WO2012028527A1 - Épaississants associatifs pour préparations aqueuses - Google Patents

Épaississants associatifs pour préparations aqueuses Download PDF

Info

Publication number
WO2012028527A1
WO2012028527A1 PCT/EP2011/064607 EP2011064607W WO2012028527A1 WO 2012028527 A1 WO2012028527 A1 WO 2012028527A1 EP 2011064607 W EP2011064607 W EP 2011064607W WO 2012028527 A1 WO2012028527 A1 WO 2012028527A1
Authority
WO
WIPO (PCT)
Prior art keywords
phase
polyether
compound
preparations
oil
Prior art date
Application number
PCT/EP2011/064607
Other languages
German (de)
English (en)
Inventor
Holger TÜRK
Volker Wendel
Anna Cristadoro
Rabie Al-Hellani
Bernd Bruchmann
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to CN2011800418498A priority Critical patent/CN103124754A/zh
Priority to BR112013004660A priority patent/BR112013004660A2/pt
Priority to EP11754335.5A priority patent/EP2611845A1/fr
Priority to JP2013526415A priority patent/JP2013537921A/ja
Priority to AU2011298459A priority patent/AU2011298459A1/en
Priority to KR1020137005311A priority patent/KR20140001825A/ko
Priority to MX2013002262A priority patent/MX2013002262A/es
Priority to RU2013113873/04A priority patent/RU2013113873A/ru
Priority to CA2810099A priority patent/CA2810099A1/fr
Publication of WO2012028527A1 publication Critical patent/WO2012028527A1/fr

Links

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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/84—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
    • A61K8/87—Polyurethanes
    • 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
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/003—Dendrimers
    • C08G83/004—After treatment of dendrimers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning 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
    • 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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal

Definitions

  • the invention relates to associative thickeners based on compounds comprising at least one hydrophobically modified polyether dendron as end group.
  • the associative thickeners are compounds with pronounced hydrophilic and hydrophobic segments, which, owing to their segmented structure, are capable of producing more or less of themselves and / or the coating constituents (binders, pigments, fillers, etc.) to form less stable associates.
  • the chemical structure it is possible in principle to vary the stability of the associates and thus the rheological properties of a coating system.
  • the best known associative thickeners are polyurethane-based polymers, the so-called HEUR thickeners ("nonionic hydrophobically modified ethylene oxide urethane block copolymer").
  • HEUR thickeners nonionic hydrophobically modified ethylene oxide urethane block copolymer
  • the associative thickeners of the HEUR type already described in the late seventies in US 4079028 (Rohm & Haas) are composed of linear and / or branched polyethylene glycol blocks and hydrophobic segments, which are generally linked together via urethane groups.
  • the thickening effect of the conventional HEUR thickeners is based on the fact that the hydrophilic polyethylene glycol sections ensure water compatibility and the hydrophobic sections build up a viscosity-giving three-dimensional molecular composite via an association.
  • EP 761780 and EP 1 1 1014 (Asahi Denka) describe polyurethane thickeners composed of polyethylene glycols as internal hydrophilic building blocks, linear diisocyanates as internal hydrophobic building blocks and ethoxylated, alkyl chain-branched alcohols as hydrophilic hydrophobic chain ends. Associative thickeners are used in many fields, increasingly in cosmetics.
  • EP 1584331 and EP 1013264 (Shiseido) essentially describe the use of the polyurethanes described in the aforementioned EP 761780 as thickeners for cosmetic preparations.
  • WO 2006/002813 (Cognis) describes polyurethane thickeners for various applications in aqueous media.
  • the thickeners comprise hydrophilic polyols having at least two hydroxyl groups, one or more hydrophobic compounds, such as long-chain alcohols, and at least difunctional isocyanates. An excess of NCO groups causes branching in the interior of the chain.
  • These polyurethanes are used, for example, in cosmetic preparations.
  • WO 02/88212 (Cognis) describes polyurethanes of ethoxylated long-chain alcohols and cyclic diisocyanate oligomers, for example isocyanurates and their use in cosmetics.
  • EP 725097 (Bayer) describes polyurethane thickeners in the preparation of which polyethers, produced by alkoxylation of alcohols or alkylphenols, are reacted with polyisocyanates, the ratio of NCO to OH equivalents in the range from 0.9: 1 to 1.2 1 lies. These thickeners are proposed, for example, for use in aqueous emulsion paints.
  • WO 2009/135856 and WO 2009/135857 describe water-dispersible polyurethanes having a substantially linear backbone composed of alternating hydrophilic and hydrophobic sections and their uses, for example in cosmetics.
  • DE 102008030992 relates to linear dendritic polyglycerol compounds, processes for their preparation and their use for the solubilization of hydrophobic substances, in particular as a carrier or transport system for active substances and / or signal substances.
  • the object of the present invention was to provide thickeners with specific properties which are suitable for cosmetic preparations.
  • the desired properties of such thickeners include, for example:
  • the present invention thus relates to compounds containing at least one group of the general formula (I)
  • R 1 independently of one another are C 4 -C 40 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 30 -aryl, C 7 -C 40 -aralkyl, C 7 -C 40 -alkylaryl or - (R 2 -O) n -R 3 ;
  • R 2 , R 4 independently of one another are C 2 -C 10 -alkylene, C 6 -C 10 -arylene, or C 7 -C 10 -arylalkylene;
  • R 3 H, Ci-C 40 alkyl, C 3 -C 0 cycloalkyl, C 6 -C 30 aryl, C 7 -C 40 aralkyl or C 7 -C 40 - alkylaryl;
  • n 1 to 200;
  • the end group can be linked to the remaining compound instead of via O also via NR 5 , with R 5 selected from H and C 1 -C 30 -alkyl.
  • the compound is a polycondensate, ie a polymer whose monomer units are linked with elimination of water.
  • the polycondensate may have a linear, branched, hyperbranched or dendritic structure.
  • the polycondensate preferably has a linear or slightly branched structure.
  • the polycondensates according to the invention include, in addition to all polycondensates which have only one type of bond between the monomer units within their molecules, such as urethane bond, urea bond, ester bond, amide bond or carbonate bond, and also such polycondensates which simultaneously have at least two different bonds within their molecules between their monomer building blocks such as urethane bond and ester bond or urethane bond and urea bond or urea bond and ester bond.
  • Preferred compounds are selected from polyurethanes, polyureas, polyesters, polyamides and polycarbonates, more preferably from polyurethanes, polycarbonates, polyesters, polyester polyurethanes, polyester polycarbonates, polyether polyurethanes, and polyether polycarbonates.
  • polyurethanes may, however, additionally and additionally comprise other types of bonds between the individual building blocks.
  • polyurethanes in addition to urethane linkages resulting from the reaction between R-NCO and R'-OH, polyurethanes also include urea linkages resulting from the reaction between R-NCO and R'-NH.
  • Preferred compounds of the present invention are polyurethanes.
  • Preferred polyurethanes are selected from polyetherurethanes and polyesterurethanes.
  • Polyols contain at least 2 OH groups.
  • the polyurethanes according to the invention comprise at least one polyol in copolymerized form, the polyol having a number average molecular weight M n in the range from 400 to 12,000 g / mol, more preferably from 400 to 10,000 g / mol.
  • Preferred polyols are polyester polyols and polyether polyols.
  • Polyesterpolyols contain, as hydrophilic sections, polyester polyols (also referred to as “polyesterols”) in a condensed form Polyesterpolyols contain per molecule at least two OH groups and at least two ester groups, the number average molecular weight M n of these compounds is preferably at least 400 g / mol Preferred polyester polyols have a number average molecular weight M n in the range from 400 to 5000 g / mol, more preferably from 400 to 2000 g / mol.
  • Polyester polyols are typically produced by the reaction of dicarboxylic acids with polyols at high temperature. Hints for the industrial production of polyester polyols can be found, for example, in the Kunststoffhandbuch Polyurethane, edited by G. Oertel, 3rd ed. 1993, Verlag Carl Hanser, Chap. 3.1 .2, in particular Chap. 3.1.2.3, are taken.
  • Polyether polyurethanes contain hydrophilic sections polyether polyols in a condensed form.
  • Polyether polyols also called “polyetherols”
  • Polyether polyols are usually so hydrophilic that they are water-soluble at room temperature (20 ° C).
  • the preparation of polyether alcohols is described in M. Lonescu, "Chemistry and Technology of Polyols for Polyurethanes", Rapra Technology, 2005.
  • Frequently used alkylene oxide starting materials for the preparation of polyetherols are propylene oxide (PO) and / or ethylene oxide (EO).
  • PO propylene oxide
  • EO ethylene oxide
  • the following starters are suitable: a) monoethylene glycol, diethylene glycol, trietylene glycol, PEG, monopropylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, polytetrahydrofuran, glycerol, trimethylolpropane, trimethylolethane, neopentyl glycol, sugars and sugar derivatives such as sucrose or sorbitol, bisphenol A, bisphenol F, pentaerythritol, degraded starch, water , Mixtures thereof; b) amines, such as ethylenediamine, triethanolamine or toluenediamine,
  • the alkylene oxide used is preferably propylene oxide, ethylene oxide, butylene oxide, isobutylene oxide, styrene oxide or mixtures of at least two of the alkylene oxides mentioned.
  • the alkylene oxide used is preferably propylene oxide, ethylene oxide or mixtures of propylene oxide and ethylene oxide. Particular preference is given to using ethylene oxide as the alkylene oxide.
  • the process can be carried out using different alkylene oxides as random or as a block copolymerization.
  • Particularly suitable polyetherols are, for example, the polymerization products of ethylene oxide (EO), their mixed or graft polymerization products and the polyethers obtained by condensation of polyhydric alcohols or mixtures thereof and those obtained by ethoxylation of polyhydric alcohols, amides, polyamides and aminoalcohols.
  • EO ethylene oxide
  • polyethers obtained by condensation of polyhydric alcohols or mixtures thereof and those obtained by ethoxylation of polyhydric alcohols, amides, polyamides and aminoalcohols.
  • polyethylene glycols polyethylene glycols
  • addition products of ethylene oxide onto trimethylolpropane or EO-propylene oxide (PO) block copolymers are examples of these.
  • polyether polyols containing at least predominantly polyethylene glycol.
  • Suitable examples are polyethylene glycols having an average content of EO units in the range from 30 to 450 per polymer molecule.
  • Suitable polyether polyols are also those having more than 2 hydroxyl groups. These are obtainable for example by addition of EO and / or PO to polyhydric alcohols such as glycerol, trimethylolpropane, trimethylolethane, sugars and sugar derivatives such as sucrose or sorbitol, pentaerythritol or amines.
  • polyhydric alcohols such as glycerol, trimethylolpropane, trimethylolethane, sugars and sugar derivatives such as sucrose or sorbitol, pentaerythritol or amines.
  • polyether polyols provide branching sites within the compounds of the invention through the free OH groups. Preference is given to polyols of the general formula HO- (CH 2 -CH 2 -O) n -H, where n can assume the values in the range from 30 to 450.
  • the polyetherols preferably have M n values in the range from 1500 to 12000 g / mol, more preferably up to 10000 g / mol.
  • the polyurethanes obtainable by the process according to the invention thus comprise at least one polymerized polyether polyol, wherein the at least one polyether polyol has a number average molecular weight M n in the range from 1500 to 12000 g / mol, more preferably from 4000 to 10000 g / mol.
  • the polymerized polyetherols have a number average molecular weight M n in the range of 6000 g / mol to 9000 g / mol.
  • the polyetherols to be polymerized into the polyurethanes have a number average molecular weight M n in the range from 5800 to 6200 g / mol.
  • the polyetherols to be polymerized into the polyurethanes have a number average molecular weight M n in the range from 8800 to 9200 g / mol.
  • the polyurethanes of the invention may also contain copolymerized low molecular weight compounds having at least 2 hydroxyl groups or at least 2 amine groups. Such low molecular weight compounds having 2 hydroxyl or amine groups are generally referred to as chain extenders, may be functionalized with ionic groups and are known in the art. Low molecular weight compounds having more than 2 hydroxyl or amine groups serve as branching sites within the compounds of the invention.
  • the polyurethanes according to the invention may also contain copolymerized compounds of higher molecular weight with a hydroxyl group or an amine group.
  • Such compounds are, for example, polyetherols whose OH groups are all but one etherified. Examples of these are the polyalkylene glycol alkyl ethers of the formula
  • Suitable polyisocyanates preferably contain on average 2 to at most 4 NCO groups, with diisocyanates being particularly preferred.
  • isocyanates 1, 5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate (MDI), hydrogenated MDI (H12MDI), xylylene diisocyanate (XDI), tetramethylxylene diisocyanate (TMXDI), 4,4'-diphenyldimethylmethane diisocyanate, di- and Tetraalkyl diphenylmethane diisocyanate, 4,4-dibenzyl diisocyanate, 1, 3-phenylene diisocyanate, 1,4-phenylene diisocyanate, the isomers of tolylene diisocyanate (TDI), optionally in a mixture,
  • the polyurethanes according to the invention contain cycloaliphatic or aliphatic diisocyanate radicals, particularly preferably aliphatic diisocyanate radicals.
  • cycloaliphatic or aliphatic diisocyanate radicals particularly preferably aliphatic diisocyanate radicals.
  • condensed aliphatic diisocyanates are: 1, 4
  • condensed cycloaliphatic diisocyanates may be mentioned by way of example: isophorone diisocyanate (IPDI), 2-Isocyanatopropylcyclohexylisocyanat, 4-methyl-cyclohexane-1, 3-diisocyanate (H-TDI) and 1, 3-bis (isocyanatomethyl) cyclohexane.
  • diisocyanates such as 4,4'-methylene-bis (cyclohexylisocyanat) (alternatively also called dicyclohexylmethane-4,4'-diisocyanate) or 2,4'-methylenebis (Cyclohexyl) diisocyanate can be present as radicals in the polyurethanes according to the invention.
  • isocyanates having a functionality of 2 (2 NCO groups per molecule) are used.
  • isocyanates having a functionality greater than 2 are used. Then, polyurethanes having a branched structure on the isocyanate segment are obtained.
  • the components which are reactive toward the hydroxyl and amine groups are employed in an amount such that the groups reactive with the hydroxyl and amine groups are present in excess.
  • Such a surplus leads to the fact that the end groups of the formula (I) can be linked to the remaining compound by the reaction of a polyether of the formula (I) with the groups which are reactive towards -OH or -NH-reactive groups.
  • a greater amount of isocyanate groups than the amount of OH groups of the polyols and optionally chain extenders is used to prepare the compounds according to the invention. If, for example, exclusively diols and diisocyanates are used in addition to the end groups for the preparation of the compounds according to the invention, the diisocyanates are used in molar excess.
  • the ratio of NCO groups to - NCO groups of reactive groups in the preparation of the compounds of the invention in Range from 1, 2 to 1 to 2 to 1, preferably from 1, 4 to 1 to 1, 8 to 1, wherein for the calculation of the -NCO groups reactive groups of the polyethers of formula (I) are not taken into account.
  • Preferred polyether polyurethanes include polyether polyols and polyisocyanates in a condensed form.
  • An object of the invention are therefore polymers described above according to the invention, wherein the polymer is a polyether polyurethane and
  • the molar ratio of NCO groups of the polyisocyanate to OH groups of the polyether polyol before polymerization in the range of 1, 2 to 1 to 2 to 1, preferably in the range of 1.4 to 1 to 1, 8 to 1 lies.
  • polyether polyurethanes according to the invention in copolymerized form contain at least one polyether diol as polyol and at least one diisocyanate as polyisocyanate.
  • polyetherurethanes according to the invention contain, as polyol, at least one polyether diol and at least one polyisocyanate having at least three isocyanate groups (-NCO) in a condensed form.
  • polyether polyurethanes according to the invention are branched at least at the hydrophobic sections based on the at least trifunctional polyisocyanate.
  • polyether polyurethanes according to the invention comprise as polyol at least one polyether polyol having at least three hydroxyl groups and as polyisocyanate at least one diisocyanate.
  • Such polyether polyurethanes of the invention are branched at least at the hydrophilic sections based on the at least trifunctional polyether polyol.
  • polyether polyurethanes according to the invention comprise at least one polyether polyol having at least three hydroxyl groups and at least one polyisocyanate having at least three isocyanate groups in a condensed form.
  • polyether polyurethanes according to the invention have a hyperbranched or dendritic structure.
  • the preparation of hyperbranched polyurethanes is described, for example, in WO 97/02304 or DE 199 04 444.
  • a particularly preferred embodiment of the invention relates to low-branched or linear polyurethanes according to the invention, the polyisocyanate component and the polyol component used to prepare the polyurethanes of the invention having the following composition:
  • the polyisocyanate component comprises at least 80, preferably at least 90, more preferably at least 95 and especially at least 99 weight percent diisocyanates.
  • the polyol component comprises at least 80, preferably at least 90, more preferably at least 95 and in particular at least 99 wt .-% diols, wherein the diols are preferably selected from polyether diols.
  • R 1 independently of one another are C 4 -C 40 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 30 -aryl, C 7 -C 40 -aralkyl, C 7 -C 40 -alkylaryl or - (R 2 -O) n -R 3 ;
  • R 2 , R 4 independently of one another are C 2 -C 10 -alkylene, C 6 -C 10 -arylene, or C 7 -C 10 -arylalkylene;
  • R 3 H, Ci-C 40 alkyl, C 3 -C 0 cycloalkyl, C 6 -C 30 aryl, C 7 -C 40 aralkyl or C 7 -C 40 - alkylaryl;
  • n 1 to 200;
  • the end group can be linked to the remaining compound instead of via O also via NR 5 , with R 5 selected from H and C 1 -C 30 -alkyl.
  • R 1 is preferably C 1 -C 3 2-alkyl, Cio-C 3 2 -alkenyl, or - (R 2 -O) n -R 3 . More preferably R 1 is Cio-C 3 2-alkenyl or - (R 2 -O) n -R 3 . Very particular preference is given to Ri - (R 2 -O) n -R 3 . In a further preferred embodiment R 1 is - (R 2 -O) n -R 3 , where R 2 is C 2 -C 5 -alkylene and R 3 is C 2 -C 30 -alkyl or C 7 -C 4 -O- Aralkyl is.
  • R 2 and R 4 are independently of each other preferably C 2 -C 10 -alkylene, substituted or preferably unsubstituted, for example -CH 2 -CH 2 -, -CH (CH 3 ) -CH 2 -, -CH 2 -CH (CH 3 ) -, -CH (C 2 H 5 ) - CH 2 -, -CH 2 -CH (C 2 H 5 ) -, - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 6 -, - (CH 2 ) 8 -, - (CH 2 ) io, preferably -CH 2 - CH 2 -, -CH (CH 3 ) -CH 2 - or -CH 2 -CH (CH 3 ) -, more preferably -CH 2 -CH 2 -.
  • the alkylene radicals R 2 may be present individually or in mixtures of different alkylene radicals.
  • ethylene and propylene radicals may be mixed.
  • the various alkyl radicals may be present in random order or in block form.
  • R 3 is preferably H, Ci-C 2 8 alkyl, C7-C 4 o-aralkyl, or C7-C 4 o-alkylaryl. Particularly preferred R 3 is C6-C 2 8-alkyl, for example selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, ICO syl, henicosyl, Docosyl, tricosyl, tetracosyl, pentacosyl and / or hexacosyl, and very particularly preferably C 2 -C 2 6-alkyl, for example dodecyl, tridecyl, tetradecyl, pentadecyl, hexa
  • Tetradecyl, iso-hexadecyl, iso-octadecyl, and iso-eicosyl may also be used as well as residues of cycloalkanes or alkenes.
  • R 3 is Ce-C 2 o-alkyl and R 2 is ethylene.
  • R 2 is ethylene and R 3 is a C 3 alkyl, in particular iso-C 3 alkyl.
  • n is preferably 2 to 100, particularly preferably 4 to 50 and very particularly preferably 8 to 40.
  • m is preferably 2 to 5 and more preferably 3 to 4.
  • p is preferably 0 to 50, more preferably 0 to 20.
  • End groups of the general formula (I) are preferably prepared by reaction of the corresponding polyether monoalcohol of the general formula (Ia)
  • Polyether dendrons of the formula (Ia) and their preparation are generally known, for example from EP 09165576.1.
  • at least one compound of the general formula R 1 -OH with glycerol or preferably a reactive glycerol derivative to, in particular with epichlorohydrin is selected.
  • a molar ratio of the compound of general formula R 1 -OH to reactive derivative of glycerol, in particular epichlorohydrin, such as 2: 1 is selected.
  • the preparation can be carried out for example at temperatures in the range of 20 to 200 ° C, preferably at 80 to 130 ° C.
  • the preparation can be carried out in the presence of a catalyst. Suitable catalysts are, for example, inorganic and organic bases.
  • the base serves not only as a catalyst but also to neutralize the resulting HCl.
  • Suitable inorganic bases are, for example, alkali metal carbonates and in particular alkali metal hydroxides such as NaOH and KOH.
  • Suitable organic bases are, for example, tertiary amines, in particular triethylamine and
  • DABCO diazabicyclooctane
  • the preparation can be carried out in a solvent.
  • suitable solvents are ethers, in particular 1,4-dioxane, diisopropyl ether, tetrahydrofuran (“THF”) and di-n-butyl ether.
  • butyl acetate butyl acetate
  • DMSO ⁇ , ⁇ -dimethylformamide
  • N-methylpyrrolidone aromatic solvents such as toluene.
  • water-removing agent for example molecular sieve, sodium sulfate, magnesium sulfate, or the water formed can be removed by azeotropic distillation.
  • the reaction is carried out over a period of 15 minutes to 48 hours, preferably 1 to 24 hours, more preferably 3 to 15 hours.
  • the reaction is carried out in stages, in as many stages as it corresponds to the desired m.
  • reactive derivative of glycerol in particular epichlorohydrin
  • the stepwise reaction can be carried out, for example, by first reacting a certain amount of compound of the general formula R 1 -OH with half the number of moles of glycerol or preferably with a reactive derivative of glycerol, in particular with epichlorohydrin. Thereafter, an amount of glycerol or reactive derivative of glycerol corresponding to one quarter of the number of moles of compound of the general formula R 1 - OH is added and reacted.
  • the end groups of formula (I) are contaminated with products of incomplete reaction. Due to incomplete conversion, the following structural units can then be formed, for example:
  • the end groups of the formula (I) and the partially reacted end groups are linked to the remaining compound via an oxygen atom.
  • At least one end group of the general formula (I) is preferably bonded to the remaining compound via a structural unit selected from esters, amides, imides, urethanes, ureas, amines, ethers.
  • At least one end group of the general formula (I) is bonded to the remaining compound via a structural unit selected from urethanes and ureas.
  • Another object of the present invention is a process for the preparation of the compound according to the invention with at least the following steps:
  • R 1 independently of one another are C 4 -C 40 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 30 -aryl, C 7 -C 40 -aralkyl,
  • R 2 R 4 independently of one another C2-Cio-alkylene, C6-Cio-arylene, or C 7 -Cio-aralkylene;
  • R 3 H, Ci-C 40 alkyl, C 3 -C 0 cycloalkyl, C 6 -C 30 aryl, C 7 -C 40 aralkyl or C 7 -C 40 - alkylaryl;
  • n 1 to 200;
  • solvents may also be added.
  • water is added to the resulting reaction mixture after completion of the reaction, so that an aqueous dispersion is preferably obtained.
  • "After completion of the reaction” means the time at which the content of isocyanate groups, based on the reaction mixture after addition of all reactive substances, less than 5, preferably less than 1 and more preferably less than 0.1 wt .-% is.
  • at least one polyol is a polyetherol, preferably a polyether diol.
  • a diisocyanate is used in the process according to the invention as at least one polyisocyanate.
  • the starting materials used are also compounds having more than two hydroxyl groups per molecule and / or compounds having more than two isocyanate groups per molecule.
  • solvent refers to liquid substances or mixtures of substances under normal conditions in which at least one of the reactive components is at least 10% by weight, based on the resulting solution, soluble to the human eye, clearly and without phase separation.
  • Reactive components are understood as meaning all substances which are chemically incorporated into the compounds according to the invention in the preparation of the compounds according to the invention.
  • Reactive components of the process according to the invention are, for example, polyols, polyisocyanates, compounds having a hydroxyl group and compounds having an isocyanate group.
  • the proportion of the solvents based on the total amount of all present during the process according to the invention substances is at least 30 wt .-%, preferably at least 50 wt .-%, in particular at least
  • the proportion of the solvents based on the total amount of all present during the process according to the invention substances is at most 10 wt .-%, preferably at most 5 wt .-%, more preferably at most 1 wt .-% and in particular at most 0 , 1% by weight.
  • An embodiment of the invention is thus a substantially solvent-free process, also referred to as melt process.
  • anhydrous polyol is used to prepare the compounds according to the invention.
  • the removal of the water from the polyol can be carried out in a step A by azeotropic distillation, drying under vacuum or other methods known in the art. For example, water may be removed by azeotropic distillation until the water content is about 300 ppm prior to addition of the hydroxyl-reactive substances, preferably polyisocyanates.
  • preparation of the actual reaction may consist of either vacuuming the polyol to remove the water sufficiently (preferably to a water content of about 300 ppm or lower) and then adding a solvent, or the polyol to one Solvents such as xylene, toluene or acetone is mixed and the water is removed by azeotropic distillation, for example up to a water content of about 300 ppm, but the solvent is not completely removed, but the solution of polyol in the remaining solvent for reaction in Solution is used.
  • Solvents such as xylene, toluene or acetone
  • a one-pot reaction is understood to mean a preparation process which comprises mixing essentially all the required reactive substances and solvents in the reaction space (for example, round-bottom flask, three-necked flask, conical flask, reaction vessel, kettle cascade, flow tube) before reacting (usually with stirring / mixing and heating or cooling).
  • individual components are added only during the reaction.
  • At least 90% by weight, more preferably at least 95% by weight, of all reactive substances are preferably present in the reaction space before the beginning of the reaction.
  • Suitable catalysts are in principle all catalysts customarily used in polyurethane chemistry.
  • the catalysts described in WO 2009/135857, p.14-16 are preferably used.
  • the catalyst is particularly preferably selected from zinc 2-ethylhexanoate (also called zinc octanoate), zinc n-octanoate, zinc n-decanoate, zinc neodecanoate, zinc ricinoleate and zinc stearate.
  • zinc neodecanoate is used.
  • the compounds according to the invention are preferably used in cosmetic preparations.
  • An object of the invention are thus cosmetic preparations containing the compounds of the invention.
  • One embodiment of the invention are water-containing cosmetic preparations containing the compounds according to the invention.
  • the preparations according to the invention can be in the form of aqueous or aqueous-alcoholic solutions, O / W (preferred) and W / O emulsions, W / O / W (preferred) and O / W / O emulsions, hydrodispersion formulations, solids-stabilized formulations, stick formulations , PIT formulations, in the form of creams, foams, sprays (pump spray or aerosol), gels, gel sprays, lotions, oils, oil gels or mousses and are accordingly formulated with conventional other excipients.
  • the preparations according to the invention are preferably in the form of a gel, foam, mousse, spray, ointment, cream, emulsion, suspension, lotion, milk or paste.
  • the invention preferably relates to cosmetic preparations which are selected from gels, gel creams, milks, hydroformulations, stick formulations, cosmetic oils and oil gels, mascara, self-tanner, face care, personal care products, after-sun preparations.
  • cosmetic preparations is also understood to mean preparations for oral care.
  • Further cosmetic preparations according to the invention are skin-cosmetic preparations, in particular those for the care of the skin. These are in particular as W / O or preferably O / W skin creams, day and night creams, eye creams, face creams, anti-wrinkle creams, facial expressions creams, moisturizing creams, bleaching creams, vitamin creams, skin lotions, body lotions and moisturizing lotions.
  • compositions according to the invention are face masks, cosmetic lotions and preparations for use in decorative cosmetics, for example covering pens, theatrical paints, mascara and eye shadows, lipsticks, kohl pencils, eyeliner, mascots, primers, rouges, powders and eyebrow pencils.
  • washing, showering and bathing preparations are soaps of liquid to gelatinous consistency, transparent soaps, luxury soaps, de-icing soaps, cream soaps, baby soaps. skin cleansing soaps, abrasive soaps and syndets, pasteurized soaps, soft soaps and washing pastes, liquid washing, showering and bathing preparations such as washing lotions, shower baths and gels, bubble baths, oil baths, shower oils and scrub preparations, shaving foams, lotions and creams.
  • Cosmetic preparations containing special polyurethanes are described, for example, in WO 2009/135857.
  • the compounds of the present invention are also generally suitable for use in the formulations described in WO 2009/135857.
  • the disclosure of WO 2009/135857 is hereby incorporated by reference.
  • the polyurethanes used in the preparations of WO 2009/135857 are replaced by the compounds according to the invention.
  • the compounds according to the invention are therefore preferably used in the preparations of WO 2009/135857 instead of the polyurethanes used there.
  • Suitable ingredients for the preparations according to the invention are described in WO 2009/135857, p.24 to p.35, to which reference is made in its entirety.
  • Cosmetic UV light stabilizers containing the compounds according to the invention.
  • Cosmetic light stabilizers in the context of this invention are understood to mean cosmetic preparations which comprise at least one, preferably several, UV filter substances.
  • UV light stabilizers corresponding to UV light stabilizer formulations according to the invention are described in WO 2009/135857, p.35 to p.42, to which reference is made in its entirety.
  • An object of the present invention are aqueous preparations which, in addition to the compounds according to the invention, furthermore comprise at least one salt or surfactant or both.
  • Another embodiment of the invention are shampoos and cosmetic cleansing compositions containing the compounds of the invention.
  • a further embodiment of the invention are the deodorants or antiperspirants according to the invention, in particular deodorant lotions and deodorant or antiperspirant sticks, based on oil-in-water dispersion or emulsion for the application of active substances, in particular of water-soluble active ingredients the skin.
  • a further embodiment of the invention are the hair colorants containing the compounds according to the invention.
  • hair colorants containing the compounds according to the invention are described analogously in WO 2009/135857, p.59 to p65, to which reference is made in its entirety.
  • a further embodiment of the invention are hair-care compositions containing the compounds according to the invention, in particular hair conditioning agents.
  • a further embodiment of the invention are the acidic preparations containing the compounds according to the invention.
  • compositions comprise active substances which develop their desired action, especially at acidic pH values. These include, for example, preparations comprising alpha-hydroxycarboxylic acids (AHA) and beta-hydroxycarboxylic acids (BHA), since these are little to no effect in the neutralized state.
  • AHA alpha-hydroxycarboxylic acids
  • BHA beta-hydroxycarboxylic acids
  • the acidic preparations corresponding to the acidic preparations containing the compounds according to the invention are described analogously in WO 2009/135857, p67 to p69, to which reference is made in its entirety.
  • such preparations contain self-tanning substances in a concentration of 0.1 to 10 wt .-% and particularly preferably from 0.5 to 6 wt .-%, each based on the total weight of the preparation.
  • these preparations contain as self-tanning substance 1, 3-dihydroxyacetone. More preferably, these compositions contain organic and / or inorganic sunscreen filters. The preparations may also contain inorganic and / or organic and / or modified inorganic pigments.
  • a further embodiment of the invention are the compositions according to the invention containing preparations for oral and dental care and cleaning.
  • compositions containing the compounds according to the invention for oral and dental care and cleaning preparations are described analogously in
  • Preparations corresponding to preparations containing the compounds according to the invention for hair removal are described analogously in WO 2009/135857, p. 70 to p. 71, to which reference is made in their entirety.
  • a further embodiment of the invention are the preparations according to the invention for permanent hair shaping.
  • An object [Bijder present invention is the use of polymers according to the invention to increase the compatibility with polar solvents such as ethanol, propylene glycol or glycerol.
  • Another object of the present invention is the use of polymers according to the invention for increasing the water-binding capacity in the preparation and after application to the skin (moisturizer).
  • polymers according to the invention for improving the dispersibility of particles in the preparation.
  • the preparation of compound A.1 was carried out in 1, 4-dioxane dried according to standard methods.
  • the molecular weight of A.1 was determined by gel permeation chromatography (GPC) in DMAC ( ⁇ , ⁇ -dimethylacetamide) as the solvent, PMMA was used as standard.
  • the dynamic viscosities of the compounds according to the invention in aqueous dispersion were measured in the form of a 10% by weight dispersion at 23 ° C.
  • the dynamic viscosity was determined at shear rates of 100 1 / s and 350 1 / s. These two values allow one to make a statement as to whether the compounds of the invention in aqueous Dispersion pseudoplastic or Newtonian thickening behavior show.
  • R 2 -CH 2 -CH 2 -;
  • the mixture was heated to 100 ° C and then 6.8 g (73.5 mmol) of epichlorohydrin, dissolved in 25 ml of dioxane, over a period of 30 minutes dropwise. The mixture was then stirred for 2 hours, then a further 3.4 g (36.8 mmol) of epichlorohydrin dissolved in 25 ml of dioxane was added dropwise over a period of 30 minutes. The mixture was stirred again for 2 hours, then another 1.7 g (18.4 mmol) of epichlorohydrin dissolved in 25 ml of dioxane were added dropwise over a period of 15 minutes.
  • the solvent xylene was subsequently largely removed by vacuum distillation at elevated temperature (60 ° C.) (residual content ⁇ 100 ppm) and the residue was dissolved in 515.8 g of water. After cooling to room temperature (25 ° C) of the aqueous solution was finally added 6.45 g of the preservative Euxyl K701 ® and 70 mg of the stabilizer 4-hydroxy-TEM PO.
  • the viscosity of a 10% strength by weight aqueous solution of the polyether polyurethane A.2 was 20,500 mPa * s (shear rate 100 l / s) or 10,000 mPa * s (shear rate 350 l / s).
  • the solvent xylene was subsequently largely removed by vacuum distillation at elevated temperature (60 ° C) (residual content ⁇ 100 ppm) and the residue dissolved in 666.7 g of water. After cooling to room temperature (25 ° C) of the aqueous solution was finally added 8.34 g of the preservative Euxyl K701 ® and 80 mg of the stabilizer 4-hydroxy-TEMPO.
  • the viscosity of a 10% strength by weight aqueous solution of the polyether polyurethane A.3 was 1750 mPa * s (shear rate 100 l / s) or 1550 mPa * s (shear rate 350 l / s).
  • the cosmetic formulations FA.2 and FA.3 were prepared by adding the oil phase A to the water phase B and then adding the preservative (phase C) to the resulting O / W emulsion.
  • Phase B homogenized on a three-roll mill. Stir phase B into phase A.
  • Dissolve phase D stir into the combined phases A + B + C and homogenize.
  • phase B Combine phase B and A at room temperature with stirring and stir homogeneously, then add phase C with stirring and stir smoothly hair mousse
  • Phase C propellant A46 (propane / isobutane)
  • alpha hydroxy acids lactic acid, citric acid, malic acid, glycolic acid
  • beta hydroxy acid salicylic acid
  • the formulation is produced without inert gas.
  • the filling must be in oxygen-impermeable packaging, e.g. Aluminum tubes, done.
  • cationic polymer such as Polyquaternium-7, PQ-10, PQ-16, PQ-39, PQ-44, PQ-46,
  • phase A Adjust pH to 6-7. Add phase B and warm to 50 ° C. Allow to cool to room temperature with stirring.
  • the compounds according to the invention can also be used in hairstyling preparations, in particular hair foams (aerosol foams with propellant gas and pump foams without propellant gas), hair sprays (pump sprays without propellant gas) and hair gels.
  • Propellants are the commonly used propellants. Preference is given to mixtures of propane / butane, pentane, dimethyl ether, 1,1-difluoroethane (HFC-152a), carbon dioxide, nitrogen or compressed air.
  • HFC-152a 1,1-difluoroethane
  • solidifying polymer or combinations of e.g. PVP, PVP / VA copolymer, Polyquaternium-4, PQ-1 1, PQ-16, PQ-46, PQ-44, PQ-68, VP / methacrylamide / vinyl imidazole copolymer, etc.
  • 1 1.00 g of solidifying polymer or combinations of e.g. PVP, PVP / VA copolymer, Polyquaternium-4, PQ-1 1, PQ-16, PQ-46, PQ-44, PQ-68, VP / methacrylamide / vinyl imidazole copolymer, etc.
  • a preparation suitable for styling sprays according to the invention can be composed, for example, as follows:
  • Iron oxide / Al Powder / silica eg Sicopearl ® Fantastico Gold from BASF or other effect pigments
  • silica 1.80 g of silica 1.00 g of sodium lauryl sulfate
  • Phenonip Phenoxyethanol methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des épaississants associatifs à base de composés qui comportent au moins un dendron de polyéther rendu hydrophobe en tant que groupe terminal.
PCT/EP2011/064607 2010-09-01 2011-08-25 Épaississants associatifs pour préparations aqueuses WO2012028527A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CN2011800418498A CN103124754A (zh) 2010-09-01 2011-08-25 用于含水制剂的缔合性增稠剂
BR112013004660A BR112013004660A2 (pt) 2010-09-01 2011-08-25 espessante associativo para soluções aquosas
EP11754335.5A EP2611845A1 (fr) 2010-09-01 2011-08-25 Épaississants associatifs pour préparations aqueuses
JP2013526415A JP2013537921A (ja) 2010-09-01 2011-08-25 水性組成物用会合性増粘剤
AU2011298459A AU2011298459A1 (en) 2010-09-01 2011-08-25 Associative thickener for aqueous preparations
KR1020137005311A KR20140001825A (ko) 2010-09-01 2011-08-25 수성 제제를 위한 회합 증점제
MX2013002262A MX2013002262A (es) 2010-09-01 2011-08-25 Espesante asociativo para preparaciones acuosas.
RU2013113873/04A RU2013113873A (ru) 2010-09-01 2011-08-25 Ассоциативный загуститель для водных композиций
CA2810099A CA2810099A1 (fr) 2010-09-01 2011-08-25 Epaississants associatifs pour preparations aqueuses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10174804.4 2010-09-01
EP10174804 2010-09-01

Publications (1)

Publication Number Publication Date
WO2012028527A1 true WO2012028527A1 (fr) 2012-03-08

Family

ID=44582980

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/064607 WO2012028527A1 (fr) 2010-09-01 2011-08-25 Épaississants associatifs pour préparations aqueuses

Country Status (10)

Country Link
EP (1) EP2611845A1 (fr)
JP (1) JP2013537921A (fr)
KR (1) KR20140001825A (fr)
CN (1) CN103124754A (fr)
AU (1) AU2011298459A1 (fr)
BR (1) BR112013004660A2 (fr)
CA (1) CA2810099A1 (fr)
MX (1) MX2013002262A (fr)
RU (1) RU2013113873A (fr)
WO (1) WO2012028527A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014098267A1 (fr) * 2012-12-21 2014-06-26 L'oreal Composition cosmétique
WO2014098268A1 (fr) * 2012-12-21 2014-06-26 L'oreal Composition cosmétique
US8987357B2 (en) 2011-05-27 2015-03-24 Basf Se Thermoplastic molding composition
EP2876128A1 (fr) 2013-11-25 2015-05-27 Basf Se Procédé de rinçage de polyéthers hautement ramifiés solubles dans l'eau
US9334398B2 (en) 2012-02-14 2016-05-10 Basf Se Aqueous polymer dispersion obtainable by free-radically initiated emulsion polymerization in the presence of lignosulfonate
EP3929232A1 (fr) * 2020-06-24 2021-12-29 Evonik Operations GmbH Utilisation de formulations de tensioactifs contenant des alcools à longue chaîne dans des dispersions aqueuses de polyuréthane

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109689019B (zh) * 2016-09-16 2022-02-22 株式会社资生堂 组合物和产品
JP6293345B1 (ja) * 2017-10-27 2018-03-14 株式会社伊勢半 睫毛化粧料
JP6574499B2 (ja) * 2018-02-05 2019-09-11 株式会社伊勢半 セルフタンニング化粧料

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4079028A (en) 1975-10-03 1978-03-14 Rohm And Haas Company Polyurethane thickeners in latex compositions
EP0725097A1 (fr) 1995-02-02 1996-08-07 Bayer Ag Polyuréthanes comme agents épaississants pour systèmes aqueux
WO1997002304A1 (fr) 1995-07-01 1997-01-23 Basf Aktiengesellschaft Polyurethanes hautement fonctionalises
EP0761780A2 (fr) 1995-09-06 1997-03-12 Asahi Denka Kogyo Kabushiki Kaisha Composé régulateur de la viscosité
US6002049A (en) * 1990-11-08 1999-12-14 Henkel Corporation Polymeric thickeners for aqueous compositions
EP1013264A1 (fr) 1998-12-17 2000-06-28 Shiseido Company Limited Composition cosmétique
DE19904444A1 (de) 1999-02-04 2000-08-10 Basf Ag Dendrimere und hochverzweigte Polyurethane
WO2002088212A1 (fr) 2001-04-12 2002-11-07 Cognis Deutschland Gmbh & Co. Kg Preparations cosmetiques
DE10321147A1 (de) 2003-05-12 2004-12-02 Beiersdorf Ag Stabilisierung von Selbstbräunungsprodukten durch Schichtsilikate
WO2006002813A2 (fr) 2004-07-01 2006-01-12 Cognis Ip Management Gmbh Agents epaississants a base de polyurethane
WO2009135857A2 (fr) 2008-05-06 2009-11-12 Basf Se Polyuréthanes comme agents modificateurs de rhéologie pour préparations cosmétiques
WO2009135856A1 (fr) 2008-05-06 2009-11-12 Basf Se Épaississant à base de polyuréthanne
DE102008030992A1 (de) 2008-06-30 2010-01-07 Freie Universität Berlin Linear-dendritische Polyglycerolverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5959990A (ja) * 1982-09-28 1984-04-05 本州製紙株式会社 古紙の脱墨方法
JP2692201B2 (ja) * 1988-11-29 1997-12-17 日本油脂株式会社 無機粉末の水中分散安定剤
JP2692202B2 (ja) * 1988-11-29 1997-12-17 日本油脂株式会社 無機粉末の油中分散安定剤
JPH03247670A (ja) * 1990-02-23 1991-11-05 Mitsubishi Gas Chem Co Inc 熱可塑性樹脂組成物
EP0556338A1 (fr) * 1990-11-08 1993-08-25 Henkel Corporation Epaississant polymere pour compositions aqueuses
JP2006124210A (ja) * 2004-10-27 2006-05-18 Sanyo Chem Ind Ltd セメント組成物用添加剤
EP2454296B1 (fr) * 2009-07-15 2015-11-11 Basf Se Copolymères, leur utilisation comme épaississants et procédé pour leur production
EP2611847B1 (fr) * 2010-09-01 2018-11-07 Basf Se Amphiphile servant à solubiliser des substances actives difficilement solubles

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4079028B1 (fr) 1975-10-03 1990-08-21 Rohm & Haas
US4079028A (en) 1975-10-03 1978-03-14 Rohm And Haas Company Polyurethane thickeners in latex compositions
US6002049A (en) * 1990-11-08 1999-12-14 Henkel Corporation Polymeric thickeners for aqueous compositions
EP0725097A1 (fr) 1995-02-02 1996-08-07 Bayer Ag Polyuréthanes comme agents épaississants pour systèmes aqueux
WO1997002304A1 (fr) 1995-07-01 1997-01-23 Basf Aktiengesellschaft Polyurethanes hautement fonctionalises
EP1111014A1 (fr) 1995-09-06 2001-06-27 Asahi Denka Kogyo Kabushiki Kaisha Agent épaississant
EP0761780A2 (fr) 1995-09-06 1997-03-12 Asahi Denka Kogyo Kabushiki Kaisha Composé régulateur de la viscosité
EP1013264A1 (fr) 1998-12-17 2000-06-28 Shiseido Company Limited Composition cosmétique
EP1584331A1 (fr) 1998-12-17 2005-10-12 Shiseido Co., Ltd. Composition cosmétique comprenant un polyéther polyuréthanne modifié hydrophobiquement et un alcool monohydrique
DE19904444A1 (de) 1999-02-04 2000-08-10 Basf Ag Dendrimere und hochverzweigte Polyurethane
WO2002088212A1 (fr) 2001-04-12 2002-11-07 Cognis Deutschland Gmbh & Co. Kg Preparations cosmetiques
DE10321147A1 (de) 2003-05-12 2004-12-02 Beiersdorf Ag Stabilisierung von Selbstbräunungsprodukten durch Schichtsilikate
WO2006002813A2 (fr) 2004-07-01 2006-01-12 Cognis Ip Management Gmbh Agents epaississants a base de polyurethane
WO2009135857A2 (fr) 2008-05-06 2009-11-12 Basf Se Polyuréthanes comme agents modificateurs de rhéologie pour préparations cosmétiques
WO2009135856A1 (fr) 2008-05-06 2009-11-12 Basf Se Épaississant à base de polyuréthanne
DE102008030992A1 (de) 2008-06-30 2010-01-07 Freie Universität Berlin Linear-dendritische Polyglycerolverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8987357B2 (en) 2011-05-27 2015-03-24 Basf Se Thermoplastic molding composition
US9334398B2 (en) 2012-02-14 2016-05-10 Basf Se Aqueous polymer dispersion obtainable by free-radically initiated emulsion polymerization in the presence of lignosulfonate
WO2014098267A1 (fr) * 2012-12-21 2014-06-26 L'oreal Composition cosmétique
WO2014098268A1 (fr) * 2012-12-21 2014-06-26 L'oreal Composition cosmétique
EP2876128A1 (fr) 2013-11-25 2015-05-27 Basf Se Procédé de rinçage de polyéthers hautement ramifiés solubles dans l'eau
EP3929232A1 (fr) * 2020-06-24 2021-12-29 Evonik Operations GmbH Utilisation de formulations de tensioactifs contenant des alcools à longue chaîne dans des dispersions aqueuses de polyuréthane

Also Published As

Publication number Publication date
JP2013537921A (ja) 2013-10-07
KR20140001825A (ko) 2014-01-07
BR112013004660A2 (pt) 2016-08-02
MX2013002262A (es) 2013-05-22
EP2611845A1 (fr) 2013-07-10
RU2013113873A (ru) 2014-10-10
CN103124754A (zh) 2013-05-29
CA2810099A1 (fr) 2012-03-08
AU2011298459A1 (en) 2013-03-14

Similar Documents

Publication Publication Date Title
EP2630176B1 (fr) Épaississants polyuréthanes
US20120082629A1 (en) Associative Thickeners For Aqueous Preparations
EP2611845A1 (fr) Épaississants associatifs pour préparations aqueuses
US8871817B2 (en) Polyurethane thickeners
EP2282715B1 (fr) Polyuréthanes comme agents modificateurs de rhéologie pour préparations cosmétiques
EP1773906B1 (fr) Polyurethanes reticules contenant un polytetrahydrofurane
US9175125B2 (en) Polyurethane thickeners
WO2004055088A1 (fr) Polyuréthanne contenant des groupes allyle
WO2012098176A1 (fr) Épaississants dendritiques polyéther-polyuréthane
EP2630175B1 (fr) Épaississants polyuréthanes
WO2003068834A1 (fr) Copolymeres greffes pour preparations cosmetiques
WO2004022020A1 (fr) Utilisation de n-hexylester d'acide 2-(4-diethylamino-2-hydroxybenzoyle)-benzoique dans des compositions cosmetiques ou dermatologiques, dans le traitement capillaire
RU2574665C2 (ru) Полиуретановый загуститель
WO2011029738A1 (fr) Composition comprenant un polymère basé sur des polyols particuliers, et méthode de traitement cosmétique

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201180041849.8

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11754335

Country of ref document: EP

Kind code of ref document: A1

REEP Request for entry into the european phase

Ref document number: 2011754335

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2011754335

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: MX/A/2013/002262

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 20137005311

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2013526415

Country of ref document: JP

Kind code of ref document: A

Ref document number: 2810099

Country of ref document: CA

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2011298459

Country of ref document: AU

Date of ref document: 20110825

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2013113873

Country of ref document: RU

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112013004660

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112013004660

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20130227