US20110319544A1 - Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group - Google Patents
Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group Download PDFInfo
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- US20110319544A1 US20110319544A1 US13/226,879 US201113226879A US2011319544A1 US 20110319544 A1 US20110319544 A1 US 20110319544A1 US 201113226879 A US201113226879 A US 201113226879A US 2011319544 A1 US2011319544 A1 US 2011319544A1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/02—Compounds of alkaline earth metals or magnesium
- C09C1/021—Calcium carbonates
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/10—Treatment with macromolecular organic compounds
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
- C01P2006/62—L* (lightness axis)
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
- C01P2006/64—Optical properties, e.g. expressed in CIELAB-values b* (yellow-blue axis)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
Definitions
- the present invention concerns the field of paints, where the said paints contain at least one mineral matter which is a calcium carbonate obtained by dry grinding.
- This grinding which leads to a reduction in the sizes of the individual particles of calcium carbonate by mechanical action, is assisted by grinding agents which can be classified into the following 3 categories.
- the first comprises the weak acids (formic, acetic, lactic, adipic as mentioned in document FR 2 863 914, or stearic as indicated in document EP 0 510 890), and their salts (sodium lignin sulfonate, sodium acetate, etc.).
- the second includes the weak bases, and notably the amines (see document GB 2 179 268).
- the third and the most commonly used, since it is the most effective, includes the glycol-based alcohols, including notably diethylene glycol illustrated in documents WO 2002/081 573 and U.S. 2003/019 399.
- a first object of the invention consists in the use, in a paint, of a calcium carbonate characterised in that the said carbonate is dry-ground in the presence of a grinding aid agent, firstly, and in that the grinding aid agent is, secondly, a copolymer, consisting:
- This grinding aid agent may be designated using the expression of a copolymer of methacrylic acid with a monomer containing an alcoxy or hydroxy polyalkyleneglycol group.
- a calcium carbonate according to the invention enables a cement to be obtained with a much higher degree of spreading.
- the said copolymer is obtained in the acidic form and possibly distilled, and is possibly partially or totally neutralised by one or more neutralisation agents having a monovalent or polyvalent cation, where the said agents are chosen preferentially from among ammonia or from among calcium, magnesium hydroxides and/or oxides, or from among sodium, potassium or lithium hydroxides, or from among the aliphatic and/or cyclic primary, secondary or tertiary amines, such as preferentially stearylamine, the ethanolamines (mono-, di- and triethanolamine), mono- and diethylamine, cyclohexylamine, methylcyclohexylamine, amino methyl propanol, morpholine, and preferentially in that the neutralisation agent is chosen from among triethanolamine and sodium hydroxide.
- the neutralisation agent is chosen from among triethanolamine and sodium hydroxide.
- copolymer is obtained by processes of radical polymerisation in solution, in a direct or reverse emulsion, in suspension or precipitation in solvents, in the presence of catalytic systems and chain transfer agents, or again by processes of controlled radical polymerisation, and preferentially by nitroxide mediated polymerisation (NMP) or by cobaloximes, by atom transfer radical polymerisation (ATRP), by controlled radical polymerisation by sulphurated derivatives, chosen from among carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
- NMP nitroxide mediated polymerisation
- ATRP atom transfer radical polymerisation
- sulphurated derivatives chosen from among carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
- the said copolymer may possibly, before or after the total or partial neutralisation reaction, be treated and separated into several phases, according to static or dynamic processes known to the skilled man in the art, by one or more polar solvents belonging preferentially to the group constituted by water, methanol, ethanol, propanol, isopropanol, the butanols, acetone and tetrahydrofuran or their blends.
- polar solvents belonging preferentially to the group constituted by water, methanol, ethanol, propanol, isopropanol, the butanols, acetone and tetrahydrofuran or their blends.
- One of the phases then corresponds to the polymer used according to the invention.
- This use is also characterised in that 0.05% to 5%, preferentially 0.1% to 3%, and very preferentially 0.1% to 1%, by dry weight of the said copolymer relative to the dry weight of calcium carbonate is used during the dry grinding of the said carbonate.
- a second purpose of the invention consists of the paints obtained by the use of dry-ground calcium carbonate according to the invention.
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 3000 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the prior art, which is diethylene glycol.
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 3000 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 1400 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the prior art, which is diethylene glycol.
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 1400 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- n° 2 and 4 The polymer used in tests n° 2 and 4 is obtained by polymerisation techniques well known to the skilled man in the art.
- the temperature is then raised and 604.78 g is distilled.
- the temperature is brought down to between 50 and 60° C., and 69.34 g of sodium hydroxide at 50% mass in water is added to the reactive medium.
- the medium is diluted with 20.85 g of water. It is cooled again before obtaining the polymer of the invention.
- Certain optical characteristics of the paints obtained were also measured, such as notably L whiteness, the “3 Hunterlab filters” Sub-tone, covering power or contrast ratio, and the level of brightness at angles equal to 60° and 85°.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Disintegrating Or Milling (AREA)
Abstract
A paint comprising a calcium carbonate that is obtained by dry-grinding in the presence of a grinding aid agent comprising a copolymer of (meth)acrylic acid with a monomer containing an alkoxy or hydroxy polyalkyleneglycol group.
Description
- The present invention concerns the field of paints, where the said paints contain at least one mineral matter which is a calcium carbonate obtained by dry grinding.
- Grinding using a dry process (as opposed to in an aqueous medium) of calcium carbonate is described in the documents “Beitrag zur Aufklärung der Wirkungsweise von Mahlhilfsmitteln” (“Freiberger Forschungshefte” VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, Germany (1975)). and “Calcium Carbonate” (Birkhäuser Verlag, 2001).
- This grinding, which leads to a reduction in the sizes of the individual particles of calcium carbonate by mechanical action, is assisted by grinding agents which can be classified into the following 3 categories.
- The first comprises the weak acids (formic, acetic, lactic, adipic as mentioned in document FR 2 863 914, or stearic as indicated in document EP 0 510 890), and their salts (sodium lignin sulfonate, sodium acetate, etc.). The second includes the weak bases, and notably the amines (see document GB 2 179 268). The third, and the most commonly used, since it is the most effective, includes the glycol-based alcohols, including notably diethylene glycol illustrated in documents WO 2002/081 573 and U.S. 2003/019 399.
- Although they are still the most effective, the latter lead to calcium carbonates with a high quantity of volatile organic compounds (VOCs). For this reason, finding an alternative solution to these glycol-based grinding aid agents which is at least as effective as them in terms of the final application would constitute a major contribution to the state of the technique.
- With this regard, a first object of the invention consists in the use, in a paint, of a calcium carbonate characterised in that the said carbonate is dry-ground in the presence of a grinding aid agent, firstly, and in that the grinding aid agent is, secondly, a copolymer, consisting:
- a) of at least one anionic monomer chosen from among acrylic acid, methacrylic acid and their blends,
- b) and of at least one non-ionic monomer, of formula (I):
- where:
-
- m, n, p and q are integers such that: m, n, p≦150, q≧1, and 5≦(m+n+p)q≦150, and preferentially 15≦(m+n+p)q≦120,
- R1 represents hydrogen or the methyl or ethyl radical,
- R2 represents hydrogen or the methyl or ethyl radical,
- R represents a radical containing an unsaturated polymerisable function, preferentially belonging to the group of vinylics, or to the group of acrylic, methacrylic, maleic esters, or to the group of unsaturated urethanes such as acrylurethane, methacrylurethane, α-α′ dimethyl-isopropenyl-benzylurethane, allylurethane, or to the group of allylic or vinylic ethers, whether or not substituted, or again to the group of ethylenically unsaturated amides or imides, or again to the group constituted by acrylamide and methacrylamide,
- R′ represents hydrogen or a hydrocarbonated radical with 1 to 40 carbon atoms, preferentially 1 to 4 carbon atoms, where R′ is very preferentially the methyl radical,
- or a blend of several monomers of formula (I),
- c) and possibly of at least one other monomer chosen from among (meth)acrylic anhydride, (meth)acrylamide, or from among the (meth)acrylic esters, such as preferentially the acrylates and methacrylates with 1 to 20 carbon atoms in their ester radical, such as very preferentially the methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, ter-butyl or 2-ethylhexyl acrylates, the methyl or ethyl methacrylates, the hydroxylated methacrylates such as the hydroxyethyl and hydroxypropyl methacrylates, or from among the aromatic vinylic monomers such as preferentially styrene, α-methylstyrene, styrene sulfonate, or acrylamido-2-methyl-2-propane-sulfonic acid, or from among the organophosphate monomers, such as preferentially the acrylate and methacrylate phosphates of ethylene glycol, or the acrylate and methacrylate phosphates of oxyethylene and/or oxypropylene glycol, and their blends.
- This grinding aid agent may be designated using the expression of a copolymer of methacrylic acid with a monomer containing an alcoxy or hydroxy polyalkyleneglycol group.
- The examples of the present Application show that, in comparison with a calcium carbonate which is dry ground with a diethylene glycol, a calcium carbonate according to the invention enables a cement to be obtained with a much higher degree of spreading.
- This use is also characterised in that the said copolymer consists, expressed as a percentage by weight of the monomers (the sum of the percentages by weight of all the monomers equals 100%):
- a) 0.5% to 50%, preferentially 1% to 25%, and very preferentially 5% to 20%, of at least one anionic monomer chosen from among acrylic acid, methacrylic acid and their blends,
- b) of 50% to 99.5%, preferentially 75% to 99%, and very preferentially 80% to 95%, of at least one non-ionic monomer, of formula (I):
- where:
-
- m, n, p and q are integers such that: m, n, p≦150, q≧1, and 5≦(m+n+p)q≦150, and preferentially 15≦(m+n+p)q≦120,
- R1 represents hydrogen or the methyl or ethyl radical,
- R2 represents hydrogen or the methyl or ethyl radical,
- R represents a radical containing an unsaturated polymerisable function, preferentially belonging to the group of vinylics, or to the group of acrylic, methacrylic, maleic esters, or to the group of unsaturated urethanes such as acrylurethane, methacrylurethane, α-α′ dimethyl-isopropenyl-benzylurethane, allylurethane, or to the group of allylic or vinylic ethers, whether or not substituted, or again to the group of ethylenically unsaturated amides or imides, or again to the group constituted by acrylamide and methacrylamide,
- R′ represents hydrogen or a hydrocarbonated radical with 1 to 40 carbon atoms, preferentially 1 to 4 carbon atoms, where R′ is very preferentially the methyl radical,
- or a blend of several monomers of formula (I),
- c) 0% to 50% of at least one other monomer chosen from among (meth)acrylic anhydride, (meth)acrylamide, or from among the (meth)acrylic esters, such as preferentially the acrylates and methacrylates with 1 to 20 carbon atoms in their ester radical, such as very preferentially the methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, ter-butyl or 2-ethylhexyl acrylates, the methyl or ethyl methacrylates, the hydroxylated methacrylates such as the hydroxyethyl and hydroxypropyl methacrylates, or from among the aromatic vinylic monomers such as preferentially styrene, α-methylstyrene, styrene sulfonate, or acrylamido-2-methyl-2-propane-sulfonic acid, or from among the organophosphate monomers, such as preferentially the acrylate and methacrylate phosphates of ethylene glycol, or the acrylate and methacrylate phosphates of oxyethylene and/or oxypropylene glycol, and their blends.
- This use is also characterised in that the said copolymer is obtained in the acidic form and possibly distilled, and is possibly partially or totally neutralised by one or more neutralisation agents having a monovalent or polyvalent cation, where the said agents are chosen preferentially from among ammonia or from among calcium, magnesium hydroxides and/or oxides, or from among sodium, potassium or lithium hydroxides, or from among the aliphatic and/or cyclic primary, secondary or tertiary amines, such as preferentially stearylamine, the ethanolamines (mono-, di- and triethanolamine), mono- and diethylamine, cyclohexylamine, methylcyclohexylamine, amino methyl propanol, morpholine, and preferentially in that the neutralisation agent is chosen from among triethanolamine and sodium hydroxide.
- This use is also characterised in that the said copolymer is obtained by processes of radical polymerisation in solution, in a direct or reverse emulsion, in suspension or precipitation in solvents, in the presence of catalytic systems and chain transfer agents, or again by processes of controlled radical polymerisation, and preferentially by nitroxide mediated polymerisation (NMP) or by cobaloximes, by atom transfer radical polymerisation (ATRP), by controlled radical polymerisation by sulphurated derivatives, chosen from among carbamates, dithioesters or trithiocarbonates (RAFT) or xanthates.
- This use is also characterised in that the said copolymer may possibly, before or after the total or partial neutralisation reaction, be treated and separated into several phases, according to static or dynamic processes known to the skilled man in the art, by one or more polar solvents belonging preferentially to the group constituted by water, methanol, ethanol, propanol, isopropanol, the butanols, acetone and tetrahydrofuran or their blends.
- One of the phases then corresponds to the polymer used according to the invention.
- This use is also characterised in that 0.05% to 5%, preferentially 0.1% to 3%, and very preferentially 0.1% to 1%, by dry weight of the said copolymer relative to the dry weight of calcium carbonate is used during the dry grinding of the said carbonate.
- A second purpose of the invention consists of the paints obtained by the use of dry-ground calcium carbonate according to the invention.
- In these examples, all the grinding operations are undertaken according to a method well known to the skilled man in the art (document FR 2 901 491 describes such a method). We shall confine ourselves here to indicating the final granulometry of the particles of calcium carbonate obtained after grinding (the skilled man in the art in reality knows how to modify the parameters of the process with a view to obtaining such a granulometry; however, one may also refer to the above-mentioned document).
- In each of the tests n° 1 to 4, a matt paint is produced in aqueous phase by blending whilst stirring of the different constituents, in the proportions in grams as indicated in table 1.
-
Test no 1 2 3 4 Prior Art (PA)/Invention (IN) PA IN PA IN Water 292.0 292.0 292.0 292.0 Ammonium hydroxide (31% 2.0 2.0 2.0 2.0 solution) Coatex ™ P90 (40% solution) 4.0 4.0 4.0 4.0 Mergal ™ K6N 2.0 2.0 2.0 2.0 Byk ™ 034 2.0 2.0 2.0 2.0 TiO2 RL68 41.0 41.0 41.0 41.0 Omyacoat ™ 850 OG 215.0 215.0 215.0 215.0 CaCO3 dry ground according to 328.0 0 0 0 test no1 CaCO3 dry ground according to 0 328.0 0 0 test no2 CaCO3 dry ground according to 0 0 328.0 0 test no3 CaCO3 dry ground according to 0 0 0 328.0 test no4 Acronal ™ 290D 82.0 82.0 82.0 82.0 Monoethylene glycol 10.0 10.0 10.0 10.0 Texanol ™ 10.0 10.0 10.0 10.0 Rheo ™ 3000 12.0 12.0 12.0 12.0 Total (g) 1000.0 1000.0 1000.0 1000.0 Coatex ™ P90 designates a thickener sold by the company COATEX ™, Rheo ™ 3000 designates a thickener sold by the company COATEX ™, Mergal ™ K6N designates a bactericide sold by the company TROY ™, Byk ™ 034 designates an anti-foaming agent sold by the company BYK ™, TiO2 RL68 designates a titanium dioxide powder sold by the company MILLENIUM ™, Omyacoat ™ 850 OG designates a calcium carbonate sold by the company OMYA ™, Acronal ™ 290 D designates a binder sold by the company BASF ™, Texanol ™ designates a coalescence agent sold by the company EASTMANN ™ - This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 3000 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the prior art, which is diethylene glycol.
- After grinding a calcium carbonate is obtained, 73.8% and 48.5% by weight of the particles of which have an average diameter lower respectively than 2 μm and 1 μm (as measured using a Sedigraph™ 5100).
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 3000 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- After grinding a calcium carbonate is obtained, 74.5% and 44.1% by weight of the particles of which have an average diameter lower respectively than 2 μm and 1 μm (as measured using a Sedigraph™ 5100).
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 1400 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the prior art, which is diethylene glycol.
- After grinding a calcium carbonate is obtained, 47.1% and 30.0% by weight of the particles of which have an average diameter lower respectively than 2 μm and 1 μm (as measured using a Sedigraph™ 5100).
- This test illustrates the prior art and uses a calcium carbonate obtained by dry grinding in the presence of 1400 ppm (relative to the dry weight of calcium carbonate) of a grinding agent of the invention which is a polymer consisting, by weight percentage, 81.5% of methoxy polyethylene glycol methacrylate of molecular weight 2000, 4.9% of methacrylic acid, and 13.6% of acrylic acid.
- After grinding a calcium carbonate is obtained, 45.4% and 28.0% by weight of the particles of which have an average diameter lower respectively than 2 μm and 1 μm (as measured using a Sedigraph™ 5100).
- The polymer used in tests n° 2 and 4 is obtained by polymerisation techniques well known to the skilled man in the art.
- In a first beaker the following are introduced at ambient temperature and whilst stirring: 259.02 of methoxy polyethylene glycol methacrylate of molecular weight equal to 2000 g/mol, a solution containing 15.36 g of methacrylic acid and 274.39 g of water, a solution containing 69.86 g of untreated water and 50.25 g of acrylic acid
- In a second beaker the following are introduced at ambient temperature and whilst stirring: 2.38 g of thiolactic acid (of 98.5% mass purity) and 52.14 g of water.
- In a third beaker the following are introduced at ambient temperature and whilst stirring: 2.84 g of ammonium persulphate (NH4)2S2O8 and 51.90 g of water.
- In a fourth beaker the following are introduced at ambient temperature and whilst stirring: 0.56 g of ammonium persulphate (NH4)2S2O8 and 10.87 g of water.
- In a single-casing cylindrical reactor, surmounted by a refrigerating column, by an anchor stirring system and 3 inlets, 351.39 g of water and 295.61 g of isopropanol are introduced. The reactive medium is heated whilst stirring (230 rpm) to 84±2° C. The contents of the first 3 beakers are introduced into the reactive medium in 2 hours. The introduction nozzles are then rinsed with 20.84 g of water (this water goes directly into the reactive medium). The solution of the 4th beaker is then added to the reactive medium, and the blend is fired for 1 hour at 84±2° C. (at 230 rpm). At the end of the reaction the device is rinsed with 52.13 g of water. The temperature is then raised and 604.78 g is distilled. The temperature is brought down to between 50 and 60° C., and 69.34 g of sodium hydroxide at 50% mass in water is added to the reactive medium. Finally the medium is diluted with 20.85 g of water. It is cooled again before obtaining the polymer of the invention.
- For each of the tests n° 1 to 4, the Stormer™, ICI™ and Brookfield™ viscosities were determined according to the methods well known to the skilled man in the art.
- Certain optical characteristics of the paints obtained were also measured, such as notably L whiteness, the “3 Hunterlab filters” Sub-tone, covering power or contrast ratio, and the level of brightness at angles equal to 60° and 85°.
- The methods used are notably described in document FR 2 872 815.
- The results are shown in tables 2 and 3.
-
TABLE 2 Test Test Test Test Viscosities no 1 no 2 no 3 no 4 Time t = 0 μI (P) 1.9 1.9 1.6 1.6 μS (K.U) 102 106 99 100 μB 10 (mPa · s) 13700 15100 11600 11100 μB100 (mPa · s) 3300 3600 2900 3000 Time t = 24 hours μB 10 (mPa · s) 18900 18400 12700 12300 μB100 (mPa · s) 4900 4750 3500 3100 Instant t = 7 days μB 10 (mPa · s) 43900 32100 15400 12800 50° C. μB 10 (mPa · s) 14000 8340 4500 3200 Instant t = μB 10 (mPa · s) Taken 42800 15800 13800 1 month 50° C. μB 10 (mPa · s) in 12000 4700 3400 mass μI (P): ICI ™ viscosity μS (K.U): Stormer ™ viscosity μB 10 (mPa · s): Brookfield ™ viscosity determined at 10 revolutions per minute μB 100 (mPa · s): Brookfield ™ viscosity determined at 100 revolutions per minute -
TABLE 3 Test no 1 2 3 4 Whiteness. 99.2 99.1 98.7 98.6 Measurement of the “L” “3 Hunterlab filters” Sub-tone 2.2 2.3 2.3 2.2 Value of b Covering power of dry film 96.9% 96.8% 96.0% 95.9% Contrast ratio RC = Yn/Yb Level of brightness t = 72 h 60° 4.7 4.6 4.8 4.7 85° 32.9 33.5 14.9 15.6 - By comparing the tests 2 by 2 (1 to 2, and 3 to 4), it is observed that the optical properties of the paint films are in the context of the invention at the same level as for the prior art.
- Conversely, a clear drift of the Brookfield™ viscosity is observed in the case of paints formulated according to the prior art. At the same time, this viscosity remains much more stable in the context of the invention.
- We have therefore succeeded in developing a dry-ground calcium carbonate which, in the paint field, has a more stable Brookfield viscosity, without modifying the optical properties of the dry film.
Claims (21)
1-7. (canceled)
8. A paint, comprising a calcium carbonate which is dry-ground in the presence of a grinding aid agent comprising a copolymer comprising:
a) at least one anionic monomer selected from the group consisting of acrylic acid and methacrylic acid;
b) at least one non-ionic monomer of formula (I)
wherein
m, n, p, and q are integers such that m, n, and p≦150, q≧1, and 5≦(m+n+p)q≦150,
R1 and R2 independently represent hydrogen or a methyl or ethyl radical,
R represents a radical containing an unsaturated polymerizable function selected from the group consisting of a vinylic, an acrylic ester, a methacrylic ester, a maleic ester, an acrylurethane, a methacrylurethane, an α-α′ dimethyl-isopropenyl-benzylurethane, an allylurethane, an optionally substituted allylic ether, an optionally substituted vinylic ether, an ethylenically unsaturated amide, an ethylenically unsaturated imide, an acrylamide, and a methacrylamide;
R′ represents hydrogen or a hydrocarbon radical with 1 to 40 carbon atoms; and
c) optionally, at least one other monomer selected from (meth)acrylic anhydride, a (meth)acrylamide, an acrylate with 1 to 20 carbon atoms in its ester radical, a methacrylate with 1 to 20 carbon atoms in its ester radical, a hydroxylated methacrylate, an aromatic vinylic monomer, an acrylate phosphate of ethylene glycol, an acrylate phosphate of oxyethylene glycol, an acrylate phosphate of oxypropylene glycol, an acrylate phosphate of oxyethylene and oxypropylene glycol, a methacrylate phosphate of ethylene glycol, a methacrylate phosphate of oxyethylene glycol, a methacrylate phosphate of oxypropylene glycol, and a methacrylate phosphate of oxyethylene and oxypropylene glycol.
9. The paint of claim 8 , wherein said copolymer comprises, expressed as a percentage by weight of the monomers in which the sum of the percentages by weight of all the monomers equals 100%:
a) 0.5% to 50% of the at least one anionic monomer;
b) 50% to 99.5% of the at least one non-ionic monomer of formula (I); and
c) 0% to 50% of the at least one other monomer.
10. The paint of claim 8 , wherein said copolymer is obtained in acidic form and optionally distilled, and is, optionally, partially or totally neutralized by at least one neutralization agent having a monovalent or polyvalent cation, wherein the neutralization agent is at least one selected from the group consisting of ammonia, calcium hydroxide, calcium oxide, magnesium hydroxide, magnesium oxide, sodium hydroxide, potassium hydroxide, lithium hydroxide, an aliphatic primary amine, an aliphatic secondary amine, an aliphatic tertiary amine, a cyclic secondary amine, and a cyclic tertiary amine.
11. The paint of claim 8 , wherein said copolymer is obtained by
radical polymerization in solution, in a direct or reverse emulsion, in suspension or precipitation in a solvent, in the presence of at least one selected from the group consisting of a catalytic system and a chain transfer agent,
controlled radical polymerization by nitroxide mediated polymerization (NMP), or by a cobaloxime,
atom transfer radical polymerization (ATRP), or
controlled radical polymerization by at least one sulphurated derivative selected from the group consisting of a carbamate, a dithioester, a trithiocarbonate, RAFT, and a xanthate.
12. The paint of claim 10 , wherein said copolymer is totally or partially neutralized and, before or after the total or partial neutralization reaction, is treated and separated into several phases, according to static or dynamic processes, by at least one polar solvent selected from the group consisting of water, methanol, ethanol, propanol, isopropanol, a butanol, acetone, and tetrahydrofuran.
13. The paint of claim 8 , wherein 0.05% to 5% by dry weight of the copolymer relative to a dry weight of calcium carbonate is used during a dry grinding of said calcium carbonate.
14. The paint of claim 8 , wherein, in the copolymer, m, n, p, and q are integers such that: 15≦(m+n+p)q≦120.
15. The paint of claim 8 , wherein, in the copolymer, R′ is a hydrocarbon radical with 1 to 4 carbon atoms
16. The paint of claim 8 , wherein, in the copolymer, R′ is a methyl radical
17. The paint of claim 8 , wherein, in the copolymer, the at least one other monomer is present and is methyl acrylate, ethyl acrylate, isopropyl acrylate, n-propyl acrylate, isobutyl acrylate, n-butyl acrylate, tert-butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, or ethyl methacrylate.
18. The paint of claim 8 , wherein, in the copolymer, the at least one other monomer is present and is hydroxyethyl methacrylate, hydroxypropyl methacrylate, styrene, α-methylstyrene, styrene sulfonate, or acrylamido-2-methyl-2-propane-sulfonic acid.
19. The paint of claim 8 , wherein, in the copolymer, the at least one other monomer is present and is an acrylate phosphate of ethylene glycol, a methacrylate phosphate of ethylene glycol, an acrylate phosphate of oxyethylene glycol, an acrylate phosphate of oxypropylene glycol, an acrylate phosphate of oxyethylene and oxypropylene glycol, a methacrylate phosphate of oxyethylene glycol, a methacrylate phosphate of oxypropylene glycol, or a methacrylate phosphate of oxyethylene and oxypropylene glycol.
20. The paint of claim 8 , wherein, in the copolymer, the at least one anionic monomer is present in 1% to 25% by weight, based on a sum of percentages by weight of all monomers being 100%.
21. The paint of claim 8 , wherein, in the copolymer, the at least one anionic monomer is present in 5% to 20% by weight, based on a sum of percentages by weight of all monomers being 100%.
22. The paint of claim 8 , wherein, in the copolymer, the at least one non-ionic monomer of formula (I) is present in 75% to 99% by weight, based on a sum of percentages by weight of all monomers being 100%.
23. The paint of claim 8 , wherein, in the copolymer, the at least one non-ionic monomer of formula (I) is present in 80% to 95% by weight, based on a sum of percentages by weight of all monomers being 100%.
24. The paint of claim 8 , wherein 0.1% to 3% by dry weight of the copolymer relative to a dry weight of the calcium carbonate is used in dry grinding.
25. The paint of claim 8 , wherein 0.1% to 1% by dry weight of the copolymer relative to a dry weight of the calcium carbonate is used in dry grinding.
26. The paint of claim 8 , wherein 1% to 5% by dry weight of the copolymer relative to a dry weight of the calcium carbonate is used in dry grinding.
27. The paint of claim 8 , wherein the copolymer is partially or totally neutralized and the neutralization agent is triethanolamine or sodium hydroxide.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/226,879 US20110319544A1 (en) | 2007-03-05 | 2011-09-07 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
US13/470,882 US8445579B2 (en) | 2007-03-05 | 2012-05-14 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0701595A FR2913428B1 (en) | 2007-03-05 | 2007-03-05 | USE IN PAINT, DRY CAULK CALCIUM CARBONATE WITH COPOLYMER OF (METH) ACRYLIC ACID WITH ALCOXY OR HYDROXY POLYALKYLENE GLYCOL FUNCTION. |
FR0701595 | 2007-03-05 | ||
PCT/IB2008/000532 WO2008107786A1 (en) | 2007-03-05 | 2008-02-26 | Use in paint of dry-ground calcium carbonate with (meth)acrylic acid copolymer with alkoxy or hydroxy polyalkylene glycol function |
US52320709A | 2009-07-15 | 2009-07-15 | |
US13/226,879 US20110319544A1 (en) | 2007-03-05 | 2011-09-07 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Related Parent Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/523,207 Continuation US20100111809A1 (en) | 2007-03-05 | 2008-02-26 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
PCT/IB2008/000532 Continuation WO2008107786A1 (en) | 2007-03-05 | 2008-02-26 | Use in paint of dry-ground calcium carbonate with (meth)acrylic acid copolymer with alkoxy or hydroxy polyalkylene glycol function |
US52320709A Continuation | 2007-03-05 | 2009-07-15 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/470,882 Continuation US8445579B2 (en) | 2007-03-05 | 2012-05-14 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Publications (1)
Publication Number | Publication Date |
---|---|
US20110319544A1 true US20110319544A1 (en) | 2011-12-29 |
Family
ID=38896771
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/523,207 Abandoned US20100111809A1 (en) | 2007-03-05 | 2008-02-26 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
US13/226,879 Abandoned US20110319544A1 (en) | 2007-03-05 | 2011-09-07 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
US13/470,882 Expired - Fee Related US8445579B2 (en) | 2007-03-05 | 2012-05-14 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/523,207 Abandoned US20100111809A1 (en) | 2007-03-05 | 2008-02-26 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/470,882 Expired - Fee Related US8445579B2 (en) | 2007-03-05 | 2012-05-14 | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
Country Status (11)
Country | Link |
---|---|
US (3) | US20100111809A1 (en) |
EP (1) | EP2125234B1 (en) |
CN (1) | CN101583430B (en) |
AR (1) | AR065478A1 (en) |
CL (1) | CL2008000637A1 (en) |
ES (1) | ES2460569T3 (en) |
FR (1) | FR2913428B1 (en) |
RU (1) | RU2477737C2 (en) |
TW (1) | TW200906982A (en) |
UY (1) | UY30946A1 (en) |
WO (1) | WO2008107786A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8445579B2 (en) | 2007-03-05 | 2013-05-21 | Coatex S.A.S. | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
US8445561B2 (en) | 2007-03-05 | 2013-05-21 | Coatex S.A.S. | Use in a hydraulic binder composition of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid and an alkoxy or hydroxy polyalkyleneglycol group |
CN103525235A (en) * | 2013-09-24 | 2014-01-22 | 淮南师范学院 | Aqueous rust-removal and rustproof nano coating and preparation method thereof |
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PT2455429E (en) * | 2010-11-19 | 2013-11-07 | Omya Int Ag | Method for preparing aqueous suspensions of mineral materials using amines combined with vinyl carboxylic polymers |
WO2012082741A1 (en) | 2010-12-13 | 2012-06-21 | Sun Chemical Coporation | Methods of solubilizing milling media in pigment particle dispersions |
JP2014505753A (en) * | 2010-12-17 | 2014-03-06 | ビーエーエスエフ ソシエタス・ヨーロピア | Stable polyacrylic acid, its manufacture and its use |
US9309153B2 (en) | 2012-04-27 | 2016-04-12 | Halliburton Energy Services, Inc. | Wide temperature range cement retarder |
CN102732078B (en) * | 2012-07-06 | 2014-03-19 | 吴燕湘 | Water-based additive composite |
CN102827524B (en) * | 2012-08-23 | 2014-08-27 | 吴燕湘 | Water-based coating composition |
PL2910609T3 (en) * | 2014-02-21 | 2018-01-31 | Omya Int Ag | Process for the preparation of a calcium carbonate filler product |
FR3017872B1 (en) | 2014-02-21 | 2016-05-20 | Coatex Sas | USE OF STYRENE COPOLYMERS AND MALEIC ANHYDRIDE FOR PREPARING MINERAL PARTICLES |
WO2015128021A1 (en) | 2014-02-26 | 2015-09-03 | Basf Se | Process for preparing polyamines |
CN104031190A (en) * | 2014-06-12 | 2014-09-10 | 东升新材料(山东)有限公司 | Preparation of efficient ground calcium carbonate grinding dispersant by photo-initiating room-temperature RAFT (Reversible Additive Fragment Transfer) polymerization |
US10832333B1 (en) * | 2015-12-11 | 2020-11-10 | State Farm Mutual Automobile Insurance Company | Structural characteristic extraction using drone-generated 3D image data |
US11014858B2 (en) | 2016-03-30 | 2021-05-25 | Gcp Applied Technologies Inc. | Mineral grinding |
CN113348214A (en) * | 2019-02-26 | 2021-09-03 | Omya国际股份公司 | Method for preparing surface-treated calcium carbonate material |
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US4013602A (en) * | 1972-10-09 | 1977-03-22 | Pluss-Staufer Ag | Ultrafine natural calcium carbonates as fillers in varnishes and paints |
JPH07100141B2 (en) | 1987-12-10 | 1995-11-01 | 東亞合成株式会社 | Dry grinding aid |
FR2650594B1 (en) * | 1989-08-04 | 1992-04-03 | Coatex Sa | APPLICATION TO AQUEOUS PIGMENTARY SUSPENSIONS OF CALCIUM CARBONATE OF A POLYCARBOXYLIC AGENT WITH PHOSPHATE OR PHOSPHONE FUNCTION INHIBITING THE EFFECT OF SHOCK CAUSED BY THE INTRODUCTION OF AN ELECTROLYTE IN CONCENTRATED FORM |
JPH10338518A (en) * | 1997-06-03 | 1998-12-22 | Kurimoto Ltd | Production of calcium carbonate |
US6414065B1 (en) * | 1999-11-05 | 2002-07-02 | Celanese International Corporation | Multifunctional poly(vinyl alcohol) binder for fine particle size calcium carbonate pigment |
FR2810261B1 (en) * | 2000-06-15 | 2002-08-30 | Coatex Sa | USE OF LOW ANIONIC COPOLYMERS AS A DISPERSING AGENT AND / OR AID FOR GRINDING AQUEOUS SUSPENSION OF MINERALS, AQUEOUS SUSPENSIONS OBTAINED AND USES THEREOF |
FR2901491B1 (en) * | 2006-05-24 | 2009-03-20 | Coatex Sas | DRY GRINDING METHOD OF MATERIALS CONTAINING CARBONATE ORE |
FR2913428B1 (en) | 2007-03-05 | 2009-06-05 | Coatex Soc Par Actions Simplif | USE IN PAINT, DRY CAULK CALCIUM CARBONATE WITH COPOLYMER OF (METH) ACRYLIC ACID WITH ALCOXY OR HYDROXY POLYALKYLENE GLYCOL FUNCTION. |
FR2913420B1 (en) | 2007-03-05 | 2009-05-01 | Coatex Soc Par Actions Simplif | USE IN HYDRAULIC BINDER COMPOSITION, DRY-CURED CALCIUM CARBONATE WITH COPOLYMER OF (METH) ACRYLIC ACID, AND ALCOXY OR HYDROXY POLYALKYLENE GLYCOL FUNCTION. |
FR2913426B1 (en) | 2007-03-05 | 2009-06-05 | Coatex Soc Par Actions Simplif | USE AS A RHEOLOGY AGENT IN A LOADED PLASTIC PULP, A DRY CURED CARBONATE WITH A COPOLYMER OF (METH) ACRYLIC ACID WITH AN ALCOXY OR HYDROXY POLYALKYLENE GLYCOL FUNCTION. |
-
2007
- 2007-03-05 FR FR0701595A patent/FR2913428B1/en active Active
-
2008
- 2008-02-15 TW TW097105286A patent/TW200906982A/en unknown
- 2008-02-26 US US12/523,207 patent/US20100111809A1/en not_active Abandoned
- 2008-02-26 WO PCT/IB2008/000532 patent/WO2008107786A1/en active Application Filing
- 2008-02-26 EP EP08719243.1A patent/EP2125234B1/en not_active Not-in-force
- 2008-02-26 RU RU2009136590/05A patent/RU2477737C2/en not_active IP Right Cessation
- 2008-02-26 ES ES08719243.1T patent/ES2460569T3/en active Active
- 2008-02-26 AR ARP080100786A patent/AR065478A1/en unknown
- 2008-02-26 CN CN200880001684XA patent/CN101583430B/en not_active Expired - Fee Related
- 2008-03-03 CL CL200800637A patent/CL2008000637A1/en unknown
- 2008-03-04 UY UY30946A patent/UY30946A1/en not_active Application Discontinuation
-
2011
- 2011-09-07 US US13/226,879 patent/US20110319544A1/en not_active Abandoned
-
2012
- 2012-05-14 US US13/470,882 patent/US8445579B2/en not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8445579B2 (en) | 2007-03-05 | 2013-05-21 | Coatex S.A.S. | Use in a paint of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid with an alkoxy or hydroxy polyalkyleneglycol group |
US8445561B2 (en) | 2007-03-05 | 2013-05-21 | Coatex S.A.S. | Use in a hydraulic binder composition of a dry-ground calcium carbonate with a copolymer of (meth)acrylic acid and an alkoxy or hydroxy polyalkyleneglycol group |
CN103525235A (en) * | 2013-09-24 | 2014-01-22 | 淮南师范学院 | Aqueous rust-removal and rustproof nano coating and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
RU2477737C2 (en) | 2013-03-20 |
FR2913428A1 (en) | 2008-09-12 |
CN101583430A (en) | 2009-11-18 |
US20120225988A1 (en) | 2012-09-06 |
FR2913428B1 (en) | 2009-06-05 |
US8445579B2 (en) | 2013-05-21 |
RU2009136590A (en) | 2011-04-10 |
US20100111809A1 (en) | 2010-05-06 |
WO2008107786A1 (en) | 2008-09-12 |
EP2125234A1 (en) | 2009-12-02 |
AR065478A1 (en) | 2009-06-10 |
CN101583430B (en) | 2013-11-20 |
CL2008000637A1 (en) | 2008-09-26 |
UY30946A1 (en) | 2008-10-31 |
EP2125234B1 (en) | 2014-04-16 |
ES2460569T3 (en) | 2014-05-13 |
TW200906982A (en) | 2009-02-16 |
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