EP2178984A1 - Système de revêtement aqueux à base de silanes, sa préparation et son utilisation - Google Patents

Système de revêtement aqueux à base de silanes, sa préparation et son utilisation

Info

Publication number
EP2178984A1
EP2178984A1 EP08785901A EP08785901A EP2178984A1 EP 2178984 A1 EP2178984 A1 EP 2178984A1 EP 08785901 A EP08785901 A EP 08785901A EP 08785901 A EP08785901 A EP 08785901A EP 2178984 A1 EP2178984 A1 EP 2178984A1
Authority
EP
European Patent Office
Prior art keywords
acid
formula
reaction
water
silanes
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Withdrawn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
EP08785901A
Other languages
German (de)
English (en)
Inventor
Adolf KÜHNLE
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa 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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2178984A1 publication Critical patent/EP2178984A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • 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
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • Silane-based and aqueous coating system its preparation and use
  • the invention relates to a water-dispersed coating composition based on silanes with amino groups and a double bond-containing organic acid. Furthermore, the invention relates to a process for their preparation and use.
  • aqueous coating systems are generally subdivided into dispersions and emulsions, where the term dispersion denotes the state of aggregation for a finely divided solid in a liquid, while a finely and homogeneously distributed liquid is used under an emulsion Phase in a second fluid understands.
  • So-called polymer dispersions are water-dispersed polymers which, depending on the glass transition temperature or chain length, are viscous liquids to solids.
  • emulsifiers are used. These are oligomeric or polymeric compounds having a hydrophilic and a lipophilic moiety.
  • lipophilic end will usually always be a long branched or unbranched alkyl chain, depending on whether the hydrophilic end contains a polyalkyl ether, a carboxylate function or an ammonium salt, one speaks of nonionic, anionogenic or cationogenic emulsifier systems.
  • an emulsifier is firmly anchored in the polymer via its lipophilic radical, so that the polymer receives hydrophilic groups and can be dispersed in water.
  • emulsifier systems can be modified such that the polymer itself already carries carboxylate or ammonium functions which can be reacted for dispersion in water with alkali metal, alkaline earth metal hydroxides or amines or with acids such as formic acid or acetic acid.
  • these emulsifier systems have various disadvantages.
  • nonionic emulsifiers larger amounts are usually required so that the coating becomes sensitive to moisture.
  • nonionic emulsifiers diffuse to the surface, causing them becomes greasy and the intercoat adhesion deteriorates. If alkali metal or alkaline earth metal hydroxides are used, anionogenic emulsifiers also provide moisture-sensitive coatings.
  • amines When amines are used in anionogenic systems, their volatilization achieves higher water resistance, but amines are released into the environment. Similarly, it is the case of cationogenic systems that usually a volatile acid such as. B. release acetic acid or formic acid.
  • the products offered on the market are very diverse and include, for example, dispersions based on acrylates, styrene-acrylates, butadiene-styrene, vinylidene-styrene, polyurethane, vinyl acetates, vinyl acrylates, butadiene-acrylonitrile and ethene-vinyl acetates.
  • dispersion is used for which application is usually a question of the desired property picture and the costs. Areas of application can be found in the paper and graphic arts industry, the paints and coatings industry, the adhesives industry, the textile and carpet industry, the leather industry, the construction industry, the foam manufacturing industry and in medicine and pharmacy.
  • the acid solutions contain volatile acids, eg. For example, formic acid, which volatilizes during drying and is released as a hazardous substance.
  • Alkaline or basic systems in turn hydrolyze and condense faster than acidic systems, so that oligomers are formed by this partial condensation. After the application, they can no longer crosslink to the required extent due to already used crosslinking groups and relatively soft films are formed. (EP 0 716 127, EP 0 716 128, EP 0 832 911, EP 1 101 787, WO 06/010666, WO 05/014741)
  • the object was to develop a polymer dispersion based on silanes, which, on the one hand, is hydrolyzed on the other hand, but prevents oligomer formation by virtue of its low basicity. When the polymer dispersions dry, again no volatile acids should be released into the environment.
  • this object could surprisingly be achieved in that an aminoalkoxysilane whose amino groups was reacted with a double bond-containing organic acid, wherein a corresponding ammonium salt is generally formed, is dispersed in water.
  • hydrolysis can take place, but on the other hand, the condensation to oligomers but are largely prevented.
  • the double bonds containing organic acid can be crosslinked easily and thus can remain as a polymer in the formed silane film.
  • the silane film is surprisingly hard and scratch-resistant.
  • the process according to the invention offers the advantage that the pH of the reaction solution can be tailor-made to a range from 4 to 7 and no acids are liberated.
  • A represents a substituted or unsubstituted aminoalkyl group, a substituted or unsubstituted diaminodialkyl group or substituted or unsubstituted triaminothalkyl group.
  • aminosilanes or aminoalkylsilanes include, but are not limited to, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 2-aminoethyl-3-aminopropyltrimethoxysilane, amino-functional propyltrimethoxysilane, bis (3-trimethoxysilylpropyl) amine, bis (3-thethoxysilylpropyl) amine, N-benzyl-N- (2-aminoethyl) -3-aminopropylthmethoxysilane hydrochloride, N-
  • Preferred aminosilanes or aminoalkylsilanes are substituted or unsubstituted aminosilane compounds, in particular 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl) -3-aminopropyltrinnethoxysilane, 2-aminopropyl-3-aminopropyltrimethoxysilane, 2 -Aminopropyl-3-aminopropylthethoxysilane, 2-aminoethyl-2-aminoethyl-3-aminopropyltrinnethoxysilane, 2-aminoethyl-2-aminoethyl-3-aminopropylthethoxysilane and N- (n-butyl) -3-aminopropyltrimethoxysilane.
  • DYNASYLAN® ® AMMO DYNASYLAN® AMEO
  • DYNASYLAN® ® 1505 DYNASYLAN® ® 1189 DYNASYLAN® ® DAMO
  • DYNASYLAN® ® TRIAMO DYNASYLAN® ® AMMO
  • DYNASYLAN® AMEO DYNASYLAN® ® 1505 DYNASYLAN® ® 1189
  • DYNASYLAN® ® DAMO DYNASYLAN® TRIAMO.
  • the groups Y are identical or different, Y being OH, ONa, OK, OR ',
  • OCOR ' OSiR's, Cl, Br, I or NR' 2
  • one or more silanes of the general formula (II) are optionally, one or more silanes of the general formula (II).
  • the groups R are independently hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl groups and each have 1 to 18 carbon atoms and may optionally be substituted
  • the groups X are the same or different and X is an oxy, hydroxy, alkoxy, carboxy, silyl, alkylsilyl, alkoxysilyl, siloxy, alkylsiloxy, alkoxysiloxy, silylalkyl, alkoxysilylalkyl, alkylsilylalkyl, halogen , omega-haloalkyl, epoxy, omega-glycidyloxyalkyl, ester, fluoroalkyl or perfluoroalkyl, blocked isocyanate, cyanatoalkyl, isocyanatoalkyl, omega-methacryloxy-alkyl, acrylate, methacrylate, mercap
  • Thalkoxysilanes in particular alkyltrialkoxysilanes of the RSi (OR ') 3 type are preferably used here, 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), Isobutyltriethoxy- silane, Propylthmethoxysilan (DYNASYLAN ® PTMO), Propylthethoxysilan, ethyl trimethoxysilane, ethyltriethoxysilane, methyltrimethoxysilane (DYNASYLAN ® MTMS) or methyltriethoxysilane.
  • isobutyltrimethoxysilane DYNASYLAN ® IBTMO
  • Isobutyltriethoxy- silane DYNASYLAN ® PTMO
  • Propylthethoxysilan ethyl trimethoxysilane
  • ethyltriethoxysilane methyltrimethoxysilane
  • Thalkoxysilane can with a substituent of the type X according to the formula XSi (OR ') 3, such as 3-chloropropyltrimethoxysilane, 3-glycidyloxypropyltrimethoxysilane (DYNASYLAN ® GLYMO), 3-mercaptopropyltrimethoxysilane (DYNASYLAN ® MTMO), 3-Methacryloxypropylthmethoxysilan (DYNASYLAN ® MEMO) are used.
  • DYNASYLAN ® VTMO or vinyltriethoxysilane used such as vinyltrimethoxysilane Alkenylthalkoxysilane.
  • halosilanes preferably trichlorosilanes
  • alkoxysilanes in the process according to the invention.
  • the hydrochloric acid formed during the hydrolysis must be removed.
  • the aminosilane or aminoalkylsilane used according to formula I is advantageously partially or completely neutralized with an acid containing carbon double bonds.
  • an acid containing carbon double bonds may be mono- or poly-protic acids.
  • acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, oleic acid and the derivatives of the abovementioned acids are preferably used in the process according to the invention.
  • the molar ratio of aminosilanes or aminoalkylsilanes to the acid is preferably to be selected so that per primary, secondary or tertiary amino group of 0.2 to 2.0 molar equivalents of a monoprotic acid are available.
  • the preparation can be done for example by dropwise addition of the appropriate amount of acid to the silane mixture with cooling, this variant is particularly suitable when equivalent amounts of acid and amine are used.
  • This can be done both in a solvent and run without the use of a solvent.
  • alcohols such as example, ethanol and methanol, advantageous.
  • concentrations of the solutions are from 0.1 to 99.9% by weight, preferably from 20 to 90% by weight, in particular from 30 to 80% by weight.
  • the reaction can also be carried out in any other organic solvent, provided that the reaction components dissolve here.
  • Such a mixture may be stored as an intermediate for an extended period if necessary.
  • the adduct of the silanes A n SiY n according to formula I and (R) a (X) bSiY n according to formula II and the acid used according to the invention is dissolved either in 100% concentration or in an organic solvent at temperatures above 20 0 C and below 80 0 C, preferably stirred at temperatures between 30 0 C and 70 0 C, in particular at temperatures between 35 0 C and 45 0 C in water, wherein the ratio of silanes used according to the invention and acid is to be selected in that, after stirring in, the reaction solution has a pH of from 2 to 9, preferably a pH of from 3 to 8, particularly preferably a pH of from 4 to 7.5.
  • the resulting in the hydrolysis alcohols such as methanol or ethanol and optionally with solvent used are then at temperatures above 20 0 C and below 80 0 C, preferably at temperatures between 30 0 C and 70 0 C, in particular at temperatures between 35 0 C and Distilled off 45 0 C, wherein in the latter cases with a vacuum pump, the pressure is to be lowered. If during this distillation of the alcohol and the optionally used solvent water is discharged with, the amount of water can be replaced later.
  • the aqueous solutions After dilution with water, the aqueous solutions then have a content of acid-neutralized silane of ⁇ 50% by weight, preferably from 5 to 40% by weight, in particular from 10 to 30% by weight.
  • the present method may be practiced be that a pH of the reaction solution of about 3 to 4.5 results.
  • the silanol groups formed during the hydrolysis are partially retained, since the further condensation is hindered at this pH.
  • a condensation or crosslinking especially at a pH change, z.
  • After application when the system is applied to a basic surface such as concrete or metals.
  • the condensation or cross-linking also occurs when the water has volatilized.
  • the second method step is advantageously carried out on site and immediately before the application itself.
  • the adduct of the silanes A n SiY n according to formula I and (R) a (X) b SiY n according to formula II and the acid used in the invention either in 100% concentration or in solution Place at a temperature above 0 0 C, preferably at a temperature above 10 0 C, in particular at a temperature between 20 0 C and 40 0 C is stirred into water.
  • a transport cost savings for example, the advantage of a transport cost savings.
  • a particularly preferred method is based on a one-step process.
  • the organic acid is placed in water and the silane or silane mixture is stirred in the course of 0.1 to 10 hours. Conveniently, then just enough acid is initially charged that the silanol groups are partially retained or, after addition of the silane or silane mixture, a pH of from 3 to 8, preferably from 7 to 7.5 results.
  • the addition of the acid - distributed over the entire reaction time - can be done in up to 100 individual portions.
  • this method offers the advantage of a particularly simple method of assembly, on the other hand can between already during the addition of the silane mixture produced by hydrolysis of alcohols such as methanol or ethanol at temperatures above 20 0 C and below 80 0 C, preferably at temperatures 30 0 C and 70 0 C, in particular at temperatures between 35 0 C and 45 0 C are distilled off, in the latter cases with a vacuum pump, the pressure is to be lowered. During the azeotropic distillation of the alcohol, the amount of water entrained must be replaced.
  • alcohols such as methanol or ethanol
  • the aqueous solutions have a content of acid-neutralized silane of ⁇ 50% by weight, preferably from 5 to 40% by weight, in particular from 10 to 30% by weight.
  • the reaction of the silanes and modified amino silanes and aminoalkyl silanes in accordance with this one-step process in water is preferably at a temperature from 0 to 200 0 C, preferably at a temperature of 10 to 100 0 C, particularly preferably at a temperature of 20 to 90 0 C. carried out. Most preferably, this reaction of the silanes is carried out at a temperature of 60 ⁇ 15 0 C. In a particular embodiment of the process according to the invention, the temperature is not kept constant over the entire reaction time. Thus, for example, it is advantageous to raise the reaction temperature slightly towards the end of the reaction time in order to distill off the solvent which may be present and the alcohols formed during the hydrolysis, such as methanol, ethanol or a mixture of these alcohols, as mentioned.
  • the process according to the invention for the conversion of aminosilanes and silanes advantageously leads to silanols and siloxanes and / or to siloxanes with ammonium groups which have as counterion an acrylate, methacrylate, maleate, fumarate, oleate, itacon, aconitic acid anion or a derivative of the abovementioned Contain acids.
  • aqueous solutions are prepared in concentrations of less than 50 wt .-%, preferably from 5 to 40 wt .-%, in particular from 10 to 30 wt .-%.
  • the process according to the invention can be carried out continuously or in batch mode.
  • an electron beam crosslinking can (for example, at a temperature of 100 0 C; radiation dose of 3 Mrad; electron gun.: Elektrocurtain, Fa. Energy Sciences Int.) Or regulators and initiators can be used.
  • Regulators are added to the dispersion for adjusting the molecular weights, wherein, based on the amount of acid, preferably from 0.05 to 5 wt .-%, preferably from 0.1 to 2 wt .-% and particularly preferably from 0.2 to 1 wt. -% be used.
  • the coating composition according to the invention has a molecular weight regulator selected from mercaptans, such as, for example, n-butyl mercaptan, n-dodecyl mercaptan, 2-mercaptoethanol, or 2-ethylhexyl thioglycolate.
  • the coating composition according to the invention preferably has n-dodecylmercaptan.
  • the coating composition according to the invention may contain what are known as polymerization initiators.
  • the coating composition according to the invention from 0.01 to 2 wt .-% based on the amount of acid.
  • the dispersion of the invention preferably azo compounds such as 2,2'-azobis (isobutyronitrile), 2,2 'azobis- (isobutterklareamidin) - dihydrochloride or 2,2'-azobis (2,4-dimethylvaleronitrile), redox Systems, such as the combination of tertiary amines with peroxides on.
  • the dispersion according to the invention preferably comprises peroxides, more preferably peroxodisulfate, dilauroyl peroxide, tert-butyl peroctoate, tert-butyl phesononanoate, dicyclohexyl peroxydicarbonate, dibenzoyl peroxide or 2,2-bis (tert-butylperoxy) butane.
  • the dispersion according to the invention can also be a mixture of different polymers. tion initiators with different half-life, such as dilauroyl peroxide and 2,2-bis (tert-butylperoxy) butane, to keep constant the radical during the polymerization and at different polymerization temperatures.
  • the dispersion according to photoinitiators include, in particular, these are ⁇ -hydroxy ketones, phenylglyoxylates, benzyl dimethyl or ⁇ -aminoketones.
  • acrylate and methacrylate compounds can be admixed to the system according to the invention, such as, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, hexyl (meth) acrylate, Heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth)
  • so-called molecular weight regulators for example from the class of known mercaptans, can be added to adjust the molecular weights, such as n-butylmercaptan, n-dodecylmercaptan, 2-mercaptoethanol or 2-ethylhexylthioglycolate, the molecular weight regulators generally being used in amounts of 0 , 05 to 5 wt .-%, based on the monomer mixture, preferably in amounts of 0.1 to 2 wt .-% and particularly preferably in amounts of 0.2 to 1 wt .-% are used on the monomer mixture. Preference is given to using n-dodecylmercaptan as molecular weight regulator.
  • the mixing ratio of the inventive silane-based system to optionally added acrylate or methacrylate compounds is 0.1 to 99.1 wt .-% to 99.9 to 0.1 wt .-%. It is preferably 30 to 70% by weight to 70 to 30% by weight. In particular, at most 15% by weight of the acrylate or methacrylate compounds are added to the aqueous system.
  • additives such as heat and light stabilizers, in particular UV absorbers, optical brighteners, antistatic agents, lubricants, antiblocking agents, nucleating agents, fillers and dyes, pigments and flame retardants may be included in the inventive system.
  • these additives Based on the solids content of the dispersion, these additives have a total of preferably from 0.01 wt .-% to 5.0 wt .-%.
  • wetting and leveling agents in amounts of 0.01 wt .-% to 5.0 wt .-% may be advisable for certain surfaces.
  • composition of the invention can be used in many ways such.
  • the coating of fillers for the water-repellent coating of salts, in particular the coating of perborates, for coating tacky plastic granules, for the coating of concrete and glass, for the synthesis of catalysts and their starting compounds, for stabilizers and for the synthesis or modification of ceramic compositions and polymers and for the coating of polymer granules, polymer plates, polymer fibers and polymer semifinished products.
  • Sheet metal test specimen (Chemetall No. 129611 with bonder rust protection 26 / NL 60).
  • the solution / dispersion from Example 4 is applied to this test specimen - the uncoated specimen representing the blank specimen (Test specimen 6.1) or from Example 5 (test specimen 6.2) in a layer thickness of 200 microns aufgerakelt (laboratory blade).
  • the film is allowed to dry at room temperature. This is followed by storage for 24 hours at 50 0 C in a vacuum oven. Thereafter, an annealing of 1 hour in a drying oven at 100 0 C and then cooling in the course of 24 hours to room temperature.
  • the coating and treatment are carried out analogously with the same solution / dispersion
  • Example 6 However, only half of the area is coated, the uncoated area serves as a blank.
  • the two test specimens carry the
  • Example 6 The samples of Example 6 are stored in vertical position 6 months (March to August period) under outdoor weather (Central European climate) and then assessed visually, the grade 1 is a very good and grade 5 is a very poor rating.
  • Coated specimens no. 2 and no. 3 have a water-resistant, transparent and hard film which does not change in outdoor weathering. The drying of the solution / dispersion proceeds without any solvent, amine or acid emission.
  • the scratch resistance of the samples of Example 7 is checked so that after removal of the test specimens from the oven and cooling in the course of 24 hours commercially available steel wool (amount about 1 cm 3 ) by hand under low load (about 100 pond) each 10 times in forward and backward on the entire substrate was moved. This means that scrubbing is done with equal intensity over both the coated and uncoated surfaces. It is then visually assessed which of the two polyamide surfaces (ie, uncoated-coated) has more scratch marks, with grade 1 being a very good rating and grade 5 being a very poor rating.
  • Coated specimens no. 5 and no. 6 are significantly more scratch resistant than the blank specimen.

Abstract

L'invention a pour objet la préparation d'une composition à base de silanes destiné au revêtement inrayable, hydrophobe et aqueux de métaux, matières plastiques, produits chimiques, pâtes céramiques, béton et verre.
EP08785901A 2007-08-17 2008-07-02 Système de revêtement aqueux à base de silanes, sa préparation et son utilisation Withdrawn EP2178984A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102007039061 2007-08-17
DE102007060334A DE102007060334A1 (de) 2007-08-17 2007-12-14 Silane-basierendes und wässriges Beschichtungssystem, dessen Herstellung und Verwendung
PCT/EP2008/058492 WO2009024386A1 (fr) 2007-08-17 2008-07-02 Système de revêtement aqueux à base de silanes, sa préparation et son utilisation

Publications (1)

Publication Number Publication Date
EP2178984A1 true EP2178984A1 (fr) 2010-04-28

Family

ID=40279591

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08785901A Withdrawn EP2178984A1 (fr) 2007-08-17 2008-07-02 Système de revêtement aqueux à base de silanes, sa préparation et son utilisation

Country Status (6)

Country Link
US (1) US8349911B2 (fr)
EP (1) EP2178984A1 (fr)
JP (1) JP2010536966A (fr)
CN (1) CN101367943B (fr)
DE (1) DE102007060334A1 (fr)
WO (1) WO2009024386A1 (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101176153A (zh) * 2005-05-17 2008-05-07 松下电器产业株式会社 多层信息记录介质及其制造方法
DE102009017822A1 (de) * 2009-04-20 2010-10-21 Evonik Degussa Gmbh Wässrige Silansysteme basierend auf Tris(alkoxysilylalkyl)aminen und deren Verwendung
US8763700B2 (en) 2011-09-02 2014-07-01 Robert Ray McDaniel Dual function proppants
US9290690B2 (en) 2011-05-03 2016-03-22 Preferred Technology, Llc Coated and cured proppants
US9725645B2 (en) 2011-05-03 2017-08-08 Preferred Technology, Llc Proppant with composite coating
US9562187B2 (en) 2012-01-23 2017-02-07 Preferred Technology, Llc Manufacture of polymer coated proppants
US9518214B2 (en) 2013-03-15 2016-12-13 Preferred Technology, Llc Proppant with polyurea-type coating
US10100247B2 (en) 2013-05-17 2018-10-16 Preferred Technology, Llc Proppant with enhanced interparticle bonding
US9790422B2 (en) 2014-04-30 2017-10-17 Preferred Technology, Llc Proppant mixtures
US10980236B2 (en) 2014-11-04 2021-04-20 Allied Bioscience, Inc. Broad spectrum antimicrobial coatings comprising combinations of organosilanes
KR102503389B1 (ko) * 2015-03-24 2023-02-24 세메다인 가부시키 가이샤 경화성 조성물
WO2016183313A1 (fr) 2015-05-13 2016-11-17 Preferred Technology, Llc Agents de soutènement à haute performance
US9862881B2 (en) 2015-05-13 2018-01-09 Preferred Technology, Llc Hydrophobic coating of particulates for enhanced well productivity
EP3337859B1 (fr) * 2015-08-19 2023-06-07 The Regents of the University of California Revêtements repoussant les liquides
CN105646565B (zh) * 2016-03-24 2019-01-29 山东大学 一种含腈基硅氧烷的合成及室温缩合型腈硅橡胶的制备方法
CN109071821B (zh) * 2016-04-28 2021-05-04 住友化学株式会社 化合物及含有化合物的组合物
PL3243858T3 (pl) 2016-05-11 2019-09-30 Basf Se Sieciowane polimery, sposoby ich wytwarzania i zastosowanie
US11592246B2 (en) 2016-09-19 2023-02-28 Nelumbo Inc. Nanostructure coating materials and methods of use thereof
US11208591B2 (en) 2016-11-16 2021-12-28 Preferred Technology, Llc Hydrophobic coating of particulates for enhanced well productivity
US10696896B2 (en) 2016-11-28 2020-06-30 Prefferred Technology, Llc Durable coatings and uses thereof
US10392408B2 (en) 2017-06-27 2019-08-27 Avmor Ltd Siloxane oligomers for the treatment of solid surfaces
EP3708569A1 (fr) * 2019-03-11 2020-09-16 Evonik Operations GmbH Siloxanyle fonctionnel n-vinyl-benzyl-amino-alkyle sans cov, aqueux et stable au stockage et son procédé de production
CA3153095A1 (fr) * 2019-10-03 2021-04-08 Gavri GROSSMAN Revetements antimicrobiens a large spectre comprenant des combinaisons d'organosilanes

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1387721A (fr) * 1963-05-10 1900-01-01
US3890269A (en) * 1972-08-11 1975-06-17 Stauffer Chemical Co Process for preparing aminofunctional polysiloxane polymers
US4690959A (en) 1986-05-09 1987-09-01 Dow Corning Corporation Polyethylene composite comprising a coupling agent composition comprising fumaric acid and an aminosilane
US4939035A (en) * 1988-09-06 1990-07-03 Hoechst Celanese Corporation Extrusion coatable polyester film having an aminofunctional silane primer, and extrusion coated laminates thereof
US5215822A (en) * 1991-03-01 1993-06-01 Energy Sciences, Inc. Method of imbuing organic polymer films with improved gas impermeability characteristics and improved barrier coatings therefor
US5178675A (en) 1991-03-22 1993-01-12 Lord Corporation Alkoxy silane adhesive compositions
DE69429335T2 (de) 1994-03-31 2002-08-22 Sivento Inc Verfahren zur Herstellung stabiler wässriger Silan-Zusammensetzungen
DE4416857C1 (de) * 1994-05-13 1995-06-29 Fraunhofer Ges Forschung Hydrolysierbare und polymerisierbare Silane, Verfahren zu deren Herstellung sowie deren Verwendung
WO1996004339A1 (fr) 1994-08-02 1996-02-15 Lord Corporation Compositions adhesives aqueuses a base de silane
DE4443824A1 (de) 1994-12-09 1996-06-13 Huels Chemische Werke Ag Organopolysiloxan-haltige Zusammensetzungen auf Wasserbasis, Verfahren zu deren Herstellung sowie deren Verwendung
DE4443825A1 (de) 1994-12-09 1996-06-13 Huels Chemische Werke Ag Wasserbasierende Organopolysiloxan-haltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung
DE19624032A1 (de) 1996-06-17 1997-12-18 Huels Chemische Werke Ag Oligomerengemisch kondensierter Alkylalkoxysilane
DE19639782A1 (de) 1996-09-27 1998-04-02 Huels Chemische Werke Ag Glycidether-, Acryl- und/oder Methacryl-funktionelle Organopolysiloxan-haltige Zusammensetzungen auf Wasser-Basis, Verfahren zu deren Herstellung sowie deren Verwendung
DE19649955A1 (de) 1996-12-03 1998-06-04 Huels Chemische Werke Ag Fluoralkyl-funktionelle Organopolysiloxan-haltige Zusammensetzungen auf Wasser/Alkohol-Basis, Verfahren zu deren Herstellung sowie deren Verwendung
US6713186B1 (en) 1996-12-03 2004-03-30 Degussa Ag Fluoroalkyl-functional organosiloxane-containing compositions based on alcohol, a process for their preparation and their use
DE19649954A1 (de) 1996-12-03 1998-06-04 Huels Chemische Werke Ag Fluoralkyl-funktionelle Organosiloxan-haltige Zusammensetzungen auf Alkoholbasis, Verfahren zu deren Herstellung sowie deren Verwendung
DE19649953A1 (de) 1996-12-03 1998-06-04 Huels Chemische Werke Ag Fluoralkyl-funktionelle Organopolysiloxan-haltige Zusammensetzungen auf Wasserbasis, Verfahren zu deren Herstellung sowie deren Verwendung
DE19818923A1 (de) 1998-04-28 1999-11-04 Degussa Stabile Zusammensetzungen wasserlöslicher, Amino- und Alkenyl-funktioneller Organosiloxane, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19823390A1 (de) 1998-05-26 1999-12-16 Degussa Oligomerisiertes Organopolysiloxan-Cokondensat, dessen Herstellung und dessen Verwendung
DE19834990B4 (de) 1998-08-03 2005-09-15 Degussa Ag Acryloxypropyl- oder Methacryloxypropyl-Gruppen enthaltende Siloxan-Oligomere, Verfahren zu ihrer Herstellung sowie deren Verwendung
DE19904132C2 (de) 1999-02-03 2002-11-28 Degussa Zusammensetzung fluororganofunktioneller Silane und Siloxane, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19908636A1 (de) 1999-02-27 2000-08-31 Degussa Wasserbasierende Zusammensetzung aminofunktioneller Siliciumverbindungen
DE19964309C2 (de) 1999-11-15 2003-07-03 Degussa Triamino- und fluoralkylfunktionelle Organosiloxane oder deren Gemische
WO2001066656A2 (fr) * 2000-03-03 2001-09-13 Dow Corning Corporation Revetements isolants a base de bis-silanes, d'acrylates multifonctionnels et d'acides ethyleniquement insatures
DE10049153A1 (de) 2000-09-27 2002-04-11 Degussa Farbe, Lack, Schadstoffe, Bioorganismen, Öl, Wasser, und/oder Schmutz abweisende Beschichtung
DE10335178A1 (de) 2003-07-30 2005-03-31 Degussa Ag Zusammensetzung eines Gemisches aminoalkyl- und oligo-silylierter-aminoalkyl-funktioneller Siliciumverbindungen, deren Herstellung und deren Verwendung
DE10336544A1 (de) 2003-08-05 2005-02-24 Degussa Ag Zweikomponentenbeschichtungssystem für die Ausstattung glatter Oberflächen mit "Easy-to-clean" - Eigenschaften
DE102004037043A1 (de) 2004-07-29 2006-03-23 Degussa Ag Blockkondensate organofunktioneller Siloxane, deren Herstellung, Verwendung sowie deren Eigenschaften
DE102004049427A1 (de) 2004-10-08 2006-04-13 Degussa Ag Polyetherfunktionelle Siloxane, polyethersiloxanhaltige Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung
DE102005060402A1 (de) 2005-12-15 2007-06-21 Degussa Gmbh Lagerstabile Beschichtungszusammensetzung für eine abriebfeste und witterungsbeständige Ausstattung glatter anorganischer Oberflächen mit "Easy-to-clean"Eigenschaften
DE102005060401A1 (de) 2005-12-15 2007-06-21 Degussa Gmbh Lagerstabile Beschichtungszusammensetzung für eine abriebfeste und witterungsbeständige Ausstattung glatter anorganischer Oberflächen mit "Easy-to-clean"-Eigenschaften

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009024386A1 *

Also Published As

Publication number Publication date
DE102007060334A1 (de) 2009-02-19
US20110039972A1 (en) 2011-02-17
CN101367943B (zh) 2013-05-29
JP2010536966A (ja) 2010-12-02
WO2009024386A1 (fr) 2009-02-26
CN101367943A (zh) 2009-02-18
US8349911B2 (en) 2013-01-08

Similar Documents

Publication Publication Date Title
EP2178984A1 (fr) Système de revêtement aqueux à base de silanes, sa préparation et son utilisation
DE69632196T2 (de) Wässerige härtbare silan/polymer-zusammensetzungen
EP2385076B1 (fr) Procédé de fabrication d'un matériau de revêtement
DE60110212T2 (de) Bei raumtemperatur härtende beschichtungszusammensetzungen
EP1745107A2 (fr) Composition contenant des particules a fonction alcoxysilyle, reticulable sous l'effet de l'humidite
EP1544232A1 (fr) Polysiloxanes ayant des groupes ester (méth)acrylique liés par SiOC, procédé pour leur préparation et leur application comme couche antiadhérente, durcissable par irradiation.
EP2059571A1 (fr) Enduits et peintures, dispersions de copolymères et leur utilisation
DE4443824A1 (de) Organopolysiloxan-haltige Zusammensetzungen auf Wasserbasis, Verfahren zu deren Herstellung sowie deren Verwendung
EP0143877A1 (fr) Emulsions stables d'organopolysiloxanes
WO2008017674A1 (fr) Copolymères réactifs réticulables d'organosilicones ainsi que procédé pour leur préparation et leur utilisation
DE4331608A1 (de) Mit Acrylatgruppen modifizierte Organopolysiloxane
DE2837074A1 (de) Haertbares vinylpolymerisat mit sinylgruppe und verfahren zu seiner herstellung
EP2035473A1 (fr) Solutions à haute teneur en matières solides de copolymères d'organosilicones avec une haute teneur en silicone et une haute teneur en matières solides et procédés pour leur préparation et leur utilisation
WO2005092933A1 (fr) Composition durcissable contenant des particules modifiees en surface
DE10245725A1 (de) Schichtsystem und Verfahren zu dessen Herstellung
DE102008000595A1 (de) Nachvernetzendes Wachs und Verfahren zu seiner Herstellung
WO2010112106A1 (fr) Agents de revêtement durcissant à l'humidité à base de solvants aprotiques contenant des liants comprenant des groupes alcoxysilane et leur utilisation
DE102010062054A1 (de) Wässriges Hybridbindemittel für Fugenmörtel
WO2013156187A1 (fr) Nouveaux systèmes de siloxane à fonction (meth)acrylamido, faciles à produire, réduits en composés organiques volatils (voc), biodégradables, et leur procédé de production et leur utilisation
WO2006087079A1 (fr) Compositions durcissables par reaction d'addition de michael
DE69632306T2 (de) Härtbare wässrige silylpolymerzusammensetzungen
EP2838904A1 (fr) Procédé de production de silanes à fonction (méth)acrylamido par la mise en réaction de aminoalkyl-alkoxysilanes avec de l'anhydride d'acide acrylique
EP1896521A1 (fr) Resines de silicone ayant une reactivite definie
DE102004014686A1 (de) Oberflächenmodifizierte Partikel enthaltende härtbare Zusammensetzung
DE102006014137A1 (de) Beschichtungszusammensetzung auf Basis aminofunktionalisierter Siloxane

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: 20100111

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 MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

17Q First examination report despatched

Effective date: 20100610

DAX Request for extension of the european patent (deleted)
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: 20150414