EP2195408A2 - Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage - Google Patents

Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage

Info

Publication number
EP2195408A2
EP2195408A2 EP08804501A EP08804501A EP2195408A2 EP 2195408 A2 EP2195408 A2 EP 2195408A2 EP 08804501 A EP08804501 A EP 08804501A EP 08804501 A EP08804501 A EP 08804501A EP 2195408 A2 EP2195408 A2 EP 2195408A2
Authority
EP
European Patent Office
Prior art keywords
water
cleaning agent
mca
formula
surfactant
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Withdrawn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
EP08804501A
Other languages
German (de)
English (en)
Inventor
Dirk Schumann
Rainer Surkow
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.)
Bubbles and Beyond GmbH
Original Assignee
Bubbles and Beyond GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39133799&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP2195408(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bubbles and Beyond GmbH filed Critical Bubbles and Beyond GmbH
Priority to EP10004122.7A priority Critical patent/EP2223995B2/fr
Priority to EP08804501A priority patent/EP2195408A2/fr
Publication of EP2195408A2 publication Critical patent/EP2195408A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0017—Multi-phase liquid compositions
    • C11D17/0021—Aqueous microemulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/04—Nail coating removers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • C09D9/04—Chemical paint or ink removers with surface-active agents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2096—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/24—Organic compounds containing halogen
    • C11D3/245—Organic compounds containing halogen containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3445—Organic compounds containing sulfur containing sulfino groups, e.g. dimethyl sulfoxide
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/362—Phosphates or phosphites
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
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    • A—HUMAN NECESSITIES
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    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/24—Mineral surfaces, e.g. stones, frescoes, plasters, walls or concretes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3427—Organic compounds containing sulfur containing thiol, mercapto or sulfide groups, e.g. thioethers or mercaptales
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3472—Organic compounds containing sulfur additionally containing -COOH groups or derivatives thereof

Definitions

  • the present invention describes new detergents, a process for their preparation and a process for cleaning various surfaces, especially when they have been desirably or undesirably treated with soils, varnishes and paints, paint sprays, crayons or other colored surface coatings.
  • the cleaning agent according to the invention is used in particular for the removal of graffiti from smooth and / or porous substrates, for paint stripping of metal, wood or glass surfaces, for removing dirt, for removing cosmetics, for hair discoloration and for removing nail polish.
  • the cleaning effect of the compositions according to the invention consists in a fragmentation of the dirt or paint layers and their detachment from the substrate, smearing being largely avoided. This is made possible by the composition according to the invention of specially extended microemulsions.
  • the sprayed or painted surfaces are usually made of concrete, plaster, brick and clinker, but also of fine ceramics and natural stones, such as marble or sandstone.
  • fine ceramics and natural stones such as marble or sandstone.
  • the colors penetrate into the pores and wall joints, so that removal is difficult.
  • Easier to clean are smooth surfaces, such as painted or unpainted metals, plastics or glass.
  • the color pigments In addition to the substrate, the color pigments also decide on the effort of color removal. On the one hand, dark shades already leave a striking visual color shade on bright walls, on the other hand finer pigment particles are more easily introduced into pores and then remain therein. Color shadows are sometimes also produced by pigments with insufficient "authenticity.” Here, the pigments are not completely insoluble, so that pigment molecules migrate, for example, into a painted substrate or through a new coating and lead, inter alia, to so-called "bleeding through”.
  • the finely divided pigments include, in particular, the blacks (black) and phthalocyanines (green to blue) as well as some other organic pigments. With simply constructed organic pigments, those which tend to bleed through are also frequently found.
  • the white, yellow and red pigments on a mineral basis titanium dioxide, iron oxides, etc.
  • ultramarine and metallic pigments aluminum, bronzes
  • the binders used in the graffiti paints may be alkyd resins of various construction (e.g., polyester and fatty acid type and content, respectively), resins, modified or fully synthetic rubbers, cellulose esters, aldehyde condensates, or many other polymers.
  • alkyd resins of various construction (e.g., polyester and fatty acid type and content, respectively), resins, modified or fully synthetic rubbers, cellulose esters, aldehyde condensates, or many other polymers.
  • solvent-free, water-miscible spray paints it is often acrylic or polyvinyl acetate dispersions, sometimes also alkaline acrylic resins.
  • Graffiti removal is a special case of paint removal and pickling.
  • the task of paint removal while protecting the substrate is the same in both cases.
  • paint removal or pickling is less difficult, i.
  • cross-linked coating systems or coalesced high-polymer particles often have to be removed from emulsion paints, which are distinguished by their insolubility in solvents and their particularly good adhesion to the substrate.
  • lacquer not only relates to the detachment of dried lacquer coats, but also to the removal of fresh lacquer formulations, such as occur in wide applications, from the painting trade to the printing ink industry.
  • a special area of paint removal is the removal of nail polish.
  • a degreasing and leaching of the nails and the surrounding skin This manifests itself in the form of a whitening of nails and skin to brittle and dull nails in the long-term use of nail polish remover.
  • various proposals have already been made to avoid or even prevent these effects.
  • the degreasing and removal of important detergency builders from the nail is by the solvents, acetone, ethyl acetate, butyl acetate and the like have been and still are used in nail polish removers.
  • liquid or gel graffiti removers are usually used in the prior art.
  • the advantage of the Graffitientferner is the fast possibility of a job and the then beginning simultaneous effect on the detachment of the paint on larger surfaces, while with the mechanical only locally the color can be replaced.
  • the previous graffiti removers contain individual solvents or solvent mixtures which have the task of physically dissolving the binders of the graffiti paint.
  • the solvents are emulsified in water. The often dilute solvents or emulsions are usually thickened against draining on vertical surfaces by additives.
  • esters such as shorter and / or longer fatty acid esters, such as methyl oleate or fatty acid mixtures such as rapeseed oil fatty acid methyl ester ("biodiesel"), and various dicarboxylic acid esters, for example so-called dibasic esters (DBE esters)
  • DBE esters dibasic esters
  • EP 1772 496 A1 uses such methyl esters, as well as cyclohexanone, partly in (micro-) emulsion for dissolving the graffiti paints, but sometimes also acid esters are used, and the use of glycol derivatives, such as propylene carbonate, 1-methoxy-2-propanol or 2-methoxy, is also widespread. 1 - methylethyl acetate.
  • ethyl 3-ethoxypropionate described in the published patent application DE 10 2004 015 092 A1.
  • ethyl-3-ethoxypropionate has also been used many years previously in DE 691 28 887 T2 (EP 0 551 378 B1) for activating the strongly polar, aprotic solvents 1-methyl-2-pyrrolidone (NMP) and gamma-butyrolactone.
  • NMP 1-methyl-2-pyrrolidone
  • gamma-butyrolactone Especially the 1-methyl-2-pyrrolidone is a well-known and excellent paint solvent, which is used either in pure form or in mixtures with other solvents in many paint strippers and graffiti removers.
  • DE 695 21 333 T1 describes the use of 1-methyl-2-pyrrolidone, but also other pyrrolidones in amounts of 1 to 60 wt .-% in the formulation. Also, the gamma-butyrolactone structurally related tetrahydrofuran is used in Graffitientfernern.
  • 1-methyl-2-pyrrolidone is described in the published patent application DE 10 2004 012 751 A1, the 1-ethyl-2-pyrrolidone, which was also already part of DE 695 21 333 T1.
  • As structurally very similar to the pyrrolidones and the N-methylcaprolactam can be regarded from published patent application DE 102004015182 A1.
  • Short-chain solvent molecules often penetrate quickly into the binders of graffiti dyes, but in most cases they also evaporate quickly. Long-chain solvent molecules often require considerably more time for this process (for example, between about 20 minutes to 2 hours) and lead to a swelling of the coatings, so that they can then be mechanically rubbed off from the substrate more easily.
  • a disadvantage of individual solvents and even solvent mixtures is that not all binder types are solved equally well due to the complexity of the dissolution process, which is still not fully understood in particular with regard to the dissolution of paints or polymers can. This is noticeable when trying to solve different graffiti colors with the same remover system. From a wide range of different aerosol colors, it is always possible to replace some of them unsatisfactorily from the substrate.
  • a graffiti remover Since graffiti paints that can be removed do not recognize the pigment-binder composition at the point of damage, a graffiti remover must have the widest possible range of solubility. As noted above This can not fully achieve solvent mixtures. So it must be found a system, which can replace a large number of different binders from the substrate. The system should use the graffiti colors in a short time, e.g. B. within 10 minutes, a maximum of up to half an hour dissolve and remove from the ground as possible without color shade.
  • the graffiti remover should contain no toxic or long-term health or environmental problematic substances, namely no organic halogen compounds (such as dichloromethane), no gamma-butyrolactone and possibly also no N-alkyl-pyrrolidone, but also no strong acids or bases.
  • organic halogen compounds such as dichloromethane
  • gamma-butyrolactone no gamma-butyrolactone and possibly also no N-alkyl-pyrrolidone, but also no strong acids or bases.
  • strippers should not contain any toxic or long-term health or environmental problematic substances, namely no organic halogen compounds such as dichloromethane, no gamma-butyrolactone and, if possible, no N-alkylpyrrolidones. Likewise strong acids or bases should be avoided. The broad applicability and the fast action are still considered to be advantageous in the case of dichloromethane-containing strippers. However, dichloromethane-free agents often require significantly longer exposure times, sometimes up to more than 24 hours. Although this achieves a different greater depth effect, such long periods are unacceptable. In addition, the problem of smudging remains due to the use of solvents or their mixtures.
  • a suitable stripping agent should not be harmful to health and the environment, ie it should not contain any of the abovementioned solvents, acids or bases, act on a very wide range of paints and binders in as short a time as possible, do not cause smearing of the old paints, not the various substrates attack and be removed if possible with water.
  • a nail polish remover should be able to quickly and neatly remove the applied coatings from the nail without causing the above damage patterns.
  • Highly degreasing solvents should not or only in small amounts be used, moisturizing and moisturizing substances should be available in sufficient quantity, but must not hinder the removal of the paint or delay.
  • aerosol paints and other colorants used to create graffiti there are a number of polymeric paint binders used in nail polish formulations.
  • a suitable nail polish remover must also be able to detach all these different paint compositions equally well from the substrate. Just as in the case of the graffiti remover, but in this case of somewhat lesser importance, when using the nail polish remover the colorants should not smeared.
  • Object of the present invention was therefore to provide a detergent for a wide range of building surfaces and also for skin, hair and fingernails available that ensures a quick and thorough removal of paint or paint without smearing.
  • the cleaning agent should not be harmful to health or the environment and should not be able to dissolve a wide range of paints and varnishes.
  • the object of the invention is achieved by providing a cleaning agent, characterized in that the cleaning agent comprises a microemulsion or a fluid nanophase system and comprises the following components: a) at least one water-insoluble substance (oil) having a solubility in water of less than 4 g per liter ; b) at least one amphiphilic substance, NP-MCA, which does not have a directed hydrophilic-hydrophobic surfactant structure, does not structurally alone, i.
  • the cleaning agent comprises a microemulsion or a fluid nanophase system and comprises the following components: a) at least one water-insoluble substance (oil) having a solubility in water of less than 4 g per liter ; b) at least one amphiphilic substance, NP-MCA, which does not have a directed hydrophilic-hydrophobic surfactant structure, does not structurally alone, i.
  • NP-MCA is not selected from 2-ethyl 1, 3-hexanediol, 2-methyl-2,4-pentanediol, 2- (n-butyl) -2-ethyl-1, 3-propanediol and / or from 1, 2-diols; c) at least one anionic, cationic, amphoteric and / or nonionic surfactant; d) water and / or a water-soluble solvent with hydroxyl functionality and, if appropriate, auxiliaries,
  • the cleaning agent may comprise a further amphiphilic substance.
  • Microemulsions are thermodynamically stable, nanostructured fluids that consist of at least water or a water-like liquid (eg, glycerol), oil, and a surfactant. Some microemulsions still contain cosurfactants and (if ionic surfactants are used) possibly salts.
  • the structure sizes of the microemulsions are usually between 10 and 200 nm. In contrast to the kinetically stable emulsions or nanoemulsions, the thermodynamically stable microemulsions do not tend to cream by particle coalescence.
  • microemulsions short-term larger structures disintegrate some time later into smaller micelles. It follows that microemulsions form by their thermodynamic stability even without mixing by itself. In contrast to emulsions, not only spherical micelles, but also elongated micelles (worm-like micelles) and diverse network-like structures occur in microemulsions. In the most favorable case, a bicontinuous structure exists in a microemulsion. Here, water and oil phase penetrate via sponge-like interfaces of surfactants and possibly cosurfactants.
  • NP-MCA nanojDhase-forming mixed-chain structure amphiphiles
  • NP-MCAs causes an extension of the thermodynamically stable, single-phase existence of nanostructured systems. This was all the more surprising because the experts had previously assumed that the more different the lipophilic and the hydrophilic parts are in their respective opposite phase in terms of their solubility, the sooner microemulsions can form. Therefore, the skilled person for the production of so-called microemulsions has basically taken oils and hydrophilic components that are as little as possible to solve each other.
  • NP-MCA non-structure-forming, mixed-structured amphiphiles
  • the present invention overcomes a long-standing in the professional world prejudice.
  • NP-MCAs to an oil / water / surfactant mixture causes a significant widening of the single phase region of the resulting nanophase fluids over conventional microemulsions and, compared to conventional microemulsions, the lamellar phase (La) in one Phase diagram, so that the occurrence of high viscosity lamellar phases in which the oil and water domains are disadvantageously layered is prevented or at least diminished (see FIG. 10).
  • Nanophase fluids contain water or a water-like substance, oil, at least one structure-forming amphiphile, which attaches to the oil-water interface and - in extension to the microemulsions - at least one further non-structure-forming amphiphile without surfactant structure (NP-MCA).
  • the structure-forming amphiphile is a surfactant, cosurfactant or a surfactant-like oligomer or polymer.
  • the NP-MCAs are important for the extension of the thermodynamically stable area of existence of the fluid nano-phases and therefore a further delimitation criterion for the microemulsions.
  • NP-MCAs allows a significant widening and possibly lowering of the temperature window of the single-phase region.
  • NP-MCAs prevent or reduce the occurrence of high-viscosity lamellar phases, possibly reducing the required surfactant concentration and greatly expanding the properties and applications of the fluids.
  • Nanophase-forming-mixed-chain structure amphiphiles are mixed-structured amphiphiles that have hydrophilic and hydrophobic molecular regions that are spatially close together but mixed in such a way that they do not have any Possess surfactant-like structure. Thus, they differ from surfactants and cosurfactants, which maintain their function by the directed separation of both areas (head-tail structure).
  • NP-MCA are not capable of forming superstructures by themselves and preferably do not accumulate at the oil-water interface.
  • a surfactant is additionally required for the formation of nanophase fluids.
  • NP-MCA have significant solubility in the water phase or oil phase and are distributed throughout this until equilibrium is established.
  • the solubility of the NP-MCA in water or oil is generally between 4 and 1000 grams per liter, possibly also in the form of its salts.
  • An NP-MCA according to the present invention is an amphiphilic substance which does not have a directional hydrophilic-hydrophobic surfactant structure, not structurally by itself, i. is not micelle-forming, whose solubility in water or oil is between 4 g and 1000 g per liter and which does not preferentially accumulate at the oil-water interface, with the proviso that NP-MCA is not selected from 2-ethyl 1, 3-hexanediol, 2-methyl-2,4-pentanediol, 2- (n-butyl) -2-ethyl-1, 3-propanediol and / or from 1, 2-diols.
  • the phase diagram shows a triangle between the temperature and surfactant concentration (fish or whale diagram) X-point and the crossing points of the boundary region of the single-phase to the two-phase region and the parallel to the ordinate applied tangent of the incipient L ⁇ region are spanned.
  • Measurement methods for the preparation of the surfactant concentration-temperature phase diagram are known to the person skilled in the art.
  • NP-MCAs lead to a widening of the area of existence of the single-phase area as well as to an enlargement of the area of this triangle and can be defined by it.
  • NP-MCAs preference may be given to all amphiphiles which, when 4% added to an oil-water surfactant system lead to an enlargement of the surface area of these triangles of at least 5%, without changing the surfactant system of at least 10% and most preferably at least 20%.
  • the area of the triangle is increased in a range of 5% to 2000% without changing the surfactant system, preferably from 10% to 1000%, most preferably from 15% to 500%.
  • NP-MCA which are characterized in that, when added to an oil-water-surfactant system comprising the constituents oil a),
  • Corner points i) the X-point, ii) the upper crossing point of the boundary region of the single-phase to the two-phase region with the parallel to the temperature coordinate applied
  • phase diagram fish diagram, whale-diagram
  • samples with a constant ratio of the non-surfactant components and a surfactant content which is increased stepwise from 0% to a desired amount of surfactant (possibly up to 100%) are used .
  • the step width depends on the requirements of the measurement accuracy, with a step size of 2% is usually sufficient.
  • These samples are left in a thermostated medium (preferably water, possibly with freezing point-lowering additives) at temperatures from - 30 0 C to 100 0 C until the phase equilibrium is adjusted and then the phase state is assessed visually on the light scattering.
  • the width of the temperature steps results from the desired measurement accuracy, for technical applications usually a step size of 1 0 C is sufficient.
  • phase boundaries result from the transition from one phase state to the next, the error being predetermined by the step size of the temperature measurement.
  • the measurement points thus obtained are recorded in a diagram and connected to each other, wherein the temperature is plotted against the surfactant content. It is usually sufficient to find the phase states existing in the measuring range of a sample and to determine the phase boundaries by means of interval nesting.
  • the value for the phase expansion of the nanostructured fluid composition is determined by representing a triangle in the phase diagram of Figure 10, such that a first straight line a) starting at the X-point is characterized by the phase state above the average temperature Curve (dash over 2) is formed, a second straight line b) is formed so that it tangentially touches the opening angle of La and the first straight line a) at the location of their tangential contact point with the above the average temperature characterizing curve (dash over 2) and a third line c) is placed on the phase characteristic below the average temperature curve (line below 2) so that it intersects the two straight lines a) and b).
  • Preferred NP-MCA are characterized in that they are added to an at least 5% by weight with an addition of 4% by weight, based on the total weight of the cleaning agent, of an oil-water-surfactant system comprising constituents a), c) and d) % increase of the temperature range .DELTA.T of the single-phase existence range of the cleaning agent, which is determined by the determined in the phase diagram as a function of temperature and surfactant concentration length of the parallel to the temperature axis tangent to the L ⁇ area, which is limited by the intersections of the tangent with the lower and upper dividing line between one-phase and two-phase existence range of the cleaning agent (see Fig. 10).
  • NP-MCA lead to an increase in the temperature range .DELTA.T of 10% to 1000%, most preferably from 20% to 500%.
  • the influencing of the temperature range .DELTA.T can additionally or alternatively be made to increase the area and / or the circumference of the triangle.
  • NP-MCA are molecules that consist of carbon, hydrogen and at least one of the following types of atoms (heteroatoms): silicon, oxygen, nitrogen, sulfur, phosphorus, fluorine, chlorine, bromine, iodine.
  • Polar carbon atoms are next to heteroatoms. Polar carbon atoms are not counted to an alkyl chain or non-polar chain.
  • NP-MCA within the meaning of the invention are v.a.
  • alcohols ketones, esters, heterocycles of 5 to 7 atoms per cycle, ethers, amides and amines, N-acylated amino acids, and some aldehydes find that have no surfactant-like structure, so no directed head-tail structure.
  • hydrophilic and hydrophobic regions are intermixed in the molecule such that: i) no terminal nonpolar chain located on a primary or secondary carbon atom has 4 or more carbon atoms. If the chain is longer, it must not exceed 20% of the molecular weight; ii) an intramolecular or non-polar chain located on a tertiary carbon atom is not longer than 7 carbon atoms (ie, greater than, for example, 1, 9-nonanediol) and greater than 20% of the molecular weight.
  • a composition comprising such non-structure-forming, mixed-structure amphiphiles from the group of the alcohols, amines and alcoholamine is also provided by the present invention.
  • NP-MCA may in particular also be ketones or acids and their weak salts and amides, as well as organyl sulfates and phosphates. Due to their slightly higher polarity compared to alcohols, chain length increases by 1 for both terminal and intramolecular chains.
  • composition comprising such non-structure-forming, mixed-structured amphiphiles from the group of ketones or acids and their weak salts and amides, as well as organyl sulfates and phosphates, is also an object of the present invention.
  • NP-MCA may also be alkyl, alkenyl, alkynyl, arylsulfides, phosphides and silicones / siloxanes. Due to the lower polarity here is compared to alcohols by 1 reduced chain length.
  • composition comprising such non-structure-forming, mixed-structured amphiphiles with alkyl, alkenyl, alkynyl radicals or from the group of the aryl sulfides, phosphides and silicones / siloxanes is likewise provided by the present invention.
  • NP-MCAs which contain more than one of the abovementioned functionalities are particularly preferred according to the invention, it also being possible for different functional groups to occur in the molecule.
  • chain lengths for the delimitation of conventional surfactant-like molecules the chain lengths given for alcohols are used, provided that the functionalities are not predominantly ketones, acids and their weak salts, amides or organyl sulfates or phosphates.
  • Preferred NP-MCA are selected from diols of the formula I:
  • n 0, 1, 2, 3 or 4
  • Ri and R 2 are each independently hydrogen or a straight or branched Ci - C3 alkyl, with the
  • Ri can not be hydrogen and the diol is not 2-methyl-2,4-pentanediol.
  • particularly preferred NP-MCA are selected from the following diols: 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 2,3-butanediol, 2, 4-pentanediol or 2,5-dimethyl-2,5-hexanediol.
  • the diols mentioned are particularly suitable for providing a cosmetic and / or dirt remover.
  • Preferred NP-MCA are selected from acetoacetates of the formula II:
  • Each R 3 is independently hydrogen or a C 1 to C 2 alkyl and
  • R 4 is a branched or unbranched C 1 to C 4 alkyl
  • R 5 is C 1 to C 4 alkyl;
  • particularly preferred NP-MCA are selected from the following acetoacetates: ethyl acetoacetate, iso-propyl acetoacetate, methyl acetoacetate, n-butyl acetoacetate, n-propyl acetoacetate or tert-butyl acetoacetate.
  • the acetoacetates mentioned are particularly suitable for providing a dirt remover, tile cleaner, cosmetics remover, hair detoxifier, graffiti remover, stripper and / or nail polish remover.
  • NP-MCA are selected from diones of formula IV
  • particularly preferred NP-MCA are selected from the following
  • the dione mentioned are particularly suitable for providing a
  • Cosmetic remover dirt remover, nail polish remover and / or
  • NP-MCA are selected from esters of the formula V.
  • R 6 is a ring bond to R 7 , CH 3 or COCH 3 and R7 (CH 2 ) 2 - O - ring bond to R 6 , (CH 2 ) 2 - O - (CH 2 ) 3 - CH 3 , CH 2
  • particularly preferred NP-MCA are selected from the following esters: (1-methoxy-2-propyl) -acetate, (2-butoxyethyl) -acetate, ethylene carbonate, ethylpyruvate (2-oxopropionic acid ethyl ester), or propylene carbonate.
  • esters are particularly suitable for providing a dirt remover, tile cleaner, cosmetics remover, hair detoxifier, graffiti remover, stripper and / or nail polish remover.
  • NP-MCA are selected from maleic or fumaric acid amides of the formula VI
  • Rs is hydrogen, a branched or unbranched Ci - C 4 alkyl, or a branched or unbranched, linear or cyclic Ci
  • C 6 is alkyl, where the C 1 -C 6 -alkyl is substituted by one or more groups selected from OH, NH 2 , COOH, CO, SO 3 H, OP (OH) 2 , and R 9 is hydrogen or a branched or unbranched C 1 - C 4 is alkyl.
  • NP-MCA are selected from the following maleic acid amides and their methyl, ethyl, propyl and butyl esters: N-methylmaleamide; N-Ethylmaleamid; N- (n-propyl) -maleamid; N- (i-propyl) -maleamid; N- (n-butyl) -maleamid; N (i-Butylmaleamid); N- (tert-butylmaleamide), as well as the corresponding fumaric acid amides and their methyl, ethyl, propyl and butyl esters.
  • NP-MCA are selected from: 2,2-dimethoxypropane, pyruvic aldehyde-1, 1-dimethylacetal, diacetan alcohol (2-methyl-2-pentanol-4-one), 2-butanol, 2-acetyl-gamma-butyrolactone, 3-amino-1H-1, 2,4-triazole, gamma-butyrolactone, nicotinamide, ascorbic acid, N-acetylamino acids, especially N-acetylglycine, alanine, cysteine, valine or arginine, triethyl phosphate, n-butyl acetate, dimethyl sulfoxide or 2,2,2-trifluoroethanol.
  • N-acetylamino acids are useful for providing cosmetic removers.
  • NP-MCA which are selected from the group consisting of ethyl acetoacetate; i-propylacetoacetate; methyl acetoacetate; Methyl isobutyryl acetate (methyl (4-methyl-3-oxopentanoate)); n-butyl acetoacetate; n-propyl acetoacetate; tert-butyl acetoacetate; allyl; Maleic acid amide (maleamic acid, maleamide), the following maleamides and their methyl, ethyl, propyl and butyl esters: N-methylmaleamide; N-ethylmaleamide; N- (n-propyl) -maleamid; N- (i-propyl) -maleamid; N- (n-butyl) maleamide; N (i-Butylmaleamid); N- (tert-Butylmaleamid); and the corresponding fumaric acid amides
  • hydroxybenzaldehyde 4-hydroxybenzoic acid; 5-methylresorcinol; acetylsalicylic acid; butylhydroxytoluene; N-phenyl-2,2'-iminodiethanol;N-phenylurea; methyl ethyl, propyl 4-hydroxybenzoate; sulfanilic; vanillin; (2-ethoxyethyl) acetate; (2-ethoxyethyl) methacrylate; (2-Hydroxypropoyl) methacrylate; [2- (2-butoxyethoxy) ethyl] acetate; 1,2-propylene glycol diacetate; diethyl malonate; Dimethyl-acetylsuccinate; dimethyl carbonate; dimethyl fumarate; dimethyl; dimethyl; ethyl acetate; ethylene glycol; ethyl formate; ethyl lactate; glycerol triacetate; isopropeny
  • the NP-MCA in the inventive detergent from 1 to 80 wt .-% based on the total weight of the detergent, more preferably from 2 to 25 wt .-%, most preferably from 10 to 24 wt .-%.
  • oils for the purposes of the present invention.
  • Oil refers to all hydrophobic substances that do not mix homogeneously with water or a water-like liquid and form a separate phase. Since some oils still dissolve to a large extent in water, an additional water solubility of less than 4 grams per liter is defined here.
  • the water-insoluble substances are preferably those having a water solubility of less than 2 g per liter. These include z. As alkanes (gasolines) and cycloalkanes (preferably cyclohexane).
  • Aromatics such as toluene, xylene or other alkylbenzenes and naphthalenes are also suitable.
  • Preferred are long-chain alkanoic acid esters, such as fatty oils and fatty acid alkyl esters or fatty alcohol ethers.
  • Benzyl acetate is also one of the water-insoluble substances used according to the invention.
  • terpenes, z As monocyclic monoterpenes with cyclohexane, can be used. Particularly preferred here are terpenes from citrus fruits, such as citric and / or orange terpenes or the limonene contained therein.
  • the water-insoluble substances are preferably from 1 to 90 wt .-% in the detergent, more preferably from 1, 5 to 30 wt .-% based on the total weight of the detergent.
  • amphiphilic substances for example, higher alcohols can be used.
  • Cotensides with hydrophilic-lipophilic molecular fractions, such as, for example, are particularly preferred.
  • cycloalkanols such as cyclohexanol or particularly preferred
  • Phenyl alcohols such as phenylmethanol (benzyl alcohol), 2-phenylethanol and 3-phenyl
  • short-chain fatty acids such as hexane, heptane, octanoic acid and their
  • Alkali or ammonium salts find use. Particularly preferred are their
  • the further amphiphilic substances are preferably contained in the composition according to the invention from 2 to 45% by weight, based on the total weight of the cleaning agent, more preferably from 2 to 40% by weight.
  • the further amphiphilic substance particularly preferably has a water solubility of from 2 g to 128 g per liter and is selected from the group comprising C 4 -C 12 -alcohols, cycloalkanols, phenyl alcohols, short-chain fatty acids or their alkali metal or ammonium salts.
  • the cleaning agent further comprises anionic, cationic, amphoteric and / or nonionic surfactants. In the following list some preferred surfactants are mentioned.
  • alkali metal or ammonium salts of long-chain fatty acids alkyl (benzene) sulfonates, paraffin, bis (2-ethylhexyl) sulfosuccinate, alkyl sulfates, such as sodium dodecyl sulfate and for special applications where it depends, for example, on corrosion protection, sometimes alkyl phosphates (eg phospholane ® PE 65, Akzo Nobel) are used.
  • the nonionic surfactants can polyalkylene oxide-modified fatty alcohols, such as Berol ® types (Akzo Nobel) and Hoesch T types (Julius Hoesch), as well as appropriate Octylphenols (Triton types) or nonylphenols (if the latter are not released in large quantities into the environment).
  • a particular area enable heptamethyltrisiloxanes (for example Silwet ® grades, GE Silicones), as a means to increase the spreading properties of the strong liquid or to the considerable reduction of the interfacial tension.
  • cationic surfactants e.g. coconut bis (2-hydroxyethyl) methyl ammonium chloride or polyoxyethylene modified tallow methyl ammonium chloride find use.
  • the use of various amphoteric surfactants is possible. If a broad pH range is to be covered, the coco dimethylamine oxide (Aromox® MCD, Akzo-Nobel) has proven to be suitable.
  • the surfactants are contained in the detergent preferably from 9 to 16 wt .-%, based on the total weight of the cleaning agent.
  • the cleaning agents according to the invention can be mixed with excipients which facilitate or improve the application.
  • This is z. B. to a thickening to facilitate the application of the cleaning agent to the substrate, to a reduction in the inflammability, an odor enhancement, an effect enhancement, a cost reduction of the active ingredients or a corrosion protection.
  • the sum of the excipients preferably makes up not more than 20% by weight of the formulation, the amount of a single adjuvant is often not more than 10% by weight.
  • a) Thickening Most surfaces of a use case are vertical walls from which low-viscosity liquids run too fast from the point of damage of a graffiti downwards. A thickening of the liquids is so low, to delay the drainage or even prevent. Commercially available thickeners can be used to thicken the low-viscosity liquids resulting from the experiments. Particularly preferred is fumed silica, such as Aerosil ® 380 for sale.
  • b) Flame retardant As the graffiti remover may contain some volatile substances, a flame retardant may be useful.
  • the agent can be set self-extinguishing.
  • TEP triethyl phosphate
  • TEHP trioctyl phosphates, such as tris (2-ethylhexyl) phosphate
  • Odor improvement If the formulation is to be improved in odor for the end user, this can be done with a number of common odorous substances. Examples which may be mentioned are esters such as methyl butanoate (pineapple), ethyl methanoate (raspberry), pentyl ethanoate (banana), pentyl pentanoate (apple), pentyl butanoate (apricot) octyl ethanoate (orange). The latter can z. B. also be well combined with orange terpenes or D-limonene, which may be an example of a lipophilic active ingredient in the liquid according to the invention. Other odors are found in the field of terpenes, such as. B. geraniol.
  • the cleaning agent contains:
  • composition of the invention which is a liquid consisting of at least four but usually more components, surprisingly triggers coatings and coatings much more effective, cleaner and sometimes faster from different substrates than a) conventional graffiti removers (see Fig. 1), strippers or nail polish remover on the usual solvent-based or as a general solvent, even if they are known to be good solvating b) the individual components per se (see Fig. 2) c) Mixtures of the solvent components without water and / or without surfactants d) conventional graffiti removers on a known emulsion basis or the emulsions prepared from the solvent components e) Mixtures of water and surfactants.
  • these liquids solved the graffiti paints at least as well from the subsurface as the most effective solvents of the moreover tested solvents, thus in particular e.g. Tetrahydrofuran, 1-methyl-2-pyrrolidone, 1-methoxy-2-propanol, butyrolactone or dichloromethane.
  • the primary cleaning effect was not a priori in a physical dissolution of the paint, since no paint binder is solved by the liquids molecular dispersion, but in a b) strong swelling of the paint, partly in wave-like form, partly with microscopic holes in the paint layer and a subsequent fragmentation (fragmentation) of the lacquer layer in approximately 100 microns to 2 mm large pieces of paint and c) submerging large areas of the lacquer layer with subsequent lifting of the layer.
  • a) in undiluted form swelling or solubilization of graffiti paint binder systems, usually in conjunction with fragmentation of the paint - in the case of swelling, also undermining of the paint layer down to the substrate b) together with small amounts of water, e.g. In a damp sponge, brush or brush occur: Forming a wash and lifting the swollen and / or dissolved paint particles from the substrate.
  • the Graffitientferner system according to the invention shows a selectivity, ie high-quality facade paints are not replaced within the exposure time. In the case of the stripper, this selectivity is not required, since here also underground coatings must be lifted with.
  • the systems according to the invention show a very rapid swelling and detachment of the colors; depending on age, background and color, usually within 10 seconds to about 30 minutes (preferably 20 minutes) for the graffiti remover, 20 minutes to 3 hours for the stripper and 3 to 30 seconds (preferably 3 to 20 seconds) for the nail polish remover.
  • the invention thus also relates to the use of cleaning agents according to the invention as graffiti removers, strippers or nail polish removers.
  • the invention also provides a process for removing unwanted paints and varnishes from surfaces.
  • the inventive method for removing unwanted paints and coatings from surfaces is characterized in that the cleaning agent according to the invention is applied to the unwanted paint or paint, and then the color or the paint is removed with water, wherein the contact time of Graffitientferner of about 10 seconds to about 30 minutes, the stripper from about 20 minutes to about 3 hours, and the nail polish removal from about 3 to about 30 seconds.
  • the invention further relates to the use of inventive Detergents as dirt removers, tile cleaners, cosmetic removers or hair detoxifiers without oxidative bleaching.
  • Dirt is understood to be the presence of at least one component selected from carbon black, grease, oil, silicone, particulate matter, resin and / or mixtures comprising one or more of these constituents.
  • Cosmetics are understood to mean cosmetics, in particular those applied to the skin and / or skin appendages, such as hair or nails. Hair is understood to mean both artificial hair and natural hair. Hair dyes are understood as means that dye hair without oxidizing it.
  • the invention also provides a process for removing dirt (for example, carbon blacks, fats, oils, silicones, fine dusts, resins and mixtures containing one or more of these constituents) from surfaces such as ceramic, tile or plastic surfaces, from cosmetics or for hair discoloration , characterized in that a cleaning agent according to the invention is applied to the dirt to be removed cosmetics or the hair to be bleached, and then the dirt, the agent or the color is removed with water, wherein the contact time of the dirt remover of about 10 seconds about 3 hours, about 10 seconds to about 30 minutes for the cosmetic remover and about 2 minutes to about 24 hours for the hair remover.
  • dirt for example, carbon blacks, fats, oils, silicones, fine dusts, resins and mixtures containing one or more of these constituents
  • the invention relates to an experienced for the preparation of the cleaning agent according to the invention.
  • the inventive method for producing a cleaning agent is characterized in that water or a solvent presented with hydroxy functionality and an anionic, cationic, amphoteric and / or nonionic surfactant at 10 to 90 0 C is dissolved with stirring therein, water-insoluble substance ( en) are added in parallel or after addition of surfactant and then the resulting emulsion by the addition of another amphiphilic substance and NP-MCA in an optical transparent extended microemulsion or a nanophase system is transferred and optionally adjuvants are added at the end of the mixing process.
  • the detergent is prepared by initially presented in a suitable vessel water or the solvent with hydroxy functionality and then the surfactant is dissolved with stirring.
  • some surfactants may already contain water as supplied, so the amount of water calculated in the recipe may need to be corrected.
  • dissolving the surfactant care must be taken to keep the air in the solution as low as possible to avoid excessive foaming.
  • agitators and stirrers for large-scale implementation in order to largely avoid foaming.
  • the stirring speed should usually not exceed 200 revolutions per minute.
  • care must be taken that some (concentrated) surfactants can form gels when water is added, which can complicate stirring and further distribution.
  • the water-insoluble substances (oil phase) must be added first or in parallel with the addition of surfactant. Foaming can also be prevented by the subsequent addition of the oil phase, since these often have a certain defoaming action.
  • a milky-cloudy emulsion is formed, which by the addition of another amphiphilic substance with surfactant structure (eg alkanol), but at the latest after addition of the amphiphile according to claim 1 b (eg the acetoacetate compound) clears and finally in an optical transparent extended microemulsion or a nanophase system passes.
  • additives such as e.g. flame retardants (e.g., triethyl phosphate), thickening agents (e.g., aerosils), and / or other adjuvants.
  • the invention also provides a process for the preparation of a cleaning agent according to the invention, characterized in that water or a solvent presented with hydroxy functionality and an anionic, cationic, amphoteric and / or nonionic surfactant at 10 to 90 0 C below Stirring is added thereto, water-insoluble substance (s) are added in parallel or after addition of surfactant and then the resulting emulsion by the addition of another amphiphilic substance and NP-MCA in an optically transparent microemulsion or nanophase system is transferred and optionally at the end of the mixing process Additives are added.
  • the formulation of the invention shows no color shade, no impairment of the original facade color (white) and no color gradients at the edges, but a sharp demarcation to the untreated area.
  • the individual components c) and d) of the nanophase fluid b) show no effect on the detachment of the paint; Component e) is a poor solvent.
  • a commercial Kosmetikentferner was used and under 2 an inventive Detergent with nanophase structure.
  • the numbers at the bottom of b) indicate the cleaning cycles, ie how many times was wiped with a cotton pad soaked with the appropriate detergent with light pressure and only in one direction over the place.
  • Effectiveness of cleaning agents according to the invention as hair removers with a) condition after cleaning and b) condition before cleaning.
  • Fig. 8 Effectiveness of inventive detergents in tile cleaning compared to non-nanophase-forming detergents, wherein in each case in a) the state before the cleaning and in b) the state after purification is shown. Under 1) the results for a microemulsion are shown, under 2) the results for an emulsion system and under 3) the results of a nanophase system according to the invention.
  • FIG. 9 shows the nanostructuring of the fluid NP2 by means of a freeze-fracture electron microscopy (freeze-fracture electron microscopy).
  • the smaller spherical structures (arrow) are about 20-50 nm large micelles of the water phase, which are distributed within a low-structured oil phase.
  • Phase diagram (fish diagram or whale diagram), which shows the course of the single-phase and biphasic and lamellar existence ranges of a cleaning agent as a function of the surfactant concentration and the temperature.
  • a composition is shown as microemulsion
  • the presence of NP-MCA leads to an increase in the temperature range ⁇ T.
  • the graffiti remover from example 1 was prepared by initially introducing water into a suitable vessel and dissolving therein the surfactant (sodium lauryl sulfate) with stirring. When dissolving the surfactant, the air in the solution should be kept as low as possible. Foaming can be prevented by the subsequent addition of the orange terpenes, since these have a certain defoaming action. After this step, a milky-cloudy emulsion has formed, which becomes clear with the addition of 1-hexanol and ethyl acetoacetate and finally turns into a completely transparent nanophase system. At the end, the triethyl phosphate is added.
  • the surfactant sodium lauryl sulfate
  • the graffiti remover from Example 2 was prepared by the process technology analogously to Example 1.
  • the graffiti remover from Example 3 was prepared by a process analogous to Example 1.
  • the stripper from Example 4 was prepared by the process technology analogously to Example 1.
  • the nail polish remover of Example 5 was prepared by sprinkling the surfactant (sodium lauryl sulfate) into a mixture of water, ethyl acetoacetate and 2-phenylethanol with gentle stirring at stirring speeds of 100 rpm. After formation of the nanophase system, the fragrance was added.
  • the surfactant sodium lauryl sulfate
  • Table 1 Effect of the graffiti removers of the invention prepared in Examples 1 and 3 within 5 minutes exposure time
  • Table 2 Effect of the nail polish remover according to the invention according to Example 5: after a single application of the remover with cotton pads and then washing the nails with water
  • an exhaust air box was chosen, which had taken over a period of about 10 years outdoors the precipitates of birch trees (birch resin) on its white lacquer layer.
  • Commercially available cleaning agents did not result in cleaning success. Both agents were allowed to act for 2 minutes and then rinsed with wet sponges.
  • composition of the fluid for cleaning (lisoCLEAR 55 DAA - the formulation was developed for tile, ceramic, façade and paint cleaning):
  • NP-MCA diacetone alcohol (DAA) 3.47% ethylacetoacetate 12.28%
  • Ingredients result in a different effect, depending on whether it is a microemulsion, a conventional emulsion or a nanophase fluid.
  • compositions of the fluids were used for tile cleaning:
  • Composition 1. is a microemulsion
  • Composition 2 an emulsion system and Composition 3. the nanophase system lisoCLEAR 55 nPMA - (the formulation was developed for tile, ceramic, façade and paint cleaning).
  • Composition 1 Microemulsion as a comparison system for tile cleaning
  • composition 2 Emulsion system as a comparison system for
  • NP-MCA ethylacetoacetate 9.55%
  • composition 3 Nanophase fluid lisoCLEAR 55 nPMA water phase: water 55.28%
  • Oil phase orange terpene 11, 35%
  • Surfactant sodium dodecyl sulfate 8.80%
  • NP-MCA ammonium n-propylnanine anide
  • make-up removal agents disadvantageously consist of two phases which must be shaken shortly before to form an emulsion. After often less than a minute or two, the phases separate again (the oil phase is framing).
  • nanophase fluid consists of very gentle, skin-friendly ingredients that individually, if at all, have only a weak cleaning action. In the form of a nanostructured system, however, the effect exceeds that of commercial products.
  • the numbers at the bottom of the picture b) indicate the cleaning cycles, ie how many times was wiped with a cotton pad that had been soaked with detergent with light pressure and only in one direction (towards the fingers) over the place.
  • NP-MCA ethyl acetoacetate 12.25%
  • a tuft of hair dyed with black hair dye was stored overnight (16.5 hours) in Fluid 42.
  • the discolored hairs (a) were compared with the untreated hair tufts (b). Results are shown in FIG. It turns out that a discoloration of the treated hair has set.
  • Composition of the fluid V42 Water phase: water 28.48%
  • NP-MCA Ethylacetoacetate 21, 31%
  • Nanophase fluid NP 2 (graffitiCRACK liquid):
  • NP-MCA triethyl phosphate 5.15%
  • NP-MCA diacetone alcohol 3.47%
  • NP-MCA diacetone alcohol 11, 74%
  • Example 11 Comparative Experiments Nanophase Fluids vs. Microemulsions in a paint removal experiment
  • Glycerol 8.34%, ethanol: 8.30%, diacetone alcohol: 35.02%, ethyl acetoacetate: 21. 00%, n-butyl acetate: 6.64%, hexanol: 8.26%, benzyl acetate: 8.30% , Orange terpenes: 4,15%.
  • Surfactant sodium dodecyl sulfate (SDS) 13.18%, C9-C11 alcohol ethoxylate (4) 2.13%; Cosurfactant: NP-MCA: diacetone alcohol: 8.741%, acetylacetone: 8.71%.
  • Nanophase fluid NP 2 (graffitiCRACK liquid): fragmentation of the lacquer, very good peeling of the lacquer
  • Water phase water: 21, 04%;
  • Oil phase orange terpene: 10.63%, benzyl acetate: 10.52%;
  • NP-MCA triethyl phosphate: 5.15%, ethyl acetoacetate: 18.38%, n-butyl acetate: 8.45%.
  • Oil phase orange terpenes: 24.46%
  • Microemulsion ME 1 (V142): nanostructured, but slower in paint removal as a microemulsion
  • Oil phase orange terpene 34.21%
  • Cosurfactant hexanol 20.58%)
  • red product Auto K (20330, VW / Audi, Marsred, L31 B) yellow: product Auto K (22218, FORD, signal yellow, 77 KLP / 97 green: Product Car K (21395, OPEL, mint green, 361) silver: Product Monex, Paint Spray (Rallye silver rim, 7093) blue: Product Dupli Color, (sky blue, satin mat, DCP 5200 / RAL 5015)
  • nanostructured fluids in turn, a difference can be seen, whether it is a microemulsion or a phase-expanded system (nanophase fluid).
  • phase-expanded system nanophase fluid
  • the lowest in peelability showed the microemulsion.
  • the most obvious effect was graffitiCRACK.
  • Example 12 further selected example formulations for cleaning agents according to the invention
  • NP-MCA dimethyl sulfoxide, 2,2,2-trifluoroethanol

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Abstract

L'invention concerne un agent de nettoyage, caractérisé en ce que l'agent de nettoyage comporte une microémulsion ou un système de nanophases fluide et comprend les constituants suivants : a) au moins une substance insoluble dans l'eau qui a une solubilité dans l'eau inférieure à 4 g par litre ; b) au moins une substance amphiphile, NP-MCA, qui ne comporte pas de structure tensioactive, qui n'est pas structurante seule, dont la solubilité dans l'eau ou l'huile est comprise entre 4 g et 1 000 g par litre et qui ne s'accumule de préférence pas à l'interface huile-eau, à condition que NP-MCA ne soit pas choisi parmi le 2-éthyl-1,3-hexanediol, le 2-méthyl-2,4-pentanediol, le 2-(n-butyl)-2-éthyl-1,3-propanediol et/ou parmi les 1,2-diols ; c) au moins un tensioactif anionique, cationique, amphotère et/ou non ionique ; d) de l'eau et/ou un solvant soluble dans l'eau qui comporte une fonctionnalité hydroxy et éventuellement des adjuvants.
EP08804501A 2007-09-19 2008-09-19 Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage Withdrawn EP2195408A2 (fr)

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EP10004122.7A EP2223995B2 (fr) 2007-09-19 2008-09-19 Produit de nettoyage pour la suppression de couches de couleurs de surfaces, procédé de fabrication du produit et procédé de nettoyage
EP08804501A EP2195408A2 (fr) 2007-09-19 2008-09-19 Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage

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EP07116792A EP2045320B1 (fr) 2007-09-19 2007-09-19 Produit de nettoyage pour la suppression de couches de couleurs de surfaces, procédé de fabrication du produit et procédé de nettoyage
PCT/EP2008/062573 WO2009037349A2 (fr) 2007-09-19 2008-09-19 Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage
EP08804501A EP2195408A2 (fr) 2007-09-19 2008-09-19 Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage

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EP08804501A Withdrawn EP2195408A2 (fr) 2007-09-19 2008-09-19 Formulations pour l'élimination de couches colorées et de diverses couches de salissures sur des surfaces, procédé de fabrication de l'agent et procédé de nettoyage
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EP2045320A1 (fr) 2009-04-08
EP2223995B2 (fr) 2024-12-11
WO2009037349A2 (fr) 2009-03-26
EP2223995B8 (fr) 2018-06-13
EP2223995A3 (fr) 2011-04-20
JP2010539316A (ja) 2010-12-16
JP5844523B2 (ja) 2016-01-20
EP2223995A2 (fr) 2010-09-01
EP2045320B1 (fr) 2012-04-25
BRPI0817128A2 (pt) 2015-10-27
CN101861381B (zh) 2016-03-30
US20110229424A1 (en) 2011-09-22
WO2009037349A3 (fr) 2009-12-30
EP2223995B1 (fr) 2018-03-07
US20140274855A1 (en) 2014-09-18
CN101861381A (zh) 2010-10-13
CN105779146A (zh) 2016-07-20
ATE554743T1 (de) 2012-05-15

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