EP1945677A1 - Aus dem pfropfen von fettketten auf ulvane resultierendes produkt und verwendung des produkts als tensid - Google Patents

Aus dem pfropfen von fettketten auf ulvane resultierendes produkt und verwendung des produkts als tensid

Info

Publication number
EP1945677A1
EP1945677A1 EP06820311A EP06820311A EP1945677A1 EP 1945677 A1 EP1945677 A1 EP 1945677A1 EP 06820311 A EP06820311 A EP 06820311A EP 06820311 A EP06820311 A EP 06820311A EP 1945677 A1 EP1945677 A1 EP 1945677A1
Authority
EP
European Patent Office
Prior art keywords
product
transesterification
solvent
fatty
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06820311A
Other languages
English (en)
French (fr)
Inventor
Michèle Ranson
Gilles Gutierrez
Dominique Brault
Hervé LE DEIT
Xavier Pages-Xatart-Pares
Carine Alfos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JAVENECH
Environmental Protection Engineering Sa
ICP Institute for Cellular Pharmacology
Original Assignee
JAVENECH
Environmental Protection Engineering Sa
ICP Institute for Cellular Pharmacology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JAVENECH, Environmental Protection Engineering Sa, ICP Institute for Cellular Pharmacology filed Critical JAVENECH
Publication of EP1945677A1 publication Critical patent/EP1945677A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91—Graft copolymers
    • 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

Definitions

  • the present invention relates to novel ulvan derivatives, their methods of preparation and their uses, especially as surfactants.
  • Seaweed is known to be an important source of polysaccharides with gelling and thickening properties, widely used for food and non-food purposes. Ulvans are extracted from ulvae or enteromorphs. These green algae are part of the phyllum chlorophytes and order ulvals characterized by a thallus tube (enteromorph) or double layer cell (ulva). There are several ulva species including Ulva lactuca, Ulva rigida, Ulva armoricana and Ulva rotundata, as well as several enteromorph species such as Enteromorpha compressa, Enteromorpha intestinalis and
  • a fresh or dried seaweed is crushed then dissolved in water and refluxed for one hour.
  • the suspension is then centrifuged and reextracted a second time according to the same protocol.
  • the two supernatants are then combined and the ulvans are precipitated with ethanol. After filtration, the ulvans are then dried in an oven.
  • the yields are of the order of 10% relative to the dry matter of the starting algae.
  • Ulvans are sulfated anionic polysaccharides soluble in water. They are located at the level of the cell in the cell wall.
  • ulvans are of the family of sulfated xyloramnoglucoronan or sulfated glucoronorhamnoxyloglycan.
  • the sugars in the composition of ulvans are sulphated rhamnose in position 3, galactose, glucose and xylose for neutral sugars and glucuronic acid and iduronic acid for acid sugars.
  • the xylose may be partially sulphated.
  • the relative proportion of sugars varies according to the place of harvest of the ulva, the species and also the time of harvest in the year.
  • the following table shows the levels of sugars found in different species of ulva:
  • Green algae of the ulva family including the species produced by green tides, contain ulvans, which are water-soluble complex polysaccharides comprising both uronic acids and sulphated monosaccharides.
  • the chemical structure of ulvans is based on the repetition of different disaccharide units.
  • the disaccharide units are predominantly composed of 3-sulfate sodium ulvanobiuronate type A comprising 3-sulfate rhamnose bound to glucuronic acid by a 1 ⁇ 4 type binding and sodium 3-sulfate sodium ulvanobiuronate comprising 3-sulphate rhamnose bound to Iduronic acid by a type 1 ⁇ 4 bond:
  • the two disaccharide units are shown below.
  • the polysaccharide may also carry side chains whose structure has not been clearly identified.
  • an additional advantage of the invention is to value a product usually considered a nuisance.
  • the invention provides novel products which result directly from grafting by esterification or transesterification of fatty chains on ulvans.
  • the particularly advantageous properties of the products of the invention make it possible to envisage their use in many fields, as surface-active agents, in particular with a view to the preparation of emulsions.
  • properties are particularly interesting in various fields, especially in the field of cosmetics, because of the particularly soft and substantive touch of these products as well as their emulsifying and moisturizing properties, but also in totally different areas such as the recovery or dispersion of hydrocarbons.
  • the invention relates to a product resulting from grafting by esterification or transesterification on at least part of the hydroxyl functions of an ulvane-type polysaccharide in acid form or in the form of a salt.
  • a mono- or divalent cation especially a sodium salt of fatty chains or mixtures of fatty chains containing 8 to 28 carbon atoms, said fatty chains being saturated or unsaturated, linear or branched.
  • polyose-ester is derived from the reaction of polysaccharides (ulvans) extracted from algae of the ulva or enteromorphic type or from mixtures of these two types of algae with compounds comprising fatty chains containing between 8 and 28 carbon atoms, these chains may be saturated or unsaturated, linear or branched.
  • the extracts used according to the invention are advantageously prepared by extraction in aqueous medium of ulva and / or enteromorphs, the extraction step being advantageously followed by an ultrafiltration step.
  • grafting rate of the fatty chains on the ulvan skeleton is meant in the sense of the invention, the proportion by weight of fatty acid relative to the starting polyose.
  • each R group representing either a carboxylated fatty chain or a hydrogen and being independent of the others, as long as the disaccharide unit contains at least one fatty chain.
  • this process comprises an esterification or transesterification step using at least a part of the hydroxyl functions of an ulvane-type polysaccharide or of one of its salts obtained by extraction from a type of algae. ulve.
  • This process may be envisaged, in particular to take into account the specific character of the backbone on which it is desired to graft the fatty chains and the degree of grafting that it is desired to achieve, a rate which may vary in particular with the field of application. referred.
  • the various processes developed by the inventors of the present invention are all inspired by methods described in the literature taking into account both the specific character of the polysaccharide substrate and the intended application which may require more or less purity. important product and / or a grafting rate of fatty chains more or less important on the polysaccharide backbone.
  • the grafting will be carried out by esterification, in particular by means of an acid chloride of a fatty-chain acid comprising from 8 to 28 carbon atoms.
  • esterification in particular by means of an acid chloride of a fatty-chain acid comprising from 8 to 28 carbon atoms.
  • Such a method has the advantage of being able to prepare highly grafted products in which the proportion by weight of fatty acid relative to the polyose is at least 10%, preferably between 50 and 75%.
  • a process proceeding by transesterification a process that can be carried out under milder conditions while respecting the skeleton particularly well, which allows to access products, of superior purity, thus not colored.
  • the preparation of the products of the invention is preferably used for a transesterification process.
  • This transesterification will advantageously be carried out starting from esters of C8 to C28 fatty acids and of C1 to C6 alcohols or of mixtures of such esters and will make it possible to graft the fatty chains originating from said esters by means of a ester-type bond on at least a portion of the hydroxyl groups of ulvan.
  • fatty esters which can be used to carry out such a transesterification
  • esters may have different sources, in particular plant or animal sources.
  • the transesterification may be carried out in a solvent medium.
  • solvents used in such a transesterification process mention may be made of dimethylsulfoxide, diethylsulfoxide, dibutylsulfoxide, dibenzylsulfoxide, N, N-dimethylformamide, N, N-diethylformamide and N, N-diphenylformamide. .
  • the solvent used to carry out the transesterification will then have to be removed, for example by evaporation. The removal of the solvent will have to be more or less total, depending on the intended use for the product of the invention.
  • the product may be prepared by transesterification without a solvent.
  • Such a process proves to be significantly more advantageous than the previous one for industrial purposes since it is less expensive and avoids the problems related to the use of the solvent and the need, in certain cases, to eliminate all of the solvent.
  • non-solvent transesterification processes developed in the context of the present invention are based on the processes described in US Pat. Nos. 4,517,360 and 963,699, but have required a number of related adaptations. in particular to the nature of the specific substrate used for the grafting of the ester functions in the case of the products of the invention.
  • transesterification in a non-solvent medium is meant within the meaning of the invention that the reaction, itself, transesterification is carried out in the absence of solvent.
  • the recovery of the product formed during the reaction will require the use of at least one solvent medium in one or more extraction steps, as is apparent from the detailed description which follows.
  • the transesterification process without solvent is advantageously carried out by bringing the polysaccharide into contact with at least one fatty ester as defined above and at least one compound based on soaps, advantageously at least one compound based on alkaline metal fatty acid soaps saturated or unsaturated.
  • alkali metal soaps of fatty acids is meant alkali metal soaps of fatty acids having from 8 to 22 carbon atoms.
  • alkali metal soaps of fatty acids are in particular the sodium, lithium, potassium, rubidium and cesium salts of capric, lauric, oleic, myristic, palmitic, licanic, parinaric, arachidic or stearic acids, and as their mixtures.
  • the reagents described above for the preparation of the transesterification product form a heterogeneous mixture. The precise ratios of reagents can be freely determined either by experimentation or with the aid of the examples given below.
  • the starting reagent mixture comprises from about 5% to about 75%, preferably from about 15% to about 35% by weight of polyoses derived from ulva, from about 20% to about 90%, preferentially from about 40% to about 70% by weight of fatty acid esters and from about 1% to about 35%, preferably from about 10% to about 20% by weight of alkali metal fatty acid soaps.
  • the heterogeneous mixture is heated at a temperature advantageously between about 70 ° C. and about 180 ° C., preferably between about 100 ° C. and 150 ° C. under a pressure of about 0.1 mm of mercury to about 760 mm of mercury, preferably of 0.5 to 100 mm of mercury.
  • a homogeneous mixture of partially or fully esterified polyoses and unreacted starting reagents is formed after a time varying from about 1 hour to 18 hours, preferably a time varying from about 4 hours to 10 hours.
  • This solvent makes it possible to form a more fluid organic phase.
  • the amount of solvents to be added depends greatly on the viscosity of the reaction medium at the end of the reaction step.
  • the reaction medium is then acidified.
  • hydrochloric acid sulfuric acid
  • citric acid citric acid
  • lactic acid citric acid
  • acetic acid formic acid and mixtures thereof.
  • the gel formed is separated from the reaction medium and, if necessary, it can be dried by conventional drying techniques to give a family of polyose-esters.
  • the family of polyose-esters thus obtained is characterized by compounds with a fatty ester / polyose proportion which, for example, may be between 5 and 85% by weight, preferably between 25 and 70%. These products are easily soluble in water and give compounds with interesting properties, including moisturizing, emulsifying, co-emulsifying and imparting a soft and substantive touch in solution.
  • the transesterification method in a non-solvent medium as defined above makes it possible to recover at least a portion of the polyose-esters formed in the transesterification reaction in the form of an aqueous gel.
  • This method has the advantage of being particularly simple.
  • This additional extraction step intended for better recovery of all the polyosesters-esters formed will be particularly advantageous when the fatty chains are long or when the degree of grafting of these chains on the polysaccharide backbone is high. This will be particularly the case when the acid chains will have 16 or more carbon atoms or when the degree of grafting will be greater than or equal to 30%.
  • a method identical to that described above in which the transesterification is carried out in a non-solvent medium, preferably in the presence of at least one metallic soap, is carried out first of all as defined above. -above. Then, as in the previous method, the metal soap is removed and the viscosity of the medium is adjusted before precipitating a first family of polyose-esters in gel form. Then, the gel formed is separated from the reaction medium and, if necessary, it can be dried by conventional drying techniques and thus gives a first family of polyose-esters.
  • the remaining reaction medium is washed one or more times with water and the washings are extracted with a solvent of alcohol type partially soluble in water or insoluble in water, for example 1-butanol, 2 butanol, pentanol, hexanol, cyclohexanol.
  • the alcoholic phase is then dried and gives a second family of polyosesters, which has a grafting rate higher than that of the first.
  • the first family of polyose-esters is characterized by less grafted compounds, where, by way of example, the proportion fatty ester / polyose can be between 5 and 75% by weight, preferably between 20 and 60%.
  • This family is more hydrophilic and gives compounds with interesting properties, including emulsifying, co-emulsifying and imparting a soft and substantive touch in solution.
  • the second family is characterized by compounds having a low grafting rate with a high fatty ester / polyose ratio, included, for example, between 15 and 100% by weight, preferably between 40 and 90%. This family has very marked moisturizing properties.
  • the present invention further relates to the use of the polyose-fatty ester product as an emulsifying or co-emulsifying agent in the context of topical cosmetic or pharmaceutical applications.
  • any proportion of the above product may be used.
  • Particularly preferred proportions by weight for which an emulsifying or co-emulsifying effect is obtained vary between 0.1% and 10%. Preferred proportions are of the order of 1 to 3% by weight relative to the total weight of the composition to be emulsified.
  • the invention also relates to the use of the polyose-fatty ester product as a film-forming agent, in particular providing a soft touch in the context of cosmetic or pharmaceutical applications.
  • any proportion of the aforementioned complex product can be used.
  • Particularly preferred proportions by weight for which a film-forming and mild effect is obtained vary between 0.1% and 25%. Preferred proportions are of the order of 1 to 3% by weight relative to the total weight of the composition to be emulsified.
  • the invention also relates to the use of the product as a moisturizing agent in the context of cosmetic or pharmaceutical applications.
  • any proportion of the product of the invention can be used.
  • Particularly preferred proportions by weight for which a hydrating effect is obtained vary between 0.1% and 10%.
  • Preferred proportions are of the order of 1 to 3% by weight relative to the total weight of the composition.
  • the invention also relates to an emulsifying composition, characterized in that it contains as an emulsifying or coemulsifying agent a polyose-fatty ester complex product as defined above.
  • the invention also relates to a moisturizing composition, characterized in that it contains, as hydrating agent, a polyose-fatty ester product as defined above.
  • the present invention also relates to a film-forming composition, characterized in that it contains as a film-forming agent a polyose-fatty ester, as defined above.
  • the products of the invention can also be used in a totally different field, namely the recovery or the dispersion of hydrocarbons, as well on soils as on expanses of water.
  • the product of the invention will be used as a surfactant for emulsifying or dispersing the fat phases, at concentrations conventionally used for this purpose.
  • the polyoses from ulva 500 grams
  • sodium oleate (225 grams) and lithium oleate (53 grams) are mixed in a 4 liter reactor.
  • the mixture is heated at 150 ° C. for 6 h with mechanical stirring (600 rpm) and under reduced pressure.
  • the reaction medium is dissolved in butanone.
  • the soaps are neutralized with lactic acid.
  • Distilled water is added and a gelled phase is formed which is easily separated from the reaction medium.
  • This gelled phase is dried and constitutes the first family of polyose-esters.
  • the remainder of the reaction medium is washed several times with distilled water and then the washing water is extracted with butanol.
  • the butanol phase is dried and contains the second family of polyose-esters. This second family contains the most grafted polyoses. Distillation of the remaining organic phase allows the recovery of butanone, fatty acids and methyl esters for recycling.
  • the remainder of the reaction medium is washed several times with distilled water and then the washing water is extracted with butanol.
  • the butanol phase is dried and contains the second family of polyose-esters. This second family contains the most grafted polyoses. Distillation of the remaining organic phase allows the recovery of butanone, fatty acids and methyl esters for recycling.
  • Ulva polyoses 500 grams, methyl oleate (1200 grams), sodium oleate (225 grams) and lithium oleate (53 grams) were mixed in a 4 liter reactor. The mixture is heated at 150 ° C. for 6 h with mechanical stirring (600 rpm) and under reduced pressure. The reaction medium is dissolved in butanone. The soaps are neutralized with lactic acid. Distilled water is added and the gel-containing aqueous phase is separated off. This phase is dried and constitutes the complex family of polyose-esters. Distillation of the remaining organic phase allows the recovery of butanone, fatty acids and methyl esters for recycling. The polyose-esters have a fatty acid / polyose proportion which is close to 55% by weight.
  • Texapon NSO sodium laureth sulfate 20.0% by weight
  • Tegobetaine F 50 cocamidopropylbetaine
  • Polyose-ester complex derived from Example 4 1.5% by weight NaCl Amount sufficient for the desired viscosity Water; to complete at 100.0% weight
  • the shampoo is homogeneous, stable, soft to the touch after rinsing.
  • Texapon NSO sodium laureth sulfate 20.0%
  • Tegobetaine F 50 (cocamidopropylbetaine) 5%
  • the shower gel is homogeneous, stable, it leaves a soft and pleasant film on the skin after rinsing.
  • Polyose ester compound of Example 4 2.5% Polysorbate 80: 4%
  • the polyose-ester compound of Example 4 is therefore emulsifying. It brings in addition a soft and substantive touch.
  • the polyose-ester compound of Example 5 is therefore coemulsifier. It brings in addition a soft and substantive touch.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)
EP06820311A 2005-10-19 2006-10-18 Aus dem pfropfen von fettketten auf ulvane resultierendes produkt und verwendung des produkts als tensid Withdrawn EP1945677A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0510643A FR2892119B1 (fr) 2005-10-19 2005-10-19 Produit resultant du greffage de chaines grasses sur des ulvanes et son utilisation comme tensioactif
PCT/FR2006/051055 WO2007045795A1 (fr) 2005-10-19 2006-10-18 Produit resultant du greffage de chaines grasses sur des ulvanes et son utilisation comme tensioactif

Publications (1)

Publication Number Publication Date
EP1945677A1 true EP1945677A1 (de) 2008-07-23

Family

ID=36572233

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06820311A Withdrawn EP1945677A1 (de) 2005-10-19 2006-10-18 Aus dem pfropfen von fettketten auf ulvane resultierendes produkt und verwendung des produkts als tensid

Country Status (4)

Country Link
US (1) US20090299053A1 (de)
EP (1) EP1945677A1 (de)
FR (1) FR2892119B1 (de)
WO (1) WO2007045795A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2982152B1 (fr) * 2011-11-07 2014-02-07 Oreal Polysaccharides sulfates agent d'hydratation de la peau
ITUB20152059A1 (it) * 2015-07-10 2017-01-10 Enrico Giotti S P A Composto intorbidante e aromatizzante per bevande contenente ulvani
CN105399854B (zh) * 2015-12-17 2017-07-21 浙江工商大学 同时增强浒苔多糖抗氧化和抗菌活性的方法
CN105542022B (zh) * 2015-12-17 2017-12-08 浙江工商大学 提高浒苔多糖生物活性的方法
CN105733845B (zh) * 2016-03-28 2019-09-06 山东天竞电子科技有限公司 一种led电子显示屏幕清洗剂及制备方法和清洁方法
GB2624934B (en) 2022-12-01 2025-05-07 Kelp Ind Ltd Composite material
US20250368573A1 (en) 2023-05-25 2025-12-04 Blue Evolution Inc. Ecofriendly biopolymer admixture for cement and concrete applications
WO2025128797A1 (en) 2023-12-13 2025-06-19 Blue Evolution, Inc Ecofriendly, biodegradable biological polysaccharide composition for packaging materials

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2655268B1 (fr) * 1989-12-06 1994-10-14 Secma Utilisation d'extraits d'algues pour la preparation de compositions pharmaceutiques, cosmetiques, alimentaires ou a usage agricole.
FR2671725B1 (fr) * 1991-01-23 1995-06-02 Coletica Complexe de polyose et d'acide gras, utilisation comme agent emulsionnant ou hydratant et composition emulsionnante ou hydratante en contenant.
CA2210524A1 (en) * 1995-03-23 1996-09-26 Lancaster Group Gmbh Cosmetic with condensates of plant and animal decomposition products
FR2868252B1 (fr) * 2004-03-30 2006-07-21 Cie Financiere Et De Participa Utilisation des ulvanes comme eliciteurs des mecanismes d'absorption de l'azote et de la synthese proteique

Non-Patent Citations (1)

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Title
See references of WO2007045795A1 *

Also Published As

Publication number Publication date
WO2007045795A1 (fr) 2007-04-26
FR2892119A1 (fr) 2007-04-20
FR2892119B1 (fr) 2008-01-18
US20090299053A1 (en) 2009-12-03

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