WO1998020850A1 - Verfahren zur herstellung einer fliessfähigen, wässrigen perlglanzdispersion mit fettsäure als perlglanzgebender komponente - Google Patents
Verfahren zur herstellung einer fliessfähigen, wässrigen perlglanzdispersion mit fettsäure als perlglanzgebender komponente Download PDFInfo
- Publication number
- WO1998020850A1 WO1998020850A1 PCT/EP1997/005930 EP9705930W WO9820850A1 WO 1998020850 A1 WO1998020850 A1 WO 1998020850A1 EP 9705930 W EP9705930 W EP 9705930W WO 9820850 A1 WO9820850 A1 WO 9820850A1
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- WIPO (PCT)
- Prior art keywords
- pearlescent
- fatty acid
- pearlescent dispersion
- dispersion according
- producing
- Prior art date
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- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940096362 cocoamphoacetate Drugs 0.000 description 1
- 229940047648 cocoamphodiacetate Drugs 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- WILVYLQMYNGFSH-UHFFFAOYSA-N ethanamine;n-ethylethanamine Chemical compound CCN.CCNCC WILVYLQMYNGFSH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940048098 sodium sarcosinate Drugs 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- C11D1/37—Mixtures of compounds all of which are anionic
-
- 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
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
-
- 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
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2079—Monocarboxylic acids-salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/596—Mixtures of surface active 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
- 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
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
-
- 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
- C11D1/126—Acylisethionates
-
- 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
Definitions
- This invention relates to a process for the production of a flowable or pumpable, aqueous pearlescent dispersion containing 5-30% of pearlescent components.
- Pearlescent dispersions are often incorporated to give surfactant formulations a better appearance and thus a higher commercial value. Examples include liquid detergents and cleaning agents (e.g. floor cleaners, dishwashing detergents) as well as liquid cosmetic preparations (e.g. personal care and body cleaning agents, shampoos, bath additives, etc.). Pearlescent dispersions give the formulations a silky or pearlescent appearance. The effect is caused by light scattering on the dispersed, mostly flake-shaped crystals of the pearlescent components.
- liquid detergents and cleaning agents e.g. floor cleaners, dishwashing detergents
- liquid cosmetic preparations e.g. personal care and body cleaning agents, shampoos, bath additives, etc.
- Pearlescent dispersions mainly consist of at least one pearlescent compound, at least one dispersant and water.
- Pearlescent compounds are, for example, fatty acid monoalkanoiamides, fatty acid dialkanolamides, monoesters or diesters of ethylene glycol or mixtures thereof, propylene glycol or its oligomers, mono- or diesters of alkylene glycols with fatty acids, fatty acids and their metal salts, monoesters or polyesters of glycerol with carboxylic acids and ketosulfones of various types.
- Pearlescent concentrates based on the pearlescent formers mentioned are known, for example, from DE-A-16 69 152, JP-56/71021 (Chem. Abstr. 95/156360), DE-A-34 11 328 and DE-A-35 10 081.
- the concentrates known from these publications contain fatty acid monoalkanoiamides or fatty acid dialkanolamides as part of the pearlescent substances.
- alkanolamides and their derivatives are suspected of being involved in the formation of nitrosamines. It is therefore desirable to formulate cosmetic preparations without such alkanolamides and alkanolamide derivatives.
- EP-0 449 904 discloses that in order to obtain a satisfactory pearlescence in the end product, significantly higher concentrations of pearlescent substances have to be used. Furthermore, it is described that pearlescent agents based on fatty acids, their salts and their esters as pearlescent components have only a low thermal stability and are dissolved or dissolved at the usual use concentrations in surfactant formulations in the course of storage. These disadvantages have meant that such systems have not become established on the market.
- the invention relates to a method for producing a pearlescent dispersion
- R is a straight-chain or branched saturated hydrocarbon radical having 14 to 26 carbon atoms and M is hydrogen, an alkali metal ion, alkaline earth metal ion, ammonium ion or an ammonium ion substituted with organic radicals, or mixtures thereof;
- Water, one or more dispersants and optionally further additives are heated to a temperature which corresponds approximately to the temperature reached in step 1 and adjusts the pH of this mixture to a value less than 7;
- the homogeneous emulsion obtained in step 4 is cooled from the temperature it has at the end of step 4 in stages separated from one another to the temperature at which it is stored.
- Fatty acids, fatty acid mixtures and / or fatty acid salts are collectively referred to below as fatty acids.
- R is preferably C 16 to 0 2 2 ⁇ alkyl.
- the group R - CO - can be derived from fatty acids such as, for example, capric acid, lauic acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, coconut fatty acid and tallow fatty acid and mixtures thereof.
- Technical fatty acid cuts are also suitable. 10 to 20% by weight of fatty acids are preferably used.
- the pearlescent dispersion according to the invention can contain up to 10% by weight of polyvalent C 2 -C 8 -alcohols as further conventional additives.
- Preferred polyhydric alcohols are C 2 - to C 6 -polyols, in particular ethylene glycol, 1, 2- and 1, 3-propylene glycol, glycerin, di- and triethylene glycol, erythritol, arabitol, adonitol, xylitol, sorbitol, mannitol and dulcitol.
- Other common additives include, for example, preservatives and buffer substances.
- the storage temperature for the pearlescent dispersion according to the invention is preferably between 10 and 30, in particular between 15 and 25 ° C.
- the following process is preferred for producing the pearlescent dispersions according to the invention.
- Demineralized water, one or more dispersants and optionally, for example, benzoic acid are placed in a mixing vessel (such as a heatable stirred kettle).
- the pH is adjusted with sodium hydroxide solution so that the final pH of the pearlescent dispersion is between 4 and 6, preferably between 4.1 and 5.2, particularly preferably between 4.2 and 4.8, in particular between 4.2 and 4 , 5 lies.
- the set pH value has a great influence on the type and quality of the pearlescent effect that can be achieved.
- the solution is heated to 70 to 95 ° C, preferably 85 to 90 ° C.
- the fatty acid preferably stearic and / or behenic acid
- the fatty acid is melted homogeneously in a second kettle at a temperature of 70 to 95 ° C.
- the homogeneously melted fatty acid is introduced at the specified temperature of 70 to 95 ° C with stirring in the aforementioned aqueous solution.
- the resulting emulsion is kept at 70 to 95.degree. C., preferably at 85 to 90.degree. C. for 10 to 30 minutes with stirring for temperature control and homogenization.
- the stirring speed is 80 to 200 revolutions per minute depending on the type of stirrer and degree of filling of the mixing vessel.
- homogenizers or other high-speed mixing devices can also be used to homogenize the present emulsion.
- the subsequent cooling takes place in several stages under controlled conditions and has a major influence on the quality of the pearlescent effect that can be achieved. It may be preferred to cool down in at least 3 stages, these 3 stages being designated by the numbers 1, 3 and 5 in the following list.
- the conditions can be changed depending on the composition of the pearlescent concentrate:
- 1st stage Cool within 10 to 30 minutes to 80 to 45 ° C, preferably to 75 to 80 ° C.
- 2nd stage Within 10 minutes to 6 hours from 75 to 80 ° C to 35 to 65 ° C, preferably to 60 to 65 ° C.
- 3rd stage within 10 minutes to 2 hours from 60 to 65 ° C
- 5th stage Within 10 to 30 minutes from 35 ° C to storage temperature.
- compositions of the pearlescent concentrate may be preferred for certain compositions of the pearlescent concentrate to cool in 5 stages. If the pearlescent concentrate is stirred during cooling, the stirring speed can be reduced to 10 to 100 revolutions per minute, preferably 10 to 40 revolutions per minute, depending on the type of stirrer and the degree of filling of the mixing vessel. The fatty acid crystallizes out during cooling, and the liquid pearlescent concentrate can be filled at storage temperature.
- the aqueous pearlescent dispersions according to the invention are flowable and pumpable and can therefore be used without difficulty on automatic pumping, metering and mixing systems. They have the following advantages over the dispersions of the prior art: They show better foaming behavior in the Ross-Miles test. No glycol or ethylene glycol stearates or esters are used. They can be produced without alcohols. They are free from nitrosable amines or alkanolamides. They make less demands on process control and equipment during production Pearlescent concentrates are thin and therefore very pumpable. The low viscosity also has a favorable effect on the Ross-Miles test. No glycol or ethylene glycol stearates or esters are used. They can be produced without alcohols. They are free from nitrosable amines or alkanolamides. They make less demands on process control and equipment during production Pearlescent concentrates are thin and therefore very pumpable. The low viscosity also has a favorable effect on the
- the pearlescent dispersions according to the invention are suitable for producing pearlescent liquid, aqueous surfactant formulations.
- they can be incorporated into liquid mild detergents, universal detergents, hand dishwashing detergents, rinse aids, liquid detergents and disinfectants, liquid soaps, hair shampoos, hair rinses, hair colorants, hair waving agents, foam baths, facial cleansers, shower bath preparations and 2 in 1 formulations.
- the pearlescent dispersions according to the invention support the conditioning effect of hair shampoos, in particular of so-called 2 in 1 shampoos, which contain water-soluble and / or non-water-soluble dispersed agents, such as silicone derivatives (e.g. dimethicone).
- the aqueous pearlescent dispersions according to the invention can be easily incorporated cold in surfactant formulations, as a result of which they obtain the desired pearlescent.
- the required amount of pearlescent dispersion is 1 to 10% by weight, preferably 2 to 5% by weight, based on the weight of the surfactant formulation to be treated.
- the pearlescent dispersion is added to the surfactant formulations in the stated amount, preferably as the last component, at room temperature with stirring.
- the pearlescent concentrate unfolds its shine and its yield in the formulation after approx. 1-5 days. Afterwards, end products are obtained which have an excellent stable pearlescent.
- the surfactant-containing compositions in which the pearlescent dispersions according to the invention can be used are described below.
- Suitable anionic surfactants are sulfonates, sulfates, carboxylates, phosphates and mixtures of the compounds mentioned.
- Suitable cations are alkali metals, e.g. Sodium or potassium or alkaline earth metals, e.g. Calcium or magnesium and ammonium, substituted ammonium compounds, including mono-, di- or triethanolammonium cations and mixtures of the cations.
- the following types of anionic surfactants are of particular interest: alkyl ester sulfonates, alkyl sulfates, alkyl ether sulfates, alkyl benzene sulfonates, secondary alkane sulfonates, soaps as described below.
- Alkyl ester sulfonates include linear esters of C 8 -C 20 carboxylic acids (ie fatty acids) which are sulfonated using gaseous SO 3 , as described in "The Journal of the American Oil Chemists Society” 52 (1975), pp. 323-329. Suitable starting materials are natural fats such as tallow, palm oil or coconut oil, but can also be synthetic in nature. Preferred alkyl ester sulfonates, especially for detergent applications, are compounds of the formula
- R 1 is a C 8 -C 20 hydrocarbon radical, preferably alkyl and R is a C 1 -C 6 hydrocarbon radical, preferably alkyl.
- M stands for a cation that forms a water-soluble salt with the alkyl ester sulfonate. Suitable cations are sodium, potassium, lithium or ammonium cations, such as monoethanolamine, diethanolamine and triethanolamine.
- R 1 is preferably C 10 -C 16 alkyl and R is methyl, ethyl or isopropyl. Methyl ester sulfonates in which R 1 is C 10 -C 16 alkyl are particularly preferred.
- Alkyl sulfates are here water-soluble salts or acids of the formula ROS0 3 M, where n R is preferably a C 10 -C 24 hydrocarbon radical, preferably C 10 -C 20 alkyl or hydroxyalkyl, particularly preferably C 12 -C 18 alkyl or hydroxyalkyl.
- M is hydrogen or a cation, for example an alkali metal cation (for example sodium, potassium, lithium), ammonium or substituted ammonium for example methyl, dimethyl and trimethylammonium cations and quaternary ammonium cations such as tetramethylammonium and dimethylpiperidinium cations and quaternary ammonium cations derived from alkylamines such as ethylamine Diethylamine, triethylamine and mixtures thereof.
- Alkyl chains with C 12 -C 16 are preferred for low washing temperatures (eg below approx. 50 ° C) and alkyl chains with C 16 -C 18 for higher washing temperatures (eg above approx. 50 ° C).
- Alkyl ether sulfates are water-soluble salts or acids of the formula RO (A) m S0 3 M, in which R is an unsubstituted C 10 -C 24 alkyl or hydroxyalkyl radical, preferably a C 12 -C 20 alkyl or hydroxyalkyl radical, particularly preferably C 12 -C 18 represents alkyl or hydroxyalkyl.
- A is an ethoxy or propoxy unit
- m is a number greater than 0, preferably between approximately 0.5 and approximately 6, particularly preferably between approximately 0.5 and approximately 3, and
- M is a hydrogen atom or a cation such as, for example Sodium, potassium, lithium, calcium, magnesium, ammonium or a substituted ammonium cation.
- substituted ammonium cations are methyl, dimethyl, trimethylammonium and quaternary ammonium cations such as tetramethylammonium and dimethylpiperidinium cations, as well as those derived from alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof.
- alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof.
- Examples include C 12 -C 18 fatty alcohol ether sulfates, the ethylene oxide content being 1, 2, 2.5, 3 or 4 moles per mole of fatty alcohol ether sulfate, and in which M is sodium or potassium.
- the alkyl group can be either saturated or unsaturated, branched or linear and optionally substituted with a hydroxyl group.
- the sulfo group can take any position on the entire C chain, the primary methyl groups at the beginning and end of the chain having no sulfo groups.
- the preferred secondary alkanesulfonates contain linear alkyl chains with about 9 to 25 carbon atoms, preferably from about 10 to about 20 carbon atoms and particularly preferably from about 13 to 17 carbon atoms.
- Sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium are preferred as the cation.
- alkenyl or alkylbenzenesulfonates are alkenyl or alkylbenzenesulfonates.
- the alkenyl or alkyl group can be branched or linear and optionally substituted with a hydroxyl group.
- the preferred alkylbenzenesulfonates contain linear alkyl chains with about 9 to 25 carbon atoms, preferably from about 10 to about 13 carbon atoms, the cation is sodium, potassium, ammonium, mono-, di- or triethanolammonium, calcium or magnesium and mixtures thereof. Magnesium is preferred as the cation for mild surfactant systems, while sodium is preferred for standard washing applications. The same applies to alkenylbenzenesulfonates
- anionic surfactants also includes olefin sulfonates which are obtained by sulfonating C 12 -C 24 , preferably C 14 -C 16 ⁇ -olefins with sulfur trioxide and subsequent neutralization. Due to the manufacturing process, these olefin sulfonates can contain smaller amounts of hydroxyalkane sulfonates and alkane disulfonates. Special mixtures of olefin sulfonates are described in US 3,332,880.
- Suitable anionic surfactants are carboxylates, e.g. Fatty acid soaps and comparable surfactants.
- the soaps can be saturated or unsaturated and can contain various substituents such as hydroxyl groups or sulfonate groups.
- Linear saturated or unsaturated hydrocarbon radicals are preferred as a proportion with approximately 6 to approximately 30, preferably approximately 10 to approximately 18, carbon atoms.
- Suitable anionic surfactants are salts of acylaminocarboxylic acids, the acyl sarcosinates formed in the alkaline medium by reaction of fatty acid chlorides with sodium sarcosinate; Fatty acid-protein condensation products obtained by reacting fatty acid chlorides with oligopeptides; Salts of alkylsulfamidocarboxylic acids, salts of Alkyl and alkylaryl ether carboxylic acids; C 8 -C 2 olefin sulfonates, sulfonated polycarboxylic acids, prepared by sulfonation of the pyrolysis products of alkaline earth metal citrates, as described, for example, in GB-1, 082,179; Alkylglycerol sulfates, fatty acylglycerol sulfates, alkylphenol ether sulfates, primary paraffin sulfonates, alkyl phosphates, alkyl ether phosphates
- Polyethylene, polypropylene and polybutylene oxide condensates of alkylphenols.
- These compounds include the condensation products of alkylphenols with a C 6 -C 20 alkyl group, which can be either linear or branched, with alkene oxides. Compounds with about 5 to 25 moles of ethylene oxide per mole of alkylphenol are preferred.
- Commercially available surfactants of this type include Igepal® CO-630, Triton® X-45, X-114, X-100 and X102, and the ®Arkopal-N brands from Hoechst AG.
- the alkyl chain of the aliphatic alcohols can be linear or branched, primary or secondary, and generally contains from about 8 to about 22 carbon atoms.
- the condensation products of C 10 -C 20 alcohols are particularly preferred, with about 2 to about 18 moles of ethylene oxide per mole of alcohol.
- the alkyl chain can be saturated or also be unsaturated.
- the alcohol ethoxylates can have a narrow (“narrow range ethoxylates") or a broad homolog distribution of the ethylene oxide ("broad range ethoxylates").
- nonionic surfactants of this type are Teritol® 15-S-9 (condensation product of a C ⁇ -C ⁇ linear secondary alcohol with 9 mol of ethylene oxide), Tergitol® 24-L-NMW (condensation product of a C 12 -C 14 linearearene primary alcohol with 6 mol ethylene oxide with a narrow molecular weight distribution).
- Genapol® brands of Hoechst AG also fall under this product class.
- Condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
- the hydrophobic part of these compounds preferably has a molecular weight between approximately 1500 and approximately 1800.
- the addition of ethylene oxide to this hydrophobic part leads to an improvement in water solubility.
- the product is liquid up to a polyoxyethylene content of approx. 50% of the total weight of the condensation product, which corresponds to a condensation with up to approx. 40 mol ethylene oxide.
- Commercially available examples of this product class are the Pluronic® brands from BASF and the ®Genapol PF brands from Hoechst AG.
- the hydrophobic unit of these compounds consists of the reaction product of ethylenediamine with excess propylene oxide and generally has a molecular weight of approximately 2500 to approximately 3000. Ethylene oxide is added to this hydrophobic unit until the product has a content of approximately 40 to approximately 80% by weight of polyoxyethylene and a molecular weight of approximately 5000 to approximately 11000.
- Commercially available examples of this class of compounds are the ®Tetronic brands from BASF and the ®Genapol PN brands from Hoechst AG.
- nonionic compounds includes water-soluble amine oxides, water-soluble phosphine oxides and water-soluble sulfoxides each having an alkyl radical of from about 10 to about 18 carbon atoms.
- Semipolar nonionic surfactants are also amine oxides of the formula
- R here is an alkyl-hydroxyalkyl or alkylphenol group each having about 8 to about 22 carbon atoms
- R 2 is an alkylene or hydroxyalkylene group having about 2 to 3 carbon atoms or mixtures thereof
- each radical R 1 is an alkyl or hydroxyalkyl group with about 1 to about 3 carbon atoms or a polyethylene oxide group with about 1 to about 3 ethylene oxide units.
- the R 1 groups can be connected to one another via an oxygen or nitrogen atom and thus form a ring.
- Amine oxides of this type are in particular C 10 -C 18 alkyldimethylamine oxides and C 8 -C 12 alkoxyethyl-dihydroxyethylamine oxides.
- Fatty acid amides have the formula
- R is an alkyl group with about 7 to about 21, preferably about 9 to about 17 carbon atoms and each radical R 1 is hydrogen, C r C 4 alkyl, C, -C - hydroxyalkyl or (C 2 H 4 0 ) x means H, where x varies from approx. 1 to approx. 3.
- C 8 -C 20 amides, monoethanolamides, diethanolamides and isopropanolamides are preferred.
- non-ionic surfactants are in particular alkyl and alkenyl oligoglycosides and fatty acid polyglycol esters or fatty amine polyglycol esters each having 8 to 20, preferably 12 to 18 carbon atoms in the fatty alkyl radical, alkoxylated triglycamides, mixed ethers or mixed formyls, fatty acid N-alkyl glucamides, protein hydrolyzates, phosphine oxides or dialkyl sulfoxides.
- amphoteric or zwitterionic surfactants are alkyl betaines, alkylamide betaines, aminopropionates, aminoglycinates, or amphoteric imdiazolinium compounds of the formula
- R 1 is C 8 -C 22 alkyl or alkenyl
- R 2 is hydrogen or CH 2 C0 2 M
- R 3 CH 2 CH 2 OH or CH 2 CH 2 OCH 2 CH 2 COOM
- R 4 is hydrogen, CH 2 CH 2 OH or CH 2 CH 2 COOM
- Z means CO 2 M or CH 2 CO 2 M
- n 2 or 3 preferably 2
- M is hydrogen or a cation such as alkali metal, alkaline earth metal, ammonia or alkanolammonium.
- Preferred amphoteric surfactants of this formula are monocarboxylates and dicarboxylates. Examples include cocoamphocarboxypropionate, cocoamidocarboxypropionic acid, cocoamphocarboxyglycinate (also known as cocoamphodiacetate) and cocoamphoacetate.
- amphoteric surfactants are alkyldimethylbetaines and alkyldipolyethoxybetaines with an alkyl radical which can be linear or branched, with about 8 to about 22 carbon atoms, preferably with 8 to 18 carbon atoms and particularly preferably with about 12 to about 18 carbon atoms.
- This Connections are marketed, for example, by Hoechst AG under the trade name ®Genagen LAB.
- Quaternary ammonium salts of the type are used as cationic surfactants
- R 1 "C 8 -C 24 n- or iso-alkyl, preferably C 10 -C 18 n-alkyl
- R 2 C 1 -C 4 alkyl, preferably methyl
- R 3 R 1 or R 2
- R 4 zz R 2 or hydroxyethyl or hydroxypropyl or their
- distearyldimethylammonium chloride examples include distearyldimethylammonium chloride, ditalgalkyldimethylammonium chloride, ditalgalkylmethylhydroxypropylammonium chloride, cetyltrimethylammonium chloride or also the corresponding benzyl derivatives such as dodecyldimethylbenzylammonium chloride.
- Cyclic quaternary ammonium salts such as alkyl morpholine derivatives can also be used.
- imidazolinium compounds (1) and imidazoline derivatives (2) can be used.
- R C 8 -C 24 n- or iso-alkyl, preferably C 10 -C 18 n-alkyl
- A -NH-CO-, -CO-NH-, -O-CO-, -CO-O-
- esterquats are reaction products of alkanolamines and fatty acids, which are then quaternized with customary alkylation or hydroxyalkylation agents.
- Preferred alkanolamines are compounds according to the formula
- R 1 C r C 3 hydroxyalkyl, preferably hydroxyethyl and
- R 2 , R3 independently of one another R 1 or C r C 3 alkyl, preferably methyl.
- Triethanolamine and methyldiethanolamine are particularly preferred.
- ester quats are aminoglycerol derivatives, such as.
- Alkylation or hydroxyalkylation agents are alkyl halides, preferably methyl chloride, dimethyl sulfate, ethylene oxide and propylene oxide.
- ester quats are compounds of the formulas:
- RC-0 is derived from C 8 -C 2 fatty acids, which can be saturated or unsaturated.
- examples include caproic acid, caprylic acid, hydrogenated or not or only partially hydrogenated tallow fatty acids, stearic acid, oleic acid, linolenic acid, behenic acid, palminstearic acid, myristic acid and elaidic acid.
- n is in the range from 0 to 10, preferably 0 to 3, particularly preferably 0 to 1.
- Temperature program I 15 min at 85 ° C, in 150 min to 60 ° C, 10 min at
- Temperature program II 15 min at 90 ° C, in 120 min to 60 ° C, in 90 min to 30 ° C.
- Temperature program III 15 min at 90 ° C, 30 min to 75 ° C, 240 min to 25 ° C.
- Temperature program IV 15 minutes at 90 ° C, 15 minutes to 85 ° C, 240 minutes to 60 ° C, 120 minutes to 25 ° C.
- Temperature program V 15 min at 90 ° C, in 15 min to 80 ° C, in 300 min to 60 ° C, in 60 min to 25 ° C.
- Temperature program VI 15 min at 90 ° C, in 15 min to 75 ° C, in 360 min to 60 ° C, in 120 min to 25 ° C.
- Temperature program VII 15 min at 90 ° C, in 15 min to 75 ° C, in 5 min
- Temperature program VIII 15 minutes at 90 ° C, 15 minutes to 80 ° C, 120 minutes to 60 ° C, 90 minutes to 25 ° C.
- Temperature program X 15 min at 90 ° C, in 15 min at 80 ° C, in 120 min at 60 ° C, in 90 min at 25 ° C, in 60 min at 50 ° C, for 15 min at 50 ° C, Cool to 25 ° C in 90 min.
- Temperature program XI 90 to 75 ° C in 15 min, 75 to 65 ° C in 90 min, 65 to 45X in 20 min, 45 to 35 ° C in 90 min, 35 to
- Temperature program XII 90 to 45 ° C in 70 min, 45 to 35 ° C in 2 hours,
- Temperature program XIII 90 to 75 ° C in 15 min, 75 to 60 ° C in 2 hours,
- Temperature program XIV 90 to 25 ° C in 90 min.
- Temperature program XV 90 to 75 ° C in 15 minutes, 75 to 60 ° C in 3 hours, 60 to 45 ° C in 20 minutes, 45 to 35 ° C in 3 hours, 35 to 25 ° C in 15 minutes.
- Temperature program XVI 90 to 75 ° C in 15 min, 75 to 60 ° C in 45 min, 60 to 45 ° C in 20 min, 45 to 35 ° C in 45 min, 35 to 25 ° C in 15 min.
- Temperature program XVII 90 to 45 ° C in 70 min, 45 to 35 ° C in 45 min, 35 to 25 ° C in 15 min.
- Temperature program XVIII 90 to 75 ° C in 15 min, 75 to 35 ° C in 7 hours, 35 to 25 ° C in 15 min.
- Temperature program XIX 90 to 75 ° C in 15 min, 75 to 35 ° C in 90 min, 35 to 25 ° C in 15 min.
- Temperature program XX 90 to 80 ° C in 15 minutes, 80 to 25 ° C in 9 hours.
- Euperlan® PK 3000 is a pearlescent agent in which monoglycol mono- and distearate are used as pearlescent components. It also contains alkyl amide propyl betaine, alcohol oxyethylates and table salt.
- SCID Hostapon® SCID acyl isethionate
- PG pearlescent
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Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP52209298A JP2001504532A (ja) | 1996-11-11 | 1997-10-27 | 真珠様成分として脂肪酸を含有する流動性の真珠様光沢水性分散物を製造する方法 |
Applications Claiming Priority (2)
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DE19646413.7 | 1996-11-11 | ||
DE1996146413 DE19646413A1 (de) | 1996-11-11 | 1996-11-11 | Verfahren zur Herstellung einer fließfähigen, wäßrigen Perlglanzdispersion mit Fettsäure als perlglanzgebender Komponente |
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WO1998020850A1 true WO1998020850A1 (de) | 1998-05-22 |
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PCT/EP1997/005930 WO1998020850A1 (de) | 1996-11-11 | 1997-10-27 | Verfahren zur herstellung einer fliessfähigen, wässrigen perlglanzdispersion mit fettsäure als perlglanzgebender komponente |
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JP (1) | JP2001504532A (de) |
CN (1) | CN1238679A (de) |
DE (1) | DE19646413A1 (de) |
WO (1) | WO1998020850A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0974338A2 (de) * | 1998-07-22 | 2000-01-26 | Beiersdorf Aktiengesellschaft | Pflegende kosmetische und dermatologische Zubereitungen mit einem Gehalt an Fettsäuren |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0846752A3 (de) * | 1996-12-03 | 1999-12-01 | Clariant GmbH | Fliessfähige, wässrige Perlglanzdispersion mit Behensäure als perlglanzgebender Komponente |
DE19747450C2 (de) * | 1997-10-27 | 1999-09-16 | Henkel Kgaa | Wäßrige Perlglanzkonzentrate |
DE10219523A1 (de) * | 2002-05-02 | 2003-11-13 | Wella Ag | Verfahren zur technischen Produktion haar- oder hautkosmetischer Produkte unter Verwendung von Apparaturen mit Mikrostruktureinheiten |
JP2008094725A (ja) * | 2006-10-06 | 2008-04-24 | Kracie Home Products Kk | パール状皮膚洗浄剤組成物 |
WO2014070689A1 (en) | 2012-10-29 | 2014-05-08 | The Procter & Gamble Company | Personal care compositions having a tan delta of 0.30 or more at 10°c |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0300379A2 (de) * | 1987-07-24 | 1989-01-25 | Henkel Kommanditgesellschaft auf Aktien | Alkanolamidfreies Perlglanzkonzentrat |
EP0376083A2 (de) * | 1988-12-23 | 1990-07-04 | Henkel Kommanditgesellschaft auf Aktien | Fliessfähiges Perlglanzkonzentrat |
DE4103551A1 (de) * | 1991-02-06 | 1992-08-13 | Henkel Kgaa | Fliessfaehiges perlglanzkonzentrat |
EP0555690A1 (de) * | 1992-01-30 | 1993-08-18 | Helene Curtis, Inc. | Stabiles Haarpflegeshampoo enthaltend eine Mischung von Fettsäure und Fettalkohol |
EP0654259A1 (de) * | 1993-11-19 | 1995-05-24 | Kao Corporation | Mittel zur Haarpflege |
-
1996
- 1996-11-11 DE DE1996146413 patent/DE19646413A1/de not_active Withdrawn
-
1997
- 1997-10-27 WO PCT/EP1997/005930 patent/WO1998020850A1/de not_active Application Discontinuation
- 1997-10-27 CN CN 97180155 patent/CN1238679A/zh active Pending
- 1997-10-27 JP JP52209298A patent/JP2001504532A/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0300379A2 (de) * | 1987-07-24 | 1989-01-25 | Henkel Kommanditgesellschaft auf Aktien | Alkanolamidfreies Perlglanzkonzentrat |
EP0376083A2 (de) * | 1988-12-23 | 1990-07-04 | Henkel Kommanditgesellschaft auf Aktien | Fliessfähiges Perlglanzkonzentrat |
DE4103551A1 (de) * | 1991-02-06 | 1992-08-13 | Henkel Kgaa | Fliessfaehiges perlglanzkonzentrat |
EP0555690A1 (de) * | 1992-01-30 | 1993-08-18 | Helene Curtis, Inc. | Stabiles Haarpflegeshampoo enthaltend eine Mischung von Fettsäure und Fettalkohol |
EP0654259A1 (de) * | 1993-11-19 | 1995-05-24 | Kao Corporation | Mittel zur Haarpflege |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0974338A2 (de) * | 1998-07-22 | 2000-01-26 | Beiersdorf Aktiengesellschaft | Pflegende kosmetische und dermatologische Zubereitungen mit einem Gehalt an Fettsäuren |
EP0974338A3 (de) * | 1998-07-22 | 2003-05-21 | Beiersdorf Aktiengesellschaft | Pflegende kosmetische und dermatologische Zubereitungen mit einem Gehalt an Fettsäuren |
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JP2001504532A (ja) | 2001-04-03 |
CN1238679A (zh) | 1999-12-15 |
DE19646413A1 (de) | 1998-05-14 |
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