WO2006125708A1 - Composition contenant des silasesquioxanes oligomeres polyedriques fonctionnalises et son procede de production - Google Patents

Composition contenant des silasesquioxanes oligomeres polyedriques fonctionnalises et son procede de production Download PDF

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Publication number
WO2006125708A1
WO2006125708A1 PCT/EP2006/061838 EP2006061838W WO2006125708A1 WO 2006125708 A1 WO2006125708 A1 WO 2006125708A1 EP 2006061838 W EP2006061838 W EP 2006061838W WO 2006125708 A1 WO2006125708 A1 WO 2006125708A1
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type
acid
silanes
polyhedral oligomeric
reaction
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PCT/EP2006/061838
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German (de)
English (en)
Inventor
Adolf KÜHNLE
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Degussa
Kuehnle Adolf
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Priority claimed from DE200510024814 external-priority patent/DE102005024814A1/de
Application filed by Degussa, Kuehnle Adolf filed Critical Degussa
Publication of WO2006125708A1 publication Critical patent/WO2006125708A1/fr

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    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • 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

Definitions

  • the invention relates to a composition comprising functionalized polyhedral oligomeric silsesquioxanes, a process for their preparation and their use.
  • Functionalized polyhedral oligomeric silsesquioxanes can be used to synthesize and modify polymers in a wide range of applications.
  • the resulting polymers can be used, for example, in coatings, adhesives, plastic moldings, fibers or in packaging materials. In this way, the properties of these polymers can be influenced over a wide range.
  • Numerous thermal and mechanical properties of polymers, such as different moduli, temperature stability, adhesion properties to a variety of materials, oxidation stability, scratch and tear resistance, can be improved by blending, grafting, grafting, copolymerization or copolycondensation with functionalized polyhedral oligomeric silsesquioxanes.
  • WO 03/064490 also describes a process for the preparation of functionalized polyhedral oligomeric silsesquioxanes by "corner capping", however, using alkoxysilanes, which in terms of
  • composition the functionalized polyhedral having oligomeric silsesquioxanes, made possible in only one process step, without that in a subsequent process step, the base has to be removed from the product mixture.
  • this is achieved by reacting the silanes used, where at least one of the silanes used is an aminosilane, at a neutral to acidic pH without the use of a basic catalyst to give the desired functionalized polyhedral oligomeric silsesquioxanes.
  • the process according to the invention is carried out using an acid, and it must be ensured in the case of the silanes used that the rate constants of the silanes and modified aminosilanes used in the reaction to the functionalized polyhedral oligomeric silsesquioxanes are of the same order of magnitude. Furthermore, the process according to the invention has the advantage that it is possible to dispense with the preparation of an incompletely condensed polyhedral oligomeric silsesquioxane as intermediate in the preparation of functionalized polyhedral oligomeric silsesquioxanes.
  • the cages of the functionalized polyhedral oligomeric silsesquioxanes may contain further substituents with functional groups, such as for example, methacrylic and / or epoxy groups.
  • functional groups such as for example, methacrylic and / or epoxy groups.
  • Methacrylic group are highly reactive and usually do not have the desired stability.
  • the present invention therefore provides a process for the preparation of a composition comprising functionalized polyhedral oligomeric silsesquioxanes, which is characterized in that
  • A amino or at least one amino group-containing substituents of the R type
  • R, R f hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked, isocyanate, acrylate, methacrylate, mercapto, nitrile, phosphine group or at least one such type X substituent of type R,
  • Y OH, ONa, OK, OR ⁇ OCOR ⁇ OSiR ⁇ 3 , Cl, Br, I or NR ⁇ 2 ,
  • R hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked isocyanate,
  • a ' amino, ammonium or at least one amino or ammonium group-containing substituents of type R,
  • both the substituents of type R and type A 'and of type X are the same or different and have at least one substituent of type A', and a composition comprising these functionalized polyhedral oligomeric silsesquioxanes.
  • the invention further relates to the use of the composition according to the invention or the silsesquioxanes according to the invention for the synthesis of catalysts and their starting compounds, for stabilizers and for the synthesis or modification of ceramic compositions and polymers.
  • A amino or at least one amino group-containing substituents of the R type
  • R, R f hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked, isocyanate, acrylate, methacrylate, mercapto, nitrile, phosphine group or at least one such type X substituent of type R,
  • Y OH, ONa, OK, OR ⁇ OCOR ⁇ OSiR ⁇ 3 , Cl, Br, I or NR ⁇ 2 ,
  • both the substituents of the type R, type R f and type A and the type X are the same or different and the rate constants of the modified aminosilanes and silanes used in the reaction to form functionalized polyhedral oligomeric silsesquioxanes in the same order are used. It is important for the process according to the invention that the silanes used as starting material and modified aminosilanes are matched in terms of their saponification rate, this means that the rate constants are related to the saponification reaction of the silane and the modified aminosilanes in a similar order.
  • the functionalized polyhedral oligomeric silsesquioxanes have a substituent distribution in accordance with the educt composition of the silanes. If, for example, the aminosilane ASiY 3 and the silane RSiY 3 are used in a molar mixing ratio of 1: 1 in the process according to the invention, the result is a composition which predominantly contains a functionalized, fully condensed polyhedral oligomeric silsesquioxane type A 4 R 4 Si 8 ⁇ i2. In different
  • the composition also silsesquioxanes of the type A 3 R 5 Si S Oi 2 , A 2 R6Sis0i2, A 5 R 3 Si8 ⁇ i2 and A 6 R 2 SiSOi 2 on , Information on the rate constants regarding the
  • R, R f hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked, isocyanate, acrylate, methacrylate, mercapto, nitrile, phosphine group or at least one such type X substituent of type R,
  • Y OH, ONa, OK, OR ⁇ OCOR ⁇ OSiR ⁇ 3 , Cl, Br, I or NR ⁇ 2 and
  • substituents of the type R, type R f , type X and type Y are the same or different, used.
  • Silanes are preferably used, the substituents of Y is selected from OH, OR comprise ⁇ ⁇ OCOR or Cl.
  • Alkoxysilanes according to the formula are particularly preferred in the process according to the invention.
  • R, R f hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked, isocyanate, acrylate, methacrylate, mercapto, nitrile, phosphine group or at least one such type X substituent of type R,
  • Trialkoxysilanes in particular alkyltrialkoxysilanes RSi (OR ') 3, are particularly preferably used, the alkoxy group (OR') having from 1 to 4 carbon atoms, in particular methoxy or ethoxy group, and the alkyl group (R) having from 1 to 5 carbon atoms, in particular from 2 to 4 carbon atoms, but preferably has 3 carbon atoms.
  • alkyltrialkoxysilanes of the formula RSi (OR ') 3 are isobutyltrimethoxysilane (DYNASYLAN ® IBTMO), isobutyltriethoxysilane, propyltrimethoxysilane (Dynasylan ® PTMO) propyltriethoxysilane,
  • trialkoxysilanes having a substituent of the type X according to the formula XSi (OR ') 3 such as, for example, 3-chloropropyltrimethoxysilane (CPTMO), 3
  • Glycidyloxypropyltrimethoxysilane (DYNASYLAN ® GLYMO), 3- mercaptopropyltrimethoxysilane (DYNASYLAN ® MTMO), 3-methacryloxypropyltrimethoxysilane (DYNASYLAN ® MEMO) are used.
  • Alkenyltrialkoxysilanes such as vinyltrimethoxysilane (DYNASYLAN ® VTMO) or vinyltriethoxysilane be used.
  • R, R ' hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • A amino or at least one amino group-containing substituents of the R type
  • aminosilanes are used which have substituents of the type Y selected from OH, OR ⁇ OCOR ⁇ or Cl. Particularly preferred in the process according to the invention are aminosilanes according to the formula
  • the substituents of the type R f may be the same or different.
  • aminosilanes in the process according to the invention as aminoalkyltrialkoxysilanes, the substituent of type A preferably having the amino group in the terminal position, the alkyl and alkoxy groups having from 1 to 10 carbon atoms, preferably from 2 to 5 carbon atoms and preferably from 3 have up to 4 carbon atoms.
  • 3-aminopropyltriethoxysilane is used in the process according to the invention.
  • the amino group may be a primary, secondary or tertiary amino group.
  • one or more aminosilanes are first reacted with an acid and then the silanes of the formula (R 3 Xb) mSiY n was added to the reaction mixture.
  • silanes of the formula (R 3 Xb) mSiY n was added to the reaction mixture.
  • R 3 Xb alkyltrialkoxysilanes according to the formula
  • halosilanes preferably trichlorosilanes
  • alkoxysilanes are used together with alkoxysilanes in the process according to the invention.
  • the process according to the invention is preferably carried out at a pH of from 3 to 11, preferably at a pH of from 4 to 9, particularly preferably from 5.5 to 8.5. In a particular embodiment of the process according to the invention, this is carried out at a pH of 7 + 0.3.
  • the aminosilane used is modified with an acid, these may be mono- or poly-protic acids.
  • acid here can be used both inorganic acids and their derivatives, selected from hydrochloric acid, sulfuric acid, sulfurous acid, nitric acid, nitrous acid or carbonic acid, as well as mono- or polyprotic organic acids.
  • saturated and unsaturated alkyl, aryl and alkylaryl acid and their derivatives can be used as acids in the process according to the invention.
  • the inventive method for the conversion of aminosilanes and silanes to functionalized polyhedral oligomeric silsesquioxanes is preferably carried out in solution.
  • solvents both a polar and a nonpolar solvent can be used.
  • the solvents used are preferably halogen-free solvents selected from the group of alcohols, ketones, aldehydes, ethers, acids, esters, anhydrides, alkanes, aromatics and / or nitriles or else a mixture of these solvents.
  • Alcohols, ethers, acetone, acetonitrile, benzene or toluene are particularly preferably used as solvent. Very particular preference is given to using acetone, methanol or ethanol or a mixture of two or more of these compounds as solvent.
  • the reaction of the silanes is carried out in the presence of water.
  • water is added to the reaction mixture or the educt composition.
  • the aminosilane used is modified with an acid.
  • the molar ratio of the aminosilanes to the acid is preferably to be selected such that per one primary, secondary or tertiary amino group of 0.5 to 1.5 molar equivalents of a monoprotic acid are available, but preferably 1 molar equivalent of a monoprotic acid is added.
  • the molar ratio should be chosen so that the amino groups of aminosilane are completely neutralized.
  • the initial concentration of all silanes according to the formulas (R a X b ) m SiY n and A 1n SiY n in the solution is preferably from 0.01 mol / 1 to 10 mol / l, preferably from 0 , 1 mol / 1 to 6 mol / 1, more preferably from 0.3 mol / 1 to 4 mol / 1.
  • the reaction of the silanes and modified aminosilanes in the present process is preferably conducted at a temperature from 0 to 200 0 C, preferably at a temperature of 10 to 150 0 C, particularly preferably at a temperature of 20 to 100 0 C. Most preferably, this reaction of the silanes is carried out at a temperature of 40 to 80 oC.
  • the temperature over the entire reaction time is not kept constant, it is for example advantageous to lower the reaction temperature towards the end of the reaction time in order to be able to completely isolate the functionalized polyhedral oligomeric silsesquioxanes as possible.
  • the process according to the invention can be carried out continuously or batchwise, the reaction of the silanes to give functionalized polyhedral oligomeric silsesquioxanes in a one-step reaction.
  • the reaction of the silanes into functionalized polyhedral oligomeric silsesquioxanes is preferably carried out in the process according to the invention by adding the aminosilane A 1n SiY n or else several aminosilanes
  • the target product can be separated from the reaction mixture in a manner known to the person skilled in the art.
  • the solvent or solvent mixture can be separated from the desired composition of functionalized polyhedral oligomeric silsesquioxanes.
  • the inventive method is particularly suitable for the preparation of a composition of functionalized polyhedral oligomeric silsesquioxanes, which understood in the context of this invention under silsesquioxanes both fully condensed and incompletely condensed silsesquioxanes.
  • Silsesquioxanes are oligomeric or polymeric substances whose fully condensed representatives have the general formula (SiC> 3 / 2R) n, where n> 4 and the radical R can be a hydrogen atom, but mostly an organic
  • R 8 Si 8 On (OH) 2 and R 8 Si 8 Oi 0 (OH) 4 are reacted (Chem. Commun. (1999), 2309-10; Polym. Mater. Sei. Eng. 82 (2000), 301- 2, WO 01/10871) and thus serve as a parent compound for a large number of different incompletely condensed and functionalized silsesquioxanes.
  • the silsesquioxanes (trisilanols) of the formula R 7 Si 7 Og (OH) 3 can be converted into correspondingly modified oligomeric silsesquioxanes by reaction with functionalized monomeric silanes (corner capping).
  • composition according to the invention comprises at least one functionalized polyhedral oligomeric silsesquioxane according to the following formula:
  • R hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked isocyanate, Acrylate, methacrylate, mercapto, nitrile, phosphine or at least one such type X substituent of type R,
  • a f amino, ammonium or at least one amino or ammonium group-containing substituents of type R,
  • composition according to the invention is preferably prepared by the process according to the invention.
  • the composition according to the invention comprises various functionalized polyhedral oligomeric silsesquioxanes, which are characterized in that in addition to the substituents of the type R, they also have substituents of the type A f and, if appropriate, also of the type X.
  • a composition according to the invention may comprise the following functionalized polyhedral, oligomeric silsesquioxanes, as shown in structures 5a, 5b and 5c:
  • composition according to the invention may also contain further functionalized polyhedral oligomeric silsesquioxanes
  • oligomeric silsesquioxanes with a T 8 cage functionalized polyhedral, oligomeric silsesquioxanes with a T 4 , T ⁇ - r Ti 0 or with a Ti 2 cage may also be present.
  • silsesquioxanes with a so-called ladder structure can also be present in the composition according to the invention.
  • At least one of the functionalized polyhedral oligomeric silsesquioxanes has an ammonium group or an ammonium group-containing substituent of type R, the counter anion of the ammonium group being a base of the acid 3,5-di-tert. butyl-4-hydroxybenzoic acid or 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid.
  • the functionalized polyhedral oligomeric silsesquioxanes according to the invention have a structure according to the formula
  • R hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or Heteroaryl group, which are each substituted or unsubstituted,
  • X oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen, epoxy, ester, fluoroalkyl blocked, isocyanate, acrylate, methacrylate, mercapto, nitrile, phosphine group or at least one such type X substituent of type R,
  • a f amino, ammonium or at least one amino or ammonium group-containing substituents of type R,
  • both the substituents of the type R and type A f and the type X are the same or different, and having at least one substituent of the type A f , on.
  • the functionalized polyhedral oligomeric silsesquioxanes of the invention have an ammonium group or an ammonium group-containing substituent of type R, wherein the counter anion of the ammonium group, the base of the acid 3, 5-di-tert. butyl-4-hydroxybenzoic acid or 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid.
  • the functionalized polyhedral, oligomeric silsesquioxanes according to the invention are preferably prepared by means of the process according to the invention or isolated from the composition according to the invention.
  • compositions of the invention can be used to synthesize and modify polymers in a wide range of applications.
  • the inventive Composition can be added to all common polymers. This can be both chemical bonding and pure blending.
  • the rheological properties of a large number of polymers can be favorably influenced, for example the adhesive and bonding properties as well as the barrier action to gases and liquids.
  • organic polymers selected from polyolefins, amorphous polyalphaolefins, polyethers, polyamides, copolyamides, polyamide compounds, polyesters, copolyesters, polyurethanes, polyacrylates, polymethacrylates, polycarbonates, polyurethanes, phenolic resins, epoxy resins, polysiloxanes, polysilanes, rubbers, rubber compounds, polyvinyl chloride, vinyl chloride copolymers, polystyrene , Copolymers of styrene, ABS polymers and Olefinco- and - terpolymere.
  • polymer can be modified or formed by the addition of the composition of the invention or the silsesquioxanes according to the invention to the polymers composites having the desired properties.
  • the polymers modified in this way can be used, for example, in the form of coatings, paints, injection-molded or extruded molded parts, calendered films, lubricants, adhesives, cosmetics, pharmaceuticals, fibers, glass fibers or packaging materials.
  • the composition according to the invention or silsesquioxanes according to the invention it is also possible to apply to a polymer surface.
  • the effect of the inventive composition or silsesquioxanes according to the invention is that in the resulting polymers they increase the glass, decomposition and thus the use temperature, increase the tensile strength, impact strength, scratch resistance and mechanical hardness, reduce the density, the thermal conductivity, lower the thermal expansion coefficient and the dielectric constant and viscosity, change the surface tension and adhesion, decrease the flammability, flammability and heat development, increase the O 2 permeability, increase the oxidation and corrosion stability, simplify the processing, and restrain shrinkage processes.
  • compositions according to the invention or silsesquioxanes according to the invention can furthermore serve as starting compounds for catalysts.
  • metal compounds homogeneous and heterogeneous catalysts can be formed, which in turn can be used for oxidation, metathesis, C-C coupling reactions, oligomerizations, polymerizations, additions, reductions, eliminations, rearrangements.
  • Preference is given to the reaction with metal compounds of metals of the subgroups, the lanthanides, actinides and the 3rd and 4th main group.
  • This high molecular weight stabilizer has the advantage that it shows no migration tendency in a plastic.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne un procédé de production d'une composition contenant des silasesquioxanes fonctionnalisés. L'invention est caractérisée en ce que l'on utilise au moins un aminosilane selon la formule AmSiYn préalablement modifié par un acide, et au moins un silane selon la formule (RaXb)mSiYn. L'invention concerne également des silasesquioxanes oligomères polyédriques fonctionnalisés selon la formule [(RaXbA'rSiO1,5)m (RcXdA'sSiO)n], où A' représente un groupe amino, un groupe ammonium ou au moins un substituant présentant un groupe amino ou un groupe ammonium, une composition contenant ces silasesquioxanes oligomères polyédriques fonctionnalisés et leur utilisation.
PCT/EP2006/061838 2005-05-27 2006-04-26 Composition contenant des silasesquioxanes oligomeres polyedriques fonctionnalises et son procede de production WO2006125708A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005024814.4 2005-05-27
DE200510024814 DE102005024814A1 (de) 2005-05-27 2005-05-27 Funktionalisierte polyedrische oligomere Silasesquioxane aufweisende Zusammensetzung und Verfahren zu deren Herstellung
US73213705P 2005-11-02 2005-11-02
US60/732,137 2005-11-02

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007121908A1 (fr) * 2006-04-20 2007-11-01 Hybrid Catalysis B.V. Procédé de production de d'oligomères polyèdres, de silasesquioxanes, de silasesquioxanes oligomères polyèdres et leur utilisation
DE102009004343A1 (de) 2009-01-12 2010-07-15 Kühnle, Adolf, Dr. Acrylglas mit verbessertem Brandverhalten
WO2020130945A1 (fr) * 2018-12-19 2020-06-25 Agency For Science, Technology And Research Modificateur, matériau argileux modifié, composite et procédés associés
CN113234225A (zh) * 2021-06-10 2021-08-10 山东硅科新材料有限公司 一种简单高效制备t8-poss的方法

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Publication number Priority date Publication date Assignee Title
JPH0347840A (ja) * 1989-04-18 1991-02-28 Shin Etsu Chem Co Ltd 球状ポリオルガノシルセスキオキサン微粒子及びその製造方法
WO2001010871A1 (fr) * 1999-08-04 2001-02-15 Hybrid Plastics Procede de fabrication de silsesquioxanes oligomeres polyedres
WO2003064490A2 (fr) * 2001-06-27 2003-08-07 Hybrid Plastics Llp Procede de fonctionnalisation de silsesquioxanes oligomeres polyhedriques
WO2003097652A1 (fr) * 2002-05-15 2003-11-27 Creavis Gesellschaft Für Technologie Und Innovation Mbh Matiere de remplissage de taille nanometrique, procede de production et utilisation de cette matiere

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Publication number Priority date Publication date Assignee Title
JPH0347840A (ja) * 1989-04-18 1991-02-28 Shin Etsu Chem Co Ltd 球状ポリオルガノシルセスキオキサン微粒子及びその製造方法
WO2001010871A1 (fr) * 1999-08-04 2001-02-15 Hybrid Plastics Procede de fabrication de silsesquioxanes oligomeres polyedres
WO2003064490A2 (fr) * 2001-06-27 2003-08-07 Hybrid Plastics Llp Procede de fonctionnalisation de silsesquioxanes oligomeres polyhedriques
WO2003097652A1 (fr) * 2002-05-15 2003-11-27 Creavis Gesellschaft Für Technologie Und Innovation Mbh Matiere de remplissage de taille nanometrique, procede de production et utilisation de cette matiere

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 199115, Derwent World Patents Index; Class A26, AN 1991-105912, XP002393641 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007121908A1 (fr) * 2006-04-20 2007-11-01 Hybrid Catalysis B.V. Procédé de production de d'oligomères polyèdres, de silasesquioxanes, de silasesquioxanes oligomères polyèdres et leur utilisation
DE102009004343A1 (de) 2009-01-12 2010-07-15 Kühnle, Adolf, Dr. Acrylglas mit verbessertem Brandverhalten
WO2020130945A1 (fr) * 2018-12-19 2020-06-25 Agency For Science, Technology And Research Modificateur, matériau argileux modifié, composite et procédés associés
CN113234225A (zh) * 2021-06-10 2021-08-10 山东硅科新材料有限公司 一种简单高效制备t8-poss的方法
CN113234225B (zh) * 2021-06-10 2022-08-02 山东硅科新材料有限公司 一种简单高效制备t8-poss的方法

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