EP1177274B1 - Cold production method for pearly lustre surfactant preparations - Google Patents
Cold production method for pearly lustre surfactant preparations Download PDFInfo
- Publication number
- EP1177274B1 EP1177274B1 EP00929458A EP00929458A EP1177274B1 EP 1177274 B1 EP1177274 B1 EP 1177274B1 EP 00929458 A EP00929458 A EP 00929458A EP 00929458 A EP00929458 A EP 00929458A EP 1177274 B1 EP1177274 B1 EP 1177274B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- fatty
- acid
- esters
- preparations
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims description 29
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
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- 239000002453 shampoo Substances 0.000 description 8
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- 238000002844 melting Methods 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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- CQDMCVJMVGGZHQ-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(octadecanoyloxymethyl)butyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)(CO)COC(=O)CCCCCCCCCCCCCCCCC CQDMCVJMVGGZHQ-UHFFFAOYSA-N 0.000 description 1
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
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- 230000000035 biogenic effect Effects 0.000 description 1
- GLQBXSIPUULYOG-UHFFFAOYSA-M bismuth oxychloride Chemical class Cl[Bi]=O GLQBXSIPUULYOG-UHFFFAOYSA-M 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 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
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- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
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- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- PNSDHQDPDMOPCP-UHFFFAOYSA-N dioctadecyl 2-hydroxybutanedioate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC(O)C(=O)OCCCCCCCCCCCCCCCCCC PNSDHQDPDMOPCP-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940085632 distearyl ether Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 229940048848 lauryl glucoside Drugs 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- KHLCTMQBMINUNT-UHFFFAOYSA-N octadecane-1,12-diol Chemical compound CCCCCCC(O)CCCCCCCCCCCO KHLCTMQBMINUNT-UHFFFAOYSA-N 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000003094 perturbing effect Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
Definitions
- the invention is in the field of pearlescent preparations, especially cosmetics and relates to a process for preparing these agents by the cold route.
- Pearlescent concentrates in the form of flowable aqueous dispersions are known, for example, from German Patent Applications DE 3843572 A1 and DE 4103551 A1 (Henkel), which contain 15 to 40% by weight pearlescent components, 5 to 55% by weight emulsifiers and 0.1 to 5 or 15 to 40 wt .-% polyols.
- the pearlescent waxes are acylated polyalkylene glycols, monoalkanolamides, linear, saturated fatty acids or ketosulfones.
- the two European patents EP 0181773 B1 and EP 0285389 B1 propose shampoo compositions containing surfactants, non-volatile silicones and pearlescent waxes.
- the subject of European Patent Application EP 0205922 A2 (Henkel) are flowable pearlescent concentrates which contain 5 to 15% by weight of acylated polyglycols, 1 to 6% by weight of fatty acid monoethanolamides and 1 to 5% by weight of nonionic emulsifiers.
- nonionic, flowable pearlescent dispersions can also be obtained by preparing mixtures of 5 to 30% by weight of acylated polyglycols and 0.1 to 20% by weight of selected nonionic surfactants.
- European Patent Application EP 0581193 A2 also discloses flowable, preservative-free pearlescent dispersions which contain acylated polyglycol ethers, betaines, anionic surfactants and glycerol.
- European Patent Application EP 0684302 A1 proposes the use of polyglycerol esters as crystallization auxiliaries for the preparation of pearlescent concentrates.
- pearlescent waxes have melting points above 80 ° C and therefore can be do not mix cold into aqueous formulations.
- the skilled person is therefore forced to one Hot process to work, i. melt the waxes and slowly crystallize in the formulation let the fineness of the crystals and thus the brilliance of the pearlescent a Function of the cooling rate is. It is therefore immediately clear that such processes take time and energy are so that there is a desire for a cheaper alternative.
- pearlescent concentrates which are more or less concentrated surface-active preparations which already contain the pearlescent waxes in finely divided, i.e. pearlescent form and are stabilized by emulsifiers.
- Such pearlescent concentrates can be processed cold, but the actual problem is thereby not solved, but only shifted to the stage of the manufacturer of these intermediates, as the concentrates in turn, of course, are accessible only by a hot process again.
- the object of the present invention has therefore been to provide a method available which is the cold incorporation of pearlescent waxes into surfactant preparations - be it Intermediates, such as e.g. Pearlescent concentrates or final formulations, e.g. Shampoos - allowed. At the same time, neither the brilliance of the pearlescence nor the stability was due to the cold process the formulations are adversely affected.
- the invention relates to a process for the cold preparation of pearlescent surfactant preparations, in which aqueous surfactant solutions are initially introduced and at temperatures in the range from 10 to 45, preferably 15 to 25 ° C mixtures of pearlescent waxes and Polyolestem stirred.
- the Melting point of pearlescent wax so low that their cold (10 to 25 ° C) incorporation into Surfactant formulations is easily possible.
- the agents Regardless of whether it is the preparations intermediate products (e.g., pearlescent concentrates) or final formulations for the consumer (e.g., shampoos, dishwashing detergent), the agents have brilliant pearlescence, are storage stable and also allow the incorporation of difficult-to-formulate ingredients, e.g. Silicone oils.
- the invention includes the recognition that not only pearlescent agents are produced in this way but, depending on the type of wax and the emulsifier, also those which have an intense white turbidity.
- the surface-active preparations may be intermediates, as pearlescent concentrates or final formulations for the consumer, e.g. Hair shampoos or Dishwashing act.
- surfactants in the preparations anionic, nonionic, cationic and / or amphoteric or amphoteric surfactants whose proportion of the means depending on whether it is a concentrate or a dilution, in Range of 1 to 35, preferably 5 to 15 or 15 to 40, preferably 25 to 35 wt .-% lie can.
- anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates , Mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates,
- nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, hydroxy mixed ethers, optionally partially oxidized alk (en) yloligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates (in particular vegetable products Wheat base), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
- cationic surfactants are quaternary ammonium compounds such as dimethyl distearyl ammonium chloride and ester quats, especially quaternized fatty acid trialkanolamine ester salts.
- amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
- the surfactants mentioned are exclusively known compounds. With regard to the structure and production of these substances, reference may be made to relevant reviews, for example J.Falbe (ed.), “Surfactants in Consumer Products”, Springer Verlag, Berlin, 1987, pp. 54-124 or J. Falbe (ed.), “Catalysts, Surfactants and mineral oil additives ", Thieme Verlag, Stuttgart, 1978, pp. 123-217 .
- the surface-active preparations may contain other customary auxiliaries and additives, such as, for example, oil bodies, superfatting agents, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active substances, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, UV sun protection factors, antioxidants , Hydrotropes, preservatives, insect repellents, self-tanners, solubilizers, perfume oils, dyes and the like.
- auxiliaries and additives such as, for example, oil bodies, superfatting agents, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active substances, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, UV sun protection factors, antioxidants , Hydrotropes, preservatives, insect repellents, self-tanners, solubilizers, perfume oils, dyes and the like.
- Suitable pearlescing waxes are, for example: alkylene glycol esters, fatty acid alkanolamides, partial glycerides, Esters of polybasic, optionally hydroxysubstituted carboxylic acids, fatty alcohols, Fatty acids, fatty ketones, fatty aldehydes, fatty ethers, fatty carbonates, ring-opening products of olefin epoxides as well as their mixtures.
- the alkylene glycol esters which form component (a1) are usually mono- and / or diesters of alkylene glycols which follow formula (III) , R 5 CO (OA) n OR 6 (III) in the R 5 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R 6 is hydrogen or R 5 CO and A is a linear or branched alkylene radical having 2 to 4 carbon atoms and n is from 1 to 5 stands.
- Typical examples are mono- and / or diesters of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol or tetraethylene glycol with fatty acids having 6 to 22, preferably 12 to 18 carbon atoms as: caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid , Myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, behenic and erucic acids and their technical mixtures. Particularly preferred is the use of ethylene glycol mono- and / or distearate.
- Fatty acid alkanolamides which are suitable as pearlescent waxes of group (a2), follow the formula (IV), R 7 CO-NR 8 -B -OH (IV) in which R 7 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R 8 is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms and B is a linear or branched alkylene group having 1 to 4 carbon atoms.
- Typical examples are condensation products of ethanolamine, methylethanolamine, diethanolamine, propanolamine, methylpropanolamine and dipropanolamine and mixtures thereof with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, Linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. Particularly preferred is the use of stearic acid ethanolamide.
- Partial glycerides having pearlescent properties and constituting component (a3) are mono and / or diesters of glycerol with linear, saturated fatty acids, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, behenic acid and their technical properties Mixtures.
- R 10 and R 11 are independently hydrogen or R 9 CO, x, y and z in total for 0 or for numbers from 1 to 30 and X for an alkali or alkaline earth metal with the proviso is that at least one of the two radicals R 10 and R 11 is hydrogen.
- Typical examples are lauric acid monoglyceride, lauric acid diglyceride, coconut fatty acid monoglyceride, coconut fatty acid triglyceride, palmitic acid monoglyceride, palmitic acid triglyceride, stearic acid monoglyceride, stearic acid diglyceride, tallow fatty acid monoglyceride, tallow fatty acid diglyceride, behenic acid monoglyceride, baryric acid diglyceride and their technical mixtures which, subordinated to the production process, may still contain small amounts of triglyceride.
- esters of polyvalent optionally also come polyfunctional, preferably hydroxy-substituted carboxylic acids with fatty alcohols with 6 to 22 carbon atoms in question.
- metal salts in particular alkali salts, also come in, of monoesters of dicarboxylic acids or of mono- and / or diesters of tricarboxylic acids in Question.
- Esters of polyfunctional carboxylic acids preferably hydroxycarboxylic acids with partial esters of Polyols and the metal salts of the corresponding half esters can be used.
- esters are malonic acid, maleic acid, fumaric acid, adipic acid, sebacic acid, Azelaic acid, dodecanedioic acid, phthalic acid, isophthalic acid and especially succinic acid and malic acid, citric acid and especially tartaric acid and mixtures thereof.
- the fatty alcohols contain from 6 to 22, preferably 12 to 18 and especially 16 to 18 carbon atoms in the alkyl chain.
- Typical examples are caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, Capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, Stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, Linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, Erucyl alcohol and brassidyl alcohol and their technical mixtures.
- the esters can be considered full or Partial esters are present, preferably mono- and especially diesters of carboxylic or hydroxycarboxylic acids used.
- Typical examples are succinic mono- and dilauryl esters, succinic acid mono- and dicetearly esters, succinic mono- and distearyl esters, tartaric mono- and dilauryl esters, tartaric and dicocoalkyl esters, tartaric and dicetearyl tartaric acid, citric acid mono-, di- and tri-lauryl esters, citric acid mono-, di- and tricocoalkyl esters and citric acid mono-, di- and tricetearyl esters and their metal salts, preferably alkali metal salts.
- pearlescent waxes it is possible to use fatty alcohols and / or fatty acids which follow the formula (VI) , R 12 OH (VI) in which R 12 is a linear, optionally hydroxy-substituted alkyl radical and / or acyl radical having 16 to 48, preferably 18 to 36 carbon atoms.
- suitable alcohols are cetearyl alcohol, hydroxystearyl alcohol, behenyl alcohol and oxidation products of long-chain paraffins
- examples of acids are stearic acid, hydroxystearic acid and in particular behenic acid, the latter preferably in a purity above 90% by weight.
- Oily ketones which are suitable as component (a6) preferably follow the formula (VII) , R 13 -CO-R 14 (VII) in which R 13 and R 14 independently of one another are alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have in total at least 24 and preferably 32 to 48 carbon atoms.
- the ketones may be prepared by methods known in the art, for example by pyrolysis of the corresponding fatty acid magnesium salts.
- the ketones can be symmetrical or asymmetrical, but the two radicals R 13 and R 14 preferably differ by only one carbon atom and are derived from fatty acids having 16 to 22 carbon atoms. Stearone is characterized by particularly advantageous pearlescing properties.
- Fettaldehyde suitable as pearlescent waxes (a7) preferably correspond to the formula (VIII), R 15 COH (VIII) in which R 15 CO is a linear or branched acyl radical having 24 to 48, preferably 28 to 32 carbon atoms.
- pearlescing waxes (a8) are fatty ethers of the formula (IX) R 16 -OR 17 (IX) in which R 16 and R 17 independently of one another are alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have in total at least 24 and preferably 32 to 48 carbon atoms.
- Grease ethers of the type mentioned are usually prepared by acid condensation of the corresponding fatty alcohols.
- Fatty ethers having particularly advantageous perturbing properties are obtained by condensation of fatty alcohols having 16 to 22 carbon atoms, such as cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol.
- fatty carbonates preferably of the formula (X) , R 18 O-CO-OR 19 (X) in which R 18 and R 19 independently of one another are alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have in total at least 24 and preferably 32 to 48 carbon atoms.
- the substances are obtained by, for example, transesterifying dimethyl or diethyl carbonate with the corresponding fatty alcohols in a manner known per se.
- the fatty carbonates can be symmetrical or asymmetrical.
- carbonates are used in which R 18 and R 19 are the same and are alkyl radicals having 16 to 22 carbon atoms.
- Transesterification products of dimethyl or diethyl carbonate with cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol in the form of their mono- and diesters or their technical mixtures are particularly preferred.
- the epoxide ring opening products which eventually form group (a10), are known materials commonly prepared by the acid-catalyzed reaction of terminal or internal olefin epoxides with aliphatic alcohols.
- the reaction products preferably follow the formula (XI), in which R 20 and R 21 are hydrogen or an alkyl radical having 10 to 20 carbon atoms, with the proviso that the sum of the carbon atoms of R 20 and R 21 is in the range of 10 to 20 and R 22 is an alkyl and / or or alkenyl radical having 12 to 22 carbon atoms and / or the radical of a polyol having 2 to 15 carbon atoms and 2 to 10 hydroxyl groups.
- Typical examples are ring opening products of ⁇ -dodecene epoxide, ⁇ -hexadecene epoxide, ⁇ -octadecene epoxide, ⁇ -eicosenepoxide, ⁇ -docosenepoxide, i-dodecenepoxide, i-hexadecene epoxide, i-octadecene epoxide, i-eicosenepoxide and / or i-docosenepoxide with lauryl alcohol, coconut fatty alcohol , Myristyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol and / or erucyl alcohol.
- Ring opening products of hexa- and / or octadecene epoxides with fatty alcohols containing 16 to 18 carbon atoms are preferably used.
- polyols are used for the ring opening instead of the fatty alcohols, these are, for example, the following substances: glycerol; Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1,000 daltons; technical oligoglycerine blends having an inherent degree of condensation of from 1.5 to 10 such as technical grade diglycerin blends having a diglycerol content of from 40 to 50 weight percent; Methylol compounds, in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; Niedrigalkylglucoside, in
- the proportion of pearlescent waxes in the preparations is usually in the range from 5 to 45, preferably 10 to 45 and in particular 25 to 35% by weight.
- the pearlescence content is, of course, essential in the case of end formulations less and is typically 0.5 to 3 and preferably 1 to 2 wt .-%.
- Suitable partial glycerides are hydroxystearic hydroxystearic acid diglyceride, isostearic acid, Isostearinklarediglycerid, ⁇ lklaremonaglycerid, oleic acid diglyceride, Ricinolklaremoglycerid, Ricinolklarediglycerid, Linolklaremonoglycerid, Linolklarediglycerid, LinolenTalkremonoglycerid, Linolenchurediglycerid, Erucaklaklamonoglycerid, Erucakladdiglycerid, Weinchurediglycerid, Citronenklamonoglycerid, Citronendiglycerid, ⁇ pfelklamonoglycerid, malic acid diglyceride and technical mixtures thereof, which may contain minor amounts of triglyceride from the manufacturing process.
- sorbitan sorbitan As sorbitan sorbitan, sorbitan sesquiisostearate, Sorbitan, sorbitan triisostearate, sorbitan monooleate, sorbitan, sorbitan, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesquitartrat, Sorbitanditartrat, Sorbitantritartrat come , Sorbitan monocitrate, sorbitan siccitrate, sorbitan di-citrate, sorbit
- polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® GI 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan ® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl -3 distearates (Cremophor® GS 32) and polyglyceryl polyricinoleates (Admul® WOL 1403) polyglyceryl dim
- polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, which are optionally reacted with from 1 to 30 mol of ethylene oxide.
- pearlescent concentrates are produced in the context of the process according to the invention, then this is the case
- Proportion of polyol esters in the preparations usually in the range of 0.5 to 15, preferably 1 to 10 and in particular 5 to 8 wt .-%, it is final formulations is the polyolester content Of course, much less and is typically 0.1 to 1, and preferably about 0.5 Wt .-%.
- the content of the polyol ester based on the amount of pearlescent wax is usually in the range of 1 to 15 and preferably 5 to 10 wt .-%.
- the addition products of ethylene oxide and / or of propylene oxide to fatty alcohols, fatty acids, alkylphenols or castor oil are known, commercially available products. These are mixtures of homologues whose mean degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate, with which the addition reaction is carried out corresponds.
- C 12/18 fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
- C 8/18 alkyl mono- and oligoglycosides, their preparation and their use are known in the art.
- glycoside radical both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable.
- the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
- zwitterionic surfactants can be used as emulsifiers.
- Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacylaminopropyldimethylammoniumglycinat, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline each having 8 to 18 carbon atoms in the alkyl or acyl group and the Kokosacylaminoethylhydroxyethylcarboxymethylglycinat.
- betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacyla
- fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine .
- ampholytic surfactants are understood as meaning those surface-active compounds which, apart from a C 8/18 -alkyl or -acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
- ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C Atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12/18 acylsarcosine.
- cationic surfactants are also suitable as emulsifiers, those of the type of Esterquats, preferably methyl-quaternized difatty acid triethanolamine ester salts, more preferably are.
- the amount used of the polyols is - based on the surfactant preparations - typically in Range of 0.1 to 15 and preferably 0.5 to 5 wt .-%. Be higher amounts of polyol, preferably Glycerol or ethylene glycol used, the concentrates are simultaneously against microbial Infestation stabilized.
- the preparation of the surface-active preparations is usually carried out by reacting an aqueous surfactant or emulsifier solution, optionally together with other auxiliaries and additives at 10 to 25 ° C, and the mixture of pearlescent wax and polyol ester enters at this temperature, homogenized and crystallize.
- an aqueous surfactant or emulsifier solution optionally together with other auxiliaries and additives at 10 to 25 ° C
- the mixture of pearlescent wax and polyol ester enters at this temperature, homogenized and crystallize.
- a concentrated aqueous (anion) surfactant paste to apply the mixture of pearlescent wax and polyol ester in the cold stir and then diluting the mixture with further water to the desired concentration or mixing in the presence of polymeric hydrophilic thickeners, such as hydroxypropylcelluloses, Xanthan gum or carbomer-type polymers.
- the Blend of pearlescent wax and polyol ester even in a subset of the aque
- the preparations were (a) heated to 90 ° C and mixed with 1 g each of the pearlescent waxes V1 to V4 and cooled to ambient temperature within 1 h or (b) at 20 ° C with 1 g of the mixtures 1 to 4. contained.
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Description
Die Erfindung befindet sich auf dem Gebiet der perlglänzenden Zubereitungen, speziell der Kosmetik und betrifft ein Verfahren zur Herstellung dieser Mittel auf kaltem Wege.The invention is in the field of pearlescent preparations, especially cosmetics and relates to a process for preparing these agents by the cold route.
Der weich schimmemde Glanz von Perlen hat auf den Menschen schon seit Jahrtausenden eine besondere Faszination ausgeübt. Es ist daher kein Wunder, daß die Hersteller von kosmetischen Zubereitungen versuchen, ihren Produkten ein attraktives, wertvolles und gehaltvolles Erscheinungsbild zu verleihen. Der erste seit dem Mittelalter in der Kosmetik eingesetzte Perlglanz war eine perlglänzende Paste aus natürlichen Fischschuppen. Zu Anfang dieses Jahrhunderts entdeckte man, daß Wismutoxidchloride ebenfalls in der Lage sind, Perlglanz zu erzeugen. Für die moderne Kosmetik sind hingegen Perlglanzwachse, insbesondere vom Typ der Glycolmono- und -difettsäureester von Bedeutung, die überwiegend zur Erzeugung von Perlglanz in Haarshampoos und Duschgelen eingesetzt werden. Eine Übersicht zu modernen, perlglänzenden Formulierungen findet sich von A.Ansmann und R.Kawa in Parf.Kosm. 75, 578 (1994). The soft, shimmering sheen of pearls has exerted a special fascination on humans for millennia. It is therefore not surprising that the manufacturers of cosmetic preparations try to give their products an attractive, valuable and full-bodied appearance. The first pearlescent used in cosmetics since the Middle Ages was a pearlescent paste made from natural fish scales. At the beginning of this century, it was discovered that bismuth oxide chlorides are also capable of producing pearlescence. On the other hand, pearlescing waxes, in particular of the glycol mono- and di-fatty acid ester type, which are predominantly used to produce pearlescence in hair shampoos and shower gels, are of importance for modern cosmetics. An overview of modern, pearlescent formulations can be found by A.Ansmann and R.Kawa in Parf.Kosm. 75 , 578 (1994).
Der Stand der Technik kennt eine Vielzahl von Formulierungen, die oberflächenaktiven Mitteln den gewünschten Perlglanz verleihen. So sind beispielsweise aus den beiden deutschen Patentanmeldungen DE 3843572 A1 und DE 4103551 A1 (Henkel) Perlglanzkonzentrate in Form fließfähiger wäßriger Dispersionen bekannt, die 15 bis 40 Gew.-% perlglänzender Komponenten, 5 bis 55 Gew.-% Emulgatoren und 0,1 bis 5 bzw. 15 bis 40 Gew.-% Polyole enthalten. Bei den Perlglanzwachsen handelt es sich um acylierte Polyalkylenglycole, Monoalkanolamide, lineare, gesättigte Fettsäuren oder Ketosulfone. In den beiden Europäischen Patentschriften EP 0181773 B1 und EP 0285389 B1 (Procter & Gamble) werden Shampoozusammensetzungen vorgeschlagen, die Tenside, nicht-flüchtige Silicone und Perlglanzwachse enthalten. Gegenstand der Europäischen Patentanmeldung EP 0205922 A2 (Henkel) sind fließfähige Perlglanzkonzentrate, die 5 bis 15 Gew.-% acylierte Polyglycole, 1 bis 6 Gew.-% Fettsäuremonoethanolamide und 1 bis 5 Gew.-% nichtionische Emulgatoren enthalten. Gemäß der Lehre der Europäischen Patentschrift EP 0569843 B1 (Hoechst) lassen sich nichtionische, fließfähige Perlglanzdispersionen auch erhalten, indem man Mischungen von 5 bis 30 Gew.-% acylierten Polyglycolen und 0,1 bis 20 Gew.-% ausgewählten nichtionischen Tensiden herstellt. Aus der Europäischen Patentanmeldung EP 0581193 A2 (Hoechst) sind femer fließfähige, konservierungsmittelfreie Perlglanzdispersionen bekannt, die acylierte Polyglycolether, Betaine, Aniontenside und Glycerin enthalten. Schließlich wird in der Europäischen Patentanmeldung EP 0684302 A1 (Th.Goldschmidt) die Verwendung von Polyglycerinestem als Kristallisationshilfsmittel für die Herstellung von Perlglanzkonzentraten vorgeschlagen.The prior art knows a variety of formulations which impart the desired pearlescence to surfactants. Pearlescent concentrates in the form of flowable aqueous dispersions are known, for example, from German Patent Applications DE 3843572 A1 and DE 4103551 A1 (Henkel), which contain 15 to 40% by weight pearlescent components, 5 to 55% by weight emulsifiers and 0.1 to 5 or 15 to 40 wt .-% polyols. The pearlescent waxes are acylated polyalkylene glycols, monoalkanolamides, linear, saturated fatty acids or ketosulfones. The two European patents EP 0181773 B1 and EP 0285389 B1 (Procter & Gamble) propose shampoo compositions containing surfactants, non-volatile silicones and pearlescent waxes. The subject of European Patent Application EP 0205922 A2 (Henkel) are flowable pearlescent concentrates which contain 5 to 15% by weight of acylated polyglycols, 1 to 6% by weight of fatty acid monoethanolamides and 1 to 5% by weight of nonionic emulsifiers. According to the teaching of European Patent EP 0569843 B1 (Hoechst), nonionic, flowable pearlescent dispersions can also be obtained by preparing mixtures of 5 to 30% by weight of acylated polyglycols and 0.1 to 20% by weight of selected nonionic surfactants. European Patent Application EP 0581193 A2 (Hoechst) also discloses flowable, preservative-free pearlescent dispersions which contain acylated polyglycol ethers, betaines, anionic surfactants and glycerol. Finally, European Patent Application EP 0684302 A1 (Th.Goldschmidt) proposes the use of polyglycerol esters as crystallization auxiliaries for the preparation of pearlescent concentrates.
Handelsübliche Perlglanzwachse weisen Schmelzpunkte oberhalb von 80 °C auf und lassen sich daher nicht kalt in wäßrige Formulierungen einarbeiten. Der Fachmann ist daher gezwungen nach einem Heißverfahren zu arbeiten, d.h. die Wachse aufzuschmelzen und in der Formulierung langsam auskristallisieren zu lassen, wobei die Feinteiligkeit der Kristalle und damit die Brillanz des Perlglanzes eine Funktion der Abkühlgeschwindigkeit ist. Es ist daher sofort klar, daß solche Verfahren zeit- und energieaufwendig sind, so daß der Wunsch nach einer günstigeren Alternative besteht. In der Regel wird der Fachmann daher auf sogenannte Perlglanzkonzentrate ausweichen, bei denen es sich um mehr oder minder konzentrierte tensidische Zubereitungen handelt, die die Perlglanzwachse bereits in feinverteilter, d.h. perlglanzaktiver Form enthalten und durch Emulgatoren stabilisiert sind. Solche Perlglanzkonzentrate lassen sich zwar kalt weiterverarbeiten, doch wird das eigentliche Problem dadurch nicht gelöst, sondern nur auf die Stufe der Hersteller dieser Zwischenprodukte verlagert, da die Konzentrate ihrerseits natürlich wieder nur durch ein Heißverfahren zugänglich sind.Commercially available pearlescent waxes have melting points above 80 ° C and therefore can be do not mix cold into aqueous formulations. The skilled person is therefore forced to one Hot process to work, i. melt the waxes and slowly crystallize in the formulation let the fineness of the crystals and thus the brilliance of the pearlescent a Function of the cooling rate is. It is therefore immediately clear that such processes take time and energy are so that there is a desire for a cheaper alternative. Usually will the expert therefore to dodge so-called pearlescent concentrates, which are more or less concentrated surface-active preparations which already contain the pearlescent waxes in finely divided, i.e. pearlescent form and are stabilized by emulsifiers. Such pearlescent concentrates can be processed cold, but the actual problem is thereby not solved, but only shifted to the stage of the manufacturer of these intermediates, as the concentrates in turn, of course, are accessible only by a hot process again.
Die Aufgabe der vorliegenden Erfindung hat daher darin bestanden, ein Verfahren zur Verfügung zu stellen, welches die kalte Einarbeitung von Perlglanzwachsen in tensidische Zubereitungen - seien es Zwischenprodukte, wie z.B. Perlglanzkonzentrate oder Endformulierungen, wie z.B. Shampoos - gestattet. Gleichzeitig sollte durch den Kaltprozeß weder die Brillanz des Perlglanzes noch die Stabilität der Formulierungen negativ beeinflußt werden.The object of the present invention has therefore been to provide a method available which is the cold incorporation of pearlescent waxes into surfactant preparations - be it Intermediates, such as e.g. Pearlescent concentrates or final formulations, e.g. Shampoos - allowed. At the same time, neither the brilliance of the pearlescence nor the stability was due to the cold process the formulations are adversely affected.
Gegenstand der Erfindung ist ein Verfahren zur kalten Herstellung von perlglänzenden Tensidzubereitungen, bei dem man wäßrige Tensidlösungen vorlegt und bei Temperaturen im Bereich von 10 bis 45, vorzugsweise 15 bis 25 °C Mischungen aus Perlglanzwachsen und Polyolestem einrührt. The invention relates to a process for the cold preparation of pearlescent surfactant preparations, in which aqueous surfactant solutions are initially introduced and at temperatures in the range from 10 to 45, preferably 15 to 25 ° C mixtures of pearlescent waxes and Polyolestem stirred.
Überraschenderweise wurde gefunden, daß schon der Zusatz geringer Mengen von Polyolestem den Schmelzpunkt von Perlglanzwachsen so weit herabsetzt, daß ihre kalte (10 bis 25 °C) Einarbeitung in tensidische Formulierungen problemlos möglich wird. Unabhängig davon, ob es sich bei den Zubereitungen um Zwischenprodukte (z.B. Perlglanzkonzentrate) oder Endformulierungen für den Verbraucher (z.B. Shampoos, Geschirrspülmittel) handelt, weisen die Mittel einen brillanten Perlglanz auf, sind lagerstabil und erlauben auch die Einarbeitung schwierig zu formulierender Inhaltsstoffe, wie z.B. Silicon-öle. Die Erfindung schließt die Erkenntnis ein, daß auf diese Weise nicht nur perlglänzende Mittel hergestellt werden können, sondern - in Abhängigkeit des Wachstyps und des Emulgators - auch solche, die über eine intensive Weißtrübung verfügen.Surprisingly, it has been found that even the addition of small amounts of Polyolestem the Melting point of pearlescent wax so low that their cold (10 to 25 ° C) incorporation into Surfactant formulations is easily possible. Regardless of whether it is the preparations intermediate products (e.g., pearlescent concentrates) or final formulations for the consumer (e.g., shampoos, dishwashing detergent), the agents have brilliant pearlescence, are storage stable and also allow the incorporation of difficult-to-formulate ingredients, e.g. Silicone oils. The invention includes the recognition that not only pearlescent agents are produced in this way but, depending on the type of wax and the emulsifier, also those which have an intense white turbidity.
Wie schon erläutert, kann es sich bei den tensidischen Zubereitungen sowohl um Zwischenprodukte, als Perlglanzkonzentrate oder Endformulierungen für den Verbraucher, wie z.B. Haarshampoos oder Geschirrspülmittel handeln. Als Tenside können in den Zubereitungen anionische, nichtionische, kationische und/oder amphotere bzw. amphotere oberflächenaktive Stoffe enthalten sein, deren Anteil an den Mitteln in Abhängigkeit davon, ob es sich um ein Konzentrat oder eine Verdünnung handelt, im Bereich von 1 bis 35, vorzugsweise 5 bis 15 bzw. 15 bis 40, vorzugsweise 25 bis 35 Gew.-% liegen kann.As already explained, the surface-active preparations may be intermediates, as pearlescent concentrates or final formulations for the consumer, e.g. Hair shampoos or Dishwashing act. As surfactants in the preparations anionic, nonionic, cationic and / or amphoteric or amphoteric surfactants whose proportion of the means depending on whether it is a concentrate or a dilution, in Range of 1 to 35, preferably 5 to 15 or 15 to 40, preferably 25 to 35 wt .-% lie can.
Typische Beispiele für anionische Tenside sind Seifen, Alkylbenzolsulfonate, Alkansulfonate, Olefinsulfonate, Alkylethersulfonate, Glycerinethersulfonate, α-Methylestersulfonate, Sulfofettsäuren, Alkylsulfate, Fettalkoholethersulfate, Glycerinethersulfate, Fettsäureethersulfate, Hydroxymischethersulfate, Monoglycerid(ether)sulfate, Fettsäureamid(ether)sulfate, Mono- und Dialkylsulfosuccinate, Mono- und Dialkylsulfosuccinamate, Sulfotriglyceride, Amidseifen, Ethercarbonsäuren und deren Salze, Fettsäureisethionate, Fettsäuresarcosinate, Fettsäuretauride, N-Acylaminosäuren, wie beispielsweise Acyllactylate, Acyltartrate, Acylglutamate und Acylaspartate, Alkyloligoglucosidsulfate, Proteinfettsäurekondensate (insbesondere pflanzliche Produkte auf Weizenbasis) und Alkyl(ether)phosphate. Sofern die anionischen Tenside Polyglycoletherketten enthalten, können diese eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen.Typical examples of anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefinsulfonates, alkyl ether sulfonates, glycerol ether sulfonates, α-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates , Mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl amino acids such as acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially wheat-based vegetable products) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
Typische Beispiele für nichtionische Tenside sind Fettalkoholpolyglycolether, Alkylphenolpolyglycolether, Fettsäurepolyglycolester, Fettsäureamidpolyglycolether, Fettaminpolyglycolether, alkoxylierte Triglyceride, Mischether bzw. Mischformale, Hydroxymischether, gegebenenfalls partiell oxidierte Alk(en)yloligoglykoside bzw. Glucoronsäurederivate, Fettsäure-N-alkylglucamide, Proteinhydrolysate (insbesondere pflanzliche Produkte auf Weizenbasis), Polyolfettsäureester, Zuckerester, Sorbitanester, Polysorbate und Aminoxide. Sofern die nichtionischen Tenside Polyglycoletherketten enthalten, können diese eine konventionelle, vorzugsweise jedoch eine eingeengte Homologenverteilung aufweisen.Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers, hydroxy mixed ethers, optionally partially oxidized alk (en) yloligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates (in particular vegetable products Wheat base), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these may have a conventional, but preferably a narrow homolog distribution.
Typische Beispiele für kationische Tenside sind quartäre Ammoniumverbindungen, wie beispielsweise das Dimethyldistearylammoniumchlorid, und Esterquats, insbesondere quatemierte Fettsäuretrialkanolaminestersalze.Typical examples of cationic surfactants are quaternary ammonium compounds such as dimethyl distearyl ammonium chloride and ester quats, especially quaternized fatty acid trialkanolamine ester salts.
Typische Beispiele für amphotere bzw. zwitterionische Tenside sind Alkylbetaine, Alkylamidobetaine, Aminopropionate, Aminoglycinate, Imidazoliniumbetaine und Sulfobetaine.Typical examples of amphoteric or zwitterionic surfactants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
Bei den genannten Tensiden handelt es sich ausschließlich um bekannte Verbindungen. Hinsichtlich Struktur und Herstellung dieser Stoffe sei auf einschlägige Übersichtsarbeiten beispielsweise J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, S. 54-124 oder J.Falbe (ed.), "Katalysatoren, Tenside und Mineralöladditive", Thieme Verlag, Stuttgart, 1978, S. 123-217 verwiesen. Die tensidischen Zubereitungen können weitere übliche Hilfs- und Zusatzstoffe enthalten, wie beispielsweise Ölkörper, Überfettungsmittel, Konsistenzgeber, Verdickungsmittel, Polymere, Siliconverbindungen, Fette, Wachse, Stabilisatoren, biogene Wirkstoffe, Deodorantien, Antitranspirantien, Antischuppenmittel, Filmbildner, Quellmittel, UV-Lichtschutzfaktoren, Antioxidantien, Hydrotrope, Konservierungsmittel, Insektenrepellentien, Selbstbräuner, Solubilisatoren, Parfümöle, Farbstoffe und dergleichen.The surfactants mentioned are exclusively known compounds. With regard to the structure and production of these substances, reference may be made to relevant reviews, for example J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J. Falbe (ed.), "Catalysts, Surfactants and mineral oil additives ", Thieme Verlag, Stuttgart, 1978, pp. 123-217 . The surface-active preparations may contain other customary auxiliaries and additives, such as, for example, oil bodies, superfatting agents, bodying agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active substances, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, UV sun protection factors, antioxidants , Hydrotropes, preservatives, insect repellents, self-tanners, solubilizers, perfume oils, dyes and the like.
Als Perlglanzwachse kommen beispielsweise in Frage: Alkylenglycolester, Fettsäurealkanolamide, Partialglyceride, Ester von mehrwertigen, gegebenenfalls hydroxysubstituierten Carbonsäuren, Fettalkohole, Fettsäuren, Fettketone, Fettaldehyde, Fettether, Fettcarbonate, Ringöffnungsprodukte von Olefinepoxiden sowie deren Mischungen.Suitable pearlescing waxes are, for example: alkylene glycol esters, fatty acid alkanolamides, partial glycerides, Esters of polybasic, optionally hydroxysubstituted carboxylic acids, fatty alcohols, Fatty acids, fatty ketones, fatty aldehydes, fatty ethers, fatty carbonates, ring-opening products of olefin epoxides as well as their mixtures.
Bei den Alkylenglycolestern, die die Komponente (a1) bilden, handelt es sich üblicherweise um Mono-
und/oder Diester von Alkylenglycolen, die der Formel (III) folgen,
Fettsäurealkanolamide, die als Perlglanzwachse der Gruppe (a2) in Frage kommen, folgen der Formel
(IV),
Partialglyceride, die über Perlglanzeigenschaften verfügen und die Komponente (a3) bilden, stellen Mono und/oder Diester des Glycerins mit linearen, gesättigten Fettsäuren, nämlich beispielsweise Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Behensäure sowie deren technische Mischungen dar. Sie folgen der Formel (V), in der R9CO für einen linearen, gesättigten Acylrest mit 6 bis 22 Kohlenstoffatomen, R10 und R11 unabhängig voneinander für Wasserstoff oder R9CO, x, y und z in Summe für 0 oder für Zahlen von 1 bis 30 und X für ein Alkali- oder Erdalkalimetall mit der Maßgabe steht, daß mindestens einer der beiden Reste R10 und R11 Wasserstoff darstellt. Typische Beispiele sind Laurinsäuremonoglycerid, Laurinsäurediglycerid, Kokosfettsäuremonoglycerid, Kokosfettsäuretriglycerid, Palmitinsäuremonoglycerid, Palmitinsäuretriglycerid, Stearinsäuremonoglycerid, Stearinsäurediglycerid, Talgfettsäuremonoglycerid, Talgfettsäurediglycerid, Behensäuremonoglycerid, Behensäurediglycerid sowie deren technische Gemische, die untergeordnet aus dem Herstellungsprozeß noch geringe Mengen an Triglycerid enthalten können. Partial glycerides having pearlescent properties and constituting component (a3) are mono and / or diesters of glycerol with linear, saturated fatty acids, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, behenic acid and their technical properties Mixtures. They follow the formula (V) , in the R 9 CO for a linear, saturated acyl radical having 6 to 22 carbon atoms, R 10 and R 11 are independently hydrogen or R 9 CO, x, y and z in total for 0 or for numbers from 1 to 30 and X for an alkali or alkaline earth metal with the proviso is that at least one of the two radicals R 10 and R 11 is hydrogen. Typical examples are lauric acid monoglyceride, lauric acid diglyceride, coconut fatty acid monoglyceride, coconut fatty acid triglyceride, palmitic acid monoglyceride, palmitic acid triglyceride, stearic acid monoglyceride, stearic acid diglyceride, tallow fatty acid monoglyceride, tallow fatty acid diglyceride, behenic acid monoglyceride, baryric acid diglyceride and their technical mixtures which, subordinated to the production process, may still contain small amounts of triglyceride.
Als Perlglanzwachse, die die Komponente (a4) bilden, kommen weiterhin Ester von mehrwertigen, gegebenenfalls polyfunktionellen, vorzugsweise hydroxysubstuierten Carbonsäuren mit Fettalkoholen mit 6 bis 22 Kohlenstoffatomen in Frage. Weiterhin kommen ebenfalls Metallsalze, insbesondere Alkalisalze, von Monoestem der Dicarbonsäuren bzw. von Mono- und/oder Diestem der Tricarbonsäuren in Frage. In einer besonderen Ausführungsform der Erfindung können als Komponente (a4) ebenfalls Ester von polyfunktionellen Carbonsäuren, vorzugsweise Hydroxycarbonsäuren mit Partialestem von Polyolen sowie die Metallsalze der entsprechenden Halbester eingesetzt werden. Als Säurekomponente dieser Ester kommen beispielsweise Malonsäure, Maleinsäure, Fumarsäure, Adipinsäure, Sebacinsäure, Azelainsäure, Dodecandisäure, Phthalsäure, Isophthalsäure und insbesondere Bernsteinsäure sowie Äpfelsäure, Citronensäure und insbesondere Weinsäure und deren Mischungen in Betracht. Die Fettalkohole enthalten 6 bis 22, vorzugsweise 12 bis 18 und insbesondere 16 bis 18 Kohlenstoffatome in der Alkylkette. Typische Beispiele sind Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, Isotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol und Brassidylalkohol sowie deren technische Mischungen. Die Ester können als Voll oder Partialester vorliegen, vorzugsweise werden Mono- und vor allem Diester der Carbon- bzw. Hydroxycarbonsäuren eingesetzt. Typische Beispiele sind Bemsteinsäuremono- und -dilauryl-ester, Bemsteinsäuremono- und -dicetearlyester, Bemsteinsäuremono- und -distearylester, Weinsäuremono- und - dilaurylester, Weinsäuremono- und dikokosalkylester, Weinsäuremono- und -dicetearyl-ester, Citronensäuremono-, -di- und -trilaurylester, Citronensäuremono-, -di- und -trikokosalkylester sowie Citronensäuremono-, -di- und -tricetearylester sowie deren Metallsalze, vorzugsweise Alkalisalze.As pearlescent waxes which form component (a4), esters of polyvalent, optionally also come polyfunctional, preferably hydroxy-substituted carboxylic acids with fatty alcohols with 6 to 22 carbon atoms in question. Furthermore, metal salts, in particular alkali salts, also come in, of monoesters of dicarboxylic acids or of mono- and / or diesters of tricarboxylic acids in Question. In a particular embodiment of the invention, as component (a4) as well Esters of polyfunctional carboxylic acids, preferably hydroxycarboxylic acids with partial esters of Polyols and the metal salts of the corresponding half esters can be used. As acid component Examples of these esters are malonic acid, maleic acid, fumaric acid, adipic acid, sebacic acid, Azelaic acid, dodecanedioic acid, phthalic acid, isophthalic acid and especially succinic acid and malic acid, citric acid and especially tartaric acid and mixtures thereof. The fatty alcohols contain from 6 to 22, preferably 12 to 18 and especially 16 to 18 carbon atoms in the alkyl chain. Typical examples are caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, Capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, Stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, Linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, Erucyl alcohol and brassidyl alcohol and their technical mixtures. The esters can be considered full or Partial esters are present, preferably mono- and especially diesters of carboxylic or hydroxycarboxylic acids used. Typical examples are succinic mono- and dilauryl esters, succinic acid mono- and dicetearly esters, succinic mono- and distearyl esters, tartaric mono- and dilauryl esters, tartaric and dicocoalkyl esters, tartaric and dicetearyl tartaric acid, citric acid mono-, di- and tri-lauryl esters, citric acid mono-, di- and tricocoalkyl esters and citric acid mono-, di- and tricetearyl esters and their metal salts, preferably alkali metal salts.
Als weitere Gruppe von Perlglanzwachsen (a5) können Fettalkohole und/oder Fettsäuren eingesetzt
werden, die der Formel (VI) folgen,
Fettketone, die als Komponente (a6) in Betracht kommen, folgen vorzugsweise der Formel (VII),
Als Perlglanzwachse geeignete Fettaldehyde (a7) entsprechen vorzugsweise der Formel (VIII),
Als Perlglanzwachse (a8) kommen femer Fettether vorzugsweise der Formel (IX) in Frage,
Als Komponente (a9) kommen weiterhin Fettcarbonate vorzugsweise der Formel (X) in Betracht,
Bei den Epoxidringöffnungsprodukten, die schließlich die Gruppe (a10) bilden, handelt es sich um bekannte Stoffe, die üblicherweise durch säurekatalysierte Umsetzung von endständigen oder innenständigen Olefinepoxiden mit aliphatischen Alkoholen hergestellt werden. Die Reaktionsprodukte folgen vorzugsweise der Formel (XI), in der R20 und R21 für Wasserstoff oder einen Alkylrest mit 10 bis 20 Kohlenstoffatomen steht, mit der Maßgabe, daß die Summe der Kohlenstoffatome von R20 und R21 im Bereich von 10 bis 20 liegt und R22 für einen Alkyl- und/oder Alkenylrest mit 12 bis 22 Kohlenstoffatomen und/oder den Rest eines Polyols mit 2 bis 15 Kohlenstoffatomen und 2 bis 10 Hydroxylgruppen steht. Typische Beispiele sind Ringöffnungsprodukte von α-Dodecenepoxid, α-Hexadecenepoxid, α-Octadecenepoxid, α-Eicosenepoxid, α-Docosenepoxid, i-Dodecenepoxid, i-Hexadecenepoxid, i-Octadecenepoxid, i-Eicosenepoxid und/ oder i-Docosenepoxid mit Laurylalkohol, Kokosfettalkohol, Myristylalkohol, Cetylalkohol, Cetearylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Behenylalkohol und/oder Erucylalkohol. Vorzugsweise werden Ringöffnungsprodukte von Hexa- und/oder Octadecenepoxiden mit Fettalkoholen mit 16 bis 18 Kohlenstoffatomen eingesetzt. Werden anstelle der Fettalkohole Polyole für die Ringöffnung eingesetzt, so handelt es sich beispielsweise um folgende Stoffe: Glycerin; Alkylenglycole, wie beispielsweise Ethylenglycol, Diethylenglycol, Propylenglycol, Butylenglycol, Hexylenglycol sowie Polyethylenglycole mit einem durchschnittlichen Molekulargewicht von 100 bis 1.000 Dalton; technische Oligoglyceringemische mit einem Eigenkondensationsgrad von 1,5 bis 10 wie etwa technische Diglyceringemische mit einem Diglyceringehalt von 40 bis 50 Gew.-%; Methyolverbindungen, wie insbesondere Trimethylolethan, Trimethylolpropan, Trimethylolbutan, Pentaerythrit und Dipentaerythrit; Niedrigalkylglucoside, insbesondere solche mit 1 bis 8 Kohlenstoffen im Alkylrest, wie beispielsweise Methyl- und Butylglucosid; Zuckeralkohole mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Sorbit oder Mannit, Zucker mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Glucose oder Saccharose; Aminozucker, wie beispielsweise Glucamin. Werden im Sinne des erfindungsgemäßen Verfahrens Perlglanzkonzentrate hergestellt, so liegt der Anteil der Perlglanzwachse an den Zubereitungen üblicherweise im Bereich von 5 bis 45, vorzugsweise 10 bis 45 und insbesondere 25 bis 35 Gew.-%, handelt es sich um Endformulierungen ist der Perlglanzgehalt natürlich wesentlich geringer und beträgt typischerweise 0,5 bis 3 und vorzugsweise 1 bis 2 Gew.-%.The epoxide ring opening products , which eventually form group (a10), are known materials commonly prepared by the acid-catalyzed reaction of terminal or internal olefin epoxides with aliphatic alcohols. The reaction products preferably follow the formula (XI), in which R 20 and R 21 are hydrogen or an alkyl radical having 10 to 20 carbon atoms, with the proviso that the sum of the carbon atoms of R 20 and R 21 is in the range of 10 to 20 and R 22 is an alkyl and / or or alkenyl radical having 12 to 22 carbon atoms and / or the radical of a polyol having 2 to 15 carbon atoms and 2 to 10 hydroxyl groups. Typical examples are ring opening products of α-dodecene epoxide, α-hexadecene epoxide, α-octadecene epoxide, α-eicosenepoxide, α-docosenepoxide, i-dodecenepoxide, i-hexadecene epoxide, i-octadecene epoxide, i-eicosenepoxide and / or i-docosenepoxide with lauryl alcohol, coconut fatty alcohol , Myristyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol and / or erucyl alcohol. Ring opening products of hexa- and / or octadecene epoxides with fatty alcohols containing 16 to 18 carbon atoms are preferably used. If polyols are used for the ring opening instead of the fatty alcohols, these are, for example, the following substances: glycerol; Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and polyethylene glycols having an average molecular weight of 100 to 1,000 daltons; technical oligoglycerine blends having an inherent degree of condensation of from 1.5 to 10 such as technical grade diglycerin blends having a diglycerol content of from 40 to 50 weight percent; Methylol compounds, in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; Niedrigalkylglucoside, in particular those having 1 to 8 carbons in the alkyl radical, such as methyl and Butylglucosid; Sugar alcohols having 5 to 12 carbon atoms, such as sorbitol or mannitol, sugars having 5 to 12 carbon atoms, such as glucose or sucrose; Amino sugars, such as glucamine. If pearlescent concentrates are prepared in the context of the process according to the invention, the proportion of pearlescent waxes in the preparations is usually in the range from 5 to 45, preferably 10 to 45 and in particular 25 to 35% by weight. The pearlescence content is, of course, essential in the case of end formulations less and is typically 0.5 to 3 and preferably 1 to 2 wt .-%.
Polyolester, die im Sinne der Erfindung zur Absenkung des Schmelzpunktes der Perlglanzwachse eingesetzt
werden, können ausgewählt sein aus den folgenden Gruppen von Verbindungen:
Typische Beispiele für geeignete Partialglyceride sind Hydroxystearinsäuremonoglycerid, Hydroxystearinsäurediglycerid, Isostearinsäuremonoglycerid, Isostearinsäurediglycerid, Ölsäuremonaglycerid, Ölsäurediglycerid, Ricinolsäuremoglycerid, Ricinolsäurediglycerid, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, Erucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, Äpfelsäurediglycerid sowie deren technische Gemische, die untergeordnet aus dem Herstellungsprozeß noch geringe Mengen an Triglycerid enthalten können. Ebenfalls geeignet sind Anlagerungsprodukte von 1 bis 30, vorzugsweise 5 bis 10 Mol Ethylenoxid an die genannten Partialglyceride.Typical examples of suitable partial glycerides are hydroxystearic hydroxystearic acid diglyceride, isostearic acid, Isostearinsäurediglycerid, Ölsäuremonaglycerid, oleic acid diglyceride, Ricinolsäuremoglycerid, Ricinolsäurediglycerid, Linolsäuremonoglycerid, Linolsäurediglycerid, Linolensäuremonoglycerid, Linolensäurediglycerid, Erucasäuremonoglycerid, Erucasäurediglycerid, Weinsäuremonoglycerid, Weinsäurediglycerid, Citronensäuremonoglycerid, Citronendiglycerid, Äpfelsäuremonoglycerid, malic acid diglyceride and technical mixtures thereof, which may contain minor amounts of triglyceride from the manufacturing process. Also suitable are addition products of 1 to 30, preferably 5 to 10 moles of ethylene oxide to said Partialglyceride.
Als Sorbitanester kommen Sorbitanmonoisostearat, Sorbitansesquiisostearat, Sorbitandiisostearat, Sorbitantriisostearat, Sorbitanmonooleat, Sorbitansesquioleat, Sorbitandioleat, Sorbitantrioleat, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesquitartrat, Sorbitanditartrat, Sorbitantritartrat, Sorbitanmonocitrat, Sorbitansesquicitrat, Sorbitandicitrat, Sorbitantricitrat, Sorbitanmonomaleat, Sorbitansesquimaleat, Sorbitandimaleat, Sorbitantrimaleat sowie deren technische Gemische. Ebenfalls geeignet sind Anlagerungsprodukte von 1 bis 30, vorzugsweise 5 bis 10 Mol Ethylenoxid an die genannten Sorbitanester.As sorbitan sorbitan, sorbitan sesquiisostearate, Sorbitan, sorbitan triisostearate, sorbitan monooleate, sorbitan, sorbitan, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, Sorbitandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat, Sorbitansesquitartrat, Sorbitanditartrat, Sorbitantritartrat come , Sorbitan monocitrate, sorbitan siccitrate, sorbitan di-citrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan adipate, sorbitan trimaleate, and technical mixtures thereof. Also suitable are addition products of 1 to 30, preferably 5 to 10 moles of ethylene oxide to said sorbitan esters.
Typische Beispiele für geeignete Polyglycerinester sind Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls® PGPH), Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate (Isolan® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) und Polyglyceryl Polyricinoleate (Admul® WOL 1403) Polyglyceryl Dimerate Isostearate sowie deren Gemische.Typical examples of suitable polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® GI 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan ® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl -3 distearates (Cremophor® GS 32) and polyglyceryl polyricinoleates (Admul® WOL 1403) polyglyceryl dimerate isostearates and mixtures thereof.
Beispiele für weitere geeignete Polyolester sind die gegebenenfalls mit 1 bis 30 Mol Ethylenoxid umgesetzten Mono-, Di- und Triester von Trimethylolpropan oder Pentaerythrit mit Laurinsäure, Kokosfettsäure, Talgfettsäure, Palmitinsäure, Stearinsäure, Ölsäure, Behensäure und dergleichen.Examples of other suitable polyol esters are the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, which are optionally reacted with from 1 to 30 mol of ethylene oxide.
Werden im Sinne des erfindungsgemäßen Verfahrens Perlglanzkonzentrate hergestellt, so liegt der Anteil der Polyolester an den Zubereitungen üblicherweise im Bereich von 0,5 bis 15, vorzugsweise 1 bis 10 und insbesondere 5 bis 8 Gew.-%, handelt es sich um Endformulierungen ist der Polyolestergehalt natürlich wesentlich geringer und beträgt typischerweise 0,1 bis 1 und vorzugsweise etwa 0,5 Gew.-%. Als Regel gilt, daß der Gehalt der Polyolester bezogen auf die Menge an Perlglanzwachs üblicherweise im Bereich von 1 bis 15 und vorzugsweise 5 bis 10 Gew.-% liegt.If pearlescent concentrates are produced in the context of the process according to the invention, then this is the case Proportion of polyol esters in the preparations usually in the range of 0.5 to 15, preferably 1 to 10 and in particular 5 to 8 wt .-%, it is final formulations is the polyolester content Of course, much less and is typically 0.1 to 1, and preferably about 0.5 Wt .-%. As a rule, the content of the polyol ester based on the amount of pearlescent wax is usually in the range of 1 to 15 and preferably 5 to 10 wt .-%.
Wie schon ausgeführt, können die tensidischen Zubereitungen grundsätzlich alle Typen von Tensiden
enthalten; deren Auswahl richtet sich allein nach dem gewünschten Anwendungsprofil für den Endverbrauch.
In einer bevorzugten Ausführungsform der Erfindung handelt es sich bei den tendischen Zubereitungen
jedoch um Perlglanzkonzentrate, also Zwischenprodukte. Hier ist die Auswahl der Tensidkomponente
kritischer, da das anwendungstechnische Anforderungsprofil primär darin besteht, möglichst
hohe Mengen des Perlglanzwachses dauerhaft zu stabilisieren und die Viskosität der Mittel dabei
so niedrig zu halten, daß sie noch problemlos gepumpt und dosiert werden können. Für diesen Zweck
kommen beispielsweise nichtionogene Tenside aus mindestens einer der folgenden Gruppen in Frage:
Die Anlagerungsprodukte von Ethylenoxid und/oder von Propylenoxid an Fettalkohole, Fettsäuren, Alkylphenole oder an Ricinusöl stellen bekannte, im Handel erhältliche Produkte dar. Es handelt sich dabei um Homologengemische, deren mittlerer Alkoxylierungsgrad dem Verhältnis der Stoffmengen von Ethylenoxid und/ oder Propylenoxid und Substrat, mit denen die Anlagerungsreaktion durchgeführt wird, entspricht. C12/18-Fettsäuremono- und -diester von Anlagerungsprodukten von Ethylenoxid an Glycerin sind aus DE 2024051 PS als Rückfettungsmittel für kosmetische Zubereitungen bekannt. C8/18-Alkylmono- und -oligoglycoside, ihre Herstellung und ihre Verwendung sind aus dem Stand der Technik bekannt. Ihre Herstellung erfolgt insbesondere durch Umsetzung von Glucose oder Oligosacchariden mit primären Alkoholen mit 8 bis 18 C-Atomen. Bezüglich des Glycosidrestes gilt, daß sowohl Monoglycoside, bei denen ein cyclischer Zuckerrest glycosidisch an den Fettalkohol gebunden ist, als auch oligomere Glycoside mit einem Oligomerisationsgrad bis vorzugsweise etwa 8 geeignet sind. Der Oligomerisierungsgrad ist dabei ein statistischer Mittelwert, dem eine für solche technischen Produkte übliche Homologenverteilung zugrunde liegt.The addition products of ethylene oxide and / or of propylene oxide to fatty alcohols, fatty acids, alkylphenols or castor oil are known, commercially available products. These are mixtures of homologues whose mean degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate, with which the addition reaction is carried out corresponds. C 12/18 fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations. C 8/18 alkyl mono- and oligoglycosides, their preparation and their use are known in the art. They are prepared in particular by reacting glucose or oligosaccharides with primary alcohols having 8 to 18 carbon atoms. With regard to the glycoside radical, both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable. The degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
Weiterhin können als Emulgatoren zwitterionische Tenside verwendet werden. Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine Carboxylat- und eine Sulfonatgruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosalkyldimethylammoniumglycinat, N-Acylaminopropyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyldimethylammoniumglycinat, und 2-Alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. Besonders bevorzugt ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fettsäureamid-Derivat. Ebenfalls geeignete Emulgatoren sind ampholytische Tenside. Unter ampholytischen Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer C8/18-Alkyl- oder -Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -COOH- oder -SO3H-Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N-Alkylpropionsäuren, N-Alkylaminobuttersäuren, N-Alkyliminodipropionsäuren, N-Hydroxyethyl-N-alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarcosine, 2-Alkylaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe. Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkylaminopropionat, das Kokosacylaminoethylaminopropionat und das C12/18-Acylsarcosin.Furthermore, zwitterionic surfactants can be used as emulsifiers. Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammoniumglycinate, for example Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacylaminopropyldimethylammoniumglycinat, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline each having 8 to 18 carbon atoms in the alkyl or acyl group and the Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. Particularly preferred is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine . Also suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are understood as meaning those surface-active compounds which, apart from a C 8/18 -alkyl or -acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C Atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12/18 acylsarcosine.
Schließlich kommen auch Kationtenside als Emulgatoren in Betracht, wobei solche vom Typ der Esterquats, vorzugsweise methylquatemierte Difettsäuretriethanolaminester-Salze, besonders bevorzugt sind.Finally, cationic surfactants are also suitable as emulsifiers, those of the type of Esterquats, preferably methyl-quaternized difatty acid triethanolamine ester salts, more preferably are.
Werden hochkonzentrierte Perlglanzkonzentrate hergestellt, kann es vorteilhaft sein, zur Erniedrigung
der Viskosität Polyole mitzuverwenden. Polyole, die hier in Betracht kommen, besitzen vorzugsweise 2
bis 15 Kohlenstoffatome und mindestens zwei Hydroxylgruppen. Die Polyole können noch weitere
funktionelle Gruppen, insbesondere Aminogruppen, enthalten bzw. mit Stickstoff modifiziert sein. Typische
Beispiele sind
Die Einsatzmenge der Polyole liegt - bezogen auf die tensidischen Zubereitungen - typischerweise im Bereich von 0,1 bis 15 und vorzugsweise 0,5 bis 5 Gew.-%. Werden höhere Polyolmengen, vorzugsweise Glycerin oder Ethylenglycol eingesetzt, werden die Konzentrate gleichzeitig gegen mikrobiellen Befall stabilisiert.The amount used of the polyols is - based on the surfactant preparations - typically in Range of 0.1 to 15 and preferably 0.5 to 5 wt .-%. Be higher amounts of polyol, preferably Glycerol or ethylene glycol used, the concentrates are simultaneously against microbial Infestation stabilized.
Üblicherweise erfolgt die Herstellung der tensidischen Zubereitungen, indem man eine wäßrige Tensid- bzw. Emulgatorlösung, gegebenenfalls zusammen mit weiteren Hilfs- und Zusatzstoffen bei 10 bis 25 °C vorlegt, und die Mischung aus Perlglanzwachs und Polyolester bei dieser Temperatur einträgt, homogenisiert und auskristallisieren läßt. Femer ist es möglich, eine konzentrierte wäßrige (Anion)-Tensidpaste vorzulegen, die Mischung aus Perlglanzwachs und Polyolester in der Kälte einzurühren und die Mischung anschließend mit weiterem Wasser auf die gewünschte Konzentration zu verdünnen oder das Vermischen in Gegenwart polymerer hydrophiler Verdickungsmittel, wie etwa Hydroxypropylcellulosen, Xanthan Gum oder Polymeren vom Carbomer-Typ durchzuführen. Schließlich kann die Mischung aus Perlglanzwachs und Polyolester auch schon in einer Teilmenge der wäßrigen Tensidlösung gelöst bzw. dispergiert sein und so mit der Hauptmenge der Zubereitung vermischt werden. The preparation of the surface-active preparations is usually carried out by reacting an aqueous surfactant or emulsifier solution, optionally together with other auxiliaries and additives at 10 to 25 ° C, and the mixture of pearlescent wax and polyol ester enters at this temperature, homogenized and crystallize. Furthermore, it is possible to use a concentrated aqueous (anion) surfactant paste to apply the mixture of pearlescent wax and polyol ester in the cold stir and then diluting the mixture with further water to the desired concentration or mixing in the presence of polymeric hydrophilic thickeners, such as hydroxypropylcelluloses, Xanthan gum or carbomer-type polymers. Finally, the Blend of pearlescent wax and polyol ester even in a subset of the aqueous surfactant solution be dissolved or dispersed and so mixed with the bulk of the preparation.
Der schmelzpunktsemiedrigende Effekt durch den Zusatz von Polyolestern zu handelsüblichen Perlglanzwachsen
wird in Tabelle 1 dargestellt. Verglichen wurden die reinen Wachse und Mischungen aus
90 Gew.-% Wachs und 10 Gew.-% Polyolester. Anschließend wurden Shampoos folgender Zusammensetzung
hergestellt: 12 g Kokosfettalkohol+2EO-sulfat-Natriumsalz, 1,5 g Dimethylpolysiloxan, 3 g
Kokosalkylglucosid und 1,5 g eines Esterquats (Wasser ad 100 Gew.-%). Die Zubereitungen wurden
(a) auf 90 °C erwärmt und mit jeweils 1 g der Perlglanzwachse V1 bis V4 versetzt und innerhalb von 1
h auf Umgebungstemperatur abgekühlt bzw. (b) bei 20 °C mit 1 g der Mischungen 1 bis 4 versetzt.
enthielten. Die Feinteiligkeit der Perlglanzkristalle in den Haarshampoos wurde unter dem Mikroskop
visuell auf einer Skala von 1 = sehr feine Kristalle bis 5 = grobe Kristalle beurteilt. Die Beurteilung des
Perlglanzes erfolgte ebenfalls auf einer Skala von 1 = brillant bis 5 = stumpf. Die Ergebnisse sind
ebenfalls in Tabelle 1 enthalten.
Claims (10)
- A process for the cold production of pearlizing surfactant preparations in which aqueous surfactant solutions are initially introduced and mixtures of pearlizing waxes and polyol esters are stirred in at temperatures of 10 to 45°C.
- A process as claimed in claim 1, characterized in that intermediate products or end formulations for the consumer are produced.
- A process as claimed in claims 1 and/or 2, characterized in that solutions of anionic, nonionic, cationic, amphoteric and/or zwitterionic surfactants are used.
- A process as claimed in at least one of claims 1 to 3, characterized in that the surfactants are used in quantities - based on the preparations-of 1 to 25% by weight (end formulation) or 15 to 40% by weight (concentrate).
- A process as claimed in at least one of claims 1 to 4, characterized in that pearlizing waxes selected from the group consisting of alkylene glycol esters, fatty acid alkanolamides, partial glycerides, esters of polybasic, optionally hydroxysubstituted carboxylic acids, fatty alcohols, fatty acids, fatty ketones, fatty aldehydes, fatty ethers, fatty carbonates, ring opening products of olefin epoxides and mixtures thereof are used.
- A process as claimed in at least one of claims 1 to 5, characterized in that the pearlizing waxes are used in quantities - based on the surfactant-containing preparations - of 0.5 to 3% by weight (end formulation) or 5 to 45% by weight (concentrate).
- A process as claimed in at least one of claims 1 to 5, characterized in that polyolesters selected from the group consisting of partial esters of glycerol and/or sorbitan with saturated and/or unsaturated, linear or branched fatty acids containing 12 to 22 carbon atoms and/or hydroxycarboxylic acids containing 3 to 18 carbon atoms and adducts thereof with 1 to 30 mol ethylene oxide; partial esters of polyglycerol, polyethylene glycol, trimethylolpropane, pentaerythritol, alkyl glucosides and polyglucosides with saturated and/or unsaturated, linear or branched fatty acids containing 12 to 22 carbon atoms and/or hydroxycarboxylic acids containing 3 to 18 carbon atoms and adducts thereof with 1 to 30 mol ethylene oxide; mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol and/or mixed esters of fatty acids containing 6 to 22 carbon atoms, methyl glucose and polyols and mixtures thereof are used.
- A process as claimed in at least one of claims 1 to 7, characterized in that the polyol esters are used in quantities - based on the surfactant-containing preparations - of 0.1 to 1% by weight (end formulation) or 0.5 to 15% by weight (concentrate).
- A process as claimed in at least one of claims 1 to 8, characterized in that emulsifiers selected from the group consisting of products of the addition of 2 to 30 mol ethylene oxide and/or 0 to 5 mol propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 12 to 22 carbon atoms, onto alkylphenols containing 8 to 15 carbon atoms in the alkyl group and onto alkylamines containing 8 to 22 carbon atoms in the alkyl group; alkyl mono- and oligoglycosides containing 8 to 22 carbon atoms in the alkyl group and ethoxylated analogs thereof; products of the addition of 1 to 15 or 15 to 60 mol ethylene oxide onto castor oil and/or hydrogenated castor oil; mono-, di- and trialkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and salts thereof; wool wax alcohols; polysiloxane/polyalkyl polyether copolymers and corresponding derivatives; polyalkylene glycols, glycerol carbonate, Cocamidopropylbetaines and/or esterquats are used for the production of concentrated surfactant-containing preparations.
- A process as claimed in at least one of claims 1 to 9, characterized in that polyols are also used for the production of concentrated surfactant-containing preparations.
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DE19921187 | 1999-05-07 | ||
DE19921187A DE19921187C2 (en) | 1999-05-07 | 1999-05-07 | Process for the cold production of pearlescent surfactant preparations |
PCT/EP2000/003853 WO2000068355A1 (en) | 1999-05-07 | 2000-04-28 | Cold production method for pearly lustre surfactant preparations |
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JP (1) | JP2004506592A (en) |
DE (2) | DE19921187C2 (en) |
ES (1) | ES2245310T3 (en) |
WO (1) | WO2000068355A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102015213478A1 (en) | 2015-07-17 | 2017-01-19 | Henkel Ag & Co. Kgaa | stabilizing mixture |
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DE19937298A1 (en) * | 1999-08-06 | 2001-02-22 | Cognis Deutschland Gmbh | Aqueous pearlescent concentrates |
DE10025671B4 (en) * | 2000-05-24 | 2006-07-27 | Cognis Ip Management Gmbh | emulsifiers |
DE10162026A1 (en) * | 2001-12-18 | 2003-07-03 | Cognis Deutschland Gmbh | Highly concentrated flowable pearlescent concentrates |
US7923425B2 (en) * | 2006-08-21 | 2011-04-12 | Henkel Ag & Co. Kgaa | Low-foaming, acidic low-temperature cleaner and process for cleaning surfaces |
JP2008150308A (en) * | 2006-12-15 | 2008-07-03 | Mitsui Fine Chemicals Inc | Hair modifier, hair cosmetic comprising hair modifier ingredient and method for modifying hair |
US8529788B2 (en) * | 2007-03-12 | 2013-09-10 | Kao Corporation | Pearlescent composition |
BR112012004297A2 (en) | 2009-08-27 | 2017-05-30 | Otc Gmbh | pearlescent concentrate and method for its manufacture. |
DE102009040454A1 (en) | 2009-08-27 | 2011-03-24 | Otc Verwaltungs Gmbh | Continuous production of pearlescent dispersion made of pearlescer and dispersant, comprises e.g. dosing a flowable stream made by pre-heating two phases of the pearlescent dispersion into mixing vessel |
EP2723343A2 (en) | 2011-06-23 | 2014-04-30 | The Procter and Gamble Company | Process of forming crystals for use in a personal care composition |
US10813862B2 (en) | 2012-05-30 | 2020-10-27 | Clariant International Ltd. | Use of N-methyl-N-acylglucamines as solubilizers |
US10864275B2 (en) | 2012-05-30 | 2020-12-15 | Clariant International Ltd. | N-methyl-N-acylglucamine-containing composition |
DE102012021647A1 (en) | 2012-11-03 | 2014-05-08 | Clariant International Ltd. | Aqueous adjuvant compositions |
BR112015032536A2 (en) * | 2013-06-28 | 2017-07-25 | Clariant Int Ltd | use of special n-methyl-n-acylglucamines in skin cleansing agents and hand dishwashing agents |
US9833395B2 (en) * | 2013-10-25 | 2017-12-05 | Galaxy Surfactants Ltd. | Sustainable cold-dispersible pearlescent concentrate |
DE102014005771A1 (en) | 2014-04-23 | 2015-10-29 | Clariant International Ltd. | Use of aqueous drift-reducing compositions |
DE102015219608B4 (en) | 2015-10-09 | 2018-05-03 | Clariant International Ltd | Universal pigment dispersions based on N-alkylglucamines |
DE102015219651A1 (en) | 2015-10-09 | 2017-04-13 | Clariant International Ltd. | Compositions containing sugar amine and fatty acid |
DE202016003070U1 (en) | 2016-05-09 | 2016-06-07 | Clariant International Ltd. | Stabilizers for silicate paints |
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DE1165574B (en) | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Process for the production of mixed esters used as emulsifiers for ointment bases |
DE2024051C3 (en) | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Use of the esterification products of glycerol-ethylene oxide adducts with fatty acids as refatting agents in cosmetic preparations |
CA1261276A (en) | 1984-11-09 | 1989-09-26 | Mark B. Grote | Shampoo compositions |
JPS61268797A (en) | 1985-05-23 | 1986-11-28 | ライオン株式会社 | Production of high concentration pearl like gloss dispersion |
DE3519080A1 (en) | 1985-05-28 | 1986-12-04 | Henkel Kgaa | FLOWABLE Pearlescent Concentrate |
JPH0699275B2 (en) * | 1985-11-05 | 1994-12-07 | 株式会社コーセー | Non-water cleansing fee |
EP0285389B1 (en) | 1987-04-01 | 1992-09-23 | The Procter & Gamble Company | Shampoo compositions |
US5711899A (en) | 1988-12-23 | 1998-01-27 | Henkel Kommanditgesellschaft Auf Aktien | Free flowing pearlescent concentrate |
DE3843572A1 (en) * | 1988-12-23 | 1990-06-28 | Henkel Kgaa | FLOWABLE Pearlescent Concentrate |
DE4103551A1 (en) * | 1991-02-06 | 1992-08-13 | Henkel Kgaa | FLOWABLE PEARL CONCENTRATE |
ATE130362T1 (en) | 1992-05-13 | 1995-12-15 | Hoechst Ag | NON-IONIC, FLOWING PEARLIGHT DISPERSIONS. |
DE4224715A1 (en) | 1992-07-27 | 1994-02-03 | Hoechst Ag | Flowable preservative-free pearlescent dispersions |
JPH0782140A (en) * | 1993-09-14 | 1995-03-28 | Kao Corp | Liquid detergent composition having pearl gloss |
ES2141862T3 (en) * | 1994-05-28 | 2000-04-01 | Goldschmidt Ag Th | AQUAUS CONCENTRATES FLUIDS OF PEARL LUSTER. |
DE4420516C2 (en) * | 1994-06-13 | 1998-10-22 | Henkel Kgaa | Polyglycerol polyhydroxystearates |
US5612655A (en) * | 1995-07-06 | 1997-03-18 | Allen Telecom Group, Inc. | Filter assembly comprising a plastic resonator support and resonator tuning assembly |
DE19527120A1 (en) * | 1995-07-25 | 1997-01-30 | Henkel Kgaa | Flowable pearlescent concentrate |
DE19619645A1 (en) * | 1996-05-15 | 1997-11-20 | Henkel Kgaa | Hair treatment products |
DE19622968C2 (en) * | 1996-06-07 | 2000-08-17 | Cognis Deutschland Gmbh | Aqueous pearlescent concentrates |
DE19622967C1 (en) * | 1996-06-07 | 1998-01-29 | Henkel Kgaa | Aqueous pearlescent concentrates |
DE19641280C2 (en) * | 1996-10-07 | 1999-09-16 | Henkel Kgaa | Use of monoglyceride (ether) sulfates as pearlescent waxes |
DE19646869C1 (en) * | 1996-11-13 | 1997-12-04 | Henkel Kgaa | Cosmetic formulation containing cationic polymer, especially pearly shampoo, giving stable aqueous formulation |
DE19646867C1 (en) * | 1996-11-13 | 1997-12-04 | Henkel Kgaa | Cosmetic formulation containing silicone compound, especially pearly shampoo, giving stable aqueous formulation |
DE19650473C1 (en) * | 1996-12-05 | 1998-04-02 | Henkel Kgaa | Instant sun tan lotion formulations containing di:hydroxy:acetone |
JPH10182343A (en) * | 1996-12-25 | 1998-07-07 | Kao Corp | Iridescent composition and its production |
GB9711685D0 (en) * | 1997-06-05 | 1997-08-06 | Procter & Gamble | Cosmetic compositions |
-
1999
- 1999-05-07 DE DE19921187A patent/DE19921187C2/en not_active Expired - Fee Related
-
2000
- 2000-04-28 EP EP00929458A patent/EP1177274B8/en not_active Expired - Lifetime
- 2000-04-28 WO PCT/EP2000/003853 patent/WO2000068355A1/en active IP Right Grant
- 2000-04-28 US US10/009,289 patent/US6727217B1/en not_active Expired - Fee Related
- 2000-04-28 DE DE50010521T patent/DE50010521D1/en not_active Expired - Fee Related
- 2000-04-28 JP JP2000616323A patent/JP2004506592A/en active Pending
- 2000-04-28 ES ES00929458T patent/ES2245310T3/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102015213478A1 (en) | 2015-07-17 | 2017-01-19 | Henkel Ag & Co. Kgaa | stabilizing mixture |
WO2017012727A1 (en) | 2015-07-17 | 2017-01-26 | Henkel Ag & Co. Kgaa | Stabilizing mixture |
Also Published As
Publication number | Publication date |
---|---|
US6727217B1 (en) | 2004-04-27 |
DE19921187A1 (en) | 2000-11-16 |
JP2004506592A (en) | 2004-03-04 |
DE50010521D1 (en) | 2005-07-14 |
EP1177274B8 (en) | 2005-08-03 |
WO2000068355A1 (en) | 2000-11-16 |
EP1177274A1 (en) | 2002-02-06 |
ES2245310T3 (en) | 2006-01-01 |
DE19921187C2 (en) | 2001-06-28 |
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