EP1083261A1 - Use of lipoaminoacids in making of paper products, and paper products containing them - Google Patents

Use of lipoaminoacids in making of paper products, and paper products containing them Download PDF

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Publication number
EP1083261A1
EP1083261A1 EP00402303A EP00402303A EP1083261A1 EP 1083261 A1 EP1083261 A1 EP 1083261A1 EP 00402303 A EP00402303 A EP 00402303A EP 00402303 A EP00402303 A EP 00402303A EP 1083261 A1 EP1083261 A1 EP 1083261A1
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Prior art keywords
weight
acid
formula
extract
paper
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German (de)
French (fr)
Inventor
Nelly Michel
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Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds

Definitions

  • the subject of the invention is a new use of N-acylated (oligo) amino acids.
  • N-acylated (oligo) amino acids also called lipoamino acids when the acyl radical is derived from a fatty acid, such as those described in international patent applications published under the numbers WO92 / 20647, WO92 / 21318, WO94 / 26694 and W094 / 27561, are commonly used in the preparation of cosmetic products.
  • a large number of quaternary ammonium derivatives have been used as a softening agent; they contain one or more fatty chains, whose number of carbon atoms is between 8 and 32 atoms of carbon.
  • the Applicant has sought to develop compounds which are incorporated into cellulose pulp or applied to the cellulosic product final, which give this product a soft and slippery feel, which does not cause no irritation when rubbing said product on the skin or mucous membranes, while not degrading its initial resistance to tearing or its capacity absorption of liquids.
  • composition comprising an effective amount of at least one compound of formula (I): or its topically acceptable salts, in which R represents the chain characterizing a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, R 1 or represents the chain or the cyclic radical characterizing an amino acid and m is between 1 and 5, for the manufacture of paper products.
  • R represents the chain characterizing a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms
  • non-woven papers or supports for sanitary use or household, the use of which involves direct contact with the skin or mucous membranes.
  • These include, for example, handkerchiefs, hand towels paper, toilet paper, paper towels, make-up wipes, paper or on non-woven backing.
  • topically acceptable salt any salt of the acid of formula (I) biologically acceptable for the skin and / or mucous membranes, say any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin.
  • They may especially be alkaline salts such as sodium, potassium or lithium salts, alkaline earth salts such as calcium, magnesium or strontium salts; it can also be salts metallic such as divalent salts of zinc, copper or manganese or also the trivalent salts of iron, lanthanum, cerium or aluminum or finally amine salts.
  • composition implementation in the use according to the invention may contain one or more of these compounds.
  • the compound (s) of formula (I) can be in the form of free acid or in partially or fully salified form.
  • characterizing chain used in the context of this patent application, designates the main non-functional chain of fatty acid or the amino acid under consideration.
  • the characterizing chain will be the linear or branched chain, represented by R.
  • Le radical R represents in particular a radical containing from 5 to 22 atoms of carbon chosen from pentyl, hexyl, heptyl, octyl, nonyl, decyl radicals, undecyle, dodecyle, tridécyle, tétra35cyle, pentadécyle, hexadécyle, heptadécyle, octadecyl, nonadecyl, eicosyl, unicosyl, docosyle, heptadecenyl, eicosenyl, unicosenyl, docosenyl or heptadecadienyl or decenyl.
  • the fragment R ⁇ CO comprises from 7 to 22 carbon atoms and represents in particular one of the radicals hexanoyl, heptanoyl, octanoyl (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyl), octadecanoyl (stearyl), eicosanoyle (arachidoyl), docosanoyl (behenoyl), octodecenoyl (oleyl), eicosenoyl (gadoloyl), docosènoyl (erucyle), octadécadiènoyl (linolènoyl)
  • an amino acid represented by the formula: will be characterized by the definition of the cyclic radical:
  • the chain or the cyclic radical characterizing the amino acid are chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine , lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine.
  • the present invention has for object a use as defined above, in which the one or more compounds of formula (I) contained in the composition used, are associated with at least one extract and / or tincture of plant material rich in tannin chosen from cinnamon, willow or witch hazel tea extracts.
  • the one or more compounds of formula (I) contained in the composition used are associated with at least one plant material extract chosen from extracts plants of the water lily family, and in particular with at least an extract of water lily flower such as "Nuphar japonicum", of lotus flower such as "Nelumbo nucifera” or "Brasenia purpurea”.
  • extracts are preparations concentrated, liquid, solid or intermediate in consistency, generally obtained from dried vegetable or animal raw materials.
  • tinctures are preparations generally obtained from dried vegetable or animal raw materials.
  • composition used in the invention includes commonly used mineral or organic vehicles such as by example water, polyols such as propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylglycol or glycerin.
  • polyols such as propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylglycol or glycerin.
  • composition used in the present invention can also include one or more neutralization bases, such as tris (trishydroxyaminométhane), triethanolamine, lysine or methyl glycine (sarcosine).
  • neutralization bases such as tris (trishydroxyaminométhane), triethanolamine, lysine or methyl glycine (sarcosine).
  • It can also include other compounds such as for example metal salts of organic anions such as, for example, aspartate magnesium and potassium and / or zinc gluconate.
  • the compounds of formula (I) are generally obtained by acylation of compounds of formula (I ') or their salts, themselves obtained by total or partial hydrolysis of proteins of all origins.
  • proteins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of plant origin, such as cereal, flower or fruit proteins, such as for example proteins from soybeans, sunflower , oats, wheat, corn, barley, potato, lupine, faba bean, sweet almond, kiwi, mango or apple; it can also be proteins obtained from chorelles (unicellular algae), pink algae, yeasts or silk.
  • R 1 represents several of the chains characterizing amino acids, depending on the hydrolyzed protein and the degree of hydrolysis.
  • m is less than 2 and is preferably equal to 1.
  • composition used in the use according to the invention comprises approximately from 15% to 60% and, more particularly approximately from 20% to 40% by weight, at least one compound of formula (I) as defined above.
  • she includes one or more extracts and / or tinctures of vegetable matter, contains approximately 0.1% to 10% and more particularly 0.5% to 5% by weight.
  • the extracts can be in the form fluid extracts, soft or firm extracts or dry extracts.
  • the weight percentages of constituents of the extract or of the dye corresponds to the percentages by weight of dry residue, said residue dry being obtained by evaporation of the solvent and drying of said extract or said dyeing under operating conditions at which the alteration of the constituents is minimal.
  • composition used comprises other compounds, such as that for example magnesium and potassium aspartate and / or gluconate of zinc, it generally contains from 0.1% to 10% and more particularly 0.5% to 5% by weight.
  • composition which is the subject of the present invention is prepared according to methods known to those skilled in the art, in general, by simple agitation of the mixture of its constituents in the appropriate liquid vehicle. If necessary or if desired, said extract and / or said tincture are previously diluted before mixing.
  • composition used is a solution aqueous comprising from about 6% to 10% by weight of N-lauroyl acid glutamic, from 3% to 8% by weight of N-lauroyl aspartic acid, from 2% to 5% by weight of N-lauroyl glycine, from 2 to 4% by weight of N-lauroyl alanine, from 0.5 to 2% by weight of mixed potassium and magnesium aspartate, from 20% to 25% in weight of propylene glycol and from 4% to 10% by weight of sarcosine, from 3% to 6% lauric acid.
  • composition used is an aqueous solution comprising from about 20% to 30% by weight of N-octanoyl glycine acid, from 3% weight of cinnamon extract ( Cinnamomum zelanicum ) from 5% to 15% by weight of glycerin, from 5% to 15% by weight of butylene glycol and from 4% to 10% by weight of sarcosine.
  • composition used is a solution aqueous comprising from about 20% to 30% by weight of N-undecenoyl acid glycine and from 5% to 15% by weight of glycerin.
  • composition used is a solution aqueous comprising from about 25% to 35% by weight of N-palmitoyl proline and 0.1% by weight of water lily flower extract (Nymphaea Alba).
  • composition used is a solution aqueous comprising approximately from 30% to 50% by weight of N-palmitoyl proline, 10% to 15% by weight of N-palmitoyl glutamic acid, from 10% to 15% by weight of N-palmitoyl sarcosine and from 25% to 35% by weight of palmitic acid.
  • composition used is a solution aqueous comprising from about 30% to 70% by weight of N-cocoyl glycine, from 0% 25% by weight of N-cocoyl sarcosine acid, and 5% to 20% by weight of the mixture fatty acids from coconut oil.
  • composition is used according to known methods of the skilled person. It can be applied or impregnated after dilution between about 2% and 5% by weight in a suitable liquid vehicle, for example of water or a polyol, on the paper product at a rate of about 0.3 grams to 15 grams of diluted solution per 100 grams of paper product.
  • a suitable liquid vehicle for example of water or a polyol
  • the product papermaker thus obtained, contains between about 0.0005% and 0.5% by weight of compound of formula (I) as defined above.

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  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

The use of lipoaminoacids (currently used in preparation of cosmetics) for production of paper articles. The patent refers to use of composition, comprising at least one compound of formula (I) (or its topically acceptable salts) R = 3-30C (un)saturated linear or branched fatty acid chain; R1 or (a) = chain or cyclic radical characteristic for aminoacid; m = 1-5, preferably 1 in production of paper articles. The compound(s) (I) contained in composition is (are) preferably associated with at least one extract and/or tincture of tannin-rich vegetable materials, such as extracts of cinnamon, willow or hamamelis (sic), or they can be associated with at least one extract of vegetable matter selected from extracts of plants from Nymphaeaces (water plants) family, especially extract of nenuphar Nuphar japonicum or Nymphaea Alba, or lotus Nelumbo nucifera or Brasenia purpurea. An Independent claim is also included for the paper product containing 0.0005-0.5 wt.% of one or more compounds of formula (I) as claimed.

Description

L'invention a pour objet, une nouvelle utilisation des (oligo)aminoacides N-acylés.The subject of the invention is a new use of N-acylated (oligo) amino acids.

Les (oligo)aminoacides N-acylés, appelés aussi, lipoaminoacides lorsque le radical acyle est dérivé d'un acide gras, comme par exemple ceux décrits dans les demandes internationales de brevet publiées sous les numéros WO92/20647, WO92/21318, WO94/26694 et W094/27561, sont couramment utilisés dans la préparation de produits cosmétiques.N-acylated (oligo) amino acids, also called lipoamino acids when the acyl radical is derived from a fatty acid, such as those described in international patent applications published under the numbers WO92 / 20647, WO92 / 21318, WO94 / 26694 and W094 / 27561, are commonly used in the preparation of cosmetic products.

La cellulose, quelle que soit sa forme, lorsqu'elle est traitée par des agents alcalins, des produits de blanchiment ou de lavage, acquiert un toucher sec, dur et peu agréable. C'est pourquoi, depuis de nombreuses années, on utilise des produits d'adoucissage ou d'assouplissage dans l'industrie papetière. On distingue de façon générale deux catégories de composés d'adoucissage ; il y a ceux qui sont incorporés directement dans la pâte de cellulose à papier et ceux qui sont appliqués en surface d'un produit cellulosique telle qu'une feuille de papier, que ce soit avant séchage ou après séchage dudit produit.Cellulose, whatever its form, when treated with agents alkaline, bleaching or washing products, acquires a dry, hard feel and unpleasant. This is why, for many years, we have been using softening or softening products in the paper industry. We generally distinguishes two categories of softening compounds; there is those which are incorporated directly into the pulp of paper pulp and those which are applied to the surface of a cellulosic product such as a sheet of paper, either before drying or after drying of said product.

Un grand nombre de dérivés d'ammonium quaternaire ont été utilisés comme agent d'adoucissage ; ils contiennent une ou plusieurs chaínes grasses, dont le nombre d'atomes de carbone est compris entre 8 et 32 atomes de carbone.A large number of quaternary ammonium derivatives have been used as a softening agent; they contain one or more fatty chains, whose number of carbon atoms is between 8 and 32 atoms of carbon.

La demanderesse a cherché à mettre au point des composés que l'on incorpore à la pâte de cellulose ou que l'on applique sur le produit cellulosique final, qui procurent à ce produit un toucher doux et glissant, qui ne provoquent pas d'irritations lors du frottement dudit produit sur la peau ou les muqueuses, tout en ne dégradant pas sa résistance initiale au déchirement ni sa capacité absorption des liquides.The Applicant has sought to develop compounds which are incorporated into cellulose pulp or applied to the cellulosic product final, which give this product a soft and slippery feel, which does not cause no irritation when rubbing said product on the skin or mucous membranes, while not degrading its initial resistance to tearing or its capacity absorption of liquids.

C'est pourquoi l'invention a pour objet l'utilisation d'une composition comprenant une quantité efficace d'au moins un composé de formule (I) :

Figure 00010001
ou ses sels topiquement acceptables, dans laquelle R représente la chaíne caractérisante d'un acide gras, saturé ou insaturé, linéaire ou ramifié, comportant de 3 à 30 atomes de carbone, R1 ou
Figure 00020001
représente la chaíne ou le radical cyclique caractérisant d'un aminoacide et m est compris entre 1 et 5, pour la fabrication de produits papetiers.This is why the subject of the invention is the use of a composition comprising an effective amount of at least one compound of formula (I):
Figure 00010001
or its topically acceptable salts, in which R represents the chain characterizing a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, R 1 or
Figure 00020001
represents the chain or the cyclic radical characterizing an amino acid and m is between 1 and 5, for the manufacture of paper products.

Par produits papetiers, on désigne tout particulièrement dans le cadre de la présente invention, les papiers ou supports non tissées à usage sanitaire ou domestique dont l'utilisation implique un contact direct avec la peau ou les muqueuses. Il s'agit par exemple, de mouchoirs en papier, d'essuie-mains en papier, de papier toilette, d'essuie-tout, de lingettes à démaquiller, en papier ou sur support non tissé.By paper products, we particularly mean in the context of present invention, non-woven papers or supports for sanitary use or household, the use of which involves direct contact with the skin or mucous membranes. These include, for example, handkerchiefs, hand towels paper, toilet paper, paper towels, make-up wipes, paper or on non-woven backing.

Par sel topiquement acceptable, on entend tout sel de l'acide de formule (I) biologiquement acceptable pour la peau et/ou les muqueuses, c'est à dire tout sel pouvant notamment régler le pH de la composition à une valeur comprise entre 3 et 8 et de préférence environ égale à 5, c'est à dire à un pH voisin de celui de la peau. Il peut s'agir notamment de sels alcalins tels que les sels de sodium, de potassium ou de lithium, de sels alcalino-terreux tels que les sels de calcium, de magnésium ou de strontium ; il peut aussi s'agir de sels métalliques tels que les sels divalents de zinc, de cuivre ou de manganèse ou encore les sels trivalents de fer, de lanthane, de cérium ou d'aluminium ou enfin de sels d'amines.By topically acceptable salt is meant any salt of the acid of formula (I) biologically acceptable for the skin and / or mucous membranes, say any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin. They may especially be alkaline salts such as sodium, potassium or lithium salts, alkaline earth salts such as calcium, magnesium or strontium salts; it can also be salts metallic such as divalent salts of zinc, copper or manganese or also the trivalent salts of iron, lanthanum, cerium or aluminum or finally amine salts.

Par au moins un composé de formule (I), on indique que la composition mise en oeuvre dans l'utilisation selon l'invention peut contenir un ou plusieurs de ces composés.By at least one compound of formula (I), it is indicated that the composition implementation in the use according to the invention may contain one or more of these compounds.

Le ou les composés de formule (I), peuvent être sous forme d'acide libre ou sous forme partiellement ou totalement salifiée. The compound (s) of formula (I) can be in the form of free acid or in partially or fully salified form.

L'expression "chaíne caractérisante" utilisée dans le cadre de la présente demande de brevet, désigne la chaíne principale non fonctionnelle de l'acide gras ou de l'acide aminé considéré.The expression "characterizing chain" used in the context of this patent application, designates the main non-functional chain of fatty acid or the amino acid under consideration.

Ainsi, pour un acide gras répondant à la formule générale R-COOH, la chaíne caractérisante sera la chaíne linéaire ou ramifiée, représentée par R. Le radical R représente notamment un radical comportant de 5 à 22 atomes de carbone choisi parmi les radicaux pentyle, hexyle, heptyle, octyle, nonyle, décyle, undécyle, dodécyle, tridécyle, tétradécyle, pentadécyle, hexadécyle, heptadécyle, octadécyle, nonadécyle, eicosyle, uneicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou décènyle. L'invention a plus particulièrement pour objet l'utilisation, telle que définie précédemment, dans laquelle, dans la formule (I), le fragment R―CO comporte de 7 à 22 atomes de carbone et représente notamment l'un des radicaux hexanoyle, heptanoyle, octanoyle (capryloyle), décanoyle (caproyle), undécylènoyle, dodécanoyle (lauroyle), tétradécanoyle (myristyle), hexadécanoyle (palmitoyle), octadécanoyle (stéaryle), eicosanoyle (arachidoyle), docosanoyle (behènoyle), octodécènoyle (oléyle), éicosènoyle (gadoloyle), docosènoyle (érucyle), octadécadiènoyle (linolènoyle).Thus, for a fatty acid corresponding to the general formula R-COOH, the characterizing chain will be the linear or branched chain, represented by R. Le radical R represents in particular a radical containing from 5 to 22 atoms of carbon chosen from pentyl, hexyl, heptyl, octyl, nonyl, decyl radicals, undecyle, dodecyle, tridécyle, tétradécyle, pentadécyle, hexadécyle, heptadécyle, octadecyl, nonadecyl, eicosyl, unicosyl, docosyle, heptadecenyl, eicosenyl, unicosenyl, docosenyl or heptadecadienyl or decenyl. A more particular subject of the invention is the use, as defined previously, in which, in formula (I), the fragment R ― CO comprises from 7 to 22 carbon atoms and represents in particular one of the radicals hexanoyl, heptanoyl, octanoyl (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyl), octadecanoyl (stearyl), eicosanoyle (arachidoyl), docosanoyl (behenoyl), octodecenoyl (oleyl), eicosenoyl (gadoloyl), docosènoyl (erucyle), octadécadiènoyl (linolènoyl).

Un aminoacide représenté par la formule générale H2N-CHR1-COOH, sera caractérisé par la définition de R1.An amino acid represented by the general formula H 2 N-CHR 1 -COOH, will be characterized by the definition of R 1 .

Un acide aminé représenté par la formule :

Figure 00030001
sera caractérisé par la définition du radical cyclique :
Figure 00030002
Dans le cadre de la présente invention, la chaíne ou le radical cyclique caractérisant l'aminoacide sont choisis parmi la glycine, l'alanine, la sérine, l'acide aspartique, l'acide glutamique, la valine, la thréonine, l'arginine, la lysine, la proline, la leucine, la phénylalanine, l'isoleucine, l'histidine, la tyrosine, le tryptophane, l'asparagine, la cystéine, la cystine, la méthionine, l'hydroxyproline, l'hydroxylysine et l'ornithine.An amino acid represented by the formula:
Figure 00030001
will be characterized by the definition of the cyclic radical:
Figure 00030002
In the context of the present invention, the chain or the cyclic radical characterizing the amino acid are chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine , lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine.

Selon un premier aspect particulier de la présente invention celle-ci a pour objet une utilisation telle que définie précédemment, dans laquelle le ou les composés de formule (I) contenus dans la composition mise en oeuvre, sont associés avec au moins un extrait et/ou teinture de matières végétale riche en tannin choisi parmi les extraits de thé de cannelle, de saule ou d'hamamélis.According to a first particular aspect of the present invention, it has for object a use as defined above, in which the one or more compounds of formula (I) contained in the composition used, are associated with at least one extract and / or tincture of plant material rich in tannin chosen from cinnamon, willow or witch hazel tea extracts.

Selon un deuxième aspect particulier de la présente invention celle-ci a pour objet l'utilisation telle que définie précédemment, dans laquelle le ou les composés de formule (I) contenus dans la composition mise en oeuvre, sont associés avec au moins un extrait de matières végétales choisi parmi les extraits de plantes de la famille des nymphéacées, et tout particulièrement avec au moins un extrait de fleur de nénuphar tel que "Nuphar japonicum", de lotus tel que "Nelumbo nucifera" ou de "Brasenia purpurea".According to a second particular aspect of the present invention, it has for object the use as defined above, in which the one or more compounds of formula (I) contained in the composition used, are associated with at least one plant material extract chosen from extracts plants of the water lily family, and in particular with at least an extract of water lily flower such as "Nuphar japonicum", of lotus flower such as "Nelumbo nucifera" or "Brasenia purpurea".

Dans les définitions précédentes, les mots extrait et teinture sont utilisés dans leurs sens respectifs, tels qu'ils sont établis dans l'édition de 1997 de la Pharmacopée européenne ; les extraits (extracts) sont des préparations concentrées, liquides, solides ou de consistance intermédiaire, généralement obtenues à partir de matières premières végétales ou animales séchées. Les teintures (tincturae) sont des préparations généralement obtenues à partir de matières premières végétales ou animales séchées.In the previous definitions, the words extract and tincture are used in their respective meanings, as set out in the 1997 edition of the European Pharmacopoeia; extracts are preparations concentrated, liquid, solid or intermediate in consistency, generally obtained from dried vegetable or animal raw materials. The tinctures (tincturae) are preparations generally obtained from dried vegetable or animal raw materials.

Outre les principes actifs, la composition mise en oeuvre dans l'invention, comprend des véhicules minéraux ou organiques couramment utilisés tel que par exemple l'eau, les polyols comme le propylèneglycol, le dipropylèneglycol, le butylèneglycol, le pentylèneglycol, l'hexylèneglycol, le caprylglycol ou la glycérine. In addition to the active principles, the composition used in the invention, includes commonly used mineral or organic vehicles such as by example water, polyols such as propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylglycol or glycerin.

La composition mise en oeuvre dans la présente invention, peut aussi comprendre une ou plusieurs bases de neutralisation, comme le tris(trishydroxyaminométhane), du triéthanolamine de la lysine ou du méthyl glycine (sarcosine).The composition used in the present invention can also include one or more neutralization bases, such as tris (trishydroxyaminométhane), triethanolamine, lysine or methyl glycine (sarcosine).

Elle peut aussi comprendre d'autres composés tels que par exemple des sels métalliques d'anions organiques tels que par exemple, l'aspartate de magnésium et de potassium et/ou le gluconate de zinc.It can also include other compounds such as for example metal salts of organic anions such as, for example, aspartate magnesium and potassium and / or zinc gluconate.

Les composés de formule (I) sont généralement obtenus par acylation de composés de formule (I')

Figure 00050001
ou de leurs sels, eux-mêmes obtenus par hydrolyse totale ou partielle de protéines de toutes origines Une telle méthode est connue de l'homme du métier Ces protéines peuvent être d'origine animale, telles que, par exemple, le collagène, l'élastine, la protéine de chair de poissons, la gélatine de poissons, la kératine ou la caséine, d'origine végétale, comme les protéines de céréales, de fleurs ou de fruits, telles que par exemple, les protéines issues du soja, du tournesol, de l'avoine, du blé, du maïs, de l'orge, de la pomme de terre, du lupin, de la féverole, de l'amande douce, du kiwi, de la mangue ou de la pomme ; il peut s'agir aussi de protéines obtenues à partir de chorelles (algues unicellulaires), d'algues roses, de levures ou de la soie. Quand m est supérieur à 1, R1 représente plusieurs des chaínes caractérisantes des acides aminés, selon la protéine hydrolysée et le degré d'hydrolyse.The compounds of formula (I) are generally obtained by acylation of compounds of formula (I ')
Figure 00050001
or their salts, themselves obtained by total or partial hydrolysis of proteins of all origins. Such a method is known to those skilled in the art. These proteins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of plant origin, such as cereal, flower or fruit proteins, such as for example proteins from soybeans, sunflower , oats, wheat, corn, barley, potato, lupine, faba bean, sweet almond, kiwi, mango or apple; it can also be proteins obtained from chorelles (unicellular algae), pink algae, yeasts or silk. When m is greater than 1, R 1 represents several of the chains characterizing amino acids, depending on the hydrolyzed protein and the degree of hydrolysis.

Dans une variante particulière de l'utilisation objet de la présente invention, dans la formule (I) représentant le ou les composés de formule (I) contenus dans la composition mise en oeuvre, m est inférieur à 2 et est de préférence égal à 1.In a particular variant of the use which is the subject of the present invention, in formula (I) representing the compound or compounds of formula (I) contained in the composition used, m is less than 2 and is preferably equal to 1.

La composition mise en oeuvre dans l'utilisation selon l'invention, comprend environ de 15% à 60% et, plus particulièrement environ de 20% à 40% en poids, d'au moins un composé de formule (I) tel que définie précédemment. Lorsqu'elle comprend un ou plusieurs extraits et/ ou teintures de matière végétale, elle en contient environ de 0,1% à 10% et plus particulièrement de 0,5% à 5% en poids.The composition used in the use according to the invention comprises approximately from 15% to 60% and, more particularly approximately from 20% to 40% by weight, at least one compound of formula (I) as defined above. When she includes one or more extracts and / or tinctures of vegetable matter, contains approximately 0.1% to 10% and more particularly 0.5% to 5% by weight.

Selon la Pharmacopée européenne, les extraits peuvent être sous forme d'extraits fluides, d'extraits mous ou fermes ou d'extraits secs. Dans la définition précédente, les pourcentages pondéraux en constituants de l'extrait ou de la teinture correspondent aux pourcentages pondéraux en résidu sec, ledit résidu sec étant obtenu par évaporation du solvant et dessiccation dudit extrait ou de ladite teinture à des conditions opératoires auxquelles l'altération des constituants est minime.According to the European Pharmacopoeia, the extracts can be in the form fluid extracts, soft or firm extracts or dry extracts. In the definition above, the weight percentages of constituents of the extract or of the dye corresponds to the percentages by weight of dry residue, said residue dry being obtained by evaporation of the solvent and drying of said extract or said dyeing under operating conditions at which the alteration of the constituents is minimal.

Lorsque la composition mise en oeuvre comprend d'autres composés, tels que par exemple l'aspartate de magnésium et de potassium et/ou le gluconate de zinc, elle en contient généralement de 0,1% à 10% et plus particulièrement de 0,5% à 5% en poids.When the composition used comprises other compounds, such as that for example magnesium and potassium aspartate and / or gluconate of zinc, it generally contains from 0.1% to 10% and more particularly 0.5% to 5% by weight.

La composition, objet de la présente invention est préparée selon des méthodes connues de l'homme du métier, en général, par simple agitation du mélange de ses constituants dans le véhicule liquide adéquat. Si nécessaire ou si désiré, ledit extrait et/ou la dite teinture sont préalablement dilués avant mélange.The composition which is the subject of the present invention is prepared according to methods known to those skilled in the art, in general, by simple agitation of the mixture of its constituents in the appropriate liquid vehicle. If necessary or if desired, said extract and / or said tincture are previously diluted before mixing.

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 6% à 10% en poids d'acide N-lauroyl glutamique, de 3% à 8% en poids d'acide N-lauroyl aspartique, de 2% à 5% en poids de N-lauroyl glycine, de 2 à 4% en poids de N-lauroyl alanine, de 0,5 à 2% en poids d'aspartate mixte de potassium et de magnésium, de 20% à 25% en poids de propylène glycol et de 4% à 10% en poids de sarcosine, de 3% à 6% d'acide laurique.A more particular subject of the invention is the use as defined previously, in which the composition used is a solution aqueous comprising from about 6% to 10% by weight of N-lauroyl acid glutamic, from 3% to 8% by weight of N-lauroyl aspartic acid, from 2% to 5% by weight of N-lauroyl glycine, from 2 to 4% by weight of N-lauroyl alanine, from 0.5 to 2% by weight of mixed potassium and magnesium aspartate, from 20% to 25% in weight of propylene glycol and from 4% to 10% by weight of sarcosine, from 3% to 6% lauric acid.

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 20% à 30% en poids d'acide N-octanoyl glycine, de 3% en poids d'extrait de cannelle (Cinnamomum zelanicum) de 5% à 15% en poids de glycérine, de 5% à 15% en poids de butylène glycol et de 4% à 10% en poids de sarcosine. A more particular subject of the invention is the use as defined above, in which the composition used is an aqueous solution comprising from about 20% to 30% by weight of N-octanoyl glycine acid, from 3% weight of cinnamon extract ( Cinnamomum zelanicum ) from 5% to 15% by weight of glycerin, from 5% to 15% by weight of butylene glycol and from 4% to 10% by weight of sarcosine.

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 20% à 30% en poids d'acide N-undécènoyl glycine et de 5% à 15% en poids de glycérine.A more particular subject of the invention is the use as defined previously, in which the composition used is a solution aqueous comprising from about 20% to 30% by weight of N-undecenoyl acid glycine and from 5% to 15% by weight of glycerin.

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 25% à 35% en poids de N-palmitoyl proline et 0,1% en poids d'extrait de fleur de nénuphar (Nymphaea Alba).A more particular subject of the invention is the use as defined previously, in which the composition used is a solution aqueous comprising from about 25% to 35% by weight of N-palmitoyl proline and 0.1% by weight of water lily flower extract (Nymphaea Alba).

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 30% à 50% en poids de N-palmitoyl proline, de 10% à 15% en poids d'acide N-palmitoyl glutamique, de 10% à 15% en poids de N-palmitoyl sarcosine et de 25% à 35% en poids d'acide palmitique.A more particular subject of the invention is the use as defined previously, in which the composition used is a solution aqueous comprising approximately from 30% to 50% by weight of N-palmitoyl proline, 10% to 15% by weight of N-palmitoyl glutamic acid, from 10% to 15% by weight of N-palmitoyl sarcosine and from 25% to 35% by weight of palmitic acid.

L'invention a plus particulièrement pour objet, l'utilisation telle que définie précédemment, dans laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 30% à 70% en poids de N-cocoyl glycine, de 0% à 25% en poids d'acide N-cocoyl sarcosine, et 5% à 20% en poids du mélange d'acides gras issus de l'huile de coprah.A more particular subject of the invention is the use as defined previously, in which the composition used is a solution aqueous comprising from about 30% to 70% by weight of N-cocoyl glycine, from 0% 25% by weight of N-cocoyl sarcosine acid, and 5% to 20% by weight of the mixture fatty acids from coconut oil.

La composition est mise en oeuvre selon des méthodes connues de l'homme du métier. Elle peut être appliquée ou imprégnée après dilution entre environ 2% et 5% en poids dans un véhicule liquide appropriée, par exemple de l'eau ou un polyol, sur le produit papetier à raison d'environ 0,3 grammes à 15 grammes de solution diluée pour 100 grammes de produit papetier. Le produit papetier ainsi obtenu, contient entre environ 0,0005% et 0,5% en poids de composé de formule (I) telle que défini précédemment.The composition is used according to known methods of the skilled person. It can be applied or impregnated after dilution between about 2% and 5% by weight in a suitable liquid vehicle, for example of water or a polyol, on the paper product at a rate of about 0.3 grams to 15 grams of diluted solution per 100 grams of paper product. The product papermaker thus obtained, contains between about 0.0005% and 0.5% by weight of compound of formula (I) as defined above.

L'exemple suivant illustre l'invention sans toutefois la limiter.

  • A) On a préparé une composition comprenant environ 45% en poids de N-palmitoyl proline, de 10% à 15% en poids d'acide N-palmitoyl glutamique, de 10% à 15% en poids de N-palmitoyl sarcosine et 30% en poids d'acide palmitique.
  • B) On dilue cette composition à 3% dans une solution aqueuse à 20% de butylèneglycol.
  • C) on pulvérise finement cette solution à raison de 10 grammes de solution pour 100g de papier, sur les deux faces de deux cents mouchoirs en papier disponibles dans le commerce, préalablement dépliés. On laisse les laisse sécher 24 heures, sous air sec à 40°C, puis on replie les mouchoirs et une fois les deux cents mouchoirs ainsi préparés, on réalise un test sensoriel avec un panel de 20 personnes.
    • The following example illustrates the invention without however limiting it.
  • A) A composition was prepared comprising approximately 45% by weight of N-palmitoyl proline, from 10% to 15% by weight of N-palmitoyl glutamic acid, from 10% to 15% by weight of N-palmitoyl sarcosine and 30 % by weight of palmitic acid.
  • B) This composition is diluted to 3% in a 20% aqueous solution of butylene glycol.
  • C) this solution is finely sprayed at the rate of 10 grams of solution per 100g of paper, on the two sides of two hundred commercially available handkerchiefs, previously unfolded. They are left to dry for 24 hours, in dry air at 40 ° C., then the tissues are folded and once the two hundred tissues thus prepared, a sensory test is carried out with a panel of 20 people.

    • Les appréciations du panel ont porté sur la sensation de douceur au toucherThe panel's assessments focused on the feeling of softness to touch

    On a distribué à chacune des 20 personnes du panel, vingt mouchoirs en papier parmi lesquels seulement 10 avaient été traités comme décrit ci-dessus. On leur a ensuite demandé de séparer les mouchoirs en cinq catégories, selon qu'ils leur paraissaient :

  • très doux au toucher (++++)
  • doux au toucher (+++)
  • plutôt rêches au toucher (---)
  • très rêches au toucher(----)
  • inclassables (0)
    • Twenty facial tissues were distributed to each of the 20 people on the panel, of which only 10 had been treated as described above. They were then asked to separate the handkerchiefs into five categories, depending on how they felt:
  • very soft to the touch (++++)
  • soft to the touch (+++)
  • rather rough to the touch (---)
  • very rough to the touch (----)
  • unclassifiable (0)

    • les résultats sont les suivants :the results are as follows:

    14 personnes sur les 20 du panel, ont classé l'ensemble des mouchoirs traités dans les catégories (++++) ou (+++) et l'ensemble des mouchoirs non traités dans les catégories (0), (---) ou (----).14 people out of the 20 on the panel classified all of the handkerchiefs treated in categories (++++) or (+++) and all tissues not treated in categories (0), (---) or (----).

    Claims (15)

    Utilisation d'une composition comprenant une quantité efficace d'au moins un composé de formule (I) :
    Figure 00090001
    ou ses sels topiquement acceptables, dans laquelle R représente la chaíne caractérisante d'un acide gras, saturé ou insaturé, linéaire ou ramifié, comportant de 3 à 30 atomes de carbone, R1 ou
    Figure 00090002
    représente la chaíne ou le radical cyclique caractérisant d'un aminoacide et m est compris entre 1 et 5, pour la fabrication de produits papetiers.    Use of a composition comprising an effective amount of at least one compound of formula (I):
    Figure 00090001
    or its topically acceptable salts, in which R represents the chain characterizing a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, R 1 or
    Figure 00090002
    represents the chain or the cyclic radical characterizing an amino acid and m is between 1 and 5, for the manufacture of paper products.         Utilisation telle que définie à la revendication 1, pour la fabrication de papiers à usage sanitaire ou domestique dont l'utilisation implique un contact direct avec la peau ou les muqueuses.Use as defined in claim 1, for the manufacture sanitary or domestic papers, the use of which involves contact direct with the skin or mucous membranes. Utilisation telle que définie à la revendication 2 pour la fabrication de mouchoirs en papier, d'essuie-mains en papier, de papier toilette, d'essuie-tout, de lingettes à démaquiller en papier ou sur support non tissé.Use as defined in claim 2 for the manufacture of handkerchiefs, paper towels, toilet paper, paper towels, cleansing wipes made of paper or on a non-woven support. Utilisation telle que définie à l'une des revendications 1 à 3, pour laquelle, dans la formule (I), le fragment R―CO représente un des radicaux chois parmi les radicaux hexanoyle, heptanoyle, octanoyle (capryloyle), décanoyle (caproyle), undécylènoyle, dodécanoyle (lauroyle), tétradécanoyle (myristyle), hexadécanoyle (palmitoyle), octadécanoyle (stéaryle), eicosanoyle (arachidoyle), docosanoyle (behènoyle), octodécènoyle (oléyle), éicosènoyle (gadoloyle), docosènoyle (érucyle), octadécadiènoyle (linolènoyle).Use as defined in one of claims 1 to 3, for which, in formula (I), the fragment R ― CO represents one of the radicals chosen among the hexanoyl, heptanoyl, octanoyl (capryloyl) and decanoyl radicals (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyl), octadecanoyl (stearyl), eicosanoyle (arachidoyl), docosanoyl (behenoyl), octodecenoyl (oleyl), eicosenoyl (gadoloyl), docosènoyl (erucyle), octadécadiènoyl (linolènoyl). Utilisation telle que définie à la revendication 1 à 4, pour laquelle, dans la formule (I), la chaíne ou le radical cyclique caractérisant l'aminoacide, sont choisis parmi ceux de la glycine, l'alanine, la sérine, l'acide aspartique, l'acide glutamique, la valine, la thréonine, l'arginine, la lysine, la proline, la leucine, la phénylalanine, l'isoleucine, l'histidine, la tyrosine, le tryptophane, l'asparagine, la cystéine, la cystine, la méthionine, l'hydroxyproline, l'hydroxylysine et l'ornithine.Use as defined in claims 1 to 4, for which, in formula (I), the chain or the cyclic radical characterizing the amino acid, are chosen from those of glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine. Utilisation telle que définie à l'une des revendications 1 à 5, pour laquelle, le ou les composés de formule (I) contenus dans la composition mise en oeuvre, sont associés avec au moins un extrait et/ou teinture de matières végétale riche en tannin choisi parmi les extraits de thé de cannelle, de saule ou d'hamamélis.Use as defined in one of claims 1 to 5, for which, the compound (s) of formula (I) contained in the composition work, are associated with at least one extract and / or tincture of vegetable matter rich in tannin chosen from cinnamon, willow or tea extracts witch hazel. Utilisation telle que définie à l'une des revendications 1 à 6, pour laquelle le ou les composés de formule (I) contenus dans la composition mise en oeuvre, sont associés avec au moins un extrait de matières végétales choisi parmi les extraits de plantes de la famille des nymphéacées, et tout particulièrement avec au moins un extrait de fleur de nénuphar tel que "Nuphar japonicum" ou "Nymphaea Alba", de lotus tel que "Nelumbo nucifera" ou de "Brasenia purpurea".Use as defined in one of claims 1 to 6, for which the compound or compounds of formula (I) contained in the composition used, are associated with at least one extract of plant materials chosen from extracts of plants of the family of water lilies, and in particular with at least one extract of water lily flower such as "Nuphar japonicum" or " Nymphaea Alba ", of lotus such as " Nelumbo nucifera " or " Brasenia purpurea ". Utilisation telle que définie à l'une des revendications 1 à 7, pour laquelle, dans la formule (I), m est inférieur à 2 et est de préférence égal à 1.Use as defined in one of claims 1 to 7, for which, in formula (I), m is less than 2 and is preferably equal to 1. Utilisation telle que définie à l'une des revendications 1 à 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 6% à 10% en poids d'acide N-lauroyl glutamique, de 3% à 8% en poids d'acide N-lauroyl aspartique, de 2% à 5% en poids de N-lauroyl glycine, de 2 à 4% en poids de N-lauroyl alanine, de 0,5 à 2% en poids d'aspartate mixte de potassium et de magnésium, de 20% à 25% en poids de propylène glycol et de 4% à 10% en poids de sarcosine, de 3% à 6% d'acide laurique.Use as defined in one of claims 1 to 8, for which the composition used is an aqueous solution comprising about 6% to 10% by weight of N-lauroyl glutamic acid, from 3% to 8% by weight of N-lauroyl aspartic acid, from 2% to 5% by weight of N-lauroyl glycine, 2 to 4% by weight of N-lauroyl alanine, from 0.5 to 2% by weight of mixed aspartate potassium and magnesium, from 20% to 25% by weight of propylene glycol and 4% to 10% by weight of sarcosine, 3% to 6% of lauric acid. Utilisation telle que définie à l'une des revendications 6 ou 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 20% à 30% en poids d'acide N-octanoyl glycine, de 3% en poids d'extrait de cannelle (Cinnamomum zelanicum) de 5% à 15% en poids de glycérine, de 5% à 15% en poids de butylène glycol et de 4% à 10% en poids de sarcosine. Use as defined in either of claims 6 or 8, for which the composition used is an aqueous solution comprising approximately from 20% to 30% by weight of N-octanoyl glycine acid, from 3% by weight of cinnamon extract ( Cinnamomum zelanicum ) from 5% to 15% by weight of glycerin, from 5% to 15% by weight of butylene glycol and from 4% to 10% by weight of sarcosine. Utilisation telle que définie à l'une des revendications 1 à 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 20% à 30% en poids d'acide N-undécènoyl glycine et de 5% à 15% en poids de glycérine.Use as defined in one of claims 1 to 8, for which the composition used is an aqueous solution comprising approximately from 20% to 30% by weight of N-undecenoyl glycine acid and from 5% to 15% by weight of glycerin. Utilisation telle que définie à l'une des revendications 7 ou 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 25% à 35% en poids de N-palmitoyl proline et 0,1% en poids d'extrait de fleur de nénuphar (Nymphaea Alba).Use as defined in one of claims 7 or 8, for which the composition used is an aqueous solution comprising about 25% to 35% by weight of N-palmitoyl proline and 0.1% by weight of extract of water lily flower (Nymphaea Alba). Utilisation telle que définie à l'une des revendications 1 à 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 30% à 50% en poids de N-palmitoyl proline, de 10% à 15% en poids d'acide N-palmitoyl glutamique, de 10% à 15% en poids de N-palmitoyl sarcosine et de 25% à 35% en poids d'acide palmitique.Use as defined in one of claims 1 to 8, for which the composition used is an aqueous solution comprising about 30% to 50% by weight of N-palmitoyl proline, from 10% to 15% by weight N-palmitoyl glutamic acid, 10% to 15% by weight of N-palmitoyl sarcosine and from 25% to 35% by weight of palmitic acid. Utilisation telle que définie à l'une des revendications 1 à 8, pour laquelle la composition mise en oeuvre est une solution aqueuse comprenant environ de 30% à 70% en poids de N-cocoyl glycine, de 0% à 25% en poids d'acide N-cocoyl sarcosine, et 5% à 20% en poids du mélange d'acides gras issus de l'huile de coprah.Use as defined in one of claims 1 to 8, for which the composition used is an aqueous solution comprising about 30% to 70% by weight of N-cocoyl glycine, from 0% to 25% by weight of N-cocoyl sarcosine acid, and 5% to 20% by weight of the mixture of fatty acids derived coconut oil. Produits papetier à base de fibres papetières, caractérisé en ce qu'il comprend entre environ 0,0005% et 0,5% en poids d'une ou plusieurs composés de formule (I), telle que définie à l'une des revendications 1 à 8.Paper products based on paper fibers, characterized in that it comprises between about 0.0005% and 0.5% by weight of one or more compounds of formula (I), as defined in one of claims 1 to 8.
    EP00402303A 1999-09-08 2000-08-17 Use of lipoaminoacids in making of paper products, and paper products containing them Withdrawn EP1083261A1 (en)

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    FR9911221 1999-09-08

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    Cited By (1)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    US9511144B2 (en) 2013-03-14 2016-12-06 The Proctor & Gamble Company Cosmetic compositions and methods providing enhanced penetration of skin care actives

    Citations (2)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    EP0139481A2 (en) * 1983-09-22 1985-05-02 Ajinomoto Co., Inc. Surface modification using N-acyl lysines
    WO1994026694A1 (en) * 1993-05-17 1994-11-24 Givaudan Lavirotte Method for the preparation of n-acylated aminoacids

    Patent Citations (2)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    EP0139481A2 (en) * 1983-09-22 1985-05-02 Ajinomoto Co., Inc. Surface modification using N-acyl lysines
    WO1994026694A1 (en) * 1993-05-17 1994-11-24 Givaudan Lavirotte Method for the preparation of n-acylated aminoacids

    Cited By (1)

    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    US9511144B2 (en) 2013-03-14 2016-12-06 The Proctor & Gamble Company Cosmetic compositions and methods providing enhanced penetration of skin care actives

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