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WO2006024360A1 - Enduits contenant des particules polymeres qui comportent des composes actifs adherant particulierement bien au substrat - Google Patents

Enduits contenant des particules polymeres qui comportent des composes actifs adherant particulierement bien au substrat Download PDF

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Publication number
WO2006024360A1
WO2006024360A1 PCT/EP2005/008491 EP2005008491W WO2006024360A1 WO 2006024360 A1 WO2006024360 A1 WO 2006024360A1 EP 2005008491 W EP2005008491 W EP 2005008491W WO 2006024360 A1 WO2006024360 A1 WO 2006024360A1
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WO
WIPO (PCT)
Prior art keywords
weight
active ingredient
monomers
polymeric matrix
paints
Prior art date
Application number
PCT/EP2005/008491
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German (de)
English (en)
Inventor
Patrick Amrhein
Uwe Dittrich
Bernhard Schuler
Harm Wiese
Reinhold J Leyrer
Original Assignee
Basf Aktiengesellschaft
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
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Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2006024360A1 publication Critical patent/WO2006024360A1/fr

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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
    • A01N25/26—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 in coated particulate form

Definitions

  • the present invention relates to paints containing polymer particles of a polymeric matrix and an active ingredient with a special Substratanhaf ⁇ tion of surfaces and a good formability and the use of these An ⁇ coating agent as an antibody (repellent) against dogs, cats and masonry.
  • the active ingredient is released from the composition in a controlled manner.
  • EP 305 139 discloses such compositions and their use as insecticides.
  • No. 6,395,290 discloses sprayable compositions for repelling animals, such as cats and dogs, containing an active ingredient dispersed in a polymer.
  • the polymer is preferably an ethylene-vinyl acetate copolymer and the active ingredient is methyl nonyl ketone.
  • These compositions have the disadvantage that, although they initially contain the active ingredient and can deliver controlled, but the application form is not designed to bind permanently to a substrate. This, in turn, entails the risk of the polymer being e.g. can be easily washed off or rubbed off under mechanical stress and thus the delayed release does not come into play.
  • the polymers are generally selected so that they are used as so-called "stand-alone products", ie, that the corresponding latex particles can not be arbitrarily used as additives in existing formulations due to lack of compatibility ,
  • the active ingredients for example semiochemicals
  • EP 617 051 which are likewise introduced into a polymer matrix, have the disadvantage that they have no special adhesion to substrate surfaces and that compatibility with existing formulations is not ensured.
  • Wall spiders an introduced spider species from the Mediterranean, which belongs to the genus of the curling spiders, cause black unaesthetic discoloration on the facades through their nets.
  • Methylnonyl ketone is a colorless, highly scented oil used to repel dogs or cats. It is used commercially in liquid spray formulations.
  • the disadvantage here however, on the one hand, the only short-lasting effect due to the high volatility of the active ingredient and, secondly, the occurrence of discoloration on the sprayed materials.
  • a common problem with the incorporation of drugs into a matrix is the ratio between the uptake of the drug and the delivery / release profile. If the absorption of the active ingredient is easy, the release is often too fast. If the absorption is inhibited, then there may be no release or, if the absorption has taken place only on the surface of the particles, that it is of short duration.
  • the object of the present invention was therefore to provide a paint containing polymer particles of a polymeric matrix and an active ingredient and its use as a repellent against animals, in particular against dogs, cats or masonian spiders, in a satisfactory combination of absorption and controlled release of the active ingredient Substrate adhesion or resistance to weathering and good formability.
  • the object has been achieved by a paint containing A) 1-30% by weight of polymer particles of a) 10-60% by weight of polymeric matrix and b) 0.1-50% by weight, based on the weight of the polymeric matrix active ingredient, B) 15-65 wt .-% of an inorganic filler
  • Another object of the invention is the use of the paint as Ab ⁇ wehrstoff against dogs, cats or masonry spiders.
  • the active ingredient is released from the polymeric matrix in a controlled manner. It is particularly advantageous that the permeability of the polymer to the volatile active ingredient can be chosen in advance to achieve release at a desired and controlled rate.
  • polymeric matrix (a) are polymers containing aa) 40-95 wt .-% of at least one acrylic or methacrylic acid ester of
  • the functional groups of the monomers dd) are correspondingly chosen so that an optimal compatibility between the polymer to be administered containing Po ⁇ lymer optionally used in a corresponding formulation and the made ⁇ selected substrate surface is guaranteed.
  • the glass transition temperature of the polymeric matrix is 90-150 0 C, preferably 95-130 0 C and most preferably 98-125 0 C.
  • the explicatformulierenden active compound the original glass transition point of the pure polymer but is first lowered, the polymer is plasticized and reaches its original glass point only approximately after complete release of the active compound.
  • the acrylic or methacrylic acid esters aa) are preferably selected from the group n-, iso-, t-butyl, n-hexyl or 2-ethylhexyl acrylate, methyl methacrylate or butyl methacrylate. Particular preference is given to using methyl methacrylate.
  • the acrylic or methacrylic esters are used in amounts of 40-99% by weight, preferably 50-98% by weight and more preferably 55-97% by weight.
  • the vinylaromatic monomers bb) used are preferably styrene or styrene derivatives, such as alkylstyrenes, for example .beta.- or .gamma.-methylstyrene or vinyltoluene. They are in Quantities of 0-50 wt .-%, preferably 0-40 wt% used. Particular preference is given to using 5-30% by weight of styrene.
  • the monomers cc) are selected from the group of ethylenically unsaturated mono- or dicarboxylic acids containing 3-5 C atoms, acrylic acid or methacrylic acid are preferably used. They are used in amounts of 0-15 wt .-%, preferably 0-10 wt.%. Particular preference is given to using 5-10% by weight of methacrylic acid.
  • the monomers dd) may be C1-C8 (meth) acrylates having functional groups such as OH, NH 2, CN, C (O) -NH 2, COOR or epoxy groups, for example Urei- domethacrylat, N-methylol (meth) acrylamide, butanediol diacrylate, Methacryloxypropyltrimethylsiloxane or allyl methacrylate.
  • functional groups such as OH, NH 2, CN, C (O) -NH 2, COOR or epoxy groups, for example Urei- domethacrylat, N-methylol (meth) acrylamide, butanediol diacrylate, Methacryloxypropyltrimethylsiloxane or allyl methacrylate.
  • monomers from the series of dimethylaminopropyltrimethacrylamide, trimethylammoniumethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, trimethylammoniumpropylmethacrylamide and further acrylic acid esters containing protonatable or already quaternized amino groups They are used in amounts of 0.1-20 wt .-%, preferably 0.1-15 wt.%.
  • the release rate can be selectively controlled.
  • the substrate binding properties can be adjusted in a targeted manner by means of the corresponding monomers.
  • Active substance b) used may be an odorous substance, for example selected from the group of mercaptans, lactones, ketones, terpenes, quinines, dialkyladipate heptylnony-ladipates, methyl salicylates, cinnamaldehydes or pine oils.
  • mercaptans are isoamylmercaptan, butylmercaptan or crotylmercaptan.
  • lactones are meant, for example, ⁇ -alkyl- ⁇ -butyrolactone or ⁇ -alkyl- ⁇ -valerolactone.
  • the ketones are understood as meaning, for example, methyl nonyl ketone, ethyl butyl ketone, methyl isoamyl ketone, isobutyl heptyl ketone, ethyl amyl ketone, methyl octyl ketone, geranylacetone or heptylideneacetone, preferably methyl nonyl ketone.
  • terpenes are substances such as ⁇ -terpinyl methyl ether, citronellyl nitrile or D-limonene.
  • the active ingredient can be added to the polymeric matrix both during and after the polymerization.
  • the wt .-% - proportion of the active ingredient is 0.1-15 wt .-% based on the polymeric matrix, preferably 1-10 wt .-% and in the formulation of the active ingredient during the polymerization of the polymeric Matrix is the wt .-% - 0.1-50 wt .-%, preferably 1-40 wt .-% - share (in each case based on the polymeric matrix).
  • the polymeric matrix a) can be carried out by conventional polymerization processes as substance polymerization, solution polymerization, emulsion, dispersion or suspension polymerization. It is also possible to carry out the polymerization as a precipitation polymerization if the solubility of the polymer in the reaction mixture is sufficiently poor.
  • Emulsifiers and protective colloids can be found, for example, in Houben Weyl, Methods of Organic Chemistry, Volume XIV / 1 Macromolecular Substances, Georg Thieme Verlag, Stuttgart 1961, p. 411 ff.
  • the polymerization may be carried out in solvents or diluents, e.g. Toluene, o-xylene, p-xylene, cumene, chlorobenzene, ethylbenzene, technical mixtures of alkylaromatics, cyclohexane, technical Aliphatenmischept, acetone, cyclohexanone, tetrahydrofuran, dioxane, glycols and glycol derivatives, polyalkylene glycols and their derivatives, diethyl ether, tert.
  • solvents or diluents e.g. Toluene, o-xylene, p-xylene, cumene, chlorobenzene, ethylbenzene, technical mixtures of alkylaromatics, cyclohexane, technical Aliphatenmischept, acetone, cyclohexanone, tetrahydrofuran, dio
  • Butyl methyl ether, tetrahydrofuran, methyl acetate, isopropanol, ethanol, water or mixtures such as Isopropanol / water mixtures are carried out.
  • the solvent or diluent used is preferably water, if appropriate with proportions of up to 60% by weight of alcohols, glycols or polyalkylene glycols. Particular preference is given to using water.
  • the polymerization can be carried out at temperatures from 0 to 300, preferably from 0 to 15O 0 C and particularly preferably 20 - 12O 0 C.
  • Emulsions For the polymerization Emulsions ⁇ be used specifically temperature ranges of 0-100 0 C, preferably 5- 95 ° C.
  • M w weight-average molecular weights
  • B. from 1000 to 2 00 000, preferably 5000 - set 150000.
  • M w is determined by gel permeation chromatography.
  • the polymerization is preferably carried out in the presence of free-radical-forming compounds.
  • Suitable polymerization initiators are, for example, peroxides, hydroperoxides, peroxodisulfates, percarbonates, peroxide esters, hydrogen peroxide and azo compounds.
  • initiators which may be water-soluble or water-insoluble are hydrogen peroxide, dibenzoyl peroxide, dicyclohexyl peroxydicarbonate, dilauroyl peroxide, methyl ethyl ketone peroxide, di-tert.
  • the initiators can be used alone or mixed with each other, for. B. mixtures of hydrogen peroxide and sodium peroxodisulfate. Water-soluble initiators are preferably used for the polymerization in aqueous medium.
  • the known redox initiator systems can also be used as polymerization initiators.
  • Such redox initiator systems contain at least one peroxide-containing compound in combination with a redox coinitiator, e.g. reducing sulfur compounds, for example bisulfites, sulfites, thiosulfates, dithionites and tetra- ationates of alkali metals and ammonium compounds.
  • a redox coinitiator e.g. reducing sulfur compounds, for example bisulfites, sulfites, thiosulfates, dithionites and tetra- ationates of alkali metals and ammonium compounds.
  • peroxodisulfates with alkali metal or ammonium hydrogen sulfites, e.g. Ammonium peroxodisulfate and ammonium bisulfite.
  • the amount of the peroxide-containing compound to the redox coinitiator is 30: 1 to 0.05:
  • transition metal catalysts may additionally be used, for. Salts of iron, cobalt, nickel, copper, vanadium and manganese. Suitable salts are, for. As iron (II) sulfate, cobalt (II) chloride, nickel (II) sulfate, or copper (L) chloride. Based on the monomers, the reducing transition metal salt is used in a concentration of 0.1 ppm to 1000 ppm. So you can use combinations of hydrogen peroxide with iron (II) salts, such as 0.5 to 30% hydrogen peroxide and 0.1 to 500 ppm Mohr's salt.
  • redox coinitiators and / or Studentsgangsmetallkataly ⁇ catalysts can be used in combination with the initiators mentioned above, z. B. benzoin, dimethylaniline, ascorbic acid and or ⁇ ganisch soluble complexes of heavy metals such as copper, cobalt, iron, manganese, nickel and chromium.
  • the amounts of redox coinitiators or transition metal catalysts usually used are about 0.1 to 1000 ppm, based on the amounts of monomers used.
  • regulators In order to control the average molecular weight of the polymers, it is often expedient to carry out the copolymerization in the presence of regulators.
  • Conventional regulators may be used for this purpose, for example compounds containing organic SH groups, such as 2-mercaptoethanol, 2-mercaptopropanol, 3-mercaptopropionic acid, cysteine, N-acetylcysteine, but also sodium hypophosphite or sodium hydrosulfite.
  • the polymerization regulators are generally used in amounts of from 0.1 to 10% by weight, based on the monomers. Also by the choice of the appropriate solvent can be influenced on the average molecular weight.
  • the polymerization in the presence of diluents with benzylic H atoms leads to a reduction in the average molecular weight by Kettenübertra ⁇ supply.
  • crosslinkers such as bis (acrylic acid esters) of diols, such as ethylene glycol, diethylene glycol bisacrylate, trietylene glycol or polyethylene glycol in an amount of 0.01-5%, based on the monomers, can be used for this purpose.
  • the polymer is obtained by the process of a solution polymerization in water, usually no separation of the solvent is necessary. Be ⁇ still the desire to isolate the polymer, z. B. a spray drying or precipitation (pH, salt, temperature) are performed.
  • the solvent can be separated by passing in steam so as to obtain an aqueous solution or dispersion.
  • the polymer can also be separated from the organic diluent by a drying process.
  • the polymers are in the form of an aqueous solution with Feststoffgehal ⁇ th of preferably 10 to 60 wt .-%, in particular 20 to 55 wt .-% before.
  • component B) it is advantageous to add carbonaceous, sulphatic or siliceous fillers, such as crystalline calcium carbonate, mica, talc, barite, quartz powder or aluminum silicates.
  • inorganic fillers includes pigments such as titanium dioxide, chromium oxide or iron oxides of different colors. In general, the fillers are added in fine grain size.
  • the paints according to the invention may contain in total up to 15% by weight of customary auxiliaries D), such as low molecular weight organic substances suitable as external plasticizers, e.g. Adipinklareester or phthalic acid ester, organic solvents such as Trimethylpentandiolmonoisobutyrat, preservatives, biocides, foam-suppressing agents, thickening substances or matting agents.
  • customary auxiliaries D such as low molecular weight organic substances suitable as external plasticizers, e.g. Adipinklareester or phthalic acid ester, organic solvents such as Trimethylpentandiolmonoisobutyrat, preservatives, biocides, foam-suppressing agents, thickening substances or matting agents.
  • the water used for the emulsion polymer for the preparation of A) forms component E).
  • water can also be added in pure form to the preparations to be used according to the invention.
  • the preparation of the preparations to be used according to the invention is expediently carried out by stirring the fillers into a template composed of water, the fillers dispersing agents and optionally thickening and foam-damping agents, then optionally external plasticizers and / or organic solvent and finally a component A) as a disperse phase containing 40 to 70 wt .-% aqueous starting dispersion admits.
  • paint is understood to mean both paints and lacquers or coatings. These may be unpigmented or transparently pigmented coatings, but may also be opaque systems. Exemplary are glazes and gloss coatings, wall paints, elastic coatings, wood paints, corrosion protection paints, oil pan coatings, swimming pool paints, anti-bite paints, floor paints, barrier paints and barrier primers (against wood ingredients, Niko ⁇ tin etc) and barrier coatings (such as against carbon dioxide and water) and Muiticolor paints called.
  • the amount of active polymer particles used in a coating depends on the desired effect. In order to defend against animals, the agent concentrations appropriate to the odor must be set individually to the type of animal to be defended. For this purpose, the release rate of the active substance must be adjusted to the desired Abvid out by the choice of the polymer composition, the formulation of the coating and the queen ⁇ amount of the active substance used.
  • An optimal interaction of the dispersion with the substrate eg a wall
  • this can be optimized by copolymerizing suitable adhesion promoters or by formulating the coating.
  • Emulsifier 1 C 12 -C 14 alkyl sulfonate sodium salt, ethoxylated with 30 EO (Disponil ® FES77)
  • the original is heated under N 2 to 8O 0 C, added portion of feed 1 and feed 2 and 10 minutes anpolymerisert. Add feed 1 in 2 hours and feed 2 in 2.5 hours. Postpolymerize for 30 minutes.
  • FG 50%
  • TG 200-250 nm
  • Tg 118-122 0 C.
  • Parmetol ® A 26 Schülke & Mayr Lusolvan ® FBH, Lumiten ® N-OC 30, Acronal ® S 790, Luconyl ®: BASF Westmin ® 30 E, Omyacarb ® 5 GU: Omya Agitan ® 731: Tego Chemie Kronos ® 2043: Kronos
  • a heavily frequented by dogs wall is coated with the above-described color with a coating weight of about 300g / m 2 with typical painter technology.
  • portions with appropriate active substance-free color, others with active substance-containing paint are painted.
  • the surfaces coated with active substance-free paint are strongly darkened by Hun ⁇ deurin, the surfaces provided with the active ingredient have no corresponding discoloration. This clearly points to different dog preferences for the various segments of the wall.

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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)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des enduits contenant des particules polymères constituées d'une matrice polymère et d'une substance active qui adhère particulièrement bien aux surfaces du substrat et présente un bon potentiel de formulation. Cette invention se rapporte en outre à l'utilisation de ces enduits en tant que répulsifs à chiens, chats, et araignées de type Dictyna civica. La substance active est libérée de la composition de manière régulée.
PCT/EP2005/008491 2004-09-01 2005-08-05 Enduits contenant des particules polymeres qui comportent des composes actifs adherant particulierement bien au substrat WO2006024360A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200410042694 DE102004042694A1 (de) 2004-09-01 2004-09-01 Anstrichmittel enthaltend Polymerisatteilchen enthaltend aktive Verbindungen mit spezieller Substratanhaftung
DE102004042694.5 2004-09-01

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WO2006024360A1 true WO2006024360A1 (fr) 2006-03-09

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3474176A (en) * 1965-12-06 1969-10-21 Int Flavors & Fragrances Inc Repelling animals with ketone
US4632881A (en) * 1984-10-12 1986-12-30 Olin Corporation Pyrithione-containing bioactive polymers and their use in paint and wood perservative products
US4775532A (en) * 1983-04-14 1988-10-04 Mobil Oil Corporation Animal repellant composition
EP0617051A2 (fr) * 1987-08-24 1994-09-28 Ciba Specialty Chemicals Water Treatments Limited Compositions polymériques
US20010006668A1 (en) * 1997-08-06 2001-07-05 Larry R. Brown Sustained release animal repellents
FR2822461A1 (fr) * 2001-03-20 2002-09-27 Cami Gmc Monomeres polymerisables pour liants et core-shell incorporables dans une peinture ou un vernis

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3474176A (en) * 1965-12-06 1969-10-21 Int Flavors & Fragrances Inc Repelling animals with ketone
US4775532A (en) * 1983-04-14 1988-10-04 Mobil Oil Corporation Animal repellant composition
US4632881A (en) * 1984-10-12 1986-12-30 Olin Corporation Pyrithione-containing bioactive polymers and their use in paint and wood perservative products
EP0617051A2 (fr) * 1987-08-24 1994-09-28 Ciba Specialty Chemicals Water Treatments Limited Compositions polymériques
US20010006668A1 (en) * 1997-08-06 2001-07-05 Larry R. Brown Sustained release animal repellents
FR2822461A1 (fr) * 2001-03-20 2002-09-27 Cami Gmc Monomeres polymerisables pour liants et core-shell incorporables dans une peinture ou un vernis

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Publication number Publication date
DE102004042694A1 (de) 2006-03-02

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