WO2005000856A2 - Composes de siloxane - Google Patents

Composes de siloxane Download PDF

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Publication number
WO2005000856A2
WO2005000856A2 PCT/EP2004/011021 EP2004011021W WO2005000856A2 WO 2005000856 A2 WO2005000856 A2 WO 2005000856A2 EP 2004011021 W EP2004011021 W EP 2004011021W WO 2005000856 A2 WO2005000856 A2 WO 2005000856A2
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WO
WIPO (PCT)
Prior art keywords
siloxane
group
silicon
siloxane compound
denotes
Prior art date
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PCT/EP2004/011021
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WO2005000856A3 (fr
Inventor
Derek William Butler
Virginie Françoise Marie Juliette CAPRASSE
Iain Alasdair Mackinnon
Grainne M. Moloney
Isabelle Van Reeth
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Dow Silicones Corp
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Dow Corning Corp
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences

Definitions

  • the present invention relates to a siloxane compound having aryl substituents and in particular a siloxane polymer having a high refractive index.
  • the invention relates especially to a siloxane polymer having at least one substituent containing two aryl groups substituted on one and the same carbon atom.
  • the invention also provides in another aspect a process for making such siloxane compounds, and in yet another aspect, cosmetic skin and hair care compositions comprising siloxane compounds.
  • Aryl substituted siloxane compounds have been known for some time, and have been disclosed widely.
  • Aryl substituted siloxane compounds having a relatively high refractive index are also known, and are disclosed for example in patent specifications WO 99/52965, WO 00/27348 and EP 554340.
  • ⁇ denotes an aromatic group having 6 carbon atoms
  • R# denotes hydrogen or methyl
  • R'l to R'5 are independently hydrogen, methyl, fluorine, chlorine or bromine.
  • Particular examples include styrene, alpha-methyl styrene, alpha-methyl styrene dimer and pentafluorobenzene.
  • WO 00/27348 describes for example aralkyl siloxanes of the formula
  • R to R ⁇ and R 8 to RlO are each independently hydrogen, alkyl, halo alkyl, aryl or aralkyl
  • R ⁇ and R 7 are each independently hydrogen, alkyl, halo alkyl or aryl
  • n ' and m ' are each independently integers from 0 to 6, provided (n '+m are > 1 and provided at least one substituent group is aralkyl.
  • EP544330 describes an organosilicon compound of the general formula
  • These materials are suggested as optical matching oils with a refractive index of from 1.46 to 1.51.
  • the current invention provides a siloxane compound having at least 2 silicon atoms linked by oxygen and at least one silicon-bonded substituent of the general formula -(O) x R'- ⁇ 2 wherein R' denotes a divalent hydrocarbon radical, x has a value of 0 or 1 and each ⁇ independently denotes a potentially substituted aryl group, and wherein both potentially substituted aryl groups are linked directly to one and the same carbon atom in the R' group, except that when only one group -(O) x R'- ⁇ 2 is present in the siloxane, either the siloxane contains at least 3 silicon atoms or if only 2 silicon atoms are present, R' equals dimethylene.
  • Siloxane compounds according to the present invention have at least 2 silicon atoms, linked by an oxygen atom. They may be linear or cyclic materials, having the general formula -[R 2 SiO] m - or R3SiO-[R SiO] n -SiR3 wherein n denotes 0 or an integer, m denotes an integer from 3 to 20 and each R denotes a substituent, preferably selected from hydrocarbon, hydrocarbonoxy, hydroxyl or hydrogen, provided at least one silicon-bonded substituent R has the general formula -(O) x R'- ⁇ 2 as defined above. It is possible that in addition to the groups R as defined above, some other R groups are present, which are discussed below as capping groups.
  • m has a value of 3 to 8, most preferably a value of 4 or 5. It is, however, most preferred that the siloxane compound is a linear siloxane where n has a value of 0 or an integer from 1 to 5, especially a value of 0 or 1.
  • the silicon-bonded substituent -(O) x R'- ⁇ is present on at least one silicon atom of the siloxane compound. It is preferred that at least 2 silicon atoms have such substituent, and particularly preferred are siloxane compounds having on each silicon atom such substituent. It is not preferred that more than one such substituent is present on any silicon atom, and indeed it would be difficult to manufacture such compounds for reasons of steric hindrance of these relatively bulky substituents, due to the presence of aryl groups.
  • the group R' is a divalent hydrocarbon group preferably having from 1 to 20 carbon atoms, more preferably 2 to 5, most preferably 2 or 3 carbon atoms.
  • This hydrocarbon group is preferably saturated, and most preferably a linear alkylene group.
  • suitable R' groups are dimethylene, propylene, isopropylene, butylene and isobutylene groups. It is particularly preferred that x has a value of 0, this making the substituent link to the silicon atoms via a Si-C bond. This is preferred, as some greater hydrolytic stability is believed to be achieved compared to Si-O-C bonding.
  • Each group ⁇ is independently selected from optionally substituted aryl groups, preferably having from 6 to 20 carbon atoms. The ⁇ groups include phenyl and substituted phenyls, naphthyl and substituted naphthyl, anthracyl and phenantryl and their substituted derivatives.
  • Suitable substituents of the aryl group include halogen, hydroxyl, alkyl, alkoxy, aryl, aralkyl and carboxyl.
  • suitable groups ⁇ include phenyl, monochlorophenyl, pentachlorophenyl, tri-bromophenyl, tolyl, xylyl, xenyl, cumenyl, mesityl, diphenyl, benzyl acid and benzyl alcohol. More preferred as aryl groups are those who have from 6 to 9 carbon atoms, especially unsubstituted phenyl.
  • the group(s) ⁇ may be linked to any of the carbon atoms of the R' group, although preferably both ⁇ groups are linked to the terminal carbon atom of the R' group, i.e. the one furthest from the silicon atom. It is however essential that both ⁇ groups are substituted onto the same carbon atom of the R' group. This was also found to provide the best refractive index characteristics.
  • siloxane contains at least 3 silicon atoms.
  • siloxanes having only one group -(O) x R'- ⁇ 2 where the siloxane is a disiloxane R' equals dimethylene.
  • the other substituents on the silicon atoms of the siloxane compound may be selected from hydrogen, hydroxyl or hydrocarbyl groups or capping groups. It is preferred that the majority of these other substituents are hydrocarbyl groups, more preferably alkyl groups, most preferably alkyl groups having from 1 to 8 carbon atoms. Particularly preferred are methyl groups or ethyl groups. It is most preferred that at least 80%, ideally substantially all non -(O) x R'- ⁇ 2 substituents are methyl groups.
  • One ore more capping groups may be present on the silicon atoms. They are usually provided as a result of reacting any remaining silicon-bonded reactive groups, preferably Si-H groups, which have not already been substituted with the -(O) x R'- ⁇ 2 groups.
  • the capping groups may be any which will react with the residual silicon-bonded reactive groups, for example aliphatic, cycloaliphatic or aralkyl alcohols, unsaturated alkene, arylene, alkarylene or aralkylene groups, which may be substituted e.g. by ether functionalities.
  • Suitable alcohols include ethanol, hexanol, benzyl alcohol, cyclohexanol, branched alkyl fatty alcohols, styrene, allyloxyethanol and vinyloxyethanol. It is preferred to use capping agents which contain an aryl group, especially where the aim is to maintain a high refractive index value for the siloxane compound. Particularly preferred for such applications is benzyl alcohol.
  • the capping agent may be reacted with the siloxane compound such that it forms a Si-C link, which would be achieved e.g. by hydrosilylation of SiH with an alkenyl group, or a Si-OC link, which would be achieved by condensation of Si- OH or SiH with an alcohol or ether functionality, providing a side product of water or hydrogen gas.
  • the group ⁇ is according to the preferred denotation indicated above, preferably phenyl.
  • This material has been found particularly effective in providing a high refractive index.
  • the number of aryl groups in the siloxane compound according to the invention is at least the same as the number of non-aryl containing silicon-bonded substituents.
  • the ratio of aryl groups to non-aryl containing silicon-bonded substituents is 1/1 (i.e. 4 ⁇ groups and 4 methyl groups).
  • siloxane compounds having a high refractive index are those siloxane compounds in which the carbon content due to aryl groups in the siloxane compound amounts to at least 60% by weight, more preferably at least 70 or 75% by weight of the total carbon content of the siloxane compound, hi the above exemplified preferred disiloxane material of the previous paragraph, this is 24 carbon atoms out a total of 32, or 75%.
  • silanes having silicon- bonded hydroxyl, halogen or alkoxy groups wherein at least one of the silanes has at least one silicon-bonded -(O) x R'- ⁇ 2 substituent, as defined above.
  • All silanes used maybe ones having a silicon-bonded -(O) x R'- ⁇ 2 substituent, resulting in a siloxane compound having such substituents on each silicon atom in the compound.
  • other silanes may be used, with which the silanes having at least one silicon-bonded -(O) x R'- ⁇ 2 substituent, are condensed or reacted.
  • the silanes to be used require at least one condensable or reactive group, if a disiloxane compound is to be made, for example a silicon-bonded hydroxyl group or a silicon-bonded chlorine atom.
  • a siloxane compound is to be made having more than two silicon atoms
  • the above silanes are preferably reacted with other silanes having at least two condensable or reactive substituent, for example a silane with two silicon-bonded hydroxyl groups or two silicon-bonded halogen atoms, e.g. chlorine. It is particularly useful in such reaction to start from an appropriate mixture of chlorosilanes, which are readily hydrolysed and condensed according to known processes.
  • condensation reaction may be carried out in the presence of suitable catalysts such as organic metal compounds such as organotin salts, titanates, or titanium chelates or complexes. Generally, these catalysts are used in amounts of between about 0.001 and 10 wt. % based on the weight of the reagent silanes or oligomers.
  • a hydrosilane for example monochlorodimethylhydrosilane of dichloromonomethylhydrosilane, or hydrosiloxane oligomers
  • R" is a monovalent hydrocarbon group having aliphatic unsaturation, preferably olefinic unsaturation and most preferably in the terminal carbon-carbon bond.
  • Preferred groups R" include Cj.g groups with olefinic unsaturation, for example vinyl or allyl groups.
  • the most preferred material bis diphenylethyl tetramethyl disiloxane may accordingly be prepared from its chlorosilane analogue by reaction of 1,1-diphenylethene with dimethylchlorosilane and subsequent hydrolysis to yield the disiloxane.
  • One benefit of this route is that the chlorosilane adduct can be purified by distillation to remove any residual traces of the platinum complex used in the hydrosilylation process, resulting in water- white materials. Very low residual monomer levels can also be achieved by selection of the distillation conditions to yield adduct of purity in excess of 99.99%.
  • a more preferred synthesis method for the more preferred siloxane compounds according to the invention is the hydrosilylation of a hydrosiloxane compound with a compound of the formula R"- ⁇ 2 group, wherein R" is as defined above, including definition of the preferred groups R" in the presence of a hydrosilylation catalyst.
  • the invention provides in a second aspect a process for making siloxane compounds according to the invention by reacting in the presence of a hydrosilylation catalyst a siloxane compound having at least 2 silicon atoms linked by oxygen and having at least one silicon-bonded hydrogen atom with a compound of the formula R"- ⁇ wherein R" is a monovalent hydrocarbon group having aliphatic unsaturation and each ⁇ independently denotes a potentially substituted aryl group, and wherein both potentially substituted aryl groups are linked directly to one and the same carbon atom in the R" group.
  • Siloxane compounds for use as reagent in the process according to the present invention have at least 2 silicon atoms, linked by an oxygen atom. They may be linear or cyclic materials, having the general formula -[R 2 SiO] m - or R3SiO-[R 2 SiO] n -SiR3 wherein n denotes an integer or 0, m denotes an integer from 3 to 20 and each R denotes a substituent, preferably selected from hydrocarbon, hydroxyl or hydrogen, provided at least one silicon- bonded substituent is a hydrogen atom. It is particularly preferred that m has a value of 3 to 8, most preferably 4 or 5.
  • the siloxane compound is a linear siloxane where n has a value of 0 or an integer, preferably from 1 to 5, especially 0 or 1.
  • the silicon-bonded hydrogen atom is present on at least one silicon atom of the reagent siloxane compound. It is preferred that at least 2 silicon atoms have a hydrogen substituent, and particularly preferred are siloxane compounds having on each silicon atom such hydrogen substituent. Although it is possible to use siloxane reagent compounds with more than one hydrogen substituent on any silicon atom, this is not preferred. It would be unlikely that more than one such hydrogen atom be reacted with the other more bulky reagent R"- ⁇ 2 in view of steric hindrance.
  • the other substituents on the silicon atoms of the reagent siloxane compound may be selected from hydroxyl or hydrocarbyl groups. It is preferred that the majority of these other substituents are hydrocarbyl groups, more preferably alkyl groups, most preferably linear alkyl groups having from 1 to 8 carbon atoms. Particularly preferred are methyl groups or ethyl groups. It is most preferred that substantially all non hydrogen substituents are methyl groups.
  • the reagent compound of the general formula R"- ⁇ has a monovalent hydrocarbon group R", which has aliphatic unsaturation.
  • the group R" is preferably a hydrocarbon group having from 1 to 20 carbon atoms, more preferably 2 to 5, most preferably 2 or 3 carbon atoms. This hydrocarbon group is preferably saturated with the exception of one aliphatic unsaturation, preferably located at the terminal carbon-carbon link. Most preferably R" is a linear alkenyl group.
  • Particular examples of suitable R" groups are vinyl, allyl, isopropenyl, butenyl and isobutenyl groups.
  • Each groups ⁇ is independently selected from optionally substituted aryl groups, preferably having from 6 to 20 carbon atoms.
  • Suitable substituents include halogen, hydroxyl, alkoxy, carboxyl and phenyl. More preferred as aryl groups are those who have from 6 to 9 carbon atoms, especially unsubstituted phenyl groups.
  • the groups ⁇ may be substituted on any of the carbon atoms of the R" group, although preferably they are substituted on the carbon atom at the other end from the aliphatic unsaturation of the R" group. It is however essential that both ⁇ groups are substituted onto the same carbon atom of the R" group. Examples of suitable compounds include 1,1- diphenylethene.
  • R"- ⁇ is preferably in stoichiometric amounts based on the number of Si-H groups in the siloxane which one desires to react with the R"- ⁇ 2 compound. It is possible to use a stoichiometric excess of the compound R"- ⁇ 2 , but in such cases, it is preferred to remove the unreacted compounds from the reaction product if high purity is preferred. Any unreacted Si- H groups remaining in the siloxane compound reaction product are then preferably further reacted with a capping agent, as discussed above under the first aspect of the invention.
  • Hydrosilylation catalysts are known in the art and have been described in a number of publications. They are generally Group Nm transition metal catalysts, as described e.g. in US patents 3,715,334 and 3,814,730. Suitable hydrosilylation catalysts include complexes or compounds of group Nm metals, for example, platinum, ruthenium, rhodium, palladium, osmium and indium.
  • Preferred catalysts are platinum compounds or complexes including chloroplatinic acid, platinum acetylacetonate, complexes of platinous halides with unsaturated compounds, for example, ethylene, propylene, organovinylsiloxanes and styrene, hexamethyldiplatinum, PtCl 2 .PtCl3 and Pt(CN)3-
  • the catalyst may be a rhodium complex, for example, RhCl3(Bu 2 S)3.
  • these catalysts are used in amounts of between about 0.0001 and 10 wt. % based on the weight of the reagent siloxane polymer.
  • Hydrosilylation reactions are generally carried out at a temperature of from 40°C up to 200°C, preferably 80°C to 150°C, and at normal atmospheric pressure, although both lower and higher pressures can be applied.
  • the hydrosilylation catalyst are designed to catalyse a hydrosilylation reaction, they can also be active to catalyse condensation reactions, such as those described above for the capping agents.
  • siloxane compounds according to the present invention are found to have exceptionally interesting refractive indexes, especially the more preferred compounds, where refractive indices above 1.53 are not exceptional, even values above 1.55 can be achieved consistently. Such refractive indices are rarely achieved for siloxane materials, and some of the values seen were never previously achieved for siloxane compounds. It follows that these compounds have a very wide potential use in applications where refractive index values are important. Such uses include coating applications, additives for construction materials or decorative materials, for example paints and varnishes, cosmetic applications, in particular antiperspirant applications, hair care applications, including conditioning, colouring and dyeing applications and skin care applications, including moisturising, colouring, protecting and general treatment applications.
  • siloxane compounds according to the first aspect of the invention and even those which do not have both ⁇ groups on a single carbon atom or those having only one -(O) x R'- ⁇ 2 group per molecule, regardless of the number of silicon atoms or the R' group, have demonstrated benefits in many applications, significantly in personal care applications where the high refractive index can offer masking of antiperspirant salts in under arm products. They have demonstrated excellent compatibility with a very wide range of organic chemicals (including hydrocarbon oils, esters, alcohols, waxes and silicones), in particular they have shown excellent compatibility with castor oil and perfumes and essential oils, in comparison to many other phenyl containing silicones.
  • organic chemicals including hydrocarbon oils, esters, alcohols, waxes and silicones
  • the invention provides in another aspect a cosmetic skin, body or hair care composition
  • a cosmetic skin, body or hair care composition comprising a siloxane compound having at least 2 silicon atoms linked by oxygen and at least one silicon-bonded substituent of the general formula -(O) x R'- ⁇ 2 wherein R' denotes a divalent hydrocarbon radical and ⁇ denotes a potentially substituted aryl group. It is particularly preferred that both potentially substituted aryl groups are linked directly to one and the same carbon atom in the R' group. Particularly preferred are those cosmetic skin, body or hair care compositions comprising siloxane compounds according to the first invention, i.e.
  • the skin care composition is selected from colour cosmetic compositions, and in particular lipstick, nail varnish, foundation creams, compact powders and mascara.
  • the application intended is selected from hair colouring or hair dyeing applications and hair conditioners.
  • Skin, body and hair care compositions would incorporate siloxane compounds in an amount of from 0.1 up to 50% by weight of the total composition, preferably from 1 to 10% by weight, more preferably 3 to 7% by weight. They could be incorporated as a pure material, or included in an emulsion or dispersion. They may be applied to a powder or mixed in with liquid or paste like materials.
  • reaction mixture was periodically sampled and analysed by gas-liquid chromatography (gc) and the reduction in unreacted tetramethyldisiloxane and 1,1- diphenylethene was followed, showing a corresponding increase in reaction products with time.
  • the principal reaction product was the addition product of 1,1-diphenylethene and the silicon hydride. Due to the stoichimetric excess of SiH (2 SiH groups per molecule) over unsaturated carbon, trace residues of 1,1-diphenylethene remained together with a significant concentration of the mono-substituted disiloxane.
  • Periodic sampling of the mixture for analysis by gc showed the gradual consumption of all tetramethyldisiloxane, with only a trace of unreacted 1,1-diphenylethene and about 5% of mono substituted disiloxane left.
  • the mixture was allowed to cool to room temperature and 14g (0.13 moles), corresponding to an addition level of 2 % of benzyl alcohol was added.
  • the mixture was heated to 125°C and held for 16 hours after which all but a trace of the mono-substituted disiloxane remained, as observed by gc.
  • the resultant material was filtered through a 5 micron filter to yield a pale straw liquid, having a viscosity of 135.8 rnm ⁇ s-!, a refractive index of 1.5604, a residual SiH content of 5ppm and a residual 1,1-diphenylethene level of 10 ppm.
  • Example 3 The process of Example 3 was repeated, but the benzyl alcohol was replaced with 1-octene, allyloxy ethanol, and geraniol respectively.
  • the resulting siloxane compounds only reduced the refractive index by less than 0.05 units (i.e. retaining final refractive index above 1. 54).
  • This product was then mixed in a ratio of 1 :3 to the prehydrolised silane of Example 7, and the mixture was hydrolysed in a water/toluene mixture with sodium bicarbonate to mop up the HC1 produced. After removal of the solvents and by-products, a mixture in a 1 :1 weight ratio was obtained of the disiloxane of Example 7 and a trisiloxane compound having on each silicon atom a diphenylethylene substituent with a viscosity of 66mm2s-l and a refractive index of 1.572.
  • the mixture was shown to consist of a trace of unreacted tetramethyldisiloxane, a slight trace of unreacted alpha-methyl styrene dimer and a significant portion of monosubstituted disiloxane.
  • a further 5 ppm of Pt was added and heating continued to 120°C for a further 24 hours.
  • the resultant product was shown to contain 20 ppm residual SiH, 4528 ppm alpha-methylstyrene dimer having a viscosity of 109.3 mm ⁇ s'l and a refractive index of 1.5372.
  • a lipstick was prepared by making a pigment formulation of 5 parts of
  • Covasil® TiO2 17.5 parts of Covasil® red W3801 and 77.5 parts of decamethyl cyclosiloxane. 27 parts of this pigment formulation was then formulated with 8 parts Novol®, 2 parts avocado oil, 9 parts lanolin oil, 4 parts petrolatum, 5 parts of a siloxane having methyl and C16 alkyl substituents on most silicon atoms, 25 parts of Eutanol® G, 11 parts of candellila wax, 5 parts of the siloxane material of Example 2 and 4 parts of white ozokerite wax.
  • the resulting lipstick was tested by a panel of experts and found to be easy to apply and retain a very high gloss, even after prolonged time.
  • a lip gloss product was made using 16.5 parts of Dow Corning® 2-8178 silicone polyamide gellant, 32.96 parts of decamethyl cyclopentasiloxane, 22.42 parts of isopropyl myristate, 22.42 parts of Crodamol® GTCC, 0.2 parts of a pigment mix and 5.5 parts of the siloxane compound of Example 2.
  • the finished product was tested by a panel of experts and was shown to give a good level of gloss when applied.

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Abstract

L'invention concerne un composé de siloxane ayant au moins 2 atomes de silicium reliés par l'oxygène et au moins un substituant lié à un silicium de formule générale (O)x R'- Ζ2, dans laquelle R' représente un radical d'hydrocarbure divalent, x a une valeur de 0 ou 1 et chaque Ζ représente indépendamment un groupe aryle éventuellement substitué, les deux groupes aryle éventuellement substitués étant directement liés au même atome de carbone dans le groupe R', excepté lorsque seulement un groupe (O)x R'- Ζ2 est présent dans le siloxane, que le siloxane contienne au moins 3 atomes de silicium ou, dans le cas où le siloxane ne contient que 2 atomes de silicium, que R' représentant diméthylène ait une valeur d'indice de réfraction élevée. Nombre de ces composés de siloxane présentent des indices de réfraction exceptionnellement intéressants, y comprise ceux excédant 1,53, voire 1,55, ce qui est exceptionnel s'agissant de silicones classiques. L'invention concerne des compositions cosmétiques comprenant de tels siloxanes, qui sont de préférence choisies dans des applications cosmétiques de couleur, à savoir rouge à lèvres, vernis à ongles, mascara, fond de teint, poudres compactes, colorants capillaires et revitalisants.
PCT/EP2004/011021 2003-02-11 2004-02-10 Composes de siloxane Ceased WO2005000856A2 (fr)

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GB0302978.2 2003-02-11
GBGB0302978.2A GB0302978D0 (en) 2003-02-11 2003-02-11 Siloxane compounds

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WO2005000856A3 WO2005000856A3 (fr) 2005-02-24

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FR2910301A1 (fr) * 2006-12-20 2008-06-27 Oreal Procede de traitement des fibres capillaires avec des compositions contenant des silicones reactives
US7740664B2 (en) 2006-12-20 2010-06-22 L'oreal S.A. Composition comprising at least one silicone compound and at least one organosilane
US7744857B2 (en) 2003-02-11 2010-06-29 Unilever Home & Personal Care Usa A Division Of Conopco, Inc. Antiperspirant compositions
US7780742B2 (en) 2006-12-20 2010-08-24 L'oreal S.A. Composition comprising a compound X and A compound Y, at least one of which is a silicone, and a hydrophobic direct dye
US9862735B2 (en) 2015-09-28 2018-01-09 Shin-Etsu Chemical Co., Ltd. Organosilicon compound having diphenylethyl and methoxysilyl and making method
WO2023025895A1 (fr) * 2021-08-25 2023-03-02 Inalfa Roof Systems Group B.V. Ensemble de panneau de toit transparent pour toit de véhicule

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JP2983744B2 (ja) * 1992-02-18 1999-11-29 株式会社メニコン 眼用レンズ材料
JP3219588B2 (ja) * 1994-03-25 2001-10-15 キヤノン株式会社 電子写真感光体及び電子写真装置
US6365141B2 (en) * 1998-11-06 2002-04-02 General Electric Company Method of using an aralkylsiloxane

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