DE2703185A1 - Cosmetics contg. hydroxyalkyl-urea derivs. - useful as skin moisture regulators - Google Patents

Cosmetics contg. hydroxyalkyl-urea derivs. - useful as skin moisture regulators

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Publication number
DE2703185A1
DE2703185A1 DE19772703185 DE2703185A DE2703185A1 DE 2703185 A1 DE2703185 A1 DE 2703185A1 DE 19772703185 DE19772703185 DE 19772703185 DE 2703185 A DE2703185 A DE 2703185A DE 2703185 A1 DE2703185 A1 DE 2703185A1
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Prior art keywords
hydroxyalkyl
urea
skin
weight
substituted
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DE19772703185
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German (de)
Inventor
Hinrich Dipl Chem Dr Moeller
Rainer Dipl Chem Dr Osberghaus
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to DE19772703185 priority Critical patent/DE2703185A1/en
Publication of DE2703185A1 publication Critical patent/DE2703185A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0212—Face masks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Abstract

Cosmetics, esp. for skin care, contain 1-20 (pref. 3-10) wt.% of a hydroxyalkyl-urea deriv. of formula (I): R1R2N-CO-NR3R4 (where R1-R4 are H, 1-4C alkyl or 2-6C hydroxyalkyl (contg. 1-5 OH gps), provided that >=1 is hydroxyalkyl). (I) are pref. prepd. by reacting opt. substd. 2-oxazaolidones with sec. or esp. primary amines at high temp. (esp. 100-200 degrees C). (I) act as skin moisture regulators which, unlike conventional acids and salts, do not affect the stability of low-viscosity o/w emulsions used as cosmetic bases.

Description

Kosmetische Mittel mit einem Gehalt an Haut-FeuchthaltemittelnCosmetic preparations containing skin moisturizers

Die Erfindung betrifft kosmetische Mittel, insbesondere Hautpflege-, Hautschutz-, und Hautreinigungsmittel mit einem Gehalt an hydroxyalkyl substituierten Harnstoffen als Haut-Feuchthaltemittel.The invention relates to cosmetic agents, in particular skin care, Substituted skin protection and skin cleansing agents containing hydroxyalkyl Urea as a skin moisturizer.

Es ist allgemein bekannt, daß zu den Schutzmaßnahmen der gesunden Haut neben anderen Faktoren eine gewisse Hygroskopizität gehört. Werden die Substanzen, auf denen dieso Hygroskopizität sowie ihre laufende Wiederherstellung beruhen, der Ilaut durch Umwelteinflüsse, wie wiederholtes Waschen mit stark netzenden und extrahierenden Stoffen, Chemikalieneinflüsse, starke Witteruneseinflüsse, entzogen, so treten Veränderungen in der Hornschicht auf, durch die die Schutzwirkung der Haut gegen schädigende Umwelteinflüsse stark herabgesetzt werden kann.It is common knowledge that to protect the healthy Skin, among other factors, has a certain hygroscopicity. Will the substances on which this hygroscopicity and its ongoing restoration are based Ilaut by environmental influences, such as repeated washing with strong wetting and extracting agents Substances, chemical influences, strong weather conditions, withdrawn, that's how changes occur in the horny layer, through which the protective effect of the skin against harmful environmental influences can be greatly reduced.

Es bestand daher die Aufgabe, kosmetische Mittel,insbesondere Hautpflege-, Hautschutz- und Hautreinigungsmittel zu entwickeln, durch die die Funktionsfahigkeit der Haut trotz schädigender Umwelteinflüsse voll bzw. in verstärktem Maße erhalten bleibt und im Falle einer eingetretenen Schädigung die Wiederherstellung der Hornhaut wirkungsvoll unterstützt wird.It was therefore the task of cosmetic agents, in particular skin care, Develop skin protection and skin cleansing agents through which the functionality of the skin fully or to a greater extent despite damaging environmental influences remains and, in the event of damage, the restoration of the cornea is effectively supported.

Bei den bisher als Ilaut-Feuchthaltemittel eingesetzten Produkten handelte es sich durchweg um ionische Verbindungen wie Säuren und in erster Linie Salze, die zwar in manchen Fällen brauchbare ] rgebnisse als Hautfeuchtigkeitsregulatoren lieferten, jedoch die Stabilität insbesondere dünnflüssiger O/W-Emulsionen erheblich herabsetzen. In solchen Fällen konnten vielfach nur völlig unzureichende Mengen an Hautfeuchtigkeitsregulatoren eingearbeitet werden. Neben der allgemeinen Aufgabe zur Entwicklung guter Haut-Feuchthaltemittel galt das besondere Interesse solchen Produkten, die keine Stabilitätsprobleme nach der Einarbeitung insbesondere auch in O/W-Emulsionen bereiten.In the products previously used as Ilaut humectants were all ionic compounds such as acids and primarily Salts, which in some cases have useful results as skin moisture regulators delivered, however, considerably reduce the stability of low-viscosity O / W emulsions in particular. In such cases, in many cases only completely inadequate amounts of skin moisture regulators could be used be incorporated. In addition to the general task of developing good skin moisturizers The special interest was given to products that do not have any stability problems prepare for incorporation, especially in O / W emulsions.

Diese Aufgabe wurde dadurch gelöst, daß man kosmetische Mittel, insbesondere Hautpilege-, Hautschutz- und Hautreinigungsmittel auf Basis üblicher Bestandteile wie Tenside, Emulgatoren, Fettsubstanzen, Pflanzenauszüge, Lösungsmittel, Duftstoffe, Verdickungs-, Konservierungsmittel verwendet mit einem Gehalt an hydroxyalkylsubstituierten Harnstoffen der allgemeinen Formel in der R1, R2, R3 und 114 unabhängig voneinander für ein Wasserstoffatom, eine niedere (C1-C4)-Alkyl- oder eine niedere (C2-C6)-Hydroxyalkylgruppe, die 1 - 5 Hydroxyl-bzw. Hydroxyalkylgruppen enthalten kann, stehen, mit der Maßgabe, daß wenigstens einer der Reste R1 114 eine Hydroxyalkyl- oder Oligohydroxyalicylgruppe darstellt, in einer Menge von 1 bis 20 Gewichtsprozent, vorzugsweise 3 bis 10 Gewichtsprozent, bezogen auf das gesamte Mittel, Diese erfindungsgemäß einzusetzenden Produkte sind in vorzüglicher Weise geeignet, die Wasserretention der Haut aufrechtzuerhalten bzw. wiederherzustellen und hierdurch die Haut weich und flexibel und voll funktionsfähig zu halten.This object was achieved by using cosmetic agents, in particular skin care agents, skin protection agents and skin cleansing agents based on conventional ingredients such as surfactants, emulsifiers, fatty substances, plant extracts, solvents, fragrances, thickeners and preservatives with a content of hydroxyalkyl-substituted ureas of the general formula in which R1, R2, R3 and 114 independently represent a hydrogen atom, a lower (C1-C4) -alkyl or a lower (C2-C6) -hydroxyalkyl group, the 1-5 hydroxyl or. May contain hydroxyalkyl groups, with the proviso that at least one of the radicals R1 114 represents a hydroxyalkyl or oligohydroxyalicyl group, in an amount of 1 to 20 percent by weight, preferably 3 to 10 percent by weight, based on the total agent, These are products to be used according to the invention excellently suited to maintaining or restoring the water retention of the skin and thereby keeping the skin soft, flexible and fully functional.

Die Herstellung der erfindungsgemäß als Haut-Feuchthaltemittel zu verwenclenden Verbindungen kann nach allgemein bekannten Verfahren erfolgen. So können sie zum Beispiel durch Reaktion von substituierten primären oder sekundären Aminen mit Harnstoff bei höheren Temperaturen von etwa 80 bis 2000C oder durch Reaktion der substituierten Aminhydrochioride mit Alkalicyanaten im wäßrigen Milieu erhalten werden. Auch Reaktionen von Carbamidsäureestern, die am Stickstoff substituiert sein können, mit gegebenenfalls substituierten primären oder sekundären Aminen, liefern die entsprechenden hydroxyalkylsubstituierten Harnstoffe. Auch durch Reaktion mit Isocyanaten, Carbamoylchloriden oder Phosgen können aus entsprechend substituierten Aminen die erfindungsgemäß einzusetzenden hydroxyalkylsubstituierten Harnstoffe hergestellt werden.The production of the invention as skin moisturizers too Compounds used can be made by generally known methods. So they can, for example, by reacting substituted primary or secondary Amines with urea at higher temperatures of about 80 to 2000C or by reaction obtained the substituted amine hydrochloride with alkali metal cyanates in an aqueous medium will. Also reactions of carbamic acid esters substituted on nitrogen can be, with optionally substituted primary or secondary amines, provide the corresponding hydroxyalkyl-substituted ureas. Also through reaction with isocyanates, carbamoyl chlorides or phosgene can be appropriately substituted Amines, the hydroxyalkyl-substituted ureas to be used according to the invention getting produced.

Es wurde ferner gefunden, daß sich N-(2-Hydroxyalkyl)-harn stoffe auf einfache Weise dadurch herstellen lassen, daß man gegebenenfalls substituierte 2-Oxazolidone bei erhöhter Temperatur zwischen vorzugsweise 100 bis 2000C mit primären oder sekundären, insbesondere primären Aminen reagieren läßt.It was also found that N- (2-hydroxyalkyl) urine materials can be prepared in a simple manner by optionally substituted 2-Oxazolidone at an elevated temperature between preferably 100 to 2000C with primary or secondary, especially primary amines can react.

Die Reaktion verläuft dabei nach folgendem Schema: Erfindungsgemäß einzusetzende hydroxyalkylsubstituierte Harnstoffe sind zum Beispiel N-(2-Hydroxyäthyl)-; N-(9-Hydroxypropyl)-; N-(3-Hydroxypropyl)-; N-(2,3-Dihydroxypropyl)-; N-(2,3,4,5,6-Pentahydroxyhexyl)-; N-Methyl-N-(1,3,4,5,6-pentahydroxy-2-hexyl)-; N-Methyl-N'-(1-hydroxy-2-methyl-2-propyl)-; N-(1-Hydroxy-2-methyl-2-propyl)-; N-(1,3-Dihydroxy-2-propyl)-; N-(Tris-hydroxymethyl-methyl)-; N-Äthyl-N'-(2-hydroxyäthyl)-; N,N-Bis-(2-hydroyxäthyl)-; N,N'-Bis-(2-hydroxyäthyl)-; N,N-Bis-(2-hydroxypropyl)-; N,N'-Bis-(2-hydroxypropyl)-; N,N-Bis-(2-hydroxyäthyl)-N'-propyl-; N,N-Bis-(2-hydroxypropyl)-N'-(2-hydroxyäthyl)-; N-tert.Butyl-N'-(2-hydroxyäthyl)-N'-(2-hydroyxpropyl)-; N-(1,3-Dihydroxy-2-propyl)-N'-(2-hydroxyäthyl)-; N,N-Bis-(2-hydroxyäthyl)-N',N'-dimethyl-; N,N,N',N'-Tetrakis-(2-hydroxyäthyl)-; N,N-Bis-(2-hydroxyäthyl)-N',N'-bis-(2-hydroxypropyl)-harnstoff.The reaction proceeds according to the following scheme: Hydroxyalkyl-substituted ureas to be used according to the invention are, for example, N- (2-hydroxyethyl) -; N- (9-hydroxypropyl) -; N- (3-hydroxypropyl) -; N- (2,3-dihydroxypropyl) -; N- (2,3,4,5,6-pentahydroxyhexyl) -; N-methyl-N- (1,3,4,5,6-pentahydroxy-2-hexyl) -; N-methyl-N '- (1-hydroxy-2-methyl-2-propyl) -; N- (1-hydroxy-2-methyl-2-propyl) -; N- (1,3-dihydroxy-2-propyl) -; N- (tris-hydroxymethyl-methyl) -; N-ethyl-N '- (2-hydroxyethyl) -; N, N-bis (2-hydroxyethyl) -; N, N'-bis (2-hydroxyethyl) -; N, N-bis (2-hydroxypropyl) -; N, N'-bis (2-hydroxypropyl) -; N, N-bis (2-hydroxyethyl) -N'-propyl-; N, N-bis (2-hydroxypropyl) -N '- (2-hydroxyethyl) -; N-tert-butyl-N '- (2-hydroxyethyl) -N' - (2-hydroxpropyl) -; N- (1,3-dihydroxy-2-propyl) -N '- (2-hydroxyethyl) -; N, N-bis (2-hydroxyethyl) -N ', N'-dimethyl-; N, N, N ', N'-tetrakis (2-hydroxyethyl) -; N, N-bis (2-hydroxyethyl) -N ', N'-bis (2-hydroxypropyl) urea.

Die erfindungsgemäß einzusetzenden hydroxyalkyl substi tuiort;en Harnstoffe stellen farblose, kristalline oder viskose völlig stabile Produkte dar, die eine sehr gute physiologische Verträglichkeit besitzen und sich als neutrale, nichtionische Verbindungen durch eine besonders gute Einarbeitbarkeit in kosmetische Emulsionsgrundlagen auszeichnen.The hydroxyalkyl substituted ureas to be used according to the invention represent colorless, crystalline or viscous completely stable products, the one have very good physiological compatibility and prove to be neutral, non-ionic Compounds thanks to their particularly easy incorporation into cosmetic emulsion bases distinguish.

Für die Einarbeitung in kosmetische Produkte können auch Mischungen verschiedener hydroxyalkyk substituierter Harnstoffe sowie Mischungen mit unsubstituiertem Harnstoff verwendet erden. Es ist ferner nicht unbedingt erforderlich, die reinen Verbindungen herzustellen, sondern es können auch die Rohprodukte der Reaktion eingesetzt werden, wenn man sie durch Behandlung mit einem sauren Kationenaustauscher auf einen neutralen pH-Wert einstellt.Mixtures can also be used for incorporation into cosmetic products different hydroxyalkyk substituted ureas as well as mixtures with unsubstituted Urea used earth. It is also not absolutely necessary to use the pure Establish compounds, but the crude products of the reaction can also be used if you get them by treatment with an acidic cation exchanger on one sets a neutral pH value.

Als Hautpflege-, Hautschutz- und Hautreinirrngsmittel, denen durch den Zusatz der erfindungsgemäß zu verwendenden N-Hydroxyalkyl-alkansäureamide besondere hauptflegende Eigenschaften verliehen werden, sind Tagescremes, Babycremes, Nacht- und Nährcremes, Reinigungscremes, Hautschutzcremes, Giycerincrenes, Cremes mit speziollen Zusätzen tierischer und pflanzlicher Jlerkunft, Sonnenschutzcremes und Sonnenschutzemulsionen, Seifen, Bndeöle, Schaumbäder, Duschbcder Gesichtswasser, Rasierwasser zu nennen. Die Einarbeitung in die lIautpfloge-, Hautschutz- und Hautreinigungsmittel kann in bekannter Weise durch einfaches Einrühren bzw. Auflösen erfolgen. Neben den erfindungsgemäß einzusetzenden hydroxyalkylsubstituierten Harnstoffen können die kosmetischen Präparationen die in diesen iiblicherweise vorhandenen Bestandteile, wie z.B. Emulgatoren, Fettsubstanzen, Pflanzenauszüge, Konservierungsmittel, Duftstoffe, Lösungsmittel in den herkömmlichen Mengen enthalten, Der pH-Wert der Hautpflege- und Haut schutzmittel kann sich im Bereich von sauer bis neutral bewegen und wird zweckmäßigerweise auf schwach saure Werte um pH 6 eingestellt.As skin care, skin protection and skin cleansing agents, which by the addition of the N-hydroxyalkyl-alkanoic acid amides to be used according to the invention is particular the main skin care properties are day creams, baby creams, night creams and nourishing creams, cleansing creams, skin protection creams, Giycerin creams, creams with special Additives of animal and vegetable origin, sun protection creams and sun protection emulsions, Soaps, band oils, bubble baths, shower baths, face tonic, and aftershave. Familiarization with the care products, skin protection products and skin cleansing agents can be be carried out in a known manner by simply stirring in or dissolving. In addition to the invention The hydroxyalkyl-substituted ureas to be used can be the cosmetic preparations the constituents usually present in these, such as emulsifiers, fatty substances, Plant extracts, preservatives, fragrances, solvents in the conventional Contain quantities, The pH of the skin care and skin protection products can vary Move the range from acidic to neutral and is conveniently set to weakly acidic Values adjusted to pH 6.

Bei den Hautreinigungsmitteln auf Seifenbasis wird eine möglichst schwach alkalische Einstellung angestrebt, Die nachfolgenden Eeispiole sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu bes chräiilcen.When it comes to soap-based skin cleansers, one is possible The aim is to achieve a weakly alkaline setting Explain the subject matter of the invention in more detail without, however, referring to it.

B e i s p i e 1 c Von den erfindungsgemäß als Haut-Feuchthaltemittel einzusetzenden hydroxyalkylsubstituierten Harnstoffen wurden nachstehend aufgeführte Verbindungen entsprechenden Prüfungen unterworfen und in Rezepturen verwendet. Zunächst wird die Herstellung der Produkte beschrieben, A) N-(2-Hydroxyäthyl)-harnstoff Eine Mischung von 61 g (1 Mol) Äthanolamin und 60 g (1 Mol) harnstoff wurde 8 Stunden lang auf 1000C erwärmt. Nach dem Erkalten kristallisierte die Mischung, und es wurde in nahezu quantitativer Ausbeute N-(2-Hydroxyäthyl) harnstoff vom Schmelzpunkt 89-91 0C erhalten. Durch Umkristallisieren aus Äthanol/Äther ließ sich der Schmelzpunkt auf 90-92°C steigen. B e i s p i e 1 c Of the invention as skin moisturizers Hydroxyalkyl-substituted ureas to be used are listed below Compounds subjected to appropriate tests and used in formulations. First the preparation of the products is described, A) N- (2-hydroxyethyl) urea A Mixture of 61 g (1 mol) of ethanolamine and 60 g (1 mol) of urea was 8 hours heated to 1000C for a long time. After cooling, the mixture crystallized and it became in almost quantitative yield N- (2-hydroxyethyl) urea with a melting point of 89-91 0C received. The melting point could be determined by recrystallization from ethanol / ether rise to 90-92 ° C.

Für den Einsatz in kosmetischen Produkten ist aber eine Reinigung über Umkristallisieren nicht erforderlich. Zu diesem Zweck wird die wäßrige Lösung des Rohproduktes unter Rühren mit der H-Form eines Kationenaustauscher-Harzes, zum Beispiel Levatit S 100 (R), bis zur Einstellung eines pII-Wertes von 6 versetzt und anschließend wieder abfiltriert, Die so erhaltene wäßrige Lösung des N-(2-Hydroxyäthyl)-harnstoffs ist ohne weitere Behandlung für kosmetische Zwecke einsetzbar. However, cleaning is required for use in cosmetic products not necessary via recrystallization. For this purpose, the aqueous solution of the crude product while stirring with the H-form of a cation exchange resin, for Example Levatit S 100 (R), offset up to the setting of a pII value of 6 and then filtered off again, the resulting aqueous solution of N- (2-hydroxyethyl) urea can be used for cosmetic purposes without further treatment.

In entsprechender Weise wurden hergestellt: b) N-(2-Hydroxypropyl)-harnstoff Schmp. 1180C nach Umkristallisation aus Dioxan.The following were prepared in a corresponding manner: b) N- (2-hydroxypropyl) urea Mp 1180C after recrystallization from dioxane.

C) N,N-Bis-(2-hydroxyäthyl)-harnstoff Schmp, 75-760C nach Umkristallisation aus Chloroform/ Äthanol.C) N, N-bis (2-hydroxyethyl) urea mp, 75-760C after recrystallization from chloroform / ethanol.

D) N-(2-Hydroxy-2-methyl-2-propyl)-harnstoff Eine Lösung von 81 g (1 Mol) 2-Amino-2-methyl-propanol in 100 ml Wasser wurde mit 100 g 36 %iger Salzsäure (1 Mol) neutralisiert und anschließend bei Raumtemperatur unter Rillen mit einer Aufschlämmung von 65 g (1 Mol) Natriumcyaiiat in 300 ml Wasser portionsweise versetzt. Nach 16-stündigem Rühren bei Raumtemperatur wurde die Lösung unter vermindertem Druck eingedampft und der feste RUckstand mit siedendem Äthanol extrahiert. Nach Abdestillieren des Äthanols wurde der Rückstand aus Äthanol umkristallisiert.D) N- (2-Hydroxy-2-methyl-2-propyl) urea A solution of 81 g (1 mol) of 2-amino-2-methyl-propanol in 100 ml of water was mixed with 100 g of 36% hydrochloric acid (1 mol) and then neutralized at room temperature with a Slurry of 65 g (1 mol) of sodium cyanate in 300 ml of water were added in portions. After stirring for 16 hours at room temperature, the solution was reduced under reduced pressure Evaporated pressure and the solid residue extracted with boiling ethanol. To Distilling off the ethanol, the residue was recrystallized from ethanol.

Es wurden 36 g, das sind 27 % der Theorie, an reinem N-(2-Hydroxy-2-methyl-2-propyl)-harnstoff vom Schmp. 140°C isoliert. There were 36 g, that is 27% of theory, of pure N- (2-hydroxy-2-methyl-2-propyl) urea isolated from melting point 140.degree.

In entsprechender Weise wurden hergestellt: E) N-(1,3-Dihydroxy-2-methyl-2-propyl)-harnstoff Farbloses Harz mit einem Brechungsindex n20 : 1.5030.The following were prepared in a corresponding manner: E) N- (1,3-dihydroxy-2-methyl-2-propyl) urea Colorless resin with a refractive index n20: 1.5030.

F) N-(1,3-Dihydroxy-2-hydroxymethyl-2-propyl)-harnstoff Schuh. 1380C nach Umkristallisation aus Äthanol.F) N- (1,3-dihydroxy-2-hydroxymethyl-2-propyl) urea shoe. 1380C after recrystallization from ethanol.

G) N,N'-Bis-(2-hydroxyäthyl)-harnstoff Eine Mischung aus 43,5 g (0,5 Mol) 2-Oxazolidon und 30,6 g (O,5 Mol) Äthanolamin wurde 2 Stunden lang auf 14500 erwärmt. Nach dem Abkühlen mit Eis/Wasser erstarrte der rohe N,N'-Bis-(2-hydroxyäthyl)-harnstoff zu einer wachsartigen Masse. Nach dem Umkristallisieren aus Äthanol/ Chloroform besaß die reine Verbindung einen Schmelzpunkt von 54-550C.G) N, N'-bis (2-hydroxyethyl) urea A mixture of 43.5 g (0.5 Mol) 2-oxazolidone and 30.6 g (0.5 mol) ethanolamine were heated to 14500 for 2 hours warmed up. After cooling with ice / water, the crude N, N'-bis (2-hydroxyethyl) urea solidified to a waxy mass. After recrystallization from ethanol / chloroform the pure compound had a melting point of 54-550C.

Bei den Produkten C, D, 12, F handelt cs sich um neue, bisher noch nicht als solche beschriebene Verbindungen, Das günstige Verhalten der erfindungsgemäß einzugesetzten Verbindungen im Ilinblick auf Wasseraufnahmefähigkeit und Wasserrückhaltevermögen wurde mittels nachstehend näher beschriebener Prüfmethoden festgestellt. Es handelt sich dabei um ein Verfahren zur Ermittlung der Gleichgewichtsfeuchte, die ein Ttfnß für das Wasserretentionsvermögen darstellt und um die Bestimmung der Wasserretention, Rehydratation und Elastizität imprägnierter Schweineepidermis.The products C, D, 12, F are new, so far compounds not described as such, the favorable behavior of the invention The compounds used in the Ilin view of water absorption capacity and water retention capacity was determined by means of the test methods described in more detail below. It deals is a process for determining the equilibrium moisture content, which is a Ttfnß for the water retention capacity and the determination of the water retention, Rehydration and elasticity of impregnated pig epidermis.

1. Ermittlung der Gleichsgewichtsfeuchts Die zu untersuchenden Substanzen (ca, 300 - 500 mg) wurden mit einer definierten Menge Wasser angefeuchtet und bei 230C 24 Stunden verschiedenen relativen Luftfeuchtigkeiten (1 %, 30 %, 47 %, 65 %, 89 % und 100 % relativer Feuchtigkeit) ausgesetzt. Die aufgenommene bzw. abgegebene Wassermenge wurde gravimetrisch bestimmt und graphisch aufgetragen. Aus den hieraus resultierenden Kurven kann auf diejenige relative Feuchtigkeit geschlossen werden, bei der weder Wasserabgabe noch Wasseraufnahme erfolgt. Dieser Wert, der als Gleichgewichtsfeuchte bezeichnet wird, ist ein Maß für das Wasserretentionsvermögen einer Substanz, Je niedriger der Wert liegt, umso positiver ist das Produkt zu beurteilen, Aus der Steilheit der Kurve läßt sich weiterhin das Wasseraufnahmevermögen (Hygroskopizität) der Substanz ablesen.1. Determination of equilibrium moisture The substances to be examined (approx. 300 - 500 mg) were moistened with a defined amount of water and at 230C 24 hours different relative humidity (1%, 30%, 47%, 65 %, 89% and 100% relative humidity). The accepted or submitted The amount of water was determined gravimetrically and plotted graphically. From here The resulting curves can be deduced from the relative humidity in which neither water release nor water absorption takes place. This value, called equilibrium moisture is a measure of the water retention capacity of a substance, Je The lower the value, the more positive the product is to be assessed Steepness of the curve, the water absorption capacity (hygroscopicity) read the substance.

2. Messungen an der Schweineepidermis a) Gewinnung der Schweineepidermis Unmittelbar nach dem Töten der Schweino werden die Borsten der Haut mittels einer Haarschermaschine (Scherkopf 0,1 mm) abgeschnitten. Die Schweine werden in 60°C warmem Wasser ca. 3 - 5 Minuten gebrüht, die Epidermis anschließend abgeschält und bei -20°C bis zum Gebrauch gelagert.2. Measurements on the pig epidermis a) Obtaining the pig epidermis Direct After killing the Schweino, the bristles of the skin are removed using a hair clipper (Shaving head 0.1 mm) cut off. The pigs are heated in water at 60 ° C for approx. Brewed for 3 - 5 minutes, then peeled off the epidermis and store at -20 ° C until Use stored.

b) Bestimmung der Wasserretention sowie der Rehydratation imprägnierter Schweineepidermis, Ausgestanzte Epidermisstückchen (1 x 2 cm) wurden zwei Stunden in 10 %iger Lösung der Prüfsubstanz gebadet, unter standardisierten Bedingungen mittels einer kleinen Presse abgetupft und 24 Stunden zwischen zwei Klammern frci hängend in einem 100 ml Erlenmeierkolben bei 230C und 30 % relativer Feuchtigkeit sowie 50 % relativer Feuchtigkeit (eingestellt durch Schwefelsäure-Wasser-Mischungen) getrocknet. Die Austrocknung der imprägnierten Probe auf X-% des Anfangsgewichtos wurde mit dem entsprechenden Wert der nur in Wasser gebadeten Epidermis (Blindwert) verglichen. In der Tabelle ist die Verbesserung der Wasserretention sowie der Rehydratation gegenüber dem Blindwert in as H20 angegeben, Die Abweichungen betrugen bei den jeweiligen Doppelversuchen maximal i 2 absolute Einheiten. Bei größeren Abweichungen wurde der Versuch wiederholt. Die Rehydratation wurde durch 24-stündige Trocknung der imprägnierten und abgetupften Schweineepidermis bei 30 % relativer Feuchtigkeit und anschließende 24-stündige Inkubation bei 90 % relativer Feuchtigkeit analog bestimmt, c) Elastizitätsmessungen an imprägnierter Schweineepidermis.b) Determination of water retention and rehydration of the impregnated Pig epidermis, punched pieces of epidermis (1 x 2 cm) were two hours bathed in 10% solution of the test substance under standardized conditions dabbed off using a small press and frci between two clamps for 24 hours hanging in a 100 ml conical flask at 230C and 30% relative humidity as well as 50% relative humidity (adjusted by sulfuric acid-water mixtures) dried. The drying of the impregnated sample to X% of the initial weight was compared with the corresponding value of the epidermis bathed only in water (blank value) compared. The table shows the improvement in water retention and rehydration compared to the blank value given in as H20, the deviations were for the respective Double attempts a maximum of i 2 absolute units. In the case of larger deviations, the attempt is repeated. The rehydration was achieved by drying the impregnated and dabbed pig epidermis at 30% relative humidity and subsequent incubation for 24 hours at 90% relative humidity analogously certainly, c) Elasticity measurements on impregnated pig epidermis.

Ausgestanzte Epidermisstückchen (1 x 6 cm) wurden zwei Stunden in 10 %iger wäßriger Lösung der zu prüfenden Substanz gebadet und unter standardisierten Bedingungen abgetupft. Die Proben wurden zwischen zwei Klammern frei hängend bei 70 Co' relativer Feuchtigkeit sowie 90 0 relativer Feuchtigkeit 24 Stunden inkubiert und in einer Zwick-ZUgprüfmaschine (Typ: 1402) bei 0 - 50 p Belastung gedehnt. Als Maß für die Elastizität wurde die Dehnung in mm angegeben, die im Hooke'schen Bereich bei einer Belastung zwischen 5 - 30 p gemessen wurde. Punched pieces of epidermis (1 x 6 cm) were in 10% aqueous solution of the substance to be tested bathed and standardized Conditions dabbed. The samples were hanging freely between two brackets 70 Co 'relative humidity and 90 0 relative humidity incubated for 24 hours and stretched in a Zwick-ZUgprüfmaschine (type: 1402) at 0 - 50 p load. as The measure of elasticity was the elongation in mm, which was in the Hooke's range was measured at a load between 5 - 30 p.

Die bei den vorstehend beschriebenen Prüfungen erhaltenen Meßwerte sind nachstehender Tabelle 1 zu entnehmen.The measured values obtained in the tests described above can be found in Table 1 below.

T a b e l l e 1 Messungen an der Schweineepidermis Produkt Gleichge- Wasserretention Rehydratation mm-Dehnung nach Belastung wichts- % H2O nach Aus- % Wasserauf- zwischen 5 - 30 g feuchts trocknung bei nahme bei (% r.F) 30 % r.F. 50 % r.F. 90 % r.F. 90 % r.F. 75 % r.F. Blind- wert - 0 0 0 0,3-0,5 0 A 70 13 18 21 6,2 0,8 C 62 10 10 11 5,1 1,5 G 58 11 11 13 4,7 0,8 Der vorstehenden Tabelle ist neben der starken Wasseraufnahmefähigkeit auch das beschtliche Wasserretentionsvermögen der erfindungsgemäß einzusetzenden Verbindungen und damit ihre gute Eignung als Haut-Feuchthaltemittel in Hautpflege-, Hautschutz-und Hautreinigungsmitteln zu entnehmen Nachstehend werden noch einige Beispiele für kosmetische Zubereitungen aufgeführt, die die erfindungsgemäß einzusetzenden Substanzen als Haut-Feuchthaltemittel enthalten.Table 1 Measurements on the pig epidermis Product equal to water retention rehydration mm-elongation after exercise % by weight H2O after% water absorption between 5 - 30 g wet drying when taking at (% RH) 30% RH 50% RH 90% RH 90% RH 75% RH Blind- value - 0 0 0 0.3-0.5 0 A 70 13 18 21 6.2 0.8 C 62 10 10 11 5.1 1.5 G 58 11 11 13 4.7 0.8 In addition to the strong water absorption capacity, the table above also shows the actual water retention capacity of the compounds to be used according to the invention and thus their good suitability as skin moisturizers in skin care, skin protection and skin cleansing agents Contained as a skin moisturizer.

Tagecreme schwach fettend Fettsäurepartialglycerid Cutina MD(R) Dehydag 6,0 Gew.Teile Stearinsäure 8,0 " " Gemisch nichtionogener Emulgatoren Eumulgin c 700(R) Dehydag 3, O " 2-Octyldodecanol 4,0 " " Pflanzenöl 3,0 " " Paraffinöl 5,0 " " Triäthanolamin 0,4 " " 1,2-Propylenglykol 3,0 " " Produkt A 6,0 " " Nipagin M 0,2 " " Parfümöl 1,0 " " Wasser 6o, 4 1 II Baby-Creme Gemisch höhermolekularer Ester, vorwiegend Mischester aus Pentacrythrit-Fettsäureester und Zitronensäurefettalkoholester Dehymuls E(R) Dehydag 7,0 Gew.Teile Olsäuredecylester 10,0 " " Vaseline 10,0 " " Wollfett 5,0 " " Borsäure 0,2 " " Talkum 12,0 " " Zinkoxid 8,0 " " Nipagin M 0,2 " " Produkt G 8,0 " " Wasser 39,6 " " Nachtcreme Kolloiddisperses Gemisch aus 90 Teilen Cetylstearylalkohol und 10 Teilen Natriumlaurylsulfat 10,0 Gew. Teile 2-Octyldodecanol 10,0 " " Pflanzenöl 7,0 " " Wollfett 2,0 " " Glycerin 1,0 " " Produkt C 10,0 " " Nipagin M 0,2 " " Parfümöl 1,0 " " Wasser 56,8 " " Bor-Glycerin-Creme Kolloiddisperses Gemisch aus 90 Teilen Cetylstearylalkohol und 10 Teilen Natriumlaurylsulfat 12,0 Gew. Teile 2-Octyldodecanol 8,0 " " Pflanzenöl 5,0 " " Borsäure 2,0 " " Glycerin 28,0 " " Nipagin M 0,2 " " Produkt N 6,0 " " Wasser 38,8 " " Feuchtigkeitscreme Gemisch von Mono- und Diglyceriden der Palmitin- und Stearinsäure, Eumulsen MD(R) Dehydag 16,0 Gew.-Teile Fettalkoholpolyglykoläther, Eumulgin B3(R) Dehydag 4,0 " " Ölsäuredecylester 5,0 " " Pflanzenöl 5,0 " " Paraffinöl 2,0 " " Produkt A 5,0 " " 1,2-Propylenglykol 5,0 " " p-Hydroxybenzoesäuremethylester 0,2 " " Wasser 57,8 " " Feuchtigkei tscrene Selbstemulgiercndes Gemisch aus Mono-und Diglyceriden höherer gesättigter Fettsäuren Eumulsan KD(R) Dehydag 16,0 Gew.-Teile fettalkoholpolyglykoläther Eumulgin B 3 (R) Dehydag 1,0 " 2-Octyldodecanol 12,0 " Isopropylmyristat 8,0 Paraffinöl 4,0 Produkt G 5,0 Sorbitlösung Karion (R) flüssig 8,0 p-Hydroxybenzoesäuremethylester 0,2 Wasser 55,8 Feuchtigkeitsemulsion Gemisch von Mono- und Diglyceriden der Palmitin- und Stearinsäure, Eumulsan Dehydag 6,0 Gew.-Teile Fettalkoholpolyglykoläther, Eumulgin B3 (R) Dehydag 4,0 2-Octyldodecanol 10,0 Pflanzenöl 4,0 Paraffinöl 4,0 Produkt B 5,0 1,2-Propylenglykol 7,0 p-Hydroxybenzoesäuremethylester 0,2 Wasser 59,8 Sonnenschutzcreme Gemisch höhermolokularer Ester mit Fettstoffen Dehymuls K (n) Dehydag 30,0 Gew.Teile Ölsäuredecylester 15,0 " Lichtschutzmittel 5,0 t' tI Nipagin M 0,2 " " Produkt D 8,0 " " Wasser 41,8 t Gesichtsmaske Gemisch von Fettsäurepartialglycerid mit Emulgatoren Cutina LE(R) Dehydag 12,0 Gew.Teile Ölsäuredecylester 4,0 " " Vitaminöl 5,0 " " Kaolin 2,0 " " Reisstärke 3,0 " " Nipagin M 0,2 " " Produkt F 10,0 " " Wasser 63,8 " " Rasierwasser Oleyl-Cetylalkohol 1,0 Gew.Teile Äthanol 96 % 67,5 II Methanol 0,2 " " Kampfer 0,2 " " Perubalsam 0,1 " " Parfüm 0,5 " " Hammamelisextrakt 10,0 " " Borsäure 0,5 " lt Produkt A 5,0 " " Produkt E 5,0 " " Wasser 10,0 " " Gesichtswasser Gurkensaft 15,0 Gew.Teile Citronensäure 0,2 " " Äthanol 96 %ig 15,0 " " Produkt C 5,0 " " Produkt B 5,0 " " Duftstoff 1,0 " " Wasser 58,8 " " Schaumbad Monoäthanolaminlaurylsulfat ca, 33% Waschaktivsubstanz 66,0 Gew.Teile Kokosfettsurediätbanolamid 3,0 " Produkt G 10,0 " " Parfümöl 3,0 " " Wasser 18,0 " " Creme-Schaumbad Natriumlauryläthersulfat ca. 30 % WAS 78,0 Gew.Teile Ölsäurediäthanolamid 4,0 " " Laurinsäurehexylester 8,0 " lt Produkt A 5, " " 1,2-Propylenglykol 2,0 " " Parfümöl 3,0 o Seife mit einem Gehalt an Haut-Feuchthaltemitteln Es wurde ein zu 80 % aus Natriumalgseife und zu 20 p aus Natrium-Cocosseife besteheIldes Gemisch verwendet. Die in Form von Flocken vorliegende Seife mit einem Wassergehalt von 20 96 wurde mit 0,2 Gewichtsteilen 1-Hydroxyäthan-1,1-diphosphonsäure, 10,0 " " Produkt A, 3,0 " " Parfümöl, bezogen auf 100 Gewichtsteile Seife, vermischt, in einer Strangpresse verformt und zu Stücken gepreßt.Day cream, low-fat fatty acid partial glyceride Cutina MD (R) Dehydag 6.0 parts by weight of stearic acid 8.0 "" mixture of nonionic emulsifiers eumulgin c 700 (R) Dehydag 3, O "2-Octyldodecanol 4.0" "Vegetable Oil 3.0" "Paraffin Oil 5.0 "" Triethanolamine 0.4 "" 1,2-Propylene Glycol 3.0 "" Product A 6.0 "" Nipagin M 0.2 "" Perfume oil 1.0 "" Water 6o, 4 1 II Baby cream mixture of higher molecular weight Esters, predominantly mixed esters of pentacrythritol fatty acid esters and citric acid fatty alcohol esters Dehymuls E (R) Dehydag 7.0 parts by weight oleic acid decyl ester 10.0 "" Vaseline 10.0 "" Wool fat 5.0 "" Boric acid 0.2 "" Talc 12.0 "" Zinc oxide 8.0 "" Nipagin M 0.2 "" Product G 8.0 "" Water 39.6 "" Night cream colloidal disperses Mixture of 90 parts of cetostearyl alcohol and 10 parts of sodium lauryl sulfate 10.0 Parts by weight of 2-octyldodecanol 10.0 "" vegetable oil 7.0 "" wool fat 2.0 "" glycerine 1.0 "" Product C 10.0 "" Nipagin M 0.2 "" Perfume Oil 1.0 "" Water 56.8 "" Boron-Glycerin Cream Colloidal mixture of 90 parts of cetostearyl alcohol and 10 parts of sodium lauryl sulfate 12.0 parts by weight of 2-octyldodecanol 8.0 "" vegetable oil 5.0 "" boric acid 2.0 "" glycerin 28.0 "" Nipagin M 0.2 "" Product N 6.0 "" Water 38.8 "" Moisturizer Mixture of mono- and diglycerides of palmitic and stearic acid, Eumulsen MD (R) Dehydag 16.0 parts by weight fatty alcohol polyglycol ether, Eumulgin B3 (R) Dehydag 4.0 " "Decyl oleic ester 5.0" "Vegetable oil 5.0" "Paraffin oil 2.0" "Product A 5.0 "" 1,2-propylene glycol 5.0 "" methyl p-hydroxybenzoate 0.2 "" water 57.8 "" Moisture-free self-emulsifying mixture of mono- and Diglycerides of higher saturated fatty acids Eumulsan KD (R) Dehydag 16.0 parts by weight fatty alcohol polyglycol ether Eumulgin B 3 (R) Dehydag 1.0 "2-Octyldodecanol 12.0 "Isopropyl myristate 8.0 Paraffin oil 4.0 Product G 5.0 Sorbitol solution Karion (R) liquid 8.0 methyl p-hydroxybenzoate 0.2 water 55.8 moisture emulsion mixture of mono- and diglycerides of palmitic and stearic acid, Eumulsan Dehydag 6.0 Parts by weight of fatty alcohol polyglycol ether, Eumulgin B3 (R) Dehydag 4.0 2-octyldodecanol 10.0 Vegetable oil 4.0 Paraffin oil 4.0 Product B 5.0 1,2-propylene glycol 7.0 methyl p-hydroxybenzoate 0.2 Water 59.8 Sun protection cream Mixture of higher molecular weight esters with fatty substances Dehymuls K (n) Dehydag 30.0 parts by weight of oleic acid decyl ester 15.0 "light stabilizer 5.0 t 'tI Nipagin M 0.2 "" Product D 8.0 "" Water 41.8 t Face mask Mixture of fatty acid partial glyceride with emulsifiers Cutina LE (R) Dehydag 12.0 parts by weight Decyl oleic ester 4.0 "" Vitamin oil 5.0 "" Kaolin 2.0 "" Rice starch 3.0 "" Nipagin M 0.2 "" product F 10.0 "" water 63.8 "" aftershave oleyl cetyl alcohol 1.0 Parts by weight ethanol 96% 67.5 II methanol 0.2 "" camphor 0.2 "" Peru balsam 0.1 " "Perfume 0.5" "Hammamelis extract 10.0" "Boric acid 0.5" lt product A 5.0 "" Product E 5.0 "" Water 10.0 "" Toner cucumber juice 15.0 parts by weight citric acid 0.2 "" Ethanol 96% 15.0 "" Product C 5.0 "" Product B 5.0 "" Perfume 1.0 "" Water 58.8 "" Bubble bath monoethanolamine lauryl sulfate approx. 33% Washing active substance 66.0 parts by weight coconut fatty acid dietbanolamide 3.0 "product G 10.0 "" Perfume oil 3.0 "" Water 18.0 "" Cream foam bath Sodium lauryl ether sulfate approx. 30% WHAT 78.0 parts by weight oleic acid diethanolamide 4.0 "" lauric acid hexyl ester 8.0 " According to product A 5, "" 1,2-propylene glycol 2.0 "" perfume oil 3.0 o soap with a content of skin moisturizers. A 80% sodium algae soap and 20% p The mixture consists of sodium coconut soap. The one present in the form of flakes Soap with a water content of 20 96 was with 0.2 parts by weight of 1-hydroxyethane-1,1-diphosphonic acid, 10.0 "" product A, 3.0 "" perfume oil, based on 100 parts by weight of soap, mixed, deformed in an extruder and pressed into pieces.

Syndet-Seifenstück mit einem Gehalt an Haut-Feuchthaltemittel Dem Beispiel wurde ein Syndetstück auf Basis eines Gemisches von Olefinsulfonat und Sulfobernsteinestersalz zugrunde gelegt.Syndet bar containing skin moisturizer Dem An example was a syndet piece based on a mixture of olefin sulfonate and Sulphobernsteinesteralz used as a basis.

Zur Herstellung des Gemisches diente das Dinatriumsalz eines Sulfobernsteinsäure-monofettalkoholesters, der aus der C12-C18-Fraktion eines Kokosfettalkohols herge-.The disodium salt of a sulfosuccinic acid monofatty alcohol ester was used to prepare the mixture, from the C12-C18 fraction of a coconut fatty alcohol.

stellt worden war. Das Olefinsulfonat stammte von einem Gemisch geradkettiger d,-Olefine mit 15 - 18 Kohlenstoffatomen ab. Dieses Olefingemisch war durch Sulfonieren von 1 Mol Olefin mit ca. 1,2 Mol gasförmigem, inertgas-verdünntem Schwefeltrioxid, Hydrolysieren des rohen Sulfonierungsproduktes mit der berechneten Menge Natronlauge bei Temperaturen von etwa 1000C und Bleichen des Sulfonates mit Hilfe von Hypochlorit hergestellt worden. Das Gemisch der beiden Sulfonate enthielt etwa 5 Gewichtsprozent Neutralsalze (Natriumsulfat und Natriumchlorid), bezogen auf wasserfreies Sulfonat. Die Syndetmasse hatte folgende Zusammensetzung: 70 Gewichtsteile Tensidgemisch, bestehend aus 60 Gew.- Olefinsulfonat 40 Gew.-% Dinatriumsalz des Sulfobernsteinsäureesters 15 Gewichtsteile Talgfettsäure (JZ 2) 2 Gewichtsteile Lanolin 5 Gewichtsteile Wasser 8 Gewichtsteile Produkt G 2 Gewichtsteile Parfümöl.had been put. The olefin sulfonate was derived from a mixture of straight chain d, olefins with 15-18 carbon atoms. This mixture of olefins was by sulfonation of 1 mole of olefin with approx. 1.2 moles of gaseous, inert gas-diluted sulfur trioxide, Hydrolyze the crude sulfonation product with the calculated amount of sodium hydroxide solution at temperatures of about 1000C and bleaching of the sulfonate with the help of hypochlorite has been manufactured. The mixture of the two sulfonates contained about 5 percent by weight Neutral salts (sodium sulfate and sodium chloride) based on anhydrous sulfonate. The syndet mass had the following composition: 70 parts by weight of surfactant mixture, consisting of 60% by weight of olefin sulfonate and 40% by weight of the disodium salt of the sulfosuccinic acid ester 15 parts by weight of tallow fatty acid (JZ 2) 2 parts by weight of lanolin 5 parts by weight of water 8 parts by weight of product G 2 parts by weight of perfume oil.

Die Masse wurde in einer Strangpresse verformt und zu Stücken gepreßt.The mass was shaped in an extruder and pressed into pieces.

An die Stelle der in den vorstehenden Rezepturen genannten erfindungsgemäß zu verwendenden Verbindungen können mit gleich gutem Erfolg auch andere der aufgeführten erfindungsgemäß einzusetzenden Produkte treten.Instead of those mentioned in the above formulations according to the invention The compounds to be used can also be other of those listed with equal success products to be used according to the invention occur.

Claims (1)

P a t c n i: a n s p r ü c h e 1. Kosmetische Mittel, insbesondere Hautpflege-, Hautschutz-und Hautreinigungsmittel auf Basis üblicher Bestandteile wie Emulgatoren, Fettsubstanzen, Pflanzenauszüge, Lösungsmittel, Duftstoffe, Verdickungs-, Konservierungsmittel, Tenside, gekennzeichnet durch einem Gehalt an hydroxyalkylsubstituierten Harnstoffen der allgemeinen Formel in der R1, R2, R3 und R4 unabhängig voneinander für ein Wasserstoffatom, eine niedere (C1-C4)-Alkyl- oder eine niedere (C2-C6)-Hydroxyalkylgruppe, die 1 - 5 Hydroxyl-bzw. Hydroxyalkylgruppen enthalten kann, stehen, mit der Maßgabe, daß wenigstens einer der Reste R1 - R4 eine Hydroxyalkyl- oder Oligohydroxyalkylgruppe darstellt, in einer Menge von 1 bis 20 Gewichtsprozent, vorzugsweise 3 bis 10 Gewichstprozent, bezogen auf das gesamte lfittel, 2, Kosmetische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß man die hydroxyalkylsubstituierten Harnstoffe in Form der Rohprodukte der Herstellungsreaktion nach Behandlung mit einem sauren Kationenaustauscher zur Einstellung auf einen neutralen pH-Wert einsetzt.P atcni: claims 1. Cosmetic agents, in particular skin care, skin protection and skin cleaning agents based on common ingredients such as emulsifiers, fatty substances, plant extracts, solvents, fragrances, thickeners, preservatives, surfactants, characterized by a content of hydroxyalkyl-substituted ureas in general formula in which R1, R2, R3 and R4 independently represent a hydrogen atom, a lower (C1-C4) -alkyl or a lower (C2-C6) -hydroxyalkyl group, the 1-5 hydroxyl or. May contain hydroxyalkyl groups, with the proviso that at least one of the radicals R1 - R4 represents a hydroxyalkyl or oligohydroxyalkyl group, in an amount of 1 to 20 percent by weight, preferably 3 to 10 percent by weight, based on the total solvent, 2, cosmetic agents according to claim 1, characterized in that the hydroxyalkyl-substituted ureas are used in the form of the crude products of the production reaction after treatment with an acidic cation exchanger to adjust the pH to a neutral value. 3. Kosmetische Mittcl nach Anspruch 1 und 2, dadurch gekennzeichnet, daß sie neben den als llaut-Feuchthaltemittel wirkend en hydroxyalkylsubstituierten Ilarnst offen die üblichen Bestandteile wie Emulgatoren, Fettsubstanzen, Pflanzenauszüge, Konservierungsmittel, Duftstoffe, Verdickungs-, Lösungsmittel, Tenside in den herkömmlichen Mengen enthalten.3. Cosmetic Mittcl according to claim 1 and 2, characterized in that that they are hydroxyalkyl-substituted in addition to acting as llaut humectants Ilarnst openly the usual ingredients such as emulsifiers, fatty substances, Plant extracts, Preservatives, fragrances, thickeners, solvents, surfactants in the conventional Quantities included. 4. N,N-Bis-(2-hydroxyäthyl)-harnstoff.4. N, N-bis (2-hydroxyethyl) urea. 5. N-(2-Hydroxy-2-methyl-2-propyl)-harnstoff.5. N- (2-Hydroxy-2-methyl-2-propyl) urea. 6. N-(1,3-Dihydroxy-2-methyl-2-propyl)-harnstoff.6. N- (1,3-dihydroxy-2-methyl-2-propyl) urea. 7. N-(1,3-Dihydroxy-2-hydroxymethyl-2-propyl)-harnstoff.7. N- (1,3-dihydroxy-2-hydroxymethyl-2-propyl) urea. 8. Verfahren zur Herstellung von D-(2-Hydroxyalykl)-harnstoffen durch Umsetzung von gegebenenfalls substituierten 2-Oxazolidinen bei erhöhter Temperatur zwischen vorzugsweise 100 bis 200°C mit primären oder sekundären, insbesondere primären Aminen.8. Process for the preparation of D- (2-Hydroxyalykl) -ureas by Implementation of substituted or unsubstituted 2-oxazolidines at elevated temperature between preferably 100 to 200 ° C with primary or secondary, especially primary Amines.
DE19772703185 1977-01-27 1977-01-27 Cosmetics contg. hydroxyalkyl-urea derivs. - useful as skin moisture regulators Withdrawn DE2703185A1 (en)

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Cited By (49)

* Cited by examiner, † Cited by third party
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EP0135832A2 (en) * 1983-09-10 1985-04-03 Bayer Ag Use of polyhydroxyalkyl mono-urea for polyurethane foams, dispersions of the polyhydroxyalkyl mono-urea in polyols and tris-hydroxyalkyl mono-urea
WO1986000014A1 (en) * 1984-06-11 1986-01-03 Murray Weiner Topical compositions
FR2750334A1 (en) * 1996-07-01 1998-01-02 Oreal USE OF AMINO-ALCOHOL DERIVATIVES WITH A UREA FUNCTION IN AND FOR THE PREPARATION OF COSMETIC OR DERMATOLOGICAL COMPOSITIONS
EP0876812A2 (en) * 1997-05-06 1998-11-11 Basf Aktiengesellschaft Cosmetic compositions comprising saccharic acid ureides
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EP1774957A3 (en) * 2005-10-17 2012-01-25 Henkel AG & Co. KGaA Cleaning composition for oral and dental hygiene comprising hydroxyalkyl substituted urea
US8173144B2 (en) 2004-11-04 2012-05-08 L'oreal Administration of urea compounds for combating signs of cutaneous aging
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CN109640932A (en) * 2016-09-02 2019-04-16 莱雅公司 Composition comprising aqueous bead
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Cited By (85)

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EP0135832A3 (en) * 1983-09-10 1985-10-02 Bayer Ag Use of polyhydroxyalkyl mono-urea for polyurethane foams, dispersions of the polyhydroxyalkyl mono-urea in polyols and tris-hydroxyalkyl mono-urea
EP0135832A2 (en) * 1983-09-10 1985-04-03 Bayer Ag Use of polyhydroxyalkyl mono-urea for polyurethane foams, dispersions of the polyhydroxyalkyl mono-urea in polyols and tris-hydroxyalkyl mono-urea
WO1986000014A1 (en) * 1984-06-11 1986-01-03 Murray Weiner Topical compositions
EP1222916A3 (en) * 1996-07-01 2007-04-18 L'oreal Use of amino-alcohol derivatives containing a urea function as moisturiser in cosmetic or dermatological compositions
FR2750334A1 (en) * 1996-07-01 1998-01-02 Oreal USE OF AMINO-ALCOHOL DERIVATIVES WITH A UREA FUNCTION IN AND FOR THE PREPARATION OF COSMETIC OR DERMATOLOGICAL COMPOSITIONS
EP0815829A1 (en) * 1996-07-01 1998-01-07 L'oreal Use of amino-alcohol derivatives containing an urea function in cosmetic and dermatologic compositions
EP1222916A2 (en) * 1996-07-01 2002-07-17 L'oreal Use of amino-alcohol derivatives containing a urea function as moisturiser in cosmetic or dermatological compositions
US6335024B2 (en) 1996-07-01 2002-01-01 L'oreal Cosmetic and dermatological compositions containing aminoalcohol derivatives containing a urea functional group and uses thereof
EP0876812A3 (en) * 1997-05-06 2000-07-26 Basf Aktiengesellschaft Cosmetic compositions comprising saccharic acid ureides
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FR2770523A1 (en) * 1997-11-04 1999-05-07 Oreal CERAMID TYPE COMPOUND, PROCESS FOR PREPARATION AND USE
EP1060737A1 (en) * 1999-06-15 2000-12-20 Cognis Deutschland GmbH Acid acide amide catbonic carbonique Aqueous pearlescent concentrate
WO2005002517A2 (en) * 2003-06-26 2005-01-13 National Starch And Chemical Investment Holding Corporation Use of (hydroxyalkyl)urea and/or (hydroxyalkyl)amide for maintaining hydration of aqueous polymer compositions
WO2005002517A3 (en) * 2003-06-26 2005-02-10 Nat Starch Chem Invest Use of (hydroxyalkyl)urea and/or (hydroxyalkyl)amide for maintaining hydration of aqueous polymer compositions
AU2004231260B2 (en) * 2003-11-26 2009-08-27 Akzo Nobel Chemicals International B.V. Increased moisturization efficacy using hydroxyalkylurea
JP4695383B2 (en) * 2003-11-26 2011-06-08 アクゾ ノーベル ナムローゼ フェンノートシャップ Increased wetting efficacy using hydroxyalkylureas
US7816310B2 (en) 2003-11-26 2010-10-19 Akzo Nobel N.V. Increased moisturization efficacy using hydroxyalkylurea and ammonium lactate
EP1535607A1 (en) * 2003-11-26 2005-06-01 National Starch and Chemical Investment Holding Corporation Increased moisturization efficacy using hydroxyalkylurea
EP1935878A1 (en) 2003-11-26 2008-06-25 National Starch and Chemical Investment Holding Corporation Increased moisturization efficacy using hydroxyalkylurea
JP2005170941A (en) * 2003-11-26 2005-06-30 Natl Starch & Chem Investment Holding Corp Method for increasing moisturization efficacy using hydroxyalkylurea
WO2005079740A1 (en) * 2004-02-19 2005-09-01 Unilever Plc Stabilization with substituted ureas against color degradation of personal care products
AU2004316069B2 (en) * 2004-02-19 2007-10-11 Unilever Plc Stabilization with substituted ureas against color degradation of personal care products
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EP1674072A1 (en) 2004-11-04 2006-06-28 L'oreal Use of urea compounds to combat indications of skin ageing
US8173144B2 (en) 2004-11-04 2012-05-08 L'oreal Administration of urea compounds for combating signs of cutaneous aging
FR2877222A1 (en) * 2004-11-04 2006-05-05 Oreal Cosmetic composition, useful to treat dry skin, comprises hydroxy alkyl urea compounds and a hydrating agent (e.g. amino acids or their N-acyl derivatives, urea and cholesterol)
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US7615586B2 (en) 2004-11-09 2009-11-10 L'oreal Composition comprising a urea compound
EP1661550A1 (en) 2004-11-09 2006-05-31 L'oreal, S.A. Cosmetic and/or dermatological composition comprising urea compound
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JP2006137753A (en) * 2004-11-09 2006-06-01 L'oreal Sa Cosmetic and/or dermatological composition containing urea compound
JP2008521769A (en) * 2004-11-26 2008-06-26 ロレアル Cosmetic composition comprising an astringent and a hydroxyalkylurea
WO2006056491A1 (en) * 2004-11-26 2006-06-01 L'oréal Cosmetic composition comprising a tensioning agent and a hydroxyalkyl urea
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US7402301B2 (en) 2004-12-20 2008-07-22 L'oreal Sunscreen compositions comprising metal oxide mineral pigments and hydroxyalkylurea compounds
EP1671675A1 (en) 2004-12-20 2006-06-21 L'oreal Sun protection composition comprising at least a lipophilic uv filter and a hydroxyalkyl urea derivative
EP1671676A1 (en) * 2004-12-20 2006-06-21 L'oreal Sun protection composition comprising at least one hydrophilic uv filter and a hydroxyalkyl urea derivative
EP1671678A1 (en) * 2004-12-20 2006-06-21 L'oreal, S.A. Sun protection composition comprising at least an insoluble uv filter and a hydroxyalkyl urea derivative
EP1671680A1 (en) 2004-12-20 2006-06-21 L'oreal Self-tanning composition having two components, multicompartment device and process for colouring the skin
FR2879449A1 (en) * 2004-12-20 2006-06-23 Oreal Process of photostabilization of a dibenzoylmethane derivative with respect to UV radiation, comprises associating the dibenzoylmethane derivative with hydroxy alkyl urea compounds
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FR2884515A1 (en) * 2005-04-15 2006-10-20 Oreal Cosmetic use of a urea compound for nontherapeutic skin care, particularly for the moisturization of the skin
EP1743619A3 (en) * 2005-07-12 2010-06-30 L'oreal Cosmetic composition comprising an amphiphilic lipid phase
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JP2007023038A (en) * 2005-07-13 2007-02-01 L'oreal Sa Use of urea compound for promoting desquamation
EP1774957A3 (en) * 2005-10-17 2012-01-25 Henkel AG & Co. KGaA Cleaning composition for oral and dental hygiene comprising hydroxyalkyl substituted urea
WO2007057073A3 (en) * 2005-11-16 2007-07-05 Henkel Kgaa Volumising hair care agents
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DE102006034532A1 (en) * 2006-07-24 2008-01-31 Beiersdorf Ag Cosmetic preparation comprises (2-hydroxyethyl)urea, 1,3-dihydroxyacetone and tocopherylacetate, phenoxyethanol, ethylhexylglycerin, 2-methylpropane-1,3-diol, butylene glycol, 1,2-hexanediol, 1,2-octanediol and/or 1,2-decanediol
DE102006034531A1 (en) * 2006-07-24 2008-01-31 Beiersdorf Ag Cosmetic preparation, useful e.g. as repellents to protect against mosquitoes, as protective skin cream and to protect against UV-induced skin aging, comprises (2-hydroxyethyl)urea and myristylmyristate
DE102006034530A1 (en) * 2006-07-24 2008-01-31 Beiersdorf Ag Cosmetic preparation, useful e.g. as day or night cream to protect the skin against lesions, aging, dryness, roughness, itching and age spots, comprises (2-hydroxyethyl) urea and glucosyl glyceride
WO2011030308A1 (en) 2009-09-11 2011-03-17 L'oreal Make-up and/or care method for keratinous material
WO2013127552A3 (en) * 2012-02-29 2014-12-31 Henkel Ag & Co. Kgaa Emulsion having urea derivatives
CN104486947A (en) * 2012-07-13 2015-04-01 奥克西特诺工业与贸易公司 Adjuvant composition for use in herbicidal formulations containing glyphosate, use of the adjuvant composition, herbicidal formulations containing glyphosate and use of the herbicidal formulations
CN109640932A (en) * 2016-09-02 2019-04-16 莱雅公司 Composition comprising aqueous bead
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FR3117363A1 (en) 2020-12-10 2022-06-17 L'oreal Cosmetic substrate of natural origin

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