EP4492977A1 - Selbstklebende, mit semiochemischer substanz imprägnierte mehrschichtige vorrichtung - Google Patents

Selbstklebende, mit semiochemischer substanz imprägnierte mehrschichtige vorrichtung

Info

Publication number
EP4492977A1
EP4492977A1 EP23716635.0A EP23716635A EP4492977A1 EP 4492977 A1 EP4492977 A1 EP 4492977A1 EP 23716635 A EP23716635 A EP 23716635A EP 4492977 A1 EP4492977 A1 EP 4492977A1
Authority
EP
European Patent Office
Prior art keywords
self
adhesive
multilayer device
semiochemical
block copolymer
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.)
Pending
Application number
EP23716635.0A
Other languages
English (en)
French (fr)
Inventor
Yannick ESCUDIE
Sylvain Bourrigaud
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.)
Ceva Sante Animale SA
Original Assignee
Ceva Sante Animale SA
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 Ceva Sante Animale SA filed Critical Ceva Sante Animale SA
Publication of EP4492977A1 publication Critical patent/EP4492977A1/de
Pending legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P17/00Pest repellants
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00Layered products comprising a layer of synthetic resin
    • B32B27/30Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, 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
    • A01N25/18Vapour or smoke emitting compositions with delayed or sustained release
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B23/00Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose
    • B32B23/04Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B38/00Ancillary operations in connection with laminating processes
    • B32B38/08Impregnating
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04Interconnection of layers
    • B32B7/12Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2250/00Layers arrangement
    • B32B2250/044 layers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00Properties of the layers or laminate
    • B32B2307/70Other properties
    • B32B2307/732Dimensional properties
    • B32B2307/737Dimensions, e.g. volume or area
    • B32B2307/7375Linear, e.g. length, distance or width
    • B32B2307/7376Thickness

Definitions

  • TITLE Self-adhesive multilayer device impregnated with a semiochemical substance
  • the present invention relates to a self-adhesive multilayer device that can be impregnated and recharged with a semiochemical substance and allows the diffusion over time of this semiochemical substance.
  • the present invention also relates to a kit comprising one or more self-adhesive multilayer devices and a composition comprising a semiochemical substance.
  • the present invention also relates to the use of this device or kit in a method of diffusing a semiochemical substance to modify behavior in an animal.
  • Semiochemical substances are volatile substances that are increasingly used in many fields, for example, to control the behavior of animals or to regulate populations of insect pests.
  • semiochemical substances are generally composed of a mixture of organic molecules. Each molecule has its own volatility and the volatilities can therefore vary a lot depending on the nature of the molecule. For the effect of the mixture to be optimal, each of the molecules that compose it must be diffused in a controlled and balanced manner.
  • One of the major problems that arises in order to be able to optimally use these semiochemical substances is the possibility of storing them and releasing them using materials allowing not only the preservation of the purity of the semiochemical substances during the manufacture of the device and during the time of use, but also controlled release at sufficient rates over long periods. Another problem is being able to load materials multiple times to avoid having to craft and use a new item for each new desired use.
  • This diffusion can be done, among other things, by wicks immersed in a reservoir bottle, but this device has the disadvantage of being bulky and expensive in terms of materials (plastic bottle, non-recyclable solid wick).
  • Another method of diffusion can be done by simply spraying semiochemical substances onto a support surface. In this case, the user faces several separate technical problems.
  • a first problem is to slow down and control the diffusion over time of semiochemical substances.
  • a second problem is the formation of an unsightly greasy stain at the spray deposition zone.
  • a third problem is the protection of the deposit against involuntary wiping of the deposit in contact with an object or fabric.
  • a compact diffuser of semiochemical substances for example in the form of a thin film, applicable to any type of surface, curved or flat.
  • the latter must make it possible to constitute a compact reservoir of semiochemical substances with a minimal volume and a large diffusion surface. It must make it possible to control the diffusion of semiochemical substances over time to extend the duration of effectiveness over 6 to 10 days, and to absorb the semiochemical substances quickly enough (of the order of a few minutes) so as to protect them from accidental wiping by contact with another surface and being able to be recharged with semiochemical substances.
  • This compact diffuser will advantageously present an aesthetic surface unaltered by the deposition of semiochemical substances.
  • thermoplastic matrix for the release of semiochemicals was described in 1996 in patent US5,504,142.
  • the matrix is a Pebax® type copolymer.
  • Pebax® is a plasticizer-free thermoplastic elastomer or flexible polyamide composed of a regular linear chain of rigid polyamide segments and flexible polyether segments.
  • this type of matrix requires the use of an acid type solvent undecylenic serving as a vector for the active substance to penetrate the copolymer matrix.
  • This solvent derived from undecylenic acid with biocidal properties well known to those skilled in the art
  • This solvent necessary for carrying out the process described in this invention is potentially harmful to the environment or can have a negative interaction with animals. The presence of such solvents is therefore prohibitive for the use of such a matrix to store and release semiochemical substances.
  • EP0338732 describes a matrix for the release and diffusion of active substances such as perfumes and pheromones in the atmosphere.
  • the matrix is permeable to the active substances and is formed of a copolymer which can be sufficiently softened at a temperature between 45°C and 160°C to incorporate the substances.
  • the matrix is formed of a substantially linear block copolymer which is a reaction product of a polydiorganosiloxane which forms soft segments in said reaction product and a diisocyanate which forms hard segments, said soft segments comprising from 70 to 99% by weight, based on the weight of said copolymer.
  • the problem with such a matrix is that its manufacture involves high temperatures not compatible with pheromones. In addition, once the pheromone has been released, it is not possible to recharge the matrix.
  • International application W001/50859 also describes a slow release insect repellent composition
  • a slow release insect repellent composition comprising an insect repellent, an oleophilic chemical product soluble in the insect repellent and a polysaccharide type matrix in which the combination of the insect repellent and the oleophilic chemical product is trapped in the matrix such that the insect repellent is released slowly from the matrix.
  • the problem with this type of composition is that solidification goes through a drying stage at temperatures incompatible with semiochemical substances which are very sensitive to heat and which will evaporate during this stage. Additionally, once the insect repellent compound is fully released, the composition cannot be refilled.
  • EP3187046 describes the use of block copolymers as a support material for diffusing pheromones, the block copolymers being used in the form of solid particles or granules of millimeter size.
  • the diffusion distance playing a primary role in the diffusion kinetics the person skilled in the art would therefore not have used such a material in the form of a thin film because he would have expected that a drastic reduction in the thickness of the material induces a drastic acceleration of the diffusion of pheromones, so that the control of this diffusion is no longer controlled.
  • FR3032972 also describes a composition comprising a polymer elastomer phase in the form of an acrylic block copolymer and an odorous active compound allowing release of said odorous active compound for a given period of time.
  • This document describes, for example, articles obtained by injection molding, extrusion, co-extrusion or extrusion/blow molding leading to the preparation of profiled parts or elements, blocks, tubes, sheets or even films.
  • the present invention therefore relates to a self-adhesive multilayer device comprising successively:
  • an active layer comprising a block copolymer and optionally a semiochemical substance, said block copolymer being an acrylic block copolymer comprising at least one alkyl polymethacrylate block and at least one alkyl polyacrylate block, a block copolymer styrenics comprising at least one block of polystyrene and at least one block of optionally hydrogenated polydiene, or a mixture of these.
  • the device according to the present invention is a device for diffusing a semiochemical substance (e.g. C4 to C18 compounds having alcohol, ketone, aldehyde, ester, alkene, alkyne, aromatic functions, etc.), positionable on numerous surfaces.
  • a semiochemical substance e.g. C4 to C18 compounds having alcohol, ketone, aldehyde, ester, alkene, alkyne, aromatic functions, etc.
  • It is a multilayer device comprising a thin polymeric film, obtained for example by extrusion, superimposed on a support structure itself composed of several layers to give the assembly the required mechanical strength, the adhesive character, and the desired aesthetic appearance.
  • This device thanks to the gradual release of a semiochemical substance, makes it possible to modify the behavior of an animal and in particular to confer a calming effect on pets, such as dogs and cats.
  • the active layer of this device is a thin layer (e.g. a few hundred micrometers) which can be easily obtained by extrusion and which can be easily impregnated with a semiochemical (e.g. by simple spraying of the semiochemical substance, pure or mixed with d other ingredients such as a solvent, on the surface of this layer).
  • a semiochemical e.g. by simple spraying of the semiochemical substance, pure or mixed with d other ingredients such as a solvent, on the surface of this layer.
  • the active layer also makes it possible to effectively release, in a controlled and balanced manner, this semiochemical substance, even when it is a mixture of active molecules, for example in the context of 'a pheromonal mixture. Indeed, despite different volatilities of the molecules making up a pheromonal mixture, the active layer makes it possible to balance the diffusion speeds of these different molecules so as to obtain the desired pheromonal activity.
  • the device according to the invention can be easily recharged by application of the semiochemical substance to its surface. surface, for example by means of a spray. Reloading the active layer does not induce any detachment of this layer despite swelling linked to the adsorption of the semiochemical substance. Thus, the active layer adheres well to the support layer via the second adhesive layer, even when it is loaded with semiochemical substance.
  • the structure of the device according to the invention in the form of a thin self-adhesive film, flexible and non-brittle, also makes it possible to conform to any type of surface, whether flat or curved.
  • its exterior appearance is preserved over time (no whitening of the active layer for example) allowing the same aesthetic to be maintained.
  • the present invention also relates to a kit comprising one or more self-adhesive multilayer devices according to the invention and a composition comprising a semiochemical substance.
  • the present invention also relates to the use of a self-adhesive multilayer device according to the invention or of a kit according to the invention for the diffusion of a semiochemical substance, in particular for the absorption and diffusion of a semiochemical substance.
  • the invention also relates to a method for diffusing a semiochemical substance comprising the following steps: a) application of a self-adhesive multilayer device according to the invention on a support, b) impregnation of the active layer of the self-adhesive multilayer device with a substance semiochemical by bringing the active layer into contact with the semiochemical substance, c) diffusion of the semiochemical substance from the active layer of the self-adhesive multilayer device, d) optionally, repetition of steps b) and c).
  • the present invention also relates to the use of a self-adhesive multilayer device according to the invention or of a kit according to the invention for modifying behavior in an animal.
  • the self-adhesive multilayer device comprises at least 4 layers, namely (1) a first adhesive layer; (2) a support layer; (3) a second adhesive layer; and (4) an active layer.
  • the first adhesive layer is intended to be adhered to a surface, while the second adhesive layer serves to adhere the active layer to the support layer.
  • the adhesive layers may be made of any suitable adhesive material (in particular to enable the device to be stuck to any type of support), such materials being well known to those skilled in the art.
  • the adhesive layers will advantageously comprise, in particular will consist of, an acrylic polymer.
  • the adhesive layers typically each have a thickness of 1 pm to 50 pm, in particular from 2 pm to 20 pm, preferably from 5 pm to 15 pm. Such thickness can be measured by optical microscopy.
  • the first adhesive layer can additionally be protected by a protective layer.
  • This protective layer will be removed before use, that is to say just before sticking the self-adhesive multilayer device on the chosen support.
  • the support layer will typically be a layer of cellulose, that is to say paper, or even a metal or plastic film.
  • the device according to the invention may comprise a layer of ink, not uniformly distributed, between the support layer and the second adhesive layer.
  • the support layer typically has a thickness of 1 pm to 200 pm, in particular from 5 pm to 150 pm, preferably from 10 pm to 100 pm, for example around 50 pm. Such thickness can be measured by optical microscopy.
  • the active layer is intended to be in contact with the ambient air. It is made up of a film with absorption and diffusion capacities of semiochemical substances thanks to the microstructure of its material. Diffusion occurs slowly according to a kinetic profile adapted to the application. Once the semiochemical substance has been diffused, the film can then be recharged with the semiochemical substance by bringing the film into contact with a composition containing the semiochemical substance.
  • This film is also flexible and deformable so that it can be positioned on non-flat surfaces and conform to the surface to which it is applied.
  • the film material will have a tensile Young's modulus less than or equal to 1500 MPa (measured according to ISO 527) and an elongation at break greater than or equal to 20% (measured according to ISO 527).
  • this film also has the property of being transparent so as to be able to see, through transparency, the support layer on which it is applied. This allows you to see any decoration printed on the support layer.
  • the film material will have a HAZE of less than or equal to 20% (measured according to ISO 13468) and a light transmittance (TL) greater than or equal to 80% (measured according to ISO 13468).
  • the active layer thus comprises a block copolymer and optionally a semiochemical substance, said block copolymer being an acrylic block copolymer comprising at least one alkyl polymethacrylate block and at least one alkyl polyacrylate block, a styrenic block copolymer comprising at least one block of polystyrene and at least one block of optionally hydrogenated polydiene, or a mixture of these.
  • the block copolymer is an acrylic block copolymer.
  • block copolymer also called “block copolymer” is understood to mean a copolymer containing, in particular consisting of, a linear sequence of several different blocks, each block consisting of a polymer chain , two adjacent blocks therefore being made up of different polymer chains.
  • a block copolymer constitutes a single macromolecule, such that each block is covalently linked to the next block, either directly through a covalent bond or through a constituent unit that is not an integral part of the blocks.
  • the polymer chain constituting a block will advantageously result from the polymerization of one or more, in particular 1 or 2, monomer species, preferably one monomer species.
  • alkyl is meant a monovalent, linear or branched saturated hydrocarbon group.
  • the alkyl group advantageously comprises 1 to 10 carbon atoms ((CrCio)alkyl), in particular 1 to 8 carbon atoms ((CrCs)alkyl), in particular 1 to 6 carbon atoms ((CrCôjalkyl), preferably 1 to 4 carbon atoms ((CrC4)alkyl).
  • the diene advantageously comprises 4 to 10 carbon atoms, in particular 4 to 8 carbon atoms, in particular 4 to 6 carbon atoms, preferably 4 or 5 carbon atoms. This may be, for example, butadiene or isoprene.
  • polydiene we mean a polymer resulting from the polymerization of a diene.
  • the block copolymer is advantageously a bi-block copolymer or a tri-block copolymer, preferably a tri-block copolymer.
  • the block copolymer is a tri-block copolymer, it advantageously comprises at most 2 identical blocks, preferably it comprises 2 identical blocks, in particular 2 blocks of polyalkyl methacrylate or polystyrene.
  • the block copolymer comprises at least one alkyl polymethacrylate block and at least one alkyl polyacrylate block.
  • the alkyl polymethacrylate is advantageously polymethyl methacrylate (PMAA ⁇ ) and/or the alkyl polyacrylate is advantageously polybutyl acrylate (P ⁇ Bu) or a copolymer of butyl acrylate and 2-ethyl-hexyl acrylate, preferably is polybutyl acrylate (P ⁇ Bu).
  • the acrylic block copolymer is advantageously a bi-block copolymer or a tri-block copolymer, preferably a tri-block copolymer.
  • the acrylic block copolymer is a tri-block copolymer, it advantageously comprises at most 2 identical blocks, preferably it comprises 2 identical blocks, in particular 2 blocks of polyalkyl methacrylate.
  • the acrylic block copolymer is a tri-block copolymer of the PMMA-PABu-PMMA type. This could be Nanostrength® M53 copolymer.
  • the block copolymer when the block copolymer is a styrenic block copolymer, the block copolymer comprises at least one polystyrene block and at least one optionally hydrogenated polydiene block.
  • the possibly hydrogenated polydiene could be polybutadiene, polyisoprene, polyethylene-butylene (resulting from the hydrogenation of polybutadiene), or even polyethylene-propylene (resulting from the hydrogenation of polyisoprene).
  • the styrenic block copolymer is advantageously a bi-block copolymer or a tri-block copolymer, preferably a tri-block copolymer.
  • the styrenic block copolymer is a tri-block copolymer, it advantageously comprises at most 2 identical blocks, preferably it comprises 2 identical blocks, in particular 2 polystyrene blocks.
  • the styrene block copolymer is a tri-block copolymer of the SBS (styrene-butadiene-styrene), SIS (styrene-isoprene-styrene), SEBS (styrene-(ethylene-butylene)-styrene) type, or even SEPS ( styrene-(ethylene-propylene)-styrene).
  • SBS styrene-butadiene-styrene
  • SIS styrene-isoprene-styrene
  • SEBS styrene-(ethylene-butylene)-styrene
  • SEPS styrene-(ethylene-propylene)-styrene
  • the active layer typically has a thickness of 5 pm to 500 pm, in particular from 10 pm to 400 pm, in particular from 20 pm to 300 pm, for example from 50 pm to 250 pm, preferably from 100 pm to 250 pm, for example example of around 200 pm. Such thickness can be measured by optical microscopy.
  • This active layer can be prepared by extrusion and calendering. This allows you to obtain a film of the required thickness.
  • the active layer may also include a semiochemical substance. If the active layer does not contain such a substance, it may subsequently be impregnated with such a semiochemical substance.
  • the active layer in particular when it is impregnated with a semiochemical substance, can be protected by a protective layer, preferably waterproof, to be removed at the time of use, once the device is stuck on the chosen support.
  • a protective layer preferably waterproof
  • This layer of protection may be made of any suitable material well known to those skilled in the art. This could for example be an aluminized protective layer.
  • the semiochemical substance will advantageously represent from 1% to 80%, in particular from 1% to 50%, in particular from 2% to 40%, more particularly from 5 to 30%, preferably from 5% to 20%. % by weight relative to the weight of the active layer.
  • siochemical substance describes a chemical substance emitted by a plant or an animal into the environment and which serves as a signal between living beings. It can consist of a molecule or a mixture of molecules.
  • the semiochemical substance will more particularly be an animal pheromone, in particular a mammalian pheromone.
  • Semiochemicals can be perceived by different organs. Thus, semiochemical substances can be perceived by smell for volatile compounds, or by taste for non-volatile compounds.
  • the information carried by semiochemical substances can allow the location and recognition of a sexual partner, for example.
  • Semiochemical substances and more particularly pheromones are chemical compounds of which a large number of examples (8000) are given in the database accessible online Pherobase (www.pherobase.com).
  • the semiochemical substance is a semiochemical substance with a fatty chain, and is advantageously chosen from the group of pheromones, in particular animal pheromones. It will more particularly be a volatile substance.
  • volatile refers to the ability of the semiochemical substance to pass from the liquid state to the gaseous state, under ambient conditions of pressure and temperature, that is to say at approximately 20° C and at atmospheric pressure (1013.25 hPa).
  • a “volatile” liquid is a liquid whose saturated vapor pressure at 20° C is greater than 1 Pa, preferably it is between 1 Pa and 3000 Pa, in particular between 1 Pa and 2500 Pa, more preferably between 1 Pa and 1500 Pa, more preferably between 1 Pa and 1000 Pa, in particular between 1 Pa and 700 Pa.
  • fatty chain is meant, for the purposes of the present invention, an aliphatic hydrocarbon chain, preferably linear or branched, saturated or unsaturated, comprising 5 to 24, in particular 5 to 18, preferably 6 to 16, atoms of carbon.
  • the semiochemical substance according to the invention will advantageously be chosen from alkanols and alkenols having from 5 to 18 carbon atoms, alkanals and alkenals having from 5 to 18 atoms carbon, alkanones having 6 to 18 carbon atoms, alkyl or alkene acetates having 5 to 18 carbon atoms, 1,7-dioxaspirononane, 3- or 4-hydroxy-1,7 -dioxaspiro- undecane, benzyl alcohol, Z-(9)-tricosene (muscalure), heneicosane, diacetyl, alkanoic acids having 5 to 16 carbon atoms (eg caprylic acid, laurylic acid ), pinene, methyleugenol, eugenol, 4-methoxy-cinnamaldehyde, estragol, indole, ethyldodecanoate, tert-butyl 4-chloro-2-
  • the semiochemical substance can be chosen from ferrugineol, ferrugineone or a ferrugineol-ferrugineone mixture.
  • fatty chain pheromones are Z-5-decenyl acetate, dodecanyl acetate, Z-7-dodecenyl acetate, E-7-dodecenyl acetate, Z-8-dodecenyl acetate, E- 8-dodecenyl acetate, Z-9-dodecenyl acetate, E-9-dodecenyl acetate, E-10-dodecenyl acetate, 11-dodecenyl acetate, Z-9,11-dodecadienyl acetate, E-9, 11 - dodecadienyl acetate, Z-11 -tridecenyl acetate, E-11 -tridecenyl acetate, tetradecenyl acetate, E-7-tetradecenyl acetate, Z-8-tetradecenyl acetate, E-8-tetradeceny
  • the semiochemical substance according to the invention could also be chosen from fatty acid esters, and more particularly methyl or ethyl fatty acid esters, the fatty acid advantageously having from 5 to 18 carbon atoms and in particular from 8 with 18 carbon atoms. This could be methyl laurate.
  • the semiochemical substance is chosen from the group of pheromones, in particular animal pheromones, in particular mammalian pheromones.
  • the mammals according to the invention are preferably chosen from dogs, cats, horses, cattle and pigs.
  • the animal pheromone in particular of mammals, can thus be chosen from the pheromones of dogs, cats, horses, cattle and pigs.
  • the animal pheromone is a soothing pheromone.
  • mammalian pheromones are soothing pheromones such as apasin which is secreted by females during breastfeeding or facial pheromones in cats.
  • the pheromones according to the invention are natural or synthetic pheromones.
  • the semiochemical substance can be protected against the action of light and/or oxygen, in particular by the use of antioxidant and/or anti-UV agents.
  • the active layer may also contain at least one additive chosen by antioxidant agents, anti-UV agents and their mixtures.
  • the antioxidant agents may be chosen from the group consisting of vitamin E, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and mixtures thereof. These antioxidants protect the semiochemical substance from degradation by oxygen and can be added in quantities ranging from 0.1% to 3%, particularly between 0.5% and 2% by weight relative to the weight of the active layer.
  • the anti-UV agents can be chosen from the group consisting of beta-carotene, p-aminobenzoic acid, hindered amines and hindered alkoxyamines and mixtures thereof.
  • the hindered amines may be derivatives of 4-tetramethyl-piperidine, notably known under the name HALS (“hindered amine light stabilizers”) and described in Schaller, C., Rogez, D. & Braig, A. “Hindered amine light stabilizers in pigmented coatings. » J Coat Technol Res 6, 81 -88 (2009).
  • Hindered alkoxyamines can be, for example, TEMPO from Solvay.
  • the self-adhesive multilayer device according to the invention may have any size and any shape, depending on the intended application. KU
  • the kit according to the invention comprises one or more self-adhesive multilayer devices according to the invention and a composition, preferably liquid, comprising a semiochemical substance.
  • the self-adhesive multilayer devices according to the invention do not include a semiochemical substance.
  • the active layer of these devices will advantageously be impregnated with a semiochemical substance using the composition included in the kit.
  • This impregnation could be carried out for example by spraying, by brushing or rolling, or by dipping, preferably by spraying, preferably once the device is stuck on the chosen support.
  • the composition advantageously comprises, in particular consists of, a semiochemical substance, optionally solubilized in a solvent.
  • the solvent may in particular be an ether such as di(propylene glycol) methyl ether, an alcohol such as isopropanol, etc.
  • the composition does not contain any solvent.
  • the composition may also include one or more antioxidant agents and one or more anti-UV agents as defined above in order to protect the semiochemical substance against the action of UV and/or oxygen.
  • Additives such as stabilizers, preservatives or even rheology agents may possibly be present in the composition.
  • the composition will preferably be contained in a container allowing it to be sprayed. It can also be contained in a container equipped with a drip system or a brush.
  • the self-adhesive multilayer device according to the invention and the kit according to the invention are useful for the diffusion of a semiochemical substance, in particular according to a method comprising: a) the application of a self-adhesive multilayer device according to the invention on a support , b) impregnation of the active layer of the self-adhesive multilayer device with a semiochemical substance by bringing the active layer into contact with the semiochemical substance, c) diffusion of the semiochemical substance from the active layer of the self-adhesive multilayer device, d) optionally, repeating steps b) and c).
  • Step a) can be carried out before or after step b). Step a):
  • the self-adhesive multilayer device according to the invention can be applied to any type of support, whether flat or curved, since its flexible structure allows the device to conform to the shape of the support, and whatever the material of the support.
  • the support can be made of a material chosen from the group consisting of glass, textile, paper, cardboard, plastic, brick, concrete, wood, leather, vegetable fibers, metal, ceramics, and a combination thereof.
  • a support may comprise or consist of a more or less extensive and more or less flat continuous surface such as a wall, opaque or transparent, for example a wall, a floor, a glazed area such as a window, a piece of furniture, for example a cupboard, or a plastic crate.
  • a support can also include an article, that is to say a discrete or individualized object.
  • This item may be in the form of a stake, a stake, a fence, a palisade, a staple, a hook, a cardboard plate, a plastic plate. glass, a plastic plate, a metal plate, a cloth, a tarpaulin, a bag, a transport box, a T-shirt, etc.
  • the impregnation of the active layer can be carried out by simply bringing the active layer into contact with a composition, preferably liquid, comprising or consisting of the semiochemical substance, such as the composition of the kit according to the present invention.
  • the composition preferably liquid, will advantageously comprise, in particular consist of, a semiochemical substance, optionally dissolved in a solvent.
  • Additives such as stabilizers, preservatives or even rheology agents may possibly be present in the composition.
  • the solvent may in particular be an ether such as di(propylene glycol) methyl ether, an alcohol such as isopropanol, etc.
  • the composition does not contain any solvent.
  • Such contacting can be carried out for example by spraying the composition onto the active layer, by brushing or rolling the active layer with the composition, or by dipping the active layer in the composition.
  • the active layer is impregnated with the semiochemical substance, the semiochemical substance will be able to gradually diffuse through this active layer and modify the behavior in an animal in its immediate environment.
  • An advantage of the device according to the invention is its ability to be recharged with semiochemical substance, which makes it possible to repeat steps b) and c) one or more times.
  • the active layer of the device according to the invention can be re-impregnated with a semiochemical substance according to the conditions of step b).
  • the present invention also relates to the use of a self-adhesive multilayer device according to the invention or of a kit according to the invention for modifying behavior in an animal.
  • Pheromones will influence the behavior of animals such as pets, horses, pigs, which are subject to stressful situations (noises, transport, separation, etc.) linked to their environment.
  • the pheromones will be chosen according to the animal (e.g. dog, cat, etc.) for which we wish to modify the behavior depending on the situation encountered. For example, the pheromone could be chosen to soothe the animal during transport.
  • the animal crate is very often a stressful situation because the animal loses its bearings and is confronted with new stimuli, both olfactory and visual.
  • the pheromone is an animal pheromone, in particular a mammalian pheromone.
  • the mammals according to the invention are preferably chosen from dogs, cats, horses, cattle and pigs.
  • the animal pheromone in particular of mammals, can thus be chosen from the pheromones of dogs, cats, horses, cattle and pigs.
  • the animal pheromone is a soothing pheromone.
  • mammalian pheromones are soothing pheromones such as apasin which is secreted by females during breastfeeding or facial pheromones in cats.
  • Example 1 Absorption property depending on the nature of the impregnation material used
  • the tested materials are injected in the form of 5 ⁇ tensile specimens (ISO 3167).
  • the test pieces are weighed then brought into contact with methyl laurate by dipping in a methyl laurate bath at a temperature of 20° C.
  • the test pieces are recovered after one hour, drained and quickly washed on the surface with ethanol, then air dried and weighed. The difference in weight observed in relation to the initial mass of the test piece represents the quantity impregnated.
  • the test pieces are then diffused in a ventilated oven at 30° C for several days. The results are presented in Table 1 below.
  • Nanostrength® M53 (acrylic block copolymer according to the invention) thus has a high adsorption (impregnation) capacity associated with a diffusion of methyl laurate (semiochemical substance) that is sufficiently long and controlled over time (retention capacity).
  • Example 2 Physical measurement on 5 a test pieces made of raw material and material impregnated with methyl laurate
  • tensile specimens are tested on tensile test benches or on a durometer. They may or may not have been previously impregnated with methyl laurate (LM) following the method described in example 1.
  • the impregnation rate is modulated by leaving the test pieces in the methyl laurate solution for a longer or shorter time. Young's modulus, elongation at break and Shore hardness are then measured according to standard ISO 527 for Young's modulus and elongation at break and according to standard ISO 868 for Shore hardness. The results obtained are presented in Table 2 below. [Table 2]
  • Nanostrength® M53 objects of different thicknesses were impregnated with a defined quantity of methyl laurate (LM) at room temperature by depositing the methyl laurate on the surface to be impregnated.
  • LM methyl laurate
  • the first object is a self-adhesive multilayer device according to the invention of 5 x 5 cm 2 comprising: a first adhesive layer of acrylic polymer of approximately 10 pm; a layer of paper (cellulose) of approximately 50 pm screen-printed with ink; a second adhesive layer of acrylic polymer of approximately 10 pm; a Nanostrength® M53 polymer film of approximately 200 pm.
  • the second object is a Nanostrength® M53 plate measuring 5 x 5 cm 2 with a thickness of 5 mm. In both cases, the impregnation yield is greater than 99%.
  • Nanostrength® M53 material intended to be impregnated with methyl laurate
  • the device according to the invention diffuses more with a residual quantity of methyl laurate of 11% after 144 hours while the very thick material displays more than 25% of residual methyl laurate. Furthermore, the device according to the invention shows better control of broadcasting in the first hours of broadcasting.
  • the diffusion efficiency over a given period, 6 days in the example is better for the device according to the invention with 88.2% of methyl laurate diffused compared to only 73.2% for the very thick material.
  • - Formulation ⁇ semiochemical substance solubilized in a penetrating organic solvent
  • formulation ⁇ makes it possible to facilitate the penetration of the semiochemical substance into the material of the active layer.
  • Formulation B eliminates the need for a solvent since only the semiochemical substance penetrates the material of the active layer, just like formulation C.
  • the mixture is homogenized.
  • the mixture is then sprayed onto a device according to the invention at a distance of 5 cm.
  • the impregnation rate observed after 30 min is 99% of the mixture.
  • the mixture is homogenized.
  • the mixture is then sprayed onto a device according to the invention at a distance of 5 cm.
  • the observed impregnation rate is 3.7% of the mixture with an impregnation yield of the 2 active ingredients of 92%.
  • a mixture of 20/80 (w/w) of methyl laurate and methyl oleate is introduced into a bottle fitted with a drip device.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP23716635.0A 2022-03-17 2023-03-17 Selbstklebende, mit semiochemischer substanz imprägnierte mehrschichtige vorrichtung Pending EP4492977A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2202365A FR3133523B1 (fr) 2022-03-17 2022-03-17 Dispositif multicouche autocollant imprégné d’une substance sémiochimique
PCT/FR2023/050381 WO2023175284A1 (fr) 2022-03-17 2023-03-17 Dispositif multicouche autocollant imprégné d'une substance sémiochimique

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US4703070A (en) 1986-07-16 1987-10-27 Union Camp Corporation Silicone rubber containment of organic liquids
US4908208A (en) 1988-04-22 1990-03-13 Dow Corning Corporation Matrix for release of active ingredients
AU631129B2 (en) 1988-06-17 1992-11-19 E.I. Du Pont De Nemours And Company Pesticidal compositions
FR2719450B1 (fr) 1994-05-06 1996-05-31 Atochem Elf Sa Dispositif pour lutter contre les insectes.
US5705175A (en) * 1996-02-29 1998-01-06 Pennzoil Products Company Non-aqueous controlled release insect repellent and insecticide gels
CR5524A (es) 2000-01-10 1997-12-10 Tucci Asscoates Inc Formulaciones y usos del repelente de insectos de liberación lenta
DE102004033242A1 (de) * 2004-07-08 2006-02-02 Tesa Ag Haftklebemasse
AU2012206626A1 (en) 2011-01-14 2013-08-01 Basf Se Poly(meth)acrylate based microcapsules comprising pheromone
MX2014011384A (es) * 2012-03-23 2015-03-09 Celanese Eva Performance Polymers Inc Materiales repelentes de insectos de liberacion controlada.
CN104244711B (zh) 2012-04-16 2016-08-24 巴斯夫欧洲公司 包含丙烯酸、聚(亚烷基二醇)(甲基)丙烯酸酯和(甲基)丙烯酸烷基酯的共聚物的农用配制剂
FR3032972B1 (fr) 2015-02-20 2019-05-10 Arkema France Polymeric composition absorbing, comprising and releasing an odoriferous active compound, method for preparing it and its use
FR3046334B1 (fr) 2015-12-31 2020-03-06 Melchior Material And Life Science France Composition solide pour le relargage controle de substances semiochimiques
US11697904B2 (en) * 2017-01-27 2023-07-11 The Procter & Gamble Company Active agent-containing articles that exhibit consumer acceptable article in-use properties

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FR3133523B1 (fr) 2025-06-13
WO2023175284A1 (fr) 2023-09-21
FR3133523A1 (fr) 2023-09-22

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