WO1991013125A2 - Colorant - Google Patents

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Publication number
WO1991013125A2
WO1991013125A2 PCT/EP1991/000274 EP9100274W WO9113125A2 WO 1991013125 A2 WO1991013125 A2 WO 1991013125A2 EP 9100274 W EP9100274 W EP 9100274W WO 9113125 A2 WO9113125 A2 WO 9113125A2
Authority
WO
WIPO (PCT)
Prior art keywords
colourant
group
chiral
atoms
replaced
Prior art date
Application number
PCT/EP1991/000274
Other languages
English (en)
Other versions
WO1991013125A3 (fr
Inventor
Ian Charles Sage
Jacqueline Dawn Bailey
Thomas Alan Davies
Original Assignee
MERCK Patent Gesellschaft mit beschränkter Haftung
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by MERCK Patent Gesellschaft mit beschränkter Haftung filed Critical MERCK Patent Gesellschaft mit beschränkter Haftung
Priority to BR919104646A priority Critical patent/BR9104646A/pt
Priority to KR1019910701414A priority patent/KR920701392A/ko
Publication of WO1991013125A2 publication Critical patent/WO1991013125A2/fr
Priority to FI914973A priority patent/FI914973A0/fi
Publication of WO1991013125A3 publication Critical patent/WO1991013125A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/36—Steroidal liquid crystal compounds
    • 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
    • A61K8/0295—Liquid crystals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/36—Pearl essence, e.g. coatings containing platelet-like pigments for pearl lustre
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • 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
    • A61K2800/436—Interference pigments, e.g. Iridescent, Pearlescent

Definitions

  • the invention relates to a colourant based on platelet- shaped substances optionally coated with one or more metal oxides, characterized in that it contains a chiral iridescent liquid crystalline medium.
  • cosmetics had a disadvantage that they are sticky because of their high oil contents. If therefore, in order to reduce this stickiness, for example, a semi-solid component such as wax etc. is increased, although the stickiness is improved, spreading becomes more difficult, and in
  • Japanese Laid-open Patent Application No. 56115/1986 discloses an example which contains an organically modified montmorillonite clay and a dextrin fatty acid ester and/or a lyophilic sugar fatty acid ester
  • Japanese Laid-open Patent Application No. 67514/1984 discloses an example which contains a polyalcohol and a resin, but in every case, the amount of the gelling agent incorporated was great, therefore, when the gel strength was enhanced, there were problems, for example, spreading was difficult and it became sticky. Further, for those compositions using organic solvents, there is a problem concerning safety.
  • Swiss Patent Application CH 491 533 discloses that micro-encapsulated cholesteric liquid crystals can be used in aqueous suspension as colourants for decorative applications.
  • colourants based on platelet shaped substances optionally coated with one or more metal oxides containing a chiral iridescent liquid crystalline medium solve the above-described problems.
  • skin-friendly preparations can thereby be obtained providing a coloured cosmetic formulation which is highly safe to the skin, has sufficient high gel strength, good dispersion of the pigment, is good at spreading and application feel and has an anti- crinkle effect and a moisture-retaining effect.
  • the present invention relates to a dye-stuff based on platelet-shaped substances optionally coated with one or more metal oxides, characterized in that it contains a chiral iridescent liquid crystalline medium; in particular to such a colourant wherein a) the chiral iridescent liquid crystalline medium is linked to the surface of the platelet-shaped substrate, b) the chiral iridescent liquid crystalline medium is
  • At least one chiral component is a compound of the formula I R 1 -(A 1 -Z 1 -) m -A 2 -R* I wherein R 1 is R* or an alkyl radical or an alkenyl radical
  • CN or at least one halogen atom, wherein one or two non-adjacent CH 2 groups of these radicals can also be replaced by -O-, -CO-, -O-CO- and/or -CO-O-,
  • a 2 are in each case independently of one another a) a 1,4-cyclohexylene group, wherein one or
  • two non-adjacent CH 2 groups can also be re- placed by -O- and/or -S- and/or which can be substituted in the 1-position by a CN- or CH 3 -group, b) a 1,4-cyclohexenylene, a piperidine-1,4-diyl or 1,4-bicyclo[2,2,2]octylene group, or c) a 1,4-phenylene group optionally substituted by one or two F-atoms or one or two CN- or one or two CH 3 -groups, wherein at least one CH group can also be replaced by N,
  • n 0 , 1 , 2 or 3 , and
  • R* is a chiral radical imparting optical activity to the compound of the formula I, or a chiral steroid ester of the formula II
  • Ster denotes a saturated or unsaturated gonan-3-yl group being optionally substituted by up to 6 normal or branched alkyl residues with 1 to 10 C atoms.
  • R* is a chiral radical of the formula III
  • X is ⁇ or CH 3
  • Y is F, Cl, Br, CN, CF 3 or CH 3 in the case that
  • R° is an alkyl radical being different from X with up to 14 C atoms, wherein one or two non-adjacent
  • CH 2 groups may be replaced by -O-, -CO-O- or -O-CO- at least one non-chiral compound is a compound of the formula IV
  • alkyl radical or an alkenyl radical each with up to 18 C atoms optionally substituted by CN or at least one halogen atom, wherein one or two non adjacent CH 2 groups of these radicals can also be replaced by -O-, -CO-, -O-CO- and/or -CO-O-, one of
  • R 2 and R 4 may also be CN or halogen, A 3 , A 4
  • one or two non-adjacent CH 2 groups can also be replaced by -O- and/or -S- and/or which can be substituted in the 1-position by a CH 3 - or CN-group, b) a 1,4-cyclohexenylene, a piperidine- 1,4-diyl or 1,4-bicyclo[2,2,2]octylene group, or c) a 1,4-phenylene group optionally substituted by one or two F atoms or
  • Z 2 and Z 3 are each -CO-O-, -O-CO-, -CH 2 CH 2 -, -CHCH-CH 2 -,
  • the platelet-shaped substrate is mica
  • the mica is coated by one or more metal oxides
  • the metal oxide is at least one group II, III, IV, V
  • the invention relates to
  • a coloured printing ink composition wherein the colourant is based on platelet-shaped substances optionally coated
  • present invention are such having 1.0 x 10 -5 mol/g or
  • Particularly preferred platelet-shaped substances are mica coated with one or more metal oxides as, for example, titanium dioxide, iron oxide, chromium oxide, bismuth oxide.
  • Particularly preferred are pearl lustre pigments distributed by E. Herck, Darmstadt, FRG, under the tradename Iriodin ® .
  • a hydrophobic layer is applied to the plateletshaped substances before admixing them with the chiral iridescent liquid crystalline media.
  • the colourant according to the invention contains 0.1-50 % by weight, preferably 0.5-10 %, of the platelet shaped substances and 50 %-99.9 % by weight, preferably 90 %-99.5 % of the chiral iridescent liquid crystal medium.
  • the platelet shaped substance can be treated, for example, with dialkylphosphoric acid as in the case of mica described in Japanese Patent Application JP 63 238 Oil, with mono- alkoxytitanates as in the case of mica described in
  • the platelet shaped substance may be treated with a Werner type surface active transition metal complex such as stearato chromic chlorid as described in Advances in Chemistry Series, Volume 23 (1959) pp 338-346.
  • the platelet shaped substance may be treated with an active silicone derivative such as poly hydrogen methyl siloxane to obtain a hydrophobic surface.
  • liquid crystal phases There are two important types of liquid crystal phases; the smectic mesophase in which the long range ordering is of a substantially lamellar type and the nematic mesophase in which the ordering is substantially linear,
  • the molecules tend to line up with the long axes of the molecules parallel.
  • cholesteric mesophase Included sometimes as a subclass of the nematic mesophase and sometimes classified as a separate mesophase is the cholesteric mesophase.
  • the latter has a helical long
  • the helical twist is determined by the nature and extent of the optical activity.
  • the pitch of the helical twist may be such that thin films of the cholesteric phase reflect visible light, resulting in the observation of bright colours.
  • the colourants according to the invention have not only a high refractive index and high gloss but also a very good skin feeling and an anti-crinkle effect.
  • R 1 , R 2 , R 3 , R 4 , R*, R o , A 1 , A 2 , A 3 , A 5 , Z 1 , Z 2 , Z 3 , Q, X, Y, m and p have the meaning given, unless expressly indicated otherwise.
  • the compounds of the formula I include preferred compounds with one ring of the sub-formula la
  • R 1 -A 1 -Z 1 -A 2 -R* Ic compounds with three rings of the sub-formulae Id to Ig R 1 -A 1 -A 1 -A 2 -R* Id
  • R 1 denotes preferably alkyl or alkpxy.
  • a 1 and A 2 preferably denote a 1,4-phenylene, group optionally substituted by a halogen atom, preferably by fluorine, or a pyrimidine-2,5-diyl group or a 1,4-cyclohexylene group.
  • the compounds of the sub-formulae la, lb and Ic are particularly preferred, in particular those compounds of the formula la wherein R 1 is R*.
  • the achiral compounds of the formula IV include preferred compounds with two rings of the sub-formulae IVa to IVb
  • R 2 -A 4 -Z 3 -A 5 -R 4 IVb compounds with three rings of the sub-formulae IVc to IVf
  • a 3 , A 4 and A 5 have the same preferred meaning as given for A 1 and A 2 for the compounds of the formula I.
  • R 1 , R 2 and R 4 each preferably denote alkyl with preferably 1 to 13 C atoms, particularly 3 to 12 C atoms, wherein one or the two CEL groups may be replaced by -O- or -CO-.
  • R 1 , R 2 and R 4 each are an alkyl radical wherein one ("alkoxy” or “oxaalkyl”) or two ("alkoxyalkoxy" or
  • dioxaalkyl nonadjacent CH 2 groups may be replaced by -O-, these radicals can be straight-chained or branched. Preferably, they are straight-chained and have 2, 3, 4, 5, 6, 7, 8, 9 or 10 C atoms and are accordingly preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl,
  • nonyl or decyl ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, nonyloxy, decyloxy, also methyl, undecyl, dodecyl, tridecyl, tetradecyl, methoxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
  • 1,3-, 1,4-, 2,4-dioxapentyl 1,3-, 1,4-, 1,5-, 2,4-, 2,5- or 3,5-dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- or 4,6-dioxaheptyl.
  • chiral steroid esters of the formula II used according the invention are also known per se, for example from pessigkristalle in Tabellen, VEB Deutscher Verlag fur Grundstoff- industrie, Leipzig Vol. I 1974 and Vol. II, 1984.
  • Ster denotes a saturated or unsaturated gonan-3-yl group of the formula
  • cholesterin-3-yl group are preferred.
  • Ster denotes a cholestan-3-yl group, a cholest-2- en-3-yl group, a sitosterin-3-yl group, an 17-alkylan- drostan-3-yl group, an 17-alkylandrosten-3-yl group or
  • the residue R 3 of the formula II preferably is an alkyl
  • the invention thus relates preferably to dye-stuffs based on platelet-shaped substances containing a chiral iridescent liquid crystalline medium comprising compounds of the formula I, in particular compounds of the formula I wherein R* is a chiral radical of the formula III
  • Y denotes preferably CH-, Cl, CN or F
  • Q denotes preferably an alkylene residue with up
  • R o denotes preferably an alkyl radical with 2 to
  • the compounds of the formulae I, II and IV preferably contain at least one, more preferred two or more, non-chiral compounds of the formula IV and at least one, preferably two, three or more, chiral esters of the formula I or II.
  • Said coloured liquid crystalline phases contain about 20 %- 90 %, preferably 35 %-80 %, of one or more compounds of the formula I or II and about 10 %-80 %, preferably 20 %-65 %, of one or more compounds of the formula IV.
  • the clearing point of these chiral iridescent liquid crystalline phases lies preferably between 37 ° and 100 °C, particularly preferred between 50 °C and 90 °C.
  • the chiral iridescent liquid crystalline phases used in the present invention are prepared in a manner which is
  • the components are dissolved in one another, preferably at elevated temperature. Because of the good gloss and the low weight of the
  • inventive colourant only relatively small amounts thereof are required in decorative compositions.
  • absolute amount depends on the nature of the formulation and the desired colour effect, as a rule about 1 %-50 %, by weight of the colourant preferably 5 %-20 % are employed.
  • the chiral iridescent liquid crystalline phases may be microencapsulated after admixing to platelet shaped substances.
  • microencapsulated chiral iridescent liquid crystalline phases are prepared in a manner which is customary per se (For example U.S. Patent 2,800,457).
  • the colourants according to the invention can be employed in decorative formulation for technical or cosmetic applications preferably for cosmetic applications.
  • Vehicles used for the cosmetic formulations according to the invention are the substances customary for, for example, lipsticks, grease sticks, creams, powders and other
  • Preferred vehicles are, for example, water based binders like polyvinyl alcoholes or polyurethanes.
  • Preferred vehicles for use in formulations are those
  • the formulations according to the invention contain as colouring constituents in each case at least one of the abovementioned dye-stuffs based on platelet-shaped substances which are coated with chiral iridescent liquid crystalline media formed by the compounds of the formulae I or II and the compounds of the formula IV.
  • the present invention therefore provides very advantageous coloured compositions with very attractive colour effects
  • Example 1 nematic phase, Ch: cholesteric phase, I: isotropic phase. The figure between two symbols indicates the transition temperature.
  • Example 1 nematic phase, Ch: cholesteric phase, I: isotropic phase. The figure between two symbols indicates the transition temperature.
  • a cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 49.3 %
  • a cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 44.5 %
  • a cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 41.0 %
  • cholesteryl propionate 10.2 % exhibits a bright, blue colour and Ch 55.6 ° I
  • Example 5 A cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 40.0 %
  • a cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 40.0 %
  • a cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 38.0 %
  • cholesteryl propinate 11.4 % exhibits a bright, purple colour and Ch 56.8 ° I
  • Example 7 A cholesteric liquid crystalline mixture is formulated containing the following liquid crystalline components p-pentylphenyl-p-methoxybenzoate 18.0 %
  • examples 1 to 7 are admixed to surface-modified ( as described in Example 8 ) mica pigments to achieve decorative compositions with attractive coloured effects , pleasant skin feeling and anti-crinkle effect .
  • thermochromic liquid crystalline medium to a mica pigment.
  • Edoran ® a solution of tetrachloro- ⁇ -hydroxo- ⁇ -stearatodichromo complex, which is available from Mitsubishi Gas Chemical Co. Limited, Tokyo, Japan
  • distilled water a concentration of 3 % solids in distilled water
  • Black Pearl TM Particle Size ⁇ 15 ⁇ m/available from E. Merck, 6100 Darmstadt, FRG
  • Sufficient of the solution is added to provide a mobile slurry, which is stirred at room temperature for 30 minutes. After this period, the suspension is filtered on a Buchner funnel, rinsed once with water and dried in a vacuum oven at 40 °C overnight.
  • the treated mica is mixed into the chiral liquid crystal mixture of example 3 at a concentration of 1 % by weight to provide a bright iridescent colourant.
  • a concentration of 1 % by weight to provide a bright iridescent colourant.
  • Carbopol 940 a water soluble copolymer of acrylic acid crosslinked with a polyalkenylpoly- ether, which is available from BF Goodrich Co, Cleveland, Ohio
  • a 0.25 % by weight solution of Carbopol 940 a water soluble copolymer of acrylic acid crosslinked with a polyalkenylpoly- ether, which is available from BF Goodrich Co, Cleveland, Ohio
  • a clear highly viscous gel is formed.
  • strands of colourant (of example 8) are injected into the gel to obtain an attractive cosmetic formulation having an iridescent colour effect in the bulk sample, and a pleasant smooth feeling when applied to the skin.
  • the colourant of example 8 is emulsified into an aqueous solution of gelatin, and microencapsulated in gelatin-gum acacia coacervate according to the process of USP 2800457 example 2.
  • the capsules are hardened by the process of
  • USP 2800457 example 1 A slurry of microcapsules of mean diameter 18 ⁇ m is obtained, and added to an aqueous solution of polyvinyl alcohol (PVA) to obtain a viscous suspension containing 8 % PVA and 20 % liquid crystal. The suspension is applied by screenprinting to a plain board, to give a bright iridescent colour effect without a separate black layer being required.
  • PVA polyvinyl alcohol
  • a blue colourant is obtained by substituting a composition of example 5 for the liquid crystal in example 8.
  • the colourant is incorporated into a mascara formulation according to UK Patent Application GB 89 10803.9 example 9 and provides enhanced colour brightness and contrast over that composition.
  • thermochromic ink formulation commerciany available from Merck Ltd.
  • TCJ1005 50 g
  • thermochromic ink commercially available from Merck Ltd.
  • lamellar molybdenum sulphide 2 g
  • molybdenum sulphide was ommitted, and an aluminium flake pigment, BASF type EM-21-3157 was used in its place. Prior to use of the pigment, it was freed of oily material by washing twice with five weights of tetrahydrofuran, and dried at 40 degrees C for 24 hours under vacuum. The resulting coating gave a spectacular flop effect, with metallic specular reflection close to normal incidence giving way to a thermochromic colour play at glancing angles.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Cosmetics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Liquid Crystal Substances (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention se rapporte à un colorant à base de substances en forme de plaquettes recouvertes facultativmeent d'un ou plusieurs oxydes métalliques, qui contient un milieu cristallin liquide iridescent et que l'on peut utiliser pour la coloration de peintures, de plastiques, de fibres, de verres, de produits cosmétiques et d'encres d'imprimerie ou comme matière tinctoriale destinée aux colorants pour cheveux.
PCT/EP1991/000274 1990-02-23 1991-02-13 Colorant WO1991013125A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR919104646A BR9104646A (pt) 1990-02-23 1991-02-13 Corante
KR1019910701414A KR920701392A (ko) 1990-02-23 1991-02-13 착색제
FI914973A FI914973A0 (fi) 1990-02-23 1991-10-22 Faergaemne.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909004161A GB9004161D0 (en) 1990-02-23 1990-02-23 Colourant
GB9004161.7 1990-02-23

Publications (2)

Publication Number Publication Date
WO1991013125A2 true WO1991013125A2 (fr) 1991-09-05
WO1991013125A3 WO1991013125A3 (fr) 1991-10-31

Family

ID=10671540

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/000274 WO1991013125A2 (fr) 1990-02-23 1991-02-13 Colorant

Country Status (8)

Country Link
EP (1) EP0471046A1 (fr)
JP (1) JPH04507116A (fr)
KR (1) KR920701392A (fr)
AU (1) AU7239091A (fr)
BR (1) BR9104646A (fr)
FI (1) FI914973A0 (fr)
GB (1) GB9004161D0 (fr)
WO (1) WO1991013125A2 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5194183A (en) * 1988-09-09 1993-03-16 Akzo N.V. Thermochromic effect coating
WO1993012195A1 (fr) * 1991-12-09 1993-06-24 MERCK Patent Gesellschaft mit beschränkter Haftung Pigment a effet thermochromique et son procede de production
US5242617A (en) * 1989-02-13 1993-09-07 Akzo N.V. Liquid crystal pigment, method of producing and use in coatings
WO1994022976A1 (fr) * 1993-04-05 1994-10-13 Central Research Laboratories Limited Preparation optique
WO1995008786A1 (fr) * 1993-09-22 1995-03-30 Central Research Laboratories Limited Materiau colore
WO1995029961A1 (fr) * 1994-04-30 1995-11-09 Wacker Chemie Gmbh Compositions de revetement dont la couleur perçue depend de l'angle d'observation, et utilisation des telles compositions dans des peintures de base pour revetements de peinture multicouches
WO1995029962A1 (fr) * 1994-04-30 1995-11-09 Wacker-Chemie Gmbh Produit de revetement aqueux et procede permettant de realiser des revetements de peinture multicouches dont la couleur perçue depend de l'angle d'observation
WO1995032247A1 (fr) * 1994-05-24 1995-11-30 Daimler-Benz Aktiengesellschaft Laque fantaisie et laquage fantaisie, notamment de carrosseries de vehicules, au moyen de pigments d'interference a cristaux liquides
FR2777178A1 (fr) * 1998-04-10 1999-10-15 Oreal Kit de maquillage associant un pigment goniochromatique et un pigment monocolore ayant une des couleurs du pigment goniochromatique, ses utilisations
WO2001005932A1 (fr) * 1999-07-17 2001-01-25 Rhodia Consumer Specialties Limited Systèmes surfactant structurés
US6325995B1 (en) 1992-09-21 2001-12-04 The Procter & Gamble Company Lipsticks compositions containing association structures
DE10219296A1 (de) * 2002-04-25 2003-11-20 Coty Bv Temperaturabhängiges Mascara
FR2932982A1 (fr) * 2008-06-26 2010-01-01 Oreal Composition cosmetique a base de cristaux liquides

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001029878A (ja) * 1999-07-27 2001-02-06 Takeuchi Kogyo Kk 塗装体
JP2001311079A (ja) * 2000-04-27 2001-11-09 Kyodo Printing Co Ltd 液晶マイクロカプセル及び記録表示媒体
JP6213973B2 (ja) * 2011-10-06 2017-10-18 御木本製薬株式会社 組成物

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JPS6216408A (ja) * 1985-07-12 1987-01-24 Shiseido Co Ltd 化粧料
EP0383376A1 (fr) * 1989-02-13 1990-08-22 Akzo Nobel N.V. Pigment de cristal liquide, méthode de fabrication et utilisation dans les revêtements
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JPS591407A (ja) * 1983-06-02 1984-01-06 Kao Corp 分岐脂肪酸コレステリルエステルを含有する化粧料
JPS6216408A (ja) * 1985-07-12 1987-01-24 Shiseido Co Ltd 化粧料
EP0383376A1 (fr) * 1989-02-13 1990-08-22 Akzo Nobel N.V. Pigment de cristal liquide, méthode de fabrication et utilisation dans les revêtements
WO1990013282A2 (fr) * 1989-05-11 1990-11-15 MERCK Patent Gesellschaft mit beschränkter Haftung Compositions cosmetiques

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Cited By (19)

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US5194183A (en) * 1988-09-09 1993-03-16 Akzo N.V. Thermochromic effect coating
US5242617A (en) * 1989-02-13 1993-09-07 Akzo N.V. Liquid crystal pigment, method of producing and use in coatings
US5690857A (en) * 1991-12-09 1997-11-25 Merck Patent Gesellschaft Mit Beschrankter Haftung Thermochromic effect pigment and process for producing the same
WO1993012195A1 (fr) * 1991-12-09 1993-06-24 MERCK Patent Gesellschaft mit beschränkter Haftung Pigment a effet thermochromique et son procede de production
US6325995B1 (en) 1992-09-21 2001-12-04 The Procter & Gamble Company Lipsticks compositions containing association structures
WO1994022976A1 (fr) * 1993-04-05 1994-10-13 Central Research Laboratories Limited Preparation optique
WO1995008786A1 (fr) * 1993-09-22 1995-03-30 Central Research Laboratories Limited Materiau colore
US5807497A (en) * 1994-03-24 1998-09-15 Daimler-Benz Ag Effect coating material and effect coating system, especially for vehicle bodies, using liquid-crystalline interference pigments
WO1995029962A1 (fr) * 1994-04-30 1995-11-09 Wacker-Chemie Gmbh Produit de revetement aqueux et procede permettant de realiser des revetements de peinture multicouches dont la couleur perçue depend de l'angle d'observation
WO1995029961A1 (fr) * 1994-04-30 1995-11-09 Wacker Chemie Gmbh Compositions de revetement dont la couleur perçue depend de l'angle d'observation, et utilisation des telles compositions dans des peintures de base pour revetements de peinture multicouches
WO1995032247A1 (fr) * 1994-05-24 1995-11-30 Daimler-Benz Aktiengesellschaft Laque fantaisie et laquage fantaisie, notamment de carrosseries de vehicules, au moyen de pigments d'interference a cristaux liquides
FR2777178A1 (fr) * 1998-04-10 1999-10-15 Oreal Kit de maquillage associant un pigment goniochromatique et un pigment monocolore ayant une des couleurs du pigment goniochromatique, ses utilisations
EP0953330A2 (fr) * 1998-04-10 1999-11-03 L'oreal Kit de maquillage associant un pigment goniochromatique et un pigment monocolore ayant une des couleurs du pigment goniochromatique, ses utilisations
EP0953330A3 (fr) * 1998-04-10 2000-03-01 L'oreal Kit de maquillage associant un pigment goniochromatique et un pigment monocolore ayant une des couleurs du pigment goniochromatique, ses utilisations
US6451294B1 (en) 1998-04-10 2002-09-17 L'oreal Method and makeup kit containing goniochromatic and monochromatic pigments
WO2001005932A1 (fr) * 1999-07-17 2001-01-25 Rhodia Consumer Specialties Limited Systèmes surfactant structurés
DE10219296A1 (de) * 2002-04-25 2003-11-20 Coty Bv Temperaturabhängiges Mascara
DE10219296B4 (de) * 2002-04-25 2013-08-08 Coty B.V. Temperaturabhängiger Mascara
FR2932982A1 (fr) * 2008-06-26 2010-01-01 Oreal Composition cosmetique a base de cristaux liquides

Also Published As

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AU7239091A (en) 1991-09-18
JPH04507116A (ja) 1992-12-10
BR9104646A (pt) 1992-03-24
FI914973A0 (fi) 1991-10-22
KR920701392A (ko) 1992-08-11
WO1991013125A3 (fr) 1991-10-31
EP0471046A1 (fr) 1992-02-19
GB9004161D0 (en) 1990-04-18

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