 to 30mol of ethylene oxide with 1 mol of 4-nonylphenol, 1mol of dinonylphenol or, preferably, with 1 mol of compounds which are prepared by addition of 1 to 3mol of unsubstituted or substituted styrenes to 1 mol of phenol, polystyrene sulfonates, fatty acid tau rides, alkylated diphenyl oxide mono- or disulfonates, sulfonates of polycarboxylates, the polyadducts of 1 to 60 mol of ethylene oxide and/or propylene oxide with fatty amines, fatty acids or fatty alcohols, each containing 8 to 22 carbon atoms in the alkyl chain, with alkylphenols containing 4 to 16 carbon
  • a preferred surfactant is a nonyl phenyl ether of the formula
  • the mixture is passed through the spinneret into the chemical baths, such as the coagulation bath which normally contain concentrated solutions of 5% to 15% sulfuric acid, preferably 7% to 12% sulfuric acid, where the regeneration of cellulose occurs.
  • the chemical baths such as the coagulation bath which normally contain concentrated solutions of 5% to 15% sulfuric acid, preferably 7% to 12% sulfuric acid, where the regeneration of cellulose occurs.
  • the antimicrobials and/or antifungals quickly precipitate and form particles of very small size within the cellulose fibres. These particles are difficult to remove from the fibres and are small enough to avoid spinneret blockage.
  • the formulation may be used in the incorporation of antimicrobials and/or antifungals into synthetic fibres, and blends thereof, which are produced by wet spinning processes.
  • Such fibres include rayon, cellulose acetate, cellulose triacetate, poly(vinyl chloride) and poly(acrylonitrile), or blends thereof.
  • the expected concentration of antimicrobial and/or antifungal in the fibres ranges from 0.1% to 3%, preferably 0.5% to 1%.
  • compositions used for the finishing process comprise an antimicrobial, or a mixture thereof, selected from the following:
  • surfactants selected from the following:
  • - acid esters or their salts of alkylene oxide adducts typically acid esters or their salts of a polyadduct of 4 to 40mol of ethylene oxide with 1 mol of a phenol, or phosphated polyadducts of 6 to 30mol of ethylene oxide with 1 mol of 4-nonylphenol, 1 mol of dinonylphenol or, preferably, with 1mol of compounds which are prepared by addition of 1 to 3mol of unsubstituted or substituted styrenes to 1 mol of phenol,
  • polyadducts of 1 to 60 mol of ethylene oxide and/or propylene oxide with fatty amines, fatty acids or fatty alcohols, each containing 8 to 22 carbon atoms in the alkyl chain, with alkylphenols containing 4 to 16 carbon atoms in the alkyl chain, or with trihydric to hexahydric alkanols containing 3 to 6 carbon atoms, which polyadducts are converted into an acid ester with an organic dicarboxylic acid or with an inorganic polybasic acid,
  • formaldehyde condensates such as condensates of ligninsulfonates and/or phenol and formaldehyde, condensates of formaldehyde with aromatic sulfonic acids, typically condensates of ditolyl ether sulfonates and formaldehyde, condensates of naphthalenesulfonic acid and/or naphthol- or naphthylaminesulfonic acids with formaldehyde, condensates of phenolsulfonic acids and/or sulfonated dihydroxydi- phenylsulfone and phenols or cresols with formaldehyde and/or urea, as well as condensates of diphenyl oxide-disulfonic acid derivatives with formaldehyde.
  • a preferred composition comprises 40g of a compound of formula (3) dissolved in 60g of a nonyl phenyl ether of the formula C 9 H 19 C 6 H 5 O(CH 2 CH 2 O) 1 oH.
  • composition may also additionally contain an antifungal agent.
  • concentration of the antimicrobial or antimicrobial/antifungal mixture ranges from 1 to 60%.
  • a further composition comprises an antifungal agent selected from the following:
  • alkylene oxide adducts typically acid esters or their salts of alkylene oxide adducts, typically acid esters or their salts of a polyadduct of 4 to 40mol of ethylene oxide with 1 mol of a phenol, or phosphated polyadducts of 6 to 30mol of ethylene oxide with 1 mol of 4-nonylphenol, 1 moI of dinonylphenol or, preferably, with 1 mol of compounds which are prepared by addition of 1 to 3mol of unsubstituted or substituted styrenes to 1 mol of phenol, polystyrene sulfonates, fatty acid taurides, alkylated diphenyl oxide mono- or disulfonates, sulfonates of polycarboxylates, the polyadducts of 1 to 60 mol of ethylene oxide and/or propylene oxide with fatty amines, fatty acids or fatty alcohols, each containing 8 to 22 carbon atoms in the alkyl chain
  • compositions may be diluted in order to form a dispersion, wherein the concentration of antimicrobial and/or antifungal is in the range of 10g to 10Og per litre, preferably in the range of 40g to 60g per litre.
  • concentration of antimicrobial and/or antifungal is in the range of 10g to 10Og per litre, preferably in the range of 40g to 60g per litre.
  • Example 1 Preparation of antimicrobial containing formulation
  • Formulation A 100 gram of Formulation A is added into an appropriate amount of water (deionised) to produce a 800ml formulation.
  • the resulting formulation (Formulation B) is a stable dispersion in which the concentration of Triclosan is 50g/litre.
  • Cellulose in its' soluble form is prepared by a conventional process. Hence, sized cellulose is treated with caustic soda, oxidising and sulfonating agent and solublilised/pulverised to form aqueous solution followed by filtration and degassing. Soluble cellulose prepared as such is ready to be spun to form fibres.
  • Formulation B is injected by a diaphragm pump into the main pipeline in which the soluble rayon is being transported to the spinneret for extrusion.
  • the mixture of Formulation B and soluble rayon is further mixed in the pipe to improve homogeneity before it is extruded from the spinneret to form fibres.
  • the pumping speed is adjusted as such that the resulting expected concentration of Triclosan in the fibres is in the range of 0.5 to 1 %.
  • the so-formed fibre is allowed to pass into a coagulation bath comprised of 10% sulfuric acid and then a stretching bath comprised of 1 % sulfuric acid in which coagulation and stretching take place followed by desulfonation, washing, oiling and drying.
  • the extract is then used for reversed phase High Performance Liquid Chromatography analysis under the following conditions:
  • Solvent 50% Solvent A(acetonitrile) : 50% Solvent B(water), 100% solvent A at 20 minutes
  • the agar diffusion test is used to determine the bacteriostatic or fungistatic activity of an antimicrobial agent or a product which contains an antimicrobial or has been treated with an antimicrobial agent.
  • the treated material (usually in the form of discs) is applied on inoculated agar plates. During the incubation phase, the active substance can diffuse into the agar and inhibit the bacterial growth. Poorly diffusing products should at least be able to inhibit the bacterial growth under the disc.
  • the described agar diffusion test is based on the method AATCC 90-1974.
  • Other methods which are based on diffusion / inhibition principle are:
  • 0.05g of the fibres are applied on the top layer of the solidified agar containing the bacteria.
  • a 1 :100 (Staphylococcus aureus) and 1 :1000 (Escherichia coli and Proteus vulgaris) dilution are made and 3.5ml of the dilutions are added to 500ml agar.
  • Test bacteria Staphylococcus aureus ATCC 9144
  • Casein soy meal pepton agar two layers of agar: 15 ml bottom layer without germs and 5 ml top layer with bacteria
  • Vinson rating is described by L.J. Vinson et al. J.Pharm. Sci. 50, 827-830, 1961
  • rayon fibres with antimicrobial Triclosan can inhibit the growth of microorganisms on the surface of the fibres (measured by the vinson rating) as well as provide a zone of inhibition around the fibres where the growth of microorganisms is inhibited due to the presence of small amounts of Triclosan which is diffused from the fibres.
  • Example 6 Preparation of anti-fungal formulations
  • Anionic surfactant 30%
  • Compound (15) is also used to prepare a formulation which contains anionic surfactant, nonionic dispersant, small amount of organic solvent, water and a compound of formula (3) in the following proportions:
  • Anionic surfactant 30%
  • Formulation C1 100 gram of Formulation C1 is added into an appropriate amount of water (deionised) to produce a 800ml formulation.
  • the resulting formulation (Formulation C2) is a stable dispersion in which the concentration of antifungal substance of formula (15) is 50g/litre.
  • Cellulose in its' soluble form is prepared by a conventional process. Hence, sized cellulose is treated with caustic soda, oxidising and sulfonating agent and solublilised/pulverised to form aqueous solution followed by filtration and de-gasing. Soluble cellulose prepared as such is ready to be spun to form fibres.
  • Formulation C2 is injected by a diaphragm pump into the main pipeline in which the soluble rayon is being transported to the spinneret for extrusion.
  • the mixture of Formulation B and soluble rayon is further mixed in the pipe to improve homogeneity before it is extruded from the spinneret to form fibres.
  • the pumping speed is adjusted as such that the resulting expected concentration of substance (15) in the fibres is in the range of 0.5 to 1 %.
  • the so-formed fibre is allowed to pass into an coagulation bath comprised of 10% H 2 SO 4 and then a stretching bath comprised of 1% H 2 SO 4 in which coagulation and stretching take place followed by desulfonation, washing, oiling and drying.
  • the agar diffusion test is used to determine the bacteriostatic or fungistatic activity of an antimicrobial agent or a product which contains an antimicrobial or has been treated with an antimicrobial agent.
  • the treated material (usually as discs) is applied on inoculated agar plates. During the incubation phase, the active substance can diffuse into the agar and inhibit the bacterial growth. Poorly diffusing products should at least be able to inhibit the bacterial growth under the disc.
  • the described agar diffusion test is based on the method AATCC 90-1974. Other methods which are based on diffusion / inhibition principle are:
  • 0.05g of the fibres are applied on the top layer of the solidified agar containing the bacteria.
  • a 1 :100 (Staphylococcus Aureus) dilution are made and 3.5ml of the dilutions are added to 500ml agar.
  • 4ml of spore suspension of the fungi are mixed with 500ml molten agar at 47°C.
  • Such preparations are aimed to achieve an end concentration of the bacteria in the agar at around 10 4 cfu/ml.
  • Test bacteria Staphylococcus aureus ATCC 9144
  • Nutrient medium Casein soy meal pepton agar (two layers of agar: 15 ml bottom layer without bacteria and 5 ml top layer with bacteria)
  • Formulation D1 100 gram of Formulation D1 is added into an appropriate amount of water (deionised) to produce a 800ml formulation.
  • the resulting formulation (Formulation D2) is a stable dispersion in which the concentration of compound (15) as well as compound (3) is 50g/litre.
  • Example 11 Preparation of antimicrobial containing ravon fibres
  • Cellulose in its' soluble form is prepared by a conventional process. Hence, sized cellulose is treated with caustic soda, oxidising and sulfonating agent and solublilised/pulverised to form aqueous solution followed by filtration and degasing. Soluble cellulose prepared as such is ready to be spun to form fibres.
  • Formulation D2 is injected by a diaphragm pump into the main pipeline in which the soluble rayon is being transported to the spinneret for extrusion.
  • the mixture of Formulation D2 and soluble rayon is further mixed in the pipe to improve homogeneity before it is extruded from the spinneret to form fibres.
  • the pumping speed is adjusted as such that the resulting expected concentration of substance D2 and Triclosan in the fibres is in the range of 0.5 to 1 %.
  • the so-formed fibre is allowed to pass into an coagulation bath comprised of 10% H 2 SO and then a stretching bath comprised of 1% H 2 SO 4 in which coagulation and stretching take place followed by desulfonation, washing, oiling and drying.
  • Example 12 Antimicrobial efficacy of ravon fibres treated with Compound (15) and Compound (3)
  • the agar diffusion test is used to determine the bacteriostatic or fungistatic activity of an antimicrobial agent or a product which contains an antimicrobial or has been treated with an antimicrobial agent.
  • the treated material (usually as discs) is applied on inoculated agar plates. During the incubation phase, the active substance can diffuse into the agar and inhibit the bacterial growth. Poorly diffusing products should at least be able to inhibit the bacterial growth under the disc.
  • the described agar diffusion test is based on the method AATCC 90-1974.
  • Other methods which are based on diffusion / inhibition principle are: - SNV 195'920; Testing the antibacterial effect of textiles and other materials with the help of agar diffusion tests (1976).
  • 0.05g of the fibres are applied on the top layer of the solidified agar containing the bacteria.
  • a 1 :100 (Staphylococcus Aureus) dilution are made and 3.5ml of the dilutions are added to 500ml agar.
  • 4ml of spore suspension of the fungi are mixed with 500ml molten agar at 47°C.
  • Such preparations are aimed to achieve an end concentration of the bacteria in the agar at around 10 4 cfu/ml.
  • Test bacteria Staphylococcus aureus ATCC 9144 Trichophyton mentagrophytes ATCC 9553 Aspergnis niger ATCC 6275
  • Nutrient medium Casein soy meal pepton agar ( two layers of agar: 15 ml bottom layer without bacteria and 5 ml top layer with bacteria)
  • Vinson rating is described by L.J. Vinson et al. J.Pharm. Sci. 50, 827-830, 196
  • Results indicate that the rayon fibres treated with compound (15) and compound (3) show good antimicrobial activity against both fungi and bacteria.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé de finition de fibres de cellulose régénérées, à l'aide d'un agent anti-microbien et/ou d'un agent antifongique ou d'un mélange des deux. Ledit procédé consiste à ajouter un agent anti-microbien et un ou plusieurs agents tensio-actifs à la forme soluble des fibres, avant leur régénération; et à extruder ledit mélange d'une filière, de sorte que la fibre régénérée soit formée. Les fibres traitées selon le procédé de l'invention présentent une bonne activité anti-microbienne et antifongique.
EP99952595A 1998-10-29 1999-10-18 Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres Withdrawn EP1141453A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99952595A EP1141453A1 (fr) 1998-10-29 1999-10-18 Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP98811085 1998-10-29
EP98811085 1998-10-29
PCT/EP1999/007875 WO2000026447A1 (fr) 1998-10-29 1999-10-18 Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres
EP99952595A EP1141453A1 (fr) 1998-10-29 1999-10-18 Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres

Publications (1)

Publication Number Publication Date
EP1141453A1 true EP1141453A1 (fr) 2001-10-10

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EP99952595A Withdrawn EP1141453A1 (fr) 1998-10-29 1999-10-18 Incorporation d'agents antimicrobiens organiques dans des fibres au cours d'un procede de filature de fibres

Country Status (6)

Country Link
EP (1) EP1141453A1 (fr)
KR (1) KR20010087382A (fr)
CN (1) CN1325462A (fr)
AU (1) AU6473499A (fr)
TR (1) TR200101052T2 (fr)
WO (1) WO2000026447A1 (fr)

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EP0937812A2 (fr) 1998-02-20 1999-08-25 Ciba SC Holding AG Procédé de traitement des non-tissés avec des agent antimicrobiens
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BR0311638B1 (pt) * 2002-06-07 2013-04-16 chapa artificial para revestimento de parede antimicrobiana, seu mÉtodo de produÇço, composiÇço antimicrobiana, bem como papel, pasta fluida de gipso solidificada e chapa artificial para revestimento de parede compreendendo a referida composiÇço.
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MX2012011708A (es) * 2010-04-08 2013-02-27 List Holding Ag Procemiento para la fabricacion de un producto.

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CN1325462A (zh) 2001-12-05
WO2000026447A1 (fr) 2000-05-11
KR20010087382A (ko) 2001-09-15
TR200101052T2 (tr) 2001-08-21
AU6473499A (en) 2000-05-22

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