EP2590759A1 - Procédé de préparation d'une dispersion contenant des particules de dioxyde de silicium et des agents de cationisation - Google Patents
Procédé de préparation d'une dispersion contenant des particules de dioxyde de silicium et des agents de cationisationInfo
- Publication number
- EP2590759A1 EP2590759A1 EP11721515.2A EP11721515A EP2590759A1 EP 2590759 A1 EP2590759 A1 EP 2590759A1 EP 11721515 A EP11721515 A EP 11721515A EP 2590759 A1 EP2590759 A1 EP 2590759A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dispersion
- weight
- bet surface
- water
- silicon dioxide
- 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- Withdrawn
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5218—Macromolecular coatings characterised by inorganic additives, e.g. pigments, clays
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/14—Colloidal silica, e.g. dispersions, gels, sols
- C01B33/141—Preparation of hydrosols or aqueous dispersions
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/36—Coatings with pigments
- D21H19/38—Coatings with pigments characterised by the pigments
- D21H19/40—Coatings with pigments characterised by the pigments siliceous, e.g. clays
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
- B41M5/42—Intermediate, backcoat, or covering layers
- B41M5/426—Intermediate, backcoat, or covering layers characterised by inorganic compounds, e.g. metals, metal salts, metal complexes
Definitions
- the invention relates to a process for the preparation of a dispersion comprising silicon dioxide particles and cationizing agents, to the dispersion itself and to a coating paint obtainable therewith.
- EP-A-1331254 added cationic polymers. Especially with highly filled dispersions, the better because the recipes of the resulting polymers.
- EP-A-1413451 discloses a process for producing a media sheet for ink-jet printing applications in which porous, inorganic macroparticles and an organosilane reagent are reacted on a substrate.
- the inorganic macroparticles may be silica particles.
- the organosilane reagent is an oligomer of the structure
- Another object was to provide an improved high solids coating paint from this dispersion.
- the invention relates to a process for the preparation of a
- silica particles having a BET surface area of 30 to 500 m 2 / g
- the cationizing agent is obtainable by reacting at least one haloalkyl-functional alkoxysilane, its hydrolysis products or condensation products and / or a mixture of the abovementioned substances with at least one aminoalcohol and a defined amount of water and optionally optionally at least partially removing the hydrolysis alcohol formed from the reaction mixture, the haloalkyl-functional alkoxysilane the general formula I
- R 1 are identical or different and R 1 is a hydrogen, a linear, branched or cyclic alkyl group having 1 to 8 C atoms, an aryl, arylalkyl or acyl group
- R 2 are the same or different and R 2 is a linear, branched or cyclic alkyl group having 1 to 8 C atoms or an aryl, arylalkyl or acyl group
- R 3 are the same or different and R 3 is a linear, branched or cyclic alkylene group having 1 to 18 C atoms,
- n 0 or 1 and Hal is chlorine or bromine
- x is 0, 1 or 2
- y is 0, 1 or 2
- (x + y) is 0, 1 or 2
- Groups R 4 are the same or different and R 4 is a group
- m is an integer between 1 and 16 and z is 1 or 2 or 3.
- the haloalkyl-functional alkoxysilane, its hydrolysis products or condensation products and / or a mixture of the abovementioned substances is to be referred to as component A and the aminoalcohol as component B.
- IR 1 is alkyl having 1 to 4 C atoms, acyl, and R 3 is a linear alkylene group having 1, 2, 3, 4, 5, 6, 7 carbon atoms, preferably having 2 C atoms.
- Preferred usable haloalkyl-functional alkoxysilanes are alkyl having 1 to 4 C atoms, acyl, and R 3 is a linear alkylene group having 1, 2, 3, 4, 5, 6, 7 carbon atoms, preferably having 2 C atoms.
- Chloroethyltriethoxysilane chloroethylmethyldimethoxysilane
- Chloroethylmethyldiethoxysilane chloroethyldimethylmethoxysilane
- Chloroethyldimethylethoxysilane chloromethyltriethoxysilane
- Chloromethylmethyldiethoxysilane chloromethyldinnethylnethoxysilane
- components A and B with respect to the haloalkyl group of component A and the tertiary nitrogen of component B in a molar ratio of 2: 1 to 1: 100, in particular from 2: 1 to 1:10, preferably from 2: 1 to 1: 5, more preferably from about 1: 1 to about 1: 1, 5, wherein, if appropriate, initially setting a ratio of 1: 1 and subsequently each batch of about 0.2 of component B with respect to the present component A in 1 to 4 batches.
- a process procedure has proven particularly advantageous in which water is present in an amount of from 0.5 to 500 mol of water per mole
- Silicon atoms of component A is used, preferably in at least one of the hydrolysis steps 0.5 mol of water per mole of hydrolyzable alkoxy group on the silane, wherein total preferably in particular 0.5 to 25 moles of water, preferably 5 to 25 moles of water per mole Silicon atoms with respect to
- used component A more preferably 10 to 25 moles of water per mole of silicon atoms, in particular 12 to 25 moles of water per mole of silicon atoms are used.
- reaction is carried out in the presence of a solvent, in particular alcohol, preferably in the presence of the resulting alcohol in the hydrolysis of the alkoxysilanes, particularly preferably in the presence of ethanol, methanol,
- the added solvent is suitably removed during the removal of the hydrolysis alcohol formed during the reaction from the system.
- Hydrolysis alcohol is substantially completely removed, preferably by distillation, in particular already during the reaction. According to a particularly preferred procedure, for example, the amount of hydrolysis alcohol removed by distillation and water in the azeotropic mixture can be compensated for by additional addition of water.
- Volatile solvents such as an added solvent and / or the alcohol formed in the reaction by hydrolysis, ie groups which are optionally hydrolysable to volatile solvent, in particular hydrolysis alcohol, are removed to a content in the total composition of less than 12 wt.% To 0 wt. -%, preferably by distillation according to the skilled worker methods.
- a solvent is considered to be a composition if the content of solvents in the overall composition is less than 10 % By weight to 0% by weight, more preferably less than 5% by weight, very particularly preferably less than 2% by weight to 0.0001% by weight, in particular 1 to ⁇ 0.5% by weight, preferably 0.5 to ⁇ 0.1 wt .-% could be adjusted, wherein the removal of volatile solvent during the reaction and / or thereafter by distillation, in particular under reduced pressure in the range of 1 to 1000 mbar, preferably from 80 to 300 mbar, more preferably in the range of 80 to 180 mbar, can take place. Suitably, however, one can also lower the pressure in the course of the conversion of ambient pressure to a reduced pressure.
- the distillation can be carried out batchwise or else continuously by means of a distillation column, thin-film evaporator and further the
- Distilled water can be supplemented by re-addition of water. At the end of the distillation can be the desired
- Final concentration of the solution can be adjusted by adding more water.
- the reaction is preferably carried out at a pressure of 1 mbar to 100 bar, preferably by about 1 mbar to 1, 1 bar, preferably at ambient pressure (atmospheric pressure), and a temperature of 20 and 150 ° C, preferably between 40 to 120 ° C, more preferably between 60 to 100 ° C, in particular from 80 to 95 ° C from.
- condensation catalyst for example, an organic or inorganic acid such as formic acid, acetic acid, propionic acid,
- Citric acid hydrogen chloride, as gas, concentrated or aqueous
- Hydrochloric acid boric acid, nitric acid, sulfuric acid or phosphoric acid.
- an inorganic or organic acid can also be added at any time to adjust the pH of the composition or reaction mixture.
- metal oxides preferably
- silica in particular silica, fumed silica, precipitated silica, silicates, boric acid, titanium dioxide, alumina, alumina hydrate, ATH
- Al (OH) 3 aluminum trihydroxide, Al (OH) 3
- magnesium hydroxide (Mg (OH) 2 ) cerium oxide, yttrium oxide, calcium oxide, iron oxides, zirconium oxide, hafnium oxide, boron oxide, gallium oxide, indium oxide, tin oxide, germanium oxide and corresponding hydroxides and oxide hydrates and mixtures of at least two the aforementioned compounds with each other.
- Suitable volatile solvents or groups which can be hydrolyzed to volatile solvents are alcohols, such as methanol, ethanol, isopropanol, n-propanol, and alkoxy groups which hydrolyze to alcohols, acyloxy group-containing radicals, and acetic acid or formic acid derived by hydrolysis, or aryloxy groups which can form phenols and also glycols and partially etherified glycols, such as ethylene glycol, diethylene glycol or methoxyethanol, which are either added to the formulation or formed by hydrolysis of their silyl esters conceived.
- alcohols such as methanol, ethanol, isopropanol, n-propanol, and alkoxy groups which hydrolyze to alcohols, acyloxy group-containing radicals, and acetic acid or formic acid derived by hydrolysis
- aryloxy groups which can form phenols and also glycols and partially etherified glycols, such as ethylene glycol, diethylene glycol or me
- the invention further relates to a process for the preparation of a special silica particles and cationizing agent-containing dispersion, wherein
- silica particles having a BET surface area of 30 to 500 m 2 / g
- the cationizing agent comprises one or more quaternary
- R u and R v are each independently an alkyl group of 2 to 4 carbon atoms, m is 2 to 5 and n is 2 to 5.
- the condensation products of the quaternary, aminoalcohol-functional, organosilicon compounds can have linear, branched and / or cyclic structures or structural regions with M, D, T structures. According to 29 Si NMR spectroscopy these are, in addition to preferably 0.5 to 5%, particularly preferably 1 to 3%, monomeric structures, preferably 3 to 15%, particularly preferably 5 to 10%, M structures and preferably 35 to 60th %, more preferably 40 to 55%, of D structures.
- M-D, T structures can be found in Walter Noll, Chemie und Technologie der Silicones, 1968, Verlag Chemie GmbH, Weinheim, Chapter 1.
- the quaternary, aminoalcohol-functional, organosilicon compounds preferably have a number average molecular weight M n of 500 to 5000, particularly preferably 1000 to 2500 on.
- the proportion of quaternary, aminoalcohol-functional, organosilicon compounds in the aqueous solution is preferably 30 to 60 wt .-% and particularly preferably 40 to 50 wt .-%.
- the silica particles used are amorphous silica particles.
- the silica particles carry condensable groups on their surface, for example OH groups.
- the amorphous silica particles can be
- the silica particles are pyrogenically produced particles.
- pyrogenic is meant the hydrolysis or oxidation of silicon compounds in the gas phase in a flame generated, as a rule, by the reaction of hydrogen and oxygen. Firstly, highly dispersed, non-porous primary particles are formed, which grow together in the further course of the reaction to form aggregates and which can further assemble them into agglomerates.
- the BET surface area of the silica particles used can vary over a wide range, from 30 to 500 m 2 / g. However, it has been found that the use of pyrogenically prepared silicon dioxide particles having a BET surface area of 200 m 2 / g or more, in particular those having a BET surface area of 240 to 330 m 2 / g, leads to dispersions which have particularly good properties in the Inkjet area have.
- one or more basic substances can additionally be used.
- these may be amines and / or salts thereof.
- acids can be used. Suitable acids may be hydrochloric acid, C 1 -C 4 -carboxylic acids, C 1 -C 4 -hydroxycarboxylic acids or C 1 -C 4 -dicarboxylic acids.
- the acid is usually added in an amount such that a pH of the dispersion of 2 to 6, preferably 3 to 5, more preferably 3.5 to 4.5 results. It should be noted, however, that even without the addition of acid stable dispersions can be obtained.
- organic solvents, bactericides and / or fungicides can be used in the preparation of the dispersion. In general, in the preparation of the dispersion, the procedure is that initially under low energy input, for example by means of a
- Dissolvers a predispersion prepared by adding silica particles to the liquid components of the dispersion.
- the actual dispersion takes place, in which the energy input is higher than in the first step.
- Suitable Dispregieraggregate are known in the art.
- An example is a rotor-stator unit called.
- Another object of the invention is a dispersion obtainable by the process according to the invention.
- This has an average particle diameter, determined by means of dynamic light scattering, of preferably 120 to 250 nm, particularly preferably 130 to 180 nm.
- the dispersion according to the invention contains 35 to 40% by weight of pyrogenically prepared silicon dioxide particles having a BET surface area of 250 m 2 / g to 350 m 2 / g and the average particle diameter determined by dynamic light scattering is 130 to 180 nm ,
- Another object of the invention is a coating color which contains the dispersion according to the invention and at least one binder.
- binders which can be used are: polyvinyl alcohol, partially or completely saponified, and cationized polyvinyl alcohol having a primary, secondary or tertiary amino group or a tertiary one
- Ammonium group on the main chain or on the side chain is N-(Ammonium group on the main chain or on the side chain.
- Polyvinylpyrrolidones polyvinyl acetates, silanized polyvinyl alcohols, styrene-acrylate latices, styrene-butadiene latices, melamine resins, ethylene-vinyl acetate copolymers, polyurethane resins, synthetic resins such as polymethyl methacrylates, polyester resins (eg unsaturated polyester resins), polyacrylates , modified starch, casein, gelatin and / or cellulose derivatives (eg
- the coating color may also contain one or more other pigments such as calcium carbonates, layered silicates, aluminum silicates, plastic pigments (eg polystyrene, polyethylene, polypropylene), silica gels, aluminum compounds (eg aluminum sols, colloidal aluminas and their hydroxy compounds such as pseudoboehmites, boehmites, aluminum hydroxides). .
- pigments such as calcium carbonates, layered silicates, aluminum silicates, plastic pigments (eg polystyrene, polyethylene, polypropylene), silica gels, aluminum compounds (eg aluminum sols, colloidal aluminas and their hydroxy compounds such as pseudoboehmites, boehmites, aluminum hydroxides).
- the coating color may have a content of mixed oxide particles between 10 and 60 wt .-%. It may preferably be greater than 15% by weight, more preferably it may be greater than 25% by weight.
- Coating may serve crosslinkers such as zirconium oxides, boric acid,
- auxiliaries such as optical brighteners, defoamers,
- wetting agents pH buffers, UV absorbers and viscosity aids are used.
- the coating composition according to the invention preferably has a solids content of from 10 to 30% by weight and more preferably from 15 to 30% by weight. Another object of the invention is the use of the
- Dispersion according to the invention and coating color for coating ink-receiving inkjet media are Dispersion according to the invention and coating color for coating ink-receiving inkjet media.
- a further subject of the invention is an ink-receiving medium comprising an ink-receiving layer, wherein the ink-receiving layer comprises the coating color of the invention and a support.
- a support there can be used, for example, paper, coated paper, resin films such as a polyester resin including polyethylene terephthalate, polyethylene naphthalate
- Diacetate resin a triacetate resin, an acrylic resin, a polycarbonate resin, a Polyvinyl chloride, a polyimide resin, Celluphan, celluloid and a glass plate can be used.
- photo base papers i. Papers on which one or more layers of polyethylene film has been applied to the front and / or back.
- the ink-accepting medium of the present invention also includes media in which the ink-receiving layer consists of multiple coating layers of the same type or other layers.
- the coating color according to the invention can only be in one or more layers.
- further ink-absorptive coatings may be included.
- one or more polymeric layers e.g., polyethylene
- one or more polymeric layers may be applied to the substrate and / or the coating of the present invention to increase mechanical stability and / or gloss in the coating (e.g., photo base paper, lamination).
- the carriers can be transparent or opaque.
- the thickness of the carrier is not limited, preferably thicknesses between 50 and 250 ⁇ be used.
- the coating color can be applied to the support and dried.
- Coating paint can be used with all common application methods, such as roller application, blade coating, air brush, doctor blade (profiled, smooth, nip), cast-bar process, film press, size press, curtain-coating process and slot nozzle application (eg casting squeegee, slot-dye) and
- the coated substrate can with all conventional methods such as air or convection drying (eg hot air duct), contact or
- Conduction drying energy beam drying (e.g., infrared and
- Hydrolyzable chloride was titrated potentiographically with silver nitrate (for example, Metrohm, Type 682 silver rod as indicator electrode and Ag / AgCl reference electrode or other suitable reference electrode).
- silver nitrate for example, Metrohm, Type 682 silver rod as indicator electrode and Ag / AgCl reference electrode or other suitable reference electrode.
- Acidification with nitric acid is measured potentiographically with silver nitrate, as above.
- the analysis values for hydrolyzable chloride and total chloride are identical and thus a measure of the completeness of the reaction, since with total chloride the sum of salt-like chloride (amine hydrochloride) and covalently bonded chlorine (chloroalkyl function) and with hydrolyzable chloride exclusively salt-like or water-cleavable chloride
- Digestion solution bright and clear of any precipitated silica is clear.
- the digestion vessel is connected to the distillation apparatus and distilled over ammonia released ammonia (27%) in the template.
- V consumption of sulfuric acid in ml
- c concentration of sulfuric acid in mol / l
- z
- the determination of S1O2 is carried out after decomposition by means of sulfuric acid and Kjeldahl catalyst, by determining the weight of the precipitated S1O2.
- Example 1 Preparation of a cationizing agent
- Chloropropyltriethoxysilane (CPTEO) and N, N-Dimethylethanolamine A 41 four-necked flask is charged with 1283.0 g of CPTEO (5.328 mol) and 160.0 g of ethanol. At RT, 143.9g of deionized water (1.5mol H2O / mol of Si) are removed within 16min. dropwise. The bottom temperature rises to about 40 ° C.
- p-DADMAC 60g of p-DADMAC are added to 1350g of DI water.
- 320 g of AEROSIL ® 300 are by means of a dissolver at 1500 to 4000 rev / min for 40 min and then stirred further predispersed over a period of 5 min at 2000 U / min.
- a rotor-stator dispersion 15000 rev / min with cooling ( ⁇ 30 ° C) is dispersed for 30 minutes. Finally, the dispersion is filtered through a 500 ⁇ sieve.
- AEROSIL ® 300 To 1200 g of deionized water 425 g of AEROSIL ® 300 are by means of a dissolver at 1500 to 4000 rev / min for 30 min and then stirred predispersed over a period of five minutes at 2000 rev / min on. Subsequently, it is now dispersed with a rotor-stator disperser at 15,000 rpm with cooling ( ⁇ 30 ° C) for 10 min.
- 428 g of AEROSIL ® 300 are with a dissolver at 1500 to 5000 U / min in a mixture of 805 g of demineralized water and 47.4 g of the solution of Example 1 within 17 min and stirred for 10 minutes at 2000 rev / min
- the mixture is then dispersed with a rotor-stator disperser (Kinematica Polytron PT6100) over a period of 30 minutes at 10,000 rpm. Finally, the dispersion is filtered through a 500 ⁇ sieve.
- the physico-chemical data of the dispersions D1 -D3 can be found in Table 2.
- the dispersion examples D4-D6 show, regardless of the parameter of the particle diameter, which solids content is possible with the maximum cationizing additive. As expected, the dispersions have very high viscosities but are still liquid and processable.
- p-DADMAC 60g of p-DADMAC are added to 1 190 g of deionized water. Then, 320 g of AEROSIL ® 300 are stirred by means of a dissolver at 1500 to 4000 rev / min and then further predispersed over a period of five minutes at 2000 U / min. The following will now be with a rotor-stator disperser dispersed at 15,000 rpm with cooling ( ⁇ 30 ° C) for ten minutes. Finally, the dispersion is filtered through a 500 ⁇ sieve.
- the dispersion is filtered through a 500 ⁇ sieve.
- AEROSIL ® 300 557 g of AEROSIL ® 300 are stirred with a dissolver at 1500 to 5000 U / min in a mixture of 885 g of demineralized water and 58 g of the solution from Example 1 and 10 minutes further dispersed at 2000 U / min. It is then dispersed with a rotor-stator disperser (Kinematica Polytron PT6100) over a period of 30 minutes at 10,000 rpm. Finally, the dispersion is filtered through a 500 ⁇ sieve.
- dispersions of the invention are also prepared based on other AEROSIL® types.
- the AEROSIL ® powder is stirred with a dissolver at 1500 to 5000 U / min in a mixture of 885 g of DI water and the appropriate amount of cationizing agent from Example 1 and further dispersed at 2000 U / min for 10 minutes. It is then treated with a rotor-stator dispersing device (Kinematica Polytron PT6100) via a Period of 30 minutes at 10,000 rpm dispersed. Finally, the dispersion is filtered through a 500 ⁇ sieve. Starting materials and quantities, as well as physical-chemical data of the dispersions D7-D10 are shown in Table 4.
- the glyoxal-containing composition "Cartabond TSI" from Clariant is added, the amount corresponding to 4.8% by weight of the amount of the polyvinyl alcohol.
- the viscosity of the ink jet coating is measured after 24 h by means of a Brookfield viscometer.
- S2 and S3 are prepared analogously to S1, but using the respective dispersion D2 and D3.
- the solids contents and viscosities of the coating colors are shown in Table 5.
- the coating colors S1 to S3 are each profiled using a
- wet film thickness of the respective coating color is chosen so that a
- the coating is kept at 105 ° C for a period of 8 minutes
- the coated papers are printed on a Canon PIXMA iP6600D ink jet printer with the highest resolution. The rating of
- Solids content a) Weight% 23.0 30 39 Avg. Particle 0 b) nm 132 125 1 14
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Silicon Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102010031184A DE102010031184A1 (de) | 2010-07-09 | 2010-07-09 | Verfahren zur Herstellung einer Siliciumdioxidpartikel und Kationisierungsmittel aufweisenden Dispersion |
PCT/EP2011/058342 WO2012004044A1 (fr) | 2010-07-09 | 2011-05-23 | Procédé de préparation d'une dispersion contenant des particules de dioxyde de silicium et des agents de cationisation |
Publications (1)
Publication Number | Publication Date |
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EP2590759A1 true EP2590759A1 (fr) | 2013-05-15 |
Family
ID=44626593
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP11721515.2A Withdrawn EP2590759A1 (fr) | 2010-07-09 | 2011-05-23 | Procédé de préparation d'une dispersion contenant des particules de dioxyde de silicium et des agents de cationisation |
Country Status (7)
Country | Link |
---|---|
US (1) | US8980960B2 (fr) |
EP (1) | EP2590759A1 (fr) |
JP (1) | JP5762534B2 (fr) |
CN (1) | CN102958619B (fr) |
DE (1) | DE102010031184A1 (fr) |
TW (1) | TWI467076B (fr) |
WO (1) | WO2012004044A1 (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102010031184A1 (de) * | 2010-07-09 | 2012-01-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung einer Siliciumdioxidpartikel und Kationisierungsmittel aufweisenden Dispersion |
DE102013208034A1 (de) | 2012-05-23 | 2013-11-28 | Evonik Industries Ag | Verfahren zum chemisch-mechanischen Polieren mittels einer Siliciumdioxidpartikel und Kationisierungsmittel aufweisenden Dispersion |
DE102013007602A1 (de) * | 2013-05-03 | 2014-11-06 | Schattdecor Ag | Verfahren zur Herstellung einer bedruckbaren ein- oder mehrschichtigen Materialbahn sowie eine danach hergestellte Materialbahn und eine zugehörige Anlage zur Herstellung einer derartigen Materialbahn |
JP6335512B2 (ja) * | 2014-01-10 | 2018-05-30 | キヤノン株式会社 | 記録媒体 |
US10993441B2 (en) | 2014-11-04 | 2021-05-04 | Allied Bioscience, Inc. | Antimicrobial coatings comprising organosilane homopolymers |
US10980236B2 (en) | 2014-11-04 | 2021-04-20 | Allied Bioscience, Inc. | Broad spectrum antimicrobial coatings comprising combinations of organosilanes |
WO2016073634A1 (fr) | 2014-11-04 | 2016-05-12 | Daniel Moros | Composition et procédé pour former une surface autodécontaminante |
US10258046B2 (en) | 2014-11-04 | 2019-04-16 | Allied Bioscience, Inc. | Antimicrobial coatings comprising quaternary silanes |
EP3256531A1 (fr) | 2015-02-11 | 2017-12-20 | Allied Bioscience, Inc | Revêtement anti-microbien et procédé de formation de celui-ci |
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2010
- 2010-07-09 DE DE102010031184A patent/DE102010031184A1/de not_active Withdrawn
-
2011
- 2011-05-23 EP EP11721515.2A patent/EP2590759A1/fr not_active Withdrawn
- 2011-05-23 CN CN201180028960.3A patent/CN102958619B/zh active Active
- 2011-05-23 JP JP2013519000A patent/JP5762534B2/ja active Active
- 2011-05-23 WO PCT/EP2011/058342 patent/WO2012004044A1/fr active Application Filing
- 2011-05-23 US US13/642,862 patent/US8980960B2/en active Active
- 2011-07-06 TW TW100123844A patent/TWI467076B/zh not_active IP Right Cessation
Non-Patent Citations (1)
Title |
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See references of WO2012004044A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2012004044A1 (fr) | 2012-01-12 |
CN102958619B (zh) | 2014-04-02 |
TW201217608A (en) | 2012-05-01 |
US8980960B2 (en) | 2015-03-17 |
DE102010031184A1 (de) | 2012-01-12 |
TWI467076B (zh) | 2015-01-01 |
CN102958619A (zh) | 2013-03-06 |
JP5762534B2 (ja) | 2015-08-12 |
JP2013537568A (ja) | 2013-10-03 |
US20130040078A1 (en) | 2013-02-14 |
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