EP2176349A2 - Esters d'acide phosphorique contenant des atomes de phosphore pontés par l'intermédiaire de motifs diol - Google Patents

Esters d'acide phosphorique contenant des atomes de phosphore pontés par l'intermédiaire de motifs diol

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Publication number
EP2176349A2
EP2176349A2 EP08785166A EP08785166A EP2176349A2 EP 2176349 A2 EP2176349 A2 EP 2176349A2 EP 08785166 A EP08785166 A EP 08785166A EP 08785166 A EP08785166 A EP 08785166A EP 2176349 A2 EP2176349 A2 EP 2176349A2
Authority
EP
European Patent Office
Prior art keywords
phosphoric acid
formula
peg
structural units
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Withdrawn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
EP08785166A
Other languages
German (de)
English (en)
Inventor
Peter Klug
Franz-Xaver Scherl
Waltraud Simsch
Adelgunde Oberhauser
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.)
Clariant Finance BVI Ltd
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Clariant Finance BVI Ltd
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
Priority claimed from DE200710036183 external-priority patent/DE102007036183A1/de
Priority claimed from DE200810006855 external-priority patent/DE102008006855A1/de
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2176349A2 publication Critical patent/EP2176349A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/327—Polymers modified by chemical after-treatment with inorganic compounds containing phosphorus
    • 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
    • A61K8/86—Polyethers
    • 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
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
    • C08G65/3312—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group acyclic
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Definitions

  • the invention relates to esters of phosphoric acid or phosphoric acid derivatives, fatty alcohol which is optionally alkoxylated, and diol, and to their use as associative thickeners, in particular in cosmetic, pharmaceutical or dermatological compositions.
  • Water or solvent-containing multicomponent systems such as emulsions or suspensions are often adjusted or thickened to higher viscosities for economic reasons, for performance reasons or for reasons of stability.
  • the high viscosity of such preparations also offers further advantages in the production, packaging, filling and storage as well as during transport.
  • polyvinyl alcohols polyacrylamides, polyacrylic acid and various salts of polyacrylic acid, polyvinylpyrrolidone, polyvinyl methyl ether, polyethylene oxides, copolymers of maleic anhydride and vinyl methyl ether, as well as various mixtures and copolymers of the abovementioned compounds.
  • Fatty acid polyethylene glycol esters tend to hydrolyze in the presence of water, the resulting insoluble fatty acids cause undesirable turbidity.
  • Thickening agents of natural origin eg agar-agar or tragacanth
  • Class of compounds is affected by their high melting points or pour points.
  • EP 1 518 900 and EP 1 344 518 disclose cosmetic and pharmaceutical preparations containing oxalkylated polyglycerol esters as thickeners
  • Dispersants for aqueous, aqueous-alcoholic and aqueous-surfactant preparations and as emulsifiers, suspending agents with thickening effect and consistency regulator for emulsions and suspensions On the one hand, the associative thickeners described in the cited documents still have room for improvement in terms of their thickening performance, especially in purely aqueous systems, where they form only turbid gels, but also in terms of their stability at low pH. At pH values below 5, their gels and thickened surfactant solutions are not storage-stable, but lose their viscosity very quickly.
  • the object of the invention was therefore to provide a novel class of substances which is suitable for use in cosmetic products, gives a clear appearance in the formulations and also in a strongly acidic medium causes a high thickening capacity under temperature load and long storage times and this Properties combined with excellent thickening performance.
  • esters of phosphoric acid or esters of phosphoric acid derivatives with optionally alkoxylated fatty alcohols which are characterized in that the phosphorus atoms are bridged via groups derived from diols.
  • the present invention therefore provides phosphoric acid esters containing
  • Component b wherein the substances of component b) are selected from one or more compounds of the formula (I) R 2 -O- (CH 2 CH 2 O) u (C 3 H 8 O) v (DO) w -H (I)
  • R 2 is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms,
  • D is a linear or branched saturated alkylene group having 4 to 20 carbon atoms, a linear or branched mono- or polyunsaturated alkenylene group having 4 to 20 carbon atoms or -CH (aryl) CH 2 -, preferably -CH (phenyl) CH 2 - , stands,
  • u is a number from 0 to 200, preferably from 2 to 150, particularly preferably from 5 to 100, particularly preferably from 10 to 50,
  • v is a number from 0 to 100, preferably from 0 to 50, particularly preferably from 0 to 20,
  • w is a number from 0 to 100, preferably from 0 to 20, particularly preferably from 0 to 10, and
  • D has the meaning as in formula (I), a is a number from 0 to 800, preferably from 0 to 250, particularly preferably from 10 to 200 and particularly preferably from 20 to 100, b is a number from 0 to 100 , preferably from 0 to 50, c is a number from 0 to 100, preferably from 0 to 20,
  • the phosphoric acid esters of the invention contain at least 2 phosphorus atoms and can have a linear or branched structure from 4 P atoms.
  • R 2 , D, u, v and w have the meanings given above under formula (I).
  • the phosphoric esters according to the invention each contain at least one structural unit derived from substances of component a), at least one structural unit according to formula (I 1 ) and at least one structural unit according to formula (II 1 ).
  • the phosphoric esters of the invention contain no oxygen-oxygen bond -O-O-.
  • the structural units derived from the substances of components a), b) and c) are bound to each other via only one oxygen atom -O-.
  • Substances of components b) and c) is bound to a structural unit derived from the substances of component a) and wherein the structural unit derived from the substances of component a) has the structure
  • the number of structural units derived from substances of component b) per molecule of phosphoric acid ester is 2 or more and preferably 3 or more.
  • R 2 is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms.
  • At least 80%, preferably from 90 to 100%, particularly preferably from 95 to 100% of the theoretically maximum obtainable esterifiable functions in the phosphoric esters from the substances of component a) are esterified.
  • the remaining free valencies on the phosphorus atom, ie the non-esterified of the esterifiable functions, may be acid groups P-OH, but also groups of the form P-O counterion, the counterions being selected from Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + and quaternary ammonium ions [HNR 1 R 2 R 3 J + , wherein R 1 , R 2 and R 3 are independently hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear mono-hydroxyalkyl group having 2 to 10 carbon atoms, preferably a mono-hydroxyethyl or mono-hydroxypropyl group, and a linear or branched di-hydroxyalkyl group having 3 to 10 carbon atoms , could be.
  • the degree of neutralization of the non-esterified phosphorus valencies (P-OH) in the phosphoric acid esters according to the invention can be between 0 and 100%. In a preferred embodiment of the invention, the degree of neutralization is from 0 to 20%. In another preferred embodiment of the invention, the degree of neutralization is from 20.1 to 100%.
  • v and w in the structural units derived from the compounds of the formula (I) are 0.
  • u in the structural units derived from the compounds of the formula (I) is from 1 to 150, preferably from 5 to 100 and particularly preferably from 10 to 50.
  • a in the structural units derived from the compounds of the formula (II) is from 1 to 800, preferably from 10 to 200 and particularly preferably from 20 to 100.
  • the one or more structural units are derived from the one or more diols of formula (II) derived from diols selected from ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol (PEG) having molecular weights from 200 to 35,000 , preferably PEG 200, PEG 300, PEG 400, PEG 600, PEG 800, PEG 1000, PEG 1500, PEG 2000, PEG 3000, PEG 3350, PEG 4000, PEG 6000, PEG 8000, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, polybutylene glycol , Copolymers of ethylene oxide and propylene oxide having molecular weights of 200 to 35,000, 1, 2-butanediol, 1, 3-butanediol, 1, 4-butanediol, 1, 2-pentanediol, 1, 3-pentanediol,
  • the one or more structural units derived from the one or more compounds of the formula (I) are structural units in which u is from 1 to 200, preferably from 2 to 150, more preferably from 5 to 100, particularly preferably from 10 to 50, v and w are 0, and the radical R 2 -O- is derived from alcohols selected from octanol, decanol, dodecanol, Tetradecanol, hexadecanol, octadecanol, eicosanol, behenyl alcohol, fatty alcohols having C-chain cuts 8-22, preferably Cio / Ci2 fatty alcohol, C ⁇ / Cu-fatty alcohol, C 2 / C 5 fatty alcohol and Ci ⁇ / C i ⁇ -fatty alcohol, branched fatty alcohols, preferably Guerbet alcohols and monounsaturated fatty alcohols, preferably delta-9-cis-hexadecanol, delta-9-cis-o
  • the one or more structural units derived from the one or more compounds of the formula (I) are derived from structural units
  • C 6/18 fatty alcohol ethoxylates with 10-50 ethylene oxide units preferably structural units derived from substances selected from C 06/18 fatty alcohol ethoxylate with 11 ethylene oxide units, C 16/18 fatty alcohol ethoxylate with 25 ethylene oxide units and Ci 6/1 8- fatty alcohol ethoxylate with 50 ethylene oxide units.
  • the total number of structural units contained in the phosphoric acid esters is derived from the one or more compounds of the formula (I), preferably the total number of those contained in the phosphoric acid esters
  • the total number of ethylene oxide units contained in the phosphoric acid units in the structural units derived from the substances of component b) and the substances of component c) together per fatty alcohol end group derived from the compounds of formula (I) from 30 to 100 , preferably from 40 to 80.
  • Further preferred phosphoric acid esters according to the invention are characterized in that the structural units derived from the substances of component a) are selected from structural units of the formulas (A1) to (A3)
  • Each M is independently H + or a counterion and the
  • Counterions are selected from Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + and quaternary ammonium ions [HNR 1 R 2 R 3 J + , where R 1 , R 2 and R 3 are each independently hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear mono-hydroxyalkyl group having 2 to 10 carbon atoms, preferably a mono-hydroxyethyl or Mono-hydroxypropyl group, as well as a linear or branched di-hydroxyalkyl group having 3 to 10 carbon atoms, and are preferably structural units of the formula (A1).
  • the phosphoric esters consist of structural units derived from the substances of components a), b) and c).
  • the phosphoric acid esters according to the invention are selected from compounds of the formula (III)
  • V is a group of formula (MIb)
  • M is a group of formula (IMc)
  • R a are each independently of one another -OH, -OS or radicals of the formula (I 1 )
  • R 2 is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms,
  • D is a linear or branched saturated alkylene group having 4 to 20 carbon atoms, a linear or branched mono- or polyunsaturated alkenylene group having 4 to 20 carbon atoms or -CH (ArVl) CH 2 -, preferably -CH (phenyl) CH 2 - , stands, u is a number from 0 to 200, preferably from 2 to 150, particularly preferably from 5 to 100, particularly preferably from 10 to 50,
  • v is a number from 0 to 100, preferably from 0 to 50, particularly preferably from 0 to 20,
  • w is a number from 0 to 100, preferably from 0 to 20, particularly preferably from 0 to 10, and
  • radicals of the formula (I 1 ) can be arranged block-wise or randomly distributed, Q in each case independently of one another radicals of the formula (II 1 )
  • a is a number from 0 to 800, preferably from 0 to 250, particularly preferably from 10 to 200 and particularly preferably from 20 to 100,
  • b is a number from 0 to 100, preferably from 0 to 50,
  • c is a number from 0 to 100, preferably from 0 to 20, and
  • x is a number from 0 to 10, preferably 0 to 5, particularly preferably 0 to 3
  • y is a number from 0 to 10, preferably 0 to 5, particularly preferably 0 to 3
  • Phosphoric acid esters of the formula (III) is greater than or equal to 1, preferably greater than or equal to 2 and particularly preferably greater than or equal to 3.
  • the formula E 2 V 0 M 0 can also be represented by the following structural formula of two structural units of the formula (IIIa)
  • R 2 in the radicals of the formula (I ' ) is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms.
  • phosphoric acid esters of the formula (III) are those in which at least 80%, preferably from 90 to 100%, particularly preferably from 95 to 100%, which are esterified directly to the phosphorus atoms P bound esterified functions.
  • the degree of neutralization of the non-esterified phosphorus valences in the phosphoric acid esters of the formula (III) may be between 0 and 100%. In a preferred embodiment of the invention, the degree of neutralization is from 0 to 20%. In another preferred embodiment of the invention, the degree of neutralization is from 20.1 to 100%.
  • Preferred counterions S in the phosphoric acid esters of the formula (III) are selected from Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + and quaternary ammonium ions [HNR 1 R 2 R 3 J + , wherein R 1 , R 2 and R 3 are independently hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear mono-hydroxyalkyl group having 2 to 10 carbon atoms, preferably a mono-hydroxyethyl or mono-hydroxypropyl group, as well as a linear or branched di-hydroxyalkyl group having 3 to 10 carbon atoms, may be.
  • phosphoric acid esters of the formula (III) are those in which v and w in the radicals of the formula (I 1 ) are 0.
  • phosphoric acid esters of the formula (III) are those in which u in the radicals of the formula (I 1 ) is from 1 to 150, preferably from 5 to 100 and particularly preferably from 10 to 50.
  • phosphoric acid esters of the formula (III) are those in which b and c in the radicals of the formula (II 1 ) are 0.
  • Further preferred phosphoric acid esters of the formula (III) are those in which a in the radicals of the formula (M 1 ) is from 1 to 800, preferably from 10 to 200 and particularly preferably from 20 to 100.
  • Further preferred phosphoric acid esters of the formula (III) are those in which the one or more radicals of the formula (II 1 ) are derived from diols selected from ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol (PEG) with molecular weights from 200 to 35,000 PEG 200, PEG 300, PEG 400, PEG 600, PEG 800, PEG 1000, PEG 1500, PEG 2000, PEG 3000, PEG 3350, PEG 4000, PEG 6000, PEG 8000, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, polybutylene glycol, copolymers from ethylene oxide and propylene oxide having molecular weights of 200 to 3
  • phosphoric acid esters of the formula (III) are those in which u in the radicals of the formula (I 1 ) is from 1 to 200, preferably from 2 to 150, more preferably from 5 to 100 and particularly preferably from 10 to 50, v and w in the radicals of the formula (I 1 ) are 0 and the groups R 2 -O- in the radicals of the formula (I 1 ) are derived from alcohols selected from octanol, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol, eicosanol, behenyl alcohol , Fatty alcohols with C-chain cuts between 8 and 22, preferably
  • Particularly preferred organophosphate of formula (III) according to the invention are those wherein the radicals of the formula (I 1) are derived from C 16/18 fatty alcohol ethoxylates having 10-50 ethylene oxide units, preferably of substances selected from Ci 6 / i 8 - Fatty alcohol ethoxylate with 11 ethylene oxide units, Ci 6/18 fatty alcohol ethoxylate with 25 ethylene oxide units and Ci 6/18 fatty alcohol ethoxylate with 50 ethylene oxide units.
  • phosphoric acid esters of the formula (III) are those in which the total number of radicals of the formula (I 1 ) contained therein, preferably the total number of radicals of the formula (I 1 ) contained therein.
  • u is from 1 to 200, preferably from 2 to 150, more preferably from 5 to 100 and particularly preferably from 10 to 50 and v and w are 0, from 4 to 20, preferably from 4 to 10, particularly preferably from 4 to 6, is.
  • phosphoric acid esters of the formula (III) are those in which the total number of ethylene oxide units present in the structural units of the formulas (I 1 ) and (II 1 ) together per radical of the formula (I 1 ) is from 30 to 100, preferably from 40 to 80 , is.
  • the present invention also provides mixtures comprising one or more phosphoric acid esters according to the invention.
  • these mixtures may also be phosphoric acid esters having only one phosphoric acid atom per molecule, in particular those of the formula
  • R 2 , u, v, w and D have the meanings mentioned above among the compounds of the formula (I).
  • these mixtures in turn, those are preferred which consist of said phosphoric acid esters.
  • the proportion of the inventive phosphoric acid esters in the mixtures according to the invention is preferably greater than 50% by weight, more preferably from 70 to 100% by weight and particularly preferably from 80 to 100% by weight.
  • the mixtures according to the invention consist of the phosphoric acid esters according to the invention.
  • the preparation of the phosphoric esters according to the invention is carried out by reacting phosphoric acid or derivatives thereof with alcohol, preferably fatty alcohol ethoxylate, and diol at temperatures of 150 to 250 0 C, preferably from 180 to 240 0 C and particularly preferably from 200 to 230 0 C.
  • Suitable phosphoric acid derivatives are polyphosphoric acid, tetraphosphorodecoxide, phosphorus oxychloride and phosphorus pentachloride.
  • Preferred reactant is orthophosphoric acid.
  • the esterification is preferably carried out to the extent that substantially neutral phosphoric acid esters according to the invention are present.
  • Preferred is a degree of conversion> 80%, d. H. More than 80% of all esterifiable functions of phosphoric acid or phosphoric acid derivatives are esterified.
  • Particularly preferred is a degree of conversion> 90%, particularly preferably> 95%.
  • the remaining free valences on the phosphorus atom may be acid groups, but also counterions selected from Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + , quaternary ammonium ions [HNR 1 R 2 R 3 J + , wherein R 1 , R 2 and R 3 are independently hydrogen, a linear or branched alkyl group with 1 to
  • the degree of neutralization of the unsubstituted phosphorus valencies (P-OH) can be between 0 and 100%.
  • Particularly preferred organophosphate according to the invention are obtainable from the reaction of a) 3-10 moles, preferably 4-8 moles, of a C 2 -C 22 -Fettalkoholethoxylats, preferably a fatty alcohol ethoxylate-Ciem, with 10-50 ethylene oxide units, b) 2 moles of Polyethylene glycol having an average molecular weight of 1500-8000, and c) 2-5 mol, preferably 2.5-4 mol, orthophosphoric acid.
  • Particularly preferred phosphoric acid esters according to the invention are obtainable from the reaction of a) 5 moles of a C 12-18 fatty alcohol ethoxylate, preferably a C 16/18 fatty alcohol ethoxylate, with 10 to 50 ethylene oxide units, preferably 25 ethylene oxide units, b) 2 moles of polyethylene glycol having an average molecular weight of 1500-8000, preferably having an average molecular weight of 4000 and c) 3 moles of orthophosphoric acid.
  • Extremely preferred phosphoric acid esters of the invention are obtainable from the reaction of a) 5 moles of a Ci 6 / i ⁇ fatty alcohol ethoxylate with 25 ethylene oxide units, b) 2 moles of polyethylene glycol having an average molecular weight of 4000 and c) 3 moles of orthophosphoric acid.
  • the phosphoric acid esters according to the invention have excellent thickening power, both for aqueous or aqueous-alcoholic compositions and for aqueous-surfactant compositions, and also tolerate organic solvents such as alcohols.
  • the phosphoric acid esters according to the invention are also advantageously suitable as thickener, consistency regulator, emulsifier, sensor additive, solubilizer, dispersant, lubricant, adhesive and stabilizer.
  • Another object of the invention therefore relates to the use of one or more of the phosphoric acid esters according to the invention as thickener, bodying agent, emulsifier, sensor additive, solubilizer, dispersant, lubricant, adhesive and stabilizer.
  • the phosphoric acid esters according to the invention are also advantageously suitable for the preparation of cosmetic, pharmaceutical and dermatological compositions.
  • the phosphoric acid esters according to the invention are also advantageously suitable for thickening cosmetic, pharmaceutical and dermatological compositions containing one or more surfactants. These are preferably shampoos.
  • Another object of the invention is therefore also the use of one or more inventive phosphoric acid esters for thickening of cosmetic, pharmaceutical and dermatological compositions containing one or more surfactants, preferably of shampoos.
  • the phosphoric acid esters of this invention after application of the formulations on the skin, reduce the formation of white residues on the subsequently dressed clothing.
  • Another object of the present invention is therefore also the use of one or more inventive phosphoric acid esters in deodorant or antiperspirant formulations, especially in deodorant or antiperspirant formulations containing aluminum salts, preferably aluminum chlorohydrate or aluminum-zirconium complex salts, to reduce the formation of white residues clothing after application of the deodorant or antiperspirant formulations on the skin.
  • inventive phosphoric acid esters in deodorant or antiperspirant formulations, especially in deodorant or antiperspirant formulations containing aluminum salts, preferably aluminum chlorohydrate or aluminum-zirconium complex salts, to reduce the formation of white residues clothing after application of the deodorant or antiperspirant formulations on the skin.
  • Another object of the invention are cosmetic, pharmaceutical and dermatological compositions containing one or more of the phosphoric acid esters of the invention.
  • the phosphoric acid esters according to the invention have a wide range of uses and are suitable for use in aqueous, aqueous-alcoholic and aqueous-surfactant compositions, emulsions, suspensions, dispersions, powders and sprays.
  • Preferred compositions according to the invention are in the form of aqueous, aqueous-alcoholic or aqueous-surfactant compositions, emulsions, suspensions, dispersions, powders or sprays.
  • the phosphoric acid esters according to the invention can be used as thickeners for aqueous or aqueous-alcoholic compositions, for example hair gels, moisturizing gels, antiperspirant gels, bleaching gels, conditioners and disinfecting gels. Furthermore, the phosphoric acid esters according to the invention are suitable as stabilizer, dispersant and bodying agent for aqueous-surfactant preparations, for example shampoos, shower baths, shower gels and bubble baths and for improving skin mildness and skin compatibility.
  • the thickening effect of the inventive phosphoric acid esters in aqueous surfactant compositions is brought about by the association of the hydrophobic end groups with the surfactant micelles and can be controlled by the choice of the ethoxylate end groups of the phosphoric esters according to the invention and by the choice of surfactants.
  • the suspending or stabilizing effect of the phosphoric acid esters according to the invention in aqueous-surfactant compositions is determined by the association of the hydrophobic end groups and the liquid components insoluble in aqueous-surfactant agents, for example oils and silicone oils, or the insoluble solid components, for example pigments and active ingredients such as Zinc pyrethiones, conditional.
  • the phosphoric acid esters according to the invention are also suitable as thickeners and dispersants, as emulsifiers, suspending agents with thickening effect and bodying agents for emulsions and suspensions, such as conditioners, as well as lubricants, adhesives, thickeners, dispersants and emulsifiers of decorative, solids-containing preparations. It is also possible to use mixtures of the phosphoric acid esters according to the invention.
  • the emulsifying, Stabilizing and / or consistency-giving effect of the phosphoric acid esters according to the invention in emulsions is caused or intensified by an association of the hydrophobic end groups with one another, as well as by an interaction of the hydrophobic end groups with the hydrophobic oil components.
  • the cosmetic, pharmaceutical or dermatological compositions according to the invention are present as emulsions.
  • the emulsions can be both water-in-oil emulsions and oil-in-water emulsions, microemulsions and multiple emulsions.
  • the preparation of the emulsions can be carried out in known manner, i. H. for example, by hot, hot / cold or PIT emulsification.
  • the non-aqueous fraction of the emulsions which is largely composed of the emulsifier, the thickener and the oil body, is usually from 5 to 95% by weight, preferably from 15 to 75% by weight. It follows that the emulsions may contain 5 to 95% by weight, preferably 25 to 85% by weight of water, depending on whether comparatively low lotions or high viscosity creams and ointments are to be produced.
  • the phosphoric esters according to the invention are used in rinse-off products, preferably shampoos, shower baths, shower gels and foam baths.
  • the phosphoric acid esters according to the invention in leave-on products, preferably skin care agents such as day creams, night creams, moisturizing lotions and gels, aqueous gels, such as.
  • skin care agents such as day creams, night creams, moisturizing lotions and gels, aqueous gels, such as.
  • skin care creams preferably nutritional creams, body lotions, ointments, sunscreens, lip balms, antiperspirants and deodorants used.
  • they are also suitable for surfactant-free, aqueous compositions and emulsions and for hair treatments, hair conditioners and hair gels, but also for perming agents, hair dyes, as well as for decorative cosmetics, such as make-ups, eye-shadows, lipsticks, mascara and the like.
  • the thickening power is also pronounced in strongly acidic medium and in electrolyte-containing compositions.
  • the phosphoric acid esters according to the invention are therefore particularly suitable for thickening and stabilizing acidic cosmetic compositions.
  • This can z.
  • B cosmetic compositions containing hydroxy acids, such as lactic acid, glycolic acid, salicylic acid, citric acid or polyglycolic acids in free or partial neutralization.
  • formulations containing vitamin C or vitamin C derivatives, dihydroxyacetone or skin whitening actives such as arbutin or glycyrrhetinic acid and salts thereof can be stabilized.
  • compositions according to the invention have a pH of from 2 to 10, preferably from 2 to 6, particularly preferably from 2.5 to 5 and particularly preferably from 3 to 4.5.
  • compositions according to the invention having a pH of from 2.5 to 5 which, in addition to the phosphoric esters according to the invention and based on the total composition, are from 0.05 to 3.0% by weight, preferably from 0.05 to 2.0 wt .-% and particularly preferably from 0.1 to 1, 0 wt .-% of one or more organic acids having antimicrobial activity, preferably carboxylic acids having antimicrobial activity.
  • organic acids having antimicrobial activity are benzoic acid, sorbic acid, salicylic acid, lactic acid and anisic acid.
  • compositions according to the invention can be used in the compositions according to the invention, preferably in a cosmetic formulation, also in the form of their sodium or potassium salts, if the pH of the composition is later adjusted to a pH of 2.5 to 5. Here, the free, antimicrobial acid is released.
  • these compositions are particularly preferred because, in contrast to the carboxylic acid esters of the prior art in this pH range, the phosphoric acid esters according to the invention enable long-term stable thickening, which makes the use of antimicrobially active acids as preservatives possible in the first place. Thus, other preservatives are more likely to cause skin reactions, e.g. As halogenated preservatives are avoided.
  • the individual organic acids having antimicrobial activity preferably the carboxylic acids having antimicrobial activity, are preferably present in an amount of from 0.05 to 2.0% by weight and more preferably from 0.1 to 1.0% by weight in the above used compositions of the invention, based on the total composition.
  • compositions according to the invention preferably contain water, more preferably in an amount of from 5 to 95% by weight. In a particularly preferred embodiment, they contain from 25 to 85% by weight of water. In a further particularly preferred embodiment, they contain 50 to 95 wt .-% and below again preferably 75 to 95 wt .-% water.
  • the phosphoric acid esters according to the invention are furthermore outstandingly suitable as thickeners of electrolyte-containing compositions.
  • Suitable electrolytes used are inorganic salts, preferably ammonium or metal salts, particularly preferably halides, for example CaCl 2 , MgCl 2 , LiCl, KCl, NaCl, carbonates, hydrogencarbonates, phosphates, sulfates, nitrates, particularly preferably sodium chloride, and / or organic salts.
  • inorganic salts preferably ammonium or metal salts, particularly preferably halides, for example CaCl 2 , MgCl 2 , LiCl, KCl, NaCl, carbonates, hydrogencarbonates, phosphates, sulfates, nitrates, particularly preferably sodium chloride, and / or organic salts.
  • compositions according to the invention may also contain mixtures of different salts.
  • compositions according to the invention comprise one or more electrolytes.
  • aqueous antiperspirant formulations containing aluminum salts, preferably aluminum chlorohydrate or aluminum-zirconium complex salts.
  • the content of the one or more electrolytes in the compositions according to the invention, based on the total composition according to the invention, is preferably from 0.1 to 20.0% by weight, more preferably from 0.2 to 10.0% by weight. %, and more preferably from 0.5 to 5.0% by weight.
  • the phosphoric acid esters of the invention contain compositions which contain oxidizing agents, preferably hydrogen peroxide, for example hair dyes, both thickening and stabilizing.
  • oxidizing agents preferably hydrogen peroxide, for example hair dyes, both thickening and stabilizing.
  • compositions according to the invention comprise hydrogen peroxide or hydrogen peroxide-releasing substances. These compositions are preferably in the form of gels.
  • Suitable hydrogen peroxide-releasing substances are preferably inorganic peracids, preferably peroxosulfuric acid, peroxodisulfuric acid, peroxocarbonates, and organic peracids, preferably peracetic acid.
  • compositions according to the invention are acidic hydrogen peroxide bleaching gels or creams.
  • the compositions of the invention contain, based on the finished cosmetic, pharmaceutical or dermatological compositions, preferably 0.01 to 10.0 wt .-%, particularly preferably 0.1 to 6.0 wt .-% and particularly preferably 0.5 to 3 , 0 wt .-% of the phosphoric acid esters according to the invention.
  • compositions according to the invention may contain anionic, cationic, nonionic, ampholytic surfactants and / or betaine surfactants.
  • the total amount of the surfactants used in the agents according to the invention is, based on the finished compositions according to the invention, preferably 1 to 70% by weight, particularly preferably 5 to 40% by weight. and particularly preferably 10 to 35% by weight.
  • Preferred anionic surfactants are (C 10 -C 22 ) -alkyl and alkylene carboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylamide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkanesulfonates and hydroxyalkanesulfonates, olefin sulfonates, acyl esters of isethionates, ⁇ -sulfofatty acid esters, alkylbenzenesulfonates, alkylphenol glycol ether sulfonates, Sulfosuccinates, sulfosuccinic acid half esters and diesters, fatty alcohol phosphates, fatty alcohol ether phosphates, protein-fatty acid condensation products, alkyl monoglyceride sulfates and sulfonates,
  • the amount of anionic surfactants in the compositions according to the invention is preferably from 2 to 30 wt .-%, particularly preferably from 5 to 25 wt .-% and particularly preferably from 12 to 22 wt .-%, based on the finished compositions.
  • Preferred cationic surfactants are quaternary ammonium salts, such as DKC8-C-22) alkyldimethylammonium chloride or bromide, preferably di (C 8 -C 22 ) -alkyldimethylammonium chloride or bromide; (Cs-C 1-4 alkyldimethylammonium chloride or bromide; (C 8 -C 22 ) alkyltrimethylammonium chloride or bromide, preferably cetyltrimethylammonium chloride or bromide, and (C 8 -C 22 ) -alkyltrimethylammonium chloride or bromide; (Cio-C24) alkyl dimethyl benzyl ammonium chloride or bromide, preferably (C 2 -C 8) alkyl dimethylbenzyl ammonium chloride, (C 8 -C 22) -alkyl-dimethyl- hydroxyethyl ammonium chloride, - phosphate, s
  • the amount of cationic surfactants in the compositions according to the invention is preferably from 0.1 to 10% by weight, more preferably from 0.5 to 7% by weight and especially preferably from 1 to 5% by weight, based on the finished compositions.
  • Preferred nonionic surfactants are fatty alcohol ethoxylates (alkylpolyethylene glycols); Alkylphenolpolyethylenglykole; Fatty amine ethoxylates (alkylaminopolyethylene glycols); Fatty acid ethoxylates (acyl polyethylene glycols); Polypropylenglykolethoxylate (Pluronics ®); Fatty acid alkanolamides, (fatty acid amide polyethylene glycols); Saccharoseester; Sorbitol esters and sorbitan esters and their polyglycol ethers, and C 8 -C 22 -Alkylpolyglucoside.
  • the amount of nonionic surfactants in the compositions according to the invention is preferably in the range from 1 to 20% by weight, more preferably from 2 to 10% by weight and most preferably from 3 to 7 wt .-%, based on the finished compositions.
  • compositions of the invention may contain amphoteric surfactants. These can be described as derivatives of long-chain secondary or tertiary amines having an alkyl group of 8 to 18 carbon atoms and in which another group is substituted with an anionic group which mediates water solubility, such. B. with a carboxyl, sulfate or sulfonate group.
  • Preferred amphoteric surfactants are N- (C-
  • betaine surfactants also called zwitterionic surfactants. These contain in the same molecule a cationic group, in particular an ammonium group and an anionic group, which may be a carboxylate group, sulfate group or sulfonate group.
  • Suitable betaines are preferably alkyl betaines such as coco-betaine or
  • Fatty acid alkylamidopropyl betaines for example
  • the amount of the amphoteric surfactants and / or betaine surfactants in the compositions according to the invention is preferably from 0.5 to 20 wt .-% and particularly preferably from 1 to 10 wt .-%, based on the finished compositions.
  • Preferred surfactants are lauryl sulfate, laureth sulfate, cocoamidopropyl betaine, alkyl betaines such as coco-betaine, sodium cocoyl glutamate and lauroamphoacetate.
  • compositions according to the invention additionally contain, as foam-enhancing agents, co-surfactants from the group of the alkylbetaines, Alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines, amine oxides, fatty acid alkanolamides and polyhydroxyamides.
  • co-surfactants from the group of the alkylbetaines, Alkylamidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines, amine oxides, fatty acid alkanolamides and polyhydroxyamides.
  • the cosmetic, pharmaceutical and dermatological compositions in addition to the one or more phosphoric esters of the invention, contain one or more surfactants.
  • compositions of the invention may be used as further auxiliaries and additives oil body, silicone oils, waxes, emulsifiers, co-emulsifiers, solubilizers, stabilizers, cationic polymers, film formers, thickeners, gelling agents, superfatting agents, moisturizers, antimicrobial agents, biogenic agents, astringents, deodorants, Sunscreen, antioxidants, humectants, solvents, dyes, fragrances, pearlescing agents, opacifiers and / or water-soluble silicones.
  • the oil bodies may advantageously be selected from the groups of triglycerides, natural and synthetic fatty substances, preferably esters of fatty acids with lower C-number alcohols, e.g. As with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids low C number or with fatty acids or from the group of alkyl benzoates, and natural or synthetic hydrocarbon oils.
  • esters of fatty acids with lower C-number alcohols e.g. As with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids low C number or with fatty acids or from the group of alkyl benzoates, and natural or synthetic hydrocarbon oils.
  • triglycerides come from linear or branched, saturated or unsaturated, optionally hydroxylated, C 8 -C 3 o-fatty acids, in particular vegetable oils, such as sunflower, corn, soybean, rice, jojoba, Babusscu-, pumpkin , Grape seed, sesame, walnut, apricot, orange, wheat germ, peach kernel, macadamia, avocado, sweet almond, meadowfoam, castor oil, olive oil, peanut oil, rapeseed oil and coconut oil, as well as synthetic triglyceride oils, e.g. As the commercial product Myritol ® 318. Also hardened triglycerides are inventively preferred.
  • oils of animal origin for example beef tallow, perhydrosqualene, lanolin.
  • oils of animal origin for example beef tallow, perhydrosqualene, lanolin.
  • Another class of oil bodies preferred according to the invention are the benzoic acid esters of linear or branched C ⁇ -22-alkanols, eg. , The commercial products Finsolv ® SB (isostearyl benzoate), Finsolv TN ® (C-12-C15 alkyl benzoate) and Finsolv EB ® (ethylhexyl).
  • Finsolv ® SB isostearyl benzoate
  • Finsolv TN ® C-12-C15 alkyl benzoate
  • Finsolv EB ® ethylhexyl.
  • Another class of oil bodies preferred according to the invention are the
  • di-n-octyl ether (Cetiol ® OE)
  • di-n-nonyl ether di-n-decyl ether, di-n-undecyl ether, di-n-dodecyl ether, n-hexyl-n-octyl ether, n-octyl n -decyl ether, n-decyl-n-undecyl ether, n-undecyl-n-dodecyl ether and n-hexyl-n-undecyl ether, di-3-ethyldecyl ether, tert-butyl-n-octyl ether, iso-pentyl-n-octyl ether and 2-methyl-pent
  • branched saturated or unsaturated fatty alcohols having 6 to 30 carbon atoms for.
  • hydroxycarboxylic acid alkyl esters are full esters of glycolic acid, lactic acid, malic acid, tartaric acid or citric acid. Further basically suitable esters of the hydroxycarboxylic acids are esters of ⁇ -hydroxypropionic acid, tartronic acid, D-gluconic acid, sugar acid, mucic acid or glucuronic acid.
  • esters of Ci 2 -Ci 5 fatty alcohols are particularly preferred. Esters of this type are commercially available, e.g. B. under the trade name Cosmacol ® the EniChem, Augusta Industriale.
  • dicarboxylic acid esters of linear or branched C 2 -C 0 alkanols such as di-n-butyl adipate (Cetiol ® B), di- (2-ethylhexyl) adipate and di- (2-ethylhexyl) -succinate and diol esters such as ethylene glycol dioleate, ethylene glycol di-isotridecanoate, Propylene glycol di- (2-ethylhexanoate), propylene glycol di-isostearate, propylene glycol di-pelargonate, butanediol di-isostearate and neopentyl glycol dicaprylate, and di-isotridecyl acelate.
  • dicarboxylic acid esters of linear or branched C 2 -C 0 alkanols such as di-n-butyl adipate (Cetiol ® B), di
  • oil bodies are symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols, glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC).
  • esters of dimers of unsaturated C 2 -C 22 -fatty acids (dimer fatty acids) with monovalent linear, branched or cyclic C 2 -C 18 -alkanols or with polyfunctional linear or branched C 2 -C 6 -alkanols ,
  • hydrocarbon oils for example those with linear or branched, saturated or unsaturated C 7 -C 4 o-carbon chains, for example Vaseline, dodecane, isododecane, cholesterol, lanolin, synthetic hydrocarbons such as polyolefins, in particular polyisobutene, hydrogenated Polyisobutene, polydecane, and hexadecane, isohexadecane, paraffin oils, isoparaffin oils, e.g. , The commercial products Permethyl ® series, squalane, squalene, and alicyclic
  • Hydrocarbons eg. Example, the commercial product 1, 3-di- (2-ethyl-hexyl) -cyclohexane (Cetiol ® S), ozokerite, and ceresin.
  • silicone oils or waxes are preferably available dimethylpolysiloxanes and cyclomethicones, polydialkylsiloxanes
  • compositions according to the invention may contain waxes, for example paraffin waxes, microwaxes and ozokerites, beeswax and its partial fractions and the beeswax derivatives, waxes from the group of homopolymeric polyethylenes or copolymers of ⁇ -olefins, and natural waxes such as rice wax, candellila wax, carnauba wax, Japan wax or shellac wax.
  • waxes for example paraffin waxes, microwaxes and ozokerites, beeswax and its partial fractions and the beeswax derivatives
  • waxes from the group of homopolymeric polyethylenes or copolymers of ⁇ -olefins and natural waxes such as rice wax, candellila wax, carnauba wax, Japan wax or shellac wax.
  • non-ionic, anionic, cationic or amphoteric surface-active compounds can be used.
  • nonionic surface-active compounds are preferably considered:
  • Polyglycerol polyricinoleate and polyglycerol poly-12-hydroxystearate are also preferably suitable.
  • anionic co-emulsifiers such as mono-, di- or tri-phosphoric acid esters, soaps (for example, sodium stearate), fatty alcohol sulfates but also cationic emulsifiers such as mono-, di- and tri-alkyl quats and their polymeric derivatives.
  • amphoteric emulsifiers are preferably available Alkylaminoalkylcarbonklaren, betaines, sulfobetaines and imidazoline derivatives.
  • fatty alcohol ethoxylates selected from the group consisting of the ethoxylated stearyl alcohols, isostearyl alcohols, cetyl alcohols, isocetyl alcohols, oleyl alcohols, lauryl alcohols, isolauryl alcohols, cetylstearyl alcohols, in particular polyethylene glycol (13) stearyl ether, polyethylene glycol (14) stearyl ether, polyethylene glycol (15) stearyl ether, polyethylene glycol ( 16) stearyl ether, polyethylene glycol (17) stearyl ether, polyethylene glycol (18) stearyl ether, polyethylene glycol (19) stearyl ether, polyethylene glycol (20) stearyl ether, polyethylene glycol (12) isostearyl ether, polyethylene glycol (13) isostearyl ether, polyethylene glycol (14) isostearyl ether, polyethylene glycol (15) isostearyl ether, polyethylene glycol (15) isoste
  • fatty acid ethoxylates selected from the group consisting of ethoxylated stearates, isostearates and oleates, in particular polyethylene glycol (20) stearate, polyethylene glycol (21) stearate, polyethylene glycol (22) stearate, polyethylene glycol (23) stearate, polyethylene glycol (24) stearate, polyethylene glycol ( 25) stearate, polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate, polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate, polyethylene glycol (16) isostearate, polyethylene glycol (17) isostearate, polyethylene glycol (18) isostearate, polyethylene glycol (19) isostearate, polyethylene glycol (20) isostearate, polyethylene glycol (21) isostearate, polyethylene glycol (22) isostearate, polyethylene glycol (23) isostearate, polyethylene glycol (24) isostearate, polyethylene glycol
  • the sodium laureth-11-carboxylate can be advantageously used.
  • polyethylene glycol (60) evening phimosis glycerides can be advantageously used. Furthermore, it is advantageous to use the polyethylene glycol glycerol fatty acid esters from the group polyethylene glycol (20) glyceryl laurate,
  • sorbitan esters particularly suitable are polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • co-emulsifiers are glyceryl monostearate, glyceryl monooleate, diglyceryl monostearate, glyceryl isostearate, polyglyceryl-3-oleate, polyglyceryl-3-diisostearate, polyglyceryl-4-isostearate, polyglyceryl-2-dipolyhydroxystearate, polyglyceryl-4-dipolyhydroxystearate, PEG-30-dipolyhydroxystearate, diisostearoylpolyglyceryl 3-diisostearate, glycol distearate and polyglyceryl-3-dipolyhydroxystearate, sorbitan monoisostearate, sorbitan stearate, sorbitan oleate, sucrose distearate, lecithin, PEG-7 hydrogenated castor oil, cetyl alcohol, stearyl alcohol, behenyl alcohol, isobehenyl alcohol and polyethylene glycol (2) stearyl
  • compositions of the invention may contain one or more of the emulsifiers, co-emulsifiers or solubilizers in amounts of 0.1 to 20 wt .-%, preferably 1 to 15 wt .-% and particularly preferably 3 to 10 wt .-%, based on the finished compositions.
  • metal salts of fatty acids such as. As magnesium, aluminum and / or zinc stearate, preferably in amounts of 0.1 to 10 wt .-%, preferably 0.5 to 8 wt .-% and particularly preferably 1 to 5 wt .-%, based on the finished compositions.
  • Suitable cationic polymers are those known by the INCI name "Polyquaternium", in particular Polyquaternium-31, Polyquaternium-16, Polyquaternium-24, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-28, Polyquaternium-2, Polyquaternium -10, Polyquaternium-11, Polyquaternium 37 & mineral oil & PPG trideceth (Salcare SC95), PVP-dimethylaminoethyl methacrylate copolymer, guar hydroxypropyl triammonium chlorides, calcium alginate and ammonium alginate, cationic cellulose derivatives, cationic starch, copolymers of diallyl ammonium salts and acrylamides quaternized vinylpyrrolidone / vinylimidazole polymers; condensation products of polyglycols and amines; quaternized collagen polypeptides; quaternized wheat polypeptides; polyethylenimines;
  • Copolymers of adipic acid and dimethylaminohydroxy-propyldiethylenetriamine Polyaminopolyamide and cationic chitin derivatives such as chitosan.
  • compositions according to the invention may contain one or more of the abovementioned cationic polymers in amounts of from 0.1 to 5% by weight, preferably from 0.2 to 3% by weight and more preferably from 0.5 to 2% by weight, based on the finished compositions.
  • compositions of the invention may contain film formers, which are selected depending on the application of salts of
  • Phenylbenzimidazole sulfonic acid for example C 10-polycarbamylpolyglyceryl esters, polyvinyl alcohol, water-soluble acrylic acid polymers / copolymers or their esters or salts, for example partial acrylic or methacrylic acid, water-soluble cellulose, for example hydroxymethyl cellulose, hydroxyethyl cellulose,
  • Hydroxypropyl cellulose water-soluble quaternium, polyquaternium, carboxyvinyl polymers, such as carbomers and their salts, polysaccharides, for example polydextrose and glucan, vinyl acetate / crotonate, 60 (Clariant) available for example under the trade name Aristoflex ® A.
  • compositions according to the invention may contain one or more film formers in amounts of from 0.1 to 10% by weight, preferably from 0.2 to 5% by weight and more preferably from 0.5 to 3% by weight, based on the finished product Compositions included.
  • the desired viscosity of the compositions can be adjusted by adding thickeners and gelling agents.
  • Cellulose ethers and other cellulose derivatives for example carboxymethylcellulose, hydroxyethylcellulose), gelatin, starch and starch derivatives, sodium alginates, fatty acid polyethylene glycol esters, agar-agar, tragacanth or dextrin derivatives, in particular dextrin esters, are preferably suitable.
  • metal salts of fatty acids preferably having 12 to 22 carbon atoms, for example sodium stearate, sodium palmitate, sodium laurate, sodium arachidates, sodium behenate, potassium stearate, potassium palmitate, sodium myristate, aluminum monostearate, hydroxyfatty acids, for example 12-hydroxystearic acid, 16-hydroxyhexadecanoic acid; fatty acid amides; fatty acid; Dibenzal sorbitol and alcohol-soluble polyamides and polyacrylamides or mixtures thereof.
  • crosslinked and uncrosslinked polyacrylates such as carbomer, sodium polyacrylates or sulfonic acid-containing polymers such as Ammoniumacryloyldimethyltaurate / VP copolymer can be used.
  • compositions according to the invention preferably contain from 0.01 to 20% by weight, more preferably from 0.1 to 10% by weight, particularly preferably from 0.2 to 3% by weight and very particularly preferably from 0.4 to 2% by weight. % of thickeners or gelling agents.
  • Lanolin and lecithin, nonethoxylated and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, mono-, di- and triglycerides and / or fatty acid alkanolamides may preferably be used as superfatting agents.
  • the latter simultaneously serving as foam stabilizers which are preferably used in amounts of from 0.01 to 10% by weight, more preferably from 0.1 to 5% by weight and especially preferably from 0.5 to 3% by weight. %, based on the finished compositions of the invention.
  • Antimicrobial agents include cetyltrimethylammonium chloride, cetylpyridinium chloride, benzethonium chloride, diisobutylethoxyethyldimethylbenzylammonium chloride, sodium N-laurylsarcosinate, sodium N-palmethyl sarcosinate, lauroylsarcosine, N-myristoylglycine, potassium N-laurylsarcosine, trimethylammonium chloride, sodium aluminum chlorohydroxylactate, triethyl citrate, tricetylmethylammonium chloride, 2,4,4'- Trichloro-2'-hydroxydiphenyl ether (triclosan), phenoxyethanol, 1, 5-pentanediol, 1, 6-hexanediol, 3,4,4'-trichlorocarbanilide (triclocarban), diaminoalkylamide, for example L-lysinehexadecylamide, citrate heavy metal salts,
  • Propylparaben, and their Na salts pentanediol 1, 2-octanediol, 2-bromo-2-nitropropane-1, 3-diol, ethyl hexylglycerin, benzyl alcohol, sorbic acid, benzoic acid, lactic acid, imidazolidinylurea, Diazolidinylhamstoff, Dimethyloldimethylhydantoin (DMDMH), Na -SaIz of hydroxymethylglycinate, hydroxyethylglycine of sorbic acid and combinations of these active substances used.
  • compositions of the invention preferably contain the antimicrobial agents in amounts of 0.001 to 5 wt .-%, particularly preferably from 0.01 to 3 wt .-% and particularly preferably from 0.1 to 2 wt .-%, based on the finished compositions ,
  • compositions of the invention may further biogenic agents selected from plant extracts such as aloe vera, as well as local anesthetics, antibiotics, anti-inflammatories, anti-allergic agents, corticosteroids, sebostatics, bisabolol ®, allantoin, phytantriol ®, proteins, vitamins selected from niacin, biotin, vitamin B2 , Vitamin B3, Vitamin B6, Vitamin B3 derivatives
  • Vitamin E and / or its derivatives preferably as the sodium salt of the monophosphoric acid ester of ascorbic acid or as the magnesium salt of the phosphoric acid ester of ascorbic acid, tocopherol and tocopherol acetate, and Vitamin E and / or its derivatives.
  • compositions according to the invention may contain biogenic active substances preferably in amounts of from 0.001 to 5% by weight, more preferably from 0.01 to 3% by weight and especially preferably from 0.1 to 2% by weight, based on the finished compositions, contain.
  • compositions of the invention may astringents, preferably magnesium oxide, alumina, titania, zirconia and zinc oxide, oxide hydrates, preferably alumina hydrate (boehmite) and hydroxides, preferably of calcium, magnesium, aluminum, titanium, zirconium or zinc, and
  • Aluminum chlorohydrates preferably in amounts of 0 to 50 wt .-%, particularly preferably in amounts of 0.01 to 10 wt .-% and particularly preferably in amounts of 0.1 to 10 wt .-%.
  • Preferred deodorants are allantoin and bisabolol. These are preferably used in amounts of 0.0001 to 10 wt .-%.
  • compositions according to the invention can be used as pigments / micropigments and as sunscreen filters microfine titanium dioxide, Mica titanium oxide, iron oxides, mica iron oxide, zinc oxide, silicon oxides, ultramarine blue, chromium oxides.
  • compositions of the invention may contain sunscreen filters, preferably selected from 4-aminobenzoic acid,
  • the amount of the aforementioned sunscreen filters (one or more compounds) in the compositions is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight and in particular from 1 to 10% by weight, based on the total weight of the finished composition.
  • compositions according to the invention may contain antioxidants, preferably selected from amino acids (eg glycine, histidine, tyrosine, Tryptophan) and their derivatives, imidazoles (eg urocanic acid) and derivatives thereof, peptides such as DL-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg.
  • amino acids eg glycine, histidine, tyrosine, Tryptophan
  • imidazoles eg urocanic acid
  • peptides such as DL-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine)
  • carotenoids eg.
  • ⁇ -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and its derivatives, lipoic acid and derivatives thereof (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, cystine, Cystamine and its glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate , Distearyl thiodipropionate, thiodipropionic acid and its derivatives (eg, esters, ethers, peptides, lipids, nucleotides, nucleosides and salt
  • ⁇ -hydroxy fatty acids palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids eg citric acid, lactic acid, malic acid
  • humic acid bile acids, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and derivatives eg ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate
  • tocopherols and derivatives e.g.
  • Vitamin E acetate Vitamin E acetate
  • vitamin A and derivatives vitamin A palmitate
  • Koniferylbenzoat the benzoin, rutinic acid and derivatives thereof, ⁇ -glycosylrutin, ferulic acid, furfurylidenglucitol, camosine, butylhydroxytoluene, butylated hydroxyanisole, Nordihydroguajakharzklazklare, Nordihydroguajaretklare, trihydroxybutyrophenone, uric acid and their derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnSO 4 ), selenium and its derivatives (eg Selenm ethionine), stilbenes and their derivatives (e.g. B.
  • stilbene oxide e.g., trans-stilbene
  • superoxide dismutase e.g., sodium metabisulfite
  • inventively suitable derivatives salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • the antioxidants can protect the skin and hair from oxidative stress.
  • Preferred antioxidants are vitamin E and its derivatives as well as vitamin A and its derivatives.
  • the amount of the one or more antioxidants in the compositions of the invention is preferably from 0.001 to 30% by weight, more preferably from 0.05 to 20% by weight, and most preferably from 1 to 10% by weight, based on the total weight of the composition ,
  • humectants selected from the sodium salt of 2-pyrrolidone-5-carboxylate (NaPCA), guanidine; Glycolic acid and its salts, lactic acid and its salts, glucosamines and their salts,
  • D-panthenol R-2,4-dihydroxy-N- (3-hydroxypropyl) -3,3-dimethylbutamide
  • DL-panthenol calcium pantothenate
  • panthetin pantotheine
  • Panthenylethylether isopropyl palm
  • compositions of the invention may contain organic solvents.
  • organic solvents In principle, all mono- or polyhydric alcohols are suitable as organic solvents. Alcohols having 1 to 4 carbon atoms, such as ethanol, propanol, isopropanol, n-butanol, i-butanol, t-butanol, glycerol and mixtures of the alcohols mentioned are preferably used. More preferred alcohols are polyethylene glycols having a molecular weight less than 2,000. In particular, use of polyethylene glycol having a molecular weight of between 200 and 600 and up to 45% by weight and polyethylene glycol having a molecular weight of between 400 and 600 in amounts of 5 to 25 wt .-% preferred. Other suitable solvents include triacetin (glycerol triacetate) and 1-methoxy-2-propanol.
  • compositions of the invention both organic and inorganic dyes are known from the corresponding positive list of the Cosmetics Regulation or EC List of cosmetic colorants. Also advantageous are oil-soluble natural dyes such. B. paprika extracts, beta-carotene and cochineal.
  • Pearlescent pigments eg. As fish silver (guanine / hypoxanthine mixed crystals from fish scales) and mother of pearl (ground mussel shells), monocrystalline pearlescent pigments such.
  • effect pigments are to be understood as meaning pigments which, by virtue of their refractive properties, cause particular optical effects. Effect pigments lend the treated surface (skin, hair, mucous membrane) gloss or glitter effects or can optically hide skin irregularities and skin wrinkles through diffuse light scattering. As a particular embodiment of the effect pigments, interference pigments are preferred. Particularly suitable effect pigments are, for example, mica particles coated with at least one metal oxide. Besides mica, one
  • Phyllosilicate, silica gel and other SiO 2 modifications are suitable as a carrier.
  • a metal oxide frequently used for coating is, for example, titanium oxide, to which iron oxide may be added, if desired.
  • the size and shape (eg spherical, ellipsoidal, flattened, even, uneven) of the pigment particles as well as the thickness of the oxide coating allows the
  • Reflective properties are influenced.
  • Other metal oxides eg. B. bismuth oxychloride (BiOCl), and the oxides of, for example, titanium, in particular the TiO 2 -MOd ifat anatase and rutile, aluminum, tantalum, niobium, zirconium and hafnium.
  • magnesium fluoride (MgF 2 ) and calcium fluoride (fluorspar, CaF 2 ) effect pigments can be produced.
  • the effects can be controlled both by the particle size and by the particle size distribution of the pigment ensemble. Suitable particle Size distributions are sufficient for. From 2 to 50 ⁇ m, from 5 to 25 ⁇ m, from 5 to 40 ⁇ m, from 5 to 60 ⁇ m, from 5 to 95 ⁇ m, from 5 to 100 ⁇ m, from 10 to 60 ⁇ m, from 10 to 100 ⁇ m, from 10 to 125 ⁇ m, and from 20 to 20 ⁇ m. 100 ⁇ m, 20-150 ⁇ m and ⁇ 15 ⁇ m. A broader particle size distribution z. Example, from 20 to 150 microns, glittering effects, while a narrower particle size distribution of ⁇ 15 microns ensures a uniform silky appearance.
  • compositions according to the invention preferably contain effect pigments in amounts of from 0.1 to 20% by weight, more preferably from 0.5 to 10% by weight and particularly preferably from 1 to 5% by weight, based in each case on the total weight of the composition ,
  • Preferred deodorants are allantoin and bisabolol. These are preferably used in amounts of 0.0001 to 10 wt .-%.
  • fragrance or perfume oils can individual fragrance compounds, eg.
  • ethers, aldehydes, ketones, alcohols and hydrocarbons are used.
  • Fragrance compounds of the ester type are e.g. Benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethylacetate, linalylbenzoate, benzylformate, ethyl-methylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate.
  • the ethers include, for example, benzyl ethyl ether to the aldehydes z.
  • linear alkanals having 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cycloalanine, Hydroxycitronellal, Lilial and Bourgeonal, to the ketones z.
  • ionone alpha-lsomethylionon and methyl cedryl ketone
  • the hydrocarbons mainly include the terpenes and balsams.
  • mixtures of different fragrances are used, which together produce an attractive fragrance.
  • Perfume oils may also contain natural fragrance mixtures, such as those available from plant or animal sources, e.g. Pine, citrus, jasmine, lily, rose, or ylang-ylang oil. Also essential oils lesser Volatility, which are mostly used as aroma components, are useful as perfume oils, e.g. B. sage oil, camomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil and ladanum oil.
  • perfume oils e.g. B. sage oil, camomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil and ladanum oil.
  • pearlescing component are preferably suitable fatty acid monoalkanolamides, fatty acid dialkanolamides, monoesters or diesters of alkylene glycols, in particular ethylene glycol and / or propylene glycol or its oligomers, with higher fatty acids, such as. As palmitic acid, stearic acid and behenic acid, monoesters or polyesters of glycerol with carboxylic acids, fatty acids and their metal salts, ketosulfones or mixtures of said compounds. Particularly preferred are ethylene glycol distearates and / or polyethylene glycol distearates with an average of 3 glycol units.
  • compositions according to the invention contain pearlescing compounds, they are preferably present in an amount of from 0.1 to 15% by weight and more preferably in an amount of from 1 to 10% by weight in the compositions according to the invention.
  • acids or alkalis for pH adjustment are preferably
  • Mineral acids for example HCl
  • inorganic bases for example NaOH or KOH
  • organic acids preferably citric acid used.
  • Phosphoric acid (85% strength), diol and fatty alcohol ethoxylate are used in a specific molar ratio in the preparation of the phosphoric acid esters according to the invention.
  • all starting materials are initially charged in a stirred apparatus with a heating mushroom, a descaling unit with a condenser and a vacuum connection.
  • the mixture is heated to 100 0 C, evacuated three times to 100 mbar and then belübftet with nitrogen again.
  • inerting nitrogen inlet of 20 liters / hour
  • the mixture is heated under nitrogen inlet to 230 0 C and esterified (water discharge).
  • reaction times are from 24 to 42 hours (calculated from 230 ° C. esterification temperature), in particular 40 hours.
  • the residual acid number is then ⁇ 3 mg KOH / g. This corresponds to about 93 to 96% conversion (based on starting acid number).
  • the product is cooled to 80 0 C, poured into a dish and crushed the solidified melt.
  • Esters of 11, 5 g of phosphoric acid, 197.5 g of polyglycol 4000 and 296.0 g Ceteareth- 25 (C 6 / i 8 fatty alcohol + 25 moles ethylene oxide) in a molar ratio 2: 1: 4 (Formula E 2), residual Acid value: 1.5 mg KOH / g (96% conversion), 31 P-NMR: diester / triester 13/87 mol%.
  • esters of 15.4 g phosphoric acid, 395.1 g polyglycol 4000 and 293.3 g ceteareth-25 (C 16 / i 8 fatty alcohol + 25 mol ethylene oxide) in the molar ratio 4: 3: 6 (formula E 2 M 2 and E 3 V), residual acid number: 2.3 mg KOH / g (93% conversion), 31 P-NMR: diester / triester 18/82 mol%.
  • esters of 1 1, 5 g of phosphoric acid, 409.5 g of polyglycol 8000, and 296.0 g Ceteareth- 25 (C 6/18 fatty alcohol + 25 moles ethylene oxide) in a molar ratio 2: 1: 4 (Formula E 2), residual Acid value: 1, 1 mg KOH / g (95% conversion), 31 P-NMR: diester / triester 13/87 mol%.
  • Example 8 Example 8:
  • PEG-150 pentaerythrityl tetrastearate (Crothix)
  • PEG-150 Polyglyceryl-2 tristearate (Genapol ® DAT 100)
  • PEG 150 distearate (Rewopal ® PEG 6000 DS)
  • the viscosity was measured at 20 0 C with a Brookfield viscometer type RVT at 20 rpm measured immediately after preparation of the solutions to be measured ( "viscosity immediately”) and after storage of the corresponding solutions.
  • Table 1 Viscosity 6 wt .-% aqueous solutions of Preparation Examples 1 to 11 compared to market products
  • Phosphoric acid esters according to Example 1 to 11 compared to the comparative examples on the one hand give clear gels of high viscosity in water, on the other hand is the
  • Table 2 Viscosity 1% by weight solution in sodium laureth ether sulfate with 2 ethylene oxide units (INCI: sodium laureth sulfate): cocamidopropyl betaine 8: 2, 15% by weight active substance sodium laureth sulfate / cocamidopropyl betaine, pH 4 - 4.4
  • Polyglycol 400 (Clariant) 2.00% PEG-8 Panthenol 0.50%
  • Nipagin M ® (Clariant) 0.20% to
  • Methylparaben ascorbic acid-2-glucoside 2.00%
  • Genapol ® LRO liquid (Clariant) 30.00% Sodium Laureth Sulfate Hostapon ® CGN (Clariant) 5.00% Sodium Cocoyl Glutamate Perfume 0.30%
  • Genagen CAB ® (Clariant) 6.00% Cocamidopropyl Betaine
  • Nipaguard ® PDU (Clariant) qs Propylene Glycol (and) Diazolidinyl Urea (and) methylparaben
  • Trideceth-9 PG Amodimethicone and Trideceth-12 production
  • Formulation Example 12 showed a marked reduction in white residue on clothing after application of skin roll-on to the same formulation but without the phosphoric acid ester of Example 2.
  • Genapol ® LA 030 (Clariant) to 1.50%
  • Genagen ® KB (Clariant) 6.00%
  • Phenonip ® (Clariant) of 0.50% phenoxyethanol (and) Methylparaben (and) Ethylparaben
  • Formulation example 16 (O / W self-tanning cream)
  • Phenonip ® (Clariant) of 0.50%
  • Phenonip ® (Clariant) of 0.50%
  • Genapol ® LRO liquid (Clariant) 30.00% Sodium Laureth Sulfate Hostapon ® CGN (Clariant) 5.00% Sodium Cocoyl Glutamate Perfume 0.30%
  • Genagen CAB ® (Clariant) 8.00%
  • Genagen ® CAB (Clariant) 6, .00%

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Abstract

L'invention concerne des esters d'acide phosphorique contenant A) un ou plusieurs motifs constitutifs dérivés de substances du constituant a) qui sont sélectionnées parmi l'acide orthophosphorique et un ou plusieurs de ses dérivés, B) un ou plusieurs motifs constitutifs dérivés de substances du constituant b) qui sont sélectionnées parmi un ou plusieurs composés de formule (I) R2-O-(CH2CH2O)u(C3H6O)v(DO)w-H et C) un ou plusieurs motifs constitutifs dérivés de substance du constituant c) qui sont sélectionnées parmi un ou plusieurs diols de formule (II) HO-(CH2CH2O)a(C3H6O)b(DO)c-H, la somme a + b + c étant supérieure ou égale à 1 et les esters d'acide phosphorique contenant au moins deux atomes de phosphore par molécule, pontés par l'intermédiaire d'un motif constitutif dérivé des composés de formule (II). Les esters d'acide phosphorique selon l'invention peuvent être utilisés de manière avantageuse pour la production de compositions cosmétiques, pharmaceutiques et dermatologiques.
EP08785166A 2007-08-02 2008-07-29 Esters d'acide phosphorique contenant des atomes de phosphore pontés par l'intermédiaire de motifs diol Withdrawn EP2176349A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE200710036183 DE102007036183A1 (de) 2007-08-02 2007-08-02 Phosphorsäureester enthaltend über Diol-Einheiten verbrückte Phosphoratome
DE200810006855 DE102008006855A1 (de) 2008-01-31 2008-01-31 Phosphorsäureester enthaltend über Diol-Einheiten verbrückte Phosphoratome
PCT/EP2008/006218 WO2009015856A2 (fr) 2007-08-02 2008-07-29 Esters d'acide phosphorique contenant des atomes de phosphore pontés par l'intermédiaire de motifs diol

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US8686033B2 (en) 2014-04-01
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JP2010535254A (ja) 2010-11-18
WO2009015856A3 (fr) 2010-03-18
US20110003010A1 (en) 2011-01-06
CN101802097B (zh) 2012-11-14

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