Classifications

• • 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
  • C08K5/04—Oxygen-containing compounds
  • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
  • A01N59/16—Heavy metals; Compounds thereof
• • 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
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/015—Biocides

Definitions

• the present invention is aimed at antimicrobial polyolefin and polyester compositions, for example polyolefin and polyester films, fibers or molded parts.
• the polyolefins and polyesters are provided outstanding permanent antimicrobial activity via the incorporation therein of a combination of a silver antimicrobial additive and a certain wettability additive.
• Glass supported silver is disclosed for example in U.S. app. No. 2005/0233888.
• WO2006/051048 teaches antimicrobial polymer compositions.
• polyolefin or polyester compositions with durable antimicrobial activity comprising
• a silver antimicrobial and a wettability additive selected from the group consisting of ethoxylated alcohols and alkyl metal sulfonates.
• a silver antimicrobial and a wettability additive selected from the group consisting of ethoxylated alcohols and alkyl metal sulfonates.
• the silver antimicrobial may be any known antimicrobial form of silver. It may for example be silver supported on a zeolite, silver supported on a glass, elemental silver, micro or nano scaled elemental silver, elemental silver dispersed in silicone oil (polymethyldisiloxane), silver chloride, silver nitrate, silver sulfate, silver phosphate, silver zirconate, or silver apatite.
• silicone oil polymethyldisiloxane
• silver chloride silver nitrate, silver sulfate, silver phosphate, silver zirconate, or silver apatite.
• Silver supported on a zeolite is for example taught in U.S. Pat. Nos. 4,775,585;
• a zeolite is generally aluminosilicate having a three dimensional grown skeleton structure and is generally represented by xM 2 /n « 0AI 2 03*ySi0 2 *H 2 0, written with AI 2 O3 as a basis, wherein M represents an ion-exchangeable metal ion, which is usually the ion of a monovalent or divalent metal; n corresponds to the valence of the metal; x is a coefficient of the metal oxide; y is a coefficient of silica; and z is the number of water of crystallization.
• the zeolites of the present invention have a specific surface area of at least 150m 2 /g.
• the present zeolites support antimicrobial silver, that is silver is retained at the ion-exchangeable sites of the zeolite.
• the silver supported on a zeolite may be a surface-modified silver supported zeolite according to U.S. Pat. No. 6,071 ,542.
• the silver supported on glass may also include zinc, that is it may be silver glass or silver zinc glass.
• Glass supported silver is taught for example in U.S. Pat. Nos. 5,049,139 and 6,143,318 and published U.S. application No. 2005/0233888, the disclosures of which are hereby incorporated by reference.
• the elemental silver may be for example micro scaled or nano scaled.
• Nano scaled antibacterial silver is disclosed in U.S. Pat. No. 6,822,034, the relevant disclosure of which is hereby incorporated by reference.
• Nano scaled silver is also taught in U.S. Pat. No. 6,984,392, the disclosure of which is also incorporated by reference.
• the amount of silver employed is for example from about 0.001 to about 15 weight percent silver, based on the weight of the polyolefin or polyester.
• the amount of silver employed is from about 0.005 to about 5.0 weight percent silver or from about 0.005 to about 1.0 weight percent silver, based on the weight of the polyolefin or polyester.
• the amount of silver employed is about 0.01 , about 0.05 or about 0.1 percent by weight silver based on the weight of the polyolefin or polyester.
• the amount of elemental silver employed is from about 0.01 to about 5.0 weight percent, based on the weight of the.
• the amount of elemental silver employed is from about 0.01 to about 2.0 weight percent or from about 0.01 to about 1.0 weight percent, based on the weight of the polymer.
• the amount of supported silver employed is for example from about 0.001 to about 0.2 weight percent, based on the weight of the polymer.
• the amount of supported silver employed is from about 0.01 to about 0.2 weight percent or from about 0.05 to about 0.2 weight percent, based on the weight of the polymer. These weight levels are based on the silver.
• the silver employed may be some mixture of the forms of antimicrobial silver discussed above.
• antimicrobials may also be employed in the present compositions, for instance
• the silver antimicrobial may be replaced with other known antimicrobials such as 2-phenyl phenol, 2.4.4'-trichlor-2'- hydroxydiphenylether, 4,4'-dichlor-2-hydroxydiphenylether, 2,2'-methylenbis-(4-chloro- phenol), 4-(2-t-butyl-5-methylphenoxy)-phenol, 3-(4-chlorophenyl)-1 -(3,4-dichloro-phenyl)- urea or 2,4,6-trichlorophenol.
• other known antimicrobials such as 2-phenyl phenol, 2.4.4'-trichlor-2'- hydroxydiphenylether, 4,4'-dichlor-2-hydroxydiphenylether, 2,2'-methylenbis-(4-chloro- phenol), 4-(2-t-butyl-5-methylphenoxy)-phenol, 3-(4-chlorophenyl)-1 -(3,4-dichloro-phenyl)- urea or 2,
• alkyl metal sulfonates are of the formula RSO3M,
• M is Na, K or Li and R is straight or branched chain alkyl of 6 to 32 carbon atoms or is straight or branched chain alkenyl of 6 to 32 carbon atoms.
• M is Na, K or Li and R is straight or branched chain alkyl of 12 to 15 carbon atoms or is straight or branched chain alkenyl of 12 to 18 carbon atoms.
• Alkyl is a branched or unbranched radical, for example 1-methylpentyl, 1 ,3- dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1 ,1 ,3,3-tetramethylbutyl, 1- methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1 ,1 ,3-trimethylhexyl, 1 ,1 ,3,3- tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1 ,1 ,3,3,5,5- hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, icosyl or
• Alkenyl is an unsaturated version of alkyl, for example hexenyl, heptenyl, and the like.
• the ethoxylated alcohols are of the formula
• the term "a” is for example 6, 7, 8, 9, 10, 11 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24 or 25.
• the term “b” is for example every integer from 1 to 100, for example 1 , 2, 3, 4, 5, 6, 7, 8, 9, or 10, etc.
• the term “b” is for example from 1 to 10.
• the present wettability additives are present from about 0.001 % to about 15% by weight, based on the weight of the polyolefin or polyester. For instance, the wettability additives are present from about 0.1% to about 10% by weight, from about 1 % to about 8% by weight, or from about 1 % to about 7% by weight, based on the weight of the polyolefin or polyester.
• the polyolefins or polyesters may be in any form, for example fibers, filaments, films or molded parts.
• a preferred composition is a woven or nonwoven fabric. These may be for example woven or nonwoven polyolefin or polyester fabrics.
• the present methods produce for example fibers or filaments which are knitted, woven or bonded into knit, woven or nonwoven fabrics.
• the present melt extrusion methods form fibers or filaments.
• the fibers or filaments are formed by extrusion of the molten polymer through small orifices.
• the fibers or filaments thus formed are then drawn or elongated to induce molecular orientation and affect crystallinity, resulting in a reduction in diameter and an improvement in physical properties.
• nonwoven processes such as spunbonding and meltblowing, the fibers or filaments are directly deposited onto a foraminous surface, such as a moving flat conveyor and are at least partially consolidated by any of a variety of bonding means.
• Nonwoven fabrics may have a carded fiber structure or comprise a mat in which the fibers or filaments are distributed in a random array.
• the fabric may be formed by any one of numerous known processes including hydroentanglement or spun lace techniques, or by air laying or meltblowing filaments, batt drawing, stitchbonding, etc., depending upon the end use of the article to be made from the fabric.
• the invention is also applicable to melt extruded bi-component fibers, wherein one of the components is a polyolefin or a polyester according to this invention.
• Spunbond filament sizes most useful for fabrics of the anticipated type are from about 1.0 to about 3.2 denier.
• Meltblown fibers typically have a fiber diameter of less than 15 microns and most typically for the anticipated applications are fiber diameters less than 5 microns, ranging down to the submicron level.
• Webs in a composite construction may be processed in a wide variety of basis weights.
• Polyolefin fibers are typically extruded at temperatures in the range of from about 210° to about 24O 0 C. Polyolefin fiber spinning may by performed at a temperature of up to about 300°C. Polyester fibers are typically extruded at temperatures in the range of from about 285° to about 300°C.
• antimicrobial silver and a certain ethoxylated alcohol or a certain alkyl metal sulfonate are incorporated into a polyolefin or a polyester in the melt, which is extruded into for example pellets or granules or ultimately fibers, films or molded articles.
• the present silver additives and wettability additives may be compounded with the polymer pellets which are to be melt extruded.
• the additives may be preformulated or compounded into a polymer which may also contain small amounts of inorganic powder such as talc, and/or other traditional stabilizers.
• the mixing of the present silver and wettability additives into the polyolefin or polyester polymer is done by mixing them into molten polymer by commonly used techniques such as roll-milling, mixing in a Banbury type mixer, or mixing in an extruder barrel and the like.
• the heat history time at which held at elevated temperature
• the present additives can also be added substantially simultaneously or sequentially with any other additives which may be desired in certain instances.
• the present additives may also be pre-blended with other additives and the blend then added to the polymer. It is contemplated that in some instances the present additives may have the additional benefit of aiding other additives to become more easily or evenly dispersed or dissolved in the polymer. For easier batch-to-batch control of quality, it may be preferred to employ concentrated masterbatches of polymer/additive blends which are subsequently blended, as portions, to additional quantities of polymer to achieve the final desired formulations.
• the masterbatch, or the neat additives may be injected into freshly prepared polymer while the polymer is still molten and after it leaves the polymerization vessel or train, and blended therewith before the molten polymer is chilled to a solid or taken to further processing.
• the present masterbatches contain the silver antimicrobial additive and the wettability additive in concentrations of for example from about 1 % to about 75%, from about 2% to about 50% or from about 5% to about 40% by weight, based on the weight of the polyolefin or polyester.
• the incorporation of the present antimicrobial silver additives and wettability additives provides for permanent antimicrobial activity. That is, the present polyolefins and polyesters have durable antimicrobial activity, such that the fibers, films or molded parts made therefrom do not lose their antimicrobial activity upon aging or handling.
• the antimicrobial activity is stable to repeated insults, without a loss of performance, even over extended time periods.
• the present invention is aimed for example at nonwoven polyolefin or polyester fabrics. It is also aimed at threads or yarns for weaving or knitting in conventional textile processes.
• the additives of the present invention are effective irrespective of other factors that influence the properties of nonwoven fabrics, for example, basis weight, fiber diameter, degree and type of bonding of the fibers, and the synergistic effects and influence of composite structures.
• the present invention is not limited to single component fibers.
• Polyolefin or polyester bi-component fibers, particularly side-by-side or sheath-core fibers of polyolefin or polyester would be expected to demonstrate the same practical benefits as single component fibers of either type. It would be particularly efficacious to include the melt additives only in a single component.
• the antimicrobial fabrics produced from the fibers or filaments of this invention are particularly useful, for example, as the skin contacting inner lining fabric of sanitary articles, particularly single use diapers, training pants, feminine hygiene products or incontinence care products.
• the fabrics also have utility in wet and dry wipes, wound dressings, surgical gowns, surgical masks, filters, textiles for hospital environments, and the like.
• a further preferred embodiment is composition according to the invention which is a molded part.
• a further preferred embodiment is a composition of the invention in the form of a film.
• Antimicrobial films are employed for example as food packaging.
• the fabrics of the present invention may be sterilized by exposure to about 0.5 to about 10 megarads of gamma irradiation. Sterilization with gamma irradiation is employed for hospital garments and the like.
• the polyester has dicarboxylic acid repeat units selected from the group consisting of aromatic dicarboxylic acids having 8 to 14 carbon atoms, aliphatic dicarboxylic acids having 4 to 12 carbon atoms, cycloaliphatic dicarboxylic acids having 8 to 12 carbon atoms, and mixtures thereof.
• diacids are terephthalic acid, isophthalic acid, o-phthalic acid, naphthalene dicarboxylic acid, cyclohexane dicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4'-dicarboxylic acid, succinic acid, maleic acid, glutaric acid, adipic acid, sebacic acid and mixtures thereof.
• diacids are terephthalic acid, isophthalic acid and 2,6-naphthalene dicarboxylic acid.
• the diol or glycol portion of the polyester are derived from the generic formula HO-G- OH where G is an aliphatic, cycloaliphatic or aromatic moiety of 2 to 18 carbon atoms.
• G is an aliphatic, cycloaliphatic or aromatic moiety of 2 to 18 carbon atoms.
• diols or glycols are ethylene glycol, diethylene glycol, triethylene glycol, propane-1 ,3-diol, propane-1 ,2-diol, butane-1 ,4-diol, pentane-1 ,5-diol, hexane-1 ,6-diol, 1 ,4-cyclohexanedimethanol, 3-methylpentane-2,4-diol, 2-methylpentane1 ,4-diol, 2,2-diethyl- propane-1 ,3-diol, 1 ,4-di-(hydroxyethoxy)benzene, 2,
• the diol is for example ethylene glycol or 1 ,4-cyclohexanedimethanol.
• the polyester is for example poly(ethylene terephthalate) PET or polybutylene terephthalate or poly(ethylene 2,6-naphthalene-2,6-dicarboxylate) PEN.
• polyester can also be a blend of polyesters or copolyesters including components mentioned above.
• polystyrene resins examples are:
• Polymers of monoolefins and diolefins for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).
• HDPE high density polyethylene
• HDPE-HMW high density and high molecular weight polyethylene
• HDPE-UHMW high density and ultrahigh molecular weight polyethylene
• MDPE medium density polyethylene
• LDPE low density polyethylene
• LLDPE linear low density poly
• Polyolefins i.e. the polymers of monoolefins exemplified in the preceding paragraph, for example polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
• a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table.
• These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either p- or s-coordinated.
• These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(lll) chloride, alumina or silicon oxide.
• These catalysts may be soluble or insoluble in the polymerization medium.
• the catalysts can be used by themselves in the polymerization or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, Na and/or Ilia of the Periodic Table.
• the activators may be modified conveniently with further ester, ether, amine or silyl ether groups.
• These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
• Copolymers of monoolefins and diolefins with each other or with other vinyl monomers for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers and their copolymers with carbon monoxide or ethylene/acrylic acid copolymers and their salts (iono
• Polyolefins of the present invention are for example polypropylene homo- and copolymers and polyethylene homo- and copolymers.
• polypropylene high density polyethylene (HDPE), linear low density polyethylene (LLDPE) and polypropylene random and impact copolymers.
• HDPE high density polyethylene
• LLDPE linear low density polyethylene
• the present polyolefin or polyester fibers, films or molded parts may also have incorporated therein or applied thereto appropriate additives such as ultraviolet light absorbers, hindered amine light stabilizers, antioxidants, processing aids and other additives.
• compositions may further comprise one or more additives selected from the group consisting of hindered phenolic antioxidants, organic phosphorus stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, hindered amine light stabilizers and hydroxylphenyltriazine, hydroxyphenylbenzotriazole or hydroxybenzophenone ultraviolet light absorbers.
• additives selected from the group consisting of hindered phenolic antioxidants, organic phosphorus stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, hindered amine light stabilizers and hydroxylphenyltriazine, hydroxyphenylbenzotriazole or hydroxybenzophenone ultraviolet light absorbers.
• the present present polyolefin or polyester material may optionally contain from about 0.01 to about 10 %, preferably from about 0.025 to about 5 %, and especially from about 0.1 to about 3 % by weight of one or more such further stabilizers or additives, based on the weight of the polymeric material.
• the wettability additive employed is a mixture of ethoxylated alcohols CH 3 CH 2 (CH 2 CH 2 ) a CH 2 CH 2 (OCH 2 CH 2 ) b OH where a is 13 and b is 2 and 3.
• the silver antimicrobial employed is nano scaled elemental silver.
• the following polypropylene (PP) formulations are prepared.
• the parts per million (ppm) and weight percents are by weight based on PP:
• Test strains staphylococcus aureus ATCC 9144 escherichia coli NCTC 8196
• Neutralizer phosphate buffer 0.07 molar, pH 7.4 containing 1 % tween 80 and 0.3% lecithin (10ml_/sample)
• Dilution media sterile deionized water, pH 7.4
• Continuous polypropylene miltifilament fibers are prepared using a fiber spinning line under the following conditions: Extruder temperature of 24O 0 C, 40 filaments. Spinning pump speed is adjusted to produce fibers with a specific weight of 2.0 dpf. The fibers are knitted into socks.
• Samples (2 discs with 40mm diameter) are cut and put in sterile Petri dishes. The test samples are then inoculated with 0.5 ml. of the diluted bacterial suspension in NaCI
• samples 1 and 2 Immediately after inoculation (samples 1 and 2) and after 24 hours at 37 0 C, all inoculated samples are shaken for 1 minute in 10 ml. phosphate buffer in order to re- suspend the test microorganisms from the samples (stomacher 80).
• samples 1 and 2 until 10 "4 are prepared in sterile deionized water. From the undiluted sample and from the dilutions, samples of lOO ⁇ L are plated out on agar plates by means of a spiral plater. After incubation of the inoculated agar plates, the colonies are counted and reported as cfu/sample.
• Samples 1 and 2 are taken for the calculation of log reductions after 24 hours contact time.
• the PP socks are washed under the following conditions:
• Liquor ratio 6:1 (this means 6 liter of drinking tap water / kg textile) 20 minutes at 40 0 C
• Staphylococcus aureus ATCC 9144 log reduction as a function of washing cycle
• the bacterial activity is excellent (above 5 log reduction) with all samples containing at least 500 ppm elemental silver. However, the effect is not durable to washing cycles without the presence of an ethoxylated alcohol additive. The presence of an ethoxylated alcohol additive clearly provides a more durable antimicrobial activity.
• the wettability additive employed is a 1 to 1 weight mixture of ethoxylated alcohols CH 3 CH 2 (CH 2 CH 2 ) a CH 2 CH 2 (OCH 2 CH 2 ) b OH where a is 13 and b is 2 and 3 to a stearyl 2 mole ethoxylate.
• the silver antimicrobial employed is micron scaled elemental silver or zeolite supported ionic silver.
• PP polypropylene
• test samples are prepared by incorporating the antimicrobial silver into polypropylene substrate using a Brabender ball mixer, followed by compression molding at 372°F/6 minutes.
• the test method is JISZ 2801.
• Test Strains Escherichia coli ATCC 10536 Material: sterile petri dishes (90 mm and 55 mm) sterile disposable pipettes 1 ml & 100 ⁇ l sterile glass pipettes sterile test tubes PE films (4 x 4 cm) or substitute humid/vacuum chamber
• Culture medium for preparation of bacterial inoculum Nutrient broth: beef extract 3.O g peptone 10 g sodium chloride 5.0 g distilled water 100O mL
• Inactivation medium SCDLP broth: casein peptone 17 g soybean peptone 3.0 g sodium chloride 5.0 g disodium hydrogen phosphate 2.5 g glucose 2.5g lecithin 1.0 g distilled water 100O mL
• Dilution medium Phosphate buffered physiological saline
• Plate count agar for determination of bacterial cell count and preparation of inoculum yeast extract 2.5 g tryptone 5.O g glucose 1.0 g agar 15 g purified water 100O mL
• Casein-soy meal peptone-agar for determination of bacterial cell count of the inoculum
• test piece (5 x 5 cm) is placed with the test surface up in the middle of a sterile petri dish.
• Samples are inoculated with 0.4 ml bacterial solution in 1/500 nutrient broth diluted in deionized water (resulting in a final concentration of ⁇ 10 5 cfu) and covered with a film.
• Two sample specimens per antimicrobial surface are inoculated and incubated in a humid chamber at 37°C for 24h.
• the detection limit of this method is ⁇ 10 cells/sample if no bacteria colony appears on the plate of the undiluted suspension.
• the initial value at 0 h is determined with the untreated samples without any antimicrobial properties.
• the inoculum is distributed on the sample, covered with a film and immediately 10 ml. inactivation buffer is added. 1 ml. is transferred to a sterile petri dish and 15-20 ml. plate count agar is added.
• st growth strong growth
• the bacterial activity is excellent (above 4 log reduction) with all samples containing 1 % zeolite supported silver and 1.8% ethoxylated alcohol.
• the presence of an ethoxylated alcohol additive clearly provides a strong synergistic antimicrobial activity.
• the bacterial activity is excellent (above 4 log reduction) with all samples containing either form of silver plus 2% sodium alkyl sulfonic acid salt.
• the presence of a sodium alkyl sulfonic acid salt additive clearly provides a strong synergistic antimicrobial activity.
• the efficacy test employed is as in Nature Medicine, Vol. 6, No. 8, September, 2000. p. 1053.
• the bacterial activity is strong (12.1 h) with the samples containing 2% elemental silver plus 2% sodium alkyl sulfonic acid salt.
• the presence of a sodium alkyl sulfonic acid salt additive clearly provides a synergistic antimicrobial activity.
• the bacterial activity is strong (12.1 h) with the samples containing either silver plus 2% sodium alkyl sulfonic acid salt.
• the presence of an sodium alkyl sulfonic acid salt additive clearly provides a synergistic antimicrobial activity.

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• Chemical & Material Sciences (AREA)
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• Chemical Kinetics & Catalysis (AREA)
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• Polymers & Plastics (AREA)
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• 2008
  • 2008-05-30 WO PCT/EP2008/056694 patent/WO2008151948A2/en not_active Ceased
  • 2008-05-30 ES ES08760282.7T patent/ES2522616T3/es active Active
  • 2008-05-30 CA CA002689201A patent/CA2689201A1/en not_active Abandoned
  • 2008-05-30 EP EP08760282.7A patent/EP2155815B1/en not_active Not-in-force
  • 2008-05-30 JP JP2010511576A patent/JP5631205B2/ja not_active Expired - Fee Related
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  • 2008-06-09 US US12/157,278 patent/US20080306183A1/en not_active Abandoned
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