EP1401922A1 - Verfahren zur stabilisierung einer wässrigen dispersion einer öl-in-silikonöl-emulsion - Google Patents

Verfahren zur stabilisierung einer wässrigen dispersion einer öl-in-silikonöl-emulsion

Info

Publication number
EP1401922A1
EP1401922A1 EP02760371A EP02760371A EP1401922A1 EP 1401922 A1 EP1401922 A1 EP 1401922A1 EP 02760371 A EP02760371 A EP 02760371A EP 02760371 A EP02760371 A EP 02760371A EP 1401922 A1 EP1401922 A1 EP 1401922A1
Authority
EP
European Patent Office
Prior art keywords
weight
phase
dispersed phase
soluble
copolymer
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Withdrawn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
EP02760371A
Other languages
English (en)
French (fr)
Inventor
Hélène LANNIBOIS-DREAN
Jean-Marc Ricca
Mathias Destarac
Philippe Olier
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.)
Rhodia Chimie SAS
Original Assignee
Rhodia Chimie SAS
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 Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Publication of EP1401922A1 publication Critical patent/EP1401922A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes

Definitions

  • alkyl is meant a hydrocarbon chain preferably in CrC 10 , more preferably in C Ce; examples of these groups are - (CH 2 ) 3 -OH; - (CH 2 ) 4 N (CH 2 CH 2 OH) 2 ; - (CH 2 ) 3 -N (CH 2 CH 2 OH) -CH 2 -CH 2 -N (CH2CH 2 OH) 2 ;
  • radicals R ' of: - alkyl, preferably C 1 -C 10 alkyl optionally halogenated, such as methyl, ethyl, octyl, trifluoropropyl;
  • the said copolymer used is that which, at a given concentration in the range indicated above and at 20 ° C., is present simultaneously in the form of a solution in silicone and in the form of a dispersion in the organic phase. It is stated for information only that the copolymer has a number molar mass less than or equal to 100,000 g / mol, more particularly between 1,000 and 50,000 g / mol.
  • the molar mass in number is here given with an absolute value, and can be advantageously determined by combining MALLS (multi-angle light scattering) analyzes and gel permeation chromatography. Note that this method is particularly suitable for copolymers of any mass.
  • NMR which also gives an absolute value for the masses of copolymer.
  • fraction soluble in the organic phase of the copolymer used as stabilizer of the emulsion can be obtained from the abovementioned monomers, combined with monomers of different chemical nature, such as for example hydrophilic monomers, non-ionic or ionic.
  • the copolymer entering into the composition of the emulsion is obtained in part from hydrophilic monomers, it is specified that their content is such that the copolymer meets the criteria set out above, namely the fact that a fraction of said copolymer is soluble in the continuous phase of the emulsion, the other in the dispersed phase; the fraction soluble in the liquid constituting the continuous phase of the emulsion being higher than that soluble in the dispersed phase.
  • the polymer used in the composition of the emulsion is a linear block polymer.
  • said copolymer comprises at least three blocks.
  • a linear or branched alkyl radical containing 1 to 8 carbon atoms optionally substituted with at least one halogen, preferably fluorine, the alkyl radicals preferably being methyl, ethyl, propyl, octyl and 3,3,3-trifluoropropyl,
  • R identical or different, representing an alkyl or aryl group, and / or a polymer chain
  • R6, R 7 are chosen from a halogen group, -NO 2 , -SO3R 10 , -NCO, -ON, -OR 10 , -SR 10 , -N (R 10 ) 2 , -COOR 10 , -O CR 10 , -CON (R 10 ) 2 , -NCO (R 10 ) and -C n F (2 n + i) with n between 1 and 20, preferably equal to 1; - with R 10 representing:
  • R 10 represents a group as defined above for R 10 ; or together form a C2-C4 hydrocarbon chain, optionally interrupted by a heteroatom chosen from O, S and N;
  • - V and V identical or different, represent: H, an alkyl group or a halogen
  • - X and X identical or different, represent H, a halogen or a group
  • radicals (i), (ii) and (iii) which can be advantageously substituted by: substituted phenyl groups, substituted aromatic groups, or
  • the dispersed phase of the emulsion may also comprise at least one active material soluble in said phase (hydrophobic active material). More particularly, the active ingredient (s) are chosen from the active ingredients which can be used in the field of skin and / or hair treatment. Among them are in particular, alone or in mixtures:
  • fixative resins in particular chosen from those which will be described below, as well as fixing and / or styling agents for the hair, such as for example vinyl acetate / crotonate / vinyl neodecanoate copolymers, sold under the name Resyn® 28- 2942 and Resyn® 28-2930 from National Starch.
  • the emulsion used in the process according to the invention can be obtained for example by preparing, on the one hand a first mixture comprising the dispersed organic phase optionally comprising one or more active materials, and on the other hand, a second mixture comprising silicone and polymer; then add the first mixture to the second, with stirring.
  • the stirring can advantageously be carried out by means of a frame blade.
  • the preparation of the emulsion is generally carried out at a temperature between 20 and 80 ° C.
  • the duration of the agitation can be determined without difficulty by a person skilled in the art and depends on the type of apparatus used. It is preferably sufficient for obtain an average droplet size of between 0.1 and 10 ⁇ m, preferably between 0.1 and 5 ⁇ m (measured using a Horiba granulometer).
  • alkylpolyglycosides such as those described in US 4,565,647; - fatty acid amides, for example C8-C20; alone or as a mixture.
  • the formulations can likewise include cationic surfactants such as alkyl dimethylammonium halides, or alternatively amphoteric or zwitterionic surfactants, such as for example betaines, for example lauryl betaine (Mirataine BB from the company Rhodia Chimie); sulfo-betaines; amidoalkylbetaines, such as cocamidopropyl betaine (Mirataine BDJ from the company Rhodia Chimie); sultaines such as cocamidopropyl hydroxy sultaine (Mirataine CBS from the company Rhodia Chimie); alkylamphoacetates and alkylamphodiacetates, such as for example comprising a coconut, lauryl chain (Miranol C2M, C32 in particular, from the company Rhodia Chimie); alkylamphopropionates or alkylamphodipropionates, (Miranol C2M SF); alkyl amphohydroxypropyl sultaine
  • the aqueous formulations may also contain fixative resins. These fixative resins, when they are present, are generally present at concentrations of between 0.01 and 10%, preferably between 0.5 and 5%.
  • the fixing resins used in the aqueous formulations are more particularly chosen from the following resins:
  • copolyesters derived from acid, anhydride or a terephthalic and / or isophthalic and / or sulfoisophthalic diester and a diol such as: - polyester copolymers based on ethylene terephthalate and / or propylene terephthalate and polyoxyethylene terephthalate units , (US 3959230, US 3893929, US 4116896, US 4702857, US 4770666);
  • copolymers comprising polyester units derived from dimethyl terephthalate, isophthalic acid, dimethyl sulfoisophthalate and ethylene glycol and from polyorganosiloxane units (FR 2728915).
  • polyesters-polyurethanes more particularly obtained by reaction of a polyester obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid and a diol, on a prepolymer with terminal isocyanate groups obtained with starting from a polyoxyethylene glycol and a diisocyanate (FR 2334698);
  • the fixing resins are chosen from polyvinylpyrrolidone (PVP), copolymers of polyvinylpyrrolidone and methyl methacrylate, copolymer of polyvinylpyrrolidone and vinyl acetate (VA), polyterephthalene ethylene glycol / polyethylene glycol copolymers, polyterphide copolymers ethylene glycol / polyethylene glycol / sodium polyisophthalate sulfonate, and mixtures thereof.
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate
  • polyvinyl esters grafted on polyalkylenated trunks such as polyvinylacetates grafted on polyoxyethylene trunks (EP 219048); . polyvinyl alcohols.
  • the water-soluble salts of polycarboxylic acids with a molecular weight by weight of the order of 2000 to 100,000 g / mol obtained by polymerization or copolymerization of ethylenically unsaturated carboxylic acids such as acrylic acid, maleic acid or anhydride , fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid, and very particularly polyacrylates of molecular mass by weight of the order of 2000 to 10 000 g / mol (US 3308067), copolymers of acrylic acid and maleic anhydride with a molecular weight by weight of the order of 5000 to 75000 g / mol (EP 66915); . polyethylene glycols, for example of molecular weight by weight of the order of 1000 to 50,000 g / mol.
  • They can also include sequestering agents of metals such as especially calcium, such as citrate ions for example.
  • An aqueous phase is prepared in which the emulsion will be dispersed comprising 16% of Empicol ESB3M (sodium laureth sulfate, sold by Rhodia Chimie); 2% Tegobetaine 7 (cocamidopropyl betaine, marketed by Goldschmidt) and 2% Miranol Ultra C32 (cocoamphodiacetate, marketed by Rhodia Chimie).
  • Empicol ESB3M sodium laureth sulfate, sold by Rhodia Chimie
  • Tegobetaine 7 cocamidopropyl betaine, marketed by Goldschmidt
  • Miranol Ultra C32 cocoamphodiacetate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)
EP02760371A 2001-06-29 2002-07-01 Verfahren zur stabilisierung einer wässrigen dispersion einer öl-in-silikonöl-emulsion Withdrawn EP1401922A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0108652 2001-06-29
FR0108652A FR2826568B1 (fr) 2001-06-29 2001-06-29 Procede de stabilisation de formulation a base de tensioactifs et comprenant une huile organique, minerale et/ ou derive
PCT/FR2002/002279 WO2003002636A1 (fr) 2001-06-29 2002-07-01 Procede de stabilisation d'une dispersion aqueuse d'une emulsion huile dans l'huile silicone

Publications (1)

Publication Number Publication Date
EP1401922A1 true EP1401922A1 (de) 2004-03-31

Family

ID=8864947

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02760371A Withdrawn EP1401922A1 (de) 2001-06-29 2002-07-01 Verfahren zur stabilisierung einer wässrigen dispersion einer öl-in-silikonöl-emulsion

Country Status (5)

Country Link
US (1) US20040241124A1 (de)
EP (1) EP1401922A1 (de)
JP (1) JP2004534127A (de)
FR (1) FR2826568B1 (de)
WO (1) WO2003002636A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA100841C2 (en) 2006-02-21 2013-02-11 Мэри Кей, Инк. Normal;heading 1;heading 2;heading 3;STABLE VITAMIN C COMPOSITIONS
WO2014070689A1 (en) 2012-10-29 2014-05-08 The Procter & Gamble Company Personal care compositions having a tan delta of 0.30 or more at 10°c

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4869897A (en) * 1987-10-22 1989-09-26 The Procter & Gamble Company Photoprotection compositions comprising sorbohydroxamic acid
GB9523167D0 (en) * 1995-11-13 1996-01-17 Unilever Plc Cosmetic composition
GB9912073D0 (en) * 1999-05-24 1999-07-21 Unilever Plc Polysiloxane block copolymers in topical cosmetic and personal care compositions
US6238657B1 (en) * 1999-07-12 2001-05-29 Dow Corning Corporation Oil-in-oil and three-phase emulsions
FR2812296B1 (fr) * 2000-07-25 2002-12-20 Rhodia Chimie Sa Procede de synthese de copolymeres hybrides et organiques par polymerisation radicalaire controlee

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03002636A1 *

Also Published As

Publication number Publication date
FR2826568B1 (fr) 2005-09-02
US20040241124A1 (en) 2004-12-02
JP2004534127A (ja) 2004-11-11
FR2826568A1 (fr) 2003-01-03
WO2003002636A1 (fr) 2003-01-09

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