EP0973496A1 - UTILISATION D'ESTERS OLIGOMERES, DE FAIBLE POIDS MOLECULAIRE, D'ACIDES $g(a)-HYDROXYLIQUES ET/OU D'ACIDES o-HYDROXYLIQUES AROMATIQUES DANS DES FORMULATIONS COSMETIQUES - Google Patents

UTILISATION D'ESTERS OLIGOMERES, DE FAIBLE POIDS MOLECULAIRE, D'ACIDES $g(a)-HYDROXYLIQUES ET/OU D'ACIDES o-HYDROXYLIQUES AROMATIQUES DANS DES FORMULATIONS COSMETIQUES

Info

Publication number
EP0973496A1
EP0973496A1 EP98921437A EP98921437A EP0973496A1 EP 0973496 A1 EP0973496 A1 EP 0973496A1 EP 98921437 A EP98921437 A EP 98921437A EP 98921437 A EP98921437 A EP 98921437A EP 0973496 A1 EP0973496 A1 EP 0973496A1
Authority
EP
European Patent Office
Prior art keywords
hydroxy acids
aromatic
acid
hydroxy
acids
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Withdrawn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
EP98921437A
Other languages
German (de)
English (en)
Inventor
Berthold Nies
Wolfgang Ritter
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP0973496A1 publication Critical patent/EP0973496A1/fr
Withdrawn legal-status Critical Current

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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—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
    • A61K8/37—Esters of carboxylic 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants

Definitions

  • the invention relates to the use of low molecular weight, oligomeric
  • Esters of ⁇ -hydroxy acids and / or aromatic o-hydroxy acids in cosmetic formulations are included.
  • AHA ⁇ -hydroxy acids
  • these acids are often referred to as fruit acids, a name that indicates their natural occurrence.
  • the most important fruit acids include, for example, glycolic acid (from sugar cane), lactic acid (from sour milk), citric acid (from citrus fruits), tartaric acid (from wine), malic acid (from apples) or pyruvic acid (from papaya fruits).
  • the aromatic o-hydroxy acids e.g. salicylic acid have the same effects.
  • Salicylic acid which has also long been used to treat acne, psoriasis, warts or dandruff, is of great importance as a keratolytic and keratoplastic substance in cosmetics, since its use causes a mild peeling of the skin.
  • a large number of cosmetic products are now flooding the market which contain such AHA or aromatic o-hydroxy acids and which are positioned as an anti-wrinkle cream or anti-aging product or as a product for regenerating the skin.
  • the incorporation of the free acid into the cosmetic carrier has further disadvantages.
  • the relatively low pH value can lead to considerable intolerance reactions; secondly, the readily water-soluble acids are washed out again shortly after application. Products that contain derivatives of these AHAs, which initially do not bring about a sharp drop in pH and from which the AHA would be released slowly over a longer period of time, would be desirable.
  • the invention therefore relates to the use of low molecular weight, oligomeric esters of ⁇ -hydroxy acids and / or aromatic o-hydroxy acids in cosmetic formulations, the corresponding ⁇ -hydroxy acid and / or aromatic o-hydroxy acid being released in a controlled manner by hydrolysis during use.
  • Such polymers or oligomers are known in principle.
  • high polymeric esters of selected lower hydroxy acids, possess and in particular of lactic acid, high body vertägzier be used in the surgical technique for example, as tolerated by the body and Consequentlyresorbierbares thread material degraded in the course of weeks or months and flushed out of the 'body becomes.
  • Oligomeric esters, in particular of lactic acid and / or of glycolic acid, which have an average degree of oligomation of up to 100 are known from DE 36 20 685. There the use of these esters as resorbable carriers and / or film formers in agents for covering human or animal skin is described.
  • the oligomers according to the invention are notable for an average degree of oligomerization of the chosen acid of up to about 30 and preferably up to about 10.
  • polyester oligomers from hydroxycarboxylic acids can be obtained directly by polycondensation of the hydroxycarboxylic acids or
  • “_ Organic acids can be considered.
  • the two esters forming groups of the monomers or the oligomers i.e. the hydroxyl group on the one hand and the carboxyl group on the other hand are generally suitable as reactive sites for this.
  • alcohols are preferred in preferred embodiments
  • glycerin which leads to extraordinarily varied products when reacted with the AHA oligomers.
  • suitable alcohols are: ethylene glycol, propylene glycol, 1, 3-butylene glycol, trimethyloipropane, low molecular weight polyethylene glycols, polypropylene glycol, 1, 5-pentanediol or higher alcohols.
  • carboxylic acids in particular monocarboxylic acids, can be of interest, but also polyfunctional carboxylic acids, for example di- or tricarboxylic acids.
  • the oligomeric hydroxycarboxylic acids or their derivatives are prepared in a manner known per se.
  • the esters of hydroxy acids are therefore suitable, for example, and the easily manageable dimerization products, e.g. lactic acid and / or glycolic acid, i.e. use the lactide and / or the glycolide.
  • the polycondensation reaction is usually carried out by heating the starting materials to a temperature above the melting point, preferably in the presence of a catalyst, in particular an esterification catalyst, under anhydrous conditions in an inert gas atmosphere.
  • a catalyst in particular an esterification catalyst
  • the amount and type of catalyst used determine the process temperature and the duration of the Implementation. Since the conversion of the reactions is normally almost 100%, the composition of the end products can be controlled well by adding the reactants.
  • Such polycondensation reactions are well known to those skilled in the art. A detailed list of the most diverse reaction conditions is therefore not necessary at this point.
  • the invention also relates to low molecular weight oligomers
  • ⁇ -hydroxy acids and / or aromatic o-hydroxy acids produced by reacting the monomeric ⁇ -hydroxy acids and / or aromatic o-hydroxy acids or their reactive derivatives with mono- or polyhydric alcohols or organic acids, for use in cosmetics Formulations, the corresponding ⁇ -hydroxy acid and / or aromatic o-hydroxy acid being released in a controlled manner by hydrolysis from these oligomers during use.
  • ⁇ -hydroxy acids and o-hydroxy acids used are preferably the compounds listed below: glycolic acid and lactic acid, both of which occur in the metabolism of the living organism and can be processed or excreted by the body, whereby
  • the lactic acid is used in the form of its racemate or in the form of its optical antipodes or as any mixtures of the optical antipodes; Hydroxylbutyric acid, hydroxyvaleriaric acid, citric acid, tartaric acid, malic acid, trimethylene carbonate, ⁇ -caprolactone, salicylic acid, m-hydroxybenzoic acid, p-hydroxybenzoic acid, gallic acid, or the like
  • Grape acid, benzilic acid, mandelic acid or pyruvic acid Grape acid, benzilic acid, mandelic acid or pyruvic acid.
  • 35 Glycolic acid and / or lactic acid or their dimerization products are very particularly preferably used.
  • homooligomers are used in important embodiments of this invention. This means that only a single ⁇ -hydroxy acid or one of its reactive derivatives or only a single o-hydroxy acid or one of its reactive derivatives, e.g. only lactic acid or only salicylic acid can be used to prepare the oligomeric esters.
  • heterooligomers are used. This means that two or more different ⁇ -hydroxy acids and / or aromatic o-hydroxy acids are used in the polycondensation reaction to produce the oligomeric products. Mixtures of ⁇ -hydroxy acids and e.g. Salicylic acid can be used as monomers.
  • Particularly preferred oligomers are synthesized, for example, from the following monomers: glycerol, lactide and glycolide; Ethylene glycol, lactic acid and glycolic acid; Propylene glycol, lactide and glycolide; Glycerin and lactide; Glycerin, glycolic acid and hydroxylbutyric acid; Ethylene glycol and hydroxyvaleric acid; Glycerin and lactic acid ethyl ester; Glycerin, trimethylene carbonate and glycolic acid; Ethylene glycol and lactide; Ethylene glycol, glycolic acid and lactic acid ethyl ester; Glycerin, glycolic acid and ⁇ -caprolactone.
  • the heterooligomers generally have advantageous properties because, for example, they have a lower tendency to crystallize and the associated clouding. Furthermore, they can be broken down more quickly through a higher water absorption and hydrolysis rate.
  • OU component containing conventional auxiliaries for cosmetic preparations. Both components are only mixed directly before use for the finished cosmetic preparation. This can preferably be done with known mixing systems from (medicine) technology, 35 such as systems for mixing bone cements, reactive adhesives or impression materials.
  • the double-chamber syringe known to the person skilled in the art with a static mixer attached can be mentioned as an example.
  • these mixing systems the mixing ratio of oligomer phase to aqueous phase can also be easily adjusted and varied. Mixing ratios of 1:10 to 1: 1 are possible, for example. Mixing systems from MIXPAC Systems AG are also suitable, for example.
  • the invention therefore also relates to a cosmetic preparation consisting of a ready-to-use set of two or more separate components, one component of which is a water-free formulation of oligomer products according to at least one of the
  • Claims 1 to 7 optionally with further auxiliaries, and as another component a water-containing cosmetic formulation, optionally with further auxiliaries and additives customary in such cosmetic preparations.
  • the advantage of using the described oligomeric products is that there is primarily no sharp drop in pH which could irritate the skin.
  • the monomeric AHA or the aromatic o-hydroxy acids are gradually released, and these can then trigger their known advantageous effects on the skin. Further, this can, of course, a larger amount of serving as a depot for the free acids oligomers are incorporated, 'so that the effect is considerably improved compared to use of the free AHA.
  • the components for the formulation of the corresponding cosmetic preparations can be selected from the large number of known and proven substances.
  • the oligomeric esters of the ⁇ -hydroxy acids and / or aromatic o-hydroxy acids can be mixed well with the customary skin-care components and auxiliaries, advantageously using a water-free preparation.
  • an anhydrous formulation of the oligomers is possibly prepared with suitable auxiliaries or additives and, on the other hand, a cosmetic preparation consisting of the usual skin-care components.
  • the oligomers can be contained in the oily phase, and the aqueous phase is formulated separately.
  • the second aqueous phase then contains the remaining components which are customary for a skin-care preparation. The two separate phases are then only mixed before each application.
  • the cosmetic preparations according to the invention can contain the oligomeric products in amounts of approximately 5 to almost 100%, the use of the pure oligomer substance also being possible.
  • the preferred content of oligomeric esters in the finished product is 5% to 50%.
  • ethylene glycol oligolactide of the composition 1: 1.5 (preparation analogous to Example 4) and glycerol oligolactide of the composition 1: 5 (preparation analogous to Example 1) are mixed homogeneously in a ratio of 40:60.
  • the mixture is filled into a 10 ml chamber of a 1: 1 double chamber syringe at this temperature. After cooling, this mixture has a honey-like consistency.
  • the aqueous phase contains:
  • phase II is adjusted to that of phase I at room temperature by adding polyacrylic acid sodium salt.
  • Phase II is then filled into the second chamber of the double-chamber syringe.
  • the double-chamber syringe is closed as usual.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation d'esters oligomères, de faible poids moléculaire, d'acides alpha -hydroxyliques et/ou d'acides o-hydroxyliques aromatiques dans des formulations cosmétiques, l'acide alpha -hydroxylique et/ou l'acide o-hydroxylique aromatique correspondants étant libérés de manière contrôlée par hydrolyse pendant l'utilisation.
EP98921437A 1997-04-10 1998-04-07 UTILISATION D'ESTERS OLIGOMERES, DE FAIBLE POIDS MOLECULAIRE, D'ACIDES $g(a)-HYDROXYLIQUES ET/OU D'ACIDES o-HYDROXYLIQUES AROMATIQUES DANS DES FORMULATIONS COSMETIQUES Withdrawn EP0973496A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19714765 1997-04-10
DE19714765A DE19714765A1 (de) 1997-04-10 1997-04-10 Verwendung von niedermolekularen, oligomeren Estern von alpha-Hydroxysäuren und/oder aromatischen o-Hydroxysäuren in kosmetischen Formulierungen
PCT/EP1998/002013 WO1998044903A1 (fr) 1997-04-10 1998-04-07 UTILISATION D'ESTERS OLIGOMERES, DE FAIBLE POIDS MOLECULAIRE, D'ACIDES α-HYDROXYLIQUES ET/OU D'ACIDES o-HYDROXYLIQUES AROMATIQUES DANS DES FORMULATIONS COSMETIQUES

Publications (1)

Publication Number Publication Date
EP0973496A1 true EP0973496A1 (fr) 2000-01-26

Family

ID=7825977

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98921437A Withdrawn EP0973496A1 (fr) 1997-04-10 1998-04-07 UTILISATION D'ESTERS OLIGOMERES, DE FAIBLE POIDS MOLECULAIRE, D'ACIDES $g(a)-HYDROXYLIQUES ET/OU D'ACIDES o-HYDROXYLIQUES AROMATIQUES DANS DES FORMULATIONS COSMETIQUES

Country Status (10)

Country Link
EP (1) EP0973496A1 (fr)
JP (1) JP2001521508A (fr)
KR (1) KR20000076112A (fr)
CN (1) CN1251034A (fr)
AU (1) AU7429598A (fr)
CA (1) CA2283517A1 (fr)
DE (1) DE19714765A1 (fr)
HU (1) HUP0001693A2 (fr)
PL (1) PL335423A1 (fr)
WO (1) WO1998044903A1 (fr)

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US7833543B2 (en) 1995-06-07 2010-11-16 Durect Corporation High viscosity liquid controlled delivery system and medical or surgical device
US6413536B1 (en) * 1995-06-07 2002-07-02 Southern Biosystems, Inc. High viscosity liquid controlled delivery system and medical or surgical device
US20040001889A1 (en) 2002-06-25 2004-01-01 Guohua Chen Short duration depot formulations
ATE482695T1 (de) 2002-12-13 2010-10-15 Durect Corp Orale darreichungsform mit flüssigen hochviskosen trägersystemen
BRPI0515372B8 (pt) 2004-09-17 2021-05-25 Durect Corp composição líquida para fornecer anestesia local prolongada após administração a um indivíduo, e, uso de bupivacaína, acetato isobutirato de sacarose e álcool benzílico
US20070027105A1 (en) 2005-07-26 2007-02-01 Alza Corporation Peroxide removal from drug delivery vehicle
CN105411870B (zh) * 2006-07-06 2018-12-25 斯蒂潘公司 乳酰乳酸烷基酯及其制备方法
EP2444060B1 (fr) 2006-07-06 2017-08-23 Stepan Company Composition de soin
WO2008006058A2 (fr) 2006-07-06 2008-01-10 Stepan Company Compositions de solvants d'alkyl lactyl lactate
PL2117521T3 (pl) 2006-11-03 2012-11-30 Durect Corp Transdermalne systemy dostarczania zawierające bupiwakainę
WO2009075782A1 (fr) 2007-12-06 2009-06-18 Durect Corporation Procédés utiles dans le traitement de la douleur, d'états rhumatismaux ou d'inflammations associées à un état chronique
US20100260844A1 (en) 2008-11-03 2010-10-14 Scicinski Jan J Oral pharmaceutical dosage forms
JP5219093B2 (ja) * 2009-11-14 2013-06-26 公益財団法人北九州産業学術推進機構 乳酸オリゴマーおよびその成形体
CA2905131A1 (fr) 2013-03-15 2014-09-18 Durect Corporation Compositions ayant un agent de modification rheologique pour reduire une variabilite de dissolution
JP2015093854A (ja) * 2013-11-12 2015-05-18 株式会社クレハ 水性組成物および加水分解抑制方法
US12274794B2 (en) 2016-07-06 2025-04-15 Orient Pharma Co., Ltd. Oral dosage form with drug composition, barrier layer and drug layer
CA3167217A1 (fr) 2020-01-13 2021-07-22 Durect Corporation Systemes d'administration de medicament a liberation prolongee avec impuretes reduites et procedes associes
CN116940358A (zh) 2021-01-12 2023-10-24 度勒科特公司 持续释放药物递送系统和有关的方法

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DE3620685A1 (de) * 1986-06-20 1987-12-23 Henkel Kgaa Neue mittel zur abdeckung unverletzter und/oder verletzter bereiche menschlicher oder tierischer haut
US5091171B2 (en) * 1986-12-23 1997-07-15 Tristrata Inc Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use
DE19520237A1 (de) * 1995-06-02 1996-12-05 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen, enthaltend Oligomere oder Polymere von alpha-Hydroxycarbonsäuren

Non-Patent Citations (1)

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Also Published As

Publication number Publication date
DE19714765A1 (de) 1998-10-15
JP2001521508A (ja) 2001-11-06
CA2283517A1 (fr) 1998-10-15
KR20000076112A (ko) 2000-12-26
WO1998044903A1 (fr) 1998-10-15
HUP0001693A2 (hu) 2000-09-28
AU7429598A (en) 1998-10-30
PL335423A1 (en) 2000-04-25
CN1251034A (zh) 2000-04-19

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