US20100126384A1 - Use of Esters as Coalescing Agent - Google Patents

Use of Esters as Coalescing Agent Download PDF

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Publication number
US20100126384A1
US20100126384A1 US12/598,505 US59850508A US2010126384A1 US 20100126384 A1 US20100126384 A1 US 20100126384A1 US 59850508 A US59850508 A US 59850508A US 2010126384 A1 US2010126384 A1 US 2010126384A1
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Prior art keywords
esters
composition according
acid
coalescent
coalescents
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Abandoned
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US12/598,505
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English (en)
Inventor
Peter Bene
Harald Frommelius
Heinz-Günther Schulte
Annemarie Meinhold
Edda Bergmann
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Publication of US20100126384A1 publication Critical patent/US20100126384A1/en
Assigned to COGNIS IP MANAGEMENT GMBH reassignment COGNIS IP MANAGEMENT GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SCHULTE, HEINZ-GUNTHER, BENE, PETER, BERGMANN, EDDA, FROMMELIUS, HARALD, MEINHOLD, ANNEMARIE
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • 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
    • C09D7/63—Additives non-macromolecular organic
    • 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
    • C09D125/00—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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/04—Homopolymers or copolymers of styrene
    • C09D125/08—Copolymers of styrene
    • C09D125/14—Copolymers of styrene with unsaturated 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
    • 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
    • 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
    • C09D133/10—Homopolymers or copolymers of methacrylic 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • 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
    • C09D7/47—Levelling agents
    • 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
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids

Definitions

  • the invention relates to the use of esters of the general formula R 1 —COOR 2 , in which R 1 is an alkyl radical having 9 to 23 C atoms and R 2 is a saturated alkyl radical selected from the group of methyl, ethyl, n-propyl, and isopropyl, as coalescents, in particular for the preparation of coating materials.
  • Coalescents also called film-forming assistants
  • They are added to aqueous coating materials and bring about filming of the dispersed polymer particles to form a homogeneous coating film. Adding them is required when the film-forming temperature of the binder is above the temperature of the application.
  • Known film-forming assistants include the following: ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol butyl ether, ethylene glycol hexyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, diethylene glycol hexyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol phenyl ether, propylene glycol tert-butyl ether, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, and 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (compare “Farbe+Lack”, 101 (July 1995), pp. 606-609).
  • coalescents In recent times, for environmental reasons, water-based coatings have become very topical.
  • latex coatings based in particular on small particles of synthetic polymers such as polyacrylates, coalescents have traditionally been used in substantial quantities. These coalescents (also called filming assistants) are added to the coatings in order to improve film formation.
  • the function derives from the plasticizing effect exerted by the coalescent on the latex particles, enabling them to coalesce and form a continuous film.
  • This film has optimum properties after the evaporation of the water.
  • Important in the formation of a film is the temperature known as the film-forming temperature, at which (or below which) the polymer particles coalesce to form a film.
  • the customary coalescents lower the film-forming temperature of the polymer.
  • coalescents are certain esters and ethers; known technical standards are the hydroxyl ester “Texanol” from Eastman (also often called TMB; a 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate), and also “EGBE” from Union Carbide (ethylene glycol monobutyl ether).
  • Coalescents for coatings that are disclosed therein are adducts of EO and PO with aromatic carboxylic acids such as benzoic acid.
  • EP 069,839 B1 claims the use of hydroxyl ester mixtures as flow control assistants for aqueous polymer dispersions.
  • the compounds are those obtainable by reacting propylene oxide with aliphatic C 7-12 monocarboxylic acids.
  • acetoacetates can be used as a reactive coalescent.
  • US 2005/0182168 A1 discloses a combination of glycol esters of vegetable oil-based fatty acids and antioxidants. Propylene glycol monoesters are a specific topic therein.
  • WO 00/56823 discloses film-forming compositions having an aqueous phase and a dispersed phase, the latter comprising a polymer and a coalescent.
  • the latter is an ester subject to the structural proviso that the acid component and/or the alcohol component must comprise at least two C ⁇ C double bonds.
  • the technical purpose of this multiplicity of double bonds is that the coalescent itself is reactively crosslinked; it is referred to as a reactive coalescent.
  • Claim 1 of U.S. Pat. No. 6,762,230 B2 is directed to coating compositions comprising a latex polymer and a coalescent of the formula R 1 —(CO—X r —O) n —R 2 .
  • R 1 is an organic group
  • X is a divalent organic group
  • the index r can be 0 or 1
  • the index n can be in the range from 1 to 10
  • R 2 is hydrogen or an organic group.
  • r adopts a value of 0 and n a value of 1
  • the radicals R 1 and R 2 are alkyl radicals
  • the stated formula circumscribes fatty acid esters. It is pointed out, however, that fatty acid esters are not specifically disclosed in U.S. Pat. No. 6,762,230 B2. Instead, the coalescents of U.S. Pat. No. 6,762,230 B2 that are specifically discussed are not fatty acid esters.
  • Fatty acid alkyl esters are referred to in the two following texts: in EP 026,982 A1 from 1980, aqueous coating compositions with a polymer and a coalescent are claimed. The latter is to be selected from a trio of “kinds” of esters; one of these kinds is characterized by the formula R 1 —COOR 2 .
  • R 1 is an alkyl or aryl group and R 2 is an alkyl group (bar methyl).
  • R 1 ⁇ C 3-7 and R 2 ⁇ C 4-8 both radicals aliphatic.
  • esters of straight-chain C 2-6 fatty acids the alcohol component of the esters being aliphatic C 3-4 alcohols, as solvents for coating materials. There is no reference there to coalescents.
  • coalescents There is a constant need for new coalescents.
  • the object of the present invention was therefore to provide coalescents.
  • These coalescents ought to be suitable in particular for producing coatings such as paints, inks, and the like, but also for adhesives.
  • a particularly preferred field for the use of the coalescents to be provided is that of the emulsion paints.
  • coalescents in the literature also called filming assistants or film-forming assistants
  • filming assistants in the literature also called filming assistants or film-forming assistants
  • coalescents to be developed in accordance with the invention are intended particularly for use in aqueous dispersions of polymers or latex particles that are suitable for coating purposes of any kind (for example, for water-based paints and inks).
  • Dispersions of this kind which are prepared typically by emulsion polymerization and which—in addition to water, the auxiliaries used in emulsion polymerization, and the particles of polymer or of latex—may comprise further constituents which are commonly used for the particular desired coating purpose, are customarily applied to the surface to be coated; this is followed by evaporation of the water, and, finally, it is essential that the polymer particles or latex particles merge by flowing and form a homogeneous film.
  • This process of film formation requires that at least a minimum temperature be observed, which is referred to by the skilled person as the minimum film-forming temperature (MFFT). Where the MFFT of a system is, for example, 20° C., this means that film formation proceeds successfully only when the temperature is 20° C.
  • MFFT minimum film-forming temperature
  • aqueous dispersions must be admixed with a coalescent in an amount such that the MFFT is lowered to the desired level.
  • the present invention has made it a goal in particular to develop coalescents which lower as effectively as possible the MFFT of aqueous dispersions of polymer particles or latex particles that are intended for any coating purposes.
  • the radical R 1 may be linear or branched, saturated or monoolefinically unsaturated.
  • the radical R 1 is a saturated alkyl radical.
  • esters of the formula (I) are suitable for producing coatings such as paints, inks, and the like, but also for adhesives.
  • esters of the formula (I) are used as coalescents in the production of coatings of any kind based on aqueous polymer dispersions or latex dispersions.
  • esters (I) as coalescents is that of (water-based) emulsion paints.
  • esters (I) examples include:
  • esters (I) derive preferably from fatty acids having 10 to 18 C atoms. These acids may be linear or branched, saturated or monoolefinically unsaturated. Fatty acids of natural origin are preferred.
  • esters (I) derive from linear, monoolefinically unsaturated fatty acids.
  • esters (I) derive from branched, saturated fatty acids.
  • esters (I) derive from linear, saturated fatty acids.
  • esters (I) used in the context of the present invention are methyl esters, in other words compounds characterized by the general formula (I-a)
  • R 1 is a saturated alkyl radical having 9 to 18 C atoms.
  • R 1 is a saturated alkyl radical having 9 to 18 C atoms.
  • methyl laurate, methyl myristate, and methyl palmitate, or mixtures thereof are especially preferred.
  • esters (I) used in the context of the present invention are isopropyl esters, in other words compounds characterized by the general formula (I-b)
  • R 1 is a saturated alkyl radical having 9 to 18 C atoms.
  • isopropyl laurate isopropyl myristate, and isopropyl palmitate, or mixtures thereof, are especially preferred.
  • esters (I) are very efficient as coalescents, as is apparent from their outstanding capacity to lower the minimum film-forming temperature (MFFT) of aqueous polymer dispersions. Moreover, coatings (films) obtainable using aqueous polymer dispersions comprising the ester (I) for use in accordance with the invention, after four weeks of storage, are in general significantly harder, and hence more robust and less susceptible to soiling, than those produced using commercial coalescents.
  • a further advantage of the esters (I) for use in accordance with the invention is that their boiling point is above 250° C., which is classified, in accordance with the EU regulations 1999/42/EC and 2004/42, as “VOC-free”.
  • esters (I) of the invention are also of interest.
  • the applicant has found that, in an aqueous-alkaline medium, methyl laurate and isopropyl laurate have a lower tendency toward hydrolysis than butyl laurate and the commercial 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate (TMB).
  • TMB 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate
  • esters (I) for use in accordance with the invention can be used in pure form or in the form of mixtures with one another. If desired, the esters (I) can also be used in combination with known coalescents.
  • compositions comprising
  • esters (I) for use in accordance with the invention are employed in particular as coalescents for aqueous dispersions of polymer particles or latex particles that are to be filmed. This is the case when the esters (I) are used either alone (in the form of a pure species or a mixture of different species) or in a blend with other coalescents different from them.
  • esters (I) are used in this case preferably (in accordance with the MFFT of the polymer) in amounts of 0.1% to 40% by weight and more particularly 2% to 6% by weight, based on the amount of the polymer particles or latex particles whose minimum film-forming temperature is to be lowered.
  • the amount of the esters (I) may be based on a completed coating formula which is to be applied to a surface.
  • the esters (I) are used preferably (in accordance with the MFFT of the polymer) in amounts of 0.1% to 5% by weight and more particularly 0.5% to 2% by weight, based on the overall coating formula.
  • the skilled person is able to vary the amount of the esters (I) in accordance with the composition of a specific dispersion or of a specific coating formula, and is able, as and when necessary, to use higher amounts of esters (I), particularly if the system comprises polymers with a high minimum film-forming temperature and/or if the MFFT is to be lowered to very low levels.
  • the aqueous dispersions may, moreover, comprise further adjuvants and additives that are known in this connection to the skilled person.
  • esters (I) of the invention may be added to the aqueous dispersions immediately after preparation, which is preferably by emulsion polymerization, or else at a later point in time, such as during the preparation of a coating material, for instance.
  • aqueous dispersions comprising ester (I) for use in accordance with the invention may be applied in principle to any desired surfaces, as for example to wood, metal, plastic, glass, paper, concrete, masonry, and renders.
  • Mowilith LDM 7451 Aqueous polymer dispersion based on acrylic ester/methacrylic ester/ styrene (Celanese) Mowilith LDM 7717 Aqueous polymer dispersion based on acrylic ester/methacrylic ester (Celanese) Acronal 290D Aqueous polymer dispersion based on butyl acrylate/styrene (BASF) Acronal S 790 Aqueous polymer dispersion based on butyl acrylate/styrene (BASF) Lipaton AE 4620 Aqueous polymer dispersion based on styrene/acrylic ester (Polymer Latex) Mowilith DM 611 Aqueous polymer dispersion based on styrene/acrylic ester (Celanese) Mowilith DM 2452 Aqueous polymer dispersion based on VAC/VEOVA/acrylic ester (Celane
  • test coalescent (B1 or V1) was made with stirring. After an aging time of 24 hours, the systems were applied to glass plates by doctor blade (wet film thickness 150 ⁇ m). After drying had taken place (at 20° C. for about 24 hours), the films were assessed, using a variety of test methods.
  • Pendulum hardness pendulum hardness measured after 4 weeks (with addition of B1 or V1 in an amount such as to lower the minimum film-forming temperature of the resin used to a value of 0° C.)
  • % B1 or V1 the amount of coalescent added to the aqueous polymer dispersion is reported in % by weight, based on the polymer dispersions (in the form as supplied by the manufacturer).
  • the inventive ester B1 has advantages in a number of respects over one of the industrial standards, namely V1:

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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)
  • Dispersion Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US12/598,505 2007-05-03 2008-04-24 Use of Esters as Coalescing Agent Abandoned US20100126384A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102007021139.4 2007-05-03
DE102007021139A DE102007021139A1 (de) 2007-05-03 2007-05-03 Verwendung von Estern als Koaleszenzmittel
PCT/EP2008/003294 WO2008135170A1 (de) 2007-05-03 2008-04-24 Verwendung von estern als koaleszenzmittel

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/003294 A-371-Of-International WO2008135170A1 (de) 2007-05-03 2008-04-24 Verwendung von estern als koaleszenzmittel

Related Child Applications (1)

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US15/230,126 Continuation US10533108B2 (en) 2007-05-03 2016-08-05 Use of Esters as Coalescing Agent

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US20100126384A1 true US20100126384A1 (en) 2010-05-27

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Application Number Title Priority Date Filing Date
US12/598,505 Abandoned US20100126384A1 (en) 2007-05-03 2008-04-24 Use of Esters as Coalescing Agent
US15/230,126 Active US10533108B2 (en) 2007-05-03 2016-08-05 Use of Esters as Coalescing Agent
US16/741,183 Abandoned US20200231835A1 (en) 2007-05-03 2020-01-13 Use of Esters as Coalescing Agent

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Application Number Title Priority Date Filing Date
US15/230,126 Active US10533108B2 (en) 2007-05-03 2016-08-05 Use of Esters as Coalescing Agent
US16/741,183 Abandoned US20200231835A1 (en) 2007-05-03 2020-01-13 Use of Esters as Coalescing Agent

Country Status (8)

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US (3) US20100126384A1 (enExample)
EP (1) EP2142606B1 (enExample)
JP (1) JP5487098B2 (enExample)
CN (1) CN101675124B (enExample)
AT (1) ATE531769T1 (enExample)
DE (1) DE102007021139A1 (enExample)
ES (1) ES2376605T3 (enExample)
WO (1) WO2008135170A1 (enExample)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012159180A1 (pt) * 2011-05-26 2012-11-29 Oxiteno S.A. Indústria E Comércio Composição de coalescentes verdes contendo monoésteres de ácidos graxos de óleos vegetais com álcoois do óleo fúsel
WO2012159181A1 (pt) * 2011-05-26 2012-11-29 Oxiteno S.A. Indústria E Comércio Composição de agentes de coalescência verdes contendo misturas de monoésteres e diésteres
JP2014500902A (ja) * 2010-11-25 2014-01-16 コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 合体剤としてのエステルの使用
US20150240106A1 (en) * 2014-02-26 2015-08-27 Elevance Renewable Sciences, Inc. Low-VOC Compositions and Methods of Making and Using the Same
US11840636B2 (en) 2019-08-02 2023-12-12 Bmic Llc Water-resistant acrylic coatings

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2186863A1 (de) * 2008-11-15 2010-05-19 Cognis IP Management GmbH Verwendung von Anlagerungsprodukten von Ethylen- und/oder Propylenoxid an Fettalkohole als Koaleszenzmittel
JP5737776B2 (ja) * 2010-02-10 2015-06-17 関西ペイント株式会社 エマルション樹脂系塗料
CA2743794C (en) * 2010-06-25 2013-09-10 Dow Global Technologies Llc Coalescent for aqueous compositions
CA2747190A1 (en) * 2010-08-30 2012-02-29 Dow Global Technologies Llc Coalescent for aqueous compositions
CN103153635B (zh) * 2010-10-25 2015-04-29 惠普发展公司，有限责任合伙企业 包含胶乳油墨成膜助剂的印刷介质
DE202014010355U1 (de) 2014-11-13 2015-05-06 Clariant International Ltd. VOC-arme Koaleszensmittel für wässrige Dispersionen
WO2019174021A1 (en) * 2018-03-16 2019-09-19 Dow Global Technologies Llc Aqueous coating compositions and methods for improving freeze/thaw stability of aqueous coating compositions
US20240132728A1 (en) * 2020-12-14 2024-04-25 Battelle Memorial Institute Bio-Based Coalescing Solvents
US12398312B2 (en) 2024-01-03 2025-08-26 Baker Hughes Oilfield Operations Llc Additive to reduce polymer solids deposition at pump head

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399158A (en) * 1964-04-02 1968-08-27 Distillers Co Yeast Ltd Coalescing agents for emulsion paints
US4043984A (en) * 1974-09-12 1977-08-23 Cassella Farbwerke Mainkur Aktiengesellschaft Aminoplasts elasticized with benzoic acid esters
US4141864A (en) * 1974-03-15 1979-02-27 University Of Virginia Alumni Patents Foundation Osseous cement composition
US4489188A (en) * 1982-07-02 1984-12-18 Eastman Kodak Company Coalescent-containing coating composition
US4894406A (en) * 1988-08-19 1990-01-16 Eastman Kodak Company Low odor coalescing aid for latex paints
US5756569A (en) * 1996-12-19 1998-05-26 Carver; Bobby Carroll Use of alkyl 3-alkoxypropionates as coalescing agents in aqueous coating compositions
US6762230B2 (en) * 2001-02-22 2004-07-13 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
US20050182168A1 (en) * 2004-01-16 2005-08-18 Archer-Daniels-Midland Company Stabilized ester compositions and their use in film-forming compositions
US7160945B1 (en) * 1999-03-22 2007-01-09 The Curators Of The University Of Missouri Water borne film-forming compositions

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT331942B (de) 1973-10-22 1976-08-25 Erz & Stahl Ges M B H Losungsmittel fur lacke
EP0026982A1 (en) 1979-09-07 1981-04-15 Rohm And Haas Company Coating compositions containing mono- or diester coalescing agents and a substrate coated therewith
ZA805482B (en) * 1979-09-07 1981-09-30 Rohm & Haas Coating compositions containing mono- or di-ester coalescents
DE3109580A1 (de) * 1981-03-13 1982-10-28 Bayer Ag, 5090 Leverkusen Waessrige dispersionen auf basis von cellulosenitraten, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von ueberzuegen
DE3127277A1 (de) 1981-07-10 1983-01-27 Chemische Werke Hüls AG, 4370 Marl Verfilmungshilfsmittel fuer filmbildende, waessrige kunststoffdispersionen
GB9103649D0 (en) 1991-02-21 1991-04-10 Bp Chem Int Ltd Coalescing aids
US5349026A (en) * 1992-11-20 1994-09-20 Rohm And Haas Company Reactive coalescents
US5868819A (en) * 1996-05-20 1999-02-09 Metal Coatings International Inc. Water-reducible coating composition for providing corrosion protection
EP1169397B1 (en) 1999-03-22 2003-07-23 The Curators Of The University Of Missouri Water borne film-forming compositions
WO2004090005A1 (en) * 2003-04-03 2004-10-21 Vocfree, Inc. Voc free latex coalescent systems

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399158A (en) * 1964-04-02 1968-08-27 Distillers Co Yeast Ltd Coalescing agents for emulsion paints
US4141864A (en) * 1974-03-15 1979-02-27 University Of Virginia Alumni Patents Foundation Osseous cement composition
US4043984A (en) * 1974-09-12 1977-08-23 Cassella Farbwerke Mainkur Aktiengesellschaft Aminoplasts elasticized with benzoic acid esters
US4489188A (en) * 1982-07-02 1984-12-18 Eastman Kodak Company Coalescent-containing coating composition
US4894406A (en) * 1988-08-19 1990-01-16 Eastman Kodak Company Low odor coalescing aid for latex paints
US5756569A (en) * 1996-12-19 1998-05-26 Carver; Bobby Carroll Use of alkyl 3-alkoxypropionates as coalescing agents in aqueous coating compositions
US7160945B1 (en) * 1999-03-22 2007-01-09 The Curators Of The University Of Missouri Water borne film-forming compositions
US20070093579A1 (en) * 1999-03-22 2007-04-26 The Curators Of The University Of Missouri Water Borne Film-Forming Compositions
US6762230B2 (en) * 2001-02-22 2004-07-13 Valspar Sourcing, Inc. Coating compositions containing low VOC compounds
US20050182168A1 (en) * 2004-01-16 2005-08-18 Archer-Daniels-Midland Company Stabilized ester compositions and their use in film-forming compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bonhorst et al, "Ester of Naturally Occuring Fatty Acids", INDUSTRIAL ENGINEERING AND CHEMISTRY, (Dec. 1948), pp 2379-2384 *

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US9926430B2 (en) 2011-05-26 2018-03-27 Oxiteno S.A. Industria E Comercio Green coalescent agent composition containing mixtures of monoesters and diesters
WO2012159181A1 (pt) * 2011-05-26 2012-11-29 Oxiteno S.A. Indústria E Comércio Composição de agentes de coalescência verdes contendo misturas de monoésteres e diésteres
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US10184041B2 (en) * 2011-05-26 2019-01-22 Oxiteno S.A. Industria E Comercio Green coalescent agent composition containing fatty acid monoesters of vegetable oils with fusel oil alcohols
US20150240106A1 (en) * 2014-02-26 2015-08-27 Elevance Renewable Sciences, Inc. Low-VOC Compositions and Methods of Making and Using the Same
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US10233347B2 (en) * 2014-02-26 2019-03-19 Elevance Renewable Sciences, Inc. Low-VOC compositions and methods of making and using the same
US10669443B2 (en) * 2014-02-26 2020-06-02 Elevance Renewable Sciences, Inc. Low-VOC compositions and methods of making and using the same
US11840636B2 (en) 2019-08-02 2023-12-12 Bmic Llc Water-resistant acrylic coatings

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US20200231835A1 (en) 2020-07-23
CN101675124A (zh) 2010-03-17
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JP5487098B2 (ja) 2014-05-07
EP2142606B1 (de) 2011-11-02
CN101675124B (zh) 2012-12-12
DE102007021139A1 (de) 2008-11-06
US10533108B2 (en) 2020-01-14
EP2142606A1 (de) 2010-01-13
ES2376605T3 (es) 2012-03-15
WO2008135170A1 (de) 2008-11-13
US20170015846A1 (en) 2017-01-19

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