WO2018157221A1 - Emulsifying mixture and aerosol composition - Google Patents

Emulsifying mixture and aerosol composition Download PDF

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Publication number
WO2018157221A1
WO2018157221A1 PCT/BR2018/050042 BR2018050042W WO2018157221A1 WO 2018157221 A1 WO2018157221 A1 WO 2018157221A1 BR 2018050042 W BR2018050042 W BR 2018050042W WO 2018157221 A1 WO2018157221 A1 WO 2018157221A1
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present
weight
aerosol composition
aerosol
mixture
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PCT/BR2018/050042
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French (fr)
Portuguese (pt)
Inventor
Elvis Araujo BARRETO
Claudivania Pereira CELESTINO
Juliana Pierobon STELLE
Original Assignee
Oxiteno S.A. Indústria E Comércio
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Publication of WO2018157221A1 publication Critical patent/WO2018157221A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • 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
    • A61L9/01—Deodorant compositions
    • A61L9/012—Deodorant compositions characterised by being in a special form, e.g. gels, emulsions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols

Definitions

  • the present invention relates to an emulsifying mixture for use in aerosol composition as well as an aerosol composition having low viscosity and excellent stability.
  • Emulsions are defined as a heterogeneous system of at least two immiscible liquids, one called a continuous phase and the other a dispersed phase.
  • the dispersed (internal) phase is distributed as droplets in the continuous (external) phase.
  • the system needs emulsifying agents to stabilize. These agents have two basic functions: the first is to decrease interfacial tension by favoring emulsion formation and the second is to avoid dispersion phase coalescence.
  • the emulsions may be water-in-oil (A / O) or oil-in-water (O / A).
  • water-in-oil (W / O) emulsions water is dispersed in the oil which acts as an external phase.
  • oil-in-water (O / W) emulsions oil is the dispersed phase and water is the continuous phase.
  • Surface or interfacial tension can be defined as the force per unit length that prevents contact surface breakage between the two phases.
  • force When force is applied at the interface between a liquid and a gas, it is called surface tension, which is dependent on the temperature and concentration of the components at the interface. Usually, the surface tension decreases when the temperature increases except for some liquid metals.
  • Emulsions have a natural tendency to separate into their two constitutive phases, decreasing the interfacial area and hence the interfacial energy.
  • An emulsion is considered stable when little or no change occurs in phase droplet size. disperses over a certain time interval
  • An emulsifier is a substance composed of molecules with both hydrophilic (polar, water-like) and lipophilic (non-polar, oil-like) regions. Its action is a result of the nature of its molecules.
  • the emulsifier is placed at the interface of the mixture.
  • the hydrophilic (head) part is oriented towards the polar phase of the system, while the lipophilic (tail) part is oriented towards the non-polar phase.
  • the emulsifier molecules are formed with the hydrophilic part positioned into the dispersed phase.
  • the emulsifier molecules are reversed with the hydrophilic part out of the dispersed phase.
  • Patent PI 0818368-6 describes aerosol composition comprising: 0.01% to 1.00% by weight sodium borate; 0.01% to 1.50% by weight of polyglycerol ester surfactant; up to 30% by weight of propellant; and 67.5% to 85.0% by weight of water. Methods of making an aerosol air flavorant are also described, wherein the aerosol composition still comprises a fragrance.
  • WO2012 / 089184 refers to a system A nanocapsule colloidal carrier, wherein the system is useful for preventing skin aging, comprising a lipid and shell nucleus, wherein the core contains a forming membrane, a natural anionic emulsifying agent and a non-co-emulsifier. single chain natural ionic.
  • the present invention provides a solution to this technical problem by providing a synergistic emulsifier mixture.
  • the invention describes an emulsifier mixture and an aerosol composition prepared from an emulsion and emulsifier mixture.
  • Said aerosol composition has the advantage of low viscosity and excellent emulsion stability, thus making it unnecessary to agitate the aerosol product prior to its application.
  • Said aerosol composition may also receive the addition of fragrances or actives during the filling line, without compromising its stability.
  • the present invention relates to an emulsifier mixture for use in water-in-oil emulsions in aerosol compositions with low viscosity and excellent stability.
  • the emulsifier mixture comprising mineral oil and a polyglycerol ester employed in the present invention is preferably a tetraglycerin oleate and variations thereof.
  • the mineral oil is present in the mixture in a range ranging from 5 to 20% by weight and the polyglycerol ester is present in a range ranging from 95 to 80% by weight. emulsifying mixture.
  • mineral oil is present in a range ranging from 5 to 10% by weight and the polyglycerol ester is present in a range ranging from 95 to 90% by weight of the emulsifier mixture.
  • the aerosol composition prepared according to the present invention comprises the emulsifier mixture, a solvent of fossil origin and water. Additionally, the aerosol composition comprises a fragrance, up to 10% by weight of the composition, and an anti-corrosive compound.
  • the solvent is a solvent of fossil origin and the fragrance is present or not in the aerosol composition, as well as other supporting materials in the final composition of the product.
  • the anti-corrosive compound is preferably sodium benzoate, present in a range between 0.02 and 0.1% by weight of the composition.
  • the aerosol composition prepared from the emulsifier mixture of the present invention has a viscosity below 5000 mPa.s, and excellent stability in water-in-oil emulsions and a pH at 25 ° C ranging from 6 to 8.
  • the aerosol composition of the present invention has the advantage of being ready for use, ie there is no need to agitate the product before applying it and can be used in various aerosol products such as odorants. and room deodorizers, insecticides, polishes furniture and household and institutional products intended for general cleaning.

Abstract

The present invention describes an emulsifying mixture and an aerosol composition prepared from an emulsion and the emulsifying mixture. More specifically, the emulsifying mixture comprises mineral oil and a polyglycerol ester, in which the mineral oil is present in the mixture in a range of from 5 to 20% by weight and the polyglycerol ester is present in a range of from 95 to 80% by weight. Preferably, the polyglycerol ester is triglyceride oleate and variations thereof. Said aerosol composition has the advantage of having low viscosity and excellent emulsion stability, thus making it unnecessary to shake the aerosol product prior to application thereof.

Description

"MISTURA EMULSIFICANTE, E, COMPOSIÇÃO AEROSSOL"  "EMULSIFYING MIX, AND, AEROSOL COMPOSITION"
CAMPO DA INVENÇÃO FIELD OF INVENTION
[001] A presente invenção refere-se a uma mistura emulsificante para uso em composição aerossol, bem como a uma composição aerossol que apresenta baixa viscosidade e excelente estabilidade.  The present invention relates to an emulsifying mixture for use in aerosol composition as well as an aerosol composition having low viscosity and excellent stability.
FUNDAMENTOS DA INVENÇÃO BACKGROUND OF THE INVENTION
[002] Emulsões são definidas como um sistema heterogéneo de pelo menos dois líquidos imiscíveis, sendo um chamado de fase contínua e o outro de fase dispersa. A fase dispersa (interna) encontra-se distribuída em forma de gotí cuias na fase contínua (externa). De forma geral, o sistema precisa de agentes emulsionantes para se estabilizar. Estes agentes possuem duas funções básicas: a primeira é diminuir a tensão interfacial favorecendo a formação da emulsão e a segunda é evitar a coalescência da fase dispersa.  Emulsions are defined as a heterogeneous system of at least two immiscible liquids, one called a continuous phase and the other a dispersed phase. The dispersed (internal) phase is distributed as droplets in the continuous (external) phase. In general, the system needs emulsifying agents to stabilize. These agents have two basic functions: the first is to decrease interfacial tension by favoring emulsion formation and the second is to avoid dispersion phase coalescence.
[003] Dependendo da proporção volumétrica relativa entre as duas fases, as emulsões podem ser água-em-óleo (A/O) ou óleo-em-água (O/A). Nas emulsões água-em-óleo (A/O), a água encontra-se dispersa no óleo que atua como fase externa. Por outro lado, nas emulsões óleo-em-água (O/A), o óleo constitui a fase dispersa e a água, a fase contínua. Depending on the relative volumetric ratio between the two phases, the emulsions may be water-in-oil (A / O) or oil-in-water (O / A). In water-in-oil (W / O) emulsions, water is dispersed in the oil which acts as an external phase. In oil-in-water (O / W) emulsions, on the other hand, oil is the dispersed phase and water is the continuous phase.
[004] A tensão superficial ou interfacial pode ser definida como a força por unidade de comprimento que impede o rompimento da superfície de contato entre as duas fases. Quando a força é aplicada na interface entre um líquido e um gás, denomina-se de tensão superficial, que é dependente da temperatura e da concentração dos componentes na interface. Usualmente, a tensão superficial decresce quando a temperatura aumenta com exceção de alguns metais líquidos.  [004] Surface or interfacial tension can be defined as the force per unit length that prevents contact surface breakage between the two phases. When force is applied at the interface between a liquid and a gas, it is called surface tension, which is dependent on the temperature and concentration of the components at the interface. Usually, the surface tension decreases when the temperature increases except for some liquid metals.
[005] As emulsões apresentam uma tendência natural para separar-se em suas duas fases constitutivas, diminuindo a área interfacial e, consequentemente, a energia interfacial. Uma emulsão é considerada estável quando pequena ou nenhuma mudança ocorre no tamanho de gota da fase dispersa em um determinado intervalo de tempo [005] Emulsions have a natural tendency to separate into their two constitutive phases, decreasing the interfacial area and hence the interfacial energy. An emulsion is considered stable when little or no change occurs in phase droplet size. disperses over a certain time interval
[006] Um emulsificante é uma substância composta de moléculas com regiões tanto hidrofílicas (polares, afins à água) quanto lipofílicas (não polares, afins aos óleos). Sua ação é resultado da natureza de suas moléculas.  [006] An emulsifier is a substance composed of molecules with both hydrophilic (polar, water-like) and lipophilic (non-polar, oil-like) regions. Its action is a result of the nature of its molecules.
[007] Dentro de um sistema heterogéneo de duas substâncias imiscíveis de polaridades diferentes, o emulsificante coloca-se na interface da mistura. Em relação à orientação das moléculas do emulsificante, a parte hidrofílica (cabeça) orienta-se na direção da fase polar do sistema, enquanto a parte lipofílica (cauda) orienta-se em direção da fase não polar. No primeiro caso, quando a fase contínua é uma substância não polar (oleosa), as moléculas de emulsificante são formadas com a parte hidrofílica posicionada para dentro da fase dispersa. No segundo caso, quando a fase contínua é uma substância polar (aquosa), as moléculas de emulsificante posicionam-se de forma inversa, com a parte hidrofílica para fora da fase dispersa. Within a heterogeneous system of two immiscible substances of different polarities, the emulsifier is placed at the interface of the mixture. Regarding the orientation of the emulsifier molecules, the hydrophilic (head) part is oriented towards the polar phase of the system, while the lipophilic (tail) part is oriented towards the non-polar phase. In the first case, when the continuous phase is a nonpolar (oily) substance, the emulsifier molecules are formed with the hydrophilic part positioned into the dispersed phase. In the second case, when the continuous phase is a polar (aqueous) substance, the emulsifier molecules are reversed with the hydrophilic part out of the dispersed phase.
[008] O estado da técnica apresenta diversas opções de emulsificantes que auxiliam na estabilidade de emulsões de composições aerossóis. The state of the art presents several emulsifier options which aid in emulsion stability of aerosol compositions.
[009] O documento patentário brasileiro PI 9610904-1 revela uma composição inseticida na forma de emulsão água-em-óleo aerossol compreendendo emulsificantes em uma quantidade de 0,2 a 10% em peso selecionados do grupo compreendendo ésteres de mono-, di- e tri-sorbitano, ésteres de sorbitano polioxietileno e ésteres de mono e poliglicerol.  Brazilian patent document PI 9610904-1 discloses an insecticidal composition in the form of an aerosol water-in-oil emulsion comprising emulsifiers in an amount of 0.2 to 10% by weight selected from the group comprising mono-, di- and tri-sorbitan, polyoxyethylene sorbitan esters and mono and polyglycerol esters.
[0010] O documento de patente PI 0818368-6 descreve composição em aerossol compreendendo: 0,01% a 1 ,00% em peso de borato de sódio; 0,01% a 1,50% em peso de tensoativo de poliglicerol éster; até 30% em peso de propelente; e 67,5% a 85,0% em peso de água. Métodos de fabricação de um aromatizante de ar em aerossol também são descritos, em que a composição em aerossol ainda compreende uma fragrância. Patent PI 0818368-6 describes aerosol composition comprising: 0.01% to 1.00% by weight sodium borate; 0.01% to 1.50% by weight of polyglycerol ester surfactant; up to 30% by weight of propellant; and 67.5% to 85.0% by weight of water. Methods of making an aerosol air flavorant are also described, wherein the aerosol composition still comprises a fragrance.
[0011] O documento WO2012/089184 se refere a um sistema carreador coloidal na forma de nanocápsula, em que o sistema é útil para prevenir o envelhecimento da pele, compreendendo um núcleo de lipídeo e concha, em que o núcleo contém uma membrana de formação, um agente de emulsificação aniônico natural e um co-emulsificante não iônico natural de cadeia simples. WO2012 / 089184 refers to a system A nanocapsule colloidal carrier, wherein the system is useful for preventing skin aging, comprising a lipid and shell nucleus, wherein the core contains a forming membrane, a natural anionic emulsifying agent and a non-co-emulsifier. single chain natural ionic.
[0012] Entretanto, nenhuma dessas alternativas possui, simultaneamente, características de baixa viscosidade e excelente estabilidade em emulsões. A presente invenção fornece uma solução para este problema técnico, fornecendo uma mistura emulsificante sinérgica.  However, none of these alternatives have both low viscosity characteristics and excellent emulsion stability. The present invention provides a solution to this technical problem by providing a synergistic emulsifier mixture.
SUMÁRIO DA INVENÇÃO SUMMARY OF THE INVENTION
[0013] De um modo amplo, a invenção descreve uma mistura emulsificante e uma composição aerossol preparada a partir de uma emulsão e da mistura emulsificante.  Broadly, the invention describes an emulsifier mixture and an aerosol composition prepared from an emulsion and emulsifier mixture.
[0014] A referida composição aerossol apresenta a vantagem de apresentar baixa viscosidade e excelente estabilidade de emulsão, tornando, assim, desnecessário agitar o produto aerossol antes de sua aplicação.  Said aerosol composition has the advantage of low viscosity and excellent emulsion stability, thus making it unnecessary to agitate the aerosol product prior to its application.
[0015] A referida composição aerossol também pode receber a adição de fragrâncias ou ativos durante a linha de envase, sem comprometer a sua estabilidade. Said aerosol composition may also receive the addition of fragrances or actives during the filling line, without compromising its stability.
DESCRIÇÃO DETALHADA DA INVENÇÃO  DETAILED DESCRIPTION OF THE INVENTION
[0016] A presente invenção refere-se a uma mistura emulsificante para ser usada em emulsões água-em-óleo em composições aerossol com baixa viscosidade e excelente estabilidade.  The present invention relates to an emulsifier mixture for use in water-in-oil emulsions in aerosol compositions with low viscosity and excellent stability.
[0017] Mais especificamente, a mistura emulsificante compreende óleo mineral e um éster de poliglicerol empregado na presente invenção é, preferencialmente, um oleato de tetraglicerina e suas variações.  More specifically, the emulsifier mixture comprising mineral oil and a polyglycerol ester employed in the present invention is preferably a tetraglycerin oleate and variations thereof.
[0018] Em um modo preferido, o óleo mineral está presente na mistura em uma faixa que varia entre 5 e 20% em peso e o éster de poliglicerol está presente em uma faixa que varia entre 95 e 80% em peso da mistura emulsificante. Preferably, the mineral oil is present in the mixture in a range ranging from 5 to 20% by weight and the polyglycerol ester is present in a range ranging from 95 to 80% by weight. emulsifying mixture.
[0019] Preferencialmente, óleo mineral está presente em uma faixa que varia entre 5 e 10% em peso e o éster de poliglicerol está presente em uma faixa que varia entre 95 e 90% em peso da mistura emulsificante.  Preferably, mineral oil is present in a range ranging from 5 to 10% by weight and the polyglycerol ester is present in a range ranging from 95 to 90% by weight of the emulsifier mixture.
[0020] A composição aerossol preparada de acordo com a presente invenção compreende a mistura emulsificante, um solvente de origem fóssil e água. Adicionalmente, a composição aerossol compreende uma fragrância, até 10% em peso da composição, e um composto anti-corrosivo. The aerosol composition prepared according to the present invention comprises the emulsifier mixture, a solvent of fossil origin and water. Additionally, the aerosol composition comprises a fragrance, up to 10% by weight of the composition, and an anti-corrosive compound.
[0021] Especificamente, o solvente é um solvente de origem fóssil e a fragrância está presente ou não na composição aerossol, assim como outros materiais coadjuvantes a composição final do produto. Specifically, the solvent is a solvent of fossil origin and the fragrance is present or not in the aerosol composition, as well as other supporting materials in the final composition of the product.
[0022] O composto anti-corrosivo é, preferencialmente, o benzoato de sódio, presente em uma faixa entre 0,02 e 0,1% em peso da composição. The anti-corrosive compound is preferably sodium benzoate, present in a range between 0.02 and 0.1% by weight of the composition.
[0023] A composição aerossol preparada a partir da mistura emulsificante da presente invenção, apresenta viscosidade abaixo de 5000 mPa.s, e excelente estabilidade em emulsões água-em-óleo e um pH a 25°C variando dentre 6 a 8. The aerosol composition prepared from the emulsifier mixture of the present invention has a viscosity below 5000 mPa.s, and excellent stability in water-in-oil emulsions and a pH at 25 ° C ranging from 6 to 8.
[0024] Além disso, a composição aerossol da presente invenção apresenta a vantagem de ser pronta para o uso, ou seja, não há a necessidade de se agitar o produto antes de aplicá-lo, podendo ser utilizada em diversos produtos aerossóis, como odorizadores e desodorizadores de ambientes, inseticidas, lustra móveis e produtos domésticos e institucionais destinados a limpeza em geral.  Furthermore, the aerosol composition of the present invention has the advantage of being ready for use, ie there is no need to agitate the product before applying it and can be used in various aerosol products such as odorants. and room deodorizers, insecticides, polishes furniture and household and institutional products intended for general cleaning.

Claims

REIVINDICAÇÕES
1. Mistura emulsificante, caracterizada pelo fato de compreender um éster de poliglicerol e um óleo mineral, em que o óleo mineral está presente na mistura em uma faixa de 5 a 20% em peso e o éster de poliglicerol está presente em uma faixa de 95 a 80% em peso.  Emulsifying mixture, comprising a polyglycerol ester and a mineral oil, wherein the mineral oil is present in the mixture in a range of 5 to 20% by weight and the polyglycerol ester is present in a range of 95%. 80% by weight.
2. Mistura emulsificante de acordo com a reivindicação 1, caracterizada pelo fato de o óleo mineral estar presente em uma faixa que varia entre 5 e 10% em peso e o éster de poliglicerol está presente em uma faixa que varia entre 95 e 90% em peso da mistura emulsificante.  Emulsifying mixture according to claim 1, characterized in that the mineral oil is present in a range ranging from 5 to 10% by weight and the polyglycerol ester is present in a range ranging from 95 to 90% by weight. weight of emulsifier mixture.
3. Mistura emulsificante de acordo com a reivindicação 1 ou 2, caracterizada pelo fato de que o éster de poliglicerol é o oleato de tetraglicerina e suas variações.  Emulsifying mixture according to claim 1 or 2, characterized in that the polyglycerol ester is tetraglycerin oleate and its variations.
4. Mistura emulsificante de acordo com qualquer uma das reivindicações 1 a 3, caracterizada pelo fato de ser útil em emulsões água-em- óleo.  Emulsifying mixture according to any one of Claims 1 to 3, characterized in that it is useful in water-in-oil emulsions.
5. Composição aerossol, caracterizada pelo fato de que compreende a mistura emulsificante como definida em qualquer uma das reivindicações 1 a 4, e um solvente.  Aerosol composition, characterized in that it comprises the emulsifying mixture as defined in any one of claims 1 to 4, and a solvent.
6. Composição aerossol de acordo com a reivindicação 5, caracterizada pelo fato de que o solvente é um solvente de origem fóssil.  Aerosol composition according to claim 5, characterized in that the solvent is a solvent of fossil origin.
7. Composição aerossol de acordo com a reivindicação 5 ou 6, caracterizada pelo fato de que compreende adicionalmente uma fragrância que pode ser adicionada no momento do envase do propelente no aerossol, um anti-corrosivo, assim como outros materiais coadjuvantes a composição final do produto e água.  Aerosol composition according to Claim 5 or 6, characterized in that it further comprises a fragrance which may be added at the time of aerosol propellant filling, an anti-corrosive as well as other supporting materials to the final product composition. and water.
8. Composição aerossol de acordo com a reivindicação 7, caracterizada pelo fato de que a fragrância está presente ou não na composição em uma proporção com a mistura emulsificante.  Aerosol composition according to claim 7, characterized in that the fragrance is present or not in the composition in proportion to the emulsifier mixture.
9. Composição aerossol de acordo com a reivindicação 7, caracterizada pelo fato de que o anti-corrosivo é o benzoato de sódio, em que está presente em uma proporção entre 0,02 a 0,1% em peso da composição. Aerosol composition according to claim 7, characterized by the fact that the anti-corrosive is sodium benzoate, where it is present in a ratio between 0.02 to 0.1% by weight of the composition.
10. Composição aerossol de acordo com qualquer uma das reivindicações 5 a 9, caracterizada pelo fato de que a composição possui uma viscosidade a 25°C abaixo de 5000 mPa.s.  Aerosol composition according to any one of claims 5 to 9, characterized in that the composition has a viscosity at 25 ° C below 5000 mPa.s.
11. Composição aerossol de acordo com qualquer uma das reivindicações 5 a 10, caracterizada pelo fato de que a composição possui um pH a 25 °C variando dentre 6 a 8.  Aerosol composition according to any one of claims 5 to 10, characterized in that the composition has a pH at 25 ° C ranging from 6 to 8.
12. Composição aerossol, caracterizada pelo fato de ser utilizada em produtos aerossóis, como odorizadores e desodorizadores de ambientes, inseticidas, lustra móveis e produtos domésticos e institucionais destinados a limpeza em geral.  12. Aerosol composition, characterized in that it is used in aerosol products, such as room odorizers and deodorizers, insecticides, furniture polishes and household and institutional products intended for general cleaning.
PCT/BR2018/050042 2017-03-02 2018-02-23 Emulsifying mixture and aerosol composition WO2018157221A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB680220A (en) * 1949-07-27 1952-10-01 Schou Herbert Improvements in hydrocarbon oil emulsions
US5397497A (en) * 1992-08-07 1995-03-14 Solvay Fluor Und Derivate Gmbh Bath additive composition containing polyglycerol fatty acid ester mixture
US5466719A (en) * 1992-08-07 1995-11-14 Solvay Fluor Und Derivate Gmbh Polyglycerol fatty acid ester mixture
BRPI0609976A2 (en) * 2005-04-04 2011-10-11 Valent Biosciences Corp pesticide concentrate, ready-to-use product, method of using the product, and process for producing a pesticide concentrate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB680220A (en) * 1949-07-27 1952-10-01 Schou Herbert Improvements in hydrocarbon oil emulsions
US5397497A (en) * 1992-08-07 1995-03-14 Solvay Fluor Und Derivate Gmbh Bath additive composition containing polyglycerol fatty acid ester mixture
US5466719A (en) * 1992-08-07 1995-11-14 Solvay Fluor Und Derivate Gmbh Polyglycerol fatty acid ester mixture
BRPI0609976A2 (en) * 2005-04-04 2011-10-11 Valent Biosciences Corp pesticide concentrate, ready-to-use product, method of using the product, and process for producing a pesticide concentrate

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