WO2013131498A2 - Anti-microbial component and using of the same - Google Patents

Anti-microbial component and using of the same Download PDF

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Publication number
WO2013131498A2
WO2013131498A2 PCT/CZ2013/000029 CZ2013000029W WO2013131498A2 WO 2013131498 A2 WO2013131498 A2 WO 2013131498A2 CZ 2013000029 W CZ2013000029 W CZ 2013000029W WO 2013131498 A2 WO2013131498 A2 WO 2013131498A2
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WO
WIPO (PCT)
Prior art keywords
component according
antimicrobial component
sorbent
derivatives
antimicrobial
Prior art date
Application number
PCT/CZ2013/000029
Other languages
French (fr)
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WO2013131498A3 (en
Inventor
Vladimir SEDLARIK
Pavel KUCHARCZYK
Petr Saha
Pavel VALASEK
Original Assignee
Tomas Bata University In Zlin
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Application filed by Tomas Bata University In Zlin filed Critical Tomas Bata University In Zlin
Publication of WO2013131498A2 publication Critical patent/WO2013131498A2/en
Publication of WO2013131498A3 publication Critical patent/WO2013131498A3/en

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Classifications

    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/14—Ethers

Definitions

  • the invention deals with antimicrobial component with immobilized aromatic compounds and with the application of this component as an additive for plastics, paper and protective coating paintings and for selected food and cosmetic products.
  • Terpenes and their derivatives are natural based substances predominantly of plant origin. They create a significant share in ethereal and essential oils. Their chemical structure consists of two or more units of isoprene or their fragments. The terpenes and some of their derivatives are characteristic by their substantial aromatic properties and their odour can be noticed at low concentrations. Therefore they are used for aroma enhancement of some food or cosmetic products. Some of the terpenes are also characteristic by their antimicrobial properties active against both Gram-positive and Gram-negative bacterial strains.
  • the US patent application no. 2003113385 implements the application of extracts from plants of the genera of Leptospermum and Melaleuca containing terpenes in veterinary medicine.
  • the use of the extracts may cause lower demand of antibiotic dosage e.g. in case of mastitis treatment.
  • terpenes or their derivatives occur in liquid state at standard ambient temperature and pressure conditions (SATP, 25 °C, 101.325 kPa) and they are characteristic by the high volatility at elevated temperatures. Their vapour pressure is dependent on their chemical structure. This feature is acceptable in applications where significant increase of the processing temperature is not expected or where long-term activity of the terpenes is not demanded. However, there are several fields where these factors cannot be avoided. In these cases, uneconomic losses of terpene components can occur. Plastic processing industry can be mentioned as an example where the use of terpenes as additives is substantially limited.
  • the above mentioned disadvantages and shortcomings are largely eliminated by the antimicrobial component according the invention.
  • the nature of the technical solution consists in that it includes at least one compound from the group of isoprenoids, terpenes or their derivatives or unsaturated ethers, volatile liquid at SATP, which is immobilized on a solid carrier- sorbent.
  • the terpene based substances or its derivatives are preferably compounds that include at least one isoprene unit and/or at least one benzene ring in its chemical structure.
  • the sorbent can preferably be an organic substance based on polysaccharides or their derivatives, especially cellulose or starch, polyphenol based compound such as lignin, organic substance based on peptides and their derivatives, substance based on aluminosilicates (zeolites) and other substances containing silicon dioxide or an inorganic substance used as a plastic additive based on inorganic salts of calcium, particularly carbonates, sulphates, carbon black or talc.
  • polysaccharides or their derivatives especially cellulose or starch
  • polyphenol based compound such as lignin
  • organic substance based on peptides and their derivatives substance based on aluminosilicates (zeolites) and other substances containing silicon dioxide or an inorganic substance used as a plastic additive based on inorganic salts of calcium, particularly carbonates, sulphates, carbon black or talc.
  • zeolites aluminosilicates
  • the antimicrobial components according to the invention can be used for preparation of a polymer system in form of polymer melt or solution, where the concentration of the antimicrobial component is from 1 to 80 wt. %.
  • Another area of application of the antimicrobial component according to the invention is the preparation of antimicrobial paper products, where the concentration of the antimicrobial component is from 1 to 80 wt. %.
  • the antimicrobial component according to the technical solution can be applied for preparation of dispersions based on water-soluble polymers and their gels and films, where concentration of the antimicrobial component is from 1 to 80 wt. %.
  • Possible utilization of the antimicrobial component according to the invention is in preparation of instant food products and in cosmetics.
  • Liquid terpenes and other aromatic compounds are according to the invention in antimicrobial component immobilized on the solid sorbents that ensure their enhanced thermal stability and reduced volatility.
  • Such a modified system provides wider applicability of these compounds, especially utilization of their antimicrobial properties in a wide range of the above mentioned applications.
  • Aromatic compound Linalool (3,7-dimethylocta-l,6-dien-3-ol, CAS 78-70-6) was isothermally adsorbed at 30 °C on a zeolite based on silicon dioxide and aluminium oxide (5A CAS 1344-01-0 molecular sieves). The mass ratio Linalool :zeolite was 1 :2 at the beginning of the reaction. The remaining Linalool (not adsorbed) was evaporated at room temperature after 24 hours.
  • Adsorption of the aromatic compound Anethole ((E)-l-Methoxy-4-(l- properiyl)benzene, CAS 4180-23-8 was carried out under the same conditions as described in Example 1, except that the evaporation of the remaining Anethole took place at 70 °C after 24 hours.
  • Adsorption of the aromatic compound Estragole l-allyl-4-methoxybenzene, CAS 140- 67-0 was carried out Under the same conditions as described in Example 1, except that evaporation of the remaining Estragole took place at 50 °C after 24 hours.
  • the system consisting of Linalool, Anethole and Estragole immobilized on wood flour (dak, particle size below 500 ⁇ according to a sieve analysis) was prepared under conditions analogous to the Examples 1, 2 and 3.
  • the prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were thermoplastically incorporated into a polymer matrix (linear low density polyethylene, LDPE) in concentration range from 1 to 50 wt. % (related to the mass of the sorbent with immobilized aromatic compound) at mixing temperature of 135 °C.
  • the resulting mixtures, composites were subsequently processed into thin sheets with thickness from 0.2 to 1 mm.
  • gas barrier tested for air according the standard CSN EN ISO 2556)
  • antibacterial properties tested according the standard ISO 22196, testing bacterial strains: Escherichia coli and Staphylococcus aureus) of the composites were tested. All composites show a mild odour relating to the incorporated aromatic compound. All composites show enhanced mechanical and barrier properties minimally about 10 % in comparison with pure LDPE. All composites show noticeable antibacterial properties.
  • the prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were used as components for molded pulp preparation in a concentration range from 1 to 20 wt. % (related to the mass of the dry matter).
  • the resulting products show a feature of long- lasting release of the specific odour.
  • Resulting products show antimicrobial properties (tested against Escherichia coli and Staphylococcus aureus by the method of cultivation in liquid medium and agar diffusion technique).
  • the prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were incorporated into a gel matrix or into swollen polymer systems and/or solutions based on synthetic (polymers with C-C backbone chain, polyacrylic acid and its derivatives, polyethers, polyesters, polyurethanes) or natural (proteins, polysaccharides and their derivatives) polymers in concentration range from 1 to 90 wt. % (related to the mass of the dry polymer).
  • the resulting products show a feature of long-lasting release of the specific odour.
  • the resulting products show antimicrobial properties (tested against Escherichia coli and Staphylococcus aureus by the method of cultivation in liquid medium and agar diffusion technique).

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The antimicrobial component according to the invention includes at least one compound from the group of isoprenoids, terpenes or their derivatives or unsaturated ethers that occur in liquid state at standard ambient temperature and pressure conditions, immobilized on solid carrier -sorbent. The terpene based substance is preferably a compound containing at least one isoprene unit and/or at least one benzene ring in its chemical structure. The sorbent is preferably an organic substance based on polysaccharides or their derivatives, especially cellulose or starch, polyphenol based compound such as lignin, organic substance based on peptides and their derivatives, substance based on aluminosilicates (zeolites) and other substances containing silicon dioxide or an inorganic substance used as a plastic additive based on inorganic salts of calcium, particularly carbonates, sulphates, carbon black or talc.

Description

ANTI-MICROBIAL COMPONENT AND USING OF THE SAME
Field of Invention
The invention deals with antimicrobial component with immobilized aromatic compounds and with the application of this component as an additive for plastics, paper and protective coating paintings and for selected food and cosmetic products.
State of Art
Terpenes and their derivatives are natural based substances predominantly of plant origin. They create a significant share in ethereal and essential oils. Their chemical structure consists of two or more units of isoprene or their fragments. The terpenes and some of their derivatives are characteristic by their substantial aromatic properties and their odour can be noticed at low concentrations. Therefore they are used for aroma enhancement of some food or cosmetic products. Some of the terpenes are also characteristic by their antimicrobial properties active against both Gram-positive and Gram-negative bacterial strains.
The use of natural based monoterpenes and their derivatives as antimicrobial additives with antimicrobial effects in cosmetic, pharmaceutical and food products and in fodder is already known e.g. from the patent application PCT WO no. 2005012210.
The US patent application no. 2003113385 implements the application of extracts from plants of the genera of Leptospermum and Melaleuca containing terpenes in veterinary medicine. The use of the extracts may cause lower demand of antibiotic dosage e.g. in case of mastitis treatment.
Most of the commonly used terpenes or their derivatives occur in liquid state at standard ambient temperature and pressure conditions (SATP, 25 °C, 101.325 kPa) and they are characteristic by the high volatility at elevated temperatures. Their vapour pressure is dependent on their chemical structure. This feature is acceptable in applications where significant increase of the processing temperature is not expected or where long-term activity of the terpenes is not demanded. However, there are several fields where these factors cannot be avoided. In these cases, uneconomic losses of terpene components can occur. Plastic processing industry can be mentioned as an example where the use of terpenes as additives is substantially limited.
Nature of Invention
The above mentioned disadvantages and shortcomings are largely eliminated by the antimicrobial component according the invention. The nature of the technical solution consists in that it includes at least one compound from the group of isoprenoids, terpenes or their derivatives or unsaturated ethers, volatile liquid at SATP, which is immobilized on a solid carrier- sorbent.
The terpene based substances or its derivatives are preferably compounds that include at least one isoprene unit and/or at least one benzene ring in its chemical structure.
The sorbent can preferably be an organic substance based on polysaccharides or their derivatives, especially cellulose or starch, polyphenol based compound such as lignin, organic substance based on peptides and their derivatives, substance based on aluminosilicates (zeolites) and other substances containing silicon dioxide or an inorganic substance used as a plastic additive based on inorganic salts of calcium, particularly carbonates, sulphates, carbon black or talc.
The antimicrobial components according to the invention can be used for preparation of a polymer system in form of polymer melt or solution, where the concentration of the antimicrobial component is from 1 to 80 wt. %.
Another area of application of the antimicrobial component according to the invention is the preparation of antimicrobial paper products, where the concentration of the antimicrobial component is from 1 to 80 wt. %.
The antimicrobial component according to the technical solution can be applied for preparation of dispersions based on water-soluble polymers and their gels and films, where concentration of the antimicrobial component is from 1 to 80 wt. %.
Possible utilization of the antimicrobial component according to the invention is in preparation of instant food products and in cosmetics.
Liquid terpenes and other aromatic compounds are according to the invention in antimicrobial component immobilized on the solid sorbents that ensure their enhanced thermal stability and reduced volatility. Such a modified system provides wider applicability of these compounds, especially utilization of their antimicrobial properties in a wide range of the above mentioned applications. Examples of Technical Implementation
The following specific examples clarify the nature of the invention.
Example 1
Aromatic compound Linalool (3,7-dimethylocta-l,6-dien-3-ol, CAS 78-70-6) was isothermally adsorbed at 30 °C on a zeolite based on silicon dioxide and aluminium oxide (5A CAS 1344-01-0 molecular sieves). The mass ratio Linalool :zeolite was 1 :2 at the beginning of the reaction. The remaining Linalool (not adsorbed) was evaporated at room temperature after 24 hours.
Example 2
Adsorption of the aromatic compound Anethole ((E)-l-Methoxy-4-(l- properiyl)benzene, CAS 4180-23-8) was carried out under the same conditions as described in Example 1, except that the evaporation of the remaining Anethole took place at 70 °C after 24 hours.
Example 3
Adsorption of the aromatic compound Estragole l-allyl-4-methoxybenzene, CAS 140- 67-0) was carried out Under the same conditions as described in Example 1, except that evaporation of the remaining Estragole took place at 50 °C after 24 hours.
Example 4
' The system consisting of Linalool, Anethole and Estragole immobilized on talc (]Vlg3Si4Oi0(OH)2, CAS 14807-96-6) was prepared under conditions analogous to the Examples 1, 2 and 3.
Example 5
The system consisting of Linalool, Anethole and Estragole immobilized on wood flour (dak, particle size below 500 μηι according to a sieve analysis) was prepared under conditions analogous to the Examples 1, 2 and 3.
Example 6
The prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were thermoplastically incorporated into a polymer matrix (linear low density polyethylene, LDPE) in concentration range from 1 to 50 wt. % (related to the mass of the sorbent with immobilized aromatic compound) at mixing temperature of 135 °C. The resulting mixtures, composites, were subsequently processed into thin sheets with thickness from 0.2 to 1 mm. Further, mechanical (tensile testing according the standard CSN EN ISO 570, part 1, 2 and 3), gas barrier (tested for air according the standard CSN EN ISO 2556) and antibacterial properties (tested according the standard ISO 22196, testing bacterial strains: Escherichia coli and Staphylococcus aureus) of the composites were tested. All composites show a mild odour relating to the incorporated aromatic compound. All composites show enhanced mechanical and barrier properties minimally about 10 % in comparison with pure LDPE. All composites show noticeable antibacterial properties.
Example 7
The prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were used as components for molded pulp preparation in a concentration range from 1 to 20 wt. % (related to the mass of the dry matter). The resulting products show a feature of long- lasting release of the specific odour. Resulting products show antimicrobial properties (tested against Escherichia coli and Staphylococcus aureus by the method of cultivation in liquid medium and agar diffusion technique).
Example 8
The prepared systems with immobilized aromatic compounds specified in Examples 1- 5 were incorporated into a gel matrix or into swollen polymer systems and/or solutions based on synthetic (polymers with C-C backbone chain, polyacrylic acid and its derivatives, polyethers, polyesters, polyurethanes) or natural (proteins, polysaccharides and their derivatives) polymers in concentration range from 1 to 90 wt. % (related to the mass of the dry polymer). The resulting products show a feature of long-lasting release of the specific odour. The resulting products show antimicrobial properties (tested against Escherichia coli and Staphylococcus aureus by the method of cultivation in liquid medium and agar diffusion technique).

Claims

1. Antimicrobial component is characterized in that it includes at least one compound from the group of isoprenoids, terpenes or their derivatives or unsaturated ethers, volatile liquid at standard ambient temperature and pressure conditions, immobilized on a solid carrier - sorbent.
2. Antimicrobial component according to claim 1, is characterized in that the terpene based substance or its derivatives is a compound containing at least one isoprene unit and/or at least one benzene ring in its chemical structure.
3. Antimicrobial component according to claim 1, is characterized in that the sorbent is the organic substance based on polysaccharides or their derivatives, especially cellulose or starch.
4. Antimicrobial component according to claim 1, is characterized in that the sorbent is a ' compound based on polyphenols, such as lignin.
5. Ant microbial component according to claim 1, is characterized in that the sorbent is ah organic substance based on peptides and their derivatives.
6. Antimicrobial component according to claim 1, is characterized in that the sorbent is
"" 'a' " substance' based on alurhinosilicates (zeolites) and other substances 'containing silicon dioxide.
7. Antimicrobial component according to claim 1, is characterized in that the sorbent is " ' an inorganic substance used as a plastic additive based on inorganic salts of calcium, particularly carbonates, sulphates, carbon black or talc.
8. The Use of the antimicrobial component according to the claims 1-7 for preparation of a polymer system in form of thermoplastically prepared mixture or polymer 'solution where concentration of antimicrobial component in the system is from 1 up to
• 80 wt. %. '
9. The use. of the antimicrobial component according to the claims 1-7 for preparation of ' ' Jah antimicrobial paper products, where concentration of the antimicrobial' component is from 1 to 80 wt. %.
10. The use of the antimicrobial component according to the claims 1-7 for preparation of dispersions based on water-soluble polymers and their gels and films, where concentration of the antimicrobial component is from 1 to 80 wt. %.
11. The use of the antimicrobial component according to the claims 1-7 for preparation of instant food products and cosmetics.
PCT/CZ2013/000029 2012-03-09 2013-03-08 Anti-microbial component and using of the same WO2013131498A2 (en)

Applications Claiming Priority (2)

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CZPV2012-167 2012-03-09
CZ20120167A CZ303724B6 (en) 2012-03-09 2012-03-09 Antimicrobial component and use thereof

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WO2013131498A3 WO2013131498A3 (en) 2013-12-05

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Cited By (1)

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US20030113385A1 (en) 1998-02-02 2003-06-19 Boehringer Ingelheim Vetmedica Gmbh Use of combinations of active agents consisting of antimicrobially active substances and plant extracts containing terpene in veterinary medicine
WO2005012210A2 (en) 2003-08-01 2005-02-10 Dr. Andre Rieks - Labor Für Enzymtechnologie Gmbh Antimicrobial active preparations containing terpene derivatives

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WO2005012210A2 (en) 2003-08-01 2005-02-10 Dr. Andre Rieks - Labor Für Enzymtechnologie Gmbh Antimicrobial active preparations containing terpene derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2556509C2 (en) * 2014-02-11 2015-07-10 Государственное бюджетное образовательное учреждение высшего профессионального образования "Казанский государственный медицинский университет" Antimicrobial agent

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CZ303724B6 (en) 2013-04-03
WO2013131498A3 (en) 2013-12-05

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