EP2406303A1 - Nouveaux polyorganosiloxanes et leurs utilisations - Google Patents

Nouveaux polyorganosiloxanes et leurs utilisations

Info

Publication number
EP2406303A1
EP2406303A1 EP10709718A EP10709718A EP2406303A1 EP 2406303 A1 EP2406303 A1 EP 2406303A1 EP 10709718 A EP10709718 A EP 10709718A EP 10709718 A EP10709718 A EP 10709718A EP 2406303 A1 EP2406303 A1 EP 2406303A1
Authority
EP
European Patent Office
Prior art keywords
formula
polyorganosiloxanes
group
use according
radicals
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP10709718A
Other languages
German (de)
English (en)
Inventor
Dieter Wrobel
Hubertus Eversheim
Julien Richeton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Momentive Performance Materials GmbH
Momentive Performance Materials Inc
Original Assignee
Momentive Performance Materials GmbH
Momentive Performance Materials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Momentive Performance Materials GmbH, Momentive Performance Materials Inc filed Critical Momentive Performance Materials GmbH
Publication of EP2406303A1 publication Critical patent/EP2406303A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—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
    • A61K8/89—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/04—Polyamides derived from alpha-amino carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion

Definitions

  • the invention relates to novel Polyorganosiioxane, processes for their preparation and their use, in particular as power and / or alongsideübertragungsflüssi- opportunities, such as hydraulic fluids.
  • Synthetic hydraulic fluids are known in addition to various aliphatic, aromatic or unsaturated hydrocarbons, such as alpha-olefins, phosphoric esters, phenyl ethers, polyesters or polyethers, and also polyorganosiloxanes for a long time (eg US 2398187, US 4048084, US 4116847, US 4132664, US 4175049, US 4357473, GB 1093555, GB 867167, US 4340495, etc.). Further, US 5684112 discloses branched polyorganosilioxanes as conditioning agents for use in cosmetic compositions.
  • a compound of the formula (Me 3 Si0) 3 Si-phenyl is sold under the trade name Baysilon PD5 by Momentive Performance Materials inter alia as a damping fluid.
  • said compound as well as many other low molecular weight polyorganosioxanes, when contacted with silicone gaskets or membranes, result in increased swelling of the silicone gaskets or membranes or diffusion of the liquid through the silicone gasket, resulting in leakage of the liquid.
  • the object of the present invention was therefore to find a suitable as a power transmission fluid medium, which does not have the disadvantages mentioned.
  • the medium should be used in particular for power transmission as well as a medium for damping so time-delayed force distribution or power transmission.
  • a hydraulic bearing which consists of elastic see rubber membranes as a spring system, or enclosed by membranes air cushion, which separate another room with a viscous, damping power transmission fluid.
  • This liquid should continue to have a suitable viscosity range at different temperatures, in particular at low temperature, and be resistant to high temperatures and change the enclosing membrane only slightly.
  • the liquid medium should have a low compressibility and in interaction with metals and sealing materials such as in particular elastomers, such as silicone elastomers they should not change their properties as possible.
  • glycols also used as damping fluid for the production of so-called hydraulic bearings, although they are used in hydraulic bearings with elastomeric spring elements based on natural rubber or EPDM, but prove to be largely unusable in spring elements made of silicone elastomers, since they are an acceptable swelling, but lead to an undesirably high diffusion or permeability through these membranes, and further do not have a sufficiently low viscosity in the low temperature range.
  • Other compounds, such as low molecular weight synthetic media have too low a boiling point or they will harden in the presence of atmospheric oxygen or moisture in such a way that the viscosity at least increases or even the liquid solidifies.
  • the invention thus had the task to find a suitable liquid
  • the inventors surprisingly found in the class of silylated siliconates and
  • Silicates Compounds with a low degree of polymerization that could solve these problems.
  • the present invention thus provides:
  • R is selected from the group consisting of:
  • Aliphatic and / or aromatic radicals having up to 30 carbon atoms which may have one or more oxygen atoms, one or more halogen atoms and one or more cyano groups, with the proviso that at least one of the radicals R is bound in M via a carbon atom to silicon, and at least one of the radicals R in M has at least two, more preferably at least 4, even more preferably at least 5 carbon atoms, these being used as a force and / or heat transfer fluid or constituent in cosmetic compositions.
  • a power transmission fluid is suitable for transmitting and / or distributing mechanical forces over a certain distance between the place of generation and action.
  • the power transmission fluids include, in particular, hydraulic, damping and transmission fluids or oils. Requirements that meet the power transmission fluids of the present invention generally include:
  • polyorganosiloxanes of formula (I) preferably has a pour point (DIN ISO 3016, ASTM D5985) of less than -28 0 C and a pour point (DIN ISO 3016, ASTM E 537-76 D of less than -30 0 C.
  • the polyorganosiloxanes of the formula (I) preferably have a boiling point greater than 180 ° C., more preferably greater than 190 ° C.
  • the polyorganosiloxanes of formula (I) preferably at polydimethylsiloxane elastomers have a permeation determined as so-called fuel permeability KD according to DIN 53532 of less than 70 [g / m 2 / d] at 140 0 C, preferably less than 40 [g / m 2 / d], more preferably a KD value of less than 20 [g / m 2 / d] for a sample having the thickness of 2 mm.
  • the groups R include both R groups which are over
  • Carbon atoms are bonded to silicon atoms, as well as groups R, which are bonded via oxygen atoms to silicon atoms, i. it is in this
  • the proviso according to which at least one of the radicals R in M is bonded to silicon via a carbon atom and at least one of the radicals R in M has at least two carbon atoms also includes the case that a radical R is present in M, the Si-C having at least two carbon atoms, more preferably at least four carbon atoms, more preferably at least five carbon atoms.
  • a radical R is present in M
  • M has a Si-C bonded radical R having at least two carbon atoms, more preferably at least four carbon atoms, more preferably at least five carbon atoms.
  • At least one of the radicals R in M represents a group which has an aromatic group, in particular a phenyl group, preferably a phenylethyl or phenylpropyl group, in particular a (2-phenyl-2-methyl) ethane-1-yl group.
  • At least one of the radicals R in M represents a group of the formula R * which is selected from the group consisting of: - aryl,
  • R 1 is hydrogen or C 1 to C 3 alkyl
  • R 2 has the same meaning as R
  • R 2 has the same meaning as R, and
  • R 3 has the same meaning as R or is hydrogen.
  • Preferred groups M include:
  • R "or R ' has at least two carbon atoms, more preferably at least four carbon atoms, more preferably at least five carbon atoms, more preferably M is
  • the polyorganosiloxanes according to the invention may have the same or different groups M. That is, in addition to the obligatory groups M, as defined above, there may also be groups M which have neither radicals R with at least two carbon atoms nor SiC-bonded radicals, such as -SiMe 3 and -Si (OMe) 3 .
  • all groups M in the polyorganosiloxanes according to the invention are preferably radicals R having at least two carbon atoms, in particular SiC-bonded radicals R having at least two carbon atoms.
  • the present invention relates to the use of polyorganosiloxanes of the formula (I) in which the polyorganosiloxanes have the formula (Ia) or (Ib):
  • the polyorganosiloxanes of the formulas (Ia) or (Ib) preferably have the following structures: M 4 QM 3 T
  • the present invention relates to the use of polyorganosiloxanes of the formula (I) in which all radicals M have at least one, preferably exactly one group of the formula R * .
  • the present invention relates to the use of polyorganosiloxanes of the formula (I) in which all R radicals in M are bonded to silicon via carbon atoms.
  • the polyorganosiloxanes according to the invention have identical groups M, the SiC-bonded radicals R with at least two
  • Examples include:
  • QM 4 such as:
  • n 0 to 8, preferably 1 to 5.
  • the present invention relates to the use of polyorganosiloxanes of the following formulas:
  • the polyorganosiloxanes used according to the invention preferably have a molecular weight (determined by gel permeation chromatography against polystyrene as standard) with a number average M n of 360 to 2000 g / mol.
  • the use according to the invention also includes in particular the use as a power transmission fluid in hydraulic bearings.
  • Hydraulic bearings are damping elements which comprise a spring body and a damping unit.
  • the damping unit comprises the cavities and flow channels filled with the power transmission fluid (see, for example, EP 0 547 287).
  • the present invention also relates to hydraulic bearings containing polyorganosiloxanes of the formula
  • the polyorganosiloxanes of the formula (I) can also surprisingly be used as a constituent of cosmetic compositions, since in this way siloxane compounds having a solubility behavior suitable for cosmetic ingredients can be provided.
  • they have a desired low spreading or migration behavior, low tack compared to, for example, sand and dust and a high refractive index n 2 5 D above 1, 50, in particular higher than 1, 51.
  • the low migration behavior is particularly desirable in color cosmetic formulations to prevent penetration of these components into the eye or mouth.
  • inventive compounds can therefore be advantageous cosmetic compositions such as mascaras and 'LJP Gloss', other coloring skin care products and hair care products such as shampoos, hair conditioners and, in particular hair treatments, oils and -fluids produce to increase the gloss of skin nail and hair surfaces.
  • inventive substances Due to the high refractive index of more than 1, 5, the inventive substances are also excellently suitable for containing a decrease in the whitening of pigmented or solids or waxes cosmetic products (antiperspirants) on the skin contribute (anti-Weissel effect, 'Anti-whitening ' ).
  • the present invention also relates to cosmetic compositions containing polyorganosiloxanes of the formula (I).
  • R is selected from the group consisting of:
  • Aliphatic and / or aromatic radicals having up to 30 carbon atoms which may have one or more oxygen atoms, one or more halogen atoms and one or more cyano groups, with the proviso that at least one of the radicals R in M on a
  • Carbon atom is bonded to silicon and at least one of the radicals
  • the present invention also relates to a process for the preparation of the polyorganosiloxanes of the formula (T), comprising:
  • CH 2 CHR 1 -R 2 , wherein R 1 and R 2 are as defined above, or a compound
  • the mixture heats up to 120 0 C.
  • the remaining amount of 2022 g of reaction mixture from Example 1 (18.5 mol M H groups) are added within about one hour.
  • the temperature of the reaction mixture is maintained by controlling the metering or by controlling the heating medium temperature between 140 and 150 0 C. After completion of the metering is stirred at 140 0 C for 3 hours.
  • the subsequent measurement of the SiH content gives 0.03 mmol / g. This corresponds to a conversion based on SiH of 99.2%.
  • the excess methylstyrene is removed by heating at 150 0 C bottom temperature and a vacuum of ⁇ 5 mbar.
  • Viscosity at 25 0 C in Höppler falling ball viscometer 40 mPa.s at 25 0 C, 41 17 mPa.s at -40 ° C,
  • Refractive index n 25 D 1, 5020, density: 25 0 C per aerometers 1, 015 g / ml, vaporizable proportions determined by weight with the halogen dryer Mettler HR 73, 1 g of sample weight after 30 min 120 0 C of 1, 6.%.
  • Example 3 Preparation of the precursor T Ph M H 3 2010 g of tetramethyldisiloxane (30 mol), 1200 g of water, 60 g of 37% hydrochloric acid and 1000 g of toluene are placed in a 6 L flat-section vessel with heating / cooling jacket equipped with stirrer, thermometer, reflux condenser, metering device and nitrogen blanketing. With vigorous stirring 1586 g of phenyltrimethoxysilane (8 mol) are added. As a result of the reaction, the reaction mixture heats up to 47 ° C. during the metering. After the end of the metering, stirring is continued for one hour; after switching off the stirrer, two phases rapidly form.
  • reaction mixture from Example 3 15 mol (M H ) is added in the course of about one hour.
  • the temperature of the reaction mixture is maintained between 140 and 150 ° C. by controlling the metering rate or by regulating the temperature of the heating medium.
  • Viscosity at -40 0 C in Höppler falling ball viscometer: 11,300 mPa ⁇ s, refractive index n 25 D 1, 5210, vaporisable portion, Halogen dryer Mettler HR 73 1, 6 wt% at 1 g test sample, 30 min 120 0 C, density. : 25 0 C per aerometer spindle 1, 000 g / ml formula:
  • Silicone elastomers 3 test specimens triple determination) with a diameter of 36.6 mm and brings by punching further smaller holes markings to distinguish sample 1-3. From each test specimen, the weight is determined on an analytical balance and its density by buoyancy measurement in water with a balance for density determination. The specimens are covered with a liquid level of 10 - 20 mm. The liquid volume is about 80 times the total specimen volume.
  • the specimens After contact time with the liquid test media and defined temperature, the specimens are removed and allowed to cool for about 10 minutes to room temperature (25 0 C) on a pulp base. Again, weight and density are determined within one hour of removal. The weight swelling was calculated according to the following formula.
  • Weight swelling is calculated in% to: (wt. NaHg- weight. VO r) * 100 / wt. VO r
  • the experiment shows that the polyorganosiloxanes according to the invention have a slightly increased weight swelling compared to glycol. However, the swelling is below that of mineral oil or a compound such as T phe M 3 .
  • the permeability was determined as KD value according to formula in DIN 53532 with aluminum test equipment from Rycobel, hereinafter referred to as 'Vapometer ' .
  • the test area of each individual sample of the crosslinked silicone elastomer had a value of 31, 7 cm 2 , a thickness of about 2 mm, the test duration was 42 days.
  • the vapometer contained no liquid after 14 days, ie the diffusion was too high to determine a mass flow.
  • the vapometer contained no liquid after 2 days, ie the diffusion was too high to determine a mass flow.
  • compositions The use of the compounds according to the invention and their suitability in cosmetic formulations is illustrated by the following compositions:
  • Examples 6 to 12 show that compounds such as those of Examples 2 and 4 cosmetic ingredients such as the mentioned under the INCI name Phenylpropyldimethylsiloxysilicate Silshine® 151 with regard to miscibility with cosmetic ingredients, without accepting obvious disadvantages with cosmetic properties.
  • the high refractive index of the compound of Example 4 leads to particularly advantageous gloss effects.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thermal Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Physics & Mathematics (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Silicon Polymers (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne de nouveaux polyorganosiloxanes, leur procédé de production et leur utilisation, notamment sous forme de fluides de transmission d'énergie ou de fluides de transmission thermique, comme des fluides hydrauliques, et dans des compositions cosmétiques.
EP10709718A 2009-03-13 2010-03-12 Nouveaux polyorganosiloxanes et leurs utilisations Withdrawn EP2406303A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009012665A DE102009012665A1 (de) 2009-03-13 2009-03-13 Neue Polyorganosiloxane und deren Verwendungen
PCT/EP2010/053180 WO2010103103A1 (fr) 2009-03-13 2010-03-12 Nouveaux polyorganosiloxanes et leurs utilisations

Publications (1)

Publication Number Publication Date
EP2406303A1 true EP2406303A1 (fr) 2012-01-18

Family

ID=42237388

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10709718A Withdrawn EP2406303A1 (fr) 2009-03-13 2010-03-12 Nouveaux polyorganosiloxanes et leurs utilisations

Country Status (6)

Country Link
EP (1) EP2406303A1 (fr)
JP (1) JP2012520367A (fr)
KR (1) KR20110131267A (fr)
CN (1) CN102395620B (fr)
DE (1) DE102009012665A1 (fr)
WO (1) WO2010103103A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2981571B1 (fr) * 2011-10-21 2013-11-08 Oreal Composition cosmetique comprenant des particules d'aerogel de silice et des huiles siliconees
JP6105896B2 (ja) 2012-04-23 2017-03-29 東レ・ダウコーニング株式会社 液状アリール基含有ポリオルガノシロキサン
US9051434B2 (en) * 2013-01-31 2015-06-09 Wacker Chemical Corporation Amphiphilic organopolysiloxane dendrimers with high refractive index
DE102015202158A1 (de) * 2015-02-06 2016-08-11 Technische Universität München Verzweigte Organosiloxane als Wärmeträgerflüssigkeit
JP6473392B2 (ja) * 2015-07-10 2019-02-20 信越化学工業株式会社 化粧料
WO2018207549A1 (fr) * 2017-05-10 2018-11-15 国立研究開発法人産業技術総合研究所 Huile lubrifiante synthétique
WO2019242858A1 (fr) * 2018-06-20 2019-12-26 Wacker Chemie Ag Mélange de méthylpolysiloxanes mq utilisé comme fluide caloporteur
EP4021981B1 (fr) * 2019-11-18 2023-02-22 Wacker Chemie AG Mélanges de méthylpolysiloxane en tant que fluide caloporteur
WO2021141836A1 (fr) * 2020-01-09 2021-07-15 Dow Silicones Corporation Polysiloxanes ramifiés et leurs procédés de préparation et d'utilisation en tant que fluides de transfert de chaleur
US12398273B2 (en) 2021-03-05 2025-08-26 Wacker Chemie Ag Siloxane-functionalized silica
CN121666436A (zh) * 2023-07-26 2026-03-13 3M创新有限公司 硅氧烷传热流体、设备和方法
WO2025230001A1 (fr) * 2024-05-02 2025-11-06 ジェレスト， インコーポレイテッド Fluide de transfert de chaleur, procédé d'échange de chaleur entre un objet et un fluide de transfert de chaleur, utilisation de composition et composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5817302A (en) * 1995-02-10 1998-10-06 General Electric Company Low viscosity organofunctionalized siloxysilicates and cosmetic formulations therewith

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2398187A (en) 1943-06-11 1946-04-09 Corning Glass Works Hydraulic fluid
GB867167A (en) 1958-11-10 1961-05-03 Midland Silicones Ltd Alkoxysilanes and siloxanes
US3308145A (en) * 1963-08-28 1967-03-07 Dow Corning Siloxanes
US3413329A (en) 1964-12-31 1968-11-26 Union Carbide Corp Chloromethylated aralkyl silanes and siloxanes
BE786656A (fr) * 1971-07-30 1973-01-24 Ici Ltd Siloxanes
US4048084A (en) 1975-09-24 1977-09-13 Olin Corporation Functional fluid systems containing alkoxysilane cluster compounds
US4175049A (en) 1977-04-27 1979-11-20 Olin Corporation Functional fluid methods using alkoxysilane ester cluster compounds
US4058546A (en) 1977-04-28 1977-11-15 Olin Corporation Alkoxysilane double cluster compounds with silicone bridges and their preparation and use
US4132664A (en) 1977-05-20 1979-01-02 Olin Corporation Functional fluid method using alkoxysilane multiple cluster compounds
US4357473A (en) 1979-11-01 1982-11-02 Olin Corporation Method for preparing alkoxysilane cluster compounds; resulting novel compounds; and their use as functional fluids
AU6904781A (en) 1980-04-04 1981-10-08 General Electric Company Silicone brake fluid
DE4141332C2 (de) 1991-12-14 1995-05-24 Freudenberg Carl Fa Umschaltbares Lager
JPH0995492A (ja) * 1995-10-02 1997-04-08 Asahi Glass Co Ltd 含フッ素有機ケイ素化合物およびその製造方法
US5670686A (en) * 1996-08-13 1997-09-23 Dow Corning Corporation Alkyl substituted siloxanes and alkyl substituted polyether fluids
US6140445A (en) * 1998-04-17 2000-10-31 Crompton Corporation Silane functional oligomer
JP3915881B2 (ja) * 2001-03-14 2007-05-16 信越化学工業株式会社 分岐状低分子シロキサンの製造方法
US6623399B2 (en) * 2001-12-28 2003-09-23 Dow Corning Corporation Traction fluids
KR20080063499A (ko) * 2005-10-18 2008-07-04 디시이 아프릴리스, 인코포레이티드 홀로그래피 저장을 위한 양이온성 중합을 지지하는 실록산화합물을 포함하는 광중합 매체

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5817302A (en) * 1995-02-10 1998-10-06 General Electric Company Low viscosity organofunctionalized siloxysilicates and cosmetic formulations therewith

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2010103103A1 *

Also Published As

Publication number Publication date
CN102395620B (zh) 2014-09-17
KR20110131267A (ko) 2011-12-06
JP2012520367A (ja) 2012-09-06
DE102009012665A1 (de) 2010-09-16
WO2010103103A1 (fr) 2010-09-16
CN102395620A (zh) 2012-03-28

Similar Documents

Publication Publication Date Title
EP2406303A1 (fr) Nouveaux polyorganosiloxanes et leurs utilisations
EP3744761B1 (fr) Polyethérsiloxanes à base de sioc
DE60221383T2 (de) Silikonzusammensetzung für einen wasserabweisenden überzug
DE2809588C2 (de) Verwendung eines Gemischs aus einem Polysiloxan und einem Silan als Haftvermittler in einer Siliconelastomermasse
EP1323768B1 (fr) Copolymères polysiloxane contenant des groupes alkényles et leur utilisation comme agents anti-aérosol dans des compositions de revêtement de silicone
EP1595909B1 (fr) Utilisation de nouveaux polysiloxanes présentant des groupments (meth)acrylates, reliés par des groupments SiOC, comme additifs pour des rêvetments durcisables par rayonnement
DE102012210553A1 (de) Siliconpolyether und Verfahren zu deren Herstellung aus Methylidengruppen tragenden Polyethern
DE2645614A1 (de) Haertbare organopolysiloxanmasse
DE102013216777A1 (de) Bei Raumtemperatur härtbare Silikonharz-Zusammensetzungen
EP0177825A1 (fr) Préparation d'huile lubrifiante
DE19750706A1 (de) Duftgebende, nicht flüchtige, polymere Siloxane
DE10022247A1 (de) Polyurethan und dessen Verwendung zur Modifizierung rheologischer Eigenschaften
DE2507362A1 (de) Acetoxysiloxanzubereitung
DE69727394T2 (de) Vernetzbare zusammensetzungen, die funktionalisierte siliconöle enthalten und verwendung dieser zusammensetzungen zum herstellen von polyurethanfilmen
DE4117471A1 (de) Silikonkautschuk-zusammensetzungen und deren gehaertete produkte
US20120046485A1 (en) Novel Polyorganosiloxanes And Use Thereof
DE10210026A1 (de) Verzweigte Organosiliciumverbindungen als Antimisting Additive für Siliconbeschichtungszusammensetzungen
EP3484943A1 (fr) Procédé pour produire en continu des siloxanes ramifiés pauvres en alcoxys
DE2759653C2 (de) Hitzehärtbare Organopolysiliciummasse
EP0238685B1 (fr) Procédé pour la fabrication de pièces moulées de polyuréthane
DE19506396A1 (de) Optisch klare Aminosiliconzusammensetzungen
DE3039721A1 (de) Verfahren zur herstellung von ueberzuegen
DE1593567A1 (de) Verfahren zur Herstellung von Organozinnverbindungen
DE4309831A1 (de) Abhäsive Beschichtungsmasse mit einem den Grad der Abhäsivität beeinflussenden Zusatzmittel
EP0606634A1 (fr) Organopolysiloxane, modifié avec esters d'acide insaturés et groupes quaternaires d'ammonium, leur préparation et usage

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20111012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: RICHETON, JULIEN

Inventor name: WROBEL, DIETER

Inventor name: EVERSHEIM, HUBERTUS

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20121026

TPAC Observations filed by third parties

Free format text: ORIGINAL CODE: EPIDOSNTIPA

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20150527