EP0876162A1 - Riechstoffhaltige kunststoffharze zur regulierten abgabe von parfümkomplexen - Google Patents

Riechstoffhaltige kunststoffharze zur regulierten abgabe von parfümkomplexen

Info

Publication number
EP0876162A1
EP0876162A1 EP97900656A EP97900656A EP0876162A1 EP 0876162 A1 EP0876162 A1 EP 0876162A1 EP 97900656 A EP97900656 A EP 97900656A EP 97900656 A EP97900656 A EP 97900656A EP 0876162 A1 EP0876162 A1 EP 0876162A1
Authority
EP
European Patent Office
Prior art keywords
perfumed
resin
weight
complex
blocks
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.)
Withdrawn
Application number
EP97900656A
Other languages
English (en)
French (fr)
Inventor
Marcel Jean
Yves Aubert
Roland Leroux
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.)
JEAN, MARCEL
Arkema France SA
Original Assignee
Elf Atochem 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 Elf Atochem SA filed Critical Elf Atochem SA
Publication of EP0876162A1 publication Critical patent/EP0876162A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
    • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
    • A61L9/042—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating with the help of a macromolecular compound as a carrier or diluent

Definitions

  • the present invention relates to a new perfumed resin allowing the regular diffusion in the form of vapor of complex volatile substances.
  • the present invention relates more particularly to a perfumed resin comprising a polymeric resin of the polyetheresteramide type containing the complex volatile substances to be released, the objects shaped from said resin, their preparation process and their use for ambient perfuming.
  • plastics such as polypropylene or ethyl vinyl acetate
  • EVA seems to be the most efficient but its capacity remains very limited, generally less than 10% of its weight, and in a very restrictive way because many usual raw materials of perfumery can only be incorporated in tiny amounts proportions.
  • the perfumer therefore has recourse to bases of perfumes of simple formulation and deodorants which are often closer to the field of household and maintenance products than to the world of perfumery.
  • FR-A-1176992 describes a process for manufacturing solid perfumes which consists in the massive incorporation of a perfume in a synthetic resin; no specific resin being mentioned.
  • US-P-3926655 describes a material essentially devoid of solvent consisting of a polyamide resin, in particular the resins sold under the name versamid®, containing a fragrance essence.
  • US-P-4184099 describes devices intended to contain volatile, scenting, insecticidal or bactericidal substances consisting of polyamide resins of a nature similar to that of the resins described in US-P-3926655 but of higher molecular weight.
  • Polyolefin matrix products suitable for use in a "master-batch" process characterized by a high content of volatile perfuming substances, such as Polyiff from Flavors & Fragrance Inc., have also been described.
  • the matrices used correspond to resins based on low density polyethylene, polypropylene and ethylene vinyl acetate.
  • EP-A-0167633 describes a material for controlling harmful insects allowing the slow release of an insecticidal formulation. This material is formed by mixing and molding chlorinated polyethylene, a thermoplastic elastomer and an insecticidal ingredient.
  • EP-A-0671123 describes a material for combating harmful insects, said material comprising an elastomer comprising polyamide blocks and polyether blocks, in combination with an insecticide, such as esbiotrine.
  • a device for combating insects comprising a thermoplastic elastomer, at least one chemical mediator acting on the behavior of insects and mites and chosen from pheromones, kairomones or allomones and optionally undecylenic acid or its derivatives has been described in EP-A-0680693.
  • This document discloses the use as elastomer of elastomers comprising polyamide blocks and polyether blocks. The only example provided describes a device allowing the constant diffusion over time of the corn sesame pheromone.
  • FR-A-2675387 describes a process for preparing a perfumed object capable of withstanding drastic temperature and hygrometry conditions. This process comprises a phase of impregnating a polymeric resin of the polyetheresteramide type with a perfume by kneading (until the perfume is saturated), followed by a rest phase and an injection phase, implemented at a temperature below 100 ° C.
  • the perfumer knows that to achieve a sophisticated perfuming of the environment he will have to use comparable raw materials and formulations similar to those of body perfumes. It also seems highly desirable that the formulation of a product intended to be breathed in fairly large amounts has a level of safety comparable to that of body perfumes in contact with the skin.
  • FR-A-2579983 neither describes nor suggests that a polymer resin of polyetheresteramide type can be used for the preparation of a perfumed resin suitable for the diffusion of complex perfumed compositions according to the present invention.
  • the Applicant has surprisingly demonstrated that a perfumed resin made up of a polymeric resin of the polyetheresteramide type containing a complex perfumed composition allows a regular diffusion of all the odorous constituent substances without causing the phenomenon of separation of the diffusion of the substances according to their volatility conventionally encountered in articles of dissemination of the prior art and therefore without significant degradation of its qualities over time.
  • Such a resin therefore makes it possible to obtain sophisticated ambient perfumes comparable to body perfumes.
  • the present invention is based on the surprising effect that such a resin does not behave like a chromatographic separation support leading to a separate diffusion of the various volatile components which it contains. Unexpectedly, all the volatile constituents are released in a constant manner without any phenomenon of separation and consequently without any notable degradation of the qualities of the perfumed composition.
  • the present invention therefore provides a perfumed resin comprising:
  • PA represents the polyamide segment and PE represents the polyether segment and n is an integer representing the distribution of the repeating units; and (b) a complex scent composition.
  • the perfumed resin according to the invention comprises, by weight relative to the weight of said perfumed resin, 99% to 5% by weight of polymer resin of polyetheresteramide type and 1 to 95% by weight of a complex perfumed composition, and preferably 90 to 5% by weight of polymeric resin of polyetheresteramide type and 10 to 95% by weight of a complex perfumed composition, respectively.
  • the perfumed resin according to one embodiment the perfumed resin according to one embodiment.
  • 1 invention comprises, by weight relative to the weight of said perfumed resin, 50 to 10% by weight of polymeric resin of the polyetheresteramide type and 50 to 90% by weight of a complex perfumed composition.
  • the perfumed resin according to the invention comprises, by weight relative to the weight of said perfumed resin, about 40% by weight of polymer resin of polyetheresteramide type and about 60% by weight of a complex perfumed composition.
  • the polymer resin of the PEEA type is obtained from PA-12 blocks and PTMG blocks, preferably with a Shore A hardness of 25.
  • the complex perfumed composition comprises at least 5 components, preferably at least 20 components.
  • the invention also provides a perfumed resin, further comprising ethyl alcohol, in a proportion of 5 to 30% of the final weight, preferably about 10%.
  • This alcohol is preferably the so-called "perfumery" alcohol.
  • the invention also relates to a process for the preparation of a perfumed resin as described above by mixing the polymeric resin of the PEEA type with the complex perfumed composition.
  • the mixture is used by coating according to the drageer technique.
  • the resin mixture is incorporated
  • PEEA / complex perfumed composition of ethyl alcohol in a proportion of 5 to 30% of the final weight, preferably about 10%.
  • the present invention also relates to articles shaped from a perfumed resin as described above as well as the masterbatches obtained from such a perfumed resin.
  • the present invention also relates to the use of perfumed resins, shaped articles and masterbatches as described above for the perfume of ambience and in particular for the perfume of ambience for automobile.
  • - Figure 1 is a curve giving, as a function of time, the quantity of volatile patchouli materials released, for various supports
  • - Figure 2 is a curve giving, as a function of time, the ratio between a component of patchouli and the galaxolide released, for various supports;
  • FIG. 3a, 3b and 3c are curves giving, as a function of time, the quantity of three volatile materials specific to patchouli released, for various supports.
  • the polyetheresteramide polymer (PEEA) consists of a linear chain of rigid polyamide segments and flexible polyether segments corresponding to the formula:
  • PA represents the polyamide segment and PE represents the polyether segment and n is an integer representing the distribution of the repeating units.
  • This PEEA polymer is obtained by any suitable process; in particular the PEEA resin is obtained by reaction in the molten state between a dicarboxylic polyamide with terminal carboxylic functions of an average molecular weight of between 300 and 15,000 and a linear or branched aliphatic polyoxyalkylene glycol with terminal hydroxyl functions and with a weight average molecular between 200 and 6000, under high vacuum at temperatures between 100 and 400 ° C, in the presence of a catalyst which is for example a tetraalkyl-orthotitanate of general formula Ti (OR) 4 or a tetraalkyl-orthostannate of general formula Zn (OR) 4; R being a linear or branched aliphatic hydrocarbon radical whose number of carbon atoms is between 1 and 24 and whose content by weight relative to the reaction mixture is between 0.001 and 5%.
  • a catalyst which is for example a tetraalkyl-orthotitanate of general formula Ti (OR
  • polymers containing polyamide blocks and polyether blocks result from the copolycondensation of polyamide blocks with reactive ends with polyether blocks with reactive ends, such as, inter alia:
  • polyamide blocks with dicarboxylic ends with polyoxyalkylenated blocks with diamine ends obtained by cyanoethylation and hydrogenation of polyoxyalkylene alpha-omega dihydroxylated aliphatic sequences called polyetherdiols;
  • polyamide sequences with dicarboxylic ends originate, for example, from the condensation of alpha-omega aminocarboxylic acids, from lactams or from substantially stoichiometric combinations of dicarboxylic acids and diamines, in the presence of a chain-limiting dicarboxylic acid.
  • the polyamide blocks are PA6 or PA12.
  • the average molecular weight Mn of the polyamide blocks varies from 300 to 15,000 and preferably from 600 to 5,000.
  • the number-average molecular weight Mn of the polyether sequences is between 10 and 6000 and preferably between 200 and 3000.
  • polymers containing polyamide blocks and polyether blocks can also comprise units distributed randomly.
  • These polymers can be prepared by the simultaneous reaction of polyether and precursors of polyamide blocks. For example, polyetherdiol, a lactam (or a corresponding alpha-omega amino acid) and a chain-limiting diacid can be reacted in the presence of a little water.
  • a polymer is obtained which essentially has polyether blocks, polyamide blocks of very variable length, but also the various reactants which have reacted randomly which are distributed statistically along the polymer chain.
  • polyamide block and polyether block polymers whether they originate from the copolycondensation of polyamide and polyether blocks prepared beforehand or from a reaction in one step, exhibit, for example, Shore D hardnesses which may be between 20 and 75, and a intrinsic viscosity between 0.8 and 2.5 as measured in metacresol at 25 ° C for an initial concentration of 0.8 g / 100 ml.
  • polyether blocks are derived from polyethylene glycol, polyoxypropylene glycol or polyoxytetramethylene glycol, they are either used as such and copolycondenses with polyamide blocks having carboxylic ends, or they are aminated to be transformed into polyether diamines and condensed with blocks polyamide with carboxylic ends. They can also be mixed with polyamide precursors and a chain limiter to obtain polymers with polyamide blocks and polyether blocks having randomly distributed units.
  • the polyether can for example be a polyethylene glycol (PEG), a polypropylene glycol (PPG) or a polytetramethylene glycol (PTMG, also called poly tetrahydrofuran, PTHF).
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PTMG polytetramethylene glycol
  • PTHF poly tetrahydrofuran
  • the polyether blocks are in the polymer chain with polyamide blocks and polyether blocks in the form of diols or diamines, they are called for simplification PEG blocks or PPG blocks or PTMG blocks. It would not be departing from the scope of the present invention if the polyether blocks contained different units such as those derived from ethylene glycol, propylene glycol or tetramethylene glycol.
  • the polymer with polyamide blocks and polyether blocks comprises a single type of polyamide block and a single type of polyether block.
  • polymers with PA12 blocks and PEG blocks are used, polymers with PA12 blocks and PTMG blocks, polymers with PA6 blocks and PEG blocks, and polymers with PA6 and PTMG blocks.
  • the polymer with polyamide blocks and polyether blocks is such that the polyamide is the minor constituent by weight, that is to say that the amount of polyamide which is in the form of blocks and that which is optionally distributed statistically in the chain represents at most 50% by weight of the polymer with polyamide blocks and polyether blocks.
  • the amount of polyamide and the amount of polyether are in a weight ratio (polyamide / polyether) of between 1/1 and 1/5.
  • a polyetheresteramide advantageously used in the invention has a polyamide / polyether weight ratio of 0.3.
  • Such polymers containing polyamide blocks and polyether blocks are sold by the company Elf Atochem under the name Pebax®.
  • PEBAX any type of PEBAX can be used in the context of the present invention.
  • the flexible grades of PEBAX which have the particularity of absorbing a large quantity of volatile matter (ie 1.2 times their weight of complex volatile matter such as high-end perfumes) and then diffusing them in their entirety with great regularity over time and without causing their separation are particularly suitable in the context of the present invention.
  • PEBAX® of low hardness such as PEBAX® obtained from PA-12 and PTMG, will be used.
  • This PEEA polymer can be in the form of beads with a diameter of a few mm.
  • complex perfumed composition is understood to mean, in the context of the present invention, a composition containing at least 2 volatile aromatic components used in the composition of a perfume or a deodorant, said volatile components generally having different volatilities. Preferably, there are at least 5, advantageously at least 20 components. Perfumed compositions can contain 30 and up to 50 or even 80 components. Mention may be made, by way of example of complex compositions, of compositions of animal or vegetable origin.
  • aromatic component as used in the context of the present invention includes all volatile odorous components which can be used in the formulation of a perfume or a deodorant and includes in particular the compounds cited in the encyclopedia Kirk Othmer (vol 16, page 947-970) as well as the various known food flavors.
  • the ethyl alcohol used in the perfumed resins of the invention makes it possible to homogenize the perfume base and to promote the development of aromas and scents during desorption.
  • Ethyl alcohol, in particular perfume alcohol is very well absorbed by the polyetheresteramide and improves, by maceration or over time, the quality of a perfume or aroma extract.
  • the perfumed resin according to the present invention can be prepared by mixing the polyetheresteramide type polymer with the complex perfumed composition to be incorporated. Any mixing technique conventionally used in the prior art can be used for this purpose. The most suitable mixing operation is carried out by coating using the bezel technique, slowly rotating at 30/60 rpm, at an ambient temperature of 20 to 25 ° C, with continuous incorporation of the complex scented composition simply carried out by pouring the latter through a tap whose flow rate is regulated to prevent an excess of the perfumed composition does not interfere with the free movement of the granules in the rotating bezel.
  • the impregnation time will vary from 20 to 120 minutes to obtain granules which are dry to the touch, immediately or after a resting phase.
  • the rotation speed can be varied during impregnation, to take account of the variation in behavior of the granules, depending on whether they are either completely or partially immersed in a liquid or whether they have absorbed the liquid.
  • the speed of rotation is chosen so that the granules are preferably always in motion.
  • the temperature at which the impregnation is carried out can also be higher than ambient temperature, and preferably lower than 40-45 ° C.
  • the appearance of the impregnated granules is slightly translucent and offers interesting decorative possibilities.
  • a colorant, when added, can be added during the impregnation of the resin or preferably beforehand in the perfume base.
  • the invention also relates to a decorated object.
  • the impregnation process according to the invention also makes it possible to avoid the use of colloidal silica, such as aerosil®.
  • colloidal silica such as aerosil®.
  • ethyl alcohol denatured according to the norm of the country of consumption
  • perfume quality is the so-called "perfume quality" alcohol.
  • the perfumed resin according to the present invention can be used as it is, that is to say in the form of beads having a diameter of a few millimeters, or can be shaped into various shapes, functional or decorative. It can be easily shaped by extrusion or by molding according to the usual techniques used for the transformation of thermoplastic polymer materials.
  • the processing temperature is conventional, but can be as high as 160 ° C.
  • the perfumed resin according to the present invention can, moreover, be used for the preparation of concentrates which, for example, in the form of granules or extrudates, will be incorporated into other thermoplastic polymers according to the so-called "master-batch” method. ".
  • thermoplastic polymers can be, for example, (co) polyolefins, EVA, PVC and others.
  • the present invention relates to articles shaped from the present scented resin and masterbatches obtained from the latter.
  • a particular application of the present invention is the manufacture of room fragrance articles and more particularly of room fragrance articles for cars.
  • the perfumed resin according to the present invention allowing constant diffusion of complex perfumed compositions can therefore also be combined with systems which accelerate the diffusion of volatile substances such as ventilation, heat, or setting in motion. Furthermore, this diffusion is perfect, both with PEEAs in the form of industrial granules and thermoformed ones.
  • compositions and the articles resulting therefrom can contain any type of additive or adjuvant conventionally used by those skilled in the art.
  • Example 1 illustrate the invention without limiting it.
  • This example describes a comparative test of the absorption capacity of lavender essence by different products, namely: PEBAX®, cellulose wadding, ethylene vinyl acetate (EVA) and polyethylene (PE).
  • the essence of lavender is complex because it contains more than 20 different chemical compounds.
  • the Pebax® used is a PA12 / PTMG copolymer, having a PA12 / PTMG weight ratio of 600/2000, a melt flow index (MFI) of 10 (measured at 235 ° C., under 1 kg, with a 2mm die).
  • This example compares the diffusion capacity of Patchouli essence (more than 20 components) from different supports such as: PEBAX, cellulose wadding, EVA and PE. This test is implemented over a period of 4 months.
  • the diffusion capacity of a complex perfumed composition from different supports is compared.
  • the supports studied are: PEBAX® (identical to that of Example 1), cellulose wadding, EVA and PE.
  • the comparative test, implemented over a period of 4 months, makes it possible to study the diffusion of a composition containing essences of Patchouli and Galaxolide (one component, in solvent).
  • Example 4 The capacity of diffusion of a complex perfumed composition from different supports is compared.
  • the supports studied are: PEBAX® (identical to that of Example 1), cellulose wadding and EVA.
  • the comparative test implemented over a period of 25 days, makes it possible to study the diffusion of a composition containing Lavandin essences (more than 20 components).
  • Peak B is the broad peak between 13.10 and 13.75
  • peak C is the peak at 14.10
  • peak D is the peak at 15.20, data being obtained with pure lavandin at 125 ° C, and with an Innowax column (30m / 0.320mm / 0.5 ⁇ m).
  • FIGS. 3a, 3b and 3c The results are represented graphically in FIGS. 3a, 3b and 3c, which give the quantities of the substances corresponding to the peaks considered as a function of time, for Pebax®, EVA and cellulose wadding supports.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP97900656A 1996-01-16 1997-01-16 Riechstoffhaltige kunststoffharze zur regulierten abgabe von parfümkomplexen Withdrawn EP0876162A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9600435A FR2743566B1 (fr) 1996-01-16 1996-01-16 Nouvelle resine parfumee permettant la diffusion reguliere d'une composition parfumee complexe
FR9600435 1996-01-16
PCT/FR1997/000076 WO1997026020A1 (fr) 1996-01-16 1997-01-16 Nouvelle resine parfumee permettant la diffusion reguliere d'une composition parfumee complexe

Publications (1)

Publication Number Publication Date
EP0876162A1 true EP0876162A1 (de) 1998-11-11

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP97900656A Withdrawn EP0876162A1 (de) 1996-01-16 1997-01-16 Riechstoffhaltige kunststoffharze zur regulierten abgabe von parfümkomplexen

Country Status (3)

Country Link
EP (1) EP0876162A1 (de)
FR (1) FR2743566B1 (de)
WO (1) WO1997026020A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19754140A1 (de) * 1997-12-05 1999-06-24 Era Beschichtung Gmbh & Co Kg Innenraummaterial auf der Basis von Kunststoff, Verfahren zu dessen Herstellung und Verwendung desselben
FR2798313B1 (fr) * 1999-08-31 2001-12-28 Marcel Jean Procede d'impregnation pour la fabrication de produits en liege naturel
FR2839648B1 (fr) * 2002-05-15 2006-01-21 Marcel Jean Piece en thermoplastique moulee, decoree et impregnee de parfum ou de tout autre principe actif volatil
WO2004014438A1 (en) 2003-06-12 2004-02-19 Firmenich Sa Gels for dispensing active volatile materials
ES2287401T3 (es) * 2003-11-14 2007-12-16 THE PROCTER & GAMBLE COMPANY Composiciones polimericas para la liberacion sostenida de materiales volatiles.
USD551392S1 (en) 2005-10-12 2007-09-18 The Procter & Gamble Company Perfume sampler vaporizer
TR201706056T4 (tr) 2005-12-07 2018-03-21 Procter & Gamble Uçucu maddeleri̇n sürekli̇ salimi i̇çi̇n poli̇meri̇k bi̇leşi̇mler.
FR2897354A1 (fr) * 2006-02-16 2007-08-17 Arkema Sa Nouvelle utilisation d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol
USD570053S1 (en) 2006-04-11 2008-05-27 The Procter & Gamble Company Perfume sampler vaporizer
FR2908419B1 (fr) * 2006-11-10 2012-11-02 Marcel Jean Resine parfumee permettant la diffusion reguliere en phase gazeuse de composants aromatiques notamment enrichis d'huiles essentielles naturelles et procede de realisation de cette resine.
FR2922111B1 (fr) 2007-10-12 2012-11-02 Marcel Jean Diffuseur d'aerosols constitue d'un support monte sur un aerateur de systeme de ventilation et pouvant recevoir plusieurs systemes de recharges telle que flacon de verre avec bouchon diffuseur en bois.
JP2009155649A (ja) * 2009-02-20 2009-07-16 Firmenich Sa 活性揮発性材料を分配するためのゲル
WO2011067732A1 (en) 2009-12-04 2011-06-09 Firmenich Sa Gel air freshener
MX392209B (es) 2018-12-18 2025-03-11 Procter & Gamble Composicion para el cuidado personal con liberacion de vapor aumentada

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CH662356A5 (fr) * 1985-04-04 1987-09-30 Firmenich & Cie Article pour la diffusion de vapeurs assaississantes a base de resine polyamide et polyether.
FR2675387B1 (fr) * 1991-04-19 1995-06-23 Madec Daniel Procede d'obtention d'un objet parfume dans la masse et objet ainsi obtenu.
FR2697848B1 (fr) * 1992-11-06 1995-01-06 Atochem Elf Sa Nouvelle résine polymère chargée en acide undécylénique ou ses dérivés.

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Also Published As

Publication number Publication date
FR2743566B1 (fr) 1998-05-07
WO1997026020A1 (fr) 1997-07-24
FR2743566A1 (fr) 1997-07-18

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