Antifoaming agent and its composition, process for preparing and method of use thereof

Abstract

The present invention provides an antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s). The present invention also provides a process for preparing the antifoaming agent and compositions in coatings. The antifoaming agent of the present invention is a glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester.

Description

Docket No.: HER 12231PCT ANTIFOAMING AGENT AND ITS COMPOSITION, PROCESS FOR PREPARING AND METHOD OF USE THEREOF FIELD OF THE INVENTION

[0001] The present invention provides an antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s). The present invention also provides a process for preparing the antifoaming agent and compositions in coatings. The antifoaming agent of the present invention is a glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester. BACKGROUND OF THE INVENTION

[0002] A defoamer or an anti-foaming agent are commonly employed in coating formulations is a chemical additive that reduces and hinders the formation of foam in industrial process liquids. The terms anti-foam agent and defoamer are often used interchangeably. Defoamers eliminate existing foam and anti-foamers prevent the formation of further foam. Common antifoaming agents are insoluble oils, polydimethylsiloxanes, silicones, alcohols, stearates, and glycols.

[0003] CN Patent 102533034 B, 110183957 A, 102977258 A discloses a paint and its compositions having an emulsifier consisting of glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester and additives thereof.

[0004] US Patent 7893116 B2 describes a foam suppressant composition for water-dilutable paint, contains fatty acid mono-, di- and-or triglyceride, aliphatic hydrocarbon and ethoxylated and-or propoxylated fatty alcohol.

[0005] CN Patent 105400401 A discloses an environmentally friendly coating comprises rosin acid polyoxyethylene ester, castor oil epoxy ethane addition product and derivative, glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester, and thickening agent.

[0006] CN Patent 103602241 A discloses a high-viscosity water-proof paint contains hydroxypropyl methyl cellulose, potassium silicate, deionized water, styrene-acrylic emulsion, 2- ethylhexyl barium, glycerin polyoxyethylene ether fatty acid ester, and formaldehyde.

[0007] However, the prior art has not disclosed an antifoaming agent comprising polyoxyethylene ether polyoxypropylene ether fatty acid ester which can reduce and hinders the formation of foam,Docket No.: HER 12231PCT surface viscosity of film, enhance the velocity of drainage, and thus making the stability characteristic disappear.

[0008] The antifoaming agent of the present invention exhibits remarkably excellent defoaming properties (foam breaking, foam suppressing effect, defoaming sustainability) in coating applications, and the occurrence of repelling, cratering, etc. can be suppressed, and almost no defoaming deterioration is observed even after a long period of time has elapsed after adding to the target foaming liquid or a coating composition. SUMMARY OF THE INVENTION

[0009] The present invention provides an antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s). The present invention also provides a process for preparing the antifoaming agent and compositions in coatings.

[0010] In one aspect of the invention, the present application provides a method for producing the defoaming agent, wherein the method comprises the steps of: (a) reacting glycerol with ethylene oxide (EO) under catalyzed conditions, wherein the reaction proceeds to the degree of polymerization (8-10 EO) to form a glycerin polyoxyethylene ether; (b) reacting the resultant of step (a) with propylene oxide (PO) under catalyzed conditions using concentrated sulphuric acid at 90 to 100oC, wherein the reaction proceeds to the degree of polymerization (3-5 PO) to form a glycerin polyoxyethylene (EO) ether polyoxypropylene (PO) ether; and (c) reacting the resultant of step (b) with a fatty acid, wherein the reaction undergoes esterification to form a liquid glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester.

[0011] In another aspect of the invention, the present application provides an antifoaming composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% of a antioaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s); and (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive.

[0012] In another aspect of the invention, the present application provides a coating composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% of a antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s);Docket No.: HER 12231PCT and (c) at least one fatty acid(s); and (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive.

[0013] Yet another aspect of the invention, the present application provides an aqueous coating composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% antifoaming agent of glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester; (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive; and (C) water. BRIEF DESCRIPTION OF THE FIGURES

[0014] Further embodiments of the present application can be understood with the appended figures.

[0015] Figure 1 represents evaluation of bubble breaking time.Docket No.: HER 12231PCT DETAILED DESCRIPTION OF THE INVENTION

[0016] The disclosed and claimed inventive concept(s) is not limited in its application to the details of construction and the arrangement of the components and steps or methodologies set forth in the following description. The disclosed and claimed inventive concept(s) is capable of other aspects or of being practiced or carried out in various ways. The phraseology and terminology employed herein is for the purpose of description and should not be regarded as limiting.

[0017] Unless otherwise defined herein, technical terms used in connection with the disclosed and claimed inventive concept(s) shall have the meanings that are commonly understood by those of ordinary skill in the art. Unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular.

[0018] The singular forms "a," "an," and "the" include plural forms unless otherwise specified or clearly implied to the contrary by the context. The terms “comprising” and “comprised of” include the more restrictive meanings “consisting essentially of” and “consisting of.”

[0019] For purposes of the following detailed description, other than in any operating examples, or where otherwise indicated, numbers that express, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties to be obtained in carrying out the invention.

[0020] All percentages, parts, proportions, and ratios as used herein, are by weight of the total composition, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.

[0021] All publications, articles, papers, patents, patent publications, and other references cited herein are incorporated herein in their entirety for all purposes to the extent consistent with the disclosure herein.

[0022] As used herein, the following terms have the meanings set out below.

[0023] The term “at least one” means one as well as any quantity more than one, including but not limited to, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term “at least one” may extend up toDocket No.: HER 12231PCT 100 or 1000 or more depending on the term to which it is attached. In addition, the quantities of 100 / 1000 are not to be considered limiting as lower or higher limits.

[0024] The term “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”) or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.

[0025] The term “antifoaming agent” refers to an agent that prevents the foaming of the emulsion when applied to coatings. These antifoaming agents may be used as a single or as a composition.

[0026] The term “polymer” refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted or end capped. Non-limiting examples of polymers include copolymers, terpolymers, tetrapolymers, quaternary polymers, and homologues. The term “copolymer” refers to a polymer consisting essentially of two or more different types of monomers polymerized to obtain said copolymer.

[0027] The term “reaction product” refers to a substance produced from a chemical reaction of one or more reactant substances.

[0028] As used herein, the term "polyhydric alcohol" refers to an alcohol having at least 3 hydroxy groups.

[0029] As used herein, the term “polyhydric alcohols” or “polyols” refers to three or more hydroxyl groups include but are not limited to glycerol, trimethylolmethane, trimethylolethane, trimethylolpropane, benzenetriol, triethanolamine, threitol, erythritol, pentaerythritol, diglycerol, bis(trimethylolpropane), ribitol, xylitol, arabinitol, triglycerol, sorbitol, mannitol, dipentaerythritol, tetraglycerol, pentaglycerol and hexaglycerol.

[0030] As used herein the term "polyalkylene oxide" refers to a compound or group comprising repeating units derived from one or more alkylene oxides (e.g. ethylene oxide and / or propylene oxide). A polyalkylene oxide may comprise one repeating unit derived from one or more alkylene oxides or may comprise more than one different repeating unit, each of which may be derived fromDocket No.: HER 12231PCT one or more alkylene oxides. A polyalkylene oxide unit may comprise one or more polyalkylene oxide components, e.g. polyethylene oxide and / or polypropylene oxide components.

[0031] As used herein, the term “fatty acid” refers to a carboxylic acid (or organic acid), often with a long aliphatic tail, either saturated or unsaturated. Typically, fatty acids have a carbon- carbon bonded chain of at least 8 to 25 carbon atoms in length.

[0032] The term “alkyl” refers to a functionalized or unfunctionalized, monovalent, straight-chain, branched-chain, or cyclic C1-C60 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkyl is a C1-C45 hydrocarbyl group. In another non-limiting embodiment, an alkyl is a C1-C30 hydrocarbyl group. Non-limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n- heptyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n-dodecyl, tert-dodecyl, n-tetradecyl, n- hexadecyl, n-octadecyl, n-eicosyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The definition of “alkyl” also includes groups obtained by combinations of straight-chain, branched-chain and / or cyclic structures.

[0033] The term “aryl” refers to a functionalized or unfunctionalized, monovalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of aryl includes carbocyclic and heterocyclic aromatic groups. Non-limiting examples of aryl groups include phenyl, naphthyl, indenyl, indanyl, azulenyl, fluorenyl, anthracenyl, furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, 2,3-dihydrobenzofuranyl, benzo[b]thiophenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxyazinyl, pyrazolo[1,5-c]triazinyl, and the like.

[0034] The term “aralkyl” refers to an alkyl group comprising one or more aryl substituent(s) wherein "aryl" and "alkyl" are as defined above. Non-limiting examples of aralkyl groups include benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4- benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.Docket No.: HER 12231PCT

[0035] The term “alkylene” refers to a functionalized or unfunctionalized, divalent, straight-chain, branched-chain, or cyclic C1-C40 hydrocarbyl group optionally having one or more heteroatoms. In one non-limiting embodiment, an alkylene is a C1-C30 group. In another non-limiting embodiment, an alkylene is a C1-C20 group. Non-limiting examples of alkylene groups include: CH CH CH C 32 , 2 H2 , CH CH2, CH CH3CH33C CH2CH2C CH2CH ,CH3,CH3,CH CH3CH33CH3 C CCH2CH2CH2 ,CH CH2 CH2 , CH2 CH CH2 ,CH2CH2CH, CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2, , ,

[0036] The term “arylene” refers to a functionalized or unfunctionalized, divalent, aromatic hydrocarbyl group optionally having one or more heteroatoms. The definition of arylene includes carbocyclic and heterocyclic groups. Non-limiting examples of arylene groups include phenylene, naphthylene, pyridinylene, and the like.Docket No.: HER 12231PCT

[0037] The term “heteroatom” refers to oxygen, nitrogen, sulfur, silicon, phosphorous, or halogen. The heteroatom(s) may be present as a part of one or more heteroatom-containing functional groups. Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups. The heteroatom(s) may also be present as a part of a ring such as in heteroaryl and heteroarylene groups.

[0038] In one non-limiting embodiment, the polyhydric alcohol(s) consisting of at least three hydroxyl groups selected from trimethylolmethane, trimethylolethane, trimethylolpropane, benzenetriol, triethanolamine, threitol, erythritol, pentaerythritol, diglycerol, bis(trimethylolpropane), ribitol, xylitol, arabinitol, triglycerol, sorbitol, mannitol, dipentaerythritol, tetraglycerol, pentaglycerol and hexaglycerol and glycerol.

[0039] In one non-limiting embodiment, the polyalkylene oxide(s) is selected from the group consisting of polymer of ethylene oxide (EO), polymer of propylene oxide (PO), and polymer of ethylene oxide(EO) / propylene oxide(PO).

[0040] In one non-limiting embodiment, the fatty acid is selected from the group consisting of C8- C24fatty acids comprising a saturated fatty acid selected from the group consisting of caprylic acid, perargonic acid, caproic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, linoleic acid, or linolenic acid; and an unsaturated fatty acid selected from the group consisting of 2-ethylhexanoic acid, isopalmitic acid, and iso-stearic acid.

[0041] In one non-limiting embodiment, the present application provides an antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s). The present invention also provides a process for preparing the antifoaming agent and its compositions in coatings.

[0042] In another non-limiting embodiment, the present application provides a method for producing the defoaming agent , wherein the method comprises the steps of: (a) reacting glycerol with ethylene oxide (EO) under catalyzed conditions, wherein the reaction proceeds to the degree of polymerization (8-10 EO) to form a glycerin polyoxyethylene ether; (b) reacting the resultant of step (a) with propylene oxide (PO) under catalyzed conditions using concentrated sulphuric acid at 90 to 100oC, wherein the reaction proceeds to the degree of polymerization (3-5 PO) to form aDocket No.: HER 12231PCT glycerin polyoxyethylene (EO) ether polyoxypropylene (PO) ether; and (c) reacting the resultant of step (b) with a fatty acid, wherein the reaction undergoes esterification to form a liquid glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester.

[0043] In another non-limiting embodiment, the present application provides a coating composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% of a antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s); and (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive.

[0044] In another non-limiting embodiment, the present application provides an aqueous coating composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% antifoaming agent of glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester; (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive; and (C) water.

[0045] According to another embodiment of the present application, it is contemplated to employ at least one additive selected from the group consisting of coalescent agents, film-forming agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents; UV absorbers, pigments, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants and plasticizers. Preferably, the composition is used in paper products, metal coatings, architectural coatings, graphic arts, fibrous materials, films, sheets, composites, printing inks, inkjet printing, flock and other adhesives, hair care products, skin care products, nail care products, house-hold products, livestock / agriculture, wood coatings, textile products, nonwoven coatings, and seed applications.

[0046] According to another embodiment of the present application, the coating composition of the present application is used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.

[0047] According to another embodiment of the present application, the coating composition of the present application is is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks,Docket No.: HER 12231PCT medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and blends, woven, knitted, natural, synthetic, and regenerated substrates.

[0048] According to another embodiment of the present application, the coating composition of the present application is in the form of an aqueous or a non-aqueous anti-foaming composition.

[0049] In another embodiment, the present application discloses that the coating composition comprises the antifoaming agent in an amount of from about 0.1 wt.% to about 0.2 wt.%; or from about 0.2 wt.% to about 0.3 wt.%; or from about 0.3 wt.% to about 0.4 wt.%; or from about 0.4 wt.% to about 0.5 wt.%; from about 0.5 wt.% to about 0.6 wt.%; from about 0.6 wt.% to about 0.7 wt.%; from about 0.7 wt.% to about 0.8 wt.%; from about 0.8 wt.% to about 0.9 wt.%; from about 0.9 wt.% to about 1.0 wt.%; about 1.0 wt.% to about 2 wt.%; or from about 2.0 wt.% to about 3.0 wt.%; about 3.0 wt.% to about 4.0 wt.%; or from about 4.0 wt.% to about 5.0 wt.%; based on the total weight of the composition.

[0050] In another embodiment, the present application discloses that, in the composition comprising one or more additive, the additive is present in an amount of from about 0.5 wt.% to about 1 wt.%; or from about 1 wt.% to about 2.5 wt.%; or from about 2.5 wt.% to about 5 wt.%; or from about 5 wt.% to about 10 wt.%; or from about 10 wt.% to about 15 wt.%; or from about 15 wt.% to about 20 wt.%; or from about 20 wt.% to about 25 wt.%; or from about 25 wt.% to about 30 wt.%; or from about 30 wt.% to about 35 wt.%; or from about 35 wt.% to about 40 wt.%; or from about 40 wt.% to about 45 wt.%; or from about 45 wt.% to about 50 wt.%; or from about 50 wt.% to about 55 wt.%; or from about 55 wt.% to about 60 wt.%; or from about 60 wt.% to about 65 wt.%; or from about 65 wt.% to about 70 wt.%; or from about 70 wt.% to about 75 wt.%; or from about 75 wt.% to about 80 wt.%; or from about 80 wt.% to about 85 wt.%; or from about 85 wt.% to about 90 wt.%; or from about 90 wt.% to about 94.9 wt.%; based on the total weight of the composition.

[0051] In another embodiment of the present application, the coating composition comprising coalescent agents can include, but are not limited to ester alcohols, benzoate ethers, glycol ethers, glycol ether esters and N-methyl-2-pyrrolidone.

[0052] In another embodiment of the present application, in the composition comprising emulsifiers, the emulsifiers are selected from anionic emulsifiers, such as mono-, di- or triethanolamine oleate, mono-, di- or triethanolamine stearate, 2-amino-2-methylpropan-1-olDocket No.: HER 12231PCT stearate, sulfonated compounds (for example, sodium dodecylsulfate, turkey red oil, etc.) and sulfonated compounds (e.g., sodium cetylsulfonate), cationic emulsifiers such as quaternary ammonium compounds (for example, cetyltrimethylammonium bromide, benzyllauryldimethylammonium chloride, etc.), amphoteric emulsifiers (e.g., lecithins) and nonionic emulsifiers, such as fatty alcohols (lauryl, cetyl, or stearyl alcohol), partial fatty acid esters of polyhydric alcohols with saturated fatty acids (glycerol monostearate, pentaerythritol monostearate, ethylene glycol monostearate, propylene glycol monostearate), partial fatty acid esters of polyhydric alcohols with unsaturated fatty acids (for example glycerol monooleate, pentaerythritol monooleate), polyoxyethylene esters of fatty acids (e.g., polyoxyethylene stearate), polymerization products of ethylene oxide and propylene oxide with fatty alcohols (fatty alcohol polyglycol ethers) or fatty acids (fatty acid ethoxylates),

[0053] In one embodiment, the present application discloses a composition comprising suitable rheology modifiers to control viscosity over a wide shear rate range. Moreover, the coating compositions contain rheology modifiers such as fine-particle silica, layered silicates, polymeric cellulosics, or nonionic synthetic associative thickeners (NSAT’s).

[0054] Suitable dispersing agents employed in the composition include but are not limited to non- ionic, anionic and cationic dispersants such as 2-amino-2-methyl-1 -propanol (AMP), dimethyl amino ethanol (DMAE), potassium tripolyphosphate (KTPP), trisodium polyphosphate (TSPP), citric acid and other carboxylic acids, and the like. Also, suitable dispersants for the present composition are anionic polymers, such as homopolymers of carboxylic acids such as acrylic, methacrylic or maleic acid, and more hydrophobic copolymers of acrylic, methacrylic or maleic acid that include monomers such as styrene, acrylate or methacrylate esters, isobutylene, and other hydrophilic or hydrophobic comonomers as well as the salts of the aforementioned dispersants, and mixtures thereof.

[0055] To prevent evaporation of water from the composition before the coating has fully dried, suitable humectants can be added. Examples of such humectants are ethylene glycol, glymes, polyethylene glycol, and methoxy polyethylene glycols.

[0056] In another embodiment of the present application, thickeners are added to compositions to achieve the desired viscosity and flow properties. Thickeners can include but are not limited to cellulose derivatives, such as hydroxyethyl cellulose, methyl cellulose or carboxymethyl cellulose.Docket No.: HER 12231PCT Other thickeners include but are not limited to polyvinyl alcohol (PVA), hydrophobically- modified, alkali-soluble emulsions known in the art as HASE emulsions, alkali-soluble or alkali- swellable emulsions known in the art as ASE emulsion, hydrophobically-modified ethylene oxide- urethane polymers known in the art as HEUR thickeners; and cellulosic thickeners such as hydroxymethyl cellulose (HMC), hydroxyethyl cellulose (HEC), hydrophobically-modified hydroxy ethyl cellulose (HMHEC), sodium carboxymethyl cellulose (SCMC), sodium carboxymethyl 2-hydroxyethyl cellulose, 2- hydroxypropyl methyl cellulose, 2-hydroxyethyl methyl cellulose, 2-hydroxybutyl methyl cellulose, 2-hydroxyethyl ethyl cellulose, 2- hydoxypropyl cellulose, and the like. Also useful as thickeners are fumed silica, attapulgite clay and other types of clay, titanate chelating agents, and the like.

[0057] “Antifreeze agent” refers to additives which prevent freezing. Suitable antifreeze agents can include but are not limited to alcohols, polyols such as glycerol, glycols such as propylene glycol and polyol fatty acid esters, or their derivatives.

[0058] One or more preservative may be added in the compositions in low doses to protect against the growth of micro-organisms. Preservatives can include but are not limited to 2-meth-4- isothiazolin-3-one (MIT), 1,2-Benzisothiazolin-3-one (BIT), 5-Chloro-2-methyl-4-isothiazolin-3- one (CMIT), 2-Octyl-4-isothiazolin-3-one (Off) 3-Iodo-2-propynylbutyl carbamate (IPBC), oxyfluorfen, thiabendazole, terbutryn, zinc pyrithione (ZnPy) and suitable mildewcides and biocides in the composition include zinc oxide, isothiazolones, triazoles.

[0059] In another embodiment of the present application, suitable latex adhesion promoters in the composition include, but are not limited to, homopolymers, copolymers or terpolymers such as, for example, polymers or copolymers of acrylic or methacrylic acid, polyvinyl acetate, styrene- acrylic copolymers, styrene-butadiene copolymers, vinyl acetate-acrylic copolymers, ethylene- vinyl acetate copolymers, vinyl acetate-vinyl versatate copolymers, vinyl acetate-vinyl maleate copolymers, vinyl acetate-vinyl chloride-acrylic terpolymers, ethylene-vinyl acetate-acrylic terpolymer, and urethane polymers. The polymers may contain up to about 10% by weight of monomers containing functional groups, for example, but not limited to, carboxylic acid, phosphate, sulfate, sulfonate and amide groups, other monomers, and mixtures thereof.

[0060] The composition of the present disclosure can further include at least one pigment. The pigment can be selected from the group consisting of phthalocyanines, iron oxides, titaniumDocket No.: HER 12231PCT dioxides, zinc oxide, indigo, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silica, talc, calcium carbonate, and mixtures thereof. Titanium dioxide grades used in the composition are surface modified with various inorganic oxides, such as silicates, aluminates, and zirconates. Aluminum silicate, nepeline syenite, mica, calcium carbonate, and / or diatomaceous earth can also be employed.

[0061] The coating composition of the present disclosure comprises at least one film forming polymer. The film forming polymer of the present disclosure can be selected from a wide variety of polymers known in the related art. For instance, these film forming polymers can be derived from various ethylenically unsaturated monomers such as ethylene, vinyl and acrylic monomers. Examples of such monomers can include, but are not limited to, acrylic acid, methacrylic acid, methacrylic acid esters, styrene, α-methyl styrene, vinyl chloride, acrylonitrile, methacrylonitrile, ureido methacrylate, vinyl acetate, vinyl esters of branched tertiary monocarboxylic acids, itaconic acid, crotonic acid, maleic acid, fumaric acid, and ethylene. It is also possible to include C4-C8 conjugated dienes such as 1,3-butadiene, isoprene and chloroprene. The film forming polymers can also be copolymerized products of more than one monomer to achieve several desired properties, particularly for applications in latex paints with very little or no volatile organic compounds (VOCs). Examples of suitable film forming polymers can include, but are not limited to, homo- or co-polymers of vinyl acetate, methacrylic acid, methylacrylate, methylmethacrylate, ethylacrylate, butyl acrylate, styrene, ethylene, vinyl chloride, vinyl ester of neodecanoic acid, vinyl propionate, butadiene, acrylonitrile, maleates, and fumarates. In one non-limiting embodiment of the present disclosure, the film forming polymer is selected from the group consisting of acrylics, vinyl-acrylics and styrene-acrylics, styrene-butadiene copolymers, vinyl acetate ethylenes, butadiene-acrylonitrile copolymers, polyepoxides, polyurethanes, polyamides, vinyl esters of neodecanoic acid and polyesters.

[0062] Examples of other suitable film forming polymers can include, but are not limited to, alkyds, cellulosics (cellulose nitrate and cellulose esters), coumarone-indenes, epoxies, esters, hydrocarbons, melamines, natural resins, oleo resins, phenolics, polyamides, polyesters, rosins, silicones, terpenes, urea, and urethanes.

[0063] Examples of the modified silicone additives used herein include amino-modified silicone agents, carbinol-modified silicone agents, methacrylic-modified silicone agents, polyether-Docket No.: HER 12231PCT modified silicone agents, alkyl-modified silicone agents, ester-modified silicone agents and an alkylene oxide-modified silicone agents.

[0064] Additives in minor amounts, i.e., less than about 10% by weight, based on the total weight of the composition, can be included. Such additives include cosolvents, wet-edge additives, wetting agents, wax, colorants, anticaking agents, UV absorbers, gel inhibitors, hydrophobic agents, and antioxidants.

[0065] The coating composition in the form of a paint can include enamels, lacquers, varnishes, undercoats, primers, seals, fillers, stoppers, and the like.

[0066] Further, certain aspects of the present application are illustrated in detail by way of the following examples. The examples are given herein for illustration of the application and are not intended to be limiting thereof.Docket No.: HER 12231PCT EXAMPLES

[0067] Defoaming test:

[0068] Test in 70%PVC Latex paint comprises the addition of 0.4% wt. foam control agent (polymer contained) and was diluted the paint to 70KU and roll it on putty board and evaluate the bubble breaking time (Table 1; Table 2 and Figure 1).

[0069] As shown in Table 2 and Figure 1, silicone polyether and polymer are used as the active ingredients of the defoamer. The dosage of silicone polyether in the defoamer is fixed at 8%, and as the dosage of polymer changes from 0% to 25%, according to the formula defoaming performance test method which described in

[0067] , the defoaming speed has been significantly improved (from 62s to 19s). Table 1: 70% PVC Latex paint formulation Stage Raw materialDosage(wt.%)Water 25.0 HEC 0.22 HMHEC 0.27 2-amino-2-methyl-1-propanol 0.15 Grinding stage Polycarboxylate sodium 0.45 Mineral oil 0.1 Titanium dioxide 17 Kaolin 7.0 Calcium carbonate 4.0 Talc 18.5 Water 4.0 Styrene acrylic emulsion 16.0 Kathon 0.4 Let down stage nonionic emulsifier 0.2 Texanol 1.4 phosphate ester surfactant 0.2 Water 4.71 Foam control agent 0.4 Table 2: Dosage (wt.%) Silicon polyether 8 8 8 8 8 8 in FCA Polymer 0 5 10 15 20 25 Bubble breaking time (seconds) 62 37 30 23 19 19

Claims

Docket No.: HER 12231PCT We claim:

1. An antifoaming agent comprising a reaction product of (a) one or more polyhydric alcohol(s); (b) one or more polyalkylene oxide(s); and (c) at least one fatty acid(s).

2. The antifoaming agent according to claim 1, wherein the polyhydric alcohol(s) consisting of at least three hydroxyl groups selected from trimethylolmethane, trimethylolethane, trimethylolpropane, benzenetriol, triethanolamine, threitol, erythritol, pentaerythritol, diglycerol, bis(trimethylolpropane), ribitol, xylitol, arabinitol, triglycerol, sorbitol, mannitol, dipentaerythritol, tetraglycerol, pentaglycerol and hexaglycerol and glycerol.

3. The antifoaming agent according to claim 1, wherein the polyhydric alcohol is a glycerol.

4. The antifoaming agent according to claim 1, wherein the polyalkylene oxide(s) is selected from the group consisting of polymer of ethylene oxide (EO), polymer of propylene oxide (PO), and polymer of ethylene oxide(EO) / propylene oxide(PO).

5. The antifoaming agent according to claim 1, wherein the polyalkylene oxide is a polymer of EO / PO, wherein the EO polymer chain length is from about 8 to about 10 carbon atoms and the PO polymer chain length is from about 3 to about 5 carbon atoms.

6. The antifoaming agent according to claim 1, wherein the fatty acid is a saturated or unsaturated fatty acid.

7. The antifoaming agent according to claim 1, wherein the fatty acid is selected from the group consisting of C8-C24fatty acids.

8. The antifoaming agent according to claim 6, wherein the saturated fatty acid is selected from the group consisting of caprylic acid, perargonic acid, caproic acid, lauric acid,Docket No.: HER 12231PCT myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, linoleic acid, or linolenic acid; and unsaturated fatty acid is selected from the group consisting of 2- ethylhexanoic acid, isopalmitic acid, and iso-stearic acid.

9. The antifoaming agent according to claim 1, wherein the reaction product is a glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester.

10. The antifoaming agent according to claim 1, wherein the reaction product is a glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester.

11. A process for preparing defoaming agent of claim 1, wherein the process comprises the steps of: (a) reacting glycerol with ethylene oxide (EO) under catalyzed conditions using sulphuric acid in a molar ratio of 1:2 to 1:3, wherein the reaction provides 8-10 EO degree of polymerization to form a glycerin polyoxyethylene ether; (b) reacting the resultant of step (a) with propylene oxide (PO) under catalyzed conditions using concentrated sulphuric acid in a molar ratio of 1:2.5 to 1:3 at 90 to 100oC, wherein the reaction provides 3-5 PO degree of polymerization to form a glycerin polyoxyethylene (EO) ether polyoxypropylene (PO) ether; and (c) reacting the resultant of step (b) with a fatty acid, wherein the reaction undergoes esterification in a molar ratio of 1:0.8 to 1:2 to form a liquid glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester.

12. The method for producing the defoaming agent according to claim 11, wherein glycerin polyoxyethylene ether polyoxypropylene ether fatty acid ester is a glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester.

13. An antifoaming composition comprising: (A) from about 0.1 wt.% to about 5.0 wt.% antifoaming agent of Claim 1; and (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive 14. A coating composition comprising:Docket No.: HER 12231PCT (A) from about 0.1 wt.% to about 5.0 wt.% antifoaming agent of Claim 1; and (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive.

15. The coating composition according to claim 13 , wherein the additive (B) is selected from the group consisting of silicon agents, coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers.

16. The coating composition according to claim 14 , wherein the additive (B) is selected from the group consisting of coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizers.

17. The coating composition according to claim 14, wherein the coating composition is used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.

18. The coating composition according to claim 14, wherein the composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non- woven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and blends, woven, knitted, natural, synthetic, and regenerated substrates.

19. The coating composition according to claim 14, wherein the composition is in the form of an aqueous or a non-aqueous anti-foaming composition.

20. An aqueous coating composition comprising:Docket No.: HER 12231PCT (A) from about 0.1 wt.% to about 5.0 wt.% antifoaming agent of glycerin polyoxyethylene ether polyoxypropylene ether stearic acid ester; (B) from about 10.0 wt.% to about 94.9 wt.% at least one additive; and (C) water.

21. The coating composition according to claim 20 , wherein the additive (B) is selected from the group consisting of coalescent agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersing agents, defoamers, wet-edge additives, wetting agents, humectants, wax, colorants, thickeners, anticaking agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, anti-oxidants, pigment, and plasticizer.

22. The coating composition according to claim 20, wherein the aqueous coating composition is used for lacquer coating, primer coating, ink jet printing, top coating, varnish coating, architectural coating, wood coating, printing inks, or metallic or non-metallic coatings.

23. The coating composition according to claim 20, wherein the aqueous coating composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, papers, non-woven materials, textiles, leather, wood, concrete, masonry, metals, non- metals, house wrap, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and blends, woven, knitted, natural, synthetic, and regenerated substrates.

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