WO2021143999A1

WO2021143999A1 - New coalescing agent for coating compositions and coating compositions comprising the same

Info

Publication number: WO2021143999A1
Application number: PCT/EP2020/050716
Authority: WO
Inventors: Sergio Martins; Olivier BACK; Antony Felipe BARRETO BARBOSA
Original assignee: Rhodia Operations
Priority date: 2020-01-13
Filing date: 2020-01-13
Publication date: 2021-07-22

Abstract

The invention relates to the use of a compound as coalescing agent for coating compositions such as paints, in particular waterborne paints, wherein said compound is an ester, notably 1-phenyldodecyl acetate that comes at least partially from renewable source.

Description

NEW COALESCING AGENT FOR COATING COMPOSITIONS AND COATING COMPOSITIONS COMPRISING THE SAME

FIELD OF THE INVENTION

[001 ] This invention relates to the use of a compound as coalescing agent for coating compositions such as paints, in particular waterborne paints, wherein said compound is an ester, notably 1-phenyldodecyl acetate that comes at least partially from renewable source.

BACKGROUND OF THE INVENTION

[002] Coalescing agents are compounds that can be used to temporarily soften the polymeric particles of the coating compositions, which allow said polymeric particles to coalesce together when the coating composition dries. Coalescing agents help achieving optimal film formation. Said agents aid in avoiding cracks or issues with adherence to substrate surfaces when the coating composition dries at room temperature, for example.

[003] One of the biggest concerns nowadays regarding said agents is related to the environmental footprint thereof. Said environmental footprint is intrinsically related to the volatile organic compounds (VOC) emissions. Traditionally, coalescing agents were high-VOC with low biodegradability. With tightening environmental legislation, there is a requirement for high boiling point, biodegradable coalescing agents, having less impact on environment.

[004] In this perspective of providing low VOC solutions, W02009/097142 describes coalescent compositions for coating compositions such as paints, adhesives, and coatings comprising a blend of dibasic esters, specifically (i) esters of adipic, glutaric, and/or succinic acids and/or (ii) esters of isomers of adipic acid.

[005] Also, WO2016/107744 describes aqueous dispersions that can comprise a first copolymer derived from one or more ethylenically unsaturated monomers, and a second carboxy-functional copolymer derived from one or more carboxylic acid-containing monomers. The aqueous dispersions can be used to prepare low-VOC aqueous coating compositions.

[006] Currently commercially available coalescing agents are ester- based compounds like bis(2-methylpropyl) ester of hexanedioic acid (diisobutyl adipate or DIPA, commercially available under the name Dhaytan AD204 by Solvay), or 2-ethylhexyl benzoate (commercially available from Velsicol Corporation under the trade name VELATE 378) or ester alcohols like 2,2,4- trimethyl-1 ,3-pentanediol monoisobutyrate (also sold as Texanol® by Eastman). Those existing coalescing agents are not biosourced. In addition, DIPA and Texanol® have a boiling point that is respectively 305°C (DIPA) and 254°C (Texanol®) which could be considered to be above the limit in future regulations on VOC emissions.

[007] Indeed, the emission of volatile organic compounds ("VOC") during the curing of paint has adverse environmental and health consequences.

[008] Therefore, the present invention aims to identify and provide high performance new coalescing agents for coating compositions which are at least partially derived from renewable source materials, have lower VOC emissions, are at least partially biodegradable thus have improved environmental footprint compared to existing solutions.

[009] The material of the present invention has good coalescence properties, notably in latex based coating compositions compared to currently available coalescent agents, such as diisobutyl adipate and 2, 2, 4-trimethyl-1 ,3- pentanediol monoisobutyrate, a higher boiling point (higher than 250°C) which results in a non-VOC emission and can be originated from renewable resources like coconut fatty acid.

SUMMARY OF THE INVENTION

[0010] The present invention thus propose the use of a compound having the general Formula 1 , Formula 1 as coalescing agent for coating compositions wherein Ar is an aryl group which optionally has one or more H atom(s) substituted by functional group(s) and/or by linear or branched alkyl groups,

R is a linear or branched C7-C19 alkyl group or C7-C19 alkenyl group, and

R’ is H or a C1-C4 alkyl group.

[0011] The present invention also provides a coating composition comprising:

• a liquid carrier,

• a polymer, and

• a compound of Formula 1

Formula 1 wherein

Ar is an aryl group which optionally has one or more FI atom(s) substituted by functional group(s) and/or by linear or branched alkyl groups, R is a linear or branched C7-C19 alkyl group or C7-C19 alkenyl group, and

R’ is H or a C1-C4 alkyl group.

DEFINITIONS

[0012] By “coalescing agent” or “coalescing aid” it is understood to mean that the compound of Formula 1 makes the polymer particles of the coating composition soft enough at the point of coalescence to form a continuous film. A coalescing aid is often referred to as a temporary plasticizer for a film-forming polymer. The function of the coalescent is to soften the polymer during the crucial period of fusion so that the individual particles will combine to form a continuous film. The coalescing aid must then slowly evaporate, thereby allowing the paint film to develop its maximum durability and appearance properties. Equivalents of “coalescing agent” wording are “film forming agent” or “drying retardant”.

[0013] The term “coating compositions” is covering paints, varnishes, lacquers, adhesives and inks. It is preferably referring to paints, and in particular waterborne paints.

[0014] "Low VOC" refers to a coating composition that contains less than about 50 grams/liter volatile organic compounds, more preferably less than about 25 grams/liter volatile organic compounds, and most preferably less than about 5 grams/liter volatile organic compounds based upon the total liquid coating composition. In some embodiments, the coating composition is substantially free of VOCs. When used with respect to a component which may be found in paint composition, the term "substantially free of means containing less than about 1 wt% of the component based on the composition weight.

[0015] The term “latex” is not referring to the use of a rubber at all but to resins made of acrylic or vinyl repeat units.

[0016] In this application the term "waterborne" means that the major liquid vehicle or carrier for coating composition is water. [0017] In this application the terms "polymer" and "polymeric" include polymers as well as copolymers of two or more monomers.

[0018] In Formula 1 “aryl group” is an aromatic radical (aromatic ring wherein a H is removed to be able to bound in Formula 1 ) which can be optionally substituted by one or more functional group(s) and/or by linear or branched C1- C12 alkyl groups.

[0019] The term aromatic ring can designate a cyclic conjugated unsaturated hydrocarbon ring having a number of delocalized p electrons following the Fluckel rule.

[0020] The term aromatic ring encompasses also heteroaromatic ring that is to say cyclic conjugated unsaturated ring containing one or more heteroatoms and having a number of delocalized p electrons following the Fluckel rule.

[0021] The term aromatic ring encompasses also polycyclic aromatic compounds. In the polycyclic aromatic compounds, the rings can be fused or they can be linked by C-C linkage or by a spiro linkage.

[0022] Ar may represent an optionally substituted phenyl group of formula

[0023] wherein Xi_, X2, X3, X4 and X5 which can be the same or different represent

[0024] - hydrogen or a C1-C24 linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0025] - halogen,

[0026] - hydroxy (-OH) or alkoxy group (-OR1 ) wherein R1 is a linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0027] - amino group (-NRR¹) wherein R1 and R2 independently represent a linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0028] - acyl group (-(C=0)-R1) wherein R1 represent hydrogen or a C1-C24 linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0029] - carboxyl (-COOH) or alkoxycarbonyl group (-(C=0)-OR1) wherein R1 represents a C1-C24 linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0030] - carbamoyl group (-(C=0)-NR1 R2) wherein R1 and R2 independently represent a linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups,

[0031] - alkylsulfonyl group (-S02-R1) or alkylsulfmyl group (-SO-

R1) or

[0032] alkylthio (-S-R1) wherein R1 represent a C1-C24 linear or branched hydrocarbon radical having 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups.

[0033] Ar may also represent an optionally substituted 2-pyridyl, 3- pyridyl or 4-pyridyl group of formula

[0034]

[0035] wherein Xi_, X2, X3 and X4 which can be the same or different have the same meaning as above described.

[0036] Ar may also represent an optionally substituted furan-2-yl or furan-3-yl group of formula

[0038] wherein Xi_, X2 and X3 which can be the same or different have the same meaning as above described.

[0039] Ar may also represent an optionally substituted 1 -FI-pyrol-2- yl or 1 -H-pyrol-3-yl group of formula :

[0041 ] wherein Xi X2, X3 and X4 which can be the same or different have the same meaning as above described.

[0042] Ar may also represent an optionally substituted thiophen-2- yl or thiophen-3-yl group of formula :

[0044] In some embodiments, substituents X; and X1 +1 borne by 2 adjacent carbons of the phenyl, the pyridyl, the furanyl, the pyrolyl or the thiophenyl, form together an optionally substituted cyclic moiety said cyclic moiety being an aromatic, hetero aromatic or non-aromatic group.

[0045] COMPOUNDS OF FORMULA 1

[0046] In a first preferred embodiment, in the compound of Formula 1 , Ar is a phenyl group. The formula 1 is thus Formula 1.1 below: Formula 1.1 wherein R and R’ are as defined above.

[0047] In another preferred embodiment, in the compound of Formula 1, Ar is phenyl, R’ is a methyl group and R is a C10-C12 linear or branched alkyl group.

[0048] Even more preferably, in the compound of Formula 1 of the invention, Ar is phenyl, R’ is a methyl group and R is a C11 linear alkyl group, resulting in a compound having the following Formula 1.2:

Formula 1.2

[0049] The compounds of Formula 1, 1.1 and 1.2 are advantageously in the form of a racemic mixture.

[0050] This compound of Formula 1.2 has a boiling point above 250°C, notably predicted at 357°C, which is superior to the boiling point of the two existing coalescing agents: diisobutyl acetate BP 305°C and Texanol® BP 254°C. This results in an even lower VOC emission.

[0051] Compounds of Formula 1 can be produced according to the following reaction scheme, under suitable esterification conditions that are well known by a person skilled in the art so that no further detail needs to be given here. Wherein X can be -OH or -0-C(=0-)-R’, and Ar, R and R’ are as defined in the above description. [

[0052] A similar synthesis is generically described on p. 56 of WO201 8/229285.

[0053] In general, the carbinol (I) can be prepared according to section 7.4., p. 50 of WO2018/229285 or as described from p. 16, I. 35 to p. 17, I. 25 of W02019/106196A, that are both incorporated by reference in this application. The internal ketone from which the carbinol (I) is obtained can be prepared as described from p. 4 to p. 13, I. 34 of WO2018/229285.

[0054] This internal ketone is prepared by cross-ketonization between a carboxylic acid of formula Ar-COOH (III) and R-COOH (IV), typically between benzoic acid and a fatty acid like lauric acid which can be biosourced e.g. from coconut fatty acids.

[0055] Compound (II) can be e.g. acetic acid (R’=-CH3, X=-OH) or acetic anhydride (R’=-CH3, X = -0-C(=0-)-CH3). Acetic anhydride can also be biosourced.

[0056] Starting from the afore-mentioned compounds, coating compositions, including waterborne paint compositions have been developed. COATING COMPOSITIONS

[0057] The coating composition according to the invention comprises a liquid carrier, a polymer and the compound of Formula 1. [0058] The compound of Formula 1 is advantageously a compound of Formula 1.1 and more preferably a compound of Formula 1 .2 as described in all the above mentioned embodiments.

[0059] The liquid carrier used in the preparation of said compositions is preferably water.

[0060] Suitable polymers for the coating composition include acrylics, (meth)acrylics, vinyls, polyesters, polyurethanes, vinyl acetate ethylene, polybutadiene, polyvinylidene, styrene acrylics, vinyl acrylics, vinyl versatic acid esters, styrene/butadiene, epoxy esters, polysiloxanes, silicones, fluorinated copolymers, and mixtures or copolymers thereof. Acrylics, vinyls, vinyl acrylics and mixtures or copolymers thereof are preferred.

[0061 ] The coating compositions may further comprise one or more additives selected from the group consisting of alkalizer agent(s), mineral filler(s), pigment(s) and other additive(s).

[0062] Alkalizer agents are selected from the group consisting of ammonium hydroxide, aqueous solutions of decahydrated borax and sodium hydroxide, and metal complexes of alkaline salts, preferably wherein said metal complexes are commercially available under the trade name SYCO 095. Mixtures of more than one alkalizer are possible.

[0063] The mineral filler is advantageously selected from the group consisting of silicates, carbonates, oxides, sulfates and mixtures thereof.

[0064] Among the preferred silicates, we can cite clays, aluminum silicate, hydrated aluminum silicate, magnesium silicate, hydrated magnesium silicate, sodium-potassium aluminum silicates, microcrystalline silica, attapulgite, pagodite, mica and kaolin. Clays can be hydrous and delaminated clays or calcined and structured clays.

[0065] Among the preferred carbonates, calcium carbonate is preferred. [0066] Regarding the oxides, titanium dioxide is preferred. This component also plays the role of pigment in the coating composition.

[0067] Calcium sulfate is the preferred sulfate.

[0068] One preferred embodiment is using kaolin as mineral filler.

[0069] When other additive are used, they are preferably selected from the group consisting of defoamers, biocides, plasticizers, corrosion inhibitors, dispersants, humectants, surfactants, organic solvents, co-coalescent, rheology modifiers, UV absorbers, colorants and thickeners.

[0070] The defoamers can be selected from the group consisting of oil based defoamers, silicone polymer based defoamers, white mineral oil based defoamers and mixtures thereof.

[0071] The biocides include fungicides, bactericides, antimicrobial and algaecides. They may be selected from the group consisting of isothiazolinones and derivatives thereof (1 ,2-benzisothiazolin-3-one (BIT), 5- chloro-2-methyl-4-isothiazolin-3-one / 2-methyl-4-isothiazolin-3-one (CMIT/MIT), 2-methyl-4-isothiazolin-3-one (MIT),) derivatives of isothiazolinones and semi acetals, carbamates like iodopropynylbutylcarbamate (IPBC), diiodomethyl- ptolylsulfone, 2,2-dibromo-3-nitrilopropionamide (DBNPA), 1-(3-chloroallyl)- 3,5,7-triaza-1-azoniaadamantane chloride (CTAC), Dimethylol-dimethyl- hydantoin (DMDMH), 1 ,2-dibromo-2,4-dicyano-butane (DBDCB), Zinc pyrithione (ZPT), and N-methyl-1 ,2-benzisothiazol-3(2H)-one (MBIT). Biocides may also act as preservatives. Typical fungicides used in the paint industry for dry film preservation include: carbendazim (BCM), chlorothalonil (CTL), octylisothiazolinone (OIT), dichlorooctylisothiazolinone (DCOIT), n-butyl- benzisothiazolinone (BBIT), and zinc pyrithione (ZnPT).

[0072] The corrosion inhibitors may be selected from the group consisting of inorganic compounds such as oxides, nitrites and chromates, preferably being sodium nitrite. [0073] The dispersants may be selected from the group consisting of acrylic polymer dispersion, such as sodium acrylate dispersion

[0074] Salt of a polycarboxylic acid, such as disodium maleate, preferably in the form of aqueous solutions, and modified fatty acids solutions act as dispersants and humectants.

[0075] Other humectants may be selected from the group consisting of non-ionic surfactants blends, such as ethoxylated C9-C11 alcohols and Nopol ethoxylated propoxylated.

[0076] UV absorber are such as for example, encapsulated hydroxyphenyl-triazine compositions and other compounds known to those of ordinary skill in the art.

[0077] In some embodiments, the coating composition includes a colorant, which in this application means a composition that may be added to alter the hue or lightness of the composition, and which contains pigment or dye and an optional vehicle but is substantially free of film forming polymeric components.

[0078] In some embodiments, the coating composition includes a pigment, which in this application refers not only to particulate pigments that function by reflecting light but also soluble or dispersible dyes that function by absorbing light. Suitable examples of pigments include, without limitation, titanium dioxide white, carbon black, lamp black, black iron oxide, red iron oxide, yellow iron oxide, brown iron oxide (a blend of yellow and red oxide with black oxide), phthalocyanine green, phthalocyanine blue, organic reds (such as naphthol red, quinacridone red and toluidine red), quinacridone magenta, quinacridone violent, DNA orange, and/or organic yellows (such as Hansa yellow), for example.

[0079] The rheology modifiers, viscosity modifiers and/or thickeners may be selected from the group consisting of alkali-swellable (or soluble) emulsions (ASEs), nonionic hydrophobically modified ethylene oxide urethane block copolymers (also referred to herein as HEUR thickeners), nonionic hydrophobic ethoxylated aminoplast polymers (referred toherein as HEAT thickeners), and anionic hydrophobically-modified, alkali-soluble or alkali- swellable emulsions (referred to herein as HASE thickeners), and styrene-maleic anhydride terpolymers (SMAT). Preferably they are selected among non-ionic polyurethane, acrylic copolymer dispersion, wax emulsions of vinyl acetate copolymers and bentonite clay non-ionic hydroxyethylcelullose, untreated medium surface fumed silica, mixtures and derivatives thereof.

[0080] Exemplary surfactants or dispersants include anionic, amphoteric and nonionic materials.

[0081] Suitable nonionic surfactants for incorporation into the waterborne latex coating composition include, but are not limited to, compounds of block copolymers based on ethylene oxide and propylene oxide. Other suitable surfactants include nonionic octyl and nonyl phenol ethoxylates, linear and secondary alcohol ethoxylates.

[0082] Suitable anionic surfactants for incorporation into the coating composition include, but are not limited to, sodium dodecyl sulfate (SDS or NaDS), polyacid and poly acid copolymers.

[0083] Other suitable surfactants include phosphate esters made from octyl phenol or nonyl phenol ethoxylates or tridecyl alcohol ethoxylates reacted with an activated phosphoric acid derivative.

[0084] The surfactants are preferably selected from the group consisting of polyoxyethylene tristyrylphenyl ether sulfate ammonium salt, sulfonic acid, sodium lauryl ether sulfate, cetyl trimethyl ammonium chloride, dialkyl dimethyl ammonium chloride, alkyl dimethyl benzyl ammonium chloride, nonyl ethoxylated phenol, coconut fatty acid diethanolamine, coamidopropylbetaine.

[0085] The organic solvents and co-coalescent may be selected from the group consisting of aliphatic hydrocarbon mixtures, butyl glycol, ethyl glycol, hexan, isobutanol, isopropanol, methyl ethyl ketone, n-butanol, naphtha, white mineral oil, kerosene, turpentine, low odor turpentine, toluene, xylene and mixtures thereof.

[0086] In an embodiment, the coating composition comprises, in mass%:

• from 15 to 70% of a liquid carrier, preferably water

• from 2 to 50 % of a polymer,

• from 1 to 70% of a mineral filler,

• from 1 to 30% of a pigment,

• from 0.01 to 2% of an alkalizer agent,

• from 0.1% to 10% of the coalescing agent of the invention (of Formula 1, preferably Formula 1.1 and more preferably Formula 1.2).

[0087] In a further preferred embodiment, the coating composition comprises, in mass%:

• from 20 to 60% of a liquid carrier, preferably water

• from 5 to 45% of a polymer,

• from 2 to 65% of a mineral filler,

• from 2 to 25% of a pigment,

• from 0.05 to 0.5% of an alkalizer agent,

• from 0.2% to 5% of the coalescing agent of the invention (of Formula 1, preferably Formula 1.1 and more preferably Formula 1.2).

[0088] The compositions of any of the embodiments discussed herein are suitable for exterior or interior use.

EXPERIMENTAL PART

[0089] Preparation of the compound of Formula 1.2

[0090] The starting raw material is 1-phenyldodecan-1-one. The preparation ketone has been made as exemplified on p. 69-70 of WO201 8/229285. The lauric acid used to prepare the ketone is biosourced, from coconut fatty acid.

[0091] Synthetic Scheme:

Exact Mass: 260.21 Exact Mass: 262.23 Exact Mass: 304.24

[0092] First reaction : preparation of 1-phenyldodecanol [0093] In a 3 L round bottom flask equipped with a magnetic stirring and a refrigerant are added 200 g (0.768 mol) of 1-phenylhexadecan-1-one followed by 1000 ml of THF and 480 ml of MeOFI. The mixture was allowed to stir at room temperature and 44.0 g (1.152 mol) of NaBFI4 was progressively added to the reaction mixture. The reaction medium was stirred at room temperature during 24 h. The reaction is quenched at 0°C by pouring carefully in the mixture 1000 ml of an aqueous solution of HCI (0.5 M). After removing the TFIF by reduced pressure distillation, 1000 ml of MTBE was added. The organic phase is decanted and then washed 2 times using 700 ml of an aqueous solution of HCI (0.5 M) and finally washed using 700 ml_ of brine. The organic phase is dried over NaS04, filtered and the solvent are removed under vacuum to afford the product. We obtained 204 g of white solid, yield: 100%.

[0094] Second reaction : preparation of 1 -phenyldodecyl acetate [0095] Add triethylamine (273.9 g, 2710mol), 4- dimethylaminopyridine (18.4 g, 0.135 mol), and acetic anhydride (184.2 g, 1.802 mol) to a solution of 1-phenyldodecan-1-ol (354 g, 1.355 mol) in DCM (1000 ml) at 0°C. Stir the reaction mixture at R.T. for 1 h. Quench the reaction mixture with water (1000 ml), extract the reaction mixture with DCM (2^*1000 ml), dried the combined organic extracts over sodium sulfate. Filter the organic extracts, concentrate the residue to get 472 g of colorless liquid, then purified by silica gel column chromatography (100-200 mesh) (PE:DCM=10:1 , PE:DCM=5:1 ,

PE:DCM=3:1 , PE:DCM=2:1 ), concentrated to afford pure product as a colorless liquid.

[0096] Waterbone painting compositions tests

[0097] Several experimental analysis were carried out for waterborne painting compositions comprising as coaslescing agent Diisobutyl adipate Dhaytan AD204 from Solvay (Comparative 1 ), Texanol ® (2,2,4-trimethyl- 1 ,3-pentanediol monoisobutyrate, commercially available from Eastman as Comparative 2) and the compound of formula 1.2 according to the invention as prepared in the previous paragraphs.

[0098] The waterborne painting compositions of the tests comprise, in mass%, 37.16% of water, 33.0% of a styrene-acrylic latex emulsion, 17.5% of titanium dioxide, 6% of kaolin, 4.42% of other additives (including defoamers, biocides, plasticizers, dispersants, surfactants, rheology modifiers, UV absorbers, and thickeners as described above in the specification), 1.65% of coalescent agent and 0.27% of Syco95 (metallic complex of alkali salts) as an alkalizer. Results are shown in Table 1 below:

Table 1

TESTS

[0099] The pH measurements were performed using a DIGIMED DM-20 pH meter.

KU VISCOSITY

[00100] The KU viscosity was evaluated using the following:

• a Krebs Stormer Viscosimeter (model KU-1 );

• a glass thermometer (calibrated);

• a spatula to homogenize;

• a becker of 350 ml, 400 ml or 600 ml; and

• a hot and cold water bath.

[00101] The KU viscosity was evaluated according to the following procedure:

1 - Homogenizing the sample to avoid the formation of bubbles; 2 - Setting the temperature to 25 ± 1 °C

3 - Placing the becker in a movable platform of the viscosimeter in such way that the rotor rod is immersed until the mark in the body thereof;

4 - Pressing the “Power” button to initiate the viscosity measurement;

5 - Reading the measurement from the digital screen of the viscosimeter (measure in Krebs Unity - KU).

CRACKING ANALYSIS

[00102] The cracking analysis was performed using the following:

• a 1000 microns extender;

• an application chart model Leneta 3B or similar;

• suction plate; and

• spatula.

[00103] The cracking analysis was performed according to the following procedure:

1 - Placing the application chart of the suction plate in such a way that the same be adhered to the surface;

2 - Placing the extender of 1000 microns in the top part of the chart and right below place the sample, sufficiently to complete all the length of the extender with a necessary coating layer;

3 - Constantly and uniformly pull the extender, without interruptions;

4 - Making a card for room temperature cooling and making a chart for cooling in a refrigerator;

5 - After completely dried, evaluate the quality of the formed coating layer.

HIDING POWER AND WHITENESS

[00104] The hiding power and whiteness were performed using the following:

• a white card with a black stripe (Leneta form 3B or similar);

• a 10 mils extender; • a spatula;

• a plate with a plan suction surface;

• stove at 70 ± 5 °C; and

• a photospectrometer.

[00105] The hiding power and whiteness were performed according to the following procedure:

1 - Place the card at the suction plate, in such a way that it is kept adhered to the surface;

2 - Placing the 10 mils extender in the top part of the card and right below it place the sample (making sure that there is no product under the extender);

3 - Constantly and uniformly pull the extender, without interruptions to form a film;

4 - Placing it in a stove at 70 ± 5 °C with air circulation for 12 minutes;

5 - After dried, make sure that the film is uniform, i.e. free of defects, wait until it reaches the room temperature;

6 - Measure the film’s contrast in a photospectrometer using the contrast function, making three measurements in different places and making the average thereof.

GLOSS ANALYSIS

[00106] The Gloss 20°, 60° and 85° analysis were performed using the following:

• a Micro - Tri-Gloss 20° - 60° - 85° Gardner Instruments;

• a 10 mils extender;

• an opacity chart type 3B;

• a stove approximately at 70 °C;

• a plate with a suction surface;

[00107] According to the following:

1 - Placing the chart over the suction surface, in such a way that it is kept adhered to the surface; 2 - Placing the 10 mils extender in the top part of the chart and right below place the sample and constantly and uniformly pull the extender, without interruption to form a film;

3 - Dry in stove for 12 minutes. Remove the chart from the stove and allow it to cool. Make three measurements with the Micro - Tri-Gloss in the black part and one in the white part of the chart.

SCRUB ANALYSIS

[00108] The scrub analysis was performed using the following:

• a white card with a black stripe (Leneta form 3B or similar);

• a 10 mils extender;

• a suction plate

• a stove; and

• cleaning sponge.

[00109] The scrub analysis was performed according to the following procedure:

1 - Placing the white card with a black stripe in a plan surface in such a way that it is kept adhered to the surface through suction;

2 - Placing the 10 mils extender in the indicated part of the white card and placing the sample right below it;

3 - Placing it to dry in a stove at 70 ± 2 °C for 12 minutes;

4 - Placing the white card in a plan surface, wetting the cleaning sponge with water and using the abrasive side of the cleaning sponge, perform a uniform abrasive movement over the board from left to right and stopping the movement after seen the board (without coating);

5 - Counting the number of times that the movement was performed; and

6 - Inverting the card upside down and repeating the test.

SYNERESIS ANALYSIS

[00110] The syneresis analysis was performed using the following: a stove with internal circulation at 55 ± 2 °C; a glass container with a metallic lid of appropriate size; a polyethylene plastic film; an inox spatula; a mechanical mixer; and a stainless steel rod.

[00111] The syneresis analysis was performed according to the following procedure:

1 - Homogenizing the sample with the aid of a spatula or mixer and rod;

2 - Washing the glass containers and lids with water and detergent and drying with paper;

3 - measurement the initial viscosity and pH of the sample

4 - Placing a plastic film over the glass container opening and closing it with the lid to avoid vapors to exit;

5 - storing the container in stove for 28 days;

6 - every 7 days, remove the container from the stove, allow it to cool until room temperature at the stand and analyze it for properties change, such as: color and odor, phase separation, formation of superficial liquid and/or decantation;

7 - when no phase separation, homogenize the sample and measure the pH and the viscosity.

COLOR VARIATION

[00112] The color variation (Ae colored) was analyzed using a spectrophotometer X-rite. The Ae colored was obtained was obtained using as baseline the CIELAB color of Syco/Dhaytan with pigment. The results indicate absence of rub out and an increase of color for said composition comprising the compound of Formula 1.2.

[00113] The present invention, therefore, is well adapted to carry out the objects and attain the ends and advantages mentioned, as well as others inherent therein. Although the invention has been depicted and described and is define by reference to particular embodiments, it should be understood that the scope of the present invention encompasses other possible variations, being limited only by the content of the appended claims, including therein the possible equivalents.

Claims

1. Use of a compound having the following Formula 1 :

Formula 1 wherein

Ar is an aryl group which optionally has one or more H atom(s) substituted by functional group(s) and/or by linear or branched alkyl groups,

R is a linear or branched C7-C19 alkyl group or C7-C19 alkenyl group, and

R’ is H or a C1-C4 alkyl group; as coalescing agent in coating compositions.

2. Use according to claim 1, wherein Ar is a phenyl resulting in a compound having the following formula 1.1: o

Formula 1.1 wherein R is a linear or branched C7-C19 alkyl group or C7-C19 alkenyl group, and

R’ is H or a C1-C4 alkyl group.

3. Use according to claim 1 or 2, wherein R’ is a methyl group and R is a C10-C12 linear or branched alkyl group.

4. Use according to any one of claims 1 to 3, wherein R’ is a methyl group and R is a C11 linear alkyl group, resulting in a compound having the following

Formula 1.2:

Formula 1.2.

5. Use according to any one of claims 1 to 4, wherein the coating composition is a paint composition, preferably a waterborne paint composition.

6. Use according to any one of claims 1 to 5, wherein the coating composition comprises a polymer selected from the group consisting of acrylics, (meth)acrylics, vinyls, polyesters, polyurethanes, vinyl acetate ethylene, polybutadiene, polyvinylidene, styrene acrylics, vinyl acrylics, vinyl versatic acid esters, styrene/butadiene, epoxy esters, polysiloxanes, silicones, fluorinated copolymers, and mixtures or copolymers thereof.

7. A coating composition comprising:

• a liquid carrier,

• a polymer, and

• a compound of Formula 1

Formula 1 wherein

R is a linear or branched C7-C19 alkyl group or C7-C19 alkenyl group, and

R’ is H or a C1-C4 alkyl group.

8. The coating composition according to claim 7, wherein in the compound of formula 1 , Ar is a phenyl resulting in a compound having the following formula 1.1 :

R’ is FI or a C1-C4 alkyl group.

9. The coating composition according to claim 7 or 8, wherein in Formula 1 or 1.1 , R’ is a methyl group and R is a C10-C12 linear or branched alkyl group.

10. The coating composition according to any one of claims 7 to 9, wherein in Formula 1 or 1.1 , R’ is a methyl group and R is a C11 linear alkyl group, resulting in a compound having the following Formula 1.2 :

Formula 1.2

11. The coating composition according to any one of claims 7 to 10, wherein the liquid carrier is water.

12. The coating composition according to any one of claims 7 to 11, wherein the polymer is selected from the group consisting of acrylics, (meth)acrylics, vinyls, polyesters, polyurethanes, vinyl acetate ethylene, polybutadiene, polyvinylidene, styrene acrylics, vinyl acrylics, vinyl versatic acid esters, styrene/butadiene, epoxy esters, polysiloxanes, silicones, fluorinated copolymers, and mixtures or copolymers thereof.

13. The coating composition according to any one of claims 7 to 12, further comprising an alkalizer agent, preferably selected from the group consisting of ammonium hydroxide, aqueous solutions of decahydrated borax and sodium hydroxide, and metal complexes of alkaline salts.

14. The coating composition according to any one of claims 7 to 13, further comprising at least one mineral filler, preferably selected from the group consisting of oxides, silicates, carbonates and sulfates, more preferably among clays, aluminum silicate, hydrated aluminum silicate, magnesium silicate, hydrated magnesium silicate, sodium-potassium aluminum silicates, microcrystalline silica, attapulgite, pagodite, mica and kaolin.

15. The coating composition according to claim 14, wherein the mineral filler is kaolin.

16. The coating composition according to any one of claims 7 to 15, further comprising a pigment, wherein the pigment is Ti02.

17. The coating composition according to any one of claims 7 to 16, wherein it comprises in mass%: from 15 to 70% of a liquid carrier, preferably water from 2 to 50 % of a polymer, from 1 to 70% of a mineral filler, from 1 to 30% of a pigment, from 0.01 to 2% of an alkalizer agent, from 0.1 % to 10% of the compound of Formula 1.