WO2014158661A1 - Coalescents pour compositions de revêtement à base aqueuse - Google Patents

Coalescents pour compositions de revêtement à base aqueuse Download PDF

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Publication number
WO2014158661A1
WO2014158661A1 PCT/US2014/019182 US2014019182W WO2014158661A1 WO 2014158661 A1 WO2014158661 A1 WO 2014158661A1 US 2014019182 W US2014019182 W US 2014019182W WO 2014158661 A1 WO2014158661 A1 WO 2014158661A1
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Prior art keywords
coating composition
aqueous coating
aqueous
coalescent
polymeric dispersion
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Ceased
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PCT/US2014/019182
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English (en)
Inventor
Shawn J. Maynard
Cynthia L. Rand
Molly I-Chin Busby
Felipe A. Donate
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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Publication of WO2014158661A1 publication Critical patent/WO2014158661A1/fr
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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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters

Definitions

  • This invention relates generally to coalescing agents and their use in aqueous based coatings. More specifically, the coalescing agents are alkoxylate compounds derived from propylene oxide.
  • Coalescents are typically added to coating compositions, for example waterborne paints or coatings, to facilitate the formation of a continuous polymeric, or binder, film as water evaporates from the composition. Without the addition of coalescents, polymer dispersions may not act as effective binders for pigments in the paint and adhesion to a substrate may be compromised. For many years, these coalescing aids have been relatively volatile solvents such as 2,2,4-trimethyl-l,3-pentanediol monoisobutyrate.
  • VOC emissions contribute to the creation of ozone, a main constituent of smog.
  • VOC regulations established by the US are established by the US
  • the problem addressed by this invention is the provision of low or zero VOC coalescents for use in aqueous based coating compositions, for example, decorative and protective coatings for various substrates.
  • alkoxylate compounds of formula I as described herein function as excellent coalescents for polymer dispersions, facilitating the formation of a continuous polymer, or binder, film from the dispersion as water evaporates.
  • the alkoxylates exhibit very low volatility and are therefore suitable for use in zero or low VOC coating compositions.
  • an aqueous coating composition comprising: an aqueous polymeric dispersion; and a coalescent that is an alkoxylate of formula I:
  • R is linear or branched Cg-Qo alkyl
  • PO is propyleneoxy
  • n is a number from 3 to 7.
  • an aqueous coating composition comprising: (a) a grind phase; and (b) a letdown phase including an aqueous polymeric dispersion and a coalescent, wherein the coalescent is an alkoxylate of formula I as described herein.
  • a method for forming a coating comprising: (a) forming the aqueous coating composition as described herein; (b) applying said aqueous coating composition to a substrate; and (c) drying, or allowing to dry, said applied aqueous coating composition.
  • numeric ranges for instance as in “from 2 to 10,” are inclusive of the numbers defining the range (e.g., 2 and 10).
  • coalescent is meant a material that facilitates the film formation of an aqueous polymeric dispersion, particularly an aqueous coating composition that includes a dispersion of polymer in an aqueous medium such as, for example, a polymer prepared by emulsion polymerization techniques.
  • An indication of facilitation of film formation is that the minimum film formation temperature ("MFFT") of the composition including the aqueous polymeric dispersion is measurably lowered by the addition of the coalescent.
  • MFFT minimum film formation temperature
  • the invention provides aqueous coating compositions containing an aqueous polymeric dispersion and an alkoxylate as a coalescent.
  • the alkoxylate is a compound of formula I:
  • R is linear or branched Cg-Qo alkyl
  • PO is propyleneoxy
  • n is a number from 3 to 7.
  • Formula I includes the variable "n.” This variable represent an average degrees of propoxylation in an oligomer distribution and is determined from the relative mole amounts of the alcohol and propylene oxide starting materials used in the synthesis of the alkoxylate.
  • n is from 4 to 6, alternatively n is 5.
  • R in the alkoxylate of formula I is branched Cg-Cio alkyl.
  • R is 2-ethylhexyl (CHsCHaCHaCHaCHCCHaC ⁇ CHa-).
  • R is 2-propylheptyl (CHsCHaCHaCHaCHaCHCCHaCHaCI ⁇ CHa-).
  • a preferred alkoxylate of formula I is 2EH-0-(PO)s-OH, wherein 2EH is 2- ethylhexyl.
  • Another preferred alkoxylate of formula I is 2PH-0-(PO)s-OH, wherein 2PH is 2-propylheptyl.
  • the alkoxylate of formula I (the coalescent) exhibits a maximum volatility loss, when heated at 110 °C for 1 hour, of 20 weight percent or less, alternatively 17 weight percent or less.
  • alkoxylates of formula I of the invention may be prepared by synthetic methods known to those skilled in the art.
  • a suitable alcohol or fatty acid alcohol is alkoxylated with propylene oxide.
  • Alkoxylation processes may, for instance, be carried out in the presence of acidic or alkaline catalysts, or by using metal cyanide catalysts.
  • Alkaline catalysts may include, for instance, hydroxides or alcoholates of sodium or potassium, including NaOH, KOH, sodium methoxide, potassium methoxide, sodium ethoxide and potassium ethoxide.
  • Base catalysts are normally used in a
  • concentration of from 0.05 percent to about 5 percent by weight, preferably about 0.1 percent to about 1 percent by weight based on starting material.
  • propylene oxide may, for instance, be carried out in an autoclave under pressures from about 10 psig to about 200 psig, preferably from about 60 to about 100 psig.
  • the temperature of alkoxylation may range from about 30 °C to about 200 °C, preferably from about 100 °C to about 160 °C.
  • the product is typically allowed to react until the residual oxide is less than about 10 ppm.
  • the residual catalyst may be left unneutralized, or neutralized with organic acids, such as acetic, propionic, or citric acid.
  • the product may be neutralized with inorganic acids, such as phosphoric acid or carbon dioxide.
  • Residual catalyst may also be removed using ion exchange or an adsorption media, such as diatomaceous earth.
  • the aqueous coating composition of the present invention includes an aqueous polymeric dispersion and from 0.1% to 40% by weight, based on the weight of aqueous polymeric dispersion solids, of the coalescent of formula I.
  • the MFFT of the aqueous polymeric dispersion is from -5°C to 100°C, from 0.1% to 30% coalescent, by weight based on the weight of aqueous polymeric dispersion solids, may be used.
  • the MFFT of the aqueous polymeric dispersion is from -20°C to 30°C, from 0.1% to 10 % coalescent, by weight based on the weight of aqueous polymeric dispersion solids, may be used.
  • MFFTs of the aqueous polymeric dispersions herein are those measured using ASTM D 2354 and films drawndown with a 5 mil drawdown bar. MFFT values are indicative of how efficient a coalescent is for a given aqueous polymeric dispersion; it is desirable to achieve the lowest possible MFFT with the smallest amount of coalescent.
  • the aqueous polymeric dispersion may be a dispersion of a polymer, oligomer, or prepolymer in an aqueous medium.
  • the aqueous polymeric dispersion may be reactive before, during, or subsequent to film formation.
  • aqueous medium is meant herein a medium including at least 50%, by weight based on the weight of the medium, water.
  • Typical aqueous polymeric dispersions are aqueous dispersions of epoxies, urethanes, acrylic polyols, polyesters, and hybrids of these and other chemistries; and emulsion polymers.
  • the emulsion polymer includes at least one addition copolymerized ethylenically unsaturated monomer such as, for example, styrene or substituted styrenes; vinyl toluene; butadiene; (meth)acrylonitrile; a (meth)acrylic ester monomer such as, for example, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, and ureido-functional (meth)acrylates; vinyl acetate or other vinyl esters; vinyl monomers such as vinyl chloride, vinylidene chloride, and N-vinyl pyrrolidone.
  • ethylenically unsaturated monomer such as, for example, styrene or substituted styrenes
  • vinyl toluene such as, for example, butadiene;
  • the emulsion polymer includes from 0% to 6%, or in the alternative, from 0% to 3 wt% or from 0% to 1%, by weight based on the weight of the polymer, of a copolymerized multi-ethylenically unsaturated monomer.
  • the level of multi- ethylenically unsaturated monomer should be selected so as to not materially interfere with film formation and integrity.
  • Multi-ethylenically unsaturated monomers include, for example, allyl (meth)acrylate, diallyl phthalate, 1,4-butylene glycol di(meth)acrylate, 1,2- ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, and divinyl benzene.
  • the emulsion polymer includes from 0% to 15%, preferably from 0.5% to 5%, of a copolymerized monoethylenically-unsaturated acid monomer, based on the weight of the polymer.
  • Acid monomers include carboxylic acid monomers such as, for example, (meth)acrylic acid, crotonic acid, itaconic acid, fumaric acid, maleic acid, monomethyl itaconate, monomethyl fumarate, monobutyl fumarate, maleic anhydride, 2-acrylamido-2- methylpropane sulfonic acid, vinyl sulfonic acid, styrene sulfonic acid, l-allyloxy-2- hydroxypropane sulfonic acid, alkyl allyl sulfosuccinic acid, sulfoethyl (meth)acrylate, phosphoalkyl (meth)acrylates such as phosphoethyl (meth)acrylate, phosphopropy
  • (meth)acrylate and phosphobutyl (meth)acrylate, phosphoalkyl crotonates, phosphoalkyl maleates, phosphoalkyl fumarates, phosphodialkyl (meth)acrylates, phosphodialkyl crotonates, and allyl phosphate.
  • the aqueous emulsion polymer is typically formed by an addition polymerization emulsion polymerization process as is known in the art.
  • Conventional surfactants and blends may be used including, for example, anionic and/or nonionic emulsifiers such as, for example, alkali metal or ammonium alkyl sulfates, alkyl sulfonic acids, fatty acids, and oxyethylated alkyl phenols, and mixtures thereof.
  • Polymerizable surfactants that include at least one ethylenically unsaturated carbon-carbon bond which can undergo free radical addition polymerization may be used.
  • the amount of surfactant used is usually 0.1% to 6% by weight, based on the weight of total monomer.
  • Either thermal or redox initiation processes may be used.
  • Conventional free radical initiators may be used such as, for example, hydrogen peroxide, t-butyl hydroperoxide, t-amyl hydroperoxide, ammonium and/or alkali persulfates, typically at a level of 0.01% to 3.0% by weight, based on the weight of total monomer.
  • Redox systems using the same initiators coupled with a suitable reductant such as, for example, sodium sulfoxylate formaldehyde, sodium hydrosulfite, isoascorbic acid, hydroxylamine sulfate and sodium bisulfite may be used at similar levels, optionally in combination with metal ions such as, for example iron and copper, optionally further including complexing agents for the metal.
  • Chain transfer agents such as mercaptans may be used to lower the molecular weight of the polymer.
  • the monomer mixture may be added neat or as an emulsion in water. The monomer mixture may be added in a single addition or more additions or continuously over the reaction period using a uniform or varying composition. Additional ingredients such as, for example, free radical initiators, oxidants, reducing agents, chain transfer agents, neutralizers, surfactants, and dispersants may be added prior to, during, or subsequent to the monomer addition.
  • the emulsion polymer may be formed in a multi-stage emulsion polymerization process as are well known in the art.
  • the emulsion polymer is also contemplated to be formed in two or more stages, the stages differing in molecular weight. Blending two different emulsion polymers is also contemplated.
  • the average particle diameter of the emulsion polymer particles is typically from 40 nm to 1000 nm, preferably from 40 nm to 300 nm. Particle diameters herein are those measured by dynamic light scattering on a Brookhaven BI-90 Plus particle size analyzer.
  • the aqueous coating composition of the invention is prepared by techniques which are well known in the coatings art. First, pigment(s), if any, are well dispersed in an aqueous medium under high shear such as is afforded by a Cowles mixer or predispersed colorant(s), or mixtures thereof are used. Then the emulsion polymer is added under low shear stirring along with the coalescent composition and other coatings adjuvants as desired.
  • the aqueous coating composition may include, in addition to the aqueous polymeric dispersion and optional pigment(s), conventional coatings adjuvants such as, for example, extenders, emulsifiers, coalescing agents other than the coalescent composition of the present invention, plasticizers, freeze-thaw stabilizers, curing agents, buffers, neutralizers, thickeners, rheology modifiers, humectants, wetting agents, biocides, antifoaming agents, UV absorbers, fluorescent brighteners, light or heat stabilizers, chelating agents, dispersants, colorants, waxes, and water-repellants.
  • conventional coatings adjuvants such as, for example, extenders, emulsifiers, coalescing agents other than the coalescent composition of the present invention, plasticizers, freeze-thaw stabilizers, curing agents, buffers, neutralizers, thickeners, rheology modifiers, humectants, wetting agents, biocides, anti
  • the coating composition may also contain surfactants, including for instance materials of the formula R 1 -(PO) x -(EO) y -H, where R 1 is linear or branched C6-C 12 alkyl, preferably branched C8-C 10 alkyl, and more preferably 2- ethylhexyl, PO is propyleneoxy, EO is ethyleneoxy, x is from 1 to 11, preferably from 4 to 6, and y is from 1 to 20, preferably from 3 to 11.
  • surfactants including for instance materials of the formula R 1 -(PO) x -(EO) y -H, where R 1 is linear or branched C6-C 12 alkyl, preferably branched C8-C 10 alkyl, and more preferably 2- ethylhexyl, PO is propyleneoxy, EO is ethyleneoxy, x is from 1 to 11, preferably from 4 to 6, and y is from 1 to 20, preferably from 3 to 11.
  • Suitable pigments and extenders include titanium dioxide such as anatase and rutile titanium dioxides; zinc oxide; antimony oxide; iron oxide; magnesium silicate; calcium carbonate; organic and inorganic colored pigments; aluminosilcates; silica; various clays such as kaolin and delaminated clay; and lead oxide. It is also contemplated that the aqueous coating composition may also contain opaque polymer particles, such as, for example, ROPAQUETM Opaque Polymers (Ropaque is a trademark of Rohm and Haas Company).
  • encapsulated or partially encapsulated opacifying pigment particles and polymers or polymer emulsions adsorbing or bonding to the surface of pigments such as titanium dioxide; and hollow pigments, including pigments having one or more voids.
  • Titanium dioxide is the main pigment used to achieve hiding in architectural paints. This pigment is expensive and in short supply.
  • One way to achieve hiding while decreasing the amount of Ti0 2 is to include multistage emulsion polymers that add opacity to the paint film, commonly known as "opaque polymers.” These polymers are water- filled emulsion polymer particles (mostly styrene) with a high Tg. These particles fill with air during film formation and scatter light creating opacity.
  • an aqueous coating composition including an opaque polymer will also include an aqueous polymeric dispersion; desirably a coalescent will facilitate film formation of the aqueous polymeric dispersion, but not cause the opaque polymer to collapse.
  • coalescents attack the opaque polymer causing the particles to collapse which results in less light scattering and decreased opacity.
  • TEXANOLTM TEXANOL is a trademark of Eastman Chemical Company
  • OPTIFILMTM 400 OPTIFILM is a trademark of Eastman Chemical Company
  • Coalescents of the invention may be useful in their ability to preserve the opacity provided by certain commercial ROPAQUETM opaque polymers.
  • the amounts of pigment and extender in the aqueous coating composition vary from a pigment volume concentration (PVC) of 0 to 85 and thereby encompass coatings otherwise described in the art, for example, as clear coatings, stains, flat coatings, satin coatings, semi-gloss coatings, gloss coatings, primers, textured coatings, and the like.
  • PVC pigment volume concentration
  • the aqueous coating composition herein expressly includes architectural, maintenance, and industrial coatings, caulks, sealants, and adhesives.
  • the pigment volume concentration is calculated by the following formula:
  • PVC (%) volume of pigment(s), + volume extender(s) x 100.
  • the solids content of the aqueous coating composition may be from 10% to 70% by volume.
  • the viscosity of the aqueous coating composition may be from 50 centipoises to
  • composition is typically applied to a substrate such as, for example, wood, metal, plastics, marine and civil engineering substrates, cementitious substrates such as, for example, concrete, stucco, and mortar, previously painted or primed surfaces, and weathered surfaces.
  • a substrate such as, for example, wood, metal, plastics, marine and civil engineering substrates, cementitious substrates such as, for example, concrete, stucco, and mortar, previously painted or primed surfaces, and weathered surfaces.
  • the aqueous coating composition may be applied to a substrate using conventional coatings application methods such as, for example, brush, roller, caulking applicator, roll coating, gravure roll, curtain coater and spraying methods such as, for example, air-atomized spray, air-assisted spray, airless spray, high volume low pressure spray, and air-assisted airless spray.
  • conventional coatings application methods such as, for example, brush, roller, caulking applicator, roll coating, gravure roll, curtain coater and spraying methods such as, for example, air-atomized spray, air-assisted spray, airless spray, high volume low pressure spray, and air-assisted airless spray.
  • Drying of the aqueous coating composition to provide a coating may be allowed to proceed under ambient conditions such as, for example, at 5 °C to 35 °C. or the coating may be dried at elevated temperatures such as, for example, from 35 °C to 150 °C.
  • Propoxylation of 2-ethylhexanol is performed in a jacketed, autoclave reactor.
  • Solid double metal cyanide catalyst (DMC, 0.48 g) is charged with 2-ethylhexanol (1850.90 g). The mixture is heated to 130 °C.
  • Propylene oxide (PO, 4171.90 g) is added to the 2- ethylhexanol-DMC mixture over 8 hours 16 minutes, during which the temperature is kept at 130 °C. The mixture is kept at 130 °C for 14 h before being cooled back to room temperature.
  • the VOC content of 2 ⁇ -0- ⁇ 0 5 - ⁇ is determined by using the test conditions under EPA Method 24 for establishing volatility.
  • the test involves measuring the sample mass loss after heating. General procedure: the sample being tested is placed in three pre- weighed aluminum pans at room temperature. Sample mass in each pan is recorded. The samples are heated in a force flow oven at 110 °C for 1 hour. Samples are cooled back to room temperature. The pans are weighed again to determine the mass change after heating.
  • the VOC and percent VOC content is defined as follow:
  • VOC Original sample mass— sample mass after heating
  • the data shows an average VOC content for 2 ⁇ -0- ⁇ 0 5 - ⁇ of 15.2%.
  • the comparative material TEXANOLTM is 100 % VOC under the same EPA Method 24 test conditions.
  • the coalescing performance of 2 ⁇ -0- ⁇ 0 5 - ⁇ for latex binder is evaluated by determining the minimum film formation temperature (MFFT).
  • RHOPLEXTM SG10M - Binder an acrylic emulsion polymer.
  • RHOPLEX is a trademark of Rohm and Haas Company.
  • RHOPLEXTM SG30 - Binder an acrylic emulsion polymer
  • TEXANOLTM (2,2,4-trimethyl-l,3-pentanediol monoisobutyrate) - a comparative coalescing agent.
  • Sample B - 2 ⁇ -0- ⁇ 0 5 - ⁇ prepared using the procedure described in example 1, catalyzed by KOH.
  • Coalescent agent is mixed with a latex binder at the proportion specified in Table 1 below.
  • the mixture is coated on a six pieces of Scotch MagicTM tape (1 inch x 24 inch) that are warmed with a uniform temperature gradient of 30-53 °F.
  • One end of the tape is 30 °F, the other end of the tape is 53 °F.
  • the temperature at which the first sign of cracking could be observed on the tape is recorded. This temperature is the minimum film formation temperature (MFFT).
  • MFFT minimum film formation temperature
  • the average MFFT value is reported based on the readings for the six replicates. A compound that provides a lower MFFT value to a binder indicates a better coalescing aid.
  • inventive coalescents As shown in the Table 1, inventive coalescents, Sample A and Sample B, performed similarly to the comparative material, TEXANOLTM.
  • inventive coalescents are low VOC.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des compositions aqueuses de revêtement comprenant une dispersion polymère aqueuse et un coalescent, ledit coalescent étant un alcoxylat. L'invention concerne également des procédés permettant de former des revêtements à partir de compositions aqueuses de revêtement.
PCT/US2014/019182 2013-03-14 2014-02-28 Coalescents pour compositions de revêtement à base aqueuse Ceased WO2014158661A1 (fr)

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US201361782430P 2013-03-14 2013-03-14
US61/782,430 2013-03-14

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021081732A1 (fr) * 2019-10-29 2021-05-06 Dow Global Technologies Llc Composition de polyuréthane à deux composants
US11834587B2 (en) 2018-10-16 2023-12-05 Dow Global Technologies Llc Aqueous coating compositions
US11939486B2 (en) 2018-10-16 2024-03-26 Dow Global Technologies Llc Aqueous dispersion of polymeric particles
EP4511429A4 (fr) * 2022-05-17 2026-03-04 Dow Global Technologies Llc Compositions de revêtement aqueuses

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US4384056A (en) 1980-05-08 1983-05-17 Bayer Aktiengesellschaft Aqueous dispersions based on (meth)acrylic acid alkyl ester polymers with two pronounced, substantially non-overlapping peaks in the particle size distribution within specific particle size ranges, and a process for the preparation and use thereof
US4539361A (en) 1983-05-27 1985-09-03 Rohm Gmbh Method for making polymodal aqueous synthetic resin dispersions
WO2006115550A1 (fr) * 2005-04-22 2006-11-02 Basf Aktiengesellschaft Compositions de revetement d’emulsion polymere ayant un faible cov
WO2008063829A1 (fr) * 2006-11-21 2008-05-29 Basf Se Composition de revêtement présentant une faible teneur en composés organiques volatils
EP2186863A1 (fr) * 2008-11-15 2010-05-19 Cognis IP Management GmbH Utilisation des produits de la fixation par addition d'oxyde d'éthylène (EO) et/ou d'oxyde de propylène (PO) sur des alcools gras comportant 8 à 22 atomes de carbone, comme agent de coalescence
EP2399960A2 (fr) * 2010-06-25 2011-12-28 Dow Global Technologies LLC Agent de coalescence pour compositions aqueuses
WO2012054317A1 (fr) * 2010-10-21 2012-04-26 Eastman Chemical Company Compositions de revêtement à l'eau contenant des coalescents à faible teneur de cov qui sont des esters d'hydroxypivalate d'hydroxypivalyle
WO2013165618A1 (fr) * 2012-04-30 2013-11-07 Dow Global Technologies Llc Agents de coalescence à base d'éther de glycol et à faible teneur en composés organiques volatils pour revêtements à base aqueuse

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384056A (en) 1980-05-08 1983-05-17 Bayer Aktiengesellschaft Aqueous dispersions based on (meth)acrylic acid alkyl ester polymers with two pronounced, substantially non-overlapping peaks in the particle size distribution within specific particle size ranges, and a process for the preparation and use thereof
US4539361A (en) 1983-05-27 1985-09-03 Rohm Gmbh Method for making polymodal aqueous synthetic resin dispersions
WO2006115550A1 (fr) * 2005-04-22 2006-11-02 Basf Aktiengesellschaft Compositions de revetement d’emulsion polymere ayant un faible cov
WO2008063829A1 (fr) * 2006-11-21 2008-05-29 Basf Se Composition de revêtement présentant une faible teneur en composés organiques volatils
EP2186863A1 (fr) * 2008-11-15 2010-05-19 Cognis IP Management GmbH Utilisation des produits de la fixation par addition d'oxyde d'éthylène (EO) et/ou d'oxyde de propylène (PO) sur des alcools gras comportant 8 à 22 atomes de carbone, comme agent de coalescence
EP2399960A2 (fr) * 2010-06-25 2011-12-28 Dow Global Technologies LLC Agent de coalescence pour compositions aqueuses
WO2012054317A1 (fr) * 2010-10-21 2012-04-26 Eastman Chemical Company Compositions de revêtement à l'eau contenant des coalescents à faible teneur de cov qui sont des esters d'hydroxypivalate d'hydroxypivalyle
WO2013165618A1 (fr) * 2012-04-30 2013-11-07 Dow Global Technologies Llc Agents de coalescence à base d'éther de glycol et à faible teneur en composés organiques volatils pour revêtements à base aqueuse

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11834587B2 (en) 2018-10-16 2023-12-05 Dow Global Technologies Llc Aqueous coating compositions
US11939486B2 (en) 2018-10-16 2024-03-26 Dow Global Technologies Llc Aqueous dispersion of polymeric particles
WO2021081732A1 (fr) * 2019-10-29 2021-05-06 Dow Global Technologies Llc Composition de polyuréthane à deux composants
US12365755B2 (en) 2019-10-29 2025-07-22 Dow Global Technologies Llc Two-component polyurethane composition
EP4511429A4 (fr) * 2022-05-17 2026-03-04 Dow Global Technologies Llc Compositions de revêtement aqueuses

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