GB2300629A - Treating polysiloxane-coated pigment particles - Google Patents
Treating polysiloxane-coated pigment particles Download PDFInfo
- Publication number
- GB2300629A GB2300629A GB9509527A GB9509527A GB2300629A GB 2300629 A GB2300629 A GB 2300629A GB 9509527 A GB9509527 A GB 9509527A GB 9509527 A GB9509527 A GB 9509527A GB 2300629 A GB2300629 A GB 2300629A
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- United Kingdom
- Prior art keywords
- coated pigment
- pigment
- coated
- process according
- less
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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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon 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
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/22—Compounds of iron
- C09C1/24—Oxides of iron
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
-
- 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
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
A process of treating pigments which have been coated with silicon hydride-containing polysiloxanes wherein the process comprises dispersing the coated pigment in a non-polar organic solvent, and reacting the silicon hydride containing polysiloxane coated pigment with aqueous or non-aqueous solution of organic or inorganic base so as as to provide a coated pigment having a residual hydride content as measured by hydrogen potential of less than about 0.5ml H 2 /g of coated pigment. The pigment may be an iron oxide or TiO 2 . The inorganic base may be an alkali metal hydroxide in the form of an alcoholic solution.
Description
Process for Treating Coated Pigments
Technical Field
The present invention relates to a process for treating pigments. In particular the present invention relates to a process of treating pigments which are coated with silicon hydride-containing polysiloxanes.
Background of the Invention
Silicon hydride-containing polysiloxanes are a general class of siloxane polymers, the most common of which is poly(methylhydrogen)siloxane.
This polymer contains reactive hydrogen-to-silicon bonds along a polysiloxane chain and can be represented by the following general formula:
Poly(methylhydrogen)siloxanes are used as coatings for pigments which are suitable for use in cosmetic formulations. It is the reactive hydrogen funtionality which provides substantivity to the pigment. However, a common unwanted side reaction of these materials when used in formulations in which water or alcohol is present is nucleophilic attack on residual Si-H functionality to generate hydrogen gas as shown below:
SiH + ROH = SiOR + H2 where ROH is water or alcohol.
The production of hydrogen gas caused by the above reaction has been known to give rise to undesirable "bubbling" in formulations where pigments coated with silicon hydride-containing polysiloxanes are used in the presence of water or alcohol at acidic or alkaline pH. The process according to the present invention seeks to solve this problem.
Hence according to the present invention there is provided a process of treating pigments which have been coated with silicon hydride-containing polysiloxanes wherein the process comprises dispersing the coated pigment in a non-polar organic solvent, and reacting the silicon hydridecontaining polysiloxane coated pigment with an aqueous or non-aqueous solution of organic or inorganic base so as to provide a coated pigment having a residual hydride content as measured by hydrogen potential of less than about 0.5ml/g of coated pigment.
All ratios and percentages herein are by weight unless otherwise specified.
Description of the Invention
The process of treating pigments which have been coated with silicon hydride-containing polysiloxanes according to the present invention comprises two essential steps; a first step of dispersing the coated pigment in a non-polar organic solvent, and a second step of reacting the silicon hydride-containing polysiloxane coating with aqueous or non-aqueous solution of organic or inorganic base so as to provide a pigment dispersion having a residual hydride content as measured by hydrogen potential of less than about 0.5ml H2/g of coated pigment.
Suitable silicon hydride-containing polysiloxanes for use as pigment coatings herein are monoalkyl polysiloxanes, preferably methicone.
Suitable pigments for use in the process herein are inorganic pigments selected from iron oxide, rutile titanium dioxide and anatase titanium dioxide, and mixtures thereof. Typical inorganic pigments include iron oxides of various colours (yellow, red, brown and black), ferric ammonium ferrocyanide (blue), manganese violet, ultramarine blue, chrome oxide (green), titanium dioxide (white) and mixtures of said inorganic pigments.
Typical pearlants for use herein include mica, bismuth oxychloride and treated mica such as titanated micas.
Exemplary pigments useful in the present invention include the C.I.
pigment materials, especially polymer-treated inorganic pigments containing iron oxide or titanium dioxide such as, for example, C.I.
Pigment Yellow 42, C.I. Pigment Red 101, C.I. Pigment Black 11 and C.I.
Pigment White 6.
In the first step of the process according to the invention the coated pigment is dispersed in a non-polar organic solvent. Preferably the nonpolar organic solvent is selected from linear and cyclic polydiorganosiloxane fluids, and mixtures thereof. Cyclomethicone is especially preferred for use in the process herein. Cyclomethicone is commercially available from Dow Corning under the tradename DC21330.
Xylene can also be used as a non-polar organic solvent, but cyclomethicone is the preferred solvent for cosmetic formulations.
The second essential step of the process of the present invention comprises reacting the silicon hydride-containing polysiloxane coated pigment with aqueous or non-aqueous solution of organic or inorganic base so as to provide a pigment dispersion having a residual hydride content as measured by hydrogen potential of less than about 0.5ml H2/g of coated pigment, preferably less than about 0. lml H2/g of coated pigment.
Suitable inorganic bases for use herein are alkali metal hydroxides, preferably potassium hydroxide, which are suitably used in the form of an alcoholic solution.
The residual hydride content of the coated pigment is measured herein using the following hydrogen potential test method:
A dispersion of the silicon hydride-containing polysiloxane coated pigment obtained by the process of the present invention containing 20g of coated pigment is placed in a flask on a magnetic stirrer and 1 00ml of a 2% ethanolic solution of potassium hydroxide is added with stirring at ambient temperature. The hydrogen gas which is evolved is collected in a second flask at ambient temperature and pressure (25"C, lAt). The hydrogen gas released can therefore be volumetrically measured.
The process according to the present invention can be used as a first stage in the formation of cosmetic emulsions which incorporate pigments coated with silicon-hydride-containing polysiloxanes. Thus any hydrogen gas which would be produced on contact of the coated pigments with water or alcohol in the emulsion formulation is driven off at an early stage of the formulation process.
Thus according to a further aspect of the present invention there is provided a process for preparing a pigmented water-in-oil or oil-in-water emulsion cosmetic composition wherein the process comprises treating the pigment as described hereinabove, neutralisation of excess base with inorganic or organic acid, and subsequent addition of a polydiorganosiloxane-polyoxyalkylene copolymer containing at least one polydiorganosiloxane segment, water and other formulation ingredients. A preferred polydiorganosiloxane-polyoxyalkylene copolymer for use herein is cyclomethicone/dimethicone copolyol (90:10), commercially available from Dow Corning under the tradename DC3225C. Preferably the aqueous phase of the emulsion has a pH of less than about 6, preferably less than about 4.
The treated pigments prepared according to the process of the present invention are advantageously incorporated into the oil phase of water in silicone cosmetic foundation compositions comprising an aqueous/alcoholic solution of salicylic acid. The treated pigments prepared according to the process of the invention are advantageous from the viewpoint of reducing hydrogen gas generation in low pH environments.
The process of treating pigments according to the present invention is particularly valuable for maintaining the pigments in their original colloidal, non-agglomerated form. Hence according to a further aspect of the present invention there is provided a monoalkyl polysiloxane coated pigment in the form of a dispersion in a non-polar organic solvent and which has a residual silicon hydride content as measured by hydrogen potential of less than about 0.5ml H2/g of coated pigment, preferably less than about 0.lml H2/g of coated pigment and which has a particle size (volume average, Malvern Master Sizer Laser Diffraction) of less than about 1 micron.These pigment dispersions can be incorporated into cosmetic compositions containing water and/or alcohol, especially at acidic or alkaline pH, with the advantage that they do not react with the latter components to produce hydrogen gas.
Example I 20g of methicone coated iron oxide pigment was dispersed in 40g of cyclomethicone and reacted with a sufficient amount of a 2% ethanolic solution of KOH to give a coated pigment dispersion having a residual hydride content as measured by the hydrogen potential test method described hereinabove of less than 0.5ml H2/g of coated pigment.
Examplesll-VI The table below shows examples of cosmetic compositions of the present invention.
II/% III/% IV/% V/% VI/%
A
Cyclomethicone [DC 21330] 15.2 16.0 14.8 15.3 15.7
Silicone oil [DC 200/350 cs] 2 2 2 2 2
B
Mica 0.1 0.15 0.1 0.12 0.1
Titanium Dioxide grind* 8.25 9.6 14.2 7.85 8.5
C
Spheron P 1500 0.1 0.3 0.08 0.15 0.18
II/% III/% IV/% V/% W% D
Yellow iron oxide grind** 0.55 0.6 0.49 0.59 0.58
Red iron oxide grind*** 0.3 0.25 0.28 0.24 0.4
Black iron oxide grind**** 0.1 0.08 0.08 0.12 0.15
Cyclomethicone 1 1 1 1 1
E
Cyclomethicone/dimethicone 20 16.5 18.75 19.5 21.2 copolyol [90::10] [DC3225C]
F
Durachem 0.1 0.1 0.1 0.1 0.1
Waxenol 0.3 0.3 0.3 0.3 0.3
G
Cyclomethicone [DC 21330] 1 1.5 1 1.2 1
Thixin R 0.3 0.3 0.3 0.3 0.3
Ethylene Brassylate 0.1 0.1 0.1 0.1 0.1
H
Ethanol 4 5 5 6 5
Polyvinylpyrrolidone [Luviskol K 1 1.8 0.8 1.5 1.2 17] Salicylic acid 1 2 1.5 1 1
Dipropylene glycol 10 12 11 10 11 Deionised water ----- ------- to 100 ------- Na4 EDTA 0.1 0.1 0.1 0.1 0.1
Sodium Citrate 0.3 0.25 0.25 0.32 0.3
Glycerin 10 15 6 12 9 * Titanium dioxide grind contains 69% methicone coated titanium dioxide, 20% DC3225C and 11% DC21330 ** Yellow iron oxide grind contains 55% methicone coated yellow iron oxide, 28% DC3225C, 17% DC21330 *** Red iron oxide grind contains 70% methicone coated red iron oxide, 20% DC3225C, 10% DC21330 **** Black iron oxide grind contains 55% methicone coated black iron oxide, 29% DC3225C, 16% DC21330
The formulations of Examples II to VI can be prepared as follows. The various components listed in the Table have been segregated into groups, the constituents of each group being mixed together before being added to members of the remaining groups in accordance with the procedures set forth below.
In the first step, the mixture of components of phase A is stirred for approximately 5 minutes with sheer mixing until homogeneous. With high speed sheer mixing, the materials of phase B are added gradually to A and the batch is mixed for 20 minutes. Phases C and D are added and the resluting mixture is ground until fully dispersed.
130g of the resulting mixture is placed in a reaction vessel and 25ml of 2% wlv KOH in absolute ethanol is added and the contents of the reaction vessel is stirred for 30 minutes until all the hydrogen gas has evolved, i.e.
until the coated pigment dispersion has a residual hydride content of less than 0.5ml H2/g of coated pigment.
0.64g of citric acid is dissolved in Sml of absolute ethanol and added to the reaction vessel. The contents of the reaction vessel is stirred for another 30 minutes. The reaction mixture is heated to 950C, distilled to remove ethanol and then cooled to room temperature.
1 20g of this mixture is transferred to a stainless steel beaker and the components of phase E are added and stirred for 5 minutes until homogeneous. The mixture is heated to 900C in a water bath and phase F is added. When the waxes have melted, the stainless steel beaker is removed from the water bath and the contents cooled to 500C. Phase G is added and the mixture homogenised for 10 minutes. The mixture is then cooled to room temperature.
Phase H is prepared as follows. The sodium citrate is added to water and mixed until dissolved. The Na4EDTA is added with mixing until dissolved. The glycerin is added with mixing until homogeneous.
Phase I is prepared as follows. The PVP is added to ethanol on mixing until dissolved. Salicylic acid is then added on mixing. Propylene glycol is added until no crystals are present. When the crystals have dissolved, phase H is added very slowly to phase I and mixed.
The water phases H and I are added to the stainless steel beaker quickly whilst homogenising at a low speed, with stirring. When all of the water phases have been added, high sheer is applied to the batch for approximately 5 minutes to increase the viscosity of the final product.
The resulting make-up composition is ready for packaging.
The cosmetic compositions of the Examples exhibit improved product stability and reduced hydrogen gas generation.
Claims (12)
1. A process of treating pigments which have been coated with silicon
hydride-containing polysiloxanes wherein the process comprises
dispersing the coated pigment in a non-polar organic solvent, and
reacting the silicon hydride-containing polysiloxane coated pigment
with an aqueous or non-aqueous solution of organic or inorganic
base so as to provide a coated pigment dispersion having a residual
hydride content as measured by hydrogen potential of less than
about 0.5 ml H2/g of coated pigment.
2. A process according to Claim 1 wherein the residual hydride
potential is less than about 0.1 ml H2/g of coated pigment.
3. A process according to Claim 1 or 2 wherein the non-polar organic
solvent is selected from linear and cyclic polydiorganosiloxane
fluids, and mixtures thereof.
4. A process according to any of Claims 1 to 3 wherein the non-polar
organic solvent is cyclomethicone.
5. A process according to any of Claims 1 to 4 wherein the inorganic
base is selected from alkali metal hydroxides.
6. A process according to any of Claims 1 to 5 wherein the silicon
hydride-containing polysiloxane is a monoalkyl polysiloxane.
7. A process according to any of Claims 1 to 6 wherein the silicon
hydride-containing polysiloxane is methicone.
8. A process according to any of Claims 1 to 7 wherein the pigments
are selected from iron oxide, rutile titanium dioxide and anatase
titanium dioxide, and mixtures thereof.
9. Process for preparing a pigmented water-in-oil or oil-in-water
emulsion cosmetic composition wherein the process comprises the
treating the pigment according to the process of any of Claims 1 to
8, neutralisation of excess base with inorganic or organic acid, and
subsequent addition of a polydiorganosiloxane-polyoxyalkylene
copolymer containing at least one polydiorganosiloxane segment,
water and other formulation ingredients.
10. Process according to Claim 9 wherein the aqueous phase of the
emulsion has a pH of less than about 6, preferably less than about 4.
11. A monoalkyl polysiloxane coated pigment in the form of a
dispersion in a non-polar organic solvent and which has a residual
silicon hydride content as measured by hydrogen potential of less
than about 0.5ml H2/g of coated pigment, preferably less than about
0.1 ml H2/g of coated pigment and which has a particle size (volume
average, Malvern Master Sizer Laser Diffraction) of less than about
1 micron.
12. A cosmetic composition comprising the pigment of Claim 11 or
prepared according to the process of any of Claims 1 to 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9509527A GB2300629A (en) | 1995-05-11 | 1995-05-11 | Treating polysiloxane-coated pigment particles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9509527A GB2300629A (en) | 1995-05-11 | 1995-05-11 | Treating polysiloxane-coated pigment particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9509527D0 GB9509527D0 (en) | 1995-07-05 |
| GB2300629A true GB2300629A (en) | 1996-11-13 |
Family
ID=10774287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9509527A Withdrawn GB2300629A (en) | 1995-05-11 | 1995-05-11 | Treating polysiloxane-coated pigment particles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2300629A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999024001A1 (en) * | 1997-11-10 | 1999-05-20 | The Procter & Gamble Company | Skin care compositions and method of improving skin appearance |
| US6013270A (en) * | 1998-04-20 | 2000-01-11 | The Procter & Gamble Company | Skin care kit |
| DE102007044302A1 (en) * | 2007-09-17 | 2009-03-19 | Bühler PARTEC GmbH | Process for dispersing finely divided inorganic powders in liquid media using reactive siloxanes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61127767A (en) * | 1984-11-26 | 1986-06-16 | Daito Kasei Kogyo Kk | Hydrophobic powdery and granular material and production thereof |
| JPS6328442A (en) * | 1986-07-21 | 1988-02-06 | Shiseido Co Ltd | Water-in-oil type emulsion composition |
| JPH0892484A (en) * | 1994-09-19 | 1996-04-09 | Shiseido Co Ltd | Production of treated powder |
-
1995
- 1995-05-11 GB GB9509527A patent/GB2300629A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61127767A (en) * | 1984-11-26 | 1986-06-16 | Daito Kasei Kogyo Kk | Hydrophobic powdery and granular material and production thereof |
| JPS6328442A (en) * | 1986-07-21 | 1988-02-06 | Shiseido Co Ltd | Water-in-oil type emulsion composition |
| JPH0892484A (en) * | 1994-09-19 | 1996-04-09 | Shiseido Co Ltd | Production of treated powder |
Non-Patent Citations (3)
| Title |
|---|
| Derwent WPI Abstract 86-194167/30 & JP 61 127 767 A * |
| Derwent WPI Abstract 88-074376/11 & JP 63 028 442 A * |
| Derwent WPI Abstract 96-236269/24 & JP 08 092 484 A * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999024001A1 (en) * | 1997-11-10 | 1999-05-20 | The Procter & Gamble Company | Skin care compositions and method of improving skin appearance |
| US5997887A (en) * | 1997-11-10 | 1999-12-07 | The Procter & Gamble Company | Skin care compositions and method of improving skin appearance |
| US6013270A (en) * | 1998-04-20 | 2000-01-11 | The Procter & Gamble Company | Skin care kit |
| DE102007044302A1 (en) * | 2007-09-17 | 2009-03-19 | Bühler PARTEC GmbH | Process for dispersing finely divided inorganic powders in liquid media using reactive siloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9509527D0 (en) | 1995-07-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |