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WO2009009815A1 - Charge siliceuse - Google Patents

Charge siliceuse Download PDF

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Publication number
WO2009009815A1
WO2009009815A1 PCT/AT2008/000259 AT2008000259W WO2009009815A1 WO 2009009815 A1 WO2009009815 A1 WO 2009009815A1 AT 2008000259 W AT2008000259 W AT 2008000259W WO 2009009815 A1 WO2009009815 A1 WO 2009009815A1
Authority
WO
WIPO (PCT)
Prior art keywords
silica filler
guanidine derivative
filler according
polymeric guanidine
biofilm
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/AT2008/000259
Other languages
German (de)
English (en)
Inventor
Oskar Schmidt
Christoph Schmidt
Roland Zinnenburg
Christa Hametner
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.)
AKA Tech GmbH
Original Assignee
AKA Tech GmbH
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 AKA Tech GmbH filed Critical AKA Tech GmbH
Priority to EP08772587A priority Critical patent/EP2197959A1/fr
Publication of WO2009009815A1 publication Critical patent/WO2009009815A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3072—Treatment with macro-molecular organic compounds
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/08—Ingredients agglomerated by treatment with a binding agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon

Definitions

  • the present invention relates to a siliceous filler and a biofilm-inhibiting polymer containing this filler.
  • biofilm consisting of living and dead microorganisms.
  • biofilm may e.g. cause the material to be destroyed by the deposition of enzymes.
  • biofilms There is also a risk of contamination with other objects.
  • the economic damage biofilms can cause is enormous.
  • siliceous filler which is modified with a polymeric guanidine derivative based on an alkylenediamine and / or an oxyalkylenediamine.
  • polymeric guanidine derivatives have microbicidal properties and are known, for example, from WO 01/85676 A1, AT 406,163 B and WO 06/047800.
  • the invention is based on the surprising observation that these guanidine derivatives bind so strongly to silicates that they are practically no longer water-soluble and therefore immobile in the polymer matrix, but still have the microbiocidal activity.
  • Silastic fillers for polymers are known per se. Now, when these fillers are modified with the polymeric guanidine derivative and incorporated into the polymer, they impart to the polymer the biofilm-inhibiting property which persists even when the polymer is superficially damaged.
  • a preferred embodiment of the siliceous filler according to the invention is characterized in that a polymeric guanidine derivative is provided which contains the alkylenediamine and the oxyalkylenediamine in a molar ratio of between 4: 1 and 1: 4.
  • amino groups of the alkylenediamine and / or the oxyalkylenediamine are preferably terminal, wherein for the preparation of the polymeric guanidine derivative as the alkylenediamine in the first place, a compound of the general formula
  • n is an integer between 2 and 10, in particular 6, is.
  • polymeric guanidine derivative for the preparation of the polymeric guanidine derivative can as oxyalkylene diamine a compound of the general formula
  • n is an integer between 2 and 5, in particular 2.
  • a silicate filler which is characterized in that the polymeric guanidine derivative is a polyoxyalkylene guanidine based on triethylene glycol diamine (relative molecular mass: 148), of polyoxypropylenediamine (relative molecular mass: 230) and / or of polyoxyethylenediamine (relative molecular mass: 600) is provided.
  • the polymeric guanidine derivative is a polyoxyalkylene guanidine based on triethylene glycol diamine (relative molecular mass: 148), of polyoxypropylenediamine (relative molecular mass: 230) and / or of polyoxyethylenediamine (relative molecular mass: 600) is provided.
  • silicate filler in which is provided as the polymeric guanidine derivative poly [2- (2-ethoxyethoxyethyl) guanidinium hydrochloride] having at least 3 guanidine residues.
  • the polymeric guanidine derivative has an average molecular weight in the range of 500 to 3,000.
  • the invention further relates to a biofilm-inhibiting polymer which comprises the contains silicate filler according to the invention.
  • the filler may be contained in an amount between 0.05 and 5.0 wt .-%.
  • the polymer may be a thermoplastic or a hardenable plastic.
  • the term "polymer” also refers to elastomers and rubber (synthetic and natural rubber).
  • silicate filler is not only powdery SiO 2 , but also finely divided silicas and other silicates, especially those that are used today as fillers in plastics technology.
  • the binding of the polymeric guanidine derivative (active ingredient) to the siliceous filler, ie the carrier matrix, is carried out by presentation of the matrix, which may for example consist of fine Aerosil types, and mixing a 1-30% aqueous solution of the active ingredient at room temperature in a stirred tank.
  • the water can then be removed using conventional technologies, such as fluid bed dryers.
  • the matrix-bound active substance in this form is still very effective against microorganisms, but is so strongly bound to the active ingredient that it is virtually insoluble in water and can be washed out.
  • the described matrix fixation of the active ingredient thus prevents the migration of the active ingredient in aqueous media. Migration into fatty media is also not possible due to the insolubility of the polar agent.
  • the siliceous filler according to the invention can be used, for example, in HDPE in application concentrations of 0.5 and 1% by weight, based on HDPE, in the extrusion process, with a reduction at the sample surface of the pathogenic microorganism Staphylococcus aureus (ATCC 6538) even at 0.5%. by 7.8 * 10 4 to 67 germs, ie more than 3 orders of magnitude has been achieved.
  • the siliceous filler according to the invention in weight ratios of 2% to 30% with polyurethane (Pellethane 2363-90 A natural) was processed and then the effectiveness of the test bacteria Escherichia coli (DSM 787) and Staphylococcus aureus (DSM 346) using of the method JIS Z 2801: 2000 ("Antimicrobial products test for antimicrobial activity and efficacy") was tested on the plastic surface by incubating the samples with a microbial suspension and incubating at a relative humidity of> 90% and a temperature of 35 ° C After 24 hours, the test pieces were extracted with physiological saline at a rotary shaker at 250 rpm for 15 minutes, and the germ counts were determined.
  • the filler according to the invention can also be incorporated without difficulty into flexible PVC (PVC-p).
  • PVC-p flexible PVC
  • the lasting biocidal effectiveness of the filler according to the invention without significant drug migration is further demonstrated in acrylate mixtures.
  • the filler was incorporated in concentrations between 0.25 and 0.75% in the acrylate matrix.
  • the biocidal efficacy was tested with the test bacteria Streptococcus mutans DSM 20523 and Candida albicans DSM 1386 using the method JIS Z 2801: 2000 on the plastic surface, the samples up to 26 weeks at 37 ° C in ultrapure water with constant shaking in a ratio of 1: 1 (cm: cm) were eluted.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une charge silicieuse, modifiée avec un dérivé de guanidine polymère à base d'alkylènediamine et/ou d'oxyalkylènediamine. La charge s'utilise comme additif antibiofilm dans des polymères, notamment des matières plastiques.
PCT/AT2008/000259 2007-07-16 2008-07-16 Charge siliceuse Ceased WO2009009815A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08772587A EP2197959A1 (fr) 2007-07-16 2008-07-16 Charge siliceuse

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AT11162007A AT505514B1 (de) 2007-07-16 2007-07-16 Silikatischer füllstoff
ATA1116/2007 2007-07-16

Publications (1)

Publication Number Publication Date
WO2009009815A1 true WO2009009815A1 (fr) 2009-01-22

Family

ID=39837491

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AT2008/000259 Ceased WO2009009815A1 (fr) 2007-07-16 2008-07-16 Charge siliceuse

Country Status (3)

Country Link
EP (1) EP2197959A1 (fr)
AT (1) AT505514B1 (fr)
WO (1) WO2009009815A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013064161A1 (fr) 2011-11-02 2013-05-10 Mindinvest Holdings Ltd. Silicate de polyguanidine et son utilisation
EP3524055A1 (fr) 2018-02-08 2019-08-14 BCSK Biocid GmbH Agent lubrifiant antibactérien et spermicide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009052725A1 (de) * 2009-11-12 2011-05-19 B. Braun Melsungen Ag Verwendung von Polyoxyalkylendiamin-basierten Polyguanidinderivaten für medizinische Artikel

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2408192A1 (de) * 1973-02-20 1974-09-05 Dow Corning Verbundstoff mit antimikrobieller wirkung
AT408302B (de) * 2000-05-11 2001-10-25 P O C Oil Industry Technology Biozide polymere der reihe der polyoxyalkylen-guanidin-hydrochloride und verfahren zu deren herstellung
WO2004073400A2 (fr) * 2003-02-19 2004-09-02 Fraunhofer Gesellschaft zur Förderung der angewandten Forschung e.V. Matière destinée, notamment, à être introduite dans des systèmes de liants

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT505102B1 (de) * 2004-11-05 2010-05-15 Schmidt Oskar Biozid, insbesondere fungizid wirkendes mittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2408192A1 (de) * 1973-02-20 1974-09-05 Dow Corning Verbundstoff mit antimikrobieller wirkung
AT408302B (de) * 2000-05-11 2001-10-25 P O C Oil Industry Technology Biozide polymere der reihe der polyoxyalkylen-guanidin-hydrochloride und verfahren zu deren herstellung
WO2004073400A2 (fr) * 2003-02-19 2004-09-02 Fraunhofer Gesellschaft zur Förderung der angewandten Forschung e.V. Matière destinée, notamment, à être introduite dans des systèmes de liants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013064161A1 (fr) 2011-11-02 2013-05-10 Mindinvest Holdings Ltd. Silicate de polyguanidine et son utilisation
EP3524055A1 (fr) 2018-02-08 2019-08-14 BCSK Biocid GmbH Agent lubrifiant antibactérien et spermicide
WO2019154983A1 (fr) 2018-02-08 2019-08-15 Bcsk Biocid Gmbh Lubrifiant antibactérien et spermicide

Also Published As

Publication number Publication date
AT505514A1 (de) 2009-02-15
EP2197959A1 (fr) 2010-06-23
AT505514B1 (de) 2011-10-15

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