EP2429720A2 - Composés d'ester de phénolate - Google Patents

Composés d'ester de phénolate

Info

Publication number
EP2429720A2
EP2429720A2 EP10724253A EP10724253A EP2429720A2 EP 2429720 A2 EP2429720 A2 EP 2429720A2 EP 10724253 A EP10724253 A EP 10724253A EP 10724253 A EP10724253 A EP 10724253A EP 2429720 A2 EP2429720 A2 EP 2429720A2
Authority
EP
European Patent Office
Prior art keywords
bis
hydroxyphenyl
silane
propane
compound
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Withdrawn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
EP10724253A
Other languages
German (de)
English (en)
Inventor
Stefan Sepeur
Frank Gross
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.)
Nano X GmbH
Original Assignee
Nano X GmbH
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 Nano X GmbH filed Critical Nano X GmbH
Publication of EP2429720A2 publication Critical patent/EP2429720A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
    • C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
    • C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
    • C23C18/1204—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material inorganic material, e.g. non-oxide and non-metallic such as sulfides, nitrides based compounds
    • C23C18/1208—Oxides, e.g. ceramics
    • C23C18/1216—Metal oxides
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
    • C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
    • C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
    • C23C18/1204—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material inorganic material, e.g. non-oxide and non-metallic such as sulfides, nitrides based compounds
    • C23C18/122—Inorganic polymers, e.g. silanes, polysilazanes, polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
    • C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
    • C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
    • C23C18/125—Process of deposition of the inorganic material
    • C23C18/1254—Sol or sol-gel processing
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
    • C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
    • C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
    • C23C18/125—Process of deposition of the inorganic material
    • C23C18/1262—Process of deposition of the inorganic material involving particles, e.g. carbon nanotubes [CNT], flakes
    • C23C18/127—Preformed particles
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
    • C23C18/14—Decomposition by irradiation, e.g. photolysis, particle radiation or by mixed irradiation sources
    • C23C18/143—Radiation by light, e.g. photolysis or pyrolysis
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D13/00—Electrophoretic coating characterised by the process
    • C25D13/02—Electrophoretic coating characterised by the process with inorganic material
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D13/00—Electrophoretic coating characterised by the process
    • C25D13/04—Electrophoretic coating characterised by the process with organic material

Definitions

  • the invention relates to phenolate ester compounds.
  • polycarbonate a compound of phosgene and bisphenol A
  • polycarbonate a compound of phosgene and bisphenol A
  • the preparation of polycarbonates from phenols or biphenols is known from EP 1 425 332 B1.
  • the linkage is via the formation of a phenolate ester Ph-OC (Ri -3 ), wherein the radicals Ri -3 is generally hydrogen, another carbon atom, oxygen or nitrogen.
  • silanes are known having hydrolyzable groups, generally methoxy or Ethoxy-silanes, which can form inorganic networks after hydrolysis and condensation.
  • a process for electrocoating electrically non-conductive substances in which a firmly adhering electrically conductive layer is produced on the substrates by plasma polymerization, the coated substrates after immersion in an aqueous cathodic or anodically depositable dip paint as a cathode or Anode are switched, with DC a paint layer is deposited, the substrates are removed from the electrodeposition paint and the paint is crosslinked.
  • electrochemical dip coating in the form of cathodic dip coating KTL
  • KTL cathodic dip coating
  • the paint separation occurs as a result of chemical conversion of the binder.
  • the basic principle of electrocoating is to precipitate water-soluble binders on the surface of the paint material connected as an electrode and thus to produce a closed, adhering paint film. This is composed of an epoxy resin dispersion with Pigment Listellstoffen. It is applied by an electric current flow from an outer electrode (anode) via the conductive paint to the Lackiergut (cathode).
  • the result of the KTL is a very uniform coating of metal surfaces and cavities with uniform layer thicknesses and good surface qualities.
  • Electrocoating means that the lacquer emulsion drops are destroyed at the interface and a layer is formed with the discharged particles.
  • the disadvantage is that with the electro-dip method no coatings and coatings can achieve high scratch and abrasion resistance, which makes the additional use of fillers necessary.
  • Another disadvantage of current electrocoating is that the metal pigments of the coating by the contact with the aqueous medium gas or are so integrated into the matrix that cathodic protection is no longer possible.
  • the object of the invention is to provide a new product class which is suitable as a coating material.
  • This object is achieved according to the invention by a compound which contains a chemical structure with the following formula or consists of such a structure:
  • R 1 OH, H, OY or an organic side chain
  • R 2 alkyl group or functional organic side chain
  • R 3 an identical or different from R 2 kind organic side chain
  • Ph aryl group
  • an aryl group that is, an aromatic substituent
  • an ester for example, when the element X is silicon and the aryl group Ph is a phenyl radical (C O H S -), a so-called "phenoxy silane ester" having a phenyl-O-Si bond is formed.
  • hydrolysis-stable and highly chemical-stable materials are obtained by transesterification of silanes with phenolic compounds.
  • the aryl group Ph part of an organic compound containing phenol, cresol (o-, m-, p-Kieso ⁇ ), naphthol (a-, ß-naphthol), thymol, catechol, resorcinol, hydroquinone, 1 , 4-naphthohydroquinone, phloroglucinol (1,3,5-trihydroxybenzene), lignin, pyrogallol (1,2,3-trihydroxybenzene, hydroxyhydroquinone (1,2,4-trihydroxybenzene), hydroquinone, resorcinol, dihydroxybiphenyl, bis (hydroxyphenyl ) -alkanes, bis (hydroxyphenyl) -cycloalkane, bis (hydroxyphenyl) sulfide, bis (hydroxyphenyl) ether, bis (hydroxyphenyl) ketone, bis (hydroxyphenyl) sulfone, bis (
  • the silane used for the preparation consists of the group consisting of aminopropyltriethoxysilane (APTES), aminoethylaminopropyltrimethoxysilane,
  • Benzylaminoethylaminopropyltrimethoxysilan vinylbenzyl aminoethylaminopropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane (VTEOS), vinyldimethoxymethylsilane, vinyl (tris) methoxyethoxy) silane, Vinylmethoxymethylsilan, vinyltris (2-methoxyethoxy) silane, vinyltriacetoxysilane, 3-glycidoxypropyltrimethoxysilane, 3- glycidoxypropyltriethoxysilane, glycidoxypropylmethyldiethoxysilane, mercaptopropyl trimethoxysilane, bis Triethoxysilylpropyldisulfidosilane, bis-triethoxysilylpropyltetroasulfidosilane, cyclohexylaminomethyldiethoxysilane, N-cyclohexyla
  • Ethyltriacetosilane (ETA), 3-isocyanatopropyltriethoxysilane (ICTES), methyltriacetoxysilane, mercaptopropyltriethoxysilane, mercaptopropyltrimethoxysilane, N-
  • Hexadecyltriethoxysilane is selected.
  • the invention relates to a process for preparing a phenolate ester compound described in formula 1, wherein a phenolic compound with a silane at temperatures of 60-200 ° C, preferably from 100-150 0 C with the addition of 0 to 5 wt .-% of catalysts Expulsion of the alcohol is heated.
  • the catalysts are selected from the group consisting of acids, bases, Lewis acids, Lewis bases, titanium, aluminum, tin or zirconium complexes or other transition metal complexes, salts or particles, preferably micro- or nanoparticles.
  • At least 10% by weight, preferably at least 25% by weight, of the alkoxy groups and particularly preferably all alkoxy groups are transesterified.
  • At least 25 mol% of the functional groups are Ph-O-Si bonds.
  • a polar or nonpolar solvent in particular an aprotic solvent, which does not tend to transesterify.
  • a polar or nonpolar solvent include, for example, nonpolar hydrocarbons such as xylene or hexane and white spirits or polar acetates such as butyl acetate (BA) or l-methoxy-2-propyl acetate (MPA).
  • BA butyl acetate
  • MPA l-methoxy-2-propyl acetate
  • ketones such as methyl ethyl ketone (MEK) or ethers such as dibutyl ether or tetrahydrofuran. If necessary, the solvent can later be separated again by distillation, precipitation or other separation processes.
  • the use of the compound according to the invention as by a wet chemical method in particular by spraying, pouring, flooding, dipping, spinning, rolling or printing, be applied to a substrate, curable coating material.
  • sol-gel systems are not to be applied in the electrodeposition bath.
  • the reasons given are the high alcohol content and the small size of the condensates.
  • silicate materials can also be deposited in the electrodeposition bath by the following process steps, as described in the patent EP 355 993 B1 for the preparation of low-solvent sol-gel systems: 1. precipitation of a condensate phase,
  • the phenolate ester compound according to the present invention can be precipitated and is thus suitable for electrochemical dip coating as a coating method.
  • the cathodic electrodeposition coating (KTL) is preferred, but also the anodic electrodeposition coating (ATL) is possible.
  • this coating method can also be used in sol-gel systems for the cathodic protection of metallic components and for joining the same or different metals with a higher standard potential than that of the coating. It is particularly suitable for the production of corrosion-resistant vehicle components, body parts and components made of metals for the furniture industry and the construction industry.
  • Preferred metals in this case are those from the group consisting of steel, aluminum, magnesium, zinc, aluminum / steel, magnesium / aluminum, magnesium / aluminum / steel and also alloys thereof.
  • the sol-gel material is prepared by hydrolysis and condensation of a silane and / or an alkoxide and / or several alkoxides with subsequent addition of excess water to the reaction mixture until phase separation into an aqueous phase and a condensate phase begins. Thereafter, the separation (by precipitation) of the condensate phase, which contains the sol-gel material.
  • the sol-gel material preferably contains 0 to 90 wt .-%, preferably 5 to 30 wt .-%, particularly preferably 5 to 20 wt .-% (based on the dry, cured coating) of anti-corrosive pigments consisting of the group are selected from metal pigments, mixtures of metal pigments and metal alloy pigments, or mixtures of metal alloy pigments.
  • the anticorrosive pigments are metal pigments selected from the group consisting of silicon, copper, tin, nickel, zinc, iron, chromium, niobium, vanadium, manganese, aluminum, titanium, beryllium, magnesium, cerium, lanthanum, sodium, calcium, Barium, potassium and Lithiumhaitigen powders or mixtures or alloys thereof, which are up to 90 wt .-%, preferably from 30 to 90 wt .-%, particularly preferably from 40 to 80 wt .-% in the dried coating material ,
  • the anticorrosive pigments may also be oxides and salts, in particular phosphates, chromates, acetates or hydroxides selected from the group consisting of copper, tin, nickel, zinc, chromium, niobium, vanadium , manganese, aluminum, titanium, beryllium, magnesium, cerium, iron, lanthanum, sodium, calcium, barium, potassium and lithium-containing pigments, or of mixtures or alloys thereof, up to 90 wt .-%, preferably from 30 to 90 wt .-%, particularly preferably from 40 to 80 wt .-% are contained in the dried coating material.
  • oxides and salts in particular phosphates, chromates, acetates or hydroxides selected from the group consisting of copper, tin, nickel, zinc, chromium, niobium, vanadium , manganese, aluminum, titanium, beryllium, magnesium, cerium, iron, lanthanum, sodium, calcium,
  • lubricants or surfactants may be added as emulsifiers.
  • the resulting coating After the electromachine and the subsequent hardening process, the resulting coating reaches a layer thickness of 1 to 100 ⁇ m, preferably of 5 to 25 ⁇ m.
  • the compound is cured after application at temperatures from room temperature to 250 ° C, preferably from room temperature to 200 ° C, wherein the curing is preferably carried out thermally, with microwave radiation or UV radiation.
  • the invention provides that the substrate made of glass, ceramic, wood, metal, stone, plastic and / or concrete.
  • the invention will be explained in more detail with reference to embodiments.
  • Example 1 (coating material):
  • the resulting resin is diluted with 40 g of 1-methoxy-2-propanol and admixed with 4.0 g of x-add® KR 9006 (NANO-X GmbH, AI starter) and 0.2 g of Byk 301 (Byk-Chemie) ,
  • the material is sprayed on stainless steel and cured at 180 ° C for 15 min.
  • the dry film thickness can be adjusted to 2 to 40 ⁇ m.
  • the coating shows good resistance to 3% potassium hydroxide solution and to 1% sulfuric acid (24 h exposure at room temperature).
  • the resulting ethanol is distilled off with the formic acid (heating 100 ° C bath temperature for 2 h).
  • 120 g of zinc pigments (Eckart Stapa Zinc 4) are dispersed in the cooled reaction product.
  • the finished mixture is filled with stirring with 800 g of deionized water and dispersed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Electrochemistry (AREA)
  • Ceramic Engineering (AREA)
  • Nanotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des composés d'ester de phénolate. Pour permettre l'obtention d'une nouvelle catégorie de produits adaptés en tant que matériau de revêtement, l'invention a pour objet la préparation d'un composé qui comprend une structure chimique de formule générale [R1 - Ph - O]aX (R2)b (R3)c (OR)n-a-b-c dans laquelle : X = Si, Ti, Zr, Mo, Mn, Cr, W, Hf, Ge, Sn, Pb et n=4; ou X= B, V, Al, Ga, In et n=3; ou X= Zn, Ni, Cu, alcalino-terreux et n= 2; R1 = O-H, H, O-Y ou une chaîne latérale organique; Y = un élément de même type que X ou d'un type différent et comprenant des substituants correspondants; R2 = un groupe alkyle ou une chaîne latérale organique fonctionnelle; R3 = une chaîne latérale organique du même type que R2 ou d'un type différent; Ph = un groupe aryle; R = un groupe alkyle; a est un nombre entier entre 1 et n; b= 0 ou 1; et c= 0 ou 1 avec a+b+c = n. L'invention a également pour objet un composé dans lequel un groupe aryle est combiné à un ester par un groupe O-X. Étonnamment, il s'est avéré qu'une transestérification de silanes avec des composés phénoliques permet d'obtenir des matériaux stables à l'hydrolyse et de stabilité chimique élevée.
EP10724253A 2009-05-14 2010-05-04 Composés d'ester de phénolate Withdrawn EP2429720A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009021388A DE102009021388A1 (de) 2009-05-14 2009-05-14 Phenolatesterverbindungen
PCT/DE2010/000500 WO2010130241A2 (fr) 2009-05-14 2010-05-04 Composés d'ester de phénolate

Publications (1)

Publication Number Publication Date
EP2429720A2 true EP2429720A2 (fr) 2012-03-21

Family

ID=42670425

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10724253A Withdrawn EP2429720A2 (fr) 2009-05-14 2010-05-04 Composés d'ester de phénolate

Country Status (4)

Country Link
US (1) US20120059116A1 (fr)
EP (1) EP2429720A2 (fr)
DE (1) DE102009021388A1 (fr)
WO (1) WO2010130241A2 (fr)

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CN102731829B (zh) * 2012-07-17 2013-08-07 苏州科技学院 新型硅卤协同双硅酸酯阻燃剂化合物及其制备方法
CN102731825B (zh) * 2012-07-17 2013-07-17 苏州科技学院 含氯、溴硅酸酯阻燃剂化合物及其制备方法
CN102731830B (zh) * 2012-07-17 2013-08-07 苏州科技学院 含氮氯代多硅酸酯化合物及其制备方法
CN102898450B (zh) * 2012-07-17 2015-02-25 苏州科技学院 含溴双硅酸酯阻燃剂化合物及其制备方法
CN102731826B (zh) * 2012-07-17 2013-08-07 苏州科技学院 阻燃剂卤代四芳基硅酸酯化合物及其制备方法
CN102731551B (zh) * 2012-07-17 2015-02-25 苏州科技学院 硅卤协同阻燃剂化合物及其制备方法
CN102731828B (zh) * 2012-07-17 2013-10-09 苏州科技学院 含氯溴双硅酸酯阻燃剂化合物及其制备方法
RU2710814C2 (ru) 2013-03-16 2020-01-14 Прк-Десото Интернэшнл, Инк. Золь-гель композиции, ингибирующие коррозию

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Also Published As

Publication number Publication date
US20120059116A1 (en) 2012-03-08
WO2010130241A2 (fr) 2010-11-18
WO2010130241A3 (fr) 2011-01-06
DE102009021388A1 (de) 2010-11-18

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