EP1144102B1 - Lösungen oder konzentrierte und lösbare dispersionen und verfahren zu ihrer herstellung - Google Patents

Lösungen oder konzentrierte und lösbare dispersionen und verfahren zu ihrer herstellung Download PDF

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Publication number
EP1144102B1
EP1144102B1 EP00900621A EP00900621A EP1144102B1 EP 1144102 B1 EP1144102 B1 EP 1144102B1 EP 00900621 A EP00900621 A EP 00900621A EP 00900621 A EP00900621 A EP 00900621A EP 1144102 B1 EP1144102 B1 EP 1144102B1
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EP
European Patent Office
Prior art keywords
glycol
ether
composition
active agent
weight
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.)
Expired - Lifetime
Application number
EP00900621A
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English (en)
French (fr)
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EP1144102A1 (de
Inventor
Jean-Marc Angeli
Alfred Testa
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.)
Arcane Industries SAS
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Arcane Industries SAS
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Filing date
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Application filed by Arcane Industries SAS filed Critical Arcane Industries SAS
Publication of EP1144102A1 publication Critical patent/EP1144102A1/de
Application granted granted Critical
Publication of EP1144102B1 publication Critical patent/EP1144102B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0017—Multi-phase liquid compositions
    • C11D17/0021—Aqueous microemulsions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents

Definitions

  • the present invention relates to new solutions or concentrated and dilutable dispersions, their preparation process and their applications.
  • liquid active agents in various fields are effective but cannot be used as is. Indeed, given their pure effectiveness too high, they should be used diluted, for example under form of emulsions for a liquid active agent. But then the problem arises of their recovery and reprocessing, especially if they have harmful effects for the environment.
  • a conventional micro-emulsion of terpene solvent with the typical composition next: water / polyoxethylenated fatty alcohols / polyoxethylenated nonylphenols / sodium xylene sulfonate / isopropanol / terpene solvent. Its lifespan is limited, as well as its temperature resistance. It cannot therefore be used than cold.
  • microemulsions are obtained by gradually adding with stirring an aqueous phase in a phase organic (or vice versa), in the presence of a surfactant, and if necessary a third solvent.
  • Microemulsions are homogeneous compositions but they include significant concentrations of formulants, including emulsifiers and hydrotropic agents.
  • WO-A-91/00893 describes paint and varnish removers containing possibly water and in the form of gels or carriers impregnated on organic clays such as bentones. These compositions involve at least 10% of a third water-soluble solvent of N-methyl type pyrrolidone.
  • compositions in the form of solutions or dispersions of concentrated microemulsion type or of a hydrophobic active agent or of an N-alkyl pyrrolidone with water meeting the above criteria could be obtained simply, by the use alone of a mixture of two glycol ethers.
  • hydrophobic is meant that the active agent has a solubility in weak water.
  • the water solubility of the active ingredient (s) will be preferably less than or equal to 8%, in particular less than or equal to 6%, particularly less than or equal to 4%, very particularly less than or equal to 1%.
  • composition When the composition is a microemulsion, it is for example water in oil (W / O), in particular “multiple” (O / W / O or W / O / W), and particularly oil in water (O / W).
  • the glycol ethers may represent for example 50% to 90% by weight of the concentrated microemulsion, in particular 60% to 90%, and especially 70% to 90%.
  • the first report glycol ether to the second glycol ether may for example range from 1: 8 to 4: 5, in particular from 1: 5 to 3: 5, and very particularly from 1: 3 to 2: 5 by weight.
  • the active agent with a higher KB index or equal to 30 and in particular to 40 will be chosen from fatty substances, derivatives terpenics of synthetic, hemisynthetic or natural origin, rectified or no (by distillation) like pine essential oils, terpenes citrus, especially orange such as d-limonene, solvents non-water-soluble organic aliphatic petroleum products, the isoparaffinic, certain carboxylated derivatives, such as esters such as dimethylesters, certain amides, carbonyl derivatives such as certain ketones, certain aldehydes, other polar solvents such as alcohols terpenics, fatty alcohols (therefore high molecular weight), thiols, certain amines, and ethers comprising for example from 4 to 15 atoms of carbon, preferably from 5 to 14 carbon atoms, especially from 7 to 13 carbon atoms.
  • the active agent will preferably be chosen from terpenes citrus, especially orange; d-limonene is particularly retained.
  • the active agent will especially be d-limonene, a mixture of RPDE dimethylesters or a mixture thereof.
  • an active agent used in cosmetics such as a moisturizing agent such as evening primrose oil, a soothing and healing agent like allantoin, an anti UV agent like phenoxyethanol or mexoryl®, an anti-aging agent such as retinol, retinaldehyde, vitamin A acid, an exfoliating agent, an antioxidant agent or an active agent pharmaceutical used in dermatology as a corticosteroid.
  • a moisturizing agent such as evening primrose oil
  • a soothing and healing agent like allantoin such as phenoxyethanol or mexoryl®
  • an anti-aging agent such as retinol, retinaldehyde, vitamin A acid, an exfoliating agent, an antioxidant agent or an active agent pharmaceutical used in dermatology as a corticosteroid.
  • the N-alkyl pyrrolidone is preferably N-methyl pyrrolidone.
  • microemulsions or solutions may further include one or more conventional additives chosen for example from additives soluble in a non-aqueous phase such as perfumes, and preservatives like formalin or parabens. These can be used in the usual proportions in the case of microemulsions, in particular less than 5%, particularly from 0.1% to 3%, and most particularly from 0.1% at 2% by weight.
  • the additive could also be a preparation based on unsaturated fatty acid dimethylamides such as that sold under the denomination DMAD or BUSPERSE® 47 by the company BUCKMAN.
  • microemulsions or solutions allows to give them special properties such as biocidal properties. They can be made completely water-soluble by adding surfactants emulsifying like those marketed by RHODIA under the name Rhodoclean HP and / or ASP (alkoxylated fatty alcohols, derivatives pine terpenes) and Rhodasurf T-50 (ethoxylated fatty alcohol) or using a ether amine oxide.
  • surfactants emulsifying like those marketed by RHODIA under the name Rhodoclean HP and / or ASP (alkoxylated fatty alcohols, derivatives pine terpenes) and Rhodasurf T-50 (ethoxylated fatty alcohol) or using a ether amine oxide.
  • the present application also relates to a microemulsion or above concentrated solution characterized in that it is diluted so that the diluent phase such as an isoparaffinic solvent and in particular a phase aqueous represents up to 99% by weight of the microemulsion or solution diluted, especially up to 80%, preferably up to 60%, particularly up to 50%, especially up to 40%.
  • the diluent phase such as an isoparaffinic solvent
  • a phase aqueous represents up to 99% by weight of the microemulsion or solution diluted, especially up to 80%, preferably up to 60%, particularly up to 50%, especially up to 40%.
  • the present application also relates to a method of preparation of a microemulsion or concentrated solution above, characterized in that the liquid active agent is mixed with stirring and glycol ethers to emulsify or dissolve it in these last.
  • liquid active agents can also be used.
  • a non-liquid active agent should be melted or dissolved beforehand to pass into liquid form.
  • the diluent is in particular water or an aqueous phase. It is also in particular an isoparaffinic solvent. It can also be a solvent non-water soluble aromatic organic like petroleum solvents like white spirits.
  • a microemulsion or dilute solution can also be prepared by diluting a microemulsion or concentrated solution above.
  • the glycol ethers may be represented by example 15% to 85% by weight of the diluted microemulsion, in particular 20% to 80%, particularly 25% to 70%, and especially 30% to 50%.
  • the aqueous phase is preferably consisting of demineralized water in particular.
  • the aqueous phase preferably further comprises an agent softener such as a phosphonate or the tetrasodium salt of ethylene acid tetraacetic diamine.
  • an agent softener such as a phosphonate or the tetrasodium salt of ethylene acid tetraacetic diamine.
  • the softening agent may represent around 0.5% by weight of composition.
  • the aqueous phase can also contain, if desired, one or more water-soluble compounds such as dyes.
  • compositions of the invention also have a high water rinsability, in particular active agents which are not by nature, and / or a possibility of aqueous dilution and separation of phases adjustable at will and predetermined.
  • microemulsions or solutions according to the invention are easily recyclable. After use, a simple aqueous dilution can reduce the volume of non-aqueous effluents to be treated.
  • the used solution or microemulsion quickly separates into two very distinct phases, one of which is not aqueous. During phase separation, the glycol ethers are distribute within each phase to facilitate transfer and solubilization respective impurities and contribute to the clarity of the interface.
  • the system according to the invention has total reversibility.
  • the non-aqueous phase may be filtered and / or rectified for recycling.
  • the simple addition of propylene glycol methyl ether and water will allow recreate the original product.
  • This recycling can be repeated several times
  • glycol ethers according to the invention, it is possible to obtain, even with the same composition of the rest of the formula, microemulsions active agents of a chemical nature and polarity as different as d-limonene and mixtures of dimethylesters.
  • microemulsions of the invention make it possible to produce a excellent surface preparation of mechanical parts before mounting or application of a protective coating. They can be used on most metals, alloys, plastics and elastomers, especially for exterior maintenance of aircraft.
  • compositions which have a excellent chemical harmlessness to sensitive seals and materials (polycarbonates, EPDM). They leave a non-surface finish after use greasy, without impurity or residual film.
  • microemulsions or solutions of the invention as industrial solvent, cleaner - renovator or surface treatment for plastics such as furniture garden, as a cleaner - restorer for stained or blackened wood, as a cleaner for polyurethane foams. They also justify the use of microemulsions or solutions of the invention for removing putty residues, clean brushes, remove glues and adhesives and dilute all paintings. They still find their use in boating (washing of wood, plastics, mechanical elements, ...) especially as they are rinsable with sea water unlike detergents, or even for those involving an N-alkyl pyrrolidone, in the pickling.
  • the invention also relates to washing agents. or pickling which comprise a diluted microemulsion of the invention or microemulsion or concentrated solution defined above.
  • Diluted microemulsions corresponding to the formula were prepared: Content in% Weight / Weight Ex. 1 Ex. 2 Ex 3 Demineralized Water qs 100% qs 100% qs 100% Dipropylene glycol methyl ether 25.0% 80.0% 85.0% Propylene glycol n-butyl ether 0 0 0 d-limonene 0 2 to 10% 10% Mixture of RPDE dimethylesters 2 to 10% 0 0 0
  • Diluted microemulsions corresponding to the formula were prepared: Content in% Weight / Weight Ex. 4 Ex. 5 Ex 6 Demineralized Water qs 100% qs 100% qs 100% Dipropylene glycol methyl ether 27.0% 26.0% 45.0% Propylene glycol n-butyl ether 10.0% 5 to 15% 25.0% d-limonene 0 0 10% Mixture of RPDE dimethylesters 2 to 20% 15.0% 0
  • microemulsions were prepared in the following manner:
  • composition containing 27% of ether dipropylene glycol methyl and 10% propylene glycol n-butyl ether allow to emulsify from 2% to 20% of mixture of RPDE dimethylesters without having to make a formula adjustment other than water qs 100% in weight.
  • microemulsions were prepared by mixing in 5 minutes, until the mixture is clear, the methyl ether of dipropylene glycol and the n-butyl ether of propylene glycol, then, while maintaining stirring constant, the mixture of RPDE dimethylesters. We still stir for 5 minutes and ensuring the homogeneity of the microemulsion.
  • Example 5 After diluting 1/1 of Example 7 with water, we obtain if desired the microemulsion diluted in Example 5 with 11.0% n-butyl ether of propylene glycol.
  • microemulsion of Example 8 is dilutable in all proportions, especially in water.
  • dilute microemulsions corresponding to the formula were prepared: Content in% Weight / Weight Ex. 9 Ex.10 Ex.11 Ex. 12 Demineralized Water 53.0% 10.0% 49.0% 20.0% Dipropylene glycol methyl ether 27.0% 80.0% 26.0% 45.0% Propylene glycol n-butyl ether 10.0. % - 10.0% 25.0% d-limonene - 10.0% - 10.0% Mixture of RPDE dimethylesters 10.0% - 15.0% - Water 34.0% 6.0% 12.0% 10.0%
  • the last line of the table represents the quantity of phase aqueous, for example water, from which a release of the organic phase, as well as the capacity of microemulsions to absorb by example of water, i.e. to be diluted.
  • Example 10 does not part of the invention.
  • Example 6 100 g of the microemulsion original (representing 100% by weight) which was then used to degreasing of automotive mechanical parts, when 40 mL is added of water to the micro-emulsion of soiled origin, stir and then allow to stand, we observe the appearance of a disorder, witnessing the loss of homogeneity of the composition, then we observe a phase shift in two clear superimposed phases with a very clear separation at the interface.
  • the hydrophilic phase represents 92 mL for 65.3 mL at the start. Since 40 mL of water was added, we have recovered approximately 80% of the hydrophilic starting phase.
  • compositions of the invention therefore make it possible to only have to treat a reduced volume of liquid.
  • dilute microemulsions corresponding to the formula were prepared: Content in% Weight / Weight Ex. 14 Ex. 15 Ex. 16 Ex. 17 Ex. 18 Demineralized Water 20.0% 25.0% 62.5% 20% 67.5% Dipropylene glycol methyl ether 45.0% 37.5% 20.0% 40.0% 15.0% Propylene glycol n-propyl ether 25.0% 27.5% - - 7.5% Npropylene dipropylene glycol ether - - 7.5% 30 % - d-limonene 10.0% - 10.0% - Mixture of RPDE dimethylesters - 10.0% - 10.0%
  • This example 14 shows that thanks to the use of glycol ethers according to the invention, a microemulsion of active agents of a natural nature is obtained chemical and polarity as different as d-limonene and mixtures of dimethyl esters.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Colloid Chemistry (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)

Claims (10)

  1. Zusammensetzung in Form einer Wirkstoff-flüssig-flüssig-Dispersion vom Typ Mikroemulsion oder Lösung, die konzentriert und in Wasser oder einer wässerigen Phase oder einem Isoparaffin-Lösungsmittel oder einem in Wasser unlöslichen aromatischen organischen Lösungsmittel verdünnbar ist, wobei die Zusammensetzung klar wie Wasser und zu mindestens 90 Gew.%
    aus mindestens 10 Gew.% eines hydrophoben Wirkstoffs mit einem Kauri-Butanol-Index von mindestens 30 oder aus weniger als 10 % und mehr als 0 % eines N-Alkylpyrrolidons und
    einer Mischung von zwei Glycolethern gebildet ist, wobei der erste Glycolether einen HLB-Wert von über 0,8 über jenem des zweiten Glycolethers aufweist.
  2. Konzentrierte Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass der Wirkstoff ein hydrophober Wirkstoff mit einem Kauri-Butanol-Index von mindestens 40 ist.
  3. Konzentrierte Zusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass sie zu mindestens 95 %
    aus mindestens 10 Gew.% eines hydrophoben Wirkstoffs mit einem Kauri-Butanol-Index von mindestens 30 oder aus weniger als 10 % und mehr als 0 % eines N-Alkylpyrrolidons und
    einer Mischung von zwei Glycolethern gebildet ist, wobei der erste Glycolether einen HLB-Wert von über 0,8 über jenem des zweiten Glycolethers aufweist.
  4. Konzentrierte Zusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass sie in Form einer Mikroemulsion vorliegt.
  5. Konzentrierte Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie als Glycolether Dipropylenglycolmethylether enthält.
  6. Konzentrierte Zusammensetzung nach Anspruch 5, dadurch gekennzeichnet, dass sie als zweiten Glycolether Propylen-n-propylether, Dipropylenglycol-n-propylether oder Propylenglycol-nbutylether enthält.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie 50 bis 90 Gew.% Ether oder Glycolether enthält.
  8. Zusammensetzung nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie derart verdünnt ist, dass die Verdünnungsphase bis zu 99 Gew.% der Mikroemulsion oder verdünnten Lösung ausmacht.
  9. Verfahren zur Herstellung einer konzentrierten Zusammensetzung nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass der flüssige Wirkstoff und die Glycolether unter Rühren gemischt werden, so dass dieser in letzteren emulgiert oder gelöst wird.
  10. Wasch- oder Beizmittel, welches eine konzentrierte oder verdünnte Zusammensetzung nach einem der Ansprüche 1 bis 8 umfasst.
EP00900621A 1999-01-21 2000-01-20 Lösungen oder konzentrierte und lösbare dispersionen und verfahren zu ihrer herstellung Expired - Lifetime EP1144102B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9900793 1999-01-21
FR9900793A FR2788703B1 (fr) 1999-01-21 1999-01-21 Micro-emulsions ou solutions concentrees et diluables, procede de preparation et applications
PCT/FR2000/000118 WO2000043117A1 (fr) 1999-01-21 2000-01-20 Solutions ou dispersions concentrees et diluables, procede de preparation et applications

Publications (2)

Publication Number Publication Date
EP1144102A1 EP1144102A1 (de) 2001-10-17
EP1144102B1 true EP1144102B1 (de) 2004-04-07

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Application Number Title Priority Date Filing Date
EP00900621A Expired - Lifetime EP1144102B1 (de) 1999-01-21 2000-01-20 Lösungen oder konzentrierte und lösbare dispersionen und verfahren zu ihrer herstellung

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EP (1) EP1144102B1 (de)
AT (1) ATE263620T1 (de)
DE (1) DE60009657D1 (de)
FR (1) FR2788703B1 (de)
WO (1) WO2000043117A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2508572B1 (de) 2011-04-08 2014-06-25 Dow Global Technologies LLC Glykoletherester mit niedrigem Gehalt an flüchtigen organischen Verbindungen bzw. frei davon als Reinigungslösungsmittel und Farbverdünner

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5098591A (en) * 1989-06-30 1992-03-24 Stevens Sciences Corp. Paint stripper and varnish remover compositions containing organoclay rheological additives, methods for making these compositions and methods for removing paint and other polymeric coatings from flexible and inflexible surfaces

Also Published As

Publication number Publication date
FR2788703B1 (fr) 2002-06-28
EP1144102A1 (de) 2001-10-17
DE60009657D1 (de) 2004-05-13
FR2788703A1 (fr) 2000-07-28
WO2000043117A1 (fr) 2000-07-27
ATE263620T1 (de) 2004-04-15

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