WO2014200755A1 - Phosphate ester dispersion promoting agent and dispersion comprising the same - Google Patents

Phosphate ester dispersion promoting agent and dispersion comprising the same Download PDF

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Publication number
WO2014200755A1
WO2014200755A1 PCT/US2014/040605 US2014040605W WO2014200755A1 WO 2014200755 A1 WO2014200755 A1 WO 2014200755A1 US 2014040605 W US2014040605 W US 2014040605W WO 2014200755 A1 WO2014200755 A1 WO 2014200755A1
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WO
WIPO (PCT)
Prior art keywords
acid
dispersion
range
phosphate ester
substituted
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PCT/US2014/040605
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English (en)
French (fr)
Inventor
Jin Wang
Gang Duan
Jinsong Wen
Kuai LIN
Yinchao ZHANG
Hua LAI
Xiahu CHEN
Original Assignee
Valspar Sourcing, Inc.
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.)
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Publication date
Application filed by Valspar Sourcing, Inc. filed Critical Valspar Sourcing, Inc.
Priority to EP14810305.4A priority Critical patent/EP3007813A4/en
Publication of WO2014200755A1 publication Critical patent/WO2014200755A1/en
Priority to US14/966,136 priority patent/US20160096965A1/en

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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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

Definitions

  • the present disclosure relates to a phosphate ester dispersion promoting agent and a process for the preparation thereof.
  • the present disclosure also relates to a dispersion of a particulate solid comprising the phosphate ester dispersion promoting agent and use of the phosphate ester dispersion promoting agent for dispersing a particulate solid.
  • Particulate solids in particular inorganic particulate solids
  • inorganic particulate solids have been widely used in various applications including coatings, adhesives, inks, paints, stains, and so on.
  • particulate solids for example, pigments and fillers
  • the particulate solids serve to not only provide a good hiding power and a desirable color, but also provide improved physical and chemical properties such as chemical resistance and thermal stability.
  • Preferred particulate solids that are used as pigment or filler typically have a relatively small particle size, such as a particle size of micrometers or even nanometers. Using such particulate solids often presents a problem in that the particulate solids are prone to aggregate and difficult to homogenously disperse in a dispersing medium.
  • Dispersion aids may be used to improve the dispersibility of particulate solids so as to form a stable dispersion of the particular solids.
  • Such dispersion aids typically are cationic, anionic, or non-ionic surface active substances. These substances can be directly applied to the particulate solids, or can be added to a dispersion of the particulate solids.
  • the dispersion aids can attach to the surface of the particulate solids, serving to promote dispersion and/or prevent aggregation. It has been known that the dispersion aids suitable for promoting dispersion and/or preventing aggregation of the particulate solids comprise, among others, fat acids, organic silicon compounds, alkanol amines, and polyols.
  • the present disclosure provides a dispersion of a particulate solid dispersed with aid of a novel phosphate ester dispersion promoting agent.
  • a dispersion of a particulate solid comprising a phosphate ester as a dispersion promoting agent, a particulate solid, a dispersing medium, and optionally one or more additional additives.
  • the phosphate ester has the structure of formula (I):
  • R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1, or 2.
  • the polyester residue R has a number-average molecular weight in the range of 200 to 1,500 g/mol. More preferably, the ratio by number of the ether oxygen atom, if present, to carboxylate ester groups -COO- in the skeleton is in the range of 1 : 2 to 3: 1.
  • the polyester residue R has the structure represented by formula (1-1) or (1-2):
  • each R 1 independently represents, at each occurrence, substituted or
  • each R independently represents, at each occurrence, C 2 -Ci 8 alkylene; or -(CH 2 CH 2 0) p CH 2 CH 2 -, in which p is in the range of 1 to 6; or -(CH 2 CH 2 CH 2 0) q CH 2 CH 2 CH 2 -, in which q is in the range of 1 to 6; or
  • R" is -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -; m is in the range of 0 to 100; and n is in the range of 0 to 100.
  • the dispersion comprises, relative to the total weight of the dispersion of the particulate solid, 0.5 to 3.0% by weight of the phosphate ester as a dispersion promoting agent; 40 to 80%> by weight of the particulate solid; 20 to 40 % by weight of the dispersing medium; and 0 to 10%> by weight of one or more additional additives.
  • R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1 or 2.
  • the process comprising: (i) providing at least one hydroxyl compound containing a free carboxylic acid group represented by the general formula (II)
  • the hydroxyl compound is provided by esterification of at least one hydroxycarboxylic acid and/or its lactone, or by esterification of at least one dicarboxylic acid or polycarboxylic acid with at least one diol in a 1 : 1 or greater molar equivalent ratio of the acid to the diol.
  • the hydroxyl compound has the structure represented by formula (II- 1) or ( ⁇ -2)
  • each R independently represents, at each occurrence, C 2 -Ci 8 alkylene; or -(CH 2 CH 2 0) p CH 2 CH 2 -, in which p is in the range of 1 to 6; or -(CH 2 CH 2 CH 2 0) q CH 2 CH 2 CH 2 -, in which q is in the range of 1 to 6; or
  • R" is -CH 2 CH 2 - or -CH 2 CH 2 CH 2 -; m is in the range of 0 to 100; and n is in the range of 0 to 100.
  • the particulate solids may comprise pigments or fillers. More preferably, the particulate solids may comprise inorganic pigments or inorganic fillers, such as metals, alloys, metal oxides, metal salts, oxymetallic compounds, nonmetal oxides, or the like.
  • the specific examples of such particulate solids may comprise titanium dioxide, calcium carbonate, barium sulfate, silicon dioxide, or silicates.
  • the particulate solid may be titanium dioxide, such as titanium dioxide in the form of powder.
  • the phosphate ester dispersion promoting agent disclosed herein may contain a polyester residue containing in its skeleton optionally at least one ether oxygen atom -O- and further at least one free carboxylic group.
  • the phosphate ester dispersion promoting agent disclosed herein when used for dispersing a particulate solid, can provide the resultant dispersion with a good thixotropic behavior (i.e., a desirable shear-thinning behavior).
  • polyester residue refers to a residue derived from a free carboxylic group-containing polyester, which contains in its skeleton optionally at least one ether oxygen atom -0-.
  • alkylene refers to a linear, branched, or cyclic divalent saturated hydrocarbyl group that may be substituted or unsubstituted.
  • the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
  • Suitable examples of alkylene may include ethylene, propylene, tetramethylene, pentamethylene, 1,3- dimethyltrimethylene, 2,2-dimethyltrimethylene, 3-methylpentamethylene, cyclohexylene, or 1 -isopropyl -2,2-dimethyltrimethylene.
  • alkenylidene refers to a linear, branched, or cyclic divalent unsaturated hydrocarbyl group containing at least one carbon-carbon double bond, which may be substituted or unsubstituted.
  • the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
  • arylene refers to a divalent aromatic group that may be substituted or unsubstituted.
  • the substituent(s) may preferably include a carboxylic, a carboxylate ester, or a carboxylate salt group.
  • a suitable example of arylene may include phenylene that may be unsubstituted or substituted with a carboxyl group.
  • a molar equivalent ratio of the acid to the diol refers to the molar ratio of carboxylic groups of the dicarboxylic acid or polycarboxylic acid to hydroxyl groups of the diol.
  • carboxylic acid as used in the context of esterification with a hydroxyl compound, also includes any suitable ester-forming derivative thereof, which can react with a hydroxyl compound to form a carboxylate ester.
  • the suitable ester-forming derivative of a carboxylic acid is known to a person skilled in the art, and may include, but not limited to, an anhydride, an acyl halide, an ester of a carboxylic acid and a lower alkanol, or the like.
  • compositions are described as having, including, or comprising specific components or fractions, or where processes are described as having, including, or comprising specific process steps, it is contemplated that the compositions or processes as disclosed herein may further comprise other components or fractions or steps, whether or not specifically mentioned in this disclosure, as long as such components or steps do not affect the basic and novel characteristics of the invention, but it is also contemplated that the compositions or processes may consist essentially of, or consist of, the recited components or steps.
  • a As used herein, "a”, “an”, “the”, “at least one”, and “one or more” are used interchangeably. Thus, for example, a dispersion that comprises “a” particulate solid can be interpreted to mean that the dispersion includes “one or more” particulate solids.
  • ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited
  • ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited
  • ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
  • a phosphate ester having formula (I) used as a dispersion promoting agent is provided.
  • the polyester residue R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-; and x is 1 or 2.
  • the polyester residue R has a number-average molecular weight in the range of 200 to 1 ,500 g/mol, more preferably 500 to 1,400 g/mol, and even more preferably 700 to 1 ,200 g/mol.
  • the ratio by number of the ether oxygen atom to carboxylate ester groups -COO- in the skeleton is in the range of 1 :2 to 3 : 1. Preferably, the ratio is about 1 : 1.
  • the polyester residue R that contains in its skeleton optionally at least one ether oxygen atom -O- has the structure represented by formula (I-l) or (1-2):
  • each R 1 independently represents, at each occurrence, substituted or unsubstituted C 2 - Ci 8 alkylene, substituted or unsubstituted C 2 -Ci 8 alkenylidene, or substituted or
  • each R independently represents, at each occurrence, C 2 -Ci 8 alkylene
  • n is in the range of 0 to 100.
  • R independently represents, at each occurrence, a polyester residue containing in its skeleton optionally at least one ether oxygen atom -0-;
  • x 1 or 2
  • R is defined as above;
  • phosphating agent refers to a phosphorus compound which can form a phosphate ester by reaction with a hydroxyl compound.
  • phosphorus oxychloride, phosphorus pentoxide, polyphosphoric acid, pyrophosphoric acid or acetyl phosphate can be used as an example of a phosphating agent. Additional examples can be found in German Patent Application No. DE-A 2,726,854. Phosphorus pentoxide, polyphosphoric acid and pyrophosphoric acid are preferred.
  • the phosphate ester as disclosed herein can be prepared by reaction of one phosphoric acid equivalent of a phosphating agent with one or two equivalents of a hydroxyl compound represented by the general formula (II) as defined above.
  • the reaction can be carried out as described, for example, in US Patent No.
  • one phosphoric acid equivalent means that the phosphating agent can react with one or two equivalents of a hydroxyl compound represented by the general formula (II) stoichiometrically to form a phosphoric acid monoester or diester represented by the general formula (I) as indicated above.
  • a phosphoric acid monoester is expected to form stoichiometrically.
  • a phosphoric acid diester is expected to form stoichiometrically.
  • Intermediate ratios i.e., between one and two equivalents of hydroxyl compound
  • a mixture of monoester and diester species will be formed.
  • polyester residues R's in a phosphate ester of formula (I) may be the same or different.
  • a phosphate ester of formula (I) having different polyester residues R's can be prepared, for example, by first reacting 1 phosphoric acid equivalent of a phosphating agent with 1 equivalent of a hydroxyl compound to form a monoester, then reacting the resulting monoester with 1 equivalent of a hydroxyl compound having a different polyester residue R.
  • a phosphate ester of formula (I) having different polyester residues R's can also be prepared by reacting 1 phosphoric acid equivalent of a phosphating agent with a mixture of hydroxyl compounds having different polyester residues R's.
  • a person skilled in the art can determine the suitable conditions for the reaction of a phosphating agent with a hydroxyl compound according to the types of phosphating agent and hydroxyl compound used, including use of solvent, reaction temperature, and so on.
  • the reaction is carried out at a temperature of at most 100 °C in absence of any solvent.
  • the reaction can be carried out in presence of a suitable inert solvent as described in, for example, EP-A 193019.
  • providing the hydroxyl compound containing a free carboxylic acid group comprises providing a hydroxyl compound containing a free carboxylic acid group having the structure represented by formula (II- 1) or ( ⁇ -2) by esterification of at least one hydroxycarboxylic acid and/or its lactone, or by esterification of at least one dicarboxylic acid or polycarboxylic acid with at least one diol in a 1 : 1 or greater molar equivalent ratio of the acid to the diol:
  • the hydroxyl compound has a number-average molecular weight in the range of 200 to 1,500 g/mol, more preferably 500 to 1,400 g/mol, and even more preferably 700 to 1 ,200 g/mol.
  • the number-average molecular weight can be determined by an acid value of the hydroxyl compound.
  • hydroxycarboxylic acid and/or its lactone may be used as the starting material.
  • Suitable hydroxycarboxylic acids include: 12-hydroxystearic acid, ricinoleic acid, 12-hydroxydodecanoic acid, 5-hydroxydodecanoic acid, 5-hydroxydecanoic acid, 4- hydroxydecanoic acid, glycolic acid, lactic acid, 6-hydroxyhexanoic acid and 5- hydroxypentanoic acid.
  • ricinoleic acid or 12-hydroxystearic acid are used as the hydroxycarboxylic acid.
  • Suitable lactones include: propiolactone, butyro lactone, ⁇ -valerolactone, ⁇ - caprolactone, and Ci_g alkyl substituted ⁇ -caprolactone.
  • ⁇ -caprolactone is used as the lactone.
  • the esterification reaction of hydroxycarboxylic acid and/or its lactone can be effected under conditions that are known in the art.
  • the esterification reaction can be effected in the presence of a catalyst such as p-toluenesulfonic acid, dibutyltin dilaurate or tetrabutyl titanate at a temperature ranging from about 80 °C to about 180 °C.
  • the esterification reaction of 12-hydroxystearic acid as the hydroxycarboxylic acid and ⁇ -caprolactone as the lactone is carried out in the presence of a catalyst at an elevated temperature.
  • a catalyst for example, 12-hydroxystearic acid and ⁇ - caprolactone may be used as the starting materials and provided in a 1 : 1 molar equivalent ratio of carboxyl group to hydroxyl group for the esterification, thereby forming a hydroxyl compound containing a free carboxylic acid group.
  • each R independently represents, at each occurrence
  • the reaction is carried out in a solvent of xylene in the presence of a catalyst of tetrabutyl titanate at an elevated temperature up to 180 °C. Water is removed from the reaction system while the reaction is proceeding.
  • dicarboxylic acid or polycarboxylic acid and diol may be used as the starting material.
  • the molar equivalent ratio of dicarboxylic acid or polycarboxylic acid to diol is 1 : 1 or greater.
  • the molar equivalent ratio of dicarboxylic acid or polycarboxylic acid to diol is in the range of 1 : 1 to 1.2: 1.
  • Dicarboxylic acid or polycarboxylic acid can also be used in the form of its ester-forming derivative.
  • the acid is used in the form of anhydride.
  • trimellitic anhydride (TMA) or 4-carboxyl phthalic anhydride can be used.
  • TMA trimellitic anhydride
  • 4-carboxyl phthalic anhydride can be used.
  • oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, trimellitic anhydride, or combination thereof can be given.
  • adipic acid, sebacic acid, trimellitic anhydride or combination thereof is used.
  • Suitable diols used herein include, neopentyl glycol, 1,6-hexylene glycol, 3- methyl-l,5-pentanediol, 1,4-cyclohexane dimethanol, 2,2,4-trimethyl-l,3-pentanediol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, hexaethylene glycol, propylene glycol, tripropylene glycol, or combination thereof.
  • neopentyl glycol, 1,6-hexylene glycol, triethylene glycol, tripropylene glycol, or a combination thereof is used. More preferably, triethylene glycol or tripropylene glycol is used.
  • the esterification reaction of dicarboxylic acid or polycarboxylic acid (or its ester- forming derivative) with diol can be effected under the conditions that are known in the art.
  • the esterification reaction can be effected by removing water under azeotropic distillation in the absence of any catalyst.
  • adipic acid is used as the dicarboxylic acid, and neopentyl glycol and 1,6-hexylene glycol are used as the diol.
  • the esterification reaction of adipic acid with neopentyl glycol and 1,6-hexylene glycol is effected by removing water under azeotropic distillation at an elevated temperature.
  • Adipic acid used as the dicarboxylic acid and neopentyl glycol and 1,6-hexylene glycol used as the diol are loaded, respectively, in such an amount that the molar equivalent ratio of the dicarboxylic acid to the diol is in the range of 1 : 1 to 1.2: 1 , in particular 1 : 1, thereby forming a hydroxyl compound containing a free carboxylic acid group.
  • each Pv 1 independently represents, at each occurrence, -(CH 2 )4-;
  • each R independently represents, at each occurrence, -CH 2 C(CH 3 ) 2 CH 2 - or -(CH 2 ) 6 -;
  • n is in the range of 0 to 100.
  • the reaction is carried out in a solvent of xylene in the absence of any catalyst at an elevated temperature up to 160 °C. Water is removed from the reaction system while the reaction is proceeding.
  • the phosphate ester dispersion promoting agent according to the present disclosure can be prepared by the process as disclosed herein.
  • the phosphate ester dispersion promoting agent as prepared can be applied directly to intended applications, such as formulation of stain or paint.
  • a dispersion of a particulate solid comprising the phosphate ester dispersion promoting agent as disclosed herein and use of the phosphate ester dispersion promoting agent for dispersing a particulate solid.
  • a dispersion of a particulate solid refers to a composition of matter obtained by dispersing a particulate solid in a dispersing medium with the aid of a dispersion promoting agent.
  • a dispersion of a particulate solid comprises a phosphate ester dispersion promoting agent as disclosed herein, a particulate solid, a dispersing medium, and optionally one or more additional additives.
  • the dispersion may comprise, relative to the total weight of the dispersion, 0.5 to 3.0% by weight, preferably 0.5 to 2.0 % by weight, more preferably 0.7 to 1.5 % by weight, and most preferably 0.8 to 1.0 % by weight, of the phosphate ester dispersion promoting agent.
  • particulate solid refers to any solid material which is substantially insoluble in a dispersion medium at the temperature concerned, and which it is desired to stabilize in a finely divided form in the dispersion medium.
  • the particulate solid may be in shape of sphere, fiber, flake, or other regular or irregular shapes of micrometric or even nanometric size.
  • Examples of a particulate solid comprise pigments and fillers, especially those pigments or fillers suitably used in a stain, paint or coating.
  • the particulate solid is selected from inorganic pigments comprising metal oxides such as titanium dioxide, iron oxides, zinc oxide, zirconia, or aluminia; metal composite oxides containing two or more metal elements including manganese, nickel, titanium, chromium, antimony, magnesium, cobalt, iron, or aluminum; oxymetallic compounds, such as bismuth vanadate, cobalt aluminate, cobalt zincate, or zinc chromate; metallic pigments, such as aluminum flake, copper, and copper-zinc alloys; and pearlescent pigments, such as lead carbonate and bismuth oxychloride.
  • metal oxides such as titanium dioxide, iron oxides, zinc oxide, zirconia, or aluminia
  • oxymetallic compounds such as bismuth vanadate, cobalt aluminate, cobalt zincate,
  • the particulate solid is selected from the group of inorganic fillers comprising calcium carbonate, calcium sulfate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulfate, barium carbonate, magnesium oxide, magnesium hydroxide, aluminum trihydrate, silica (including natural amorphous silica, natural crystalline silica, natural diatomaceous earth, precipitated silica, fumed silica and nano-silica), silicates (including talc, kaolin, wollastonite, mica, sericite, synthetic aluminum silicate), metal fibers, glass fibers, carbon black, and the like.
  • silica including natural amorphous silica, natural crystalline silica, natural diatomaceous earth, precipitated silica, fumed silica and nano-silica
  • silicates including talc, kaolin, wollastonite, mica, sericite, synthetic aluminum silicate
  • the particulate solid is titanium dioxide in the form of a powder.
  • the dispersion may comprise, relative to the total weight of the dispersion, 40 to 80 % by weight, preferably 50 to 80 % by weight, more preferably 55 to 70 % by weight, and most preferably 55 to 65 % by weight, of the particulate solid.
  • the term "dispersing medium” refers to a medium in which the particulate solid is dispersed.
  • the dispersing medium is a polar organic liquid or resin or a non-polar organic liquid.
  • Suitable examples of the polar organic liquid include, but are not limited to, dialkyl ketones, alkyl esters of alkanoic acid and alkanol, and the like.
  • dialkyl and cycloalkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone, di- isopropyl ketone, methyl isobutyl ketone, di-isobutyl ketone, methyl isoamyl ketone, methyl n-amyl ketone and cyclohexanone; alkyl esters, such as methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, ethyl formate, methyl propionate, methoxy propylacetate, and ethyl butyrate; glycols and glycol esters and ethers, such as ethylene glycol, 2-ethoxyethanol, 3-methoxypropylpropanol, 3-ethoxypropylpropanol, 2- butoxyethyl acetate, 3-methoxypropyl
  • a polar resin may also be used as the dispersing medium of the dispersion according to the present disclosure. Suitable examples thereof are those film-formation resins suitably used in inks, paints or coatings.
  • the specific examples of such resins include, among others, polyamides, such as VersamidTM and WolfamidTM; cellulose ethers, such as ethyl cellulose and ethyl hydroxyethyl cellulose; and alkyd resins, such as short oil alkyd resins and long oil alkyd resins.
  • non-polar, organic liquid examples include, among others, non- halogenated aromatic hydrocarbons, such as toluene and xylene; halogenated aromatic hydrocarbons, such as chlorobenzene, dichlorobenzene and trichlorobenzene; non- halogenated aliphatic hydrocarbons, such as those saturated or partially saturated, linear or branched hydrocarbons containing 6 or more carbon atoms; halogenated aliphatic hydrocarbons, such as dichloromethane, carbon tetrachloride, chloroform, trichloroethane; and natural non-polar organic liquids, such as vegetable oils, sunflower oil, linseed oil, terpene, and glyceride.
  • non- halogenated aromatic hydrocarbons such as toluene and xylene
  • halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene
  • a polar organic liquid or a polar resin is used as the dispersing medium.
  • the phosphate ester dispersion promoting agent according to the present disclosure will have good compatibility with the dispersing medium, thereby allowing the particulate solid to disperse in the dispersing medium even better.
  • the dispersion may comprise, relative to the total weight of the dispersion, 20 to 40 % by weight, preferably 25 to 35 % by weight, of the dispersing medium.
  • the dispersion of a particulate solid may further comprise one or more additional additives.
  • additional additives comprise surface active agents, antifoaming agents, rheology modifying agents, thermal stabilizers, flow/leveling agents, matting agents, anti-sedimentation agents, biocides, and combination thereof.
  • the amounts and types of additional additives desirably used can be determined empirically by a person skilled in the art.
  • the total amount of one or more additives is in the range of 0 to 10 % by weight relative to the total weight of the dispersion.
  • the dispersion of a particulate solid as disclosed herein can be used directly as such or can be used to formulate paints or coating compositions.
  • Hydroxyl Compound 2 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 1, except that 59.08 parts of 3-methyl-l,5-pentanediol was used to replace hexane glycol, and the reaction was stopped when the acid value arrived at about 59.1 mg KOH/g reaction mixture. Hydroxyl Compound 2 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 850 g/mol. Hydroxyl Compound 3
  • Hydroxyl Compound 3 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 1, except that 202.25 parts of sebacic acid were used to replace adipic acid, and the reaction was stopped when the acid value arrived about 69 mg KOH/g reaction mixture. Hydroxyl Compound 3 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 730 g/mol.
  • Hydroxyl Compound 6 was prepared according to the similar procedure for the preparation of Hydroxyl Compound 5, except that 300.48 parts of 12-hydroxystearic acid was used to replace ricinoleic acid, and the reaction was stopped when the acid value arrived about 45 mg KOH/g reaction mixture. Hydroxyl Compound 6 that contains a free carboxylic acid group was obtained. After calculation, its number-average molecular weight was determined to be about 1120 g/mol.
  • Phosphate Esters 2-10 were prepared according to the similar procedure for the preparation of Phosphate Ester 1, except that the hydroxyl compounds and the phosphating agents were used as listed in Table 1.
  • Phosphate ester dispersion promoting agents 2, 4, and 6 50 solids%) prepared in Example 1 were mixed with short oil alkyd resin (60 solids%), titanium dioxide powder and propylene glycol methoxy acetate (PGMA), respectively, in amounts as shown in Table 2, and were dispersed in Dispermat with glass beads for 1 hour, thus providing the dispersions of a particulate solid named Dispersion 2, Dispersion 4, and Dispersion 6. Additionally, the conventional phosphate ester dispersion promoting agent commercially available under the trade name BYK110 (50 solids%) was used to formulate a control dispersion with the ingredients according to Table 2.
  • PGMA propylene glycol methoxy acetate
  • Dispersions 2, 4, and 6 produced in Example 2 were mixed, as a stain, with short oil alkyd resin (60 solids%), butyl acetate, and the antifoaming agent, respectively, in amounts as shown in Table 3 in a high-speed disperser at 2000 rpm, thus providing the paints named Paint 2, Paint 4, and Paint 6. Additionally, the control dispersion was used to formulate a control paint with the ingredients according to Table 3.

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PCT/US2014/040605 2013-06-13 2014-06-03 Phosphate ester dispersion promoting agent and dispersion comprising the same WO2014200755A1 (en)

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CN201310233774.4A CN104231673B (zh) 2013-06-13 2013-06-13 磷酸酯分散助剂以及包含这种磷酸酯分散助剂的分散体

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