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WO2008136917A1 - Concentrés de substances antimicrobiennes actives dispersées dans l'eau - Google Patents

Concentrés de substances antimicrobiennes actives dispersées dans l'eau Download PDF

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Publication number
WO2008136917A1
WO2008136917A1 PCT/US2008/005154 US2008005154W WO2008136917A1 WO 2008136917 A1 WO2008136917 A1 WO 2008136917A1 US 2008005154 W US2008005154 W US 2008005154W WO 2008136917 A1 WO2008136917 A1 WO 2008136917A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
isothiazol
methyl
active material
mass percent
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/US2008/005154
Other languages
English (en)
Inventor
Werner Bussmann
Burkhard Roessler
Wolfgang Lindner
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.)
Troy Technology Corp Inc
Original Assignee
Troy Technology Corp Inc
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
Priority claimed from US11/800,411 external-priority patent/US7652048B2/en
Priority claimed from EP20070009024 external-priority patent/EP1987716B1/fr
Application filed by Troy Technology Corp Inc filed Critical Troy Technology Corp Inc
Publication of WO2008136917A1 publication Critical patent/WO2008136917A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N25/02—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 liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/30—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 characterised by the surfactants

Definitions

  • the present invention relates to compositions of matter which enhance the stability of solid-in-liquid dispersions. More specifically, the invention relates to surfactant systems for relatively lipophilic and/or hydrophobic materials, such as active antimicrobial materials, dispersed in lipophobic and/or hydrophilic liquids.
  • Water-based antimicrobial products are in great demand because, among other reasons, various governmental bodies have begun to restrict the use of solvents which contain volatile organic carbon (VOC). These restrictions are reportedly intended to enhance human health by improving the environment. As a result, many industries are switching from organic solvents to water-based solvents, which are inherently more susceptible to biological attack. More and better antimicrobial products are needed to protect the water-based solvents, and it is widely preferred that the antimicrobial products themselves are now also water-based and free of organic solvents.
  • VOC volatile organic carbon
  • actives concentrated products with relatively higher concentrations of antimicrobially active materials (hereinafter referred to "actives") are favored by the antimicrobial product industry because concentrated products are easier to transport and store.
  • actives are lipophilic and/or hydrophobic to the extent they do not easily dissolve in water-based liquids and are better combined in the form of
  • active dispersions water-based dispersions containing active
  • pH-adjusting agents In order to meet the demand for concentrated water-based dispersions, some formulators have added pH-adjusting agents. Assuming that these pH-adjusting agents actually promote physical stability, they cannot be considered a final solution, because the change in pH which they bring about can negatively impact the performance of the actives.
  • the formulation is said to be substantially free from organic solvents.
  • Dispersants of the '413 patent reportedly include condensates of ethylene oxide or propylene oxide (including block co-polymers of ethylene oxide and propylene oxide), sodium lignin sulphonate, the sodium salt of naphthalene sulphonic acid/formaldehyde condensates and mixtures thereof.
  • the sodium lignin sulphonate-containing formulations of the '413 patent exhibit undesirably high viscosities at relatively higher concentrations.
  • the deodorizing agent of the '900 application reportedly comprises 5-70 wt% of a deodorant such as 1 ,2-benzisothiazol- 3(2H)-one or methylene bis-thiocyanate, 0.1-10 wt% xanthan gum, 0.1-0.5 wt% polyacrylamide which optionally may be partially hydrolyzed, and water.
  • a deodorant such as 1 ,2-benzisothiazol- 3(2H)-one or methylene bis-thiocyanate
  • 0.1-10 wt% xanthan gum 0.1-0.5 wt% polyacrylamide which optionally may be partially hydrolyzed, and water.
  • the polyacrylamide-containing formulations of the '900 patent exhibit undesirably high viscosities at relatively higher concentrations.
  • suspension concentrates comprising a) at least one active compound, solid at room temperature, from the group of the azoles and/or the strobilurins, b) at least one penetration enhancer from the group of the alkanolethoxylates, c) at least one dispersant from the group of the polymers of methyl 2- methyl-2-propenoate and alpha-(2-methyl-l-oxo-2-propenyl)-omega-methoxypoly-(oxy-
  • 1,2-ethanediyl 1,2-ethanediyl
  • the tristyrylphenolethoxylates and/or the propylene oxide/ethylene oxide block copolymers having molecular weights between 8000 and 10 000 d) water and also e) additives, if appropriate.
  • the alkanolethoxylates required by the '114 application are organic solvents and, therefore, inappropriate for use in organic solvent free, water-based antimicrobial products.
  • water-based dispersion compositions which include certain lipophilic and/or hydrophobic antimicrobially active materials in a dispersed phase, an acrylic graft copolymer surfactant, and an ionic alkoxylated polyarylphenol phosphate ester surfactant are stable over time at surprisingly high concentrations of the active materials.
  • the active materials may be present in dispersion concentrates of the present invention singly or in useful combinations.
  • the dispersion concentrates may be efficiently shipped and stored, and subsequently diluted with water to produce less concentrated dispersions when desired.
  • the invention is a dispersion composition which includes about 5 to about 60 mass percent of a selected antimicrobially active material in a dispersed phase.
  • the active material is selected from the group of fungicides and bactericides consisting of l,2-benzisothiazol-3(2H)-one; 2-octyl-2H-isothiazol-3-one; 5- chloro-2-methyl-2H-isothiazol-3-one; 2-methyl-2H-isothiazol-3-one; pyrithione zinc; 3- iodo-2-propynyl butylcarbamate; 2-methylthio-4-ethylamino-6-tert-butylamino-s- triazine; and 3-(4-isopropylphenyl)-l,l-dimethylurea, and mixtures thereof.
  • the dispersion composition also includes about 0.1 to about 5 mass percent of an acrylic graft copolymer having a poly(methyl methacrylate-methacrylic acid) backbone and polyethylene glycol side chains, and about 0.1 to about 5 mass percent of a tristyrylphenolethoxylate phosphoric ester or a salt thereof having an average of about 50 to about 60 ethylene oxide units.
  • the acrylic graft copolymer is a copolymer of methyl 2-methyl-2-propenoate and alpha-(2 -methyl- l-oxo-2 -propenyl)-omega- methoxypoly-(oxy- 1 ,2-ethanediyl).
  • the dispersion composition includes about 30 to about 60 mass percent of the active material, more preferably about 45 to about 55 mass percent of the active material. Even at these relatively high concentrations, the dispersion compositions of the present invention can be stored for months or years without significant loss of stability.
  • the active materials are present as solid or liquid particles dispersed in a continuous phase of water-based solvent.
  • the particles are preferably about forty microns or less in size, more preferably about fifteen microns or less.
  • the water-based solvent includes essentially no VOC and essentially no organic solvent. More preferably, the water-based solvent consists essentially of water, an optional defoamer, and an optional viscosity modifier.
  • the invention is a water-based dispersion concentrate which includes at least about 35 mass percent BIT, tristyrylphenolethoxylate phosphoric ester or a salt or acid form thereof; and an acrylic graft copolymer.
  • the dispersion concentrate exhibits no significant phase separation or change in viscosity at about 20 ° C over a period of at least about twelve months.
  • the invention is a water-based dispersion concentrate which includes at least about 45 mass percent OIT, ZPT, IPBC, TERT, IPU or mixtures thereof; a tristyrylphenolethoxylate phosphoric ester or a salt or acid form thereof; and an acrylic graft copolymer.
  • the dispersion concentrate exhibits no significant phase separation or change in viscosity at about 40 ° C over a period of at least about two months.
  • the invention is a microbial biocide produced by diluting a dispersion concentrate of the present invention.
  • the invention is a water-based dispersion composition, which includes a solid-in-liquid dispersions or a liquid-in-liquid dispersion.
  • the dispersion composition includes a nonionic polymeric surfactant.
  • the polymeric surfactant is an acrylic graft copolymer having a poly(methyl methacrylate- methacrylic acid) backbone and polyethylene oxide side chains. More preferably, the acrylic graft copolymer is a copolymer of methyl 2-methyl-2-propenoate and alpha-(2- methyl- 1 -oxo-2-propenyl)-omega-methoxypoly-(oxy- 1 ,2-ethanediyl).
  • One especially preferred acrylic graft polymer is commercially available from Crodia International of
  • the dispersion composition additionally includes an ionic surfactant, which is an alkoxylated polyarylphenol phosphate ester (or a salt or an acid form thereof).
  • the ionic surfactant may enter the water-based solvent in the form of a sodium, an ammonium or a potassium salt, and subsequently dissociate in the course of dissolving.
  • Tristyrylphenolethoxylate phosphate ester and its salt and acid forms are preferred.
  • the potassium salt of tristyrylphenolethoxylate phosphate ester (hereinafter referred to as "TSPPE”), which is commercially available from Rhodia, Inc. under the tradename Soprophor FLK, is especially preferred.
  • Examples of relatively water-insoluble antimicrobially active materials which are useful as bactericides, fungicides or algaecides in the present invention include: 1 ,2- benzisothiazol-3(2H)-one (BIT); 2-octyl-2H-isothiazol-3-one (OIT); 2-methyl-2H-5- chloro-2-methyl-2H-isothiazol-3-one (CIT); and isothiazol-3-one (MIT); pyrithione zinc
  • microbe means a minute life form such as, for example, a bacterium, fungus, mushroom, mold, smut, rust, or yeast.
  • Antimicrobially active material means a material that is known to terminate or retard the growth of at least a certain class of microbes, when the microbes are exposed to the material in amounts which are harmless to humans.
  • the antimicrobially active material is present as solid or liquid particles dispersed in a continuous phase of water-based solvent.
  • the particles are preferably about forty microns or less in size, more preferably about fifteen microns or less. This particle size range can be achieved through milling of the particles by conventional techniques. Typically, the particles are mechanically milled at room temperature in the presence of water, the polymeric surfactant and the ionic surfactant. The milling can be aided by the use of inert filler materials, such as china clay.
  • Dispersions of the selected active materials are miscible amongst themselves.
  • the BIT dispersion of the present invention can be combined easily with the OIT dispersion of the present invention, and no loss in stability results.
  • the resulting combination mixture can be diluted and brought back to original viscosity by the addition of the appropriate amount of a viscosity modifier (which may be, for example, Kelzan or xanthan gum).
  • a viscosity modifier which may be, for example, Kelzan or xanthan gum.
  • the original viscosity or the modified viscosity is at least about 2000 mPa-s and less than about 5000 mPa-s.
  • the viscosity modifier is xanthan gum in the amount of about 0.05 to about 2 mass percent, more preferably about
  • suitable substrates include in-can or dry- film coatings, adhesives, textiles, sealants, polymers emulsions, plastics, construction products, art materials, paints and varnishes, among others.
  • the water-based solvent includes essentially no VOC and essentially no organic solvent. More preferably, the water-based solvent consists essentially of water, an optional defoamer, and an optional viscosity modifier. However, it is contemplated that conventional adjuvants may be included in the dispersion compositions of the present invention in order to satisfy the preferences or applications of particular users. *
  • Some of the conventional adjuvants which may be utilized in the invention are pH-adjusting or buffering agents, preservatives, perfumes, deodorizers, colorants, dyes, defoamers, antioxidants, and additional surfactants, such as ethylene/propylene block polymers.
  • “Includes essentially no” means that the material so described is not present in the composition of interest, or is present in an amount that has at most an insignificant effect on the macroscopic properties of the composition of interest. “Optional” means that he material so described may be present but is not required.
  • Example 1 51% BIT. 1.5% TSPPE, 1.5% Graft Polymer
  • the formulation is prepared by mixing 73 parts by mass of BIT wet cake (70% active material) in 15 parts of water with the use of a dissolver apparatus (Dispermat of VMA Getzmann GmbH) operated from 500 to 2500 rpm. Under continued mixing, 1.5
  • the viscosity of the milled mixture was increased to about 2500 mPa-s by adding 0.2 parts of xanthan gum in the dissolver apparatus to produce the dispersion of Example 1.
  • the dispersion was stored at 20 ° C for twelve months, during which time the viscosity of the dispersion was periodically measured. No significant change in the viscosity of the dispersion was observed. The results are shown below in Table 1.
  • Example 1 The procedure described above in Example 1 was repeated with the materials and amounts listed below for actives OIT, ZPT, IPBC, TERB and IPU. Each of the dispersions 2a through 2e was stored at 40 ° C for two months, during which time the viscosity of the dispersion was periodically measured. No significant change in the viscosity of any of the dispersions 2a through 2e was observed. The results are shown below in Table 1.
  • ZPT 3-iodo-2-propynyl butylcarbamate
  • IPBC 2-methylthio-4-ethylamino-6-tert-butylamino- s-triazine
  • IPU 3-(4-isopropylphenyl)-l,l-dimethylurea
  • Viscosities were measured at 10 rpm with spindle No. 4 in a Brookf ⁇ eld viscometer.
  • Example 2a 50 parts of a dispersion identical to the dispersion of Example 1 and 10 parts of a dispersion identical to the dispersion of Example 2a was mixed in the dissolver apparatus, as described in Example 1. Water was added to make up 100 parts. The viscosity of the dispersion was measured as approximately 2000 mPa. The results are shown Table II.
  • Example 5 25% BIT. 25% PIT. 0.92% TSPPE, 0.92 Graft Polymer LO
  • Dispersions identical to those described above in Examples 1 and 2a were mixed in a ratio of one part to one part to produce a dispersion including a combination of actives, which exhibited good stability and viscosity similar to that of the initial dispersions. Results are shown below in Table III. L5
  • Dispersions identical to those described above in Examples 2d and 2c were mixed in a ratio of one part to one part to produce a dispersion including a combination of >0 actives, which exhibited good stability and viscosity similar to that of the initial dispersions. Results are shown below in Table III.
  • Example 7 25% TERB. 25% IPBC. 0.92% TSPPE. 0.92 Graft Polymer
  • Dispersions identical to those described above in Examples 2d and 2e were mixed in a ratio of one part to one part to produce a dispersion including a combination of actives, which exhibited good stability and viscosity similar to that of the initial dispersions. Results are shown below in Table III.
  • Viscosities were measured at 10 rpm with spindle No. 4 in a Brookf ⁇ eld viscometer.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des dispersions dans l'eau hautement concentrées de certaines substances antimicrobiennes actives lipophiles et/ou hydrophobes qui sont étonnamment bien stabilisées par une association de tensioactifs comprenant un tensioactif non ionique à base d'un copolymère greffé d'acrylique et un tensioactif de type ester de phosphate de polyarylphénol alcoxylé. Les substances actives peuvent être présentes, seules ou en association utile, dans les concentrés de substances dispersées de la présente invention. Les substances actives sont choisies dans le groupe constitué des fongicides et des bactéricides de type l,2-benzisothiazol-3(2H)-one ; 2-octyl-2H-isothiazol-3-one ; 5- chloro-2-méthyl-2H-isothiazol-3-one ; 2-méthyl-2H-isothiazol-3-one ; pyrithione de zinc ; 3-iodo-2-propynylbutylcarbamate ; 2-méthylthio-4-éthylamino-6-tert-butylamino-s-triazine ; et 3-(4-isopropylphényl)-l,l-diméthylurée, ainsi que parmi les mélanges de ceux-ci. Les concentrés de substances dispersées peuvent être facilement transportés et conservés, puis dilués avec de l'eau pour obtenir des dispersions moins concentrées si nécessaire. Même à une concentration relativement élevée, les compositions dispersées de la présente invention peuvent être conservées pendant des mois ou des années sans perte significative de stabilité.
PCT/US2008/005154 2007-05-04 2008-04-22 Concentrés de substances antimicrobiennes actives dispersées dans l'eau Ceased WO2008136917A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US11/800,411 US7652048B2 (en) 2007-05-04 2007-05-04 Water-based, antimicrobially active, dispersion concentrates
US11/800,411 2007-05-04
EP20070009024 EP1987716B1 (fr) 2007-05-04 2007-05-04 Dispersions concentrées antimicrobiennes à base d'eau
EPEP07009024.6 2007-05-04

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WO2008136917A1 true WO2008136917A1 (fr) 2008-11-13

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021985A3 (fr) * 2007-08-16 2009-12-30 Basf Se Compositions de traitement des semences et procédés associés
US9332758B2 (en) 2010-08-09 2016-05-10 Rohm And Haas Company Compositions containing 1,2-benzisothiazolin-3-one
US9756859B1 (en) 2016-08-11 2017-09-12 Troy Technology Ii, Inc. Stable aqueous dispersions of biocides

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020164266A1 (en) * 2001-03-15 2002-11-07 Peter Wachtler Microbicidal mixtures
US6506794B1 (en) * 1999-03-30 2003-01-14 Avecia Inc. Aqueous fungicide dispersion
US20040224020A1 (en) * 2002-12-18 2004-11-11 Schoenhard Grant L. Oral dosage forms with therapeutically active agents in controlled release cores and immediate release gelatin capsule coats
WO2004098289A1 (fr) * 2003-05-07 2004-11-18 Laboratorios Miret S.A. Composition antimicrobienne synergique contenant terbutryne
US20050209183A1 (en) * 2002-07-25 2005-09-22 Phenion Gmbh & Co. Kg Cosmetic or pharmaceutical preparations comprising nucleic acids based on non-methylated CPG motifs
US20050261394A1 (en) * 2004-05-20 2005-11-24 Randy Branston Polymers for paper and paperboard coatings
US20060205716A1 (en) * 2003-04-23 2006-09-14 Peter Wachtler Microbicidal agents
US20070031361A1 (en) * 2005-06-08 2007-02-08 Hans-Friedrich Herrmann Cosmetic, pharmaceutical and dermatological preparations comprising homopolymer and/or copolymer waxes of the monomers ethylene and/or propylene
US20070053944A1 (en) * 2003-09-23 2007-03-08 Bayer Cropscience Aktiengesellschaft Concentrated suspensions
US20070092544A1 (en) * 2005-08-23 2007-04-26 Mills Matthew A Natural insect repellant

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506794B1 (en) * 1999-03-30 2003-01-14 Avecia Inc. Aqueous fungicide dispersion
US20020164266A1 (en) * 2001-03-15 2002-11-07 Peter Wachtler Microbicidal mixtures
US20050209183A1 (en) * 2002-07-25 2005-09-22 Phenion Gmbh & Co. Kg Cosmetic or pharmaceutical preparations comprising nucleic acids based on non-methylated CPG motifs
US20040224020A1 (en) * 2002-12-18 2004-11-11 Schoenhard Grant L. Oral dosage forms with therapeutically active agents in controlled release cores and immediate release gelatin capsule coats
US20060205716A1 (en) * 2003-04-23 2006-09-14 Peter Wachtler Microbicidal agents
WO2004098289A1 (fr) * 2003-05-07 2004-11-18 Laboratorios Miret S.A. Composition antimicrobienne synergique contenant terbutryne
US20070053944A1 (en) * 2003-09-23 2007-03-08 Bayer Cropscience Aktiengesellschaft Concentrated suspensions
US20050261394A1 (en) * 2004-05-20 2005-11-24 Randy Branston Polymers for paper and paperboard coatings
US20070031361A1 (en) * 2005-06-08 2007-02-08 Hans-Friedrich Herrmann Cosmetic, pharmaceutical and dermatological preparations comprising homopolymer and/or copolymer waxes of the monomers ethylene and/or propylene
US20070092544A1 (en) * 2005-08-23 2007-04-26 Mills Matthew A Natural insect repellant

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021985A3 (fr) * 2007-08-16 2009-12-30 Basf Se Compositions de traitement des semences et procédés associés
AU2008288385B2 (en) * 2007-08-16 2013-11-07 Basf Se Seed treatment compositions and methods
EA019834B1 (ru) * 2007-08-16 2014-06-30 Басф Се Применение композиции, композиция для обработки семян, способ обработки семян и семена, обработанные композицией
US9137984B2 (en) 2007-08-16 2015-09-22 Basf Se Seed treatment compositions and methods
EP3150068A1 (fr) * 2007-08-16 2017-04-05 Basf Se Composition et procédé de traitement de semences
US9332758B2 (en) 2010-08-09 2016-05-10 Rohm And Haas Company Compositions containing 1,2-benzisothiazolin-3-one
US9756859B1 (en) 2016-08-11 2017-09-12 Troy Technology Ii, Inc. Stable aqueous dispersions of biocides
US10721931B2 (en) 2016-08-11 2020-07-28 Troy Technology Ii, Inc. Stable aqueous dispersions of biocides

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