WO1998055088A1 - Surfactant compositions - Google Patents
Surfactant compositions Download PDFInfo
- Publication number
- WO1998055088A1 WO1998055088A1 PCT/GB1998/001568 GB9801568W WO9855088A1 WO 1998055088 A1 WO1998055088 A1 WO 1998055088A1 GB 9801568 W GB9801568 W GB 9801568W WO 9855088 A1 WO9855088 A1 WO 9855088A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- water
- composition
- surfactant
- emulsion
- Prior art date
Links
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/066—Multiple emulsions, e.g. water-in-oil-in-water
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
Definitions
- This invention relates to surfactant compositions and particularly to such compositions in which block copolymeric surfactants are used to disperse aqueous phases in oil phases in personal care products.
- Polymeric surfactants are known for use in stabilising oil water interfaces, particularly in water-in-oil emulsions oil-in-water emulsions and dispersions.
- Such surfactants include A-B-A block co-polymeric surfactants in which the A blocks are polyester blocks, particularly polyesters of hydroxy aliphatic acids e.g. of hydroxystearic acid to give polyhydroxy stearate (PHS) blocks, and the B block is a polyalkylene glycol block, especially a polyethylene glycol (PEG) block.
- PHS polyhydroxy stearate
- PEG polyethylene glycol
- the molecules of these surfactants have a shape that makes them particularly useful in stabilising water-in-oil dispersions and emulsions. It is believed that, at the oil/water interface, the molecule sits with the hydrophilic PEG block in the water phase and the two hydrophobic PHS blocks in the oil phase. This arrangement gives good packing at the interface and is believed to contribute to the effectiveness of these materials.
- this type of surfactant was, manufactured by a process which used an organic solvent, typically xylene, so that the final product included trace quantities of the solvent that effectively precluded the use of these surfactants in skin contact applications.
- the present invention is based on our discovery that this type of surfactant can achieve particularly good results in certain types of formulation.
- formulations including relatively high concentrations of solutes in a dispersed hydrophilic phase and in the manufacture of multiple emulsions by a particularly convenient route are particularly good results in certain types of formulation.
- this type of surfactant can achieve particularly good results in certain types of formulation.
- the present invention provides a personal care composition which is or includes a hydrophile-in-oil emulsion or dispersion which includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where each group A is independently an oligo- or polyester residue of a hydroxycarboxylic acid, having a molecular weight of from 900 to 3000 Daltons (Da); and B is a polyoxyalkylene chain having a molecular weight of from 400 to 2500 Da, and in which the dispersed hydrophile phase is or includes dissolved therein one or more polyol, alcohol, electrolyte or urea.
- a hydrophile-in-oil emulsion or dispersion which includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where each group A is independently an oligo- or polyester residue of a hydroxycar
- the block group A is typically made up of repeat units of the formula:
- the repeat units in the blocks A are particularly desirably of 12-hydoxystearic acid i.e. where a is 5 and b is 10. Desirably, the number of fatty acid residues in each block A residues is on average from 3 to 10 (900 to 3000 Da), particularly from about 5 to about 8 (about 1500 to about 2400 Da) and especially about 7 (about 2100 Da).
- 12-hydroxystearic acid is typically manufactured by hydrogenation of castor oil fatty acids including the C18 unsaturated hydroxy acid and the non-substituted unsaturated fatty acids (oleic and linoleic acids) which on hydrogenation gives a mixture of 12-hydroxystearic and stearic acids.
- the presence of the unsubstituted acid acts to limit the chain length of the oligomer or polymer.
- Hydroxystearic acid is available containing about 15% unsubstituted stearic acid and this on polymerisation gives an average chain length of about 6 hydroxystearate residues terminated by a stearic acid residue.
- the polyoxyalkylene chain is desirably a poiyoxyethylene chain and, in particular, it has a molecular weight of from about 400 to about 2000 Da and especially about 1500 Da.
- a particularly useful material is the solvent free block copolymer polymeric surfactant sold by ICI Surfactants under the trade name Arlacel P135 which has a PEG residue with a molecular weight of about 1500, corresponding to about 34 ethylene oxide repeat units, and polyhydroxystearate residues each containing about 7 acid residues each, corresponding to a chain molecular weight of about 2100, and an overall molecular weight of about 5.5 to 6 kD
- the oil phase used in the invention is typically an emollient oil which may be liquid or solid at ambient temperature.
- Suitable liquid emollient oils include non-polar oils such as mineral oils e.g. paraffin or /so-paraffin oils, and polar oils, particularly ester oils such as triglyceride oil e.g. vegetable oils or synthetic trigiycerides, synthetic ester oils ether oils silicone oils and alkoxylated oils.
- Suitable emollients that are solid at ambient temperature include emollient waxes such as paraffin waxes, ozokerite, beeswax and vegetable waxes e.g. castor wax and candelilla wax.
- the oil phase may include other components such as essential oils, oil soluble vitamins, antioxidants, pigments, hydrophobic silica (such as Aerosil R972 ex Degussa), UVB and UVA sunscreen agents, and similar materials.
- essential oils oil soluble vitamins, antioxidants, pigments, hydrophobic silica (such as Aerosil R972 ex Degussa), UVB and UVA sunscreen agents, and similar materials.
- hydrophobic silica such as Aerosil R972 ex Degussa
- UVB and UVA sunscreen agents and similar materials.
- the hydrophile phase can be a solution in water of the hydrophilic material or can, in certain cases, be a substantially water free liquid phase of the hydrophilic material.
- the invention includes:
- a personal care composition which is or includes a water-in-oil emulsion or dispersion in which the dispersed water phase includes dissolved therein at least one electrolyte, particularly where the electrolyte is aluminium and/or zirconium chlorohydrate, sodium chloride or a salt of an organic acids such as sodium lactate, and particularly at a concentration of from 0.1 to 25% by weight of the aqueous phase, and which further includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where A and B are as defined above;
- a personal care composition which is or includes a water-in-oil emulsion or dispersion in which the dispersed water phase includes urea dissolved therein, particularly at a concentration of from 0.1 to 20% by weight of the aqueous phase, and which further includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where A and B are as defined above;
- a personal care composition which is or includes a hydrophile-in-oil emulsion or dispersion in which the dispersed hydrophile phase is a polyol or is water having a polyol dissolved therein, particularly glycerol, glycerol ethoxylated with from 1 to 100 moles of ethylene oxide, propylene glycol (1 ,2 propane diol), butylene and/or hexylene glycol, sorbitol, sorbitol ethoxylated with form 1 to 100 moles of ethylene oxide and polyethylene glycol (especially having a molecular weight distribution between 200 to 6000 Da with a typical average molecular weight of about 1500 Da), and which further includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where A and B are as defined above; and
- a personal care composition which is or includes a water-in-oil emulsion or dispersion in which the dispersed water phase includes at least one alcohol dissolved therein, particularly in an amount of from 1 to 40%, and which further includes as a dispersant and/or emulsifying agent a block copolymeric surfactant of the formula: A - B - A where A and B are as defined above.
- the polymeric surfactant is typically used in an amount of 0.5 to 5%, more usually from 1 to 2%, by weight of the total emulsion.
- the system can be formulated as a multiple water-in-oil-in-water emulsion, by dispersing the hydrophile-in-oil emulsion in water, i.e. using conventional 2-step multiple emulsion manufacturing methods.
- double emulsions can contain from 30 to 90%, particularly from 50 to 80%, by weight based on the total multiple emulsion of the primary internal phase.
- the hydrophile is a glycol or glycerol, particularly where it is glycerol, the hydrophile phase may contain little if any water.
- aqueous emulsions containing water sensitive materials, or materials that are sensitive to other environmental effects e.g. oxidation, in the presence of water, such as some water soluble vitamins especially vitamin C.
- the water sensitive material is dissolved in the hydrophile phase emulsified in an oil continuous phase and this emulsion is then emulsified into water or an aqueous phase.
- the invention includes a method of making an oil-in-water emulsion containing water-in-oil droplets which includes forming a mixture of an oil phase and oil-in-water primary emulsifier for dispersing oil in an aqueous phase including also an oil soluble copolymer surfactant of the formula : A - B - A where A and B are defined as above, and adding to the oil mixture under stirring to an aqueous phase.
- Suitable primary emulsifier surfactants are combinations of hydrophilic surfactants such as fatty alcohol, e.g. C 12 to C 22 fatty alcohols, ethoxylates having a high degree of ethoxylation e.g. an average of more than 15 ethoxylate residues per molecule, such as the hydrophilic ethoxylates supplied by ICI Surfactants under the trade designation Brij, particularly Brij 721 , Brij 78, Brij 98 and
- Brij 99 and hydrophobic surfactants such as fatty alcohol, e.g. C 12 to C 22 fatty alcohols, ethoxylates having a low degree of ethoxylation e.g. an average of not more than 5, and usually not more than 3, ethoxylate residues per molecule, such as the hydrophobic ethoxylates supplied by ICI Surfactants under the trade designation Brij, particularly Brij 72, Brij 92 and Brij 93.
- Such combinations can form liquid crystal like phases at or near the oil-water interface and stabilise the oil droplets.
- amphiphiles such as fatty alcohols, in particular C 12 to C 22 fatty alcohols, (in addition to any residual fatty alcohol which may be present especially in the hydrophobic component of the primary emulsifier) in the primary emulsifier.
- the relative amounts of hydrophilic surfactant and hydrophobic surfactant depend on the multiple emulsion system but are typically in the weight range 3:1 to 1 :5, particularly 1 :1 to 1 :2, especially about 1 :1.5.
- the relative weight of added fatty alcohol based on the combination of the hydrophilic and hydrophobic surfactants will usually be in the range 1 :10 to 1 :1 , more usually 1 :5 to 1 :2.
- the multiple emulsion can be made by dissolving the hydrophobic and hydrophilic surfactants in the oil phase and adding the oil phase to the water phase under stirring. Conveniently this is done at moderately elevated temperatures e.g. between ambient temperature and 90°C, more usually between 70 and 85°C.
- the amount of the polymeric surfactant used in making multiple emulsions in this way will typically be from 0.1 to 2% by weight of the total multiple emulsion.
- the amount of the primary emulsifier surfactant system (including any additional fatty alcohol) used is typically from 0.5 to 12%, particularly from about 3 to about 8% and especially from 5 to 7%, by weight of the total multiple emulsion.
- This method has the practical advantage that only one emulsification step is needed in order to form a double/multiple emulsion, thus, thus simplifying and cheapening the production process.
- the method is restricted to such systems where the main external (aqueous) phase and the second internal (aqueous) phase are formed from the same aqueous phase, although post emulsification additions to the main external (aqueous) phase does enable the manufacture of systems where the two aqueous phases are not the same.
- the oil phase can be similar to those described above. However, it is very desirable that the oil is a solvent for the polymeric surfactant to aid manufacture.
- the oil phase may include other components such as essential oils, oil soluble vitamins, antioxidants, pigments, hydrophobic silica (such as Aerosil R972 ex Degussa), UVB and UVA sunscreen agents, and similar materials.
- essential oils oil soluble vitamins, antioxidants, pigments, hydrophobic silica (such as Aerosil R972 ex Degussa), UVB and UVA sunscreen agents, and similar materials.
- hydrophobic silica such as Aerosil R972 ex Degussa
- UVB and UVA sunscreen agents and similar materials.
- Nipaguard BPX A combination of phenoxyethanol, methylparaben propylparaben and 2-bromo-2-nitropropane-1 ,3-diol ex Nipa Keltrol Xanthan Gum ex Kelko
- Example 1 Water-in-oil after-sun milk including ethanol in the internal phase.
- the after-sum milk product was made by heating components A and B separately to 75°C, slowly adding B to A under intensive stirring, homogenising thoroughly for 1 minute. The emulsion was allowed to cool to 35°C under intensive stirring, component C was then added slowly and the product cooled to ambient temperature maintaining the intensive stirring. The product had a viscosity of 4450 mPa.s (Brookfield LVT, spindle C, 6 rpm)
- Example 2 Water-in-oil cleansing milk including glycerol and ethanol in the internal phase
- Example 2 The manufacturing procedure described in Example 1 was used.
- the product had a viscosity of 7880 mPa.s (Brookfield LVT, spindle C, 6 rpm)
- the water-in-oil antiperspirant cream product was made by heating components A and B separately to 75-80°C, slowly adding B to A under intensive stirring at ca 800 rpm (ca 170 Hz), homogenising thoroughly for 1 minute.
- the emulsion was allowed to cool to 50°C under intensive stirring, then component C was then added slowly and the product cooled to ambient temperature under stirring.
- the product had a viscosity of 50000 mPa.s (Brookfield LVT, spindle F, 6 rpm).
- Example 4 Water-in-oil emulsion including natural oils and urea in the aqueous phase
- the water-in-oil emulsion product was made by heating components A and B separately to 75, slowly adding B to A under intensive stirring, homogenising thoroughly for 1 minute, cooling under intensive stirring to 45°C, homogenising thoroughly for 1 minute and then cooling the product to ambient temperature under stirring.
- the product of Example 4a had a viscosity of 125580 mPa.s (Brookfield LVT, spindle F, 6 rpm) and that of Example 4b a viscosity of 116220 mPa.s (Brookfield LVT, spindle F, 6 rpm).
- the product of Example 4a was stable under accelerated storage testing conditions at 50°C for at least 1 week and the product of Example 4b was stable under accelerated storage testing conditions at 50°C for at least 1 month.
- the water-in-oil hydrating cream product was made by heating components A and B separately to 70°C, adding B to A under intensive stirring, homogenising thoroughly for 1 minute, cooling under stirring to 40°C, adding component C (urea dispersed in water) and homogenising the mixture thoroughly for 1 minute and then cooling the product to ambient temperature under continuous stirring.
- the product had a viscosity of 24160 mPa.s (Brookfield RDV1+, spindle 6, 6 rpm).
- the water-free cream product was made by heating components A and B separately to 75°C, adding B to A under intensive stirring, homogenising thoroughly for 1 minute, cooling under moderate stirring to ambient temperature.
- the product had a viscosity of 130600 mPa.s (Brookfield RDVI+, spindle 7, 6 rpm)
- the in-situ multiple emulsion product was made by heating components A and B separately to 75°C, slowly adding A to B under moderate stirring, homogenising gently for 1 minute and cooling under intensive stirring to ambient temperature. Viscosity measurements made on a Brookfield LVT viscometer using spindle E, 6 rpm are included below).
- Arlamol E 5.0 wt%
- Arlamol HD 4.0 wt%.
- the glycerol-in-oil-in-water emulsion product was made in two stages.
- the primary giycerol-in-oil emulsion was made by heating components A and B separately to 75°C, slowly adding B to A under intensive stirring, homogenising thoroughly for 1 minute and cooling under stirring to ambient temperature.
- the Secondary emulsion was made by forming component B' by dispersing the Synperonic PE/F 127 in the water at 5°C whilst stirring then adding the Nipaguard and slowly adding the primary emulsion (Component A') to B' under thorough stirring to form a multiple emulsion.
- Component C was made by slowly dispersing the Keltrol into the water under stirring and continuing stirring until a homogeneous gel is formed. Component C was gradually added to the multiple emulsion formed previously under gentle stirring.
- the product had a viscosity of 70000 mPa.s (Brookfield LVT, spindle E, 6 rpm).
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU76668/98A AU7666898A (en) | 1997-06-07 | 1998-05-28 | Surfactant compositions |
EP98924470A EP0986369A1 (en) | 1997-06-07 | 1998-05-28 | Surfactant compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9711786.5 | 1997-06-07 | ||
GBGB9711786.5A GB9711786D0 (en) | 1997-06-07 | 1997-06-07 | Surfactant compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998055088A1 true WO1998055088A1 (en) | 1998-12-10 |
Family
ID=10813725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1998/001568 WO1998055088A1 (en) | 1997-06-07 | 1998-05-28 | Surfactant compositions |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0986369A1 (en) |
JP (1) | JPH1112125A (en) |
AU (1) | AU7666898A (en) |
GB (1) | GB9711786D0 (en) |
WO (1) | WO1998055088A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19841798A1 (en) * | 1998-09-12 | 2000-03-16 | Beiersdorf Ag | Nonionic and/or amphoteric surfactant-containing water-in-oil emulsions containing surfactive additive such as PEG-30 dipolyhydroxystearate to allow incorporation of UV filters for sunscreen manufacture |
DE19920839A1 (en) * | 1999-05-06 | 2000-12-07 | Beiersdorf Ag | Flowable preparations of emulsion type W / O with increased water content with a content of medium polar lipids |
FR2820976A1 (en) * | 2001-02-21 | 2002-08-23 | Rhodia Chimie Sa | Cosmetic or dermatological formulation comprising two or more types of active matter in a multiple emulsion consisting of an internal aqueous phase dispersed in an internal oily phase dispersed in an external aqueous phase |
WO2005107681A1 (en) * | 2004-04-29 | 2005-11-17 | Cognis Ip Management Gmbh | Emulsifier concentrate for a cosmetic composition |
WO2011116049A1 (en) | 2010-03-17 | 2011-09-22 | Croda, Inc. | Polymeric surfactant |
US9687425B2 (en) | 2014-06-30 | 2017-06-27 | The Procter & Gamble Company | Personal care compositions and methods |
EP3082710A4 (en) * | 2013-12-17 | 2017-07-26 | Avon Products, Inc. | Glycerin-in-oil emulsion |
US9717930B2 (en) | 2013-03-12 | 2017-08-01 | The Procter & Gamble Company | Antiperspirant compositions |
US9877909B2 (en) | 2014-06-30 | 2018-01-30 | The Procter & Gamble Company | Personal care compositions and methods |
US10016343B2 (en) | 2013-03-12 | 2018-07-10 | The Procter & Gamble Company | Solid stick antiperspirant compositions |
US10758476B1 (en) | 2017-09-18 | 2020-09-01 | Type A Brands, Llc | Deodorant with sweat-activated technology |
US11041137B2 (en) | 2013-10-29 | 2021-06-22 | Croda, Inc. | Lubricant composition comprising hydroxycarboxylic acid derived friction modifier |
US11697783B2 (en) | 2016-06-03 | 2023-07-11 | Equus Uk Topco Ltd | Lubricant composition |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4601031B2 (en) * | 2001-03-16 | 2010-12-22 | 株式会社資生堂 | W / O / W emulsified cosmetics |
JP4741109B2 (en) * | 2001-05-31 | 2011-08-03 | 株式会社コーセー | Oily cosmetics |
TWI366469B (en) | 2005-07-26 | 2012-06-21 | Shiseido Co Ltd | Emulsified skin agent for external use |
JP5415037B2 (en) * | 2007-10-04 | 2014-02-12 | 森永製菓株式会社 | Collagen production promoter |
JP5430891B2 (en) * | 2007-10-04 | 2014-03-05 | 森永製菓株式会社 | Melanin production inhibitor |
JP2010030911A (en) * | 2008-07-25 | 2010-02-12 | Morinaga & Co Ltd | Collagen production promotor |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2340981A1 (en) * | 1976-02-12 | 1977-09-09 | Ici Ltd | Solubilising water insol. cpds. esp. essential oils - and liposoluble vitamins, using non-ionic surfactants |
US4549009A (en) * | 1976-08-10 | 1985-10-22 | The Nisshin Oil Mills, Ltd. | Polymeric glycol ester |
US4931210A (en) * | 1984-03-26 | 1990-06-05 | Menji Milk Products Company Limited | Process for producing a W/O/W type multiple emulsion for medicines, cosmetics, etc. |
WO1997040815A1 (en) * | 1996-04-30 | 1997-11-06 | The Procter & Gamble Company | Cleaning articles comprising a polarphobic region and a high internal phase inverse emulsion |
WO1997040814A1 (en) * | 1996-04-30 | 1997-11-06 | The Procter & Gamble Company | Cleaning articles treated with a high internal phase inverse emulsion |
EP0858800A1 (en) * | 1997-02-06 | 1998-08-19 | L'oreal | Water in oil emulsions based on two specific emulsifiers and cosmetic uses thereof |
-
1997
- 1997-06-07 GB GBGB9711786.5A patent/GB9711786D0/en active Pending
- 1997-07-10 JP JP18500897A patent/JPH1112125A/en active Pending
-
1998
- 1998-05-28 AU AU76668/98A patent/AU7666898A/en not_active Abandoned
- 1998-05-28 EP EP98924470A patent/EP0986369A1/en not_active Withdrawn
- 1998-05-28 WO PCT/GB1998/001568 patent/WO1998055088A1/en active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2340981A1 (en) * | 1976-02-12 | 1977-09-09 | Ici Ltd | Solubilising water insol. cpds. esp. essential oils - and liposoluble vitamins, using non-ionic surfactants |
US4549009A (en) * | 1976-08-10 | 1985-10-22 | The Nisshin Oil Mills, Ltd. | Polymeric glycol ester |
US4931210A (en) * | 1984-03-26 | 1990-06-05 | Menji Milk Products Company Limited | Process for producing a W/O/W type multiple emulsion for medicines, cosmetics, etc. |
WO1997040815A1 (en) * | 1996-04-30 | 1997-11-06 | The Procter & Gamble Company | Cleaning articles comprising a polarphobic region and a high internal phase inverse emulsion |
WO1997040814A1 (en) * | 1996-04-30 | 1997-11-06 | The Procter & Gamble Company | Cleaning articles treated with a high internal phase inverse emulsion |
EP0858800A1 (en) * | 1997-02-06 | 1998-08-19 | L'oreal | Water in oil emulsions based on two specific emulsifiers and cosmetic uses thereof |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19841798A1 (en) * | 1998-09-12 | 2000-03-16 | Beiersdorf Ag | Nonionic and/or amphoteric surfactant-containing water-in-oil emulsions containing surfactive additive such as PEG-30 dipolyhydroxystearate to allow incorporation of UV filters for sunscreen manufacture |
DE19920839A1 (en) * | 1999-05-06 | 2000-12-07 | Beiersdorf Ag | Flowable preparations of emulsion type W / O with increased water content with a content of medium polar lipids |
FR2820976A1 (en) * | 2001-02-21 | 2002-08-23 | Rhodia Chimie Sa | Cosmetic or dermatological formulation comprising two or more types of active matter in a multiple emulsion consisting of an internal aqueous phase dispersed in an internal oily phase dispersed in an external aqueous phase |
WO2005107681A1 (en) * | 2004-04-29 | 2005-11-17 | Cognis Ip Management Gmbh | Emulsifier concentrate for a cosmetic composition |
WO2011116049A1 (en) | 2010-03-17 | 2011-09-22 | Croda, Inc. | Polymeric surfactant |
CN102918065A (en) * | 2010-03-17 | 2013-02-06 | 禾大公司 | Polymeric surfactant |
EP2547701A4 (en) * | 2010-03-17 | 2015-10-28 | Croda Inc | Polymeric surfactant |
US9315621B2 (en) | 2010-03-17 | 2016-04-19 | Croda, Inc. | Polymeric surfactant |
US9717930B2 (en) | 2013-03-12 | 2017-08-01 | The Procter & Gamble Company | Antiperspirant compositions |
US10016343B2 (en) | 2013-03-12 | 2018-07-10 | The Procter & Gamble Company | Solid stick antiperspirant compositions |
US10052271B2 (en) | 2013-03-12 | 2018-08-21 | The Procter & Gamble Company | Antiperspirant compositions |
US9937113B2 (en) | 2013-03-12 | 2018-04-10 | The Procter & Gamble Company | Antiperspirant compositions |
US11041137B2 (en) | 2013-10-29 | 2021-06-22 | Croda, Inc. | Lubricant composition comprising hydroxycarboxylic acid derived friction modifier |
EP3082710A4 (en) * | 2013-12-17 | 2017-07-26 | Avon Products, Inc. | Glycerin-in-oil emulsion |
US9877909B2 (en) | 2014-06-30 | 2018-01-30 | The Procter & Gamble Company | Personal care compositions and methods |
US9750671B2 (en) | 2014-06-30 | 2017-09-05 | The Procter & Gamble Company | Personal care compositions and methods |
US10154949B2 (en) | 2014-06-30 | 2018-12-18 | The Procter & Gamble Company | Personal care compositions and methods |
US10413493B2 (en) | 2014-06-30 | 2019-09-17 | The Procter & Gamble Company | Personal care composition and methods |
US10716743B2 (en) | 2014-06-30 | 2020-07-21 | The Procter & Gamble Company | Personal care compositions and methods |
US9687425B2 (en) | 2014-06-30 | 2017-06-27 | The Procter & Gamble Company | Personal care compositions and methods |
US11697783B2 (en) | 2016-06-03 | 2023-07-11 | Equus Uk Topco Ltd | Lubricant composition |
US10758476B1 (en) | 2017-09-18 | 2020-09-01 | Type A Brands, Llc | Deodorant with sweat-activated technology |
Also Published As
Publication number | Publication date |
---|---|
EP0986369A1 (en) | 2000-03-22 |
AU7666898A (en) | 1998-12-21 |
JPH1112125A (en) | 1999-01-19 |
GB9711786D0 (en) | 1997-08-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1998055088A1 (en) | Surfactant compositions | |
US6242499B1 (en) | Polyglycerol partial esters of fatty acids and polyfunctional carboxylic acids, their preparation and use | |
JP5047369B2 (en) | Method for producing O / W fine emulsion external preparation | |
US5391321A (en) | Liquid or pasty, storage-stable multiple emulsions of the O1 /W/O.sup.2 | |
US4379755A (en) | Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom | |
KR100623013B1 (en) | Nano-emulsion, the use thereof, and preparing method thereof | |
WO2011027811A1 (en) | Method for producing o/w emulsion composition | |
EP1380278A1 (en) | Cosmetic emulsion preparation and agent for external use | |
US20130018104A1 (en) | Emulsive composition containing dapsone | |
EP0217105A2 (en) | Lamella type single phase liquid crystal composition and oil-base cosmetic compositions using the same | |
JP5244989B2 (en) | Method for producing O / W emulsion composition | |
US6630151B1 (en) | Method of increasing viscosity of oil-based compositions and compositions resulting therefrom | |
KR20150116655A (en) | Cosmetic composition stabilizing insoluble functional ingredient | |
JPH1190211A (en) | Preparation of o/w type emulsion | |
JPS63126543A (en) | Microemulsion | |
JP4303984B2 (en) | Stable dispersion concentrate | |
JP3440437B2 (en) | O / W / O emulsion composition | |
JP2000237570A (en) | Emulsifier | |
JPH07304629A (en) | Water-in-oil type emulsion composition and its production | |
JPH09220464A (en) | Polyhydric alcohol gel-in-oil type emulsified composition and its production | |
CN111801091A (en) | Oil-in-water droplet type micro emulsion type cosmetic | |
JPS63126541A (en) | Low-water content o/w type emulsion and its production | |
JP2000128760A (en) | Cosmetic | |
JP6672730B2 (en) | Cosmetic comprising nanoemulsion and method for producing the same | |
JP7301826B2 (en) | Compounds suitable for personal care and cosmetic applications |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM GW HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1998924470 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09456182 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: JP Ref document number: 1999501827 Format of ref document f/p: F |
|
WWP | Wipo information: published in national office |
Ref document number: 1998924470 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
NENP | Non-entry into the national phase |
Ref country code: CA |