CN101180301A - Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages - Google Patents
Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages Download PDFInfo
- Publication number
- CN101180301A CN101180301A CNA2006800178737A CN200680017873A CN101180301A CN 101180301 A CN101180301 A CN 101180301A CN A2006800178737 A CNA2006800178737 A CN A2006800178737A CN 200680017873 A CN200680017873 A CN 200680017873A CN 101180301 A CN101180301 A CN 101180301A
- Authority
- CN
- China
- Prior art keywords
- chemical
- alkene
- adhesive power
- property
- poss
- 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.)
- Pending
Links
Images
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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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 System
- 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
- 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
- C08G77/06—Preparatory processes
Abstract
The present invention relates to a method for continuous bulk production of polyolefm (polyolefm) polyhedral oligomeric silsesquioxanes and their amino, isocyanate, and alcohol derivatives using silane coupling agents as precursors.
Description
Related application
It is that the sequence number on May 25th, 2005 is No.60/684 that the application requires to enjoy the applying date, the preference of 666 U.S. Provisional Patent Application.
Invention field
Relate generally to of the present invention contains the method and composition of the polyhedral oligomeric silsesquioxane (POSS) of alkene.More specifically, it relates to the method that continuous batch is produced the POSS of many vinyl and the chemical products of deriving.
Background of invention
The newly-developed of nano science makes the polyhedral oligomeric silsesquioxane of cost-effective ground production commercial quantities become possibility, described polyhedral oligomeric silsesquioxane because their exact chemical formulas, blended (inorganic-organically) chemical constitution, with respect to the big physical size for the size (0.3-0.5nm) of traditional chemical molecule and with respect to traditional weighting agent of large-size (＞little physical size for 50nm) and be described as nanostructured chemicals best.
The commodity of organo silane coupling agent makes them be seen the parent material of POSS molecule by height requirement to be used as nanometer.Prior art has been instructed application (U.S. Patent No. 6,972,312) and the application in the functionalization of the POSS cage that contain reactive group (U.S. Patent No. 6,927,270) of silane coupling agent in the formation of POSS cage.
The present invention instructs continuous production to contain the POSS of alkene and the particularly method of vinyl POSS cage.This progress is essential because vinyl silanes is the minimum reactive silane coupling agent that subtracts this, also because vinyl POSS cage for chemically derived for other chemical group be in demand.The application of alkene POSS and derivative thereof comprises compound resin, coating, coating, tackiness agent and the surface properties of improvement, and described surface properties causes resistivity against fire, printability, biocompatibility and controlled perviousness, high Tg and heat distortion material, vitrifying agent, printing auxiliary agent and nanofiltration material.
Summary of the invention
The present invention describes continuously the synthetic method that contains polyolefinic polyhedral oligomeric silsesquioxane.The composition of the chemical that is obtained by them is also described.
On nanostructured chemicals and nanostructure oligopolymer, contain olefin functionalities (accompanying drawing 1) in this preferred compositions.The classification of described nanostructured chemicals comprises the polymorph of polyhedral oligomeric silsesquioxane, polysilsesquioxane, polyhedral oligomeric silicate, polysilicate, poly-oxometallate, carborane and carbon.The chemical that obtains from the POSS that contains alkene has passed through hydrosilation, phosphorylation and mercaptanization (U.S. Patent No. 5; 939; 576), epoxidation and method for oxidation (U.S. Patent No. 5; 942; 638 and 6; 100,417), cross substitution, Heck addition, Diels-Alder reaction, hydroformylation and Wacker oxidation and prepare.The present invention describes polyisocyanate derivatives, hydrogen amination (dhydroamination) and carboxylation subsequently.The polyol derivative that obtains by oxyethane and propylene oxide and alkene POSS addition is also described.
Multifunctional POSS system works being cross-linked to form in the process of material, and described material is polycarbonate, polyester, urethane, epoxide, polyethers, polymeric amide, polyolefine, bismaleimides, chitin, Mierocrystalline cellulose, poly-acid and silicone for example.
The nanostructured chemicals that contains vinyl is effective especially in polymkeric substance, because their controlling polymers chain and segmental motions on the molecule grade.The nanostructured chemicals that contains vinyl also is in demand in makeup, tackiness agent, coating, coating and dyestuff, because they bring unique surface and physical properties.Nanostructured chemicals is introduced in the polymkeric substance and can be produced favorable influence to most physical propertiess of polymkeric substance.The character of favourable improvement is heat distortion and flammable performance.The character of other improvement comprises for example creep of time dependent machinery and thermal properties, compressive set, contraction, modulus and hardness.Except mechanical properties, other physical properties has also advantageously been improved, and comprises lower heat conductivity, starvation performance and perviousness, surface luster and color.In addition, the nanostructured chemicals that contains vinyl also is very useful in surface vitrification and chemical derivatization.These character of having improved can be used for comprising matrix material and durable coating in many application.
The accompanying drawing summary
Fig. 1 shows the example of the POSS nanostructured chemicals that contains many vinyl;
Fig. 2 graphic extension water is to the influence of eight vinyl POSS productive rates;
Fig. 3 graphic extension acid is to the influence of eight vinyl POSS productive rates;
Fig. 4 shows in batches with quantity-produced eight vinyl POSS's
29The contrast of the NMR collection of illustrative plates of Si;
The aminating process of Fig. 5 graphic extension vinyl hydrogen;
The process that Fig. 6 graphic extension isocyanic ester forms; And
The process that Fig. 7 graphic extension alcohol forms.
The definition of nanostructured developed by molecule formula
In order to understand the thin compound of chemistry of the present invention, polyhedral oligomeric silsesquioxane (POSS) and polyhedron are low The nanostructured developed by molecule formula of polysilicate (POS) is defined as follows.
Polysilsesquioxane is by formula [RSiO1.5] material that x represents, wherein x represents mole of polymerized degree and R=Expression organic substituent group (H, siloxy, ring-type or aliphatic or alkene or aromatic base Group, this group can contain in addition reactive functional groups for example alcohol, isocyanates, ester, amine, ketone, alkene, Ether or halide perhaps can contain the group through fluoridizing). Polysilsesquioxane can be equal fragment or It is the fragment of mixing. All the fragment system only contains one type R group and assorted fragment system contains more than one Type the R group.
POSS and POS nanostructured composition are expressed from the next:
[(RSiO
1.5)
n]
∑#Represent the thin compound of equal fragment
[(RSiO
1.5)
n(R ' SiO
1.5)
m]
∑ #The assorted slice groups compound (wherein R ≠ R ') of expression
[(RSiO
1.5)
n(R * SiO
1.0)
m]
∑ #Expression functionalized heteroleptic composition (wherein the R group can be identical or different)
More than all R identical with above-mentioned definition, and X includes but not limited to OH, Cl, Br, I, alcoholate (OR), acetic ester (OOCR), superoxide (OOR), amine (NR
2), isocyanic ester (NCO) and R.Symbol m and n refer to the stoichiometry of said composition.The symbol ∑ represents that said composition formation nanostructure and symbol # refer to the number of institute's silicon atoms in the nanostructure.The # value is the m+n sum normally, wherein the scope of n generally be from 1 to 24 and the scope of m generally be from 1 to 12.Should be pointed out that ∑ # can not obscure for being used for definite stoichiometric multiplier, because it just describes total nanostructure feature (size of aka cage) of this system.
Detailed description of the Invention
The present invention instruction contains the nanostructured chemicals of alkene and the method for continuous production of its chemical that derives, and the described nanostructured chemicals that contains alkene and its chemical that derives can be used as and strengthen thermosetting resin and thermoplastic resin, oil or contain polymer coil, zone, chain and the segmental module of constructing in aqueous emulsion, latex and the suspension on molecular level.
Nanostructured chemical, for example illustrated alkene POSS structure in the accompanying drawing 1 can exist with the form of solid, wax and oil.Multiple alkene R group for example cyclohexenyl, norbornene, allyl group and styryl can be considered to be included on the nanostructured chemicals.But, least cost and also be commercially available system commercial be vinyl silanes.Vinyl trialkyl oxysilane and vinyl trichloro silane can have been bought with commercial quantities on market.In history, it is unrepeatable that the synthetic method of vinyl POSS system is considered to low-yield, long reaction times and productive rate.The synthetic chemical equation that relates to the vinyl POSS of trichlorine or organoalkoxysilane generally can be expressed from the next:
ViSiCl
3+ H
2O → vinyl POSS+HCl (1)
ViSi (OR)
3+ H
2O+HCl → vinyl POSS+ROH (2)
ViSiCl
3+ MeOH → vinyl POSS+HCl (3)
Chemical reaction shown in the reaction formula 1,2 and 3 is represented with non-stoichiometric form, because the effect of water, HCl, ROH (alcohol) and silane concentration have remarkable influence for the productive rate of product and the purity of separated products.Alkene POSS structure miscellaneous can obtain, as shown in accompanying drawing 1.
For this point is described, accompanying drawing 2 and 3 is described water and sour complex relationship with respect to vinyl POSS cage productive rate.Further, the concentration of acid can change between 1% to 39% in the reaction formula 2 and 3, and preferred concentration is 37.9%.
In the design of continuation method, also need to recognize chemical stability and the ability that alkene POSS product is separated from reaction medium.In reaction formula 1-3, described vinyl POSS for reaction medium be chemically stable be again insoluble.In reaction medium, the insolubility of described POSS product makes that collecting this product by filter reaction mixture becomes easy.The collection of product becomes easily by at room temperature carrying out this reaction further, can avoid like this owing to reacting at elevated temperatures or dissolving the loss that causes product.
The concentration that adds to the silane of reaction medium can change between 0.01M-5.0M.The preferred concentration range for that is used for the successive reaction purpose is from 0.3M to 2.0M, and preferred concentration is 1.3M-1.5M.
When all having set up continuation method for each reaction shown in the reaction formula 1-3, reaction formula 1 and 3 is not to cater to the need so, because they need facility investment to handle corrodibility HCl by product.Although use plastics or the glass-lined container and the filter plant that can obtain easily, reaction formula 2 is easier to operation.
Should further mention, reaction formula 1 and 3 produces three equivalent HCl with respect to each equivalent vinyl trichloro silane, and reaction formula 2 produces three equivalent alcohol with respect to each equivalent vinyl trialkyl oxysilane.The release of alcohol is needs highly in the reaction formula 2, because it helps the dissolving of parent material and the dissolving of vinyl POSS intermediate and resinous.In reaction formula 1 and 3, need alcohols to come the final POSS product of rinsing to remove such intermediate, oligopolymer and polymkeric substance.
At last, the formation of vinyl POSS promotes by be settled out described product from described acidity alcohol solution among the reaction formula 1-3.Produced resinous in this reaction, but it is not precipitated out from this reaction yet, soluble because it remains in methyl alcohol.
Embodiment
For all methods general method variable applicatory
This is general with regard to chemical process, has many variablees to can be used for controlling purity, selectivity, speed and the mechanism of any means.Influence forms for example catalyzer, promotor, carrier and tensio-active agent and for example temperature, pressure, template, solvent, gas and their mixing of other factors of auxiliary agent that the variable of the method for nanostructured chemicals (for example POSS/POS etc.) comprises size, polymolecularity and composition, kinetics, the thermodynamics of needed nanostructured chemicals and uses in reaction process.
Vinyl POSS can produce from vinyltrimethoxy silane, vinyltriethoxysilane or vinyl trichloro silane (perhaps Xiang Guan derivative) via per 24 hours filtration product or by filtering described product at continuous 24 hours after the interpolation silane and obtain.Filtration in general preferred per 24 hours is also collected described reaction product once.
Embodiment 1-vinyl trichloro silane method
From vinyl trichloro silane when synthetic, described vinyl trichloro silane and 3.5 equivalent methyl alcohol pre-mixings 10 minutes.Subsequently described pre-reaction solution (0.85%) is added in the solution of methyl alcohol (65.7%v/v), HCl (32.7%v/v) and water (0.65%v/v) of stirring.Need regularly to add the methyl alcohol of meltage to minimize the formation that to pollute the sticky white resinous by product of described eight vinyl POSS.The amount of required MeOH is variable and it is determined by the visible dissolving of any viscous precipitate resin on the reactor vessel wall.
Embodiment 1a
In the 1000mL round-bottomed flask that accommodates methyl alcohol (500mL), HCl (250ml) and water (5mL), make described mixture reach room temperature.Slowly add vinyltrimethoxy silane (6.5mL) to described reaction mixture, and will be reflected under the stirring (magnetic stirring apparatus) and carry out continuously 24 hours.In one case, add other silane (6.5mL) with its filtration and in described reactor, and described process is repeated 5 to 20 times.Add and filter generation 35.3%Vi8T8 20 times.(productive rate crosses in methanol wash and dried final product comes.) 10 times add and do not filter and produce 32.8%Vi8T8.(productive rate in methyl alcohol and washing with acetone cross and vacuum-drying after final product come.)
Embodiment 1b
In the 1000mL round-bottomed flask that accommodates methyl alcohol (500mL), HCl (250ml) and water (5mL), make described mixture reach room temperature through slow interpolation.Slowly add vinyltrimethoxy silane (6.5mL) to described reaction mixture, and will be reflected under the stirring (magnetic stirring apparatus) and carry out continuously 24 hours.5 times interpolation/filtering overall yield is 40.8%.5 times interpolation/filtering overall yield is 40.8%.(productive rate crosses in methanol wash and dried final product comes.)
Embodiment 2-vinyl trialkyl oxysilane method
The method of producing eight vinyl POSS from vinyltrimethoxy silane comprises at room temperature per 24 hours and adds described silane (0.85%v/v) to the solution of the methyl alcohol (65.7%v/v) that stirs, HCl (32.7%v/v), water (0.65%v/v).Described reaction mixture can be via the continuous filtration product or by adding silane and continuous production eight vinyl POSS continuously.
Perhaps, in the 1000mL round-bottomed flask that accommodates methyl alcohol (500mL), HCl (250ml) and water (5mL), make described mixture reach room temperature through slow interpolation.Slowly add vinyltrimethoxy silane (6.5mL) to described reaction mixture, and will be reflected under the stirring (magnetic stirring apparatus) and carry out continuously 24 hours.In one case, add other silane (6.5mL) with its filtration and in described reactor, and described process is repeated 5 to 20 times.In another case, in described reactor, add other silane (6.5mL), and described process is repeated 5 to 20 times.
The hydrogen amination of embodiment 3-vinyl POSS
The hydrogen amination of alkene is a kind of reaction that is widely known by the people.The hydrogen amination of accompanying drawing 5 graphic extension vinyl POSS.50g vinyl POSS sample is suspended in the liquid ammonia solution, and to wherein adding PtBr
2And nBu
4PBr.Make described mixture reaction surpass 8 hours to produce eight required amino-ethyl POSS.Isolate the described product of white solid.
The formation of embodiment 4-polymeric polyisocyanate
With 50g eight amino-ethyl POSS samples 50 ℃ down and phosgene reaction 4 hours to produce described octaethyl isocyanic ester POSS.Isolate the described product of white solid.The formation of the polymeric polyisocyanate of accompanying drawing 6 graphic extension POSS.
The hydrolysis oxidation reaction of embodiment 5-vinyl POSS
Transition metal oxide is OsO for example
4And MnO
4 -Be considered to strong oxygenant always.The catalytic osmium formula of amine is reacted (osmylation) and then is hydrolyzed is a kind of currently known methods from vinyl groups production diol product.50g vinyl POSS sample is stirred in the perosmic anhydride.Make described mixture reaction 2 hours and subsequently with aqueous acids washing to produce white solid octaethyl ethylene glycol POSS, it is collected by filtering.Accompanying drawing 7 schematically shows the process that alcohol forms.
Below provide some representational embodiment and details for the purpose of illustrating the invention, for a person skilled in the art, can be to carrying out various variations under the situation that does not deviate from scope of the present invention at this disclosed method and apparatus, this will be conspicuous, and scope of the present invention is limited by appended claim.
Claims (17)
1. a manufacturing contains the method for the chemical of alkene, its silane coupling agent that comprises the following steps: that (a) will contain alkene mixes with the chemical that is selected from polyhedral oligomeric silsesquioxane and polyhedral oligomeric silicate in the presence of acidity or basic catalyst and water, and (b) collects the described chemical that contains alkene by filtering.
2. the process of claim 1 wherein that most silane coupling agents are used for different functional groups is introduced among the described chemical.
3. the process of claim 1 wherein that described method is with successive or the use of batch-wise manufacture method.
4. the process of claim 1 wherein that described reaction medium does not heat by the external source that is higher than 40 ℃.
5. the process of claim 1 wherein that the described physical condition that contains the chemical of alkene is selected from oily, amorphous, hypocrystalline, crystallization, elastomerics, rubber and cross-linked material.
6. the method for claim 2, the wherein said chemical that contains alkene comprises nonreactive R group.
7. the method for claim 1 further comprises making the described aminating step of chemical that contains alkene.
8. the method for claim 7, wherein said amination changes the physical properties of described chemical, and it is selected from adhesive power to polymeric surface, to the adhesive power of compound surface, adhesive power, water resisting property, density, low-k, heat conductivity, glass transition, viscosity, melting transition, storage modulus, relaxation, stress transmission, abrasion resistance, resistivity against fire, biocompatibility, ventilation property and porosity to the metallic surface.
9. the method for claim 1 further comprises making the described step that contains the chemical isocyanation esterification of alkene.
10. the method for claim 9, wherein said isocyanation esterification changes the physical properties of described chemical, and it is selected from adhesive power to polymeric surface, to the adhesive power of compound surface, adhesive power, water resisting property, density, low-k, heat conductivity, glass transition, viscosity, melting transition, storage modulus, relaxation, stress transmission, abrasion resistance, resistivity against fire, biocompatibility, ventilation property and porosity to the metallic surface.
11. the method for claim 1 further comprises making the described step that contains the chemical oxidation of alkene.
12. the method for claim 11, wherein said oxidation changes the physical properties of described chemical, its be selected from adhesive power to polymeric surface, to the adhesive power of compound surface, to the metallic surface adhesive power, water resisting property, density, low-k, heat conductivity, glass transition, viscosity, melting transition, storage modulus,, stress transmission, abrasion resistance, resistivity against fire, biocompatibility, ventilation property and porosity.
13. the method for claim 1 further comprises the step of the described chemical that contains alkene being introduced the product that is selected from fabric, dyestuff, hair coloring agents, lustering agent, emulsifiable paste, washing lotion, lipstick, Mascara, foundation cream, soap, absorption agent and makeup.
14. the method for claim 13, the wherein said step that the described chemical that contains alkene is introduced changes the physical properties that is selected from adhesive power, water resisting property, density, oilness, luminous, viscosity, modulus, filler reinforcement, plastification, relaxation, stress transmission, abrasion resistance, radiation resistance, biocompatibility, ventilation property, porosity, protection against the tide and gas barrier properties, glass formation, electrostatic dissipation, the biology property killed, nutrient release, exfoliation, dispersion assistance and intensity to the surface.
15. the method for claim 6 further comprises the step of the described chemical that contains alkene being introduced the product that is selected from fabric, dyestuff, hair coloring agents, lustering agent, emulsifiable paste, washing lotion, lipstick, Mascara, foundation cream, soap, absorption agent and makeup.
16. the method for claim 15, the wherein said step that the described chemical that contains alkene is introduced changes the physical properties that is selected from adhesive power, water resisting property, density, oilness, luminous, viscosity, modulus, filler reinforcement, plastification, relaxation, stress transmission, abrasion resistance, radiation resistance, biocompatibility, ventilation property, porosity, protection against the tide and gas barrier properties, glass formation, electrostatic dissipation, the biology property killed, nutrient release, exfoliation, dispersion assistance and intensity to the surface.
17. the process of claim 1 wherein that the described chemistry that contains alkene comprises epoxide modified vinyl composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68466605P | 2005-05-25 | 2005-05-25 | |
| US60/684,666 | 2005-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101180301A true CN101180301A (en) | 2008-05-14 |
Family
ID=37452373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006800178737A Pending CN101180301A (en) | 2005-05-25 | 2006-05-25 | Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1888599A4 (en) |
| JP (1) | JP2008545709A (en) |
| KR (1) | KR20080029970A (en) |
| CN (1) | CN101180301A (en) |
| RU (1) | RU2007148695A (en) |
| SG (1) | SG170026A1 (en) |
| TW (1) | TW200700427A (en) |
| WO (1) | WO2006128052A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106336425A (en) * | 2016-08-24 | 2017-01-18 | 陕西天策新材料科技有限公司 | Continuous production technology for preparing POSS by hydrolytic condensation method and equipment thereof |
| CN108940367A (en) * | 2018-06-28 | 2018-12-07 | 南京荣欣化工有限公司 | A kind of preparation method of the catalyst for hydroformylation of olefin |
| CN109517312A (en) * | 2018-11-22 | 2019-03-26 | 陕西科技大学 | A kind of double POSS polyethers hydridization PMMA resins and its preparation, forming method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007022367A2 (en) * | 2005-08-16 | 2007-02-22 | Hybrid Plastics, Inc. | Preparation of polyhedral oligomeric silsesquioxane silanols and siloxides functionalized with olefinic groups |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3635180B2 (en) * | 1997-02-24 | 2005-04-06 | ダウ コーニング アジア株式会社 | Silylated polymethylsilsesquioxane, process for producing the same, and composition using the same |
| US5942638A (en) * | 1998-01-05 | 1999-08-24 | The United States Of America As Represented By The Secretary Of The Air Force | Method of functionalizing polycyclic silicones and the resulting compounds |
| US6911518B2 (en) * | 1999-12-23 | 2005-06-28 | Hybrid Plastics, Llc | Polyhedral oligomeric -silsesquioxanes, -silicates and -siloxanes bearing ring-strained olefinic functionalities |
| US6100417A (en) * | 1999-08-31 | 2000-08-08 | The United States Of America As Represented By The Secretary Of The Air Force | Functionalizing olefin bearing silsesquioxanes |
| DE10156619A1 (en) * | 2001-11-17 | 2003-05-28 | Creavis Tech & Innovation Gmbh | Process for the preparation of functionalized oligomeric silasesquioxanes and their use |
| WO2003042292A2 (en) * | 2001-11-17 | 2003-05-22 | Creavis Gesellschaft Für Technologie Und Innovation Mbh | Polyolefin compositions, method for the production thereof and the use of these compositions |
| JP4742212B2 (en) * | 2002-08-06 | 2011-08-10 | Ｊｎｃ株式会社 | Process for producing silsesquioxane derivative and silsesquioxane derivative |
| JP4256756B2 (en) * | 2002-09-30 | 2009-04-22 | 新日鐵化学株式会社 | Method for producing cage-type silsesquioxane resin having functional group |
-
2006
- 2006-05-24 TW TW095118439A patent/TW200700427A/en unknown
- 2006-05-25 KR KR1020077030138A patent/KR20080029970A/en not_active Application Discontinuation
- 2006-05-25 CN CNA2006800178737A patent/CN101180301A/en active Pending
- 2006-05-25 SG SG201101296-0A patent/SG170026A1/en unknown
- 2006-05-25 EP EP06771393A patent/EP1888599A4/en not_active Withdrawn
- 2006-05-25 RU RU2007148695/04A patent/RU2007148695A/en not_active Application Discontinuation
- 2006-05-25 JP JP2008513782A patent/JP2008545709A/en active Pending
- 2006-05-25 WO PCT/US2006/020601 patent/WO2006128052A1/en active Application Filing
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106336425A (en) * | 2016-08-24 | 2017-01-18 | 陕西天策新材料科技有限公司 | Continuous production technology for preparing POSS by hydrolytic condensation method and equipment thereof |
| CN106336425B (en) * | 2016-08-24 | 2019-06-18 | 陕西天策新材料科技有限公司 | A kind of hydrolytic condensation method prepares the continuous production technology and equipment of POSS |
| CN108940367A (en) * | 2018-06-28 | 2018-12-07 | 南京荣欣化工有限公司 | A kind of preparation method of the catalyst for hydroformylation of olefin |
| CN109517312A (en) * | 2018-11-22 | 2019-03-26 | 陕西科技大学 | A kind of double POSS polyethers hydridization PMMA resins and its preparation, forming method |
| CN109517312B (en) * | 2018-11-22 | 2021-01-29 | 陕西科技大学 | Dual POSS polyether hybrid PMMA resin and preparation and forming methods thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1888599A4 (en) | 2011-02-09 |
| SG170026A1 (en) | 2011-04-29 |
| RU2007148695A (en) | 2009-06-27 |
| JP2008545709A (en) | 2008-12-18 |
| KR20080029970A (en) | 2008-04-03 |
| TW200700427A (en) | 2007-01-01 |
| WO2006128052A1 (en) | 2006-11-30 |
| EP1888599A1 (en) | 2008-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7888435B2 (en) | Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages | |
| US6927270B2 (en) | Process for the functionalization of polyhedral oligomeric silsesquioxanes | |
| US6271292B1 (en) | Organic-inorganic hybrid materials | |
| US8415446B2 (en) | Cardanol based dimers and uses therefor | |
| JP2583412B2 (en) | Hydroxyl group-containing siloxane compound | |
| CN1989180B (en) | Method for the manufacture of polybranched organic/inorganic hybrid polymers | |
| JP5018065B2 (en) | Polysiloxane compound and method for producing the same | |
| CN101180301A (en) | Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages | |
| JP2678624B2 (en) | Organosiloxane compound having amino group | |
| CN117561294A (en) | Siloxane-based polymeric materials for efficient rearrangement and curing reactions and having specific degrees of polymerization | |
| JP6140721B2 (en) | Method for producing an organic-inorganic hybrid material | |
| JP2003012803A (en) | Alkoxysilyl functional silicone liquid resin, its production method and curable silicone resin composition | |
| CN107365395B (en) | Organosiloxane-grafted polyvinyl alcohol polymer and method for producing same | |
| CN100436458C (en) | Process for the production of silanol containing organopolysiloxanes | |
| JP2538308B2 (en) | Organosiloxane | |
| CN102649844B (en) | Preparation method of functionalized terminal group polysiloxane | |
| JP2715652B2 (en) | Method for producing hydrogen polysiloxane | |
| JP2544033B2 (en) | Method for producing carboxy functional silicone | |
| JPH0370737A (en) | Organopolysiloxane and its preparation | |
| US7432387B2 (en) | Process for producing organosilicon compound | |
| JP2008537731A (en) | Process for building POSS monomers | |
| JP2008266301A (en) | New silicone compound, and raw material thereof and method for producing the silicone compound | |
| US7485692B2 (en) | Process for assembly of POSS monomers | |
| US6555644B2 (en) | Multi-reactive silicon compound having polyalkyleneglycol substituents and synthetic method thereof | |
| KR101621576B1 (en) | Process for producing silicon compound having oxetanyl group |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20080514 |