CN100413871C - 硅氧烷作为可汽化载体的应用 - Google Patents
硅氧烷作为可汽化载体的应用 Download PDFInfo
- Publication number
- CN100413871C CN100413871C CNB028210441A CN02821044A CN100413871C CN 100413871 C CN100413871 C CN 100413871C CN B028210441 A CNB028210441 A CN B028210441A CN 02821044 A CN02821044 A CN 02821044A CN 100413871 C CN100413871 C CN 100413871C
- Authority
- CN
- China
- Prior art keywords
- trisiloxanes
- methyl
- siloxanes
- application
- product
- 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.)
- Expired - Lifetime
Links
- -1 siloxanes Chemical class 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- HLCCCUYICFODBE-UHFFFAOYSA-N C[SiH2]O[SiH](O[SiH3])CC Chemical class C[SiH2]O[SiH](O[SiH3])CC HLCCCUYICFODBE-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000001166 anti-perspirative effect Effects 0.000 claims description 4
- 239000003213 antiperspirant Substances 0.000 claims description 4
- SKILBBKYUAWWMG-UHFFFAOYSA-N butyl-methylsilyloxy-silyloxysilane Chemical class C[SiH2]O[SiH](O[SiH3])CCCC SKILBBKYUAWWMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- NKNJFTJIZOSWNM-UHFFFAOYSA-N diethyl-bis(trimethylsilyloxy)silane Chemical class C[Si](C)(C)O[Si](CC)(CC)O[Si](C)(C)C NKNJFTJIZOSWNM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000000475 sunscreen effect Effects 0.000 claims description 3
- 239000000516 sunscreening agent Substances 0.000 claims description 3
- POJVZMLYQHGZBY-UHFFFAOYSA-N dipropyl-bis(trimethylsilyloxy)silane Chemical class CCC[Si](CCC)(O[Si](C)(C)C)O[Si](C)(C)C POJVZMLYQHGZBY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 230000008016 vaporization Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- PNECSTWRDNQOLT-UHFFFAOYSA-N dichloro-ethyl-methylsilane Chemical compound CC[Si](C)(Cl)Cl PNECSTWRDNQOLT-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035807 sensation Effects 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- 239000000230 xanthan gum Substances 0.000 description 3
- 235000010493 xanthan gum Nutrition 0.000 description 3
- 229940082509 xanthan gum Drugs 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical class CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000008406 cosmetic ingredient Substances 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 229940119170 jojoba wax Drugs 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 230000037312 oily skin Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940057874 phenyl trimethicone Drugs 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-N sodium;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O NGSFWBMYFKHRBD-UHFFFAOYSA-N 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
-
- 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
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q3/00—Manicure or pedicure preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/162—Organic compounds containing Si
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Abstract
本发明涉及硅氧烷作为可汽化的载体的应用，特别是硅氧烷在化妆品以及洗涤产品和护理产品中的应用，还涉及用于制备该硅氧烷和含该硅氧烷的组合物的方法。
Description
早就已知低分子硅氧烷可在化妆品中作为可汽化的载体应用(T.Koini，M.D.Berthiaume，A.Huber in：
-Journal，125，Jsahrgang4/99，22.)。特别是八甲基环四硅氧烷由于其较高的汽化速率和适意的皮肤感觉在化妆应用中有广泛的应用(Product Description SF1173，SF 1202，SF 1204，SF 1246 General Electric(GE)SiliconesCDS 4958-E/ENG/0797)。
近来基于生理相容性的观点对八甲基环四硅氧烷在化妆品中的应用提出了疑虑。在动物实验中发现在极端高的剂量下会降低生育力。因此近来的大量工作是通过合适的组分来代替化妆配剂中的八甲基环四硅氧烷，至今这些替代物质还未达到八甲基环四硅氧烷的效率和特性。一方面是作为八甲基环四硅氧烷的替代物质应用的十甲基环五硅氧烷的汽化速度明显低。另一方面线性的八甲基三硅氧烷和十甲基四硅氧烷未起到环硅氧烷所具有的柔滑和非油性的皮肤感觉的作用。
至今还未研制出一种可汽化的载体物质，该物质有足够挥发性，并且同时又有环硅氧烷的优良皮肤感觉，以致有可能在制备化妆品时不使用八甲基环四硅氧烷(＝D4)作为可汽化的载体。这里可汽化的载体可理解为其沸点在标准压力下低于250℃和按DIN 53249测定的汽化行为类似于D4。
在EP 0 980 885中描述了一种挥发性的硅氧烷的混合物，其可用于化妆品中。EP 980855的任务就是要找到一种挥发性的线性硅氧烷，按DIN 53249标准它可在30分钟之后汽化达80-85重量％。
由此，这些硅氧烷应比八甲基四环硅氧烷(＝D4)汽化的慢。
WO 98-32418中描述了一种透明的防汗剂凝胶，其中可含有EP980855的线性硅氧烷以及另外的环硅氧烷。
但是还未证实，具有与D4有可比挥发性的烷基硅氧烷是优选的或断定可作为D4的替代物。
与EP 980 855和WO 98-32418相反，本发明的目的是研制一种纯物质，它可特别在化妆品及其它清洁配剂中用作挥发性载体物质以替代D4，其中其汽化特性尽可能按近八甲基环四硅氧烷的汽化特性、在宽的温度范围内保持呈液态和其凝固点应在较低的的温度。有利的是，通过采用纯的各物质可减少化妆配剂中所含的物质的数目。由此可使不同物质之间的相互作用最小，以大大改进产品安全性和质量保证。也就是说优选的配剂是这样一种配剂，其中仅通过纯的形式的含量超过85％的本发明的线性烷基甲基硅氧烷来代替八甲基环四硅氧烷或具有可比汽化特性的线性全甲基化硅氧烷。
此外，本发明的可汽化的硅氧烷不含或含少量“增白剂”。“增白剂”意指在US 5 922 309中描述的在皮肤和织物上的白色残留物现象。
此外，本发明的目的是研制一种具有柔滑的非油性皮肤感觉和具有汽化特性的硅氧烷，该硅氧烷有类似八甲基环四硅氧烷的汽化特性或超过它。八甲基环四硅氧烷的凝固点为4℃，如配剂或原料在较高温度下运输、贮存和加工时会由于气候关系而出现问题。因此本发明的目的还在于研制一种具有较有利的较低凝固点的硅氧烷。此外，本发明的目的还在于研制一种与化妆原料有良好相容性的硅氧烷。
意外地发现，所选用的低分子量的线性的用短链烷基改性过的硅氧烷通过选择烷基而具有可控制的汽化特性，并且同时具有相应于环硅氧烷的柔滑的非油性的皮肤感觉。
本发明中所采用的硅氧烷包括下列化合物：
1，1，3，3，3-五甲基-1-乙基二硅氧烷、1，1，3，3-四甲基-1，3-二乙基二硅氧烷、1，1，3，3，3-五甲基-1-丙基二硅氧烷、1，1，3，3-四甲基-1，3-二丙基二硅氧烷、1，1，3，3，3-五甲基-1-丁基二硅氧烷、1，1，3，3-四甲基-1，3-二丁基二硅氧烷、1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷、1，1，1，5，5，5-六甲基-3，3-二乙基三硅氧烷、1，1，3，3，5，5-六甲基-1，5-二乙基三硅氧烷、1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷、1，1，1，5，5，5-六甲基-3，3-二丙基三硅氧烷或1，1，1，3，5，5，5-七甲基-3-丁基三硅氧烷作为在化妆品中的可汽化载体，要说明的是在丙基和丁基情况下可包括线性或分支的取代基。
本发明中的可汽化的载体意指引入化妆品或洗涤制剂中的具有合适的汽化特性的物质。该载体可使各种组分加入到这种制剂中，同时没有离析(Entmischung)现象。
该载体一方面必须具有一定的挥发性，但另一方面还要保证该整体产品的良好应用性。
优选的是1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷(CAS-Nr.29054-80-6)、1，1，1，5，5，5-六甲基-3，3-二乙基三硅氧烷、1，1，3，3，3-五甲基-1-丁基二硅氧烷以及1，1，1，3，5，5，5-七甲基-3-丁基三硅氧烷(CAS-Nr.18138-63-1)。最优选的硅氧烷是1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷(CAS-Nr.17861-60-8)。
本发明所应用的化合物其本身是已知的(W.Noll，Chemie undTechnologie der Silicone，2.Auflage，Verlag Chemie Weinheim1968，第216页起)。在优选的方法中，它们可通过在合适的SiH官能的硅氧烷上加成有针对性选择的烯烃和需要时接着进行平衡反应来制备。另一制备方法是通过经金属有机试剂(如格式试剂或WURTZ试剂)将烷基取代基引入氯硅烷中，接着水解按该反应产生的烷基氯硅烷，优选是甲基烷基二氯硅烷，并且与其它甲基氯硅烷的水解产物平衡化。
本发明所应用的硅氧烷的特征是其凝固点远低于水的冰冻点，由此不仅方便于运输还方便于在化妆品中引入和应用。
将本发明所用的硅氧烷加工到化妆品中，并由独立的试验人员对其作皮肤感觉评定。在这种情况下，皮肤感觉的评定为较好于应用十甲基环五硅氧烷的情况。与此相反，与应用八甲基环四硅氧烷相比无明显差别。
在一个优选的方案中，本发明所应用的化合物可通过蒸馏由六甲基二硅氧烷、1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷以及低聚化合物组成的混合物来制得，其中下面的同系物(1，1，1，3，5，7，7，7-八甲基-3，5-二乙基四硅氧烷)的沸点＞220℃。用于此反应的硅烷是二甲基二氯硅烷的直接合成中产生的副产品(H.H.Moretto，M.Schulze，G.Wagner，in：Ullmann’s Encyclopedia of IndustrialChemistry，Sixth Edition，1988，Wiley-VCH，Weinheim)。通过甲基乙基二氯硅烷与三甲基氯硅烷的共水解产生例如合适的可通过蒸馏处理以生成1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷的混合物。意外地发现，在这种方案中，由共水解后的副产物的复杂的混合物开始，通过平衡反应和简单的蒸馏可得到高纯的确定形式的本发明所应用的产物。另外，由1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷以及低聚化合物组成的混合物可由甲基乙基二氯硅烷的水解并接着与六甲基二硅氧烷的酸催化平衡反应来制得(G.Koerner in：Silicone-Chemie und Technologie，Symposium，Vulkan-VerlagEssen 1988，第3页)。
同样优选的是，本发明的硅氧烷可通过在三甲基甲硅氧烷基封端的甲基氢聚硅氧烷或环甲基氢硅氧烷上以金属催化加成(氢化硅烷化)1-烯烃，再经与六甲基二硅氧烷的酸催化平衡反应来制备(BogdanMarciniec(Hrsg.)Comprehensive Hanbook on Hydrosilylation，Pergamon Press，Oxford，1992，第99页起)。适用的金属是Ni、Rh、Ru、或Pt，优选是Pt，可以胶态金属本身，其盐或表观氧化价为0-VI的配合物形式使用。
此外，本发明还涉及至少一种上述硅氧烷在选自下列的组合物中的应用：化妆品、皮肤护理产品、防晒产品、头发护理产品、除臭剂、防汗剂、装饰性化妆品、唇膏、口护理产品和指甲护理产品。此外，本发明还涉及上述硅氧烷之一在织物的化学洗涤中的应用。此外，本发明还涉及含有用于产品的通常的活性剂或助剂以及含有上述硅氧烷之一的产品组合物。例如这类产品组合物是前述的制剂。在前述的应用及产品组合物中，本发明所应用的硅氧烷的适用量按该制剂或产品组合物的总重量计为0.01-99重量％。优选的适用量为0.5-70重量％，特别优选的适用量为1.0-60重量％。
优选的是本发明的上述硅氧烷在所有种类的化妆品中的应用。优选该硅氧烷以0.01-99％的量作为可汽化的载体用于化妆品中，如去臭剂、防汗剂、装饰性化妆品、乳剂、洗剂、皮肤护理油、洗发剂、调理剂、喷剂、气溶胶、扑粉、防晒产品、凝胶或膏剂等。
特别优选是在这些制剂中绝不使用其它环硅氧烷。
本发明所用的硅氧烷与通常的化妆原料有极好的相容性。它们不仅可与植物油如葵花籽油、鳄梨油或霍霍巴油、还可与酯如异丙基十四烷酸酯、乙基己基棕榈酸酯或异壬基异壬酸酯混合。此外，本发明的硅氧烷可溶于醇如乙醇和异丙醇以及按INCI所列的非环硅氧烷如二甲基聚硅氧烷(Dimethicone)、苯基三甲基聚硅氧烷(PhenylTrimethicone)或双-苯基丙基-聚二甲基硅氧烷中。
下面的实施例用来说明本发明物质的应用，但不限制作为最可能的D4-替代物的应用可能性。
实施例
实施例1
制备1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷
在配置有底部排出口、搅拌器、温度计、回流冷凝器和滴液漏斗的用水冷却的烧瓶中加有3900g水，在搅拌下向其中加入1430g(10摩尔)甲基乙基二氯硅烷。调节加料速度将温度限制到最大40℃。结束加料后，停止搅拌，并在形成分明的相分离后，分出下层的含水盐酸相并弃去。该上层的油相用水洗涤一次，并接着转移到配置有搅拌器、温度计、水分离器和回流冷凝器的烧瓶中。在该油相中加入3240g(20摩尔)六甲基二硅氧烷和40g(0.41摩尔)的98-100％的硫酸。将该混合物加热到回流温度以缩合硅烷醇基以及去除其余的水。经2小时回流后，加入10g(0.047摩尔)全氟丁烷磺酸，并在100℃下继续搅拌该反应混合物4小时。在冷却到70℃以下后，加入80g纯碱和15g水和3g的25％的氨溶液以进行中和，继续搅拌1小时，并在检验无酸后重新加热到回流温度。经1小时回流后进行冷却和过滤。由此得到3820g粗产物，它由58％六甲基二硅氧烷、23％1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷和低聚硅氧烷组成，经精馏后得到717g沸点为169-172℃的98％的1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷。釜底物和分离出的六甲基硅氧烷可再送入平衡反应中。
实施例2
制备1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷
在配置有搅拌器和温度计的可加热的4升搪瓷压热釜中加有2000g(＝30摩尔SiH)在工业规模制备线性的三甲基甲硅烷氧基封端的甲基氢聚硅氧烷时产生的蒸馏物，并在其上充有氮气，该蒸馏物由75％的含平均环大小为4.8DH单位的环甲基氢硅氧烷和25％的平均链长为3(＝MeSiHO)-单位的三甲基甲硅烷氧基封端的甲基氢硅氧烷组成。压热釜中的压力用真空泵减至100mbar，并将压热釜中的含有物加热至65℃，将1g含2％铂的市售Pt0辛醛/辛醇配合物(Gelest)用20ml六甲基二硅氧烷稀释并被吸入压热釜中，然后将压力重新降到100mbar。接着如此从钢瓶中导入丙烯，以使通过几乎立即可显示出的放热反应不使压力超过2bar和不使温度超过130℃。在放热反应降低后，再在130℃和2bar丙烯压力下搅拌1小时，使压热釜卸压和排气。由此制得3300g SiH含量＜0.01mmol/g的加合物。
在配置有搅拌器、温度计、水分离器、回流冷凝器和氮覆盖的烧瓶中，加有658g(6摩尔DProp(＝丙基MeSiO)n)以这种方法制得的产物和1458g(9摩尔)六甲基二硅氧烷，添加102g BleicherdeTonsil Standerd 310 FF(Südchemie)，并在水分离器上于釜温为约100℃下搅拌6小时、冷却和过滤。由此制得2100g由62％六甲基二硅氧烷、14％1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷和24％低聚硅氧烷组成的粗产物，经精馏得410g沸点为192-194℃的98％的1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷。釜底物和分离出的六甲基二硅氧烷可再送入平衡反应中。
实施例3
制备1，1，1，3，3-五甲基-3-丁基二硅氧烷
在氮气氛下，在配置有搅拌器和温度计的4升可加热的搪瓷压热釜中加有2010g(＝30摩尔SiH)1，1，3，3-四甲基二硅氧烷。压热釜的压力用真空泵降至250mbar，并将其内含物加热到65℃，再将1g含2％铂的市售Pt0辛醛/辛醇配合物(Gelest)用20ml六甲基二硅氧烷稀释，并被吸入压热釜中。接着如此从钢瓶中导入1-丁烯，以使通过几乎立即可显示出的放热反应不使压力超过2bar和温度超过130℃。在放热反应降低后，抽出形成的2-丁烯直到100mbar，接着重新引入1-丁烯，并在130℃和2bar的丁烯压力下再搅拌1小时，使压热釜减压并放气达100mbar。由此制得3500g SiH含量＜0.01mmol/g的加合物。
在配置有搅拌器、温度计、水分离器、回流冷凝器和氮覆盖的烧瓶中加有984g加合物(8mol MButyl(＝丁基-Me2SiO0.5))和1312g(8摩尔)六甲基二硅氧烷，再加入0.1％硫酸和0.05％全氟丁烷磺酸，在釜温70℃下用20g Calzinierter纯碱、3g水和0.5g的25％的NH3-溶液中和4小时，蒸馏到110℃，经冷却和过滤。由此制得1950g由35％六甲基二硅氧烷、47％1，1，1，3，3-五甲基-3-丁基二硅氧烷和17％1，1，3，3-四甲基-1，3-二丁基-二硅氧烷组成的粗产物，经精馏得到810g沸点为166-169℃的97％的1，1，1，3，3-五甲基-3-丁基二硅氧烷。釜底物和分离出的六甲基二硅氧烷可再送入平衡反应中。
实施例4
汽化特性
在下面的表1和图1中是按DIN 53249测定的八甲基环四硅氧烷、十甲基环五硅氧烷和实施例1和3的汽化特性，是以不汽化的残余物的％给出的。
表1按DIN 53249测定的以剩余的硅氧烷残余物表示的汽化特性
| 时间[min] | 八甲基环四硅氧烷[％] | 十甲基环五硅氧烷[％] | 实施例1[％] | 实施例3[％] |
| 051015202530354050607090120150 | 10068.337.411.40000 | 10070.239.614.51.20 | 10059.723.92.80.60.10.10.1 | 100826343251130 |
与八甲基环四硅氧烷相比，十甲基环五硅氧烷的汽化明显较慢，由此在涂用含十甲基环五硅氧烷的制剂时，在皮肤上出现油性的湿的感觉。在应用实施例化合物1时就避免了这种感觉，该化合物的汽化特性类似于八甲基环四硅氧烷。此外，含实施例化合物1的制剂产生一种非常舒适的柔滑性的非油性和柔和的皮肤感觉。
实施例化合物2的挥发性在八甲基环四硅氧烷和十甲基环五硅氧烷之间，当需要挥发性处于八甲基环四硅氧烷和十甲基环五硅氧烷之间时，可采用实施例化合物2。含实施例化合物2的制剂具有较明显的油性的皮肤感觉。
通过混合本发明的硅氧烷，可有目的地调节到八甲基环四硅氧烷达到的需求的特定的挥发性或是偏离D4的特定需要的皮肤感觉。
实施例5
制备化妆喷雾剂
在这类组合物中的典型助剂是例如描述于下列文献中的物质：A.Domsch：Die kosmetischen
Bd.Iu.II4.Aufl.Verl.für chem.Industrie，H.Ziolkowsky KG，Augsburg以及在International Cosmetic Ingredient Dictionary and Handbook 7thEd.1997 by J.A.Wenniger，G.N.McEwen Vol.1-4by TheCosmetic，Toiletry and Fragrance Association Washington DC。
相1：PEG-8蜂蜡(6.0％)，实施例化合物1(5.5％)，霍霍巴油(5.5％)，椰油甘油酯(5.0％)，油基芥酸酯(4.0％)。
相2：水(78.6％)，瓜耳胶羟丙基trimonium氯化物(0.3％)，黄原胶(0.1％)，乳酸钠(2.0％)，Phenonip(0.4％)。
将该两相互相分开加热到65℃。然后在强烈搅拌下将热的相1加到热的相2中，并且60℃下搅拌10分钟。在降低搅拌速度下达到冷却。
实施例6
制备化妆基础配料
相1：水(适量)，黄原胶(0.3％)，丙二醇(5.0％)，三乙醇胺(1.4％)。
相2：甘油硬脂酸酯SE(3.9％)，异壬基异壬酸酯(3.0％)，硅油SFGE Silicones(8.5％)，实施例化合物2(3％)，二甲基聚硅氧烷SF
GE Silicones(1.0％)，硬脂酸(3.9％)。
相2：甘油硬脂酸酯SE(3.9％)，异壬基异壬酸酯(3.0％)，二-苯基丙基二甲基聚硅氧烷(SF
GE Silicones)(8.5％)，实施例化合物2(3％)，二甲基聚硅氧烷(5000 cStk)SF
GESilicones(树胶)(1.0％)，硬脂酸(3.9％)。
相3：颜料混合物(3.3％)。
相4：防腐剂(适量)。
制备：在强烈搅拌下将黄原胶分散在水中。加入其余的相1的组分，并加热到75-77℃。同样在强烈搅拌下混合相2的组分，并加热到75-77℃。然后将相2加到相1中，并在至少70℃匀质化5分钟。接着加入相3，重新匀质化，并冷却到50℃。最后加入防腐剂，并在慢慢搅拌下冷却到25℃。
实施例7
制备乳剂基料
相1：C30-45烷基二甲基聚硅氧烷(SF
GE Silicones)(11.0％)，Cetearyl Methicone(SF
GE Silicones)(4.0％)，硬脂酸(11.5％)，实施例化合物3(4.0％)，羊毛脂(3.0％)。
相2：水(适量)，丙二醇(3.4％)，三乙醇胺(2.9％)，防腐剂(适量)。
相3：聚甲基倍半硅氧烷(Polyme thylsilsequioxane)(Tospearl
GE Silicones)(10％)，颜料混合物(18％)。
制备：将相1和相2分别加热到70℃。然后在搅拌下将相2加到相1中，直到该混合物冷却下来。然后在慢搅拌下将该混合物加到相3中。
Claims (5)
1. 1，1，1，5，5，5-六甲基-3，3-二乙基三硅氧烷、1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷、1，1，3，3，5，5-六甲基-1，5-二乙基三硅氧烷、1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷、1，1，1，5，5，5-六甲基-3，3-二丙基三硅氧烷或1，1，1，3，5，5，5-七甲基-3-丁基三硅氧烷以单个化合物或以混合物的形式在化妆品中作为可汽化的载体的应用，要说明的是在丙基和丁基情况下，可包括线性或分支的取代基。
2. 权利要求1的1，1，1，3，5，5，5-七甲基-3-乙基三硅氧烷的应用。
3. 权利要求1的1，1，1，3，5，5，5-七甲基-3-丙基三硅氧烷的应用。
4. 权利要求1的1，1，1，3，5，5，5-七甲基-3-丁基三硅氧烷的应用。
5. 权利要求1中至少一种硅氧烷在选自下列组合物中的应用：皮肤护理产品、防晒产品、头发护理产品、除臭剂、防汗剂、装饰性化妆品、唇膏、口护理产品和指甲护理产品。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10155512.1 | 2001-11-13 | ||
| DE10155512 | 2001-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1575293A CN1575293A (zh) | 2005-02-02 |
| CN100413871C true CN100413871C (zh) | 2008-08-27 |
Family
ID=7705469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028210441A Expired - Lifetime CN100413871C (zh) | 2001-11-13 | 2002-11-12 | 硅氧烷作为可汽化载体的应用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7374771B2 (zh) |
| EP (1) | EP1472263B1 (zh) |
| JP (1) | JP4174595B2 (zh) |
| CN (1) | CN100413871C (zh) |
| AT (1) | ATE338049T1 (zh) |
| DE (1) | DE50208032D1 (zh) |
| ES (1) | ES2272814T3 (zh) |
| HK (1) | HK1073314A1 (zh) |
| WO (1) | WO2003042221A1 (zh) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040197284A1 (en) | 2003-04-04 | 2004-10-07 | Frederic Auguste | Cosmetic composition comprising a volatile fatty phase |
| JP5188004B2 (ja) * | 2004-02-17 | 2013-04-24 | 東レ・ダウコーニング株式会社 | 液状中鎖アルキル変性ポリジメチルシロキサン精製品の製造方法および化粧料 |
| US8394394B2 (en) | 2004-05-26 | 2013-03-12 | L'oréal | Mousse formulations |
| FR2873571B1 (fr) * | 2004-07-28 | 2006-11-24 | Oreal | Composition cosmetique pour le maquillage des fibres keratiniques comprenant une huile alkyltrisiloxane volatile |
| FR2873581B1 (fr) * | 2004-07-28 | 2006-11-24 | Oreal | Composition cosmetique comprenant au moins une huile lineaire alkyltrisiloxane volatile |
| FR2873582B1 (fr) * | 2004-07-28 | 2006-11-24 | Oreal | Composition cosmetique comportant au moins une cire apolaire et au moins une huile alkyltrisiloxane volatile |
| FR2873580B1 (fr) * | 2004-07-28 | 2006-11-24 | Oreal | Composition cosmetique comprenant un melange d'au moins une huile siliconee cyclique et d'au moins une huile alkyltrisiloxane volatile |
| FR2873583B1 (fr) * | 2004-07-28 | 2006-11-24 | Oreal | Composition cosmetique comprenant une emulsion a phase continue huileuse comprenant au moins une huile alkyltrisiloxane volatile |
| WO2006013411A1 (en) * | 2004-07-28 | 2006-02-09 | L'oreal | Cosmetic composition for keratin fibers comprising an alkyltrisiloxane |
| WO2006013412A1 (en) * | 2004-07-28 | 2006-02-09 | L'oreal | Cosmetic composition comprising an apolar wax and an alkyltrisiloxane |
| WO2006013415A1 (en) * | 2004-07-28 | 2006-02-09 | L'oreal | Cosmetic composition comprising a cyclic silicone and an alkyltrisiloxane |
| WO2006013414A1 (en) * | 2004-07-28 | 2006-02-09 | L'oreal | Cosmetic composition comprising an emulsion comprising an alkyltrisiloxane |
| WO2006013413A1 (en) * | 2004-07-28 | 2006-02-09 | L'oreal | Cosmetic composition comprising a volatile linear alkyltrisiloxane |
| US7758848B2 (en) | 2004-10-22 | 2010-07-20 | L'oreal | Cosmetic composition containing a polyorganosiloxane polymer |
| US7871634B2 (en) | 2005-08-11 | 2011-01-18 | L'oréal | Cosmetic compositions useful for lengthening lashes |
| US7863361B2 (en) * | 2005-11-15 | 2011-01-04 | Momentive Performance Materials Inc. | Swollen silicone composition, process of producing same and products thereof |
| US8017687B2 (en) | 2005-11-15 | 2011-09-13 | Momentive Performance Materials Inc. | Swollen silicone composition and process of producing same |
| US20070112078A1 (en) * | 2005-11-15 | 2007-05-17 | Ian Procter | Silicone antifoam composition |
| US20070128233A1 (en) * | 2005-12-05 | 2007-06-07 | L'oreal | Cosmetic composition having a unique cushiony texture |
| US20070160547A1 (en) * | 2006-01-11 | 2007-07-12 | Janet Duffy | Method of applying a composition |
| US8313735B2 (en) | 2006-10-30 | 2012-11-20 | Oreal | Long-wearing cosmetic product system for providing extended shine and gloss |
| US20080102049A1 (en) * | 2006-10-30 | 2008-05-01 | L'oreal | Long-wearing cosmetic product system having high shine and gloss |
| US8715634B2 (en) | 2006-10-24 | 2014-05-06 | L'oreal | Volumizing compositions |
| MX2007016506A (es) | 2006-12-29 | 2008-10-28 | Oreal | Composicion que contiene un polimero de poliorganosiloxano un agente espesante y al menos un alcohol volatil. |
| CN101627095A (zh) * | 2007-01-12 | 2010-01-13 | 莫门蒂夫性能材料股份有限公司 | 施用组合物的方法 |
| US8658141B2 (en) | 2007-01-12 | 2014-02-25 | L'oreal | Cosmetic composition containing a block copolymer, a tackifier, a silsesquioxane wax and/or resin |
| HUP0900072A2 (hu) | 2009-02-06 | 2010-09-28 | Egis Gyogyszergyar Nyilvanosan | Transzdermális gyógyszerkészítmények |
| US20090092567A1 (en) * | 2007-10-05 | 2009-04-09 | L'oreal S.A. | Oil-containing compositions exhibiting reduced feathering |
| US20100003201A1 (en) * | 2008-07-07 | 2010-01-07 | Momentive Performance Materials, Inc. | Silicone composition |
| US20110020256A1 (en) | 2009-06-29 | 2011-01-27 | L'oreal S.A. | Composition comprising a sugar silicone surfctant and a oil-soluble high carbon polar modified polymer |
| BRPI1003179A2 (pt) | 2009-06-29 | 2013-07-30 | Oreal | composiÇço que compreende um poliol, um tensoativo siliconado de aÇécar e um polÍmero modificado polar lipossolével com teor elevado de carbono |
| EP3219364A1 (en) | 2009-06-29 | 2017-09-20 | L'oreal | Composition comprising the reaction product of a hyperbranched polyol and of an oil-soluble polar modified polymer |
| US8652451B2 (en) | 2009-06-29 | 2014-02-18 | L'oreal | Composition comprising a sugar silicone surfactant and a oil-soluble polar modified polymer |
| US8647611B2 (en) | 2009-06-29 | 2014-02-11 | L'oréal | Composition containing a polyol and a reaction product |
| EP2322139A3 (en) | 2009-06-29 | 2014-03-26 | L'oreal S.A. | Composition comprising a polyol and an oil-soluble high carbon polar modified polymer |
| BRPI1002597A2 (pt) | 2009-06-29 | 2012-03-13 | L'oreal S.A. | Composição que compreende pelo menos um polímero polar modificado solúvel em óleo |
| US8337870B2 (en) * | 2009-12-15 | 2012-12-25 | Young Pharmaceuticals, Inc. | Low toxicity topical active agent delivery system |
| US9078835B2 (en) | 2009-12-18 | 2015-07-14 | L'oreal | Composition containing an aqueous dispersion of polyurethane and an oil-soluble polar modified polymer |
| EP2359806A1 (en) | 2009-12-18 | 2011-08-24 | L'oreal S.A. | Composition containing an aqueous dispersion of polyurethane and an oil-soluble polar modified polymer |
| EP2356981B1 (en) | 2009-12-18 | 2019-03-20 | L'Oréal SA | Mascara containing aqueous dispersion of polyurethane and a hard wax |
| JP2013525500A (ja) | 2010-05-05 | 2013-06-20 | ロレアル | アクリル増粘剤を含有する化粧品用組成物 |
| EP2566440A2 (en) | 2010-05-05 | 2013-03-13 | L'oreal, S.A. | Compositions containing acrylic thickener and oil |
| US8933134B2 (en) | 2010-06-09 | 2015-01-13 | L'oreal | Compositions containing agar and a softening agent |
| EP2409702A1 (en) | 2010-07-21 | 2012-01-25 | Bayer Innovation GmbH | Combination of siloxane and active ingredient for treating dental disorder of hard tissues |
| US8747868B2 (en) | 2010-12-30 | 2014-06-10 | L'oreal | Reaction product of a polar modified polymer and an alkoxysilane and a composition containing the reaction product |
| US8765110B2 (en) | 2010-12-30 | 2014-07-01 | L'oreal | Composition containing an alkoxysilane and hyaluronic acid |
| US20120219516A1 (en) | 2011-02-25 | 2012-08-30 | L'oreal S.A. | Cosmetic compositions having long lasting shine |
| BR112014007573B1 (pt) | 2011-09-30 | 2018-11-13 | L'oreal | emulsão água-em-óleo-em-água, composição cosmética, métodos de maquilagem e método de fabricação de uma emulsão água-em-óleo-em-água |
| EP3233047B1 (en) | 2014-12-18 | 2022-01-05 | L'oreal | Compositions and methods for improving the appearance of the skin |
| US10426722B2 (en) | 2015-12-29 | 2019-10-01 | L'oreal | Compositions containing an alkylated silicone acrylate copolymer |
| US10835479B2 (en) | 2015-12-31 | 2020-11-17 | L'oreal | Systems and methods for improving the appearance of the skin |
| US10292922B2 (en) | 2015-12-31 | 2019-05-21 | L'oreal | Silicone-wax dispersion compositions for removing cosmetic films |
| WO2018144533A1 (en) | 2017-01-31 | 2018-08-09 | L'oreal | Long-wear compositions containing silicone acrylate copolymer and silicone elastomer resin |
| US20180214369A1 (en) | 2017-01-31 | 2018-08-02 | L'oréal | Long-wear compositions containing silicone resin and silicone elastomer resin |
| US11058627B2 (en) | 2017-01-31 | 2021-07-13 | L'oreal | Long-wear compositions containing silicone acrylate copolymer and surface-treated pigment |
| US10952954B2 (en) | 2017-09-29 | 2021-03-23 | L'oreal | Cosmetic compositions capable of forming a multilayer structure after application to a keratinous material |
| US10881601B2 (en) | 2017-09-29 | 2021-01-05 | L'oreal | Cosmetic compositions capable of forming a multilayer structure after application to a keratinous material |
| US11472925B2 (en) | 2018-03-22 | 2022-10-18 | Momentive Performance Materials Inc. | Silicone polymer |
| WO2021021978A1 (en) | 2019-07-31 | 2021-02-04 | L'oreal | Compositions containing copolymer of vinylpyrrolidone and acrylic acid and film forming agent |
| WO2021222764A1 (en) | 2020-04-30 | 2021-11-04 | L'oreal | Water-in-oil emulsions containing surfactant, silicone gum and/or latex, and siloxysilicate resin |
| FR3113588B1 (fr) | 2020-08-28 | 2023-06-09 | Oreal | Emulsions eau dans huile contenant un tensioactif a faible hlb, une gomme de silicone et une resine de siloxysilicate |
| FR3112949B1 (fr) | 2020-07-29 | 2023-02-24 | Oreal | Emulsions eau dans l’huile contenant du latex et une resine de siloxysilicate |
| US20230172831A1 (en) * | 2020-05-26 | 2023-06-08 | Shin-Etsu Chemical Co., Ltd. | Cosmetic |
| WO2022005833A1 (en) | 2020-06-30 | 2022-01-06 | L'oreal | Cosmetic compositions capable of forming a multilayer structure after application to a keratinous material containing a combination of silicone resins |
| FR3113598B1 (fr) | 2020-08-26 | 2022-12-02 | Oreal | Compositions cosmetiques capables de former une structure multicouche apres application a une matiere keratineuse contenant une combinaison de resines de silicone |
| FR3113587A1 (fr) | 2020-08-27 | 2022-03-04 | L'oreal | Compositions de gel comprenant de la silice hydrophobe et un copolymère formé à partir de monomère acrylique d’acide sulfonique |
| WO2022026085A1 (en) | 2020-07-31 | 2022-02-03 | L'oreal | Gel compositions comprising hydrophobic silica and a copolymer formed from sulfonic acid acrylic monomer |
| WO2022148990A1 (en) | 2021-01-07 | 2022-07-14 | L'oreal | Anhydrous eyelash compositions containing silicone resins and plasticizer |
| FR3120525B1 (fr) | 2021-03-15 | 2024-02-09 | Oreal | Compositions pour cils contenant du sucre |
| WO2022261019A1 (en) | 2021-06-07 | 2022-12-15 | L'oreal | Three-part makeup remover compositions |
| FR3125966A1 (fr) | 2021-08-03 | 2023-02-10 | L'oreal | Compositions démaquillantes en trois parties |
| WO2023278383A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Lipsticks having natural oil, fatty alcohol wax and filler particles |
| FR3127405A1 (fr) | 2021-09-30 | 2023-03-31 | L'oreal | ROUGES à LèVRES COMPORTANT UNE HUILE NATURELLE, UNE CIRE D’ALCOOL GRAS ET DES PARTICULES DE CHARGE |
| FR3130134B1 (fr) | 2021-12-14 | 2023-12-22 | Oreal | Émulsions eau dans huile comprenant un tensioactif, un polymère acrylique et un organosiloxane |
| FR3130136A1 (fr) | 2021-12-14 | 2023-06-16 | L'oreal | Émulsions eau dans l’huile comprenant un tensioactif, un polymère vinylique soluble dans l’eau et un organosiloxane |
| WO2023122192A2 (en) | 2021-12-21 | 2023-06-29 | L'oreal | Long-wear compositions containing acid-functional silicone elastomer and block copolymer |
| FR3132844A1 (fr) | 2022-02-21 | 2023-08-25 | L'oreal | Compositions longue tenue contenant un élastomère de silicone à fonction acide et un copolymère séquencé |
| JP2023150349A (ja) * | 2022-03-31 | 2023-10-16 | 信越化学工業株式会社 | 分岐型オルガノポリシロキサン及びその製造方法 |
| WO2024003588A1 (en) | 2022-06-30 | 2024-01-04 | L'oreal | Water-in-oil emulsions suitable as eyeliners |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520737A (en) * | 1978-08-01 | 1980-02-14 | Shiseido Co Ltd | Cosmetic |
| US5922083A (en) * | 1995-04-03 | 1999-07-13 | Procter & Gamble Company | Detergent composition comprising a mutant amylase enzyme and oxygen bleaching agent |
| CN1247868A (zh) * | 1998-08-20 | 2000-03-22 | 瓦克化学有限公司 | 挥发性线形硅氧烷混合物 |
| JP2000204398A (ja) * | 1999-01-11 | 2000-07-25 | Shin Etsu Chem Co Ltd | 洗浄剤 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376087A (en) | 1981-05-26 | 1983-03-08 | Rca Corporation | Processing of video discs |
| US5002762A (en) | 1988-03-16 | 1991-03-26 | The Procter & Gamble Company | Volatile silicons in household and cosmetic products |
| US5084577A (en) | 1988-03-16 | 1992-01-28 | The Procter & Gamble Company | Volatile silicon compounds |
| FR2746102B1 (fr) * | 1996-03-18 | 1998-04-30 | Colorants siloxaniques, compositions les contenant et utilisations | |
| US5925338A (en) | 1997-01-29 | 1999-07-20 | The Gillette Company | Clear antiperspirant or deodorant gel composition with volatile linear silicone to reduce staining |
| FR2777287A1 (fr) * | 1998-04-09 | 1999-10-15 | Rhodia Chimie Sa | Procede de preparation de silicones a fonction(s) arylalkyles(s) par hydrosilylation |
| FR2771003B1 (fr) | 1997-11-19 | 2000-03-03 | Rhodia Chimie Sa | Melanges de silicones volatils non cycliques et compositions cosmetiques a base desdits melanges |
| US5922309A (en) | 1997-12-23 | 1999-07-13 | Cheesebrough-Pond's Usa Co. | Non-whitening underarm compositions |
| JP3954212B2 (ja) | 1998-08-20 | 2007-08-08 | 旭硝子セラミックス株式会社 | アルミナ・ジルコニア・シリカ溶融耐火物の評価方法 |
| US20040197284A1 (en) * | 2003-04-04 | 2004-10-07 | Frederic Auguste | Cosmetic composition comprising a volatile fatty phase |
| JP5188004B2 (ja) * | 2004-02-17 | 2013-04-24 | 東レ・ダウコーニング株式会社 | 液状中鎖アルキル変性ポリジメチルシロキサン精製品の製造方法および化粧料 |
-
2002
- 2002-11-12 AT AT02803009T patent/ATE338049T1/de not_active IP Right Cessation
- 2002-11-12 US US10/495,343 patent/US7374771B2/en not_active Expired - Lifetime
- 2002-11-12 JP JP2003544057A patent/JP4174595B2/ja not_active Expired - Lifetime
- 2002-11-12 DE DE50208032T patent/DE50208032D1/de not_active Expired - Lifetime
- 2002-11-12 ES ES02803009T patent/ES2272814T3/es not_active Expired - Lifetime
- 2002-11-12 EP EP02803009A patent/EP1472263B1/de not_active Expired - Lifetime
- 2002-11-12 WO PCT/EP2002/012596 patent/WO2003042221A1/de active IP Right Grant
- 2002-11-12 CN CNB028210441A patent/CN100413871C/zh not_active Expired - Lifetime
-
2005
- 2005-07-13 HK HK05105966.4A patent/HK1073314A1/xx not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520737A (en) * | 1978-08-01 | 1980-02-14 | Shiseido Co Ltd | Cosmetic |
| US5922083A (en) * | 1995-04-03 | 1999-07-13 | Procter & Gamble Company | Detergent composition comprising a mutant amylase enzyme and oxygen bleaching agent |
| CN1247868A (zh) * | 1998-08-20 | 2000-03-22 | 瓦克化学有限公司 | 挥发性线形硅氧烷混合物 |
| JP2000204398A (ja) * | 1999-01-11 | 2000-07-25 | Shin Etsu Chem Co Ltd | 洗浄剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE338049T1 (de) | 2006-09-15 |
| WO2003042221A1 (de) | 2003-05-22 |
| EP1472263A1 (de) | 2004-11-03 |
| EP1472263B1 (de) | 2006-08-30 |
| JP4174595B2 (ja) | 2008-11-05 |
| US7374771B2 (en) | 2008-05-20 |
| DE50208032D1 (de) | 2006-10-12 |
| CN1575293A (zh) | 2005-02-02 |
| ES2272814T3 (es) | 2007-05-01 |
| JP2005509041A (ja) | 2005-04-07 |
| US20050069564A1 (en) | 2005-03-31 |
| HK1073314A1 (en) | 2005-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100413871C (zh) | 硅氧烷作为可汽化载体的应用 | |
| JP3631941B2 (ja) | 化粧品での使用のための安定したクリーム状ゲル組成物、その製造方法および化粧品 | |
| EP1057872B1 (en) | Method of treating cellulosic or synthetic nonwoven substrates | |
| EP0982022B1 (en) | Fragrance releasing non-volatile polymeric siloxanes | |
| EP0125779B1 (en) | Skin care formulations comprising a water-in-mineral oil emulsion and siloxane compositions therefor | |
| EP1219289A2 (en) | Cosmetic compositions containing silicone gel | |
| EP0915123B1 (en) | Terminating post cure of silicone elastomers with amino acid esters | |
| EP1427772B1 (en) | Clear silicone microemulsions | |
| JP2000273308A (ja) | ビタミン強化シリコーンエラストマーの製造方法 | |
| KR20140146191A (ko) | 유기폴리실록산 겔 | |
| CA2126813A1 (en) | Water-in-volatile silicone emulsion gel cosmetic | |
| US10053543B2 (en) | Polyorganosiloxane gels having glycoside groups | |
| EP0478284B1 (en) | Organic silicon compounds and cosmetic compositions | |
| US20070224295A1 (en) | Compositions using evaporable silicone carriers for cosmetics, cleaning and care product compositions | |
| US6294634B1 (en) | Organosilicon compositions from cyclosiloxanes | |
| EP3233049B1 (en) | Personal care composition comprising silicone network | |
| EP0707845A2 (en) | Alkylmethylsiloxane-containing gels | |
| EP0549222B1 (en) | Siloxy-functional cyclopolysiloxanes | |
| US20220332899A1 (en) | Processes for making polysiloxazanes and using same for producing amino-functional polyorganosiloxanes | |
| CA2060012A1 (en) | Antiperspirant composition | |
| US20040062738A1 (en) | Products with selected quaternary amino functional silicone elastomers | |
| Berthiaume | Silicones in cosmetics | |
| WO2005000856A2 (en) | Siloxane compounds | |
| US20230331919A1 (en) | Method for producing hydrophilic organopolysiloxane gels | |
| JP2967139B2 (ja) | 皮膚化粧料 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1073314 Country of ref document: HK |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1073314 Country of ref document: HK |
|
| CX01 | Expiry of patent term |
Granted publication date: 20080827 |
|
| CX01 | Expiry of patent term |