WO2025191402A1 - Ingrédients cosmétiques dérivés de cutine de tomate - Google Patents

Ingrédients cosmétiques dérivés de cutine de tomate

Info

Publication number
WO2025191402A1
WO2025191402A1 PCT/IB2025/052335 IB2025052335W WO2025191402A1 WO 2025191402 A1 WO2025191402 A1 WO 2025191402A1 IB 2025052335 W IB2025052335 W IB 2025052335W WO 2025191402 A1 WO2025191402 A1 WO 2025191402A1
Authority
WO
WIPO (PCT)
Prior art keywords
cosmetic
cutin
acid
cosmetic ingredient
ingredient according
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.)
Pending
Application number
PCT/IB2025/052335
Other languages
English (en)
Inventor
Claudio PIROVANO
Nella GALOTTO GALOTTO
Patrizia Valsesia
Sara BETTINELLI
Gabriele Anisia DEPTA
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.)
Intercos Italiana SpA
Intercos SpA
Original Assignee
Intercos Italiana SpA
Intercos SpA
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 Intercos Italiana SpA, Intercos SpA filed Critical Intercos Italiana SpA
Publication of WO2025191402A1 publication Critical patent/WO2025191402A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks

Definitions

  • the present invention relates to the use of waste materials deriving from tomato industrial processing, for the preparation of cosmetic ingredients (upcycling).
  • the present invention relates to the use of tomato peels (cutin) for obtaining polyesters having a high natural index (biopolyesters) usable as cosmetic ingredients in sundry cosmetic compositions.
  • the chemical component extracted through cutin depolymerization is mainly 10,16-dihydroxyhexadecanoic acid.
  • NOI is a value indicating the extent to which a cosmetic ingredient complies with the definition of natural ingredient, derived natural ingredient or mineral derived ingredient indicated in the ISO 16128-1 :2016 standard “Guidelines on technical definitions and criteria for natural and organic cosmetic ingredients and products — Part 1 : Definitions for ingredients” https://www.iso.org/standard/62503.html. NOI can take values >0.5 and ⁇ 1, wherein 1 is the maximum degree of natural origin, while the ingredients with a calculated value of ⁇ 0.5 have a NOI equal to 0.
  • the NOC of a product is the mass percentage, comprised between 0% and 100%, of all the natural ingredients, natural portions of ingredients and ingredients of natural origin in the product. It is calculated as the sum of the relative concentrations of the ingredients of a product, multiplied by their corresponding NOI.
  • Polyesters are polymers obtained from the condensation between polycarboxylic acids and polyols, and therefore containing the ester functional group along all the main carbon chain. According to the monomers used for the synthesis thereof, and to the orientation of polymeric chains, they can have different features that determine their application. Polyesters find applications in several fields, from textile to paper, to cleaning products, cosmetics: in fact, many ingredients commonly used in the cosmetic field fall in this chemical class and can be combined in order to obtain stable final products.
  • the reaction for the synthesis of polyesters is a polycondensation with formation of the ester group in chain between the carboxylic group of the acid and the hydroxyl group of the alcohol with formation of a water molecule; its mechanism can be resumed in the following general formula:
  • EP4116352A1 describes a multilayer article comprising a first layer, comprising or consisting of paper, plastic, bio-plastic, metals, metal alloys, wood, and a second layer, adjacent to the first layer, comprising a bio-resin according to the teaching of the application.
  • Such bio- resin comprises or consists of a cutin extract, a mixture of water and an organic solvent, an organic solvent chosen from the group consisting of butyl glycol, 1,3- propanediol, ethanolamine, diethylamine and ethanol. Still preferably, the organic solvent is butyl glycol or 1,3 -propanediol.
  • the technical problem according to the present invention is obtaining cosmetic polyesters with a high natural index, capable of advantageously replacing cosmetic ingredients of petrochemical origin.
  • the depolymerization product of the cutin extracted from tomato peels represents the characterizing component of the synthetized cosmetic ingredients.
  • the other components are monomers and oligomers of natural origin or derived from natural sources, in particular from vegetal sources.
  • the object is reached by preparing cosmetic ingredients (biopolyesters) starting from the following reagents: a. product of cutin depolymerization (for the sake of brevity indicated in the examples as depolymerized cutin), preferably extracted from peels that are wastes of tomato industrial processing; b. a short diol or polyol (C 2 -C 8 ); c. a long diol or polyol having a high molecular weight, i.e. higher than 500 Dalton, comprising at least 20 carbon atoms; d. a dicarboxylic acid C 4 -C 50 .
  • one or more volatile and/or non-volatile cosmetic emollient oil with high NOI is added where required, having the function of solvent for the synthesis or as diluent for the polymer, like e.g. Coco-Caprylate/Caprate, Caprylic/Capric Triglyceride, Tridecane and Undecane, Triheptanoin, Octyldodecanol.
  • biopolyesters according to the present invention are used as cosmetic ingredients having film-forming, emollient or texturizing/rheologic modifier function, according to the structure of the polymer. Such biopolyesters have a good compatibility with oils and commonly cosmetic used ingredients.
  • the biopolyesters according to the present invention are polyesters having a high NOI (Natural Origin Index according to ISO 16128).
  • the biopolyesters according to the present invention have a NOI of 1 and anyway not lower than 0,7 and a molecular weight higher than 5000 Dalton and anyway with residues not lower than 1000 Dalton.
  • the synthetized polyesters can be used to replace raw materials of fossil origin like hydrogenated polyisobutenes (e.g. Hydrogenated Polyisobutene and others), polyurethanes, esters of non-natural origin, styrene-butadiene rubber, having similar features and to give to the final cosmetic compositions a high natural index.
  • hydrogenated polyisobutenes e.g. Hydrogenated Polyisobutene and others
  • polyurethanes e.g. Hydrogenated Polyisobutene and others
  • esters of non-natural origin e.g. Polystyrene-butadiene rubber
  • the polyesters described in this invention can take a linear, branched or cross-linked structure according to the composition and to the internal ratio of the monomers and oligomers constituting the polymer.
  • the main component of tomato (Solanum lycopersicum L.) is cutin, a non-toxic and biodegradable biopolyester, made of esterified hydroxy acids having 16 and 18 carbon atoms. Cutin can undergo extraction processes which allow to obtain such monomers, the main one being 10,16- dihydroxyhexadecanoic acid. By exploiting the functional groups of such acid, polymers of high molecular weight can be synthetized through polycondensation reactions, that can be used in cosmetic compositions in order to replace raw materials of fossil origin.
  • the product of cutin depolymerization can be obtained through different extraction techniques starting from tomato peels, representing the main by-product of tomato processing for the production of tomato preserves.
  • composition I 10,16-dihydroxyhexadecanoic acid according to points a., b., c., d. are described in the paper A. Cifarelli, I.M. Cigognini, L. Bolzoni, A. Montanari Physical-Chemical Characteristics of Cutin Separated from Tomato Waste for the Preparation of Bio-lacquers Advances in Sciences and Engineering 2019; Vol 11 No 1 https://doi.org/10.32732/ase.2019.11.1.33.
  • composition I 10,16-dihydroxyhexadecanoic acid after extraction with an organic solvent according to point e., is described in the papers: Benitez et al. Valorization of Tomato Processing by Products: Fatty Acid Extraction and Production of Bio-Based Materials Materials 2018, 11(11), 2211; https://doi.org/10.3390/ma11112211 and Osman et al. Preparation, Isolation, and Characterization of Cutin Monomers and Oligomers from Tomato Peels J Agric Food Chem 1999 Feb;47(2):799-802, https://pubs.acs.org/doi/10.1021/jf980693r.
  • biopolyesters of high molecular weight can be synthetized through polycondensation reactions, that can be used in cosmetic compositions, replacing raw materials of fossil origin.
  • a product of tomato cutin depolymerization having a high content of 10,16-dihydroxyhexadecanoic acid is used, anyway not lower than 60%.
  • Such product of cutin depolymerization can be e.g. obtained through the techniques described in the above-mentioned Tomapaint patent applications.
  • the product of cutin depolymerization appears as a sticky mass that does not dry at room temperature and that takes the shape of its container.
  • the brownish colour is due to the presence of lycopene, the carotenoid responsible for the red colour of tomatoes.
  • the product of cutin depolymerization comprises mainly 10,16-dihydroxyhexadecanoic acid, while its other components are 4-hydroxycinnamic acid and its isomers, sebacic acid and 9,12-octadecadienoic acid, as shown in Table 1.
  • Table 1 main components of tomato cutin after depolymerization.
  • the second reagent in the synthesis of biopolyesters according to the present invention is a short diol or polyol, i.e. a diol or polyol having a carbon chain comprising 2 to 8 carbon atoms (C 2 -C 8 ).
  • the short diols of natural origin derive from glucose fermentation, as by-product of sugar from cane sugar.
  • they include pentylene glycol having commercial name Hydrolite 5 - Green (Symrise), caprylyl glycol with commercial name Hydrolite 8 - Green (Symrise), propanediol with commercial name Zemea Propanediol (DuPont Tate), hexanediol.
  • glycerol can be used, having instead three OH groups.
  • the naturally derived glycerol can be obtained from any oil extractable from plants; mainly from rapeseed, sunflower and palm.
  • Glycerol of vegetal origin can be obtained through different methods known in the oleochemical industry, often as a by-product in the production of substances like fat acids and biodiesel.
  • the third reagent in the synthesis of biopolyesters according to the present invention is a high molecular weight diol or polyol (long diol), having a molecular weight at least higher than 500 Dalton, having a carbon chain with a number of carbon atoms higher than 20.
  • Preferred diols comprise hydrogenated dilinoleyl alcohol, castor oil and hydrogenated castor oil, esters of polyglycerols with a number of carbon atoms higher than 20, and diol esters made of natural components or naturally derived comprising:
  • the fourth reagent in the synthesis of biopolymers according to the present invention is a dicarboxylic acid with a chain comprising 4-50 carbon atoms (C 4 -C 50 ).
  • Such acids particularly preferred ones are: succinic acid (C 4 ), azelaic acid (C 9 ), sebacic acid (C 10 ), dilinoleic acid (C 36 ) and the like.
  • dicarboxylic acids on the market for which the vegetal origin is guaranteed, are: azelaic acid with commercial name Matrilox CA001M (Matrica), derived from the transformation of vegetal oils like high oleic sunflower oil grown in Italy and Europe; succinic acid with commercial name Biosuccinum (Roquette), derived from a “carbon negative” method of biomass fermentation; and dilinoleic acid with commercial name Pripol 1009 (Cargill), derived from linseed oil.
  • the high molecular diol or polyol (higher than 500 Dalton) is added in order to obtain a softer structure of the polymer, and have a final product suitable for cosmetic products.
  • the short diol or polyol is introduced in order to solubilize and soften cutin, so as to get a homogeneous reaction mixture and solubilize all the reagents.
  • the optimal percentage of the product of cutin depolymerization in the biopolyesters ranges between 5% and 40%, preferably 8% and 15%.
  • a naturally derived bifunctional carboxylic acid was chosen in order to promote the polycondensation reaction with the diols in the reaction.
  • the concentration of the product of cutin depolymerization was optimized in order to prevent that 10,16-dihydroxyhexadecanoic acid reacts with other molecules of 10,16-dihydroxyhexadecanoic acid leading to the previously described solid structures.
  • the short diols or polyols capable of solubilizing cutin are compounds having maximum 8 atoms of carbon and glycerol, with which the product of cutin depolymerization can be mixed in any ratio.
  • a further step was then added to the synthesis method, preceding the addition of the other reagents, wherein the product of cutin depolymerization is pre-dispersed, preferably in pentylene glycol or glycerol.
  • Said pentylene glycol is provided with two OH groups (glycerol with three), and can take part in the esterification reaction. This last precaution lead to a transparent and homogeneous product.
  • the reaction mixture undergoes the homogenization of the product of cutin depolymerization with the short diol or polyol in order to make the system fluid and workable as much as possible, then the other reagents are added, like long diol or polyol, dicarboxylic acid and optionally an emollient cosmetic oil, having the function of solvent.
  • the stoichiometric ratio typically used for the synthesis of polyesters is equimolar, preferably with an excess of overall OH groups, so that the polymer ends with hydroxy groups and is provided with a relatively low residual acidity.
  • a catalyst is added, (e.g. tin oxalate or tin octanoate) between 0.001% and 1% in weight, preferably between 0.05% and 0.5%.
  • the reaction occurs at 120° C - 200°C, for a time of 5-12 hours, under dynamic vacuum.
  • the cosmetic oil with solvent function is added at the beginning of the reaction when the oil is non-volatile, or at the end of the reaction when the oil is volatile.
  • the reaction is monitored through the measurement of residual acid functionalities, generally under 20 mg KOH/g in the final product (preferably 5 - 10 mg KOH/g), using infrared spectroscopy to verify the appearance of the peak characteristic for the ester (the peak shifts from 1700cm' 1 , typical for the dicarboxylic acid COOH to 1740cm' 1 , typical for the newly-formed ester COOR).
  • a checking of molecular weight of the final product is performed, that must be higher than 5000 Dalton (preferably around 20.000 Dalton); the presence of residues between 1000 Dalton and 5000 Dalton must be limited for the sake of cosmetic safety.
  • Example - polymer 1 [0051]
  • the diol ester used in this example contains glycerol, succinic acid, a mixture of carboxylic acid with C8-C10 chain.
  • Example - polymer 2
  • Example - polymer 2B
  • Example - polymer 3
  • the final product is characterized by high naturality, the combined use of raw materials derived from upcy cling, and cosmetic performances comparable to, or even better than, those obtained with the use of traditional raw materials.
  • Lip fluid can contain polymers according to the examples 1, 1B, 1C, 1D.
  • Example 2 Eyeshadow composition
  • the presence of the raw material object of the present application gives the final product, an eyeshadow, a better adhesion to skin and longer wear.
  • Example 2 Eyeshadow can contain polymers according to the examples 1, 1B, 1C, 1D.
  • Example 3 Liquid eyeshadow composition
  • compositions of the Example 3 Liquid eyeshadow can contain polymers according to the examples 1, 1B, 1C, 1D.
  • Example 4 Stylo composition
  • the presence of the raw material object of the present application gives the final product gloss and long-lasting properties.
  • composition of the Example 4 can contain polymers according to examples 1, 1B, 1C, 1D.
  • Example 5 Lipstick composition
  • the raw material gives the final product gloss and viscosity.
  • Lipstick can contain polymers according to the Examples 2, 2B, 2C.
  • composition of the Example 6 Lipstick can contain polymers according to the Examples 3, 3B.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un ingrédient cosmétique comprenant les composants suivants : a. le produit de dépolymérisation de cutine, obtenu à partir d'un traitement industriel de tomate, en particulier de pelures de tomate ; b. un diol ou polyol court ayant 2 à 8 atomes de carbone ; c. un diol ou polyol long présentant un poids moléculaire élevé, supérieur à 500 Dalton et un nombre d'atomes de carbone supérieur à 20 ; d. un acide dicarboxylique ayant 4 à 50 atomes de carbone. Facultativement, ledit ingrédient comprend en outre une huile cosmétique volatile et/ou non volatile. L'ingrédient cosmétique a la fonction de formation de film, d'émollient ou de texturisation/modificateur rhéologique. La présente description divulgue également le procédé de synthèse dudit ingrédient cosmétique et des produits cosmétiques finaux contenant lesdits ingrédients cosmétiques.
PCT/IB2025/052335 2024-03-15 2025-03-04 Ingrédients cosmétiques dérivés de cutine de tomate Pending WO2025191402A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102024000005818 2024-03-15
IT202400005818 2024-03-15

Publications (1)

Publication Number Publication Date
WO2025191402A1 true WO2025191402A1 (fr) 2025-09-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2025/052335 Pending WO2025191402A1 (fr) 2024-03-15 2025-03-04 Ingrédients cosmétiques dérivés de cutine de tomate

Country Status (1)

Country Link
WO (1) WO2025191402A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015028299A1 (fr) * 2013-08-26 2015-03-05 CHIESA, Virginio Procédé d'extraction d'un polymère de polyester ou de cutine à partir d'épluchures de tomates et polymère de polyester ainsi extrait
US20220251289A1 (en) * 2019-06-25 2022-08-11 Institut National De Recherche Pour L'agriculture, L'alimentation Et L'environney Method for preparing an elastomer from a hydroxylated fatty acid and elastomer obtained by such a method
EP4116352A1 (fr) * 2021-07-07 2023-01-11 Tomapaint S.r.l. Procédé d'extraction de cutin à partir de déchets de transformation de tomates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015028299A1 (fr) * 2013-08-26 2015-03-05 CHIESA, Virginio Procédé d'extraction d'un polymère de polyester ou de cutine à partir d'épluchures de tomates et polymère de polyester ainsi extrait
US20220251289A1 (en) * 2019-06-25 2022-08-11 Institut National De Recherche Pour L'agriculture, L'alimentation Et L'environney Method for preparing an elastomer from a hydroxylated fatty acid and elastomer obtained by such a method
EP4116352A1 (fr) * 2021-07-07 2023-01-11 Tomapaint S.r.l. Procédé d'extraction de cutin à partir de déchets de transformation de tomates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CIFARELLI A. ET AL: "Physical-Chemical Characteristics of Cutin Separated from Tomato Waste for the Preparation of Bio-lacquers", vol. 11, no. 1, 15 June 2019 (2019-06-15), pages 33 - 45, XP093203058, ISSN: 2046-0392, Retrieved from the Internet <URL:http://www.xpublication.com/index.php/ase/article/download/276/180> DOI: 10.32732/ase.2019.11.1.33 *

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