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WO1999045975A1 - Matiere non tissee renfermant un acide thio-hydroxamique cyclique - Google Patents

Matiere non tissee renfermant un acide thio-hydroxamique cyclique Download PDF

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Publication number
WO1999045975A1
WO1999045975A1 PCT/GB1999/000660 GB9900660W WO9945975A1 WO 1999045975 A1 WO1999045975 A1 WO 1999045975A1 GB 9900660 W GB9900660 W GB 9900660W WO 9945975 A1 WO9945975 A1 WO 9945975A1
Authority
WO
WIPO (PCT)
Prior art keywords
thione
hydroxy
composition
methylthiazol
dimethyl
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/GB1999/000660
Other languages
English (en)
Inventor
John David Payne
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.)
Avecia Ltd
Original Assignee
Avecia Ltd
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 Avecia Ltd filed Critical Avecia Ltd
Priority to AU32657/99A priority Critical patent/AU3265799A/en
Priority to GB0018196A priority patent/GB2348891A/en
Publication of WO1999045975A1 publication Critical patent/WO1999045975A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/21—Acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents

Definitions

  • the present invention relates to a composition
  • a composition comprising a non-woven material and a cyclic thiohydroxamic acid or metal complex thereof and the use of such a composition in disposable articles such as nappies, incontinence pads and feminine hygiene packs.
  • EP 174, 128 discloses a disposable article such as a nappy, incontinence pad or feminine hygiene pack which is formed from a non-woven material treated with a mixture of linear polymeric biguanides having different molecular weights.
  • composition comprising a non-woven material and a cyclic thiohydroxamic acid of formula 1
  • each of R, R 1 and R 2 is, independently, alkyl which may be linear or branched, cycloalkyl, aryl or aralkyl.
  • the substituent may be any group which does not significantly adversely affect the microbiological properties of the CTA or salt or metal complex thereof.
  • suitable substituents are halogen such as fluorine, bromine and chlorine, hydroxy, and nitrile. It is preferred that R, R 1 and R 2 is unsubstituted.
  • R, R 1 and R 2 is alkyl, it is preferably isopropyl, n-butyl, isobutyl, tertiary butyl and especially methyl or ethyl.
  • R, R 1 and R 2 is aralkyl, it is especially 2-phenylethyl or benzyl.
  • the ring is preferably cyclohexyl.
  • the ring is preferably cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl and especially phenyl.
  • the CTA is preferably 2-hydroxy-2,3-dihydro-1 H-isoindol-l-thione , or derivatives thereof.
  • D is sulphur
  • CTA including metal complexes thereof, are:- 3-hydroxy-4methylthiazol-2(3H)-thione;
  • metal complexes of the CTA's are the 2:1 zinc complex of
  • the non-woven material is preferably fibrous and may be any material suitable for use as the absorbent layer in disposable items such as nappies, incontinence pads and feminine hygiene packs.
  • the fibres of the fibrous material have an average diameter from 1 to 200 ⁇ and especially from 10 to 100 ⁇ .
  • the fibres are at least 1 mm in length.
  • the fibres may be wet - or dry-laid and are preferably dry-laid to form a highly fluffed absorbent layer.
  • fibrous non-woven material examples include cellulose, modified cellulose and rayon.
  • Other suitable fibrous non-woven materials are hydrophobic fibres which are treated with a wetting agent.
  • hydrophobic fibres are polyolefine such as polyethylene and polypropylene, polyacrylamide, polyester such as polyethylene teraphthalate, polyamide, polystyrene and polyurethane.
  • the non-woven material is preferably cellulose and especially wood-pulp fibre which is optionally chemically modified by chemically cross-linking with a C 2 . 8 -dialdehyde to give an average water retention of from 28 to 50% by weight.
  • Preferred wood pulp fibres are those generally known as semi-chemical wood pulps and especially wood pulps such as those obtainable from sulphite or Kraft processes.
  • the CTA, or metal complex thereof may be the only microbiologically active compound present in the non-woven material or it may be present in conjunction with other microbiologically active compounds especially where it is desirable to broaden the spectrum of antimicrobal activity.
  • Such other compounds must be substantially non-toxic and non-irritating in skin contact when the composition is used as the absorbent layer in disposable items such as nappies, incontinence pads and feminine hygiene packs.
  • X and Y may be the same or different and represent bridging groups in which together the total number of carbon atoms directly interposed between the pairs of nitrogen atoms linked by X and Y is from 9 to 17.
  • the bridging groups X and Y may be polyethylene chains, optionally incorporating hetero atoms, such as oxygen, sulphur or nitrogen, for example, ethylene oxyethylene, or cyclic nuclei which may be saturated or unsaturated, in which case the number of carbon atoms directly interposed between the pairs of nitrogen atoms linked by X and Y includes the shortest segment(s) of the cyclic group, or groups.
  • the number of carbon atoms directly interposed between the nitrogen atoms in the group may be the same or different and represent bridging groups in which together the total number of carbon atoms directly interposed between the pairs of nitrogen atoms linked by X and Y is from 9 to 17.
  • the bridging groups X and Y may be polyethylene chains, optionally incorporating hetero atoms,
  • a preferred mixture of polymeric biguanides for use with the CTA, or salt or metal complex thereof is a mixture of poly (hexamethylene biguanides), in which X and Y both represent a -(CH 2 ) 6 - group.
  • Polymeric biguanides may be prepared by the reaction of a bisdicyandiamide having the formula
  • the biguanide polymer chains may be terminated either by an amino hydrochloride group or by an -NH-C(NH)-NH-CN group, and the terminating groups may be the same or different on each polymer chain.
  • Polymeric biguanides are generally obtained as mixtures in which the polymer chains are of different lengths and the number of individual biguanide units of formula 2 is from 1 to 40.
  • n is from 2 to 40.
  • the average molecular weight of the polymer mixture is preferably from about 1100 to about 3300.
  • the polymeric biguanides readily form water soluble salts with both inorganic and organic acids.
  • the acid is preferably inorganic and especially hydrohalic such as hydrochloric acid.
  • aqueous concentrates preferably have a pH value of below 8 and especially below 7.
  • Especially preferred aqueous solutions are those having a pH value below 4.5 as measured using an organic indicator.
  • the pH value of these aqueous concentrates is above 0.1 , more preferably above 0.5 and especially above 1.0 as determined using an organic indicator.
  • Concentrated aqueous solutions of this type are described in EP 485,079 and are commercially available as Vantocil IB and Cosmocil CQ (both Zeneca Limited).
  • composition comprising the CTA, including a salt or metal complex thereof, and non-woven material may further comprise an anionic polymer.
  • the anionic polymer is preferably substantially insoluble in urine so that it will not to any substantial extent dissolve and redistribute itself in the non-woven material during use.
  • the solubility of the anionic polymer in urine is preferably not greater that 2%, more preferably not greater that 1%, even more preferably not greater that 0.5% and especially not greater that 0.1% by weight under the conditions of use of the non woven material.
  • the anionic polymer is preferably obtainable by polymerising an anionic monomer or its anhydride or copolymerising an anionic monomer or its anhydride with non-ionic monomers.
  • Preferred anionic monomers or anhydrides are olefinically unsaturated acids and anhydrides which contain at least one olefinic double bond and especially monomers having a single olefinic double bond.
  • the anionic monomer may contain more that one anionic group but preferably contains only one anionic group.
  • the anionic group may be a phosphonic, phosphoric, sulphonic and especially a carboxylic acid group.
  • suitable anionic monomers are vinyl-phosphonic acid, styrenephosphonic acid, 2-acrylamidopropanephosphonic acid, ethylidene-1 ,1- diphosphonic acid, hydroxyethylacrylate monophosphate, styrene sulphonic acid, 2-acrylamido-2-methyipropane sulphonic acid, sulphoethyl methacrylate, vinylsulphonic acid, methallyl sulphonic acid, propene sulphonic acid and particularly methacrylic acid and especially acrylic acid.
  • Preferred non-ionic monomers are of Formula (4)
  • R 4 is hydrogen or C ⁇ -alkyl; and R 3 is optionally substituted C ⁇ o-alkyl.aryl or C 5 . 14 -cycloalkyl.
  • R 4 is alkyl it is preferably methyl.
  • R 3 When R 3 is alkyl it may be linear or branched and is preferably C ⁇ -alkyl. When R 3 is aryl it is preferably phenyl.
  • non-ionic monomers examples include methyl (meth)acrylate, butyl (meth)acryiate, ethyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate and acetoacetoxyethyl (meth)acrylate.
  • Preferred anionic polymers are polyacrylic acid and copolymers of acrylic acid with one or more non-ionic monomers, poly(maleic acid) and copolymers of maleic acid with one or more non-ionic monomers, alginic acid, graft polymers of acrylic acid onto starch and carboxymethyl cellulose.
  • Polyacrylic acid and its copolymers are optionally cross- linked and the MW range is generally from 1000 to 5,000,000.
  • These acrylic acid based polymers may be derivable from a water-soluble polyacrylic acid which is cross-linked with, for example, trimethylolpropanetriacrylate, poly(allylsucrose) or poly (allylpentaerythritol).
  • acrylic acid based polymers which act as fluid absorbing agents and are generally referred to as "super absorbents".
  • Super absorbents based on polyacrylates and related polymers are described in, for example, EP 311 ,344 and Chemistry in England, 1994, pp 652-656 (F.L. Buchholz) and the disclosures and references in these two documents are incorporated herein by reference.
  • Poly(maleic acid) and its polymaleate derivatives may also be optionally cross- linked and typically have a MW in the range 1 ,000 to 5,000,000. Examples of polymers of this type are poly(vinyl ether-maleic acid), poly(methylvinylether - maleic acid) and poly(styrene-maleic acid).
  • anionic polymers are those derivable from cellulose such as carboxymethylcellulose, partially oxidised cellulose, sulphoethyl cellulose and phosphorylated cellulose.
  • the anionic polymer may be present in the free-acid form or in the form of a salt with an amine or a metal.
  • suitable metals are lithium, potassium and particularly sodium. It is preferred, however, that at least some of the anionic groups of the anionic polymer are in the free-acid form. This is particularly the case where the anionic polymer is a super absorbent and it is preferred that at least 25 mole % and especially at least 50 mole % of the monomer units containing an anionic group which are used to make the anionic polymer are in the form of a salt. It is also preferred that at least 5 mole %, more preferably at least 10 mole % and especially at least 20 mole % of the monomers containing an anionic group which are used to make the anionic polymer are in the form of a free acid.
  • the anionic polymer may be in the form of sheets but is preferably present in the form of discrete particles or particle agglomerates. These particles can be of any shape such as spherical, semi-spherical, cubic, rod-like, needles or flakes and are preferably between 30 ⁇ and 2mm as the weighted average of the smallest dimension of the individual particles.
  • the amount of anionic polymer relative to the non-woven material treated with the CTA, or salt or metal complex thereof, is dependent on the end use of the composition. Thus, in the case of disposable articles such as nappies and incontinence pads, the amount of anionic polymer may be just sufficient to prevent any desorbed microbiologically active compound escaping from the disposable article during use. However, when the anionic polymer is also present as a super absorbent the amount of anionic polymer to non-woven material may be much higher. When the anionic polymer is a super absorbent the amount of anionic polymer is preferably at least 0.5%, more preferably at least 1 % and especially at least 5% by weight relative to the total weight of anionic polymer and non-woven material. It is also preferred that the amount of anionic polymer is less that 50%, more preferably less than 30%, and especially less than 20% by weight relative to the total weight of anionic polymer and non-woven material.
  • the anionic polymer and non-woven material are used as the absorbent layer in a disposable article such as a nappy or incontinence pad
  • a disposable article such as a nappy or incontinence pad
  • such layer can be formed by any method known to the art and especially by processes that produce a web of anionic polymer in admixture with non-woven fibres.
  • the web is dry-laid, especially by airlaying.
  • a process for forming an absorbent layer for use in a disposable article which comprises adding an anionic polymer to non-woven fibres containing the CTA, or a salt or metal complex thereof.
  • the CTA, or salt or metal complex thereof may be applied to the non-woven material as an aqueous dispersion by any method known to the art such as spraying, dipping or padding.
  • the pH of the aqueous dispersion is preferably from 5 to 8 and especially from 6 to 7.
  • the amount of CTA, or salt or metal complex thereof, in the composition is preferably at least 100, more preferably at least 500, and especially at least lOOOppm relative to the non-woven material. It is also preferred that the amount of CTA, or salt or metal complex thereof, is not greater than 10,000, more preferably not greater than 8,000 and especially not greater than 6,000 ppm relative to the non-woven material.
  • the composition may also contain other adjuvants for reducing or masking odours.
  • adjuvants are fragrances and organic acids.
  • Preferred organic acids are those containing two or more carboxylic acid groups and especially those possessing a buffering capacity. The organic acid must not possess such a low pKa value that it causes significant desorption of the microbiologically active compounds from the non-woven material. Consequently, preferred organic acids do not possess a pKa value below 1.
  • Particularly useful organic acids have a MW below 300 and especially below 200. Citric acid is especially preferred.
  • the composition of the present invention can be used as the absorbent layer in disposable articles for collecting body fluids such as nappies, incontinence pads and feminine hygiene packs. This absorbent layer is principally used for the collection and retention of body fluids such as urine and to reduce the generation of odours and incidence of skin rashes caused by the microbiological degradation of the body fluids.
  • a disposable article for collecting body fluids which contains a CTA, or salt or metal complex thereof.
  • micro-organisms were each, independently, cultured on agar for three generations.

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  • Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition renfermant une matière non tissée et un acide thio-hydroxamique cyclique de formule (1), ainsi que les sels et les complexes métalliques de cette composition, R représentant hydrogène, hydrocarbyle C1-6 éventuellement substitué, -COOR2, ou -OCOR2; A et B représentant indépendamment -C(R1)2, -CR1=, ou -N=; D représentant -C(R1)2-, -CR1=, ou soufre; R1 représentant hydrogène, hydrocarbyle C¿1-6? éventuellement substitué, ou deux groupes R?1¿, ces deux groupes formant avec l'atome ou les atomes de carbone auquels ils sont liés un cycle à 5 ou 6 chaînons, R2 représentant hydrocarbyle C¿1-6? éventuellement substitué. Le composé de formule (1) préféré est un complexe de zinc 2:1 de 3-hydroxy-4-méthylthiazol-2(3H)-thione.
PCT/GB1999/000660 1998-03-11 1999-03-05 Matiere non tissee renfermant un acide thio-hydroxamique cyclique Ceased WO1999045975A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU32657/99A AU3265799A (en) 1998-03-11 1999-03-05 Non-woven material comprising cyclic thiohydroxamic acid
GB0018196A GB2348891A (en) 1998-03-11 1999-03-05 Non-woven material comprising cyclic thiohydroxamic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9805172.5 1998-03-11
GBGB9805172.5A GB9805172D0 (en) 1998-03-11 1998-03-11 Composition and use

Publications (1)

Publication Number Publication Date
WO1999045975A1 true WO1999045975A1 (fr) 1999-09-16

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PCT/GB1999/000660 Ceased WO1999045975A1 (fr) 1998-03-11 1999-03-05 Matiere non tissee renfermant un acide thio-hydroxamique cyclique

Country Status (3)

Country Link
AU (1) AU3265799A (fr)
GB (2) GB9805172D0 (fr)
WO (1) WO1999045975A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10210195B4 (de) * 2002-03-07 2005-12-15 Schwarz Pharma Ag Verwendung von 1,3-Diazaspiro-[4,5]decan-2,4-dithion zur Behandlung von Schmerz

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174128A2 (fr) * 1984-08-31 1986-03-12 Imperial Chemical Industries Plc Matériau pour non-tissé traité
EP0498636A1 (fr) * 1991-02-05 1992-08-12 Zeneca Limited Composition cosmétique
WO1997005910A1 (fr) * 1995-08-03 1997-02-20 Zeneca Limited Composition de non-tisse a protection antimicrobienne et son utilisation
WO1997045146A1 (fr) * 1996-05-31 1997-12-04 Sca Hygiene Products Ab Matiere absorbante renforcee par des fibres textiles
WO1998026665A1 (fr) * 1996-12-18 1998-06-25 Zeneca Limited Composition et son utilisation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174128A2 (fr) * 1984-08-31 1986-03-12 Imperial Chemical Industries Plc Matériau pour non-tissé traité
US4655756A (en) * 1984-08-31 1987-04-07 Imperial Chemical Industries Plc Treated non-woven material
EP0498636A1 (fr) * 1991-02-05 1992-08-12 Zeneca Limited Composition cosmétique
WO1997005910A1 (fr) * 1995-08-03 1997-02-20 Zeneca Limited Composition de non-tisse a protection antimicrobienne et son utilisation
WO1997045146A1 (fr) * 1996-05-31 1997-12-04 Sca Hygiene Products Ab Matiere absorbante renforcee par des fibres textiles
WO1998026665A1 (fr) * 1996-12-18 1998-06-25 Zeneca Limited Composition et son utilisation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10210195B4 (de) * 2002-03-07 2005-12-15 Schwarz Pharma Ag Verwendung von 1,3-Diazaspiro-[4,5]decan-2,4-dithion zur Behandlung von Schmerz
US7282515B2 (en) 2002-03-07 2007-10-16 Schwarz Pharma Ag Derivatives of azaspiro compounds for the treatment of pain

Also Published As

Publication number Publication date
GB2348891A (en) 2000-10-18
AU3265799A (en) 1999-09-27
GB9805172D0 (en) 1998-05-06
GB0018196D0 (en) 2000-09-13

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