FR2699189A1 - Detergent composition intended primarily for personal hygiene containing lysine lauroylglycinate. - Google Patents

Detergent composition intended primarily for personal hygiene containing lysine lauroylglycinate. Download PDF

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Publication number
FR2699189A1
FR2699189A1 FR9215004A FR9215004A FR2699189A1 FR 2699189 A1 FR2699189 A1 FR 2699189A1 FR 9215004 A FR9215004 A FR 9215004A FR 9215004 A FR9215004 A FR 9215004A FR 2699189 A1 FR2699189 A1 FR 2699189A1
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France
Prior art keywords
lysine
detergent compositions
compositions according
sodium chloride
lauroylglycinate
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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.)
Granted
Application number
FR9215004A
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French (fr)
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FR2699189B1 (en
Inventor
Morelle Jean
Lauzanne Eliane
Rothfuss Jacqueline
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Individual
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Individual
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Publication date
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Priority to FR9215004A priority Critical patent/FR2699189B1/en
Priority to PCT/FR1993/001234 priority patent/WO1994013767A1/en
Priority to EP94902024A priority patent/EP0636165A1/en
Publication of FR2699189A1 publication Critical patent/FR2699189A1/en
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Publication of FR2699189B1 publication Critical patent/FR2699189B1/en
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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
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions

Abstract

Nouvelles compositions détergentes, principalement destinées à l'hygiène corporelle caractérisées en ce qu'elles comportent deux acides aminés sous forme de lauroylglycinate de lysine. De telles nouvelles compositions détergentes sont douées d'un important pouvoir moussant et nettoyant, d'une affinité particulière pour le revètement cutané et la chevelure ainsi que par des propriétés anti-radicalaires.New detergent compositions, mainly intended for personal hygiene, characterized in that they contain two amino acids in the form of lysine lauroylglycinate. Such new detergent compositions are endowed with an important foaming and cleaning power, with a particular affinity for the skin coating and the hair as well as with anti-free radical properties.

Description

On connais depuis longtemps des compositions détergentes destinés en particulier à l'hygiène corporelle comportant des acyl ats d'acides amines issus soit de l'hydrolyse partielle de protéines qui correspondent à des scylpeptides,soit de l'hydrolyse totale, conduisant a des acylpolyaminoacides; Acylpeptides comme acylpolyaminoacides entant salifies généralement par des bases minerai es, principalement la soude ou des bases organiques comme la triéthanolamine, la monoéthénolamine.Detergent compositions have been known for a long time, especially for body hygiene purposes, comprising acyl acids of amino acids derived either from the partial hydrolysis of proteins which correspond to scylpeptides or from total hydrolysis, leading to acylpolyamino acids; Acylpeptides as acylpolyaminoacids entant generally salified by mineral bases, mainly soda or organic bases such as triethanolamine, monoethenolamine.

il est également connu que la qualité moussante et nettoyante de ce type de tensio-actifs est inversement proportionnelle à la longueur de chaines polypeptides et au poids moléculaire des acides amines acylés.it is also known that the foaming and cleaning quality of this type of surfactant is inversely proportional to the length of polypeptide chains and the molecular weight of the acylated amino acids.

La réalisation de ce type de detergent nécessite un maternel onereux du fait de l'emploi d'acide chlorhydrique relativement concentre et de la durée de chauffage grevant le prix de revient du produit finalement obtenu. De plus, les produits ainsi réalisés à partir d'hydrolysats sont toujours doués d'une certaine odeur qu'il est nécessaire de masquer.The realization of this type of detergent requires expensive maternal because of the use of relatively concentrated hydrochloric acid and heating time on the cost of the product finally obtained. In addition, the products thus produced from hydrolysates are always endowed with a certain odor which it is necessary to mask.

La présente invention a pour objet de réaliser un détergent à usage hygiénique ou ménager caractérisé en ce qu'il comporte la plus petite molécule des acides aminésila glycine, acylée à la chaine laurique, L'acide laurylalycinique ainsi obtenu étant salifie. à la lysine,cette dernière issue du chlorhydrate de lysine, produit hautement industriel, utilisé pour l'alimentation du bétail.The object of the present invention is to provide a detergent for hygienic or household use, characterized in that it comprises the smallest molecule of amino acids, glycine, acylated with the lauric chain, the lauryl-orycinic acid thus obtained being salified. with lysine, the latter derived from lysine hydrochloride, a highly industrial product used for livestock feed.

La lauroylglycine est décrite dans la littérature en tant qu' acylaminoacide dont les rendements d'acylations ne dépassent pas 70 nécessitant l'extraction de l'acide gras libre, ce qui industriellement ne peut etre retenu.Lauroylglycine is described in the literature as an acylamino acid whose acylation yields do not exceed 70 requiring the extraction of free fatty acid, which industrially can not be retained.

Dans le cadre de l'invention ,on réalisera un lauroylglycine avec un rendement moyen de 90%, en opérant sel on le procédé ci-après:
Dans 400 ml d'eau,on dissout 30 g de glycine obtenue par synthèse, ajoute 100 ml d'alcool industriel .0n porte le pH à 10/ 10,5 on ont fait tomber goutte à soutte,sous agitation, 87 g de chlorure de lauroyle en maintenant le pH entre 10 et 10,5. lorsque tout le chlorure est introduit, on maintent l'agitation durant 30 minutes et la température au dessous de 30 .In the context of the invention, a lauroylglycine will be produced with an average yield of 90% by operating in the following process:
In 400 ml of water, 30 g of glycine obtained by synthesis are dissolved, 100 ml of industrial alcohol are added, the pH is brought to 10 / 10.5, 87 g of chloride are added dropwise with stirring. lauroyl by keeping the pH between 10 and 10.5. when all the chloride is introduced, stirring is maintained for 30 minutes and the temperature below 30.

Sous agitation, on ajoute de l'acide chlorhydrique à 33%, il se forme une matte volumineuse qui décante lorsque la température est voisine cie 75/L.00.0n vérifie que l'acylation est correcte par formol titration de la solution chorurés, qui ne doit pas accuser des teneurs en glycine non acylés.. With stirring, 33% hydrochloric acid is added, a voluminous matte is formed which decants when the temperature is close to 75 / L.000.0n verifies that the acylation is correct by formalin titration of the choridic solution, which must not show unacylated glycine levels.

La matte obtenue dont le poids est de 140 9 contient 25 à 30% d'eau
La structure lauroylglycine dont le P.F de la substance anhydre. est de 118-119 correspond à la formule et aux indices analytiques ci après:
CM3-(CH2)10-CO-HN-CH2-COOH
P,M = 257
Azote théorique: 5,4
trouvé: 4,9
Indice d'acide théorique: 217
trouvé: 225
On détermine la teneur exacte en extrait sec pour connaître la quantité de lysine nécessaire à la salification.The obtained matte weighing 140 9 contains 25 to 30% water
The lauroylglycine structure including the PF of the anhydrous substance. is 118-119 corresponds to the following formula and analytic indices:
CM3- (CH2) 10-CO-HN-CH2-COOH
P, M = 257
Nitrogen theoretical: 5.4
found: 4.9
Theoretical acid number: 217
found: 225
The exact content of dry extract is determined to determine the amount of lysine necessary for salification.

D'autre part,100 9 de chlorhydrate de lysine industriel sont traites par 100 ml d'eau déminéralisée et 70 ml de soude à 30%, a froid, sous agitation.0n obtient une solution colorée qui traitée sous asitation à froid également par 3% de noir décolorant conduit à 250 mi d'une solution pratiquement incolore.On the other hand, 100% of industrial lysine hydrochloride are treated with 100 ml of demineralised water and 70 ml of 30% sodium hydroxide under cold stirring. A colored solution is obtained which is also cold-treated. % black bleaching leads to 250 ml of a virtually colorless solution.

Le pH d'une telle solution se situe autour de 10,5;l 'acide chlorhydrique du chlorhydrate tant transformé en chlorure de sodium dont la teneur se situe entre 15 et 16 Cette solution continent en moyenne 35% de lysine hase.The pH of such a solution is around 10.5, the hydrochloric acid hydrochloride is converted into sodium chloride, the content of which is between 15 and 16 This solution has an average of 35% lysine.

Aux 140 9 d'acide lauroylglycinique hydraté, comportant 75 d'extrait sec, soit environ 100 g de lauroylglycinate de lysine anhydre, on ajoute :320 ml d'eau et 112 ml de solution de lysine réalisée comme ci dessus ,sous agitation et à une température d'environ 75/80 .On obtient ainsi 560 ml de solution détergente, dont l'extrait sec, se situe entre 24 et 25%, dont la teneur en chlorure de sodium qui assure la viscosité du milieu,se situe entre 3,5 et 4 et environ 20 de lauroylglycinate de lysine répondant à la structure suivante:
CH3-(CH2)10-CO-HN-CH2-COOH,CH2-(CH2)3-CH-COOH
NH2 NH2
P.M = 404
Azote théorique 10,5
Azote du produit contenant NaCl 8,5
La mise en évidence de cette structure s'effectue en traitant par
HCl. La sol titi on de lauroylglycinate de lysine contenant du NaCl. 140 g hydrolyzed lauroylglycinic acid, comprising 75 dry extract, or about 100 g anhydrous lysine lauroylglycinate, are added: 320 ml of water and 112 ml of lysine solution made as above, with stirring and a temperature of about 75/80. Thus 560 ml of detergent solution, the solids content of which is between 24 and 25%, the content of sodium chloride which ensures the viscosity of the medium, is between 3 and 5%. , 5 and 4 and about 20 of lysine lauroylglycinate having the following structure:
CH3- (CH2) 10-CO-HN-CH2-COOH, CH2- (CH2) 3-CH-COOH
NH2 NH2
PM = 404
Nitrogen theoretical 10.5
Nitrogen of the product containing NaCl 8.5
The highlighting of this structure is carried out by processing by
HCl. The soil is titrated with lysine lauroylglycinate containing NaCl.

l'acide lauroylglycinique précipite à froid,avec formation de chlorhydrate de lysine. Dans la solution on détermine la lysine par chromatoplaque Le précipité qui surnage en chauffant est lavé par de l'eau chaude puis traité par 50 d'HCL à 33% et porté à ébullition avec réfrigérant ascendant durant six heures.La chromatographie révèle cette fois le spot de la glycine. La chaine laurique qui est également libérée peut être extraite par l'ether de pétrole suivi de la mesure de l'indice d'acide. lauroylglycinic acid precipitates cold, with the formation of lysine hydrochloride. In the solution, the lysine is determined by chromatoplate. The precipitate, which is heated while supernatant, is washed with hot water and then treated with 50% of 33% HCl and boiled with ascending refrigerant for six hours. spot of glycine. The lauric chain that is also released can be extracted by petroleum ether followed by measurement of the acid number.

L'invention s'étend également à la salification partielle par la lysine, complétée par une base minérale ou organique, la présence de lysine ne pouvant être inférieure à 25 ou 30% des agents de salification L.a pressente invention est caractérisée par les avantages suivants:
Elle permet de réaliser un détergent physiologique comportant deux acides aminés dont un essentiel sans avoir recours à l'hydrolyse d'une proteine.The invention also extends to partial salification with lysine, supplemented with a mineral or organic base, the presence of lysine not being less than 25 or 30% of salification agents. The present invention is characterized by the following advantages:
It makes it possible to produce a physiological detergent comprising two amino acids, one of which is essential without resorting to the hydrolysis of a protein.

Elle utilise des acides aminés dits industriels économiquement accessibles pour la réalisation de ce type de détergent.It uses so-called economically accessible industrial amino acids for the realization of this type of detergent.

Elle permet de réaliser acylation et salification sans avoir recours à une installation onéreuse.It allows acylation and salification to be carried out without resorting to an expensive installation.

Elle permet d'obtenir un produit faiblement coloré et faiblement odorant
Elle permet d'obtenir un detergent physiologique à haut pouvoir nettoyant et moussant: Une solution comportant 4t de lauroylglycinate de lysine est encore douée d'un important pouvoir moussant et nettoyant
Le laurylglycinate de lysine est doué de propriétés antiradicalaires, mises en évidence par la décoloration de la Diphenyl picrylhydrazyl. It makes it possible to obtain a weakly colored and weakly odorous product
It makes it possible to obtain a physiological detergent with high cleaning and foaming power: A solution comprising 4% of lysine lauroylglycinate is still endowed with an important foaming and cleansing power.
Lysine laurylglycinate is endowed with antiradical properties, evidenced by the discoloration of Diphenyl picrylhydrazyl.

ce type d'acylaminoacides possède une affinité particulière pour la peau et la chevelure, conduisant à à la fixation d'un film protecteur. this type of acylamino acid has a particular affinity for the skin and the hair, leading to the fixing of a protective film.

Claims (2)

REVENDICATIONS 1-Nouvelles compositions détergentes, principalement destinées à l'hygiene corporelle,caractérisées en ce qu'elles comportent un acyl aminoaci de:l a i auroylglycine salifiée en partie ou en totalité par la Iysine,répondant à la formule suivante,lorsque la salification et totale: 1-New detergent compositions, mainly intended for body hygiene, characterized in that they comprise an acyl aminoacrylate of: 1 to 1 salyglycine salified in part or in whole by lysine, corresponding to the following formula, when salification and total: CH3-(CH2)10-CO-HN-CH2-COOH, H2N-CH2-(CH2)3-CH-COOH CH3- (CH2) 10-CO-HN-CH2-COOH, H2N-CH2- (CH2) 3-CH-COOH NH2 2-Nouvel les compositions détergentes sel on la revendication 1 caractérisées en ce qu'elles comportent comme agents de sali fi cati on au moi ns 25% de lysine.  NH 2 2 -New detergent compositions according to claim 1 characterized in that they comprise as agents of sali fi cation at least 25% lysine. :3-Compositions détergentes sel on les revendications 1 et 2 3-detergent compositions according to claims 1 and 2; Caractérisées en ce que,la lauroylglycine ne nécessite aucune purification du fait que son acylation est réalisée en présence d'un ai cool polaire, ce qui permet d'obtenir un rendement d'acylation de l'ordre de 90% 4-Compositions détersentes sel on les revendi cati ons 1 à 3 caractérisées en ce que la lysine est obtenue à partir du chlorhdrate de lysine;produit industriel utilisé pour l'alimentation du bétail. par depl acement de son chlorhydrate par la soude, conduisant ainsi à de la lysine libre en présence de chlorure de sodium.Characterized in that the lauroylglycine does not require any purification because its acylation is carried out in the presence of a polar cool, which makes it possible to obtain an acylation yield of the order of 90%. 4-Salt detersive compositions 1 to 3, characterized in that the lysine is obtained from lysine hydrochloride, an industrial product used for feeding cattle. by displacement of its hydrochloride by soda, thus leading to free lysine in the presence of sodium chloride. 5-Compositions détergentes selon les revendications 1 à 3,, caractérisée en ce que la i auroyl glycine n'est pas soumise à un lavage et contient de faibles quantités d'acide chlorhydrique donnant lieu également à du chlorure de sodium,lorsque la lysine base contient un exces de soude. Le chlorure de sodium etant avantageusement utilisé comme agent d'épaississement du milieu.5-detergent compositions according to claims 1 to 3, characterized in that the auroyl glycine is not subjected to washing and contains small amounts of hydrochloric acid also giving rise to sodium chloride, when the lysine base contains an excess of soda. Sodium chloride is advantageously used as a medium thickening agent. 6-Compositions détergentes sel on les revendications 1 à 3 caractérisées en ce qu'elles sont douées d'un pouvoir nettoyant et moussant particuilièrement important et par des propriétés anti radical aires, mises en Cvi dence par la décoloration de la di phényl pi cryhydrazyl  6-Detergent compositions according to claims 1 to 3 characterized in that they are endowed with a particularly important cleaning and foaming power and with anti-radical properties, brought about by the discoloration of the di phenyl pi cryhydrazyl
FR9215004A 1992-12-14 1992-12-14 Detergent composition intended mainly for personal hygiene containing lysine lauroylglycinate. Expired - Fee Related FR2699189B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR9215004A FR2699189B1 (en) 1992-12-14 1992-12-14 Detergent composition intended mainly for personal hygiene containing lysine lauroylglycinate.
PCT/FR1993/001234 WO1994013767A1 (en) 1992-12-14 1993-12-13 Detergent compositions containing lysine lauryglycinate
EP94902024A EP0636165A1 (en) 1992-12-14 1993-12-13 Detergent compositions containing lysine lauryglycinate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9215004A FR2699189B1 (en) 1992-12-14 1992-12-14 Detergent composition intended mainly for personal hygiene containing lysine lauroylglycinate.

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FR2699189A1 true FR2699189A1 (en) 1994-06-17
FR2699189B1 FR2699189B1 (en) 1995-01-27

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FR (1) FR2699189B1 (en)
WO (1) WO1994013767A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3246384A1 (en) * 2016-05-18 2017-11-22 Basf Se Aqueous tenside compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0460566A2 (en) * 1990-06-05 1991-12-11 Kao Corporation Detergent composition
WO1992021318A1 (en) * 1991-06-03 1992-12-10 Givaudan-Lavirotte N-acyl derivatives of amino acid mixtures derived from cereal protein hydrolysates and applications thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0460566A2 (en) * 1990-06-05 1991-12-11 Kao Corporation Detergent composition
WO1992021318A1 (en) * 1991-06-03 1992-12-10 Givaudan-Lavirotte N-acyl derivatives of amino acid mixtures derived from cereal protein hydrolysates and applications thereof

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Publication number Publication date
FR2699189B1 (en) 1995-01-27
EP0636165A1 (en) 1995-02-01
WO1994013767A1 (en) 1994-06-23

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