EP1268723B1 - Perlglanzkonzentrate - Google Patents

Perlglanzkonzentrate Download PDF

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Publication number
EP1268723B1
EP1268723B1 EP01929292A EP01929292A EP1268723B1 EP 1268723 B1 EP1268723 B1 EP 1268723B1 EP 01929292 A EP01929292 A EP 01929292A EP 01929292 A EP01929292 A EP 01929292A EP 1268723 B1 EP1268723 B1 EP 1268723B1
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EP
European Patent Office
Prior art keywords
oder
bis
anionic
surfactant
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
EP01929292A
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German (de)
English (en)
French (fr)
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EP1268723A1 (de
Inventor
Gerd H. Dahms
Klaus Kwetkat
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.)
Sasol Germany GmbH
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Sasol Germany GmbH
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Filing date
Publication date
Application filed by Sasol Germany GmbH filed Critical Sasol Germany GmbH
Publication of EP1268723A1 publication Critical patent/EP1268723A1/de
Application granted granted Critical
Publication of EP1268723B1 publication Critical patent/EP1268723B1/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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0089—Pearlescent compositions; Opacifying agents
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • 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
    • C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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

Definitions

  • the invention relates to aqueous, flowable pearlescent concentrates comprising one or more pearlescing components, gemini surfactants and at least one further surfactant.
  • Cosmetic hair and body cleansers, dishwashing detergents and liquid detergents and cleaners contain substances which give the formulations mentioned a pearlescent appearance in order to improve the visual appearance of wetted surfaces and thus to increase the commercial value.
  • substances for example finely powdered natural substances such as mica, fish-silver, inorganic materials such as bismuth oxychloride and titanium dioxide pigments, metal salts of higher fatty acids, fatty acid monoesters or diesters, fatty acid alkanolamides or long-chain fatty alcohols.
  • the only effect and task of pearlescent concentrate in the effect of giving the end product a pearl or silk gloss and this with a very easy to handle, so low viscosity, very stable and not adversely affecting the properties of the final product Pearly luster.
  • the pearlescent concentrate must not contain skin or mucous membrane irritating components.
  • active ingredients e.g. Vitamins, enzymes and proteins, which are often easy to reduce, oxidize or hydrolyze, are not possible here without special pre-treatment.
  • the present invention relates to surfactant compositions and the use of aqueous, flowable pearlescent concentrates according to claims 1 and 6.
  • the pearlescent concentrate is used in concentrations of particularly preferably 1.0 to 5% by weight in the end product.
  • the pearlescing component in the application formulation not only performs the function of imparting a pearl or silk luster of high optical density and brilliance to the end product, but also reduces the irritation potential of other anionic surfactants, leads to better foaming characteristics, the foam contains much surfactant solution and is very high creamy.
  • the pearlescent concentrate according to the invention leads to a good moisturizing effect of the application formulation and can be used as a vehicle for inclusion and thus protection of active components against oxidation, reduction or hydrolysis and for their controlled release (eg odorous substances only when used as intended).
  • the inventors have been determined, without wishing to be bound by theory, that unlike described in the literature (RL Crombie, SH Nicholson, Cons. Journal Com. Esp. Deterg., 28 (1998) 87-94), in the pearlescent effect compositions of the invention, the pearlescent components are not present in the form of small, oriented in the surfactant bilayers, crystals.
  • the pearlescent concentrate according to the invention forms elongated multilamellar liquid-crystalline layers.
  • the elongated multilamellar liquid-crystalline layers are composed of several surfactant bilayers. When stretched according to the invention, these stretched multilamellar layers also remain in the application formulation or at water concentrations typically found in formulations (1 to 90% by weight).
  • the elongated multilamellar liquid crystalline layers which form in compositions of the invention differ markedly from the concentric membrane vesicles described for encapsulating drugs (see, for example, WO 99/27907).
  • the arrangement of the elongated multilamellar liquid crystalline layers does not correspond to that of vesicles, but rather that of a system of emulsifier and co-emulsifier forming a gel network (J. Britto, Euro Cosmetics, 9 (1998) 27-32).
  • the shape of the elongated multilamellar liquid-crystalline layers is shown in FIG.
  • This is the pearlescent concentrate given in the examples as formulation (A).
  • the pearlescent concentrate was snap-frozen with liquid nitrogen, broken, the fracture surface was covered with conductive material and examined with the Scanning Electron Microscope (ESEM).
  • ESEM Scanning Electron Microscope
  • On display are the elongated multilamellar structures, which can be used for the inclusion of active substances. These differ markedly from the spherical, onion-like structures of conventional compositions, such as e.g. in WO 99/27907 are described.
  • active ingredients which themselves have an at least slightly amphoteric character, i. contain both hydrophobic and polar groups, which are incorporated as part of the bilayers. These active ingredients do not affect the efficiency of the pearlescing agent.
  • Oil-soluble active substances can be taken up by the elongated multilamellar liquid-crystalline layers and thus remain in front of them, e.g. Oxidation, reduction or hydrolysis protected.
  • Water soluble actives can be placed in the hydrous layers between the elongated multilamellar liquid crystalline layers.
  • the protective effect of the pearlescent concentrate can be determined simply by the concentration of the intact active substance over a certain period of time.
  • gemini surfactants are surface-active compounds which consist of at least two, preferably two, surfactant units, ie of hydrophilic head group and hydrophobic group, which are identified by at least one, preferably spacer, spacer Near the head group are linked together.
  • the gemini or gemini silk are also called dimer surfactants and bear their name because of their special design.
  • anionic, nonionic, cationic and amphoteric gemini surfactants there are anionic, nonionic, cationic and amphoteric gemini surfactants.
  • conventional surfactants which are likewise classified into these groups, gemini surfactants can also carry combinations of head groups of different character. These are usually combinations of nonionic and ionic groups.
  • the gemini surfactant has at least one anionic group.
  • gemini surfactants preferably used in the surfactant compositions according to the invention include those which contain nitrogen atoms at the point of attachment between spacer, hydrophilic and hydrophobic group. These include preferably gemini surfactants with spacers containing amines or amides, but also spacers deriving from dicarboxylic acids, hydrophilic double head groups derived from betaine structures which optionally have side groups prepared by alkoxylation (in particular ethoxylation), the sulfonic acid, phosphonic acid, carboxylic acid or alcohol groups (including polyhydric alcohols), and hydrophobic double chains of 5 to 25 carbon atoms, which may be branched or unbranched and may carry up to 2 non-contiguous double bonds.
  • gemini surfactants as represented by the formulas are particularly suitable for the surfactant compositions of the invention.
  • the preferred structural variants are explained in greater detail by the definition of the substituents / spacers, wherein each individual definition of a substituent / spacer can also characterize the gemini surfactant taken by itself.
  • the disclosure of the writings mentioned under AI to D.IV is hereby explicitly made the content of this application with regard to the definition of the gemini surfactants.
  • Variant A structures based on amide- or amine-containing spacers
  • Gemini surfactants of the general formula (A.III) are amphoteric compounds, so that they can also become cationic in a correspondingly acidic surrounding medium.
  • Variant B structures based on amide- or amine-containing spacers
  • Variant C structures based on amide- or amine-containing spacers
  • Mild in the sense of the invention means that the corresponding compounds / compositions are free of labeling (for example according to Directive 67-548-EEC, Hazardous Substances Ordinance) with respect to their irritation potential for skin and eyes.
  • the "poor foaming characteristic” property means that these surfactants, in their capacity as further detergent component, fall short of two of the three values listed below in the evaluation of their foaming behavior.
  • the "poor foaming characteristic” property means that these surfactants, in their capacity as further detergent components, fall short of two of the three values listed below in the evaluation of their foaming behavior.
  • the surfactant solution to be examined is 10 min. stirred at 1500 rev / min with apparatus with blade stirrer according to Figure 2/3 to 4/4, wherein the solution is slightly heated (from room temperature to about 35 ° C). After stirring for 10 minutes, the resulting foam is skimmed off from above and subjected to direct microscopy - in this case the lamella thickness is measured in mm and the number of foam bubbles in the image section is determined.
  • the foaming behavior of a surfactant under flowing cold tap water is also assessed.
  • 2 g of surfactant are distributed on the palm of your hand and rubbed evenly under running water.
  • Surfactants are judged to be good foaming if they have all three criteria with values of ⁇ 20 mm in the lamella thickness, ⁇ 20 bubbles in the image section (both directly after foaming) and a foaming behavior rated 3.
  • FIGS. 2 to 4 The method used for foam production is shown schematically in FIGS. 2 to 4.
  • the following experimental setup was chosen for all investigations in order to evaluate the influence of the surfactant mixtures on the foaming behavior:
  • alcohol ethoxylates having 6 to 13 carbon atoms and 4 to 15 moles of ethylene oxide, e.g. MARLIPAL® O13 / 120, Laureth-9 or MARLIPAL® 1012/6, and other nonionic surfactants with comparable HLB and a molecular weight ⁇ 800 g / mol.
  • the active substances according to the invention are substances which are particularly sensitive to reduction or oxidation, substances which are particularly sparingly soluble in water and oil or substances which are particularly sensitive to hydrolysis or surfactants.
  • Particularly suitable here are antioxidants, vitamins (especially tocopherol, retinol) and their derivatives, especially their esters, enzymes, proteins and pheromones.
  • substances which due to their acidity can cause problems in the formulation, such as ⁇ -hydroxy acids, are also suitable.
  • organic UV absorbers for example for perfuming or insect repellent, such as especially thiols, ternary or cyclic amines, natural essences whose insect repellent effect is known, for example citric or orange terpene, neem oil extract or insect repellent pheromones suitable for inclusion in the pearlescent concentrate.
  • odorous substances for example for perfuming or insect repellent, such as especially thiols, ternary or cyclic amines, natural essences whose insect repellent effect is known, for example citric or orange terpene, neem oil extract or insect repellent pheromones suitable for inclusion in the pearlescent concentrate.
  • odorous substances for example for perfuming or insect repellent, such as especially thiols, ternary or cyclic amines, natural essences whose insect repellent effect is known, for example citric or orange terpene, neem oil extract or insect repellent pheromones suitable for inclusion in
  • the combination gemini surfactant / poor foaming detergent component is dispensed with, it may be necessary in the case of insufficient stability of the active ingredients to add agents for stabilizing the lamellar layers (stabilizers) .
  • agents for stabilizing the lamellar layers are particularly suitable here.
  • Particularly suitable here are cholesterol and its derivatives as well as phytosterols and their derivatives as well as saturated or unsaturated fatty acids, in particular C 12 to C 22 fatty acids.
  • hydrophilic compounds can be used in both cases as a stabilizer, wherein said compounds additionally ensure better flowability of the compositions of the invention: glycerol or ethylene glycol or 1,2-propylene glycol, butylene glycol, hexylene glycol and / or polyethylene glycol having an average molecular weight of 80 bis 1,000 g / mol.
  • the pearlescent concentrates according to the invention can be prepared by mixing the components (A), (B), (C), (D) and (E) at 20 to 80 ° C, preferably at 40 to 50 ° C, and at 30 to 80 ° C, preferably at 40 to 50 ° C water is added.
  • the pearlescent effect sets in at 25 to 30 ° C and is stable at temperatures up to 60 ° C.
  • the finished pearlescent concentrate can be mixed with the application formulation at room temperature.
  • the temperature-dependent viscosity of the concentrates is determined to check the temperature stability of the concentrates.
  • Examples of pearlescent concentrates according to the invention are the following table compositions: [CTFA INCI] formulation A [weight%] B [weight%] PEG-3 stearates 10 10 Laureth-9 18 0 Isotrideceth-13 0 18 Sodium Lauroyl Lactylate, Sodium, Dicocoylethylenediamine PEG-15 sulfate (Geminitensid - Diamide ether sulfate) (CERALUTION® F) 10 10 PEG-400 8th 8th Aqua 54 54 [CTFA INCI] formulation C [weight%] D [% by weight] Glycol stearate 10 10 Laureth-9 18 0 Isotrideceth-13 0 18 Sodium Lauroyl Lactylate, Sodium Dicocoylethylenediamine PEG-15 sulfate (Gemini surfactant - Diamide Ether Sulfate) 10 10 PEG-400 8th 8th Aqua 54 54 [CTFA INCI] formulation E [% by weight] F [weight
  • compositions of the invention to effectively encapsulate active agents can be e.g. can be detected by the pH during storage of the formulation G and in each case the same amount of ascorbyl dipalmitate in water (see diagram 1/1).
  • the significant drop in pH indicates the hydrolysis of the ascorbyl dipalmitate. If this ester is encapsulated as in Formulation G, there is no significant hydrolysis.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
EP01929292A 2000-03-31 2001-04-02 Perlglanzkonzentrate Expired - Lifetime EP1268723B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10015992 2000-03-31
DE10015992A DE10015992A1 (de) 2000-03-31 2000-03-31 Perlglanzkonzentrate
PCT/DE2001/001246 WO2001074979A1 (de) 2000-03-31 2001-04-02 Perlglanzkonzentrate

Publications (2)

Publication Number Publication Date
EP1268723A1 EP1268723A1 (de) 2003-01-02
EP1268723B1 true EP1268723B1 (de) 2006-03-08

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Application Number Title Priority Date Filing Date
EP01929292A Expired - Lifetime EP1268723B1 (de) 2000-03-31 2001-04-02 Perlglanzkonzentrate

Country Status (11)

Country Link
US (1) US20040033913A1 (zh)
EP (1) EP1268723B1 (zh)
JP (1) JP2003529670A (zh)
CN (1) CN1277913C (zh)
AT (1) ATE319795T1 (zh)
AU (1) AU2001256131A1 (zh)
BR (1) BR0109591A (zh)
DE (2) DE10015992A1 (zh)
ES (1) ES2258526T3 (zh)
HK (1) HK1054049B (zh)
WO (1) WO2001074979A1 (zh)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2390247B (en) * 2002-06-28 2006-04-12 Dwight Cavendish Systems Ltd An improved method and apparatus for providing an anti-copy video signal
WO2004046300A1 (en) * 2002-11-14 2004-06-03 The Procter & Gamble Company Rinse aid containing encapsulated glasscare active salt
US8790668B2 (en) 2003-05-08 2014-07-29 The Procter & Gamble Company Personal care compositions that deposit shiny particles
US8147853B2 (en) 2005-02-15 2012-04-03 The Procter & Gamble Company Personal care compositions containing hydrophobically modified non-platelet particles
DE102005019431A1 (de) * 2005-04-25 2006-10-26 Eckart Gmbh & Co. Kg Pulverförmige Perlglanzzusammensetzung, Verfahren zu deren Herstellung und deren Verwendung
JP2006225369A (ja) * 2005-08-17 2006-08-31 Asahi Kasei Chemicals Corp パール状の洗浄剤
FR2905855B1 (fr) * 2006-09-15 2008-11-21 Oreal Composition cosmetique comprenant de l'acide ascorbique
US9555167B2 (en) * 2006-12-11 2017-01-31 3M Innovative Properties Company Biocompatible antimicrobial compositions
US20080200890A1 (en) * 2006-12-11 2008-08-21 3M Innovative Properties Company Antimicrobial disposable absorbent articles
US8580860B2 (en) * 2007-02-23 2013-11-12 Gojo Industries, Inc. Foamable alcoholic composition
ATE532847T1 (de) * 2007-03-20 2011-11-15 Procter & Gamble Verfahren zum reinigen von wäsche oder harten oberflächen
FR2956579B1 (fr) 2010-02-24 2012-02-10 Oreal Composition comprenant un polymere superabsorbant et tensioactif gemine
FR2989886B1 (fr) 2012-04-26 2016-12-09 Oreal Composition comprenant un silane et un tensioactif gemine
US9622951B2 (en) 2012-10-29 2017-04-18 The Procter & Gamble Company Personal care compositions

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57165308A (en) * 1981-04-03 1982-10-12 Lion Corp Production of pearlescent dispersion
JPS606693B2 (ja) * 1982-05-28 1985-02-20 花王株式会社 真珠光沢剤分散液の製造方法
US5540853A (en) * 1994-10-20 1996-07-30 The Procter & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
US5560873A (en) * 1994-12-30 1996-10-01 Chen; Pu Mild cold pearlizing concentrates
DE19616096A1 (de) * 1996-04-23 1997-11-06 Huels Chemische Werke Ag Verwendung von anionischen Geminitensiden in Formulierungen für Wasch-, Reinigungs- und Körperpflegemittel
DE19622612C1 (de) * 1996-06-05 1997-10-23 Henkel Kgaa Gemini-Tenside
DE19622968C2 (de) * 1996-06-07 2000-08-17 Cognis Deutschland Gmbh Wäßrige Perlglanzkonzentrate
EP0907702A1 (en) * 1996-06-28 1999-04-14 The Procter & Gamble Company Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants
WO1998000501A1 (en) * 1996-06-28 1998-01-08 The Procter & Gamble Company Detergent composition comprising dianionic cleaning agent and an enzyme
DE19646882C2 (de) * 1996-11-13 1998-09-24 Henkel Kgaa Wäßrige Perlglanzkonzentrate
US5863886A (en) * 1997-09-03 1999-01-26 Rhodia Inc. Nonionic gemini surfactants having multiple hydrophobic and hydrophilic sugar groups

Also Published As

Publication number Publication date
ES2258526T3 (es) 2006-09-01
BR0109591A (pt) 2003-02-04
HK1054049A1 (en) 2003-11-14
CN1277913C (zh) 2006-10-04
US20040033913A1 (en) 2004-02-19
WO2001074979A1 (de) 2001-10-11
HK1054049B (zh) 2007-04-27
DE10015992A1 (de) 2001-10-18
ATE319795T1 (de) 2006-03-15
JP2003529670A (ja) 2003-10-07
AU2001256131A1 (en) 2001-10-15
CN1419594A (zh) 2003-05-21
DE50109158D1 (de) 2006-05-04
EP1268723A1 (de) 2003-01-02

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