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WO1999008527A1 - Compositions pour le traitement d'apret antimicrobien de textiles et de matieres plastiques, et utilisation de ces compositions - Google Patents

Compositions pour le traitement d'apret antimicrobien de textiles et de matieres plastiques, et utilisation de ces compositions Download PDF

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Publication number
WO1999008527A1
WO1999008527A1 PCT/CH1998/000341 CH9800341W WO9908527A1 WO 1999008527 A1 WO1999008527 A1 WO 1999008527A1 CH 9800341 W CH9800341 W CH 9800341W WO 9908527 A1 WO9908527 A1 WO 9908527A1
Authority
WO
WIPO (PCT)
Prior art keywords
antimicrobial
woven
tetrachloro
methylsulfonyl
composition according
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.)
Ceased
Application number
PCT/CH1998/000341
Other languages
German (de)
English (en)
Inventor
Walter Bender
Erich Rohrbach
Peter Stutte
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.)
Sanitized AG
Original Assignee
Sanitized 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 Sanitized AG filed Critical Sanitized AG
Priority to AU86207/98A priority Critical patent/AU8620798A/en
Publication of WO1999008527A1 publication Critical patent/WO1999008527A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings

Definitions

  • compositions for the antimicrobial finishing of textiles and plastics and their use are provided.
  • the invention relates to antimicrobial liquid compositions or formulations with in part additional mite protection for woven and non-woven textiles and plastics and contains 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine in dissolved form as an antimicrobial active ingredient either alone or in combination with other antimicrobial agents such as, for example, 2,4,4 ' trichloro-2'-hydroxydiphenyl ether and / or acaricidal agents such as 3-phenoxybenzyl- (1 R, S) -cis-trans-2,2-dimethyl -3- (2,2-dichlorovinyl) cyclopropane carboxylate.
  • the formulation also contains other components such as organic solvents.
  • an emulsifier system consisting of one or more surfactants, such as preferably a poly (ethyleneoxy) nonyiphenyl ether phosphate and a plasticizer, such as preferably a dipropylene glycol dibenzoate, can be included in the formulation.
  • surfactants such as preferably a poly (ethyleneoxy) nonyiphenyl ether phosphate
  • plasticizer such as preferably a dipropylene glycol dibenzoate
  • 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine (CAS number: 13108- 52-6) is manufactured by Zeneca and sold under the names Densil S 25, Densil S 100 and Densil DOP.
  • Densil S 100 Densil S 100
  • Densil DOP Densil DOP
  • PVC polyvinyl chloride
  • DOP dioctyl phthalate
  • the active ingredient 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine has excellent antimicrobial properties against many germs, in particular the product can be regarded as a very potent algicide and fungicide.
  • the germ Pseudomonas aeruginosa ATCC 15442 shows, in the agar diffusion test according to SN 195 920, already in its original state on a PVC film equipped with 0.3% Densil DOP, produced according to DIN 53 775, medium growth. This means that over 10% of the film pattern is covered with the germ. With the addition of 0.5% Densil DOP to a PVC film manufactured according to DIN 53 775, weak growth with the germ can still be determined. This means that up to 10% of the film pattern is covered with the germ. The antimicrobial effect of this pattern is at the limit of effectiveness.
  • the germ Pseudomonas aeruginosa attacks the plasticizers in PVC, it is particularly disadvantageous if this germ is not prevented from growing. - If a film, as described, is washed before the antimicrobial test or treated with ultraviolet light, the antimicrobial protection against the germ Pseudomonas aeruginosa ATCC 15442 breaks down into an even higher application concentration. Against the Aspergillus niger EMPA 18 germ (mold), a break-in of the antimicrobial
  • - Suspensions can separate during storage. - Suspensions are more difficult to incorporate homogeneously into a product than dissolved products.
  • 2,4,4'-Thchlor-2'-hydroxydiphenyl ether (CAS number: 3380-34-5) has been brought onto the market by the company Ciba Specialty Chemicals under the name Irgasan, depending on the quality, with various names below .
  • the product has excellent antimicrobial values against a large number of bacteria and in some cases quite good values against fungi.
  • the product has found an extremely wide range of technical applications in a wide range of conservation areas.
  • antimicrobially active substances for the application itself must be incorporated into a formulation in such a way that they are sprayed, sprayed, or pulled out using at least one of the customary methods used in finishing textiles, such as padding lazy, on the textile can be applied.
  • the application is usually carried out in an aqueous medium.
  • an antimicrobial formulation this practically means that it can be applied from water.
  • Such a formulation must be either soluble or suspendable in water. If it can be suspended, the suspension must be sufficiently stable that it can be applied to textiles in the usual way
  • compositions which contain active ingredients in concentrations as low as possible, which achieve a sufficient to excellent protective action against microbes, but which exert the least possible toxicity to mammals.
  • the active ingredients should be easy to dose and optimally distributed during use without losing their long-lasting effect.
  • compositions which contain 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine in dissolved form.
  • compositions for the antimicrobial finishing of woven and non-woven textiles or plastics as defined in the claim 1.
  • composition and “formulation” are used synonymously in the present document and mean a preparation of active substance (s) and auxiliary substance (s) with the aim of applying, distributing and unfolding the active substance in a manner that is optimally matched to the particular application enable.
  • compositions according to the present invention contain between 0.1 and 8% 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine in dissolved form, in an organic medium consisting of a solvent system which itself consists of a single or several solvents is built up, with or without an emulsifier system, either alone or in combination with other antimicrobial and / or acaricidal or insecticidal active ingredients.
  • Formulations have been found to be very effective which contain between 0.1 and 7% dissolved 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 0.1 to 10% 2,4,4'-T chlorine Contain -2'-hydroxydiphenyl ether.
  • formulations which, in addition to the dissolved 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, alone or in combination with other microbial compounds pyrethroids, are suitable Insecticide and / or acanzide included
  • compositions according to the present invention are solutions which contain 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine alone or in combination with other microbial and / or insecticidal or acantidally active compounds in a phosphoric acid ester in which all three Protons have been replaced by an organic residue, contained in dissolved form
  • the aforementioned formulations are used by metering them into plastics, preferably polyvinyl chloride or epoxy resins in concentrations of 0.2 to 5.0%, based on the final weight of the plastic, to the raw mass of the plastic and incorporating them mechanically Takes place, a typical application of a composition according to the ⁇ present invention based on polyurethane, by 0.2 to 5.0% of the formulation, based on the final weight of the plastic, incorporated, optionally added to the alcohol component before the condensation process and incorporated homogeneously or the melt of the finished plastic can be added
  • the organic solvent system used additionally contains a polymerized dihydric alcohol, preferably a polyethylene glycol
  • the emulsifier system contains an ethoxylated surfactant, such as preferably a poly (ethyleneoxy) nonylphenyl ether phosphate
  • the emulsifier system contains a plasticizer, such as preferably a dipropylene glycol dibenzoate
  • the ideally antimicrobial formulation contains between 0.1 and 8% 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyrid, 0.1 to 10% 2,4,4 ' -T ⁇ chlor -2'-hydroxyd ⁇ phenyl ether and 1 to 30% N-methylpyrrodon, 1-40% polyethylene glycol, preferably with an average molecular weight in the range from 400.5 to 40% poly (ethyleneoxy) nonylphenyl ether phosphate and 5 contains up to 40% dipropylene glycol dibenzoate It is important for the particularly ideal antimicrobial and good ⁇ administrable formulation to between 2.0 and 5.0% 2,3,5,6-tetrachloro - (methylsulfonyl) -pyr ⁇ d ⁇ n, 2.0 to 8.0% 2,4,4'-Tr ⁇ chlor-2'-hydroxydiphenyl ether and 10 to 20% N-methylpyrrolidone, 20-40% polyethylene glycol, preferably with an average molecular mass in the range of 400
  • a formulation which contains between 2.0 and 5.0% 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyr ⁇ d ⁇ n, 2.0 to 8.0% 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 0.5 to 5% 3-phenoxybenzyl- (1 R, S) -c ⁇ s-trans-2,2- dimethyl-3- (2,2-dichlorv ⁇ nyl) cyclopropane carboxylate and 10 to 20% N-methylpyrrolidone, 20-40% polyethylene glycol, preferably with an average molecular weight in the range of 400, 10 to 30% poly (ethyleneoxy) - contains nonylphenyl ether phosphate and 20 to 40% dipropylene glycol dibenzoate
  • the fibers are, based on the weight of the goods, 0.5 to 4%, preferably 0.5 to 3%, for example 1 Treated 5% of a formulation containing between 2.0 and 50% 2,3,5,6-tetrachloro-4- (methylsulfonyl) -py ⁇ d ⁇ n, 2.0 to 8.0% 2,4,4'-tr ⁇ chlor- 2'-hydroxyd ⁇ phenyl ether, 0.5 to 5% 3-phenoxybenzyl- (1 R, S) -c ⁇ s-trans-2 2-dimethyl-3- (2,2-d ⁇ chlorv ⁇ nyl) - cyclopropanecarboxylate and 10 to 20% N-methylpyrrolidone , 20-40%
  • the treatment is carried out by suspending 1 to 20% of the composition in water or together with other textile chemicals by padding, taking off, also in the dye bath or by spraying, or in the same concentration range, based on the dry weight of the finished textile, by working into a doctor blade mass and application to the textile by doctoring
  • the advantages of the formulations according to the invention compared to the formulations described above are - due to the dissolved form, they are very easy to handle during processing.
  • the formulations are easy to demand and to dose. They can easily be homogeneously mixed into the plastic mass, e.g. PVC plastisol or corresponding individual components of epoxy resins or polyurethane , incorporated - Sufficient to excellent protection against all germs that are in the plastic mass, e.g. PVC plastisol or corresponding individual components of epoxy resins or polyurethane , incorporated - Sufficient to excellent protection against all germs that are in the
  • MIC minimum inhibitory concentration
  • the PVC plastisol was produced based on the ISO standard 195-X10 1993 (E), i.e. 65 grams of PVC powder (Evipol MP 7764), 5 grams of titanium dioxide, 2 grams of stabilizer (Irgastab BZ 529) and 35 Grams of dioctyl phthalate are added and mixed in a dissolver for between 45 minutes and one hour. 1.5% of the formulation according to the invention and described above are added to this mixture. The mixture is homogenized by stirring, poured onto a release paper to a layer thickness of 1 millimeter and coated for Heated at 170 ° C for 5 minutes. The antimicrobial activity of the film thus produced is tested as described above.
  • the Xenon test 450 After a soak of 720 hours at 20 ° C and a water throughput of 15 liters per hour and after a UV exposure test, the Xenon test 450, after 100, 200 and 400 hours the antimicrobial effect tested.
  • the antibacterial effect against d en Germ Pseudomonas aeruginosa, strain ATCC 15442 and the antifungal activity against the Streptoverticil germ by waksmann, strain DSM 40464 measured The agar diffusion test for determining the antifungal activity against Aspergillus niger, strain EMPA 18, shows a weak growth of less after watering as 10% of the pattern against all other germs, the patterns are both after the UV exposure test and after the watering adequate to excellent protection.
  • the Yelowness Index (Yl) increases slightly and the degree of whiteness (CIE) decreases slightly. However, both values change significantly in the test period below the tolerated five units.
  • Example a 30 grams of the formulation from Example a) are made up to 1 liter with water with stirring, giving a milky, very fine suspension. This suspension has a pH of 3.1 and is weighted onto cotton gabardme by means of the padding method per square meter of 198 grams, applied in a liquor to tissue ratio of 0.7 to 1
  • the cloth is dried in the tenter for two minutes at 120 ° C
  • the clamping frame can be fixed for 30 seconds without the antimicrobial values being adversely affected
  • Textiles made from natural, synthetic or mixed fibers are finished using one of the usual methods, for example by padding with, for example, 1.5% of a formulation as described in Examples a) and b).
  • the finished textile is dried and thermally fixed textile finished in this way, with a liquor ratio of 1 30, for 25 minutes at 40 ° C in tap water, which is mixed with two grams per liter of ECE color fastness test detergent has been washed, rinsed cold for six minutes, spun and dried in the stenter at ⁇ 80 ° C.
  • the pattern dried in this way is checked for the antimicrobial effect in the agar diffusion test.
  • Polyester fabric (Trevira, 248 grams per square meter) shows an inhibition zone of 2 millimeters after washing five times in an agar diffusion test against Staphylococcus aureus, strain ATCC 6538.
  • strain EMPA 18 Against Aspergillus niger, strain EMPA 18, the sample is covered with less than 10% after five washing cycles. This proportion of vegetation is the limit of effectiveness. The same result is achieved against Trichophyton mentagrophytes, strain EMPA 334.
  • the antimicrobial effect on wool and polyamide, when applied using the padding process, is slightly weaker than the effect on polyester.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Plant Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des compositions convenant très bien au traitement d'apprêt antimicrobien de matières plastiques, de préférence de PVC, et de textiles tissés et non tissés. Ces compositions se présentent sous la forme de solutions qui contiennent 0,1 à 8 % de 2,3,5,6-tétrachloro-4-(méthylsulfonyl)-pyridine. De façon idéale, ce principe actif est combiné avec d'autres principes actifs antimicrobiens. Dans ce contexte, l'utilisation de 2,4,4'-trichloro-2'-hydroxydiphényléther a donné des résultats excellents. Grâce à celà, le spectre d'efficacité antimicrobien est élargi et la concentration utilisée dans la solution est réduite. En plus de l'apprêt antimicrobien, on peut également obtenir un effet acaricide avec ladite formulation, si on ajoute à celle-ci des pyréthroïdes, de préférence du 3-phényoxybenzyl-(1 R;S)-cis-trans-2.2-diméthyl-3-(2,2-dichlorovinyl)-cyclopropancarboxylate. Ces formulations se caractérisent par un dosage et un traitement simples et hygiéniques, avec une faible concentration en principes actifs antimicrobiens.
PCT/CH1998/000341 1997-08-15 1998-08-14 Compositions pour le traitement d'apret antimicrobien de textiles et de matieres plastiques, et utilisation de ces compositions Ceased WO1999008527A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU86207/98A AU8620798A (en) 1997-08-15 1998-08-14 Compositions for treating textile and plastic antimicrobial finish, and use of same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH192097 1997-08-15
CH1920/97 1997-08-15
CH1919/97 1997-08-15
CH191997 1997-08-15

Publications (1)

Publication Number Publication Date
WO1999008527A1 true WO1999008527A1 (fr) 1999-02-25

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PCT/CH1998/000341 Ceased WO1999008527A1 (fr) 1997-08-15 1998-08-14 Compositions pour le traitement d'apret antimicrobien de textiles et de matieres plastiques, et utilisation de ces compositions

Country Status (2)

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AU (1) AU8620798A (fr)
WO (1) WO1999008527A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000720A1 (fr) * 1999-06-24 2001-01-04 Sanitized Ag Appret antimicrobien de mousses de polyurethanne utilisant du zinc-bis-(2-pyridinethiol-1-oxyde) conjointement avec d'autres principes actifs
FR2825131A1 (fr) * 2001-05-25 2002-11-29 Lg Electronics Inc Compositions pvc pour joint d'etancheite de porte d'appareil refrigerant
DE102006058790A1 (de) * 2006-12-12 2008-06-19 Sanitized Ag Verfahren zur antimikrobiellen Ausrüstung von Textilien und Faser
EP2202358A1 (fr) 2008-12-29 2010-06-30 Kompetenzzentrum Holz GmbH Papier imprégné avec des propriétés antimicrobiennes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4933011A (en) * 1983-12-12 1990-06-12 Morton Thiokol, Inc. Antimicrobial solution

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4933011A (en) * 1983-12-12 1990-06-12 Morton Thiokol, Inc. Antimicrobial solution

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Compositions containing 2,3,5,6-Tetrachloro-4(methylsulphonyl)pyridine", RESEARCH DISCLOSURE, no. 279, 1987, pages 436, XP002083827 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000720A1 (fr) * 1999-06-24 2001-01-04 Sanitized Ag Appret antimicrobien de mousses de polyurethanne utilisant du zinc-bis-(2-pyridinethiol-1-oxyde) conjointement avec d'autres principes actifs
FR2825131A1 (fr) * 2001-05-25 2002-11-29 Lg Electronics Inc Compositions pvc pour joint d'etancheite de porte d'appareil refrigerant
DE102006058790A1 (de) * 2006-12-12 2008-06-19 Sanitized Ag Verfahren zur antimikrobiellen Ausrüstung von Textilien und Faser
EP2202358A1 (fr) 2008-12-29 2010-06-30 Kompetenzzentrum Holz GmbH Papier imprégné avec des propriétés antimicrobiennes

Also Published As

Publication number Publication date
AU8620798A (en) 1999-03-08

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