EP2021096A1 - Utilisation de tanins dans des filtres - Google Patents

Utilisation de tanins dans des filtres

Info

Publication number
EP2021096A1
EP2021096A1 EP07712373A EP07712373A EP2021096A1 EP 2021096 A1 EP2021096 A1 EP 2021096A1 EP 07712373 A EP07712373 A EP 07712373A EP 07712373 A EP07712373 A EP 07712373A EP 2021096 A1 EP2021096 A1 EP 2021096A1
Authority
EP
European Patent Office
Prior art keywords
filter
tanning agent
synthetic
condensation product
acid
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Withdrawn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
EP07712373A
Other languages
German (de)
English (en)
Inventor
Stephan Hüffer
Oliver Reese
Günter Scherr
Sebastien Garnier
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 SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP07712373A priority Critical patent/EP2021096A1/fr
Publication of EP2021096A1 publication Critical patent/EP2021096A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D39/00—Filtering material for liquid or gaseous fluids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets

Definitions

  • the present invention relates to the use of a tanning agent in or on filters, in particular natural or synthetic fiber fabrics or foams, for the prevention of infections, which filters are in particular part of respiratory masks or respiratory protective devices. Furthermore, the present invention also relates to the filters as those containing (at least) one tanning agent.
  • the use of filters in the form of textile protective clothing or protective masks to prevent infections has long been known.
  • the protective effect can serve both the wearer and the environment.
  • the protective effect is mainly based on a retention of germs (pathogens) in the tissue.
  • the problem here is that, for example, by the breath, the body sweat or the ambient air moisture is constantly supplied to the tissue, so that the germs in the tissue may remain active for a long time under certain circumstances. In sudden strong air movements, such as sneezing or deep breath, such agents can leave the tissue or the filter again.
  • EP-B 0 859 547 relates to protective equipment such as surgical masks or surgical drapes and other surgical clothing useful for inactivating viruses upon contact.
  • This is achieved by applying to the corresponding fabric substrate a coating of immobilized polymer molecules which provides the fabric substrate with non-leachable antiviral activity, the polymer molecules comprising a hydrophilic polymer having pendant antiviral groups comprising a plurality of pendant cationic groups and a plurality of hydrocarbon moieties.
  • Side chains include and the polymer molecules further comprise the residues of photochemically reactive side groups.
  • the hydrophilic polymer comprising the coating base of the textile substrate may be, for example, a copolymer of vinylpyrrolidone or acrylamide.
  • US-A-4,897,304 relates to protective clothing against viruses wherein the protective garment is based on cellulosic or non-woven fabric which in turn contains an anionic surfactant and an acid such as citric acid or benzoic acid.
  • US-A 5,690,949 relates to a microporous membrane which can prevent the passage of viruses.
  • the microporous membrane material comprises a thermoplastic polymer, another compound which is miscible with the thermoplastic polymer, for example, a liquid hydrocarbon such as mineral oil, and a water and oil repellent fluorine-containing compound that allows the barrier to viruses in the membrane.
  • tanning agents can be used to prevent or prevent infections in filters such as natural or synthetic fiber fabrics and microporous membrane materials, which are particularly part of respirators or respirators.
  • Gerbstoffe can in principle be divided into three main classes (see Rompps Chemie Lexikon, 9th edition (1995), Georg Thieme Verlag Stuttgart, keyword “Gerbstoffe", pages 1541 to 1542):
  • tanning agents such as chromium (III) salts or polyphosphates
  • Synthetic organic tanning agents which are mostly obtainable by sulfonation of solubilized aldehyde condensation products of aromatic bases, in particular of phenol, cresol, naphthalene and naphthol
  • tannins of vegetable origin such as those found in leaves (tea), seeds (coffee), berries, gall or wood.
  • tannins of vegetable origin are understood to mean the tannins or tannins, catechins or gallic acid derivatives.
  • both the tanning agents of vegetable origin (hereinafter referred to as vegetable or natural tanning agent) and the synthetic organic tanning agents (hereinafter referred to as synthetic tanning agent) are associated in the literature with the use as Arnzeistoff, in particular with antiviral activity. This applies in particular to vegetable or synthetic tanning agents, which are referred to as so-called polyphenols.
  • propolis which is collected from bees from the buds, barks and resins of certain trees and contains vegetable tannins, among others, an antiviral activity, for example, against herpes simplex attributed.
  • propolis which is a polyphenol
  • Propolis can also act as a protective coating impregnating wood, for example, by coating the outer walls of beehives with concentrated propolis-methylated spirits solution.
  • WO 95/14479 relates to a condensation polymer of aromatic sulfonic acids and an aldehyde for inhibiting the HIV virus. It is described that the higher the molecular weight of the polymer, the greater its therapeutic activity.
  • US Pat. No. 4,604,404 describes the use of sulfonated naphthalene-formaldehyde condensation polymers for controlling the herpes simplex virus.
  • DE-A 33 41 122 describes externally applicable virucidal drugs, especially against herpes labilis and viral diseases of the skin.
  • These medicines are synthetic tanning agents, produced by condensation of, for example, urea with phenol / cresol, formaldehyde and a sulfonating agent.
  • condensation products which are obtainable by reacting at least one aromatic compound, at least one sulfonating agent, at least one carbonyl compound and optionally at least one urea derivative. Following the synthesis, the condensation products are subjected to at least one molecular size-dependent separation process. The condensation product was separated into three fractions, a high molecular weight, a medium molecular weight and a low molecular weight fraction. It has been found that the high molecular weight fractions have improved activity in inhibiting the activity of human leukocyte elastase enzyme than the corresponding mid molecular weight fraction of this condensation product.
  • the uses of synthetic or vegetable tannins described above relate in particular to their use as (constituent of) a medicinal product.
  • the synthetic or vegetable tanning agents are in this context therefore administered to a mammal, in particular humans, for example for oral administration.
  • the state of the art does not describe anywhere that tanning agents in general, in particular synthetic or vegetable tanning agents, can also contribute to the prevention of infections outside of the human body (ie without direct administration as medicaments), for example as part of a respiratory mask, a respiratory protective device, a surgical mask or as part of a filter system for air treatment such as in air conditioning systems and locks.
  • the invention was thus based on the object to provide further filters, for example in the form of natural or synthetic fiber fabrics, in particular as part of a respiratory mask or a respiratory protective device.
  • this object is achieved by the use of one or more tanning agents in or on filters to prevent infections or by filters as such, containing at least one tanning agent.
  • tannins can be fixed stably on or in the corresponding filters, for example in or on fibrous webs. This is advantageous, in particular, in the case of their use as a component of respiratory masks and respiratory protection devices, since respiratory masks and respiratory protective devices or filter systems known from the prior art are often provided with volatile and / or mucous membrane-irritating substances. Tannins, on the other hand, are neither volatile (or at least only very slightly volatile), nor irritating to the mucous membranes, and in addition fixation on the corresponding filter is easily possible. For this reason, tannins are particularly effective in preventing or preventing infection as well as spreading the infections. The tannins eliminate (largely) the pathogens and thus prevent the penetration of the filters used even under unfavorable conditions. Furthermore, the tanning agents are active for a longer period of time in terms of the properties described above.
  • any tanning agent known to the person skilled in the art is suitable as a tanning agent.
  • a tanning agent provides Römpp's Chemielexikon, 9th edition (1995), Georg Thieme Verlag, Stuttgart, keyword “tanning", pages 1541 to 1542 an overview of the specialist known Gerbstoffe.
  • vegetable or synthetic tanning agents are used in the present invention.
  • Particularly preferred are synthetic tanning agents.
  • vegetable tanning agents are tannins such as catechins or gallic acid derivatives such as gallate.
  • Vegetable tanning agents based on gallic acid derivatives differ from the condensation products (A) according to the invention in particular, that the latter have in their chemical structures (a plurality of) -CR 1 R 2 bridges (crosslinks) derived from the carbonyl compound used a2) and are not present in vegetable tannins. If, for example, formaldehyde is used as component a2), the condensation products have (A) -CH 2 -bridges.
  • Vegetable tanning agents (gallates) are typically oligomeric systems, while the condensation products according to the present invention are preferably polymers.
  • Preferred vegetable tanning agents are tannins from the group of catechins, epicopes and epigallocatechins and their gallates.
  • Tannin is understood as meaning, in principle, naturally occurring polyphenols, as described, for example, in T. Okuda Phytochemistry, Volume 66 (2005), pages 2012 to 2031 or Römpp's Chemielexikon, 9th edition (1995), Georg Thieme Verlag, Stuttgart, keyword “tannins”, Pages 4452 to 4453 are listed.
  • Preferred tannins are ellagitannins and dehydroellagitannins, in particular geraniin, dehydrogeraniin, furosinin, ascorbican, geraniynic acid, mallotusic acid, pentagalloylglucose, camelliatannin A, casuariin, euphorbin E, camelliatannin F, agrimoniin, trapanin B, oenothein A, oednotine B or Gemin D, lignin and lignosulfonates. Also preferred are catechins, epicatechins and epigallocatechins.
  • a suitable catechin or derivatives thereof include in particular flavan-3-ols, flavan-3,4-diols (leucoanthocyanidins) and also flavanones, flavones, chalcones or dihydrocychalcones, epicatechins and epigallocatechins.
  • gallic acid derivatives examples include gallic acid, methyl tri-O-methyl gallate, tri-O-methyl gallic acid, methyl tri-O-acetyl gallate, methyl gallate, ethyl gallate, n-propyl gallate, isoamyl gallate, lauryl gallate, stearyl gallate, epigallocatechin gallate and gallic acid.
  • extracts of green tea can be used as vegetable tannins, as are extracts of chestnuts or mimosa.
  • synthetic tanning agent are in principle all tanning agents that can be prepared by synthetic routes.
  • synthetic tanning agent not vegetable tanning agents, such as the aforementioned tannins or catechins and Gallusklarivate be understood, even if they are also accessible by synthetic routes.
  • Preferred synthetic tanning agents are selected from the condensation products (A) to (C), which are defined below.
  • Condensation product (A) is obtainable by reaction of
  • Aromatic means compounds having at least one phenyl ring which may be substituted and which may also comprise a plurality of fused phenyl systems, for example naphthyl system, phenanthrene systems and anthracene systems. if appropriate, in the case of bicyclic or polycyclic systems, individual cycles may also be completely or partially saturated, provided that at least one cycle is aromatic.
  • Heteroaromatics in the present invention are aromatic systems which are preferably monocyclic or bicyclic, and optionally also polycyclic, and which contain at least one heteroatom, preferably selected from nitrogen, oxygen and sulfur.
  • heteroaromatic also includes, for example, bi or polycycles in which (in the case of the bicycle) both rings are aromatic as well as bicycles in which only one ring is aromatic.
  • heteroaromatics are: 3H-indoline, 2 (1H) -quinolinone, 4-oxo-i, 4-dihydroquinoline, 2H-1-oxoisoquinoline, 1, 2-dihydroquinoline, 3,4-dihydroquinoline, 1, 2-dihydroisoquinolinyl, 3,4-dihydroisoquinoline, oxindolyl, 1, 2,3,4-tetrahydroisoquinoline, 1, 2,3,4-tetrahydroquinoline, 5,6-dihydroquinoline, 5,6-dihydroisoquinoline, 5,6,7,8-tetrahydroquinoline or 5,6,7,8- tetrahydroisoquinoline.
  • At least one aromatic or heteroaromatic is selected from benzene, naphthalene, anthracene, aromatic alcohols, aromatic ethers and aromatic sulfones.
  • the aromatic or heteroaromatic (component a1) may be unsubstituted or at least monosubstituted. If one or more substituents are present, they are independently selected from C 1 -C 10 -alkyl groups such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n -Pentyl, iso-pentyl, sec-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso -hexyl, sec-hexyl, n-heptyl, n-octyl, 2-ethylhexyl , n-nonyl, n-decyl; particularly preferably C 1 -C 4 -alkyl, such as methyl, eth
  • C 2 -C alkenyl groups in particular vinyl, 1-allyl, 3-allyl, 2-allyl, cis- or trans-2-butenyl, ⁇ -butenyl,
  • aryl such as phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9 Phenanthryl, preferably phenyl, 1-naphthyl and 2-naphthyl, more preferably phenyl,
  • Naphthalene 1-methylnaphthalene, 2-methylnaphthalene, 1, 8-dimethylnaphthalene, 2,7-dimethylnaphthalene, phenanthrene, anthracene, 9-methylanthracene, 9-phenyl-anthracene.
  • aromatic alcohols which may be mentioned are: phenol, ortho-cresol, meta-
  • Cresol para-cresol, 2-ethylphenol, 3-ethylphenol, 4-ethylphenol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3, 5
  • aromatic ethers which may be mentioned are: diphenyl ether, di-ortho-tolyl ether, di-meta-tolyl ether and di-para-tolyl ether.
  • aromatic sulfones examples include diphenylsulfone and 4,4'-dihydroxydiphenylsulfone.
  • the component a1) is particularly preferably at least one compound selected from phenol, phenolsulfonic acid, 4,4'-dihydroxydiphenylsulfone and gallic acid.
  • mixtures of at least 2 aromatics are used as component a1), for example mixtures of naphthalene and phenol, naphthalene and cresol (mixture of isomers), naphthalene and diphenyl ether, naphthalene and ditolyl ether or phenol and ditolyl ether.
  • aldehydes and ketones selected from aldehydes and ketones, preferably with at least one aldehyde such as
  • formaldehyde it is preferred to use formaldehyde in aqueous solution.
  • Suitable sulfonating agents are, for example, sulfuric acid, in particular concentrated sulfuric acid, furthermore oleum having an SO 3 content of from 1 to 30% by weight, furthermore chlorosulfonic acid and sulfamic acid. Preference is given to concentrated sulfuric acid and oleum containing from 1 to 15% by weight of SO 3 .
  • urea and all derivatives thereof are suitable as component a4). Preference is given to a urea derivative which carries at least one hydrogen atom on each nitrogen atom.
  • At least one urea derivative is particularly preferably selected from compounds of the general formula (I) O
  • X 1 , X 2 are different or preferably the same and are selected from hydrogen and
  • R 1 , R 2 are different or preferably identical and selected from hydrogen, C 1 -C 10 -alkyl, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert.
  • n-pentyl iso-pentyl, sec-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-
  • decyl particularly preferably C 1 -C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, or
  • R 1 and R 2 together form a C 2 -Cio-alkylene unit, unsubstituted or substituted with 2 to 5 hydroxyl groups, such as - (CH 2 ) 2 -, -CH 2 -CH (CH 3 ) -, - (CH 2 ) 3 -, -CH 2 -CH (C 2 H 5 ) -, - (CH 2 J 4 -, - (CH 2 ) 5 -, - (CH 2 ) 6 -, - (CH 2 ) 7 -, - ( CH 2 ) 8 -, - (CH 2 ) 9 -, - (CH-OH) 2 -,
  • one or more further reactants a5) can also be added during the reaction, for example NaHSO 3 , Na 2 S 2 O 5 , KHSO 3 , K 2 S 2 O 5 , aqueous alkali metal hydroxide. solution, in particular aqueous sodium hydroxide solution and aqueous potassium hydroxide solution, and aqueous ammonia.
  • the reactant a5) is used in particular for adjusting the pH and for controlling the solubility of the end product
  • a molecular size-dependent separation process in the preparation of the condensation product (A) after reaction of the components a1) and a2) and optionally a3) and a4), can be carried out, preferably an ultrafiltration, giving individual fractions of the condensation product (A ), for example, a low molecular weight, a medium molecular weight and a high molecular weight fraction.
  • the low molecular weight fraction preferably has an M w value of 300 to 3000 g / mol.
  • Suitable molecular size-dependent separation processes are, for example, preparative gel permeation chromatography and membrane separation processes such as microfiltration, nanofiltration and, in particular, ultrafiltration. Combinations of microfiltration and ultrafiltration are also suitable.
  • Microfiltration and ultrafiltration and membranes required for this purpose are known as such and described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 6th Edition, Vol. 21, Wiley-VCH Weinheim, pages 243-321.
  • Nanofiltration and the associated membranes are known as those likewise known and described in R. Rautenbach, "Membrane Process", Springer Verlag Berlin Heidelberg 1997.
  • the exact execution of the separation of the condensation product (A) into individual fractions as a function of the molecular weight is known to the person skilled in the art and, for example, in DE-A 10 2004 034 613.
  • Condensation product (B) is obtainable by reaction of
  • b1) at least one cyclic organic carbonate with b2) at least one compound having at least two nucleophilic groups per molecule, selected from sulfonic acid, hydroxyl, primary or secondary amino or mercapto groups.
  • the condensation product (B) preferably has an M w value of between 300 and 3000 g / mol.
  • Condensation products (B) as such and processes for their preparation are known in the art, they are for example in the German application with the Number DE 10 2005 050 193.1 is disclosed and incorporated by reference in the present invention.
  • cyclic organic carbonates (component b1) are understood as meaning organic carbonic acid esters which have at least one cyclic group.
  • Cyclic organic carbonates are preferably those organic carbonic acid esters in which the carbonic ester group is part of a cyclic system.
  • cyclic organic carbonate (b1)) is selected from compounds of the general formula (II)
  • R 1 selected from C 1 -C 4 -alkyl, branched or preferably linear, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, very preferably methyl and Ethyl, and most preferably hydrogen,
  • R 2 is optionally different or preferably identical and independently selected from hydrogen and C 1 -C 4 -alkyl, branched or preferably linear, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl
  • a is an integer in the range of 1 to 3, preferably 2 and more preferably 1.
  • Component b2) is understood as meaning compounds which have two groups which are capable of nucleophilic reactions, for example sulfonic acid groups, hydroxyl groups, mercapto groups or primary or secondary amino groups.
  • suitable compounds b2) may comprise: at least two nucleophilic hydroxyl groups per molecule, at least two nucleophilic mercapto groups per molecule, at least two nucleophilic primary or secondary amino groups per molecule, for example two or three nucleophilic primary or secondary amino groups per molecule, at least one nucleophilic hydroxyl group or Mercapto group and at least one nucleophilic primary or secondary amino group per molecule or at least one nucleophilic hydroxyl group and at least one nucleophilic mercapto group per molecule,
  • At least one nucleophilic hydroxyl group or primary or secondary amino group and one sulfonic acid group per molecule at least one nucleophilic hydroxyl group or primary or secondary amino group and one sulfonic acid group per molecule.
  • Sulfuric acid is not a compound b2) in the context of the present invention.
  • nucleophilic hydroxyl groups are OH groups of primary and secondary alcohols and in particular phenolic OH groups.
  • nucleophilic mercapto groups are SH groups, aliphatic or aromatic.
  • nucleophilic amino groups are -NHR 3 groups, aliphatic or aromatic, wherein R 3 is selected from hydrogen, C 1 -C 4 -alkyl, as defined above, and CN, or the NH 2 -group of, for example, amidosulfonic acid.
  • OH groups and NH groups which are constituents of aminal groups, semiaminal groups or hydrate groups of ketones or aldehydes are not nucleophilic hydroxyl groups or amino groups in the context of the present invention.
  • OH groups and NH groups which are constituents of carboxylic acid groups or carboxamide groups are also not nucleophilic hydroxyl groups or amino groups in the sense of the present invention.
  • Alkyl, biuret, in particular unsubstituted urea ii) heterocyclic compounds having at least two NH 2 groups per molecule, for example adenine and in particular melamine, iii) benzoguanamine, dicyandiamide, guanidine, iv) compounds of the general formula (III)
  • A is a divalent group, for example -CH 2 -, -CH 2 CH 2 -, -CH (CH 3 ) -, -C (CH 3 ) 2 -, -CO-, -SO 2 -, preferably 4, 4'-dihydroxybiphenyl, 2,4'-dihydroxydiphenylsulfone, more preferably 4,4'-dihydroxydiphenylsulfone, mixtures of 4,4'-dihydroxydiphenylsulfone and 2,4'-dihydroxydiphenylsulfone, for example in a weight ratio of 8: 1 to 8: 1, 5, and bisphenol A.
  • compound b2) are 4-hydroxyphenylsulfonic acid and amidosulfonic acid.
  • Particularly preferred compounds b2) are selected from melamine, biuret, dicyandiamide, amidosulfonic acid, and 4,4 " dihydroxydiphenyl sulfone.
  • Condensation product (C) is obtainable by reaction of
  • melamine and / or urea c2) glyoxal, glyoxylic acid and / or an alkali salt thereof, c3) optionally at least one aromatic compound having at least one phenolic hydroxyl group and c4) optionally at least one condensable compound having a reactive nitrogen-containing group.
  • the condensation product (C) preferably has an M w value of between 300 and 3000 g / mol.
  • condensation products (C) as such and processes for their preparation are known in the art. For example, these are described in EP-A 0 301 406 and are incorporated by reference in the present invention.
  • Suitable components c3) are, for example, phenolsulfonic acid, sulfosalicylic acid, salicylic acid and 8-hydroxyquinoline.
  • Suitable as component c4) are carboxylic acid amides, sulfonic acid amides, imides, ureas, amino and imino acids and dialkylamines and dialkanolamines. Examples are acetamide, benzoic acid amide, formamide, Amidosulphonic acid, succinimide, glycine, iminodiacetic acid, phenylglycine, urea, dicyandiamide, diethanolamine or diethylamine. Acidic compounds can be condensed in the form of their alkali metal salts. Particularly preferred as component c4) acetamide and amidosulfonic acid.
  • a preferred condensation product (C) is obtainable by reacting
  • a tanning agent which contains at least one hydroxyl group or is substituted by such a group.
  • condensation products (A), (B) or (C) this is preferably achieved by
  • component a1) contains at least one compound which is substituted by at least one hydroxyl group and / or component b2) contains at least one compound which is substituted by at least one hydroxyl group and / or component c3) is present.
  • the term filter will in principle be understood to mean any type of materials (substrates or filter base) which exert a filter effect.
  • the filter comprises a natural or synthetic fibrous web, a foam, a film, a textile, polymeric fibers and / or a matrix having voids within the matrix.
  • the filter may comprise one or more of these preferred components, if appropriate, the filter may also be formed completely from one or more of these components.
  • the term "fiber fabric” is intended to include such fiber fabrics that are not textiles, as well as the term “textile” should also include those textiles that are not fiber fabrics.
  • Films are preferably porous, polymer fibers are preferably water-insoluble. Fiber tissues can be natural or vegetable.
  • Particularly preferred filters are foams or natural or synthesized fibrous webs. As a filter, especially as natural or synthetic fiber tissue but not hides, especially derived from animals hides and wood or wood products should be understood.
  • the natural or synthetic fiber fabric is preferably woven or non-woven fiber fabric, in particular cellulose,
  • Fibers Cellulose derivatives, cotton, fleece, wool, silk, polyamides (nylon), polypropylene, Polyester, other plastics (eg viscose, acetate (partially synthetic), polyacrylates, polyvinyl chloride (PVC) and blends of polymers) and glass fibers.
  • the fibers may also be interconnected via a polymer matrix.
  • Foam should preferably be understood as meaning polyurethane-amino resin condensates which preferably form a microporous and / or open-pore system. Particularly preferred are melamine-formaldehyde condensates. Foams as such are known to the person skilled in the art.
  • Suitable fiber-based filter materials are commercially available, e.g. from Freudenberg Faserfliesstoffe KG (Weinheim, Germany), Sontara Technologies (subsidiary of DuPont Corporation, Old Hickory, Tenn., USA), Lystil S.A. (Brignoud Cedex, France), Dexter Nonwovens (Windsor Locks, Conn., USA).
  • Suitable foam-based filter materials can be obtained, for example, under the trademark Basotect® from BASF AG (Ludwigshafen, Germany).
  • Another object of the present invention is thus a filter as such, containing at least one tanning agent (according to the above definitions with respect tannins).
  • the filter is part of a respirator or a respirator or a filter system, for example, from an air conditioner.
  • the filter may also fully form the respirator or respirator.
  • the filter (article) in a multi-ply design, among others. equipped with foamed, open-pore polymer inserts.
  • foamed polymers polyurethanes, melamine-formaldehyde condensates such as Basotect® from BASF AG
  • the filters according to the invention can also be part of surgical articles, in particular surgical drapes or surgical masks, or the filters according to the invention can form these objects completely.
  • a method for producing a filter for example a fiber fabric, and methods for producing respiratory masks, respiratory protective devices or surgical articles or the introduction of the corresponding filters in respiratory masks, respiratory protective devices or surgical articles are known in the art.
  • tanning agents can be applied to objects, such as leather.
  • the tanning agent (s) may, according to the present invention, be applied or incorporated, in particular incorporated, in or on the filter, in particular the fiber fabric. If the tanning agent is applied to the fiber fabric, it is preferably in the form of a coating.
  • the filter or the fiber fabric is drummed or sprayed with an aqueous solution of one or more tanning agents or treated by roll coating.
  • the coating may be applied to the article or to the article itself prior to processing a textile.
  • the fibers are adequately impregnated / coated during or immediately after fiber production (for example in the case of viscose, nylon or polypropylene (PP) fibers).
  • the tanning agent (s) may also be incorporated into the fibrous web and the fibrous web is covered with another fibrous web which may be the same or different.
  • tanning agents in or on filters, especially natural or synthetic fiber fabrics or foams, results in avoidance of infection. This applies in particular if the corresponding filter is part of a respiratory mask or respiratory protective device or completely forms it.
  • the tanning agents By using the tanning agents, a depletion and / or elimination of germs such as viruses or bacteria from the air, in particular from the breath, can be achieved.
  • Each 100 .mu.l sample solution mix it with reagent solution and sets a mean residence time of 1, 5 minutes, which corresponds to a flow of 35 ml / min.
  • the flow-injection apparatus is calibrated with formaldehyde solutions of known content. 1. Preparation of reaction solutions
  • Reactants a) phenol, b) concentrated sulfuric acid, c) formaldehyde, d) urea
  • Phenol by HPLC (based on nonvolatiles): 0.36 wt%;
  • M n 890 g / mol
  • M w 7820 g / mol, determined by GPC.
  • Reactants a) Dioxide diphenyl sulphone b) sodium sulfite c) formaldehyde d) sodium hydrogen sulfate
  • Reactants a) phenol, b) concentrated sulfuric acid, c) formaldehyde, d) urea
  • reaction solution 1.3 After stirring for 15 minutes, 800 g of aqueous sodium hydroxide solution (50% by weight) are added, taking care that the temperature does not exceed 85 ° C., so that the pH is then between 7.3 and 7.5. 11.3 kg of reaction solution 1.3 are obtained with 47% by weight of non-volatile constituents. The analysis of the reaction solution 1.3 gives the following values:
  • the fabrics are treated with an aqueous solution of the tanning agent or tanning agents, so that after drying a sufficiently large, uniformly distributed amount of tanning agent remains in the tissue.
  • the tissues are 60 min. drummed at 50 ° C in a 40% tannin solution. They are then at 60 ° C for 90 min. dried long in a dry air stream.
  • the following fabrics / tiles are used in the examples: a) cotton fleece from Freudenberg (Weinheim, Germany), b) Freudenberg's polycellulose fleece, c) polypropylene fleece from Freudenberg.
  • a microporous foam (Basotect from BASF AG, cut into 100 mm ⁇ 100 mm ⁇ 7 mm slices) is mixed with 25 ml of the tannin solutions. Soaked table and left at 50 ° C for 30 minutes. The excess solution is removed by squeezing between tissue sheets (15 g of the original solution). The moist foams are dried at 60 ° C for 90 minutes in a stream of air. The weight gain is typically 2.5 - 4 g.
  • Examples 1-6 describe typical formulations for the treatment of the filter substrates, wherein the treatment can be carried out both by spraying and by impregnation. Fixing takes place by drying at 60 ° C in a drying cabinet or in a stream of dry air.
  • the compounds 1.1 and 1.2 are listed above as an example of a condensation product (A). example 1
  • Chestnut extract (powder, Silvachimica srl, Italy, S. Michele Mondovi)
  • Example 6 different tanning agent formulations (Examples 1-6) including chestnut extract and epigallocatechin gallate (green tea extract) are applied to 3 different carrier substrates (non-woven cellulose, Freudenberg, PP-Flies (Freudenberg) and Basotect-Schaum (BASF AG)
  • carrier substrates non-woven cellulose, Freudenberg, PP-Flies (Freudenberg) and Basotect-Schaum (BASF AG
  • the test for the inhibition of viral activity is carried out as far as possible in accordance with test procedures EN 14675.
  • Avian influenza A virus (A / carduelis, H7N 1).
  • the filter substrates as described above are flowed through at 15 ° C at 35 ° C with water vapor-saturated air (35 ° C).
  • the virus suspension is then sprayed onto the filters and passed through with humid air (35 ° C) for a further 30 minutes.
  • the filters are cut into small pieces a 10 X 10 mm and taken up in a container with 50 ml of deionized water.
  • the zero value (negative control) is determined in each case on the basis of the non-impregnated carrier.
  • the impregnated filters consistently deliver significantly lower virus titers.
  • Table 1 Virus activity against avian influenza A virus on different filter substrates with and without (negative control) or different impregnation

Landscapes

  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne l'utilisation d'un tanin dans un filtre ou sur celui-ci, constitué en particulier de tissus de fibres ou des mousses synthétiques ou naturels, lesdits filtres étant utilisés en particulier comme composants de masques respiratoires ou d'équipement respiratoire.
EP07712373A 2006-05-17 2007-02-28 Utilisation de tanins dans des filtres Withdrawn EP2021096A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07712373A EP2021096A1 (fr) 2006-05-17 2007-02-28 Utilisation de tanins dans des filtres

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06114063 2006-05-17
EP07712373A EP2021096A1 (fr) 2006-05-17 2007-02-28 Utilisation de tanins dans des filtres
PCT/EP2007/051885 WO2007131812A1 (fr) 2006-05-17 2007-02-28 Utilisation de tanins dans des filtres

Publications (1)

Publication Number Publication Date
EP2021096A1 true EP2021096A1 (fr) 2009-02-11

Family

ID=38080925

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07712373A Withdrawn EP2021096A1 (fr) 2006-05-17 2007-02-28 Utilisation de tanins dans des filtres

Country Status (4)

Country Link
US (1) US20090269378A1 (fr)
EP (1) EP2021096A1 (fr)
CN (1) CN101489641B (fr)
WO (1) WO2007131812A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090311329A1 (en) * 2006-04-20 2009-12-17 Technion Research And Development Foundation Ltd Casein micelles for nanoencapsulation of hydrophobic compounds
US8426632B2 (en) * 2007-08-31 2013-04-23 The Nippon Synthetic Chemical Industry Co., Ltd. Crosslinking agent, crosslinked polymer, and uses thereof
US20110126501A1 (en) * 2009-10-16 2011-06-02 Woongjin Coway Co., Ltd. Composition for prevention of influenza viral infection comprising tannic acid, air filter comprising the same and air cleaning device comprising the filter
WO2016118411A1 (fr) 2015-01-21 2016-07-28 Resinate Materials Group, Inc. Polyols à niveau de recyclage élevé composés de polyesters thermoplastiques et de lignine ou de tannine
US9708675B1 (en) * 2015-07-15 2017-07-18 Jury Artola Method of tanning and washing leather, canvas, cotton and any other materials, as well as the finished product
WO2019100058A1 (fr) 2017-11-20 2019-05-23 Resinate Materials Group, Inc. Compositions de polyol à partir de polyesters thermoplastiques et leur utilisation dans des adhésifs thermofusibles et des liants
CN110368745A (zh) * 2019-06-28 2019-10-25 江苏美滤新材料有限公司 一种抗菌型空气过滤用微孔膜复合滤网及其制备方法
US20230145442A1 (en) * 2020-04-01 2023-05-11 Basf Se Condensation product for use in a method for the treatment of covid-19
WO2023051925A1 (fr) * 2021-09-30 2023-04-06 Basf Se Polymères obtenus par la réaction d'un composé phénolique et d'un composé carbonyle pour une utilisation dans le traitement ou la prévention d'un état associé à une ou plusieurs protéases
WO2023051923A1 (fr) * 2021-09-30 2023-04-06 Basf Se Polymères obtenus par la réaction d'un composé phénolique et d'un composé carbonyle en tant qu'agents anti-sras-cov-2

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3625811A (en) * 1968-01-19 1971-12-07 Sato Hisao Method of preparing yarn and the like from animal hide
US4604404A (en) * 1985-04-03 1986-08-05 A. H. Robins Company, Inc. Antiviral sulfonated naphthalene formaldehyde condensation polymers
US5264000A (en) * 1988-06-06 1993-11-23 Ciba-Geigy Corporation Aqueous solutions of synthetic tanning agents
JP4129569B2 (ja) * 2001-02-15 2008-08-06 株式会社大貴 不織布及び該不織布の製造方法
CA2521972A1 (fr) * 2003-04-11 2004-10-28 Hououdou Co., Ltd. Compositions pour la protection de la peau
DE602005011437D1 (de) * 2004-06-18 2009-01-15 Symrise Gmbh & Co Kg Brombeerextrakt
DE102004034613A1 (de) * 2004-07-16 2006-02-09 Basf Ag Durch molekülgrößenabhängige Trennverfahren behandelte Kondensationsprodukte als Arzneimittel und ihre Verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007131812A1 *

Also Published As

Publication number Publication date
CN101489641A (zh) 2009-07-22
US20090269378A1 (en) 2009-10-29
WO2007131812A1 (fr) 2007-11-22
CN101489641B (zh) 2013-06-12

Similar Documents

Publication Publication Date Title
WO2007131812A1 (fr) Utilisation de tanins dans des filtres
EP0520182B1 (fr) Produits de condensation de phénols sulfonés, d'urée, d'autres bases organiques azotées et de formaldéhyde et leur utilisation comme agent de tannage et comme agent de pulvérisation de poudres de polymère redispersables
DE1941932A1 (de) Permeabilitaetsselektive Kunststoffmembran und Verfahren zur Herstellung derselben
WO2007131811A1 (fr) Melanges de tanins, leur production et leur utilisation dans des médicaments ou leur utilisation en tant que désinfectants
EP0816406B1 (fr) Procedure pour la préparation de produits de condensation pauvres en sel
DE112009000188T5 (de) Polyimid-Gastrennungs-Membran und Gastrennungs-Verfahren
DE2642245B2 (de) Polyvinylalkohol-Hohlfaser und ihre Verwendung
EP2021010B1 (fr) Produits de condensation, procédé de production associé et leur utilisation dans des médicaments, en tant que désinfectants
EP4125832A1 (fr) Produit de condensation destiné à être utilisé dans un procédé de traitement de la covid-19
JP2003079756A (ja) マスク及びマスク用アレルゲン低減化シート
DE1916722C3 (de) Polymerlösung und deren Verwendung zur Herstellung von Fäden und Filmen
EP2812479A2 (fr) Rideau de douche à protection anti-salissures et son procédé de fabrication
EP2686381B1 (fr) Film composite et fibres kératiniques et cellulosiques
EP3500697B1 (fr) Procédé de production de fibre acrylique ou modacrylique ayant un effet anti-odeur
DE102013223126A1 (de) Verfahren zur Herstellung von lösemittelstabilen Polymermembranen, Polymermembran sowie Lösung zur Herstellung einer Polymermembran
EP3345480A1 (fr) Utilisation d'un extrait de chataigne comme agent acaricide
DE102004034613A1 (de) Durch molekülgrößenabhängige Trennverfahren behandelte Kondensationsprodukte als Arzneimittel und ihre Verwendung
JPS58136822A (ja) 抗菌性アクリル系合成繊維及びその製造法
WO2010043680A1 (fr) Procédé de production de cuir
Mersha et al. 2B2_0721_ FUNCTIONALIZATION OF ELECTROSPUN NANOWEB USING ETHIOPIAN ENDEMIC PLANT
CN118756426A (zh) 一种茶纤维复合面膜布及其制备方法
DE1931153C3 (de) Lösung einer Poly-alpha-aminosäure zur Herstellung von Filmen und Fasern
DE1669341B1 (de) Pulverfoermige Gerbstoffe
Suwannamek et al. Effect of Chitosan Compounds on Composite Fibers Properties
DE2125908A1 (fr)

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

17P Request for examination filed

Effective date: 20081217

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA HR MK RS

DAX Request for extension of the european patent (deleted)
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: 20140321