CA2645956C - Silicone (meth)acrylate particles, process for preparation thereof and use thereof - Google Patents
Silicone (meth)acrylate particles, process for preparation thereof and use thereof Download PDFInfo
- Publication number
- CA2645956C CA2645956C CA2645956A CA2645956A CA2645956C CA 2645956 C CA2645956 C CA 2645956C CA 2645956 A CA2645956 A CA 2645956A CA 2645956 A CA2645956 A CA 2645956A CA 2645956 C CA2645956 C CA 2645956C
- Authority
- CA
- Canada
- Prior art keywords
- particles
- silicone
- meth
- acrylate
- process according
- 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 - Fee Related
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- 239000002245 particle Substances 0.000 title claims abstract description 160
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 133
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims description 63
- 230000008569 process Effects 0.000 title claims description 54
- 238000002360 preparation method Methods 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 239000000839 emulsion Substances 0.000 claims abstract description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000006185 dispersion Substances 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 27
- 239000012074 organic phase Substances 0.000 claims abstract description 18
- 239000002537 cosmetic Substances 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000000654 additive Substances 0.000 claims abstract description 12
- 239000008346 aqueous phase Substances 0.000 claims abstract description 12
- 239000000049 pigment Substances 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 11
- 239000008384 inner phase Substances 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000004140 cleaning Methods 0.000 claims abstract description 5
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 239000003599 detergent Substances 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 239000012812 sealant material Substances 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims abstract description 4
- 238000009736 wetting Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- -1 polyalkoxy Chemical group 0.000 claims description 100
- 239000003995 emulsifying agent Substances 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 230000003993 interaction Effects 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000011258 core-shell material Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000004756 silanes Chemical class 0.000 claims description 9
- 229910052681 coesite Inorganic materials 0.000 claims description 8
- 229910052906 cristobalite Inorganic materials 0.000 claims description 8
- 229910052682 stishovite Inorganic materials 0.000 claims description 8
- 229910052905 tridymite Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229910044991 metal oxide Inorganic materials 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 229920006317 cationic polymer Polymers 0.000 claims description 5
- 239000010954 inorganic particle Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 229920002050 silicone resin Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229940127554 medical product Drugs 0.000 claims description 3
- 150000004767 nitrides Chemical class 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910018540 Si C Inorganic materials 0.000 claims description 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000013530 defoamer Substances 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 229910052914 metal silicate Inorganic materials 0.000 claims 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical group 0.000 claims 1
- 230000003655 tactile properties Effects 0.000 abstract description 3
- 239000008385 outer phase Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 238000003756 stirring Methods 0.000 description 21
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 230000004048 modification Effects 0.000 description 16
- 238000012986 modification Methods 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000007957 coemulsifier Substances 0.000 description 15
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 12
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 12
- 150000002148 esters Chemical group 0.000 description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 12
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 12
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 11
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000011246 composite particle Substances 0.000 description 8
- 239000003755 preservative agent Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229920002545 silicone oil Polymers 0.000 description 7
- 238000010557 suspension polymerization reaction Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 5
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
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- C08L51/085—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds on to polysiloxanes
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D151/085—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds on to polysiloxanes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
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| Application Number | Priority Date | Filing Date | Title |
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| DE200710058713 DE102007058713A1 (de) | 2007-12-06 | 2007-12-06 | Silicon(meth-)acrylat-Partikel, Verfahren zu deren Herstellung sowie deren Verwendung |
| DE102007058713.0 | 2007-12-06 |
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| DE102009022628A1 (de) | 2008-12-05 | 2010-06-10 | Evonik Goldschmidt Gmbh | Verfahren zur Modifizierung von Oberflächen |
| DE102009002417A1 (de) | 2009-04-16 | 2010-10-21 | Evonik Goldschmidt Gmbh | Verwendung organomodifizierter, im Siliconteil verzweigter Siloxane zur Herstellung kosmetischer oder pharmazeutischer Zusammensetzungen |
| DE102009022630A1 (de) | 2009-05-25 | 2010-12-02 | Evonik Goldschmidt Gmbh | Emulsionen auf Basis Silylgruppen tragender Hydroxylverbindungen |
| DE102009047351A1 (de) * | 2009-12-01 | 2011-06-09 | Evonik Goldschmidt Gmbh | Komposit-Siliconmembranen mit hoher Trennwirkung |
| EP2528951B1 (en) * | 2010-01-28 | 2018-03-21 | LiquidPower Specialty Products Inc. | Miniemulsion polymerization to prepare drag reducers |
| DE102010001528A1 (de) | 2010-02-03 | 2011-08-04 | Evonik Goldschmidt GmbH, 45127 | Neue Partikel und Kompositpartikel, deren Verwendungen und ein neues Verfahren zu deren Herstellung aus Alkoxysilylgruppen tragenden Alkoxylierungsprodukten |
| DE102010002180A1 (de) * | 2010-02-22 | 2011-08-25 | Evonik Goldschmidt GmbH, 45127 | Stickstoffhaltige silizium-organische Pfropfmischpolymere |
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| DE102011003090A1 (de) | 2011-01-25 | 2012-07-26 | Evonik Goldschmidt Gmbh | Verwendung von Siliconmethacrylat-Partikeln in kosmetischen Formulierungen |
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| DE4414465C1 (de) * | 1994-04-26 | 1995-05-11 | Goldschmidt Ag Th | Polymethacrylsäureester-Polysiloxan-Blockmischpolymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung als Modifizierungsmittel und als Lackadditive |
| DE19519446A1 (de) | 1995-05-26 | 1996-11-28 | Wacker Chemie Gmbh | Monodisperse lösliche Organopolysiloxanpartikel |
| DE19535824A1 (de) | 1995-09-26 | 1997-03-27 | Wacker Chemie Gmbh | Vorvernetzte Siliconelastomer-Partikel mit Organopolymerhülle als Formulierungsbestandteil in Pulverlacken |
| JPH0995534A (ja) | 1995-09-28 | 1997-04-08 | Toshiba Silicone Co Ltd | ポリオルガノシロキサン粒子の連続製造方法 |
| US5756568A (en) | 1995-11-30 | 1998-05-26 | Dow Corning Toray Silicone Co., Ltd. | Composite cured silicone powder and method for the preparation thereof |
| DE19617379A1 (de) | 1996-04-30 | 1997-11-06 | Wacker Chemie Gmbh | Vorvernetzte Siliconelastomer-Partikel mit Organopolymerhülle als Formulierungsbestandteil in wäßrigen Lackzubereitungen |
| JPH1036675A (ja) | 1996-07-30 | 1998-02-10 | Toshiba Silicone Co Ltd | シリコーンエマルジョン組成物およびそれを用いたシリコーン粉体の製造方法 |
| EP0835897B1 (de) * | 1996-10-11 | 2001-11-28 | Goldschmidt AG | Siliconpoly(meth)acrylate, deren Herstellung und deren Verwendung in Beschichtungen |
| DE19649844C1 (de) * | 1996-12-02 | 1997-12-18 | Goldschmidt Ag Th | Mit Acrylatgruppen modifizierte Organosiloxanylderivate von Alkandiolmonovinylethern, Verfahren zu deren Herstellung und deren Verwendung als strahlenhärtbare Bindemittel |
| US6207782B1 (en) * | 1998-05-28 | 2001-03-27 | Cromption Corporation | Hydrophilic siloxane latex emulsions |
| DE19850507C1 (de) * | 1998-11-03 | 2000-05-04 | Goldschmidt Ag Th | Verfahren zur Herstellung von Acrylsäureestern und/oder Methacrylsäureestern von hydroxyfunktionellen Siloxanen und/oder polyoxyalkylenmodifizierten Siloxanen und deren Verwendung |
| JP5057413B2 (ja) | 1999-08-03 | 2012-10-24 | 東レ・ダウコーニング株式会社 | 有機架橋粒子、そのサスペンジョン、およびそれらの製造方法 |
| JP4469052B2 (ja) | 2000-02-29 | 2010-05-26 | 東レ・ダウコーニング株式会社 | 架橋シリコーン粒子の製造方法 |
| DE10011564C1 (de) | 2000-03-09 | 2001-09-27 | Goldschmidt Ag Th | Verfahren zur Herstellung von Polyorganosiloxanemulsionen |
| FR2808704B1 (fr) * | 2000-05-10 | 2002-08-16 | Rhodia Chimie Sa | Agents tensioactifs formes par des particules minerales de dimension nanometrique de surface modifiee |
| JP3717379B2 (ja) | 2000-08-02 | 2005-11-16 | 信越化学工業株式会社 | 球状シリコーン樹脂微粒子の製造方法 |
| JP2003002973A (ja) | 2001-04-18 | 2003-01-08 | Ge Toshiba Silicones Co Ltd | 球状シリコーン微粒子の製造方法 |
| JP5127100B2 (ja) | 2001-04-26 | 2013-01-23 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物の水性エマルジョンの製造方法、その製造装置および硬化シリコーン粒状物の懸濁液の製造方法 |
| JP3925629B2 (ja) | 2002-04-10 | 2007-06-06 | 信越化学工業株式会社 | シリコーンエラストマー球状粉末の製造方法 |
| JP4289881B2 (ja) | 2002-12-27 | 2009-07-01 | 東レ・ダウコーニング株式会社 | 複合シリコーンゴム粒子およびその製造方法 |
| DE10359764A1 (de) * | 2003-12-19 | 2005-07-14 | Goldschmidt Ag | Polysiloxane mit über SiOC-Gruppen gebundenen (Meth)acrylsäureestergruppen, Verfahren zu deren Herstellung sowie deren Verwendung als strahlenhärtbare abhäsive Beschichtung |
| DE102004014704A1 (de) | 2004-03-25 | 2005-10-13 | Wacker-Chemie Gmbh | Partikelstabilisierte Emulsionen |
| DE102004022406A1 (de) * | 2004-05-06 | 2005-12-15 | Wacker-Chemie Gmbh | Polysiloxan-Pfropfpolymerisat |
| DE102004024009A1 (de) * | 2004-05-14 | 2005-12-01 | Goldschmidt Gmbh | Verwendung von neuen Polysiloxanen mit über SiOC-Gruppen gebundenen (Meth)acrylsäureestergruppen als Additive für strahlenhärtende Beschichtungen |
| DE602005008246D1 (de) | 2004-07-07 | 2008-08-28 | Dow Corning | Emulsionen von organopolysiloxanharzen, hergestellt durch emulsionspolymerisation |
| DE102004034740A1 (de) * | 2004-07-17 | 2006-02-02 | Goldschmidt Gmbh | Polysiloxane mit über SiOC-Gruppen gebundenen (Meth)arcylsäureestergruppen und fluorierten Resten sowie deren Verwendung als strahlenhärtbare abhäsive Beschichtung |
| JP2006070378A (ja) * | 2004-09-01 | 2006-03-16 | Toray Ind Inc | ニット生地 |
| DE102004047708A1 (de) | 2004-09-30 | 2006-04-06 | Wacker Chemie Ag | Kern-Schalepartikel enthaltende Zusammensetzung und ihre Herstellung |
| DE102004053314A1 (de) | 2004-11-04 | 2006-05-11 | Wacker Chemie Ag | Verfahren zur Herstellung von mit Silikon modifizierten Polymerisaten |
| DE102005001040B4 (de) * | 2005-01-07 | 2017-06-22 | Evonik Degussa Gmbh | Mehrfachfunktionelle Polysiloxane mit über SiOC-Gruppen gebundenen (Meth)acrylsäureestergruppen und einem unmodifizierten Polysiloxan-Block, Verfahren zu deren Herstellung sowie deren Verwendung als strahlenhärtbare abhäsive Beschichtung |
| DE102005011785A1 (de) | 2005-03-11 | 2006-09-21 | Goldschmidt Gmbh | Langzeitstabile kosmetische Emulsionen |
| DE102006009841A1 (de) * | 2006-03-01 | 2007-09-06 | Röhm Gmbh | Additive Baustoffmischungen mit quellbaren Polymergebilden |
| DE102006041971A1 (de) * | 2006-09-07 | 2008-03-27 | Evonik Goldschmidt Gmbh | Verwendung von partikulären Emulgatoren in abhäsiven siloxanhaltigen Beschichtungsmassen |
-
2007
- 2007-12-06 DE DE200710058713 patent/DE102007058713A1/de not_active Withdrawn
-
2008
- 2008-10-06 EP EP08165900.5A patent/EP2067811B1/de not_active Not-in-force
- 2008-12-03 JP JP2008308124A patent/JP5590539B2/ja not_active Expired - Fee Related
- 2008-12-03 US US12/327,175 patent/US8653214B2/en not_active Expired - Fee Related
- 2008-12-05 CN CNA2008101909853A patent/CN101497682A/zh active Pending
- 2008-12-05 CA CA2645956A patent/CA2645956C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5590539B2 (ja) | 2014-09-17 |
| CN101497682A (zh) | 2009-08-05 |
| US8653214B2 (en) | 2014-02-18 |
| EP2067811A1 (de) | 2009-06-10 |
| JP2009149880A (ja) | 2009-07-09 |
| DE102007058713A1 (de) | 2009-06-10 |
| US20090149573A1 (en) | 2009-06-11 |
| CA2645956A1 (en) | 2009-06-06 |
| EP2067811B1 (de) | 2018-09-26 |
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