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WO1992000355A1 - Pigments a base d'hydroxydes a double couche, leur procede de production et leur utilisation - Google Patents

Pigments a base d'hydroxydes a double couche, leur procede de production et leur utilisation Download PDF

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Publication number
WO1992000355A1
WO1992000355A1 PCT/EP1991/001119 EP9101119W WO9200355A1 WO 1992000355 A1 WO1992000355 A1 WO 1992000355A1 EP 9101119 W EP9101119 W EP 9101119W WO 9200355 A1 WO9200355 A1 WO 9200355A1
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WO
WIPO (PCT)
Prior art keywords
water
double
pigments
pigments according
layer hydroxides
Prior art date
Application number
PCT/EP1991/001119
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German (de)
English (en)
Inventor
Wolfgang Breuer
Helmut Endres
Günter GEISMAR
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Filing date
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1992000355A1 publication Critical patent/WO1992000355A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium, with or without oxygen or hydrogen, and containing two or more other elements
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B63/00—Lakes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other 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
    • C11D3/40—Dyes ; Pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/20—Two-dimensional structures
    • C01P2002/22—Two-dimensional structures layered hydroxide-type, e.g. of the hydrotalcite-type
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/78—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by stacking-plane distances or stacking sequences

Definitions

  • Pigments based on double layer hydroxides Process for their preparation and their use
  • the present invention relates to water-insoluble pigments based on double-layer hydroxides and water-soluble dyes, a process for their preparation and their use.
  • Double-layer hydroxides are known in the literature, for example from R. Allmann, "Chimia” 24 (1970), p. 99 ff. Chemically, they are mixed basic hydroxyls of divalent and trivalent metal cations.
  • Natural and synthetic double-layer hydroxides continuously give off water when heated or calcined.
  • the crystal water is completely removed at 200 ° C., higher temperatures lead to the elimination of water from the hydroxide structure and of carbon dioxide from the carbonate contained as the usual anion.
  • the structures of the double-layer hydroxides are broken down in this process, the X-ray diffraction diagrams show only broad and less characteristic lines for periclase (MgO). Due to the different composition, also with regard to the water content, line broadening and shifting can be explained in the X-ray diffraction diagram.
  • the processes are reversible: the mixed oxide re-forms the layer connection while absorbing water and anions. At higher temperatures, the unordered mixed oxide finally turns into well crystalline and less reactive products and ultimately into spinel and MgO.
  • EP-A-0 206 798 describes water-insoluble pigments consisting of a complex of a water-insoluble inorganic substrate with anion-exchanging properties, in particular double-layer hydroxides containing magnesium or aluminum, a water-soluble dye and an anionic amphiphilic material.
  • the amphiphilic material is practically organic fatty acids or their salts, as well as sulfonated organic compounds.
  • Synthetic hydrotalcite is mentioned here as a suitable double-layer hydroxide, for example anionic organic dyes as water-soluble dyes.
  • water-insoluble pigments of this type are produced by bringing the pre-formed double-layer hydroxide, the dye and the amphiphilic material into contact with one another in a liquid medium, for example water.
  • the object of the present invention is to provide new water-insoluble pigments based on double-layer hydroxides and water-soluble dyes, which - compared to those of the prior art - are more stable towards chemical and physical ones Influences as well as a higher occupancy density with such dyes.
  • the present invention accordingly relates to new water-insoluble pigments based on double-layer hydroxides and water-soluble dyes, which are characterized in that they are obtained by reacting double-layer hydroxides which form in situ and water-soluble anionic dyes in aqueous or water-containing dyes Media, the double-layer hydroxides forming in situ having the general formula (I)
  • M 111 for at least one trivalent metal cation
  • A for the equivalent of an anion of a mono- or polybasic acid, 1/6 ⁇ x ⁇ 1/2 and 0 ⁇ m ⁇ 1.
  • the pigments according to the invention which are obtained with double-layer hydroxides which form in situ, are distinguished from those Pigments known from the prior art, which are produced by adsorbing the dyes onto pre-formed double-layer hydroxides, obviously have significant structural differences. Surprisingly, it was found that the stability of the pigments according to the invention in the light-fastness test and with respect to oxidizing agents is significantly greater than in the case of the comparable colored double-layer hydroxide pigments of the prior art.
  • the way in which the pigments according to the invention are prepared means that they incorporate a substantially larger amount of anionic dyes into the double-layer structure that forms than the known pigments of the prior art. This property is also characterized below as "higher occupancy density" (see the examples). The differences shown above are all the more surprising since it would actually have been assumed that an already pre-formed double-layer hydroxide should impart the same properties to the pigments as a double-layer hydroxide which forms in situ.
  • a preferred embodiment of the present invention is that in the pigments the divalent metal cation (M ⁇ ) is selected from magnesium, calcium, manganese, iron, cobalt, Nik ⁇ kei, copper, zinc and cadmium, while the trivalent metal cation ( ⁇ 111 ) preferably consists of aluminum or chromium, manganese, iron, cobalt and nickel. If - in connection with the explanation of the general formula (I) - there is talk of at least one divalent or trivalent metal cation, this means that in such double layer hydroxides there may be several divalent or trivalent metal cations in addition to each ⁇ can be present.
  • the anion (A) can also be selected from an abundance of mono- or polybasic acids.
  • Anions include hydroxide, chloride, bromide, iodide, nitrate, chlorate, perchlorate, carbonate, sulfate, thiosulfate, tungstate, chromate and hexacyanoferrate and in principle also a large number of organic anions, for example picrates.
  • pigments based on in-situ double-layer hydroxides which are selected from hydraulic talcite, zinc / aluminum phase, magaldrate and / or pyroaurite.
  • Hydrotalcite is known to be a natural mineral with the ideal shape1
  • hydrotalcite whose structure is derived from that of brucite [Mg (0H) 2 ].
  • the synthesis of hydrotalcite is described, for example, in DE-C-3306822, DE-A-3346943 and DE-A-1592 126.
  • water-soluble, anionic dyes are not critical, since in principle all commercially available or synthetic water-soluble anionic dyes are suitable for the production of pigments.
  • the lower limit of the water solubility of the usable, water-soluble, anionic dyes is 10 mg / 1.
  • water-soluble, organic, anionic dyes are preferred selected from the group of anthraquinone or naphthol dyes.
  • Another object of the present invention is a process for the preparation of the above-mentioned water-insoluble pigments based on double-vision hydroxides and water-soluble dyes.
  • This process is characterized in that double-layer hydroxides which form in situ and water-soluble anionic dyes are reacted with one another in aqueous or water-containing media, the double-layer hydroxides which form in situ having the general formula (I)
  • two possibilities with regard to the in situ forming double-layer hydroxides principle - in the sense of the invention are for carrying out the driving Ve r Embodiment of the process according to the invention is based on the corresponding, previously calcined double-layer hydroxides.
  • the calcination of the double-layer hydroxides produces a disordered mixed oxide, the above-mentioned divalent and trivalent metal cations, with elimination of water, the layer structure of the double-layer hydroxides being degraded (see also the literature cited at the beginning).
  • such a material is referred to as "previously calcined double-layer hydroxide".
  • the structure of the double-layer hydroxides is formed in situ from this mixed oxide structure.
  • This first embodiment of the process according to the invention is therefore characterized in that previously calcined double-layer hydroxides of the general formula (I) are used to form the double-layer hydroxides of the general formula (I) in situ.
  • These previously calcined double-layer hydroxides in powder form or in the form of an aqueous slurry, which may also contain polar organic solvents, are brought into contact, preferably with stirring, with a solution of the anionic, organic dyes.
  • the solids content is then separated from the supernatant solution. It is irrelevant here whether a solution of dyes is added to a suspension of the previously calcined double-layer hydroxides or a suspension of the previously calcined double-layer hydroxides is added to a solution of dyes.
  • Measures to separate the Solids content ie the still moist pigment formed from the supernatant solution, are known in principle to the person skilled in the art. Examples include decanting or filtering.
  • the second process variant of the present invention consists in that the pigments are prepared by in-situ precipitation (also sometimes referred to as flash or conti precipitation) of the double-layer hydroxides in the presence of the anionic dyes.
  • the preferably water-soluble salts of metal cations forming double-layer hydroxides are added to an aqueous or water-containing solution of an anionic dye in the desired stoichiometric ratio and the double-layer hydroxides in the presence of the water-soluble anionic dyes by increasing the pH educated.
  • the double layer hydroxides which form in situ are reacted with the anionic dyes during the flash precipitation in the alkaline range, ie at pH values of> 7, preferably in the pH range from 9 to 13.
  • the Adjustment of the aqueous or water-containing medium to the desired pH takes place, for example, by adding the hydroxides of the metal cations mentioned (M 11 ) and (M 111 ) or by adding alkali metal hydroxides, such as sodium hydroxide.
  • the suspension which forms is stirred and the solids fraction obtained - as described above - is separated from the supernatant solution.
  • the so-called flash precipitation of double-layer hydroxides is generally described in EP-A-0 207 811.
  • the second embodiment of the process according to the invention is therefore characterized in that the in-situ formation of the double-layer hydroxides of the general formula (I) is preferred water-soluble salts of the metal cations (M 11 ) and (M 111 ) are used, the pH of the aqueous or water-containing medium being adjusted to alkaline values, preferably to pH values in the range from 9 to 13.
  • Suitable water-soluble salts of the metal cations (M 11 ) and ( ⁇ I) are in particular the salts of the metal cations mentioned with the anions (A) defined above, but the oxides or hydroxides of these metal cations can also be used according to the invention become.
  • water is the solvent, i.e. as an aqueous medium, suitable for the process according to the invention.
  • the solubility of the water-soluble, anionic dyes can be greatly improved in some cases, in particular by the presence of polar organic solvents, the presence of these solvents is preferred in many cases, so that the pigments are formed in solvent mixtures of water and polar organic solvents, the latter comprising, in particular, short-chain alcohols, preferably methanol, ethanol and / or propanol, and also ketones and here in particular acetone.
  • polar organic solvents comprising, in particular, short-chain alcohols, preferably methanol, ethanol and / or propanol, and also ketones and here in particular acetone.
  • the mixing ratios of water to organic solvents are generally in the range from 5: 1 to 1: 5, preferably in the range from 1: 3 to 3: 1 and in particular 1: 1.
  • the temperature of the reaction of the in-situ double layer hydroxides and dyes is not critical.
  • the reaction is preferably carried out at room temperature, although any temperature between the melting point and the boiling point of the solutions is suitable.
  • the temperature of the solvent can, if appropriate, also be above the normal Boiling point can be increased if this is desirable in special cases for reasons of solubility of the dye.
  • these can be hydrophobized according to processes known per se. This is done in particular by adding sodium salts of fatty acids, as is known in principle from EP-A-0 206 798 for the water-insoluble pigments described there.
  • the pigments are preferably used as color carriers in washing, rinsing and cleaning agents, soaps, cosmetics, lacquers, paints, foods, plastics and polymers.
  • the pigments prepared according to the invention have significantly better physical stability than comparable pigments known from the literature.
  • the pigments were triturated with aluminum oxide and thickened with water to form a spreadable paste. After a longer exposure time with a xenon lamp, there are color differences to the non-exposed areas.
  • the pigments according to the invention show a significantly lower brightening than pigments of the prior art.
  • calcined hydrotalcite is used below, it is generally understood to mean a product which has been produced by heating commercially available hydrotalcite to 500 ° C. in the course of 2 hours (loss of mass approx. 40% by weight).
  • flash-precipitated hydrotalcite is understood to mean a product which has been prepared by in-situ synthesis of the hydrotalcite from the corresponding metal salts.
  • Examples 1 to 6 relate to the production of pigments according to the invention on the basis of hydrocatalcite which forms in situ from previously calcined hydrotalcite, and furthermore their coating density with different anionic dyes. Comparative Examples 1 and 2 show corresponding values for pigments not according to the invention which correspond to the prior art.
  • Examples 7 and 8 relate to the production of pigments according to the invention based on flash-precipitated hydrotalcite and their occupancy density.
  • Examples 9 to 11 show the production of pigments according to the invention on the basis of other double-layer hydroxides which form in situ.
  • Examples 12 to 14 and comparative example 3 relate to the light fastness and oxidation stability of the invention Pigments, again in comparison to pigments of the prior art.
  • Example 15 shows the coating density of pigments according to the invention when using different solvents and example 16 shows the preparation of hydrophobized pigments according to the invention.
  • Table 1 below shows the residual concentrations of dye obtained in the supernatant solution.
  • Residual dye concentration determined photometrically.
  • the deeply colored sample was calcined at 500 ° C for 2 h.
  • a grayish powder remained, which calculated mass loss themselves to 60.6%.
  • the X-ray diffractogram produced showed the lines for calcined hydrotalcite.
  • the pigments according to the invention and comparative samples based on non-calcined hydrotalcite and alizarin sulfonate were ground in a 20% concentration with aluminum oxide and mixed with distilled water to form a spreadable paste. They were then applied to an aluminum oxide film and left to dry at room temperature. In parallel, aqueous dye solutions were spread onto the alumina support as reference samples and also dried. The samples were irradiated with a "sunlight improvisator" in a day / night rhythm.
  • a "Xenotest 150" device, System Cassella, Original Hanau, equipped with a Xenon burner Xe 1500 with the color temperature between 5500 and 6500 ° K prescribed according to DIN 54004 served as the "sunlight improviser".
  • the pigments according to the invention and comparative samples based on non-calcined hydrotalcite - ie cal.HT and HT + Acid Green 41 and flash HT and HT + alizarin sulfonate - were triturated to a pulp with 20% strength with Al 2 03 and a little water and in a thickness of Approx. 1 mm applied to an Al 2 ⁇ 3 film and air-dried.
  • the samples were then exposed to xenon light (see Example 12).
  • the reflective light intensity was measured in percent against a white standard (Ti0 2 , 100%) using a color measuring device.
  • the pigments according to the invention from the reactions of calcined hydrotalcite or the flash precipitation showed significantly lower reflection values than the comparable samples of the reactions with non-calcined hydrotalcite.
  • a clear trend can therefore be seen:
  • the pigments obtained from the reactions with non-calcined hydrotalcite are less color-stable, since the curves (reflection intensity versus time) generally result in larger gradients. This can be seen as a measure of the brightening and thus of the lower light stability.
  • Time dye Alizarin sulfonate Acid Green 41 HT cal. HT HT flash HT
  • Suspensions were prepared from 75 mg of the pigments mentioned in Example 4 in 25 ml of distilled water, and 2% sodium hypochlorite solution was added. The pigments only became lighter after 1 h; after 1.5 h there was still a slight pink color.
  • Example 15 Analogous to Example 14, corresponding suspensions of the pigments from non-calcined hydrotalcite were prepared and the procedure was as above. After 1 h the pigments were already colorless.
  • Example 15 Analogous to Example 14, corresponding suspensions of the pigments from non-calcined hydrotalcite were prepared and the procedure was as above. After 1 h the pigments were already colorless.
  • Table 9 below shows the data on the occupancy density obtained.
  • Suspensions were prepared from 100 mg of the pigments described in Example 4 in 50 ml of distilled water and a solution of 50 mg of sodium oleate in 50 ml of water was added. After stirring at 20 ° C for 30 min, the solids were filtered off and washed. The solids were resuspended in water and about 1/10 of the amount of liquid was mixed with oil. After the samples had been mixed and separated, the total solids content was suspended in the organic phase.

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Abstract

L'invention concerne des pigments insolubles dans l'eau, à base d'hydroxydes à double couche, et des colorants solubles dans l'eau, lesdits pigments étant obtenus par la réaction d'hydroxydes à double couche qui se forment in situ avec des colorants anioniques solubles dans l'eau. L'invention concerne également leurs procédés de production et l'utilisation de ces pigments comme agents chromophores dans des produits de lavage, de rinçage et de nettoyage, dans des savons, des produits cosmétiques, des laques, des peintures, des denrées alimentaires, des matières plastiques et des polymères.
PCT/EP1991/001119 1990-06-26 1991-06-17 Pigments a base d'hydroxydes a double couche, leur procede de production et leur utilisation WO1992000355A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4020272A DE4020272A1 (de) 1990-06-26 1990-06-26 Pigmente auf basis von doppelschicht-hydroxiden, verfahren zu deren herstellung sowie deren verwendung
DEP4020272.0 1990-06-26

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WO1992000355A1 true WO1992000355A1 (fr) 1992-01-09

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0557089A1 (fr) * 1992-02-21 1993-08-25 Unilever Plc Protecteurs solaires contenant des hydroxydes doubles en couche
WO1995005150A1 (fr) * 1993-08-13 1995-02-23 Unilever Plc Agents antisolaires
US5474762A (en) * 1992-02-21 1995-12-12 Chesebrough-Pond's Usa Co. Division Of Conopco, Inc. Sunscreen agents
WO2001004216A1 (fr) * 1999-07-13 2001-01-18 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Pigment colorant
US7425235B2 (en) 2005-02-11 2008-09-16 The Board Of Regents Of The University Of Texas System Color compositions and methods of manufacture
US7429294B2 (en) 2002-06-19 2008-09-30 Board Of Regents, The University Of Texas System Color compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0220578D0 (en) * 2001-12-04 2002-10-09 Unilever Plc Hair treatement composition

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Publication number Priority date Publication date Assignee Title
EP0206800A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation
EP0206796A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation
EP0206798A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206800A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation
EP0206796A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation
EP0206798A2 (fr) * 1985-06-24 1986-12-30 The Dow Chemical Company Pigments insolubles et leur préparation

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0557089A1 (fr) * 1992-02-21 1993-08-25 Unilever Plc Protecteurs solaires contenant des hydroxydes doubles en couche
US5474762A (en) * 1992-02-21 1995-12-12 Chesebrough-Pond's Usa Co. Division Of Conopco, Inc. Sunscreen agents
WO1995005150A1 (fr) * 1993-08-13 1995-02-23 Unilever Plc Agents antisolaires
US5573755A (en) * 1993-08-13 1996-11-12 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Sunscreen agents
WO2001004216A1 (fr) * 1999-07-13 2001-01-18 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Pigment colorant
US6648959B1 (en) 1999-07-13 2003-11-18 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Coloring pigment
US7429294B2 (en) 2002-06-19 2008-09-30 Board Of Regents, The University Of Texas System Color compositions
US7425235B2 (en) 2005-02-11 2008-09-16 The Board Of Regents Of The University Of Texas System Color compositions and methods of manufacture

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