Surfactants containing polyol / monool epoxy products, and methods for their preparation, compositions, and methods of use

Abstract

(i) Reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) a reaction product of Reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "Reactant A" to "Reactant B" is about 1:0.5 to about 1:4 is disclosed. Also disclosed are a method for producing the surfactant and a composition containing the surfactant, particularly a coating composition.

Description

Technical Field

[0001] This application relates to a surfactant comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is from about 1:0.5 to about 1:4.

Background Art

[0002] Surfactants are commonly used in coating formulations to promote wetting of the substrate by the coating and wetting of the pigment by the resin. They also increase storage stability by preventing instability of the coating composition when different components are added, and can extend the life of the coating by improving the freedom of formulation. Low amounts of surfactants are often utilized to achieve these objectives, and combinations of surfactants can be specified to impart one or more of the above attributes. Since surfactants are generally non-volatile compounds in the ambient environment, they remain in the coating after drying. At the low levels commonly used, there is little effect on the hardness of the polymer or coating performance. If excessive surfactant is present in an aqueous coating composition, the wet coating may foam excessively or the thickening effect of the thickener may be insufficient, and the cured coating may become water-sensitive, and external durability, block resistance, stain resistance, and print resistance may deteriorate. Therefore, surfactants are usually utilized in the smallest possible amount while avoiding adverse results and achieving their useful properties.

[0003] In the application of coating formulations, the ability to reduce the water surface tension is important because a reduced surface tension generally corresponds to improved wetting of the substrate. Coatings, inks, adhesives, wetting water, cleaning compositions, and agricultural formulations are all examples of aqueous compositions. Surfactants are used to lower the surface tension in aqueous systems, resulting in improved surface coverage, reduced defects, and more uniform dispersions. Equilibrium surface tension performance is important when the system is at rest. The ability of a surfactant to reduce the surface tension and provide wetting under high-speed application conditions (i.e., high surface formation rate) is measured by the dynamic surface tension.

[0004] U.S. Patent No. 7,550,542 discloses a synthetic polymer having a water-soluble or water-swellable polymer backbone and end groups and / or intermediate groups of hydrophobic blocks of alkyl or aryl compounds containing a polymerizable cyclic monomer or polymerizable double bond (or alkene) group or a derivative thereof. The hydrophobic blocks are composed of two or more units of the same or different hydrophobic groups. These synthetic polymers are used as rheology modifiers, especially in latex paints.

[0005] U.S. Patent No. 8,388,806 describes hydrophobically modified poly[ethylene glycol] for use in controlling pitch and tackiness in the pulp and paper processes.

[0006] International Publication No. 2020 / 06554 provides a composition comprising an oil, a surfactant, and optionally a charged polymer complex, and a method for producing the composition. The composition may also include an aqueous phase to provide a microemulsion. The technology further provides a method of using such compositions in home care and personal care.

[0007] Japanese Patent No. 5,659,340 describes a surfactant obtained by reacting 1 mole of a polyoxyalkylene compound containing a polyoxyalkylene compound with 1 to 8 moles of a C6-21 alkyl glycidyl ether.

[0008] Japanese Patent Application Laid-Open No. 2003-253197 describes an antifouling agent containing a crosslinked polymer formed by ring-opening addition polymerization of an epoxy compound selected from the group consisting of monoalcohol glycidyl ethers and polyol glycidyl ethers and a hydroxylated compound selected from the group consisting of monoalcohols, polyols, and polyoxyalkylene compounds obtained by substituting a monoalcohol or polyol with a polyoxyalkylene group.

[0009] Japanese Patent Application Laid-Open No. 2011-088113 describes an emulsifier containing a compound obtained by forming an adduct by reacting (a) a glycidyl ether with (b) a water-soluble polyalkylene glycol having hydroxyl groups at both ends of the molecular chain, and then reacting (c) an organic diisocyanate with the adduct.

[0010] U.S. Patent Application Publication No. 2008 / 0188673 describes an ether alcohol-based low surface tension surfactant and provides its use as a surfactant in an aqueous coating formulation. The surfactant is prepared by reacting at least one hydroxy compound.

[0011] Chinese Patent Application Publication No. 112939898 describes a series of epoxy compounds suitable for casting materials, glass steel plate winding, mold manufacturing, coating, and medical applications, having an epoxy group reacted with a polyester, alkyd resin, or acrylic resin at one end and an ether chain portion at the other end.

Summary of the Invention

[0012] There is a need for a surfactant having high surface activity with respect to pigment dispersibility and wettability, and a surfactant composition effective in lacquer coatings, primer coatings, inkjet printing, top coatings, varnish coatings, and metal or non-metal coatings.

[0013] The present invention relates to an improved surfactant comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4,000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to the molar equivalent of "reactant B" is from about 1:0.5 to about 1:4. The present invention also relates to a method of coating a substrate and a substrate coated with a coating composition of the present invention.

[0014] Accordingly, it is an object of the present invention to provide a surfactant that will provide good equilibrium and dynamic surface tensions and low foaming characteristics and that will be widely acceptable in the coating, ink, adhesive, and agricultural formulation industries.

[0015] The surfactant incorporated into the compositions of the present invention functions as a wetting / dispersing agent to reduce film defects such as fish eyes and craters and improve coating performance.

[0016] The present invention, including the surfactant and its compositions, is used in coating compositions comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4,000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to the molar equivalent of "reactant B" is from about 1:0.5 to about 1:4.

[0017] A main aspect of the present application is to provide a surfactant and its compositions comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4,000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent of "reactant A" to the number of epoxy groups in "reactant B" is from about 1:0.5 to about 1:4.

[0018] In another aspect, the present application provides a surfactant further comprising a reaction product of (i) a reactant B: an epoxy compound having at least one epoxy group per molecule and (ii) a reactant C: an aliphatic alkoxylated alcohol having a weight average molecular weight of about 100 to about 4000.

[0019] In another aspect, the present application provides a reaction product of "reactant A" and "reactant B" comprising (i) about 0.05% to about 40.0% of a polyol monofunctionalized with a glycidyl ether; and (ii) about 60.0% to about 99.95% of a polyol polyfunctionalized with a glycidyl ether.

[0020] In another aspect, the present application provides a method for producing a surfactant, comprising the step of reacting (i) about 1 molar equivalent of an aliphatic polyether polyol and (ii) about 2 molar equivalents of an epoxy compound in the presence of about 0.05 molar equivalent of a base to form a mixture of a polyol monofunctionalized with the epoxy compound and at least one polyol polyfunctionalized with the epoxy compound. In another aspect, the present application provides a reaction product of (i) polyethylene glycol (PEG) having a weight average molecular weight of about 100 to about 4000 and (ii) 2-ethylhexyl glycidyl ether (EHGE), wherein 1 molar equivalent of PEG reacts with 2 molar equivalents of EHGE to form a mixture of PEG monofunctionalized with EHGE, PEG difunctionalized with EHGE, PEG trifunctionalized with EHGE, PEG tetrafunctionalized with EHGE, and PEG pentafunctionalized with EHGE, [Chemical formula] having a general structure represented by each C 11 H 22 O 2 unit is independently [Chemical formula] or [Chemical formula] and, each C 11 H 22 O 2 unit is bonded to the polyethylene glycol core or another C 11 H 22 O 2 unit by a carbon-oxygen single bond, n = 2 to 90, a + b = 1 to 5, PEG mono-functionalized by EHGE where a + b = 1, PEG di-functionalized by EHGE where a + b = 2, PEG tri-functionalized by EHGE where a + b = 3, PEG tetra-functionalized by EHGE where a + b = 4, PEG penta-functionalized by EHGE where a + b = 5, and provides a surfactant comprising a reaction product containing the same.

[0021] In another aspect, the present application is a reaction product of (i) an aliphatic alkoxylated alcohol R-(OCH 2 CHR 1 ) n -OH and (ii) 2-ethylhexyl glycidyl ether (EHGE), wherein 1 molar equivalent of the aliphatic alkoxylated alcohol reacts with 1 molar equivalent of EHGE to form a mixture of an aliphatic alkoxylated alcohol mono-functionalized by EHGE, an aliphatic alkoxylated alcohol di-functionalized by EHGE, an aliphatic alkoxylated alcohol tri-functionalized by EHGE, an aliphatic alkoxylated alcohol tetra-functionalized by EHGE, and an aliphatic alkoxylated alcohol penta-functionalized by EHGE, [Chemical formula] having a general structure represented by, each C 11 H 22 O 2 units are independently, [Chemical formula] or [Chem.] and is such that each C 11 H 22 O 2 unit is bonded to the polyethylene glycol core or another C 11 H 22 O 2 unit by a carbon - oxygen single bond, R is a linear or branched alkyl group having 1 to 20 carbon atoms, R 1 = H and / or CH 3 , n = 1 to 25, a = 1 to 5, a = 1, a monofunctionalized aliphatic alkoxylated alcohol by EHGE, a = 2, a difunctionalized aliphatic alkoxylated alcohol by EHGE, a = 3, a trifunctionalized aliphatic alkoxylated alcohol by EHGE, a = 4, a tetrafunctionalized aliphatic alkoxylated alcohol by EHGE, a = 5, a pentafunctionalized aliphatic alkoxylated alcohol by EHGE, and provides a surfactant comprising a reaction product containing the same.

[0022] In another aspect, the present application provides a composition comprising: (i) a surfactant comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight - average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, and the surfactant is about 5.0 wt% to about 99.5 wt%; and (iii) about 0.5 wt% to about 95.0 wt% of at least one additive.

[0023] In another aspect, the present application provides (i) (a) A reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, further comprising a reaction product of (i) reactant B: an epoxy compound having at least one epoxy group per molecule and (ii) reactant C: an aliphatic alkoxylated alcohol having a weight average molecular weight of about 100 to about 4000, a surfactant of about 5.0 wt% to about 99.5 wt%; and (b) Provided is a composition comprising about 0.5 wt% to about 95.0 wt% of at least one additive.

[0024] In another aspect, the present application provides a coating composition comprising (i) a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, a surfactant of about 0.1 wt% to about 5.0 wt%; (iii) at least one film-forming polymer of about 5.0 wt% to about 85.0 wt%; and (iv) at least one additive of about 10.0 wt% to about 94.9 wt%.

[0025] In another aspect, the present application (I) (a) A reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, and (b) a reaction product of (i) reactant B: an epoxy compound having at least one epoxy group per molecule and (ii) reactant C: an aliphatic alkoxylated alcohol having a weight average molecular weight of about 100 to about 4000, a surfactant of about 0.1 wt% to about 5.0 wt%; (II) From about 5.0 wt% to about 85.0 wt% of at least one film-forming polymer; and (III) From about 10.0 wt% to about 94.9 wt% of at least one additive to provide a coating composition. **DETAILED DESCRIPTION OF THE INVENTION**

[0026] Before describing in detail at least one aspect of the disclosed and / or claimed inventive concept, it is to be understood that the disclosed and / or claimed inventive concept is not limited in its application to the details of construction or arrangement of components or steps or methodology set forth in the following description or shown in the drawings. The disclosed and / or claimed inventive concept may have other aspects or may be practiced or carried out in various ways. Also, it is to be understood that the expressions and terms used herein are for the purpose of description and should not be regarded as limiting.

[0027] Unless otherwise defined herein, technical terms used in connection with the disclosed and / or claimed inventive concept shall have the meanings generally understood by those skilled in the art. Further, unless the context requires otherwise, singular terms shall include pluralities and plural terms shall include singulars.

[0028] The singular forms "a", "an", and "the" include pluralities unless otherwise specified or unless the contrary is clearly implied by the context. The terms "comprising" and "comprised of" include the more limiting meanings of "consisting essentially of" and "consisting of".

[0029] For the purposes of the following detailed description, unless otherwise indicated, for example, in the case of any examples other than the specific ones, or as otherwise shown, all numbers representing amounts of components used in this specification and the claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in this specification and the appended claims are approximations that may vary depending upon the desired properties sought to be obtained when practicing the invention.

[0030] All percentages, parts, ratios, and proportions used herein are by weight of the total composition, unless otherwise specified. All weights related to the components described are based on the active level, and thus solvents or by-products that may be contained in commercially available materials are not included, unless otherwise specified.

[0031] All publications, articles, papers, patents, patent publications, and other references cited herein are hereby incorporated by reference in their entirety for all purposes to the extent consistent with the disclosure of this specification.

[0032] As used in this disclosure, unless otherwise indicated, the following terms are to be understood as having the following meanings.

[0033] The term "at least one" is understood to include one and any amount 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" can extend up to 100 or 1000 or more, depending on the term to which it is attached. Further, the amounts of 100 / 1000 are not to be regarded as limiting the lower or upper limits.

[0034] As used herein, the terms "comprising" (and any form thereof), "having" (and any form thereof), "including" (and any form thereof), or "contain" (and any form thereof) are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.

[0035] As used herein, the term "surfactant" refers to any amphiphilic molecule that reduces surface tension when added to water.

[0036] As used herein, the term "moiety (moieties)" refers to a part or functional group of a molecule.

[0037] The term "substituted" means that a particular group or moiety has one or more substituents.

[0038] The term "functionalized" refers to the presence of one or more functional groups in any moiety. Various functional groups can be introduced into a moiety by one or more functionalization reactions known to those skilled in the art. It should be understood that an alcohol or polyol "functionalized" with an epoxy compound or glycidyl ether has reacted such that at least one hydroxyl group of the alcohol or polyol forms an ether bond with one of the carbon atoms of the epoxide group of the epoxy compound or glycidyl ether, and at least one epoxide group of the epoxy compound or glycidyl ether has opened upon attack by the alcohol or polyol to form a new hydroxyl group.

[0039] As used herein, the term "aliphatic polyether polyol" refers to reactant A which is a polyether having two or more hydroxyl groups and a molecular weight of about 100 to about 4000. Examples of aliphatic polyether polyols include oligomers, polymers and copolymers of ethylene oxide, propylene oxide and butylene oxide, polyethylene glycol, polypropylene glycol, poly(trimethylene oxide) glycol, and polytetramethylene ether glycol. In a preferred embodiment, the aliphatic polyether polyol is polyethylene glycol.

[0040] In one non-limiting embodiment, the "aliphatic polyether polyol" is a polyethylene glycol selected from the group consisting of PEG 100, PEG 200, PEG 300, PEG 400, PEG 500, PEG 600, PEG 700, PEG 800, PEG 900, PEG 1000, PEG 1100, PEG 1200, PEG 1300, PEG 1400, PEG 1500, PEG 1600, PEG 1700, PEG 1800, PEG 1900, PEG 2000, PEG 2100, PEG 2200, PEG 2300, PEG 2400, PEG 2500, PEG 2600, PEG 2700, PEG 2800, PEG 2900, PEG 3000, PEG 3100, PEG 3200, PEG 3300, PEG 3400, PEG 3500, PEG 3600, PEG 3700, PEG 3800, PEG 3900, and PEG 4000.

[0041] In a non-limiting embodiment, the epoxy compound used as reactant B in the present invention is an alkyl glycidyl ether in which the alkyl group is a saturated or unsaturated linear or branched aliphatic hydrocarbyl group having 3 to 24 carbon atoms. According to another non-limiting embodiment of the present application, the epoxy compound is n-butyl glycidyl ether, n-octyl glycidyl ether, n-decyl glycidyl ether, n-dodecyl glycidyl ether, n-tetradecyl glycidyl ether, n-hexadecyl glycidyl ether, n-octadecyl glycidyl ether, n-octadecenyl glycidyl ether (oleyl glycidyl ether), docosyl glycidyl ether and other primary linear alkyl glycidyl ethers; 2-ethylhexyl glycidyl ether, 2-hexyldecyl glycidyl ether, 2-octyldodecyl glycidyl ether, 2-heptylundecyl glycidyl ether, 2-(1,3,3-trimethylbutyl) octyl glycidyl ether, 2-decyltetradecyl glycidyl ether, 2-dodecylhexadecyl glycidyl ether, 2-tetradecyloctadecyl glycidyl ether and other primary branched alkyl glycidyl ethers; secondary alkyl glycidyl ethers such as sec-decyl glycidyl ether, sec-octyl glycidyl ether, sec-dodecyl glycidyl ether; or tertiary alkyl glycidyl ethers such as t-octyl glycidyl ether, t-dodecyl glycidyl ether.

[0042] As used herein, the term "aliphatic alkoxylated alcohol" refers to reactant C, a substance having the following structure.

Chemical formula

[0043] In a non-limiting embodiment, the "aliphatic alkoxylated alcohol" is C 6-20It contains an alcohol ethoxylate selected from the group consisting of alcohol ethoxylates (3 - 23 EO). Examples of such surfactants can be obtained from BASF (LUTENSOL ( Registered Trademark ) ), and can also be obtained from Sasol Performance Chemicals (NOVEL (Registered Trademark)).

[0044] In another non - limiting embodiment, the present application discloses a method for producing a surfactant, which comprises reacting (i) about 1 molar equivalent of an aliphatic polyether polyol with (ii) about 2 molar equivalents of an alkyl glycidyl ether in the presence of about 0.05 molar equivalent of a base to form a mixture of a polyol monofunctionalized with an alkyl glycidyl ether and at least one polyol polyfunctionalized with an alkyl glycidyl ether. Here, the reaction is carried out at a temperature of about 80 °C to about 120 °C in the presence of (i) an amine selected from the group including but not limited to triethylamine, 4 - (dimethylamino)pyridine, and 1,1,3,3 - tetramethylguanidine; and (ii) a base selected from the group consisting of oxides, hydroxides, carbonates, and bicarbonates of sodium, potassium, and calcium, and combinations thereof.

[0045] In another non - limiting embodiment, the present application discloses the reaction of (i) polyethylene glycol and (ii) 2 - ethylhexyl glycidyl ether, where the molar equivalent ratio of polyethylene glycol to 2 - ethylhexyl glycidyl ether is about 1:0.5 to about 1:4.

[0046] In another non-limiting embodiment, the present application discloses a method for producing a surfactant, comprising reacting (i) about 1 molar equivalent of an aliphatic polyether polyol with (ii) about 2 molar equivalents of an epoxy compound in the presence of about 0.05 molar equivalent of a base to form a mixture of a polyol monofunctionalized by the epoxy compound and at least one polyol polyfunctionalized by the epoxy compound. Here, the reaction is carried out at a temperature of about 80°C to about 120°C in the presence of (i) an amine selected from the group consisting of, but not limited to, triethylamine, 4-(dimethylamino)pyridine, and 1,1,3,3-tetramethylguanidine; and (ii) a base selected from the group consisting of oxides, hydroxides, carbonates, and bicarbonates of sodium, potassium, and calcium, and combinations thereof.

[0047] In another non-limiting embodiment, the present application discloses that the molar equivalent ratio of polyethylene glycol to 2-ethylhexyl glycidyl ether is about 1:0.5 to about 1:4.

[0048] In another embodiment, the present application discloses a surfactant comprising a polyol monofunctionalized by an alkyl glycidyl ether present in an amount of about 0.05% to about 0.5%; or about 0.5 wt% to about 1 wt%; or about 1 wt% to about 2.5 wt%; or about 2.5 wt% to about 5 wt%; or about 5 wt% to about 10 wt%; or about 10 wt% to about 15 wt%; or about 15 wt% to about 20 wt%; or about 20 wt% to about 25 wt%; or about 25 wt% to about 30 wt%; or about 30 wt% to about 35 wt%; or about 35 wt% to about 40 wt%, and a polyol polyfunctionalized by an alkyl glycidyl ether present in an amount of about 60 wt% to about 65 wt%; or about 65 wt% to about 70 wt%; or about 70 wt% to about 75 wt%; or about 75 wt% to about 80 wt%; or about 80 wt% to about 85 wt%; or about 85 wt% to about 90 wt%; or about 90 wt% to about 95 wt%; or about 95 wt% to about 99.5 wt%.

[0049] In one embodiment, the present application is a reaction product of (i) reactant A: polyethylene glycol (PEG) having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: 2-ethylhexyl glycidyl ether (EHGE), wherein 1 molar equivalent of PEG reacts with 2 molar equivalents of EHGE to form a mixture of PEG monofunctionalized by EHGE, PEG difunctionalized by EHGE, PEG trifunctionalized by EHGE, PEG tetrafunctionalized by EHGE, and PEG pentafunctionalized by EHGE,

Chemical formula

Chemical formula

Chemical formula

[0050] In another embodiment, the present application is (i) an aliphatic alkoxylated alcohol R-(OCH 2 CHR 1 ) nThe reaction product of (i) -OH and (ii) 2-ethylhexyl glycidyl ether (EHGE), wherein 1 molar equivalent of an aliphatic alkoxylated alcohol reacts with 1 molar equivalent of EHGE to form a mixture of an aliphatic alkoxylated alcohol monofunctionalized by EHGE, an aliphatic alkoxylated alcohol difunctionalized by EHGE, an aliphatic alkoxylated alcohol trifunctionalized by EHGE, an aliphatic alkoxylated alcohol tetrafunctionalized by EHGE, and an aliphatic alkoxylated alcohol pentafunctionalized by EHGE,

Chemical formula

Chemical formula

Chemical formula

[0051] In one embodiment, the present application provides a composition comprising: (i) a surfactant comprising a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, and the surfactant is present in an amount of about 5.0 wt% to about 99.5 wt%; and (iii) at least one additive in an amount of about 0.5 wt% to about 95.0 wt%.

[0052] In one embodiment, the present application provides a composition comprising: (i)(a) a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, and further comprising a reaction product of (i) reactant B: an epoxy compound having at least one epoxy group per molecule and (ii) reactant C: an aliphatic alkoxylated alcohol having a weight average molecular weight of about 100 to about 4000, and the surfactant is present in an amount of about 5.0 wt% to about 99.5 wt%; and (b) at least one additive in an amount of about 0.5 wt% to about 95.0 wt%.

[0053] In another aspect, the present application discloses a coating composition comprising: (i) a surfactant in an amount of about 0.1 wt% to about 5.0 wt%, which is a reaction product of (a) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4,000 and (b) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4; (ii) at least one film-forming polymer in an amount of about 5.0 wt% to about 85.0 wt%; and (iii) at least one additive in an amount of about 10.0 wt% to about 94.9 wt%.

[0054] In another aspect, the present application discloses (I) A surfactant in an amount of about 0.1 wt% to about 5.0 wt%, comprising (a) a reaction product of (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4,000 and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the molar equivalent ratio of "reactant A" to "reactant B" is about 1:0.5 to about 1:4, and (b) a reaction product of (i) reactant B: an epoxy compound having at least one epoxy group per molecule and (ii) reactant C: an aliphatic alkoxylated alcohol having a weight average molecular weight of about 100 to about 4,000; (II) at least one film-forming polymer in an amount of about 5.0 wt% to about 85.0 wt%; and (III) a coating composition comprising at least one additive in an amount of about 10.0 wt% to about 94.9 wt%.

[0055] According to another embodiment of the present application, the composition containing the surfactant of the present invention is used in various coating applications including, but not limited to, paper products, metal coatings, architectural coatings, graphic arts, fibrous materials, films, sheets, composites, printing inks, inkjet printing, flocks and other adhesives, hair care products, skin care products, nail care products, household products, livestock / agriculture, wood coatings, textile products, non-woven coatings, and seed applications.

[0056] In one embodiment, the present application discloses a composition comprising at least one additive selected from the group consisting of a flocculant, a film-forming agent, an emulsifier, a stabilizer, a rheology modifier, a co-solvent, a dispersant, a defoamer, wet-edge additives, a wetting agent, a humectant, a wax, a colorant, a thickener, an anti-curing agent, an anti-foaming agent, an ultraviolet absorber, a pigment, an anti-freezing agent, a gel inhibitor, a preservative, a hydrophobic agent, an adhesion promoter, an insecticide, an antioxidant, and a plasticizer.

[0057] In another embodiment, the present application discloses that the molecular weight of the aliphatic alkoxylated alcohol ranges from about 100 to about 4000 Daltons. In some embodiments, the molecular weight of the aliphatic alkoxylated alcohol ranges from about 100 to about 200 Daltons; or from about 200 to about 300 Daltons; or from about 300 to about 400 Daltons; or from about 400 to about 500 Daltons; or from about 500 to about 600 Daltons; or from about 600 to about 700 Daltons; or from about 700 to about 800 Daltons; or from about 800 to about 900 Daltons; or from about 900 to about 1000 Daltons; or from about 1000 to about 1500 Daltons; or from about 1500 to about 2000 Daltons; or from about 2000 to about 2500 Daltons; or from about 2500 to about 3000 Daltons; or from about 3000 to about 3500 Daltons; or from about 3500 to about 4000 Daltons.

[0058] In another embodiment, the present application discloses that the composition contains a surfactant in an amount of about 5 wt% to about 10 wt%; or about 10 wt% to about 15 wt%; or about 15 wt% to about 20 wt%; or about 20 wt% to about 25 wt%; or about 25 wt% to about 30 wt%; or about 30 wt% to about 35 wt%; or about 35 wt% to about 40 wt%; or about 40 wt% to about 45 wt%; or about 45 wt% to about 50 wt%; or about 50 wt% to about 55 wt%; or about 55 wt% to about 60 wt%; or about 60 wt% to about 65 wt%; or about 65 wt% to about 70 wt%; or about 70 wt% to about 75 wt%; or about 75 wt% to about 80 wt%; or about 80 wt% to about 85 wt%; or about 85 wt% to about 90 wt%; or about 90 wt% to about 95 wt%; or about 95 wt% to about 99.5 wt%.

[0059] In another embodiment, the present application discloses that in a composition containing one or more additives, the additive is present in an amount of about 0.5 wt% to about 1 wt%; or about 1 wt% to about 2.5 wt%; or about 2.5 wt% to about 5 wt%; or about 5 wt% to about 10 wt%; or about 10 wt% to about 15 wt%; or about 15 wt% to about 20 wt%; or about 20 wt% to about 25 wt%; or about 25 wt% to about 30 wt%; or about 30 wt% to about 35 wt%; or about 35 wt% to about 40 wt%; or about 40 wt% to about 45 wt%; or about 45 wt% to about 50 wt%; or about 50 wt% to about 55 wt%; or about 55 wt% to about 60 wt%; or about 60 wt% to about 65 wt%; or about 65 wt% to about 70 wt%; or about 70 wt% to about 75 wt%; or about 75 wt% to about 80 wt%; or about 80 wt% to about 85 wt%; or about 85 wt% to about 90 wt%; or about 90 wt% to about 95 wt% based on the total weight of the composition.

[0060] In another embodiment, the present application discloses that the coating composition contains a surfactant in an amount of about 0.1 wt% to about 0.2 wt%; or about 0.2 wt% to about 0.3 wt%; or about 0.3 wt% to about 0.4 wt%; or about 0.4 wt% to about 0.5 wt%; about 0.5 wt% to about 0.6 wt%; about 0.6 wt% to about 0.7 wt%; about 0.7 wt% to about 0.8 wt%; about 0.8 wt% to about 0.9 wt%; about 0.9 wt% to about 1.0 wt%; about 1.0 wt% to about 2 wt%; or about 2.0 wt% to about 3.0 wt%; about 3.0 wt% to about 4.0 wt%; or about 4.0 wt% to about 5.0 wt% based on the total weight of the composition.

[0061] In another non-limiting embodiment, the present application discloses that the coating composition contains a film-forming polymer in an amount of about 5 wt% to about 10 wt%; about 10 wt% to about 15 wt%; or about 15 wt% to about 20 wt%; or about 20 wt% to about 25 wt%; or about 25 wt% to about 30 wt%; or about 30 wt% to about 35 wt%; or about 35 wt% to about 40 wt%; or about 40 wt% to about 45 wt%; or about 45 wt% to about 50 wt%; or about 50 wt% to about 55 wt%; or about 55 wt% to about 60 wt%; or about 60 wt% to about 65 wt%; or about 65 wt% to about 70 wt%; or about 70 wt% to about 75 wt%; or about 75 wt% to about 80 wt%; or about 80 wt% to about 85 wt% based on the total weight of the coating composition.

[0062] In another embodiment, the present application discloses that the coating composition contains one or more additives in an amount of about 10% to about 15% by weight; or about 15% to about 20% by weight; or about 20% to about 25% by weight; or about 25% to about 30% by weight; or about 30% to about 35% by weight; or about 35% to about 40% by weight; or about 40% to about 45% by weight; or about 45% to about 50% by weight; or about 50% to about 55% by weight; or about 55% to about 60% by weight; or about 60% to about 65% by weight; or about 65% to about 70% by weight; or about 70% to about 75% by weight; about 75% to about 80% by weight; or about 80% to about 85% by weight; or about 85% to about 90% by weight; or about 90% to about 94.9% by weight based on the total weight of the coating composition.

[0063] In another embodiment of the present application, the coating composition containing the aggregating agent can include, but is not limited to, ester alcohol, benzoate ether, glycol ether, glycol ether ester, and n-methyl-2-pyrrolidone.

[0064] In another embodiment of the present application, in a composition containing an emulsifier, the emulsifier is selected from an anionic emulsifier such as mono-, di- or triethanolamine oleate, stearate, diethylethanolamine oleate, stearate, 2-amino-2-methylpropane-1-ol stearate, sulfonated compounds (such as sodium dodecyl sulfate, Turkey red oil, etc.) and sulfonated compounds (such as sodium cetylsulfonate), a cationic emulsifier such as a quaternary ammonium compound (such as cetyltrimethylammonium bromide, benzyl lauryldimethylammonium chloride, etc.), an amphoteric emulsifier (such as lecithin) and a nonionic emulsifier such as a fatty alcohol (lauryl alcohol, cetyl alcohol, stearyl alcohol or palmityl alcohol), a partial fatty acid ester of a saturated fatty acid and a polyhydric alcohol (glycerol monostearate, pentaerythritol monostearate, ethylene glycol monostearate, propylene glycol monostearate), a partial fatty acid ester of an unsaturated fatty acid and a polyhydric alcohol (such as glycerol monooleate, pentaerythritol monooleate), a polyoxyethylene ester of a fatty acid (such as polyoxyethylene stearate), a polymerization product of ethylene oxide and propylene oxide and a fatty alcohol (fatty alcohol polyglycol ether) or a polymerization product of ethylene oxide and propylene oxide and a fatty acid (fatty acid ethoxylate).

[0065] In one embodiment, the present application discloses a composition containing a suitable rheology modifier for controlling viscosity over a wide shear rate range. Further, the coating compound contains a rheology modifier such as particulate silica, layered silicate, or a polymer cellulose-based compound, and a nonionic synthetic associative thickeners (NSAT’s) compound.

[0066] Suitable dispersants for use in the composition include, but are not limited to, nonionic dispersants, anionic dispersants, and cationic dispersants, such as 2-amino-2-methyl-1-propanol (AMP), dimethylaminoethanol (DMAE), potassium tripolyphosphate (KTPP), trisodium polyphosphate (TSPP), citric acid, and other carboxylic acids. Also, dispersants suitable for the composition of the present invention are anionic polymers such as polycarboxylic acid-based homopolymers and copolymers, including those hydrophobized, such as polyacrylic acid or polymethacrylic acid or maleic anhydride having monomers such as styrene, acrylate or methacrylate, isobutylene, and other hydrophilic or hydrophobic comonomers, as well as salts of the above dispersants, and mixtures thereof.

[0067] To prevent evaporation of water in the composition before the coating is completely dry, a suitable humectant can be added. Examples of such humectants are ethylene glycol, glycerin, and polyethylene glycol.

[0068] Suitable defoamers in the composition include silicone-based defoamers and mineral oil-based defoamers.

[0069] In another embodiment of the present application, a composition containing an anti-foaming agent can include, but is not limited to, animal oil and vegetable oil type anti-foaming agents, fatty acid type anti-foaming agents, nonionic anti-foaming agents (polyether anti-foaming agents), acetylene diol anti-foaming agents, fluorine anti-foaming agents, silicone anti-foaming agents, mineral oil anti-foaming agents, and phosphate ester anti-foaming agents.

[0070] In another embodiment of the present application, a thickening agent is added to the composition to achieve the desired viscosity and flow characteristics. The thickening agent can include, but is not limited to, cellulose derivatives including hydroxyethyl cellulose, methyl cellulose, and carboxymethyl cellulose, and can be used in the composition.

[0071] Suitable thickeners include, but are not limited to, polyvinyl alcohol (PVA), hydrophobized alkali-soluble emulsions known in the art as HASE emulsions, alkali-soluble or alkali-swellable emulsions known in the art as ASE emulsions, hydrophobized ethylene oxide-urethane polymers known in the art as HEUR thickeners, and cellulose-based thickeners such as hydroxymethyl cellulose (HMC), hydroxyethyl cellulose (HEC), hydrophobized hydroxyethyl 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-hydroxypropyl cellulose, etc. Also useful as thickeners are fumed silica, attapulgite clay and other types of clay, titanate chelating agents, etc.

[0072] "Antifreezing agent" refers to an additive that prevents freezing. Suitable antifreezing agents include, but are not limited to, alcohols, polyols such as glycerol, glycols such as propylene glycol, and polyol fatty acid esters, or derivatives thereof.

[0073] To prevent the growth of microorganisms, one or more preservatives may be added in a low amount to the composition. Preservatives include, but are not limited to, 2-methyl-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-propynyl butylcarbamate (IPBC), oxyfluorfen, thiabendazole, terbutryn, zinc pyrithione (ZnPy). Suitable fungicides and insecticides in the composition include zinc oxide, isothiazolone, triazole.

[0074] 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 acrylic and / or methacrylic, polymers or copolymers, polyvinyl acetate, styrene-acrylic copolymer, styrene-butadiene copolymer, vinyl acetate-acrylic copolymer, ethylene-vinyl acetate copolymer, vinyl acetate-versatate copolymer, vinyl acetate-vinyl maleate copolymer, vinyl acetate-vinyl chloride-acrylic terpolymer, ethylene-vinyl acetate-acrylic terpolymer, and urethane polymers. These polymers can contain, up to about 10% by weight, monomers containing functional groups such as carboxylic acid groups, phosphate groups, sulfate groups, sulfonic acid groups and amide groups, other monomers and mixtures thereof.

[0075] The compositions of the present disclosure can further include at least one pigment. The pigment can be selected from the group consisting of phthalocyanine, iron oxide, titanium dioxide, zinc oxide, indigo, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silica, talc, calcium carbonate, and mixtures thereof. The grade of titanium dioxide used in the composition is surface modified with inorganic oxides such as silicates, aluminates, and zirconates. Aluminum silicate, nepheline syenite, mica, calcium carbonate, and / or diatomaceous earth can also be used.

[0076] The compositions of the present disclosure can further include at least one film-forming polymer. The film-forming polymers of the present disclosure can be selected from a wide variety of polymers known in the relevant art. For example, these film-forming polymers can be derived from various unsaturated monomers such as ethylene monomers, vinyl monomers, and acrylic monomers. Examples of such monomers include, but are not limited to, acrylic acid, methacrylic acid, methacrylate esters, styrene, α-methylstyrene, vinyl chloride, acrylonitrile, methacrylonitrile, ureidomethacrylate, vinyl acetate, vinyl esters of branched tertiary monocarboxylic acids, itaconic acid, crotonic acid, maleic acid, fumaric acid, and ethylene. It can also contain C 4 -C 8 conjugated dienes such as 1,3-butadiene, isoprene and chloroprene. The film-forming polymer can also be a copolymer product of two or more monomers to achieve some desired properties, especially for use in latex paints with little or no volatile organic compounds (VOC). Examples of suitable film-forming polymers include, but are not limited to, homopolymers or copolymers of vinyl acetate, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, butyl acrylate, styrene, ethylene, vinyl chloride, vinyl esters of neodecanoic acid, vinyl propionate, butadiene, acrylonitrile, marieate, and fumarate. In a non-limiting embodiment of the present disclosure, the film-forming polymer is selected from the group consisting of acrylic, vinyl acrylic and styrene acrylic, styrene-butadiene copolymer, vinyl acetate ethylene, butadiene-acrylonitrile copolymer, polyepoxide, polyurethane, polyamide, vinyl esters of neodecanoic acid and polyester.

[0077] Examples of other suitable film-forming polymers include, but are not limited to, alkyds, celluloses (nitrocellulose and cellulose esters), coumarone-indene, epoxy, ester, hydrocarbon, melamine, natural resins, oleoresins, phenol, polyamide, polyester, rosin, silicone, terpene, urea, and urethane.

[0078] Small amounts, i.e., less than about 10 wt% based on the total weight of the composition, of additives can be included. Such additives include co-solvents, wet edge additives, wetting agents, waxes, colorants, anti-setoff agents, UV absorbers, gel inhibitors, hydrophobic agents, and antioxidants.

[0079] In one embodiment, the present application discloses coating compositions for use in lacquer coatings, primer coatings, inkjet printing, top coatings, varnish coatings, architectural coatings, wood coatings, printing inks, and coatings for metal or non-metal coatings.

[0080] Coating compositions in the form of paints can include enamels, lacquers, varnishes, undercoats, primers, sealers, fillers, stoppers, and the like.

[0081] In one embodiment, the present application discloses a coating composition coated on a substrate selected from the group consisting of porous and non-porous substrates, paper, non-woven materials, textiles, leather, wood, concrete, masonry, metal, non-metal, housewrap, building materials, fiberglass, polymer articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, airbags, fabrics, ceramics, yarns, and blends, woven substrates, non-woven substrates, knitted substrates, natural substrates, synthetic substrates, and recycled substrates.

[0082] Furthermore, specific embodiments of the present application are described in detail by the following examples. The examples are provided herein for the purpose of illustrating the present application and are not intended to be limiting.

Example

[0083] Synthesis scheme reaction of PEG and EHGE

Chem.

Chem.

Chem.

[0084] Experimental procedure 1 (batch procedure) The reaction of PEG and EHGE was carried out using the following one-pot procedure. That is, polyethylene glycol, 2-ethylhexyl glycidyl ether, and potassium hydroxide were combined in a container, which was sealed and maintained under a nitrogen atmosphere. The reaction mixture was stirred and heated at 100 °C for 7 to 19 hours, and then cooled to room temperature. The following examples were carried out using this procedure.

[0085] Example 1: The reaction of PEG 400 (28.50 g), 2-ethylhexyl glycidyl ether (6.64 g), and potassium hydroxide (200 mg) was carried out at 100 °C for 19 hours according to Experimental Procedure 1.

[0086] Example 2: The reaction of PEG 400 (11.00 g), 2-ethylhexyl glycidyl ether (20.49 g), and potassium hydroxide (77 mg) was carried out at 100 °C for 19 hours according to Experimental Procedure 1.

[0087] Example 4: The reaction of PEG 300 (111.51 g), 2-ethylhexyl glycidyl ether (138.49 g), and potassium hydroxide (1.043 g) was carried out at 100 °C for 7 hours according to Experimental Procedure 1.

[0088] Experimental Procedure 2 (Slow addition procedure) The reaction of PEG and EHGE was carried out using the following slow addition procedure. That is, polyethylene glycol and potassium hydroxide were combined in a container, which was sealed and maintained under a nitrogen atmosphere. The reaction mixture was stirred and heated to 100 °C. Once the temperature reached 100 °C, 2-ethylhexyl glycidyl ether was slowly added over approximately 1 hour. The reaction mixture was stirred at 100 °C for 30 minutes, then stirred at 120 °C for 3 to 3.5 hours, and then cooled to room temperature. The following examples were carried out using this procedure.

[0089] Example 3: The reaction of PEG 200 (87.00 g), 2-ethylhexyl glycidyl ether (162.07 g), and potassium hydroxide (1.22 g) was carried out according to Experimental Procedure 2.

[0090] Example 5: The reaction of PEG 400 (520.00 g), 2-ethylhexyl glycidyl ether (484.35 g), and potassium hydroxide (3.65 g) was carried out according to Experimental Procedure 2.

[0091] Example 6: The reaction of PEG 600 (160.00 g), 2-ethylhexyl glycidyl ether (99.35 g), and potassium hydroxide (748 mg) was carried out according to Experimental Procedure 2.

[0092] Example 7: The reaction of PEG 1000 (190.00 g), 2-ethylhexyl glycidyl ether (70.79 g), and potassium hydroxide (533 mg) was carried out according to Experimental Procedure 2.

[0093] Example 8: The reaction of PEG 2000 (210.50 g), 2-ethylhexyl glycidyl ether (39.21 g), and potassium hydroxide (398 mg) was carried out according to Experimental Procedure 2.

[0094] Example 9: The reaction of PEG 4000 (228.50 g), 2-ethylhexyl glycidyl ether (21.28 g), and potassium hydroxide (396 mg) was carried out according to Experimental Procedure 2.

[0095] LCMS: Using LCMS, the mixture of substituted PEGs was separated and the relative abundances of various PEGs with different degrees of substitution were determined. The respective peaks corresponding to unsubstituted PEG, mono-substituted PEG, di-substituted PEG, tri-substituted PEG, and tetra-substituted PEG were well separated by HPLC and thus were reliably integrated.

[0096] Procedure: Approximately 0.1 g of each sample was combined with 10 mL of methanol and vortexed until the resulting stock solution was homogeneous. For LCMS analysis, 100 μL of the stock solution was diluted with 900 μL of methanol, and the resulting solution was injected directly into the system. LCMS analysis was performed on an Agilent 6520 QTOF LC / MS using an Agilent 1260 HPLC and MassHunter software.

[0097] HPLC conditions:

Table 1

Table 2

[0098] Table 1 shows the product distributions determined for the reaction products of Examples 1 - 7.

Table 3

[0099] Measurement of the contact angle, static and dynamic surface tension, and foaming of the surfactant:

[0100] Solution preparation: An aqueous solution of the surfactant was prepared by combining 1 g of the adduct with 1000 g of DI water (filtered Millipore - Q, pH 6.3 - 6.7) at room temperature. Before measurement, the resulting solution was mixed for 24 hours using a magnetic stirrer. The solution pH value of the selected sample was measured to be approximately 7.4.

[0101] Contact angle measurement: A transparent self - adhesive 0.002 - inch thick polypropylene film (McMaster - Carr # 5577149 - 01) was used as the substrate, and the contact angle of a 0.1 wt% aqueous solution of the surfactant was measured.

[0102] The contact angle values between the sample droplets and the polypropylene surface were determined using a Kruss Drop Shape Analysis System DSA 305. The sample droplets were automatically dropped using a disposable 1 mL syringe. The contact angle of each droplet was automatically measured using the fitting model software of the apparatus (Kruss Advance Drop Shape V 1.5.1) and recorded every second for 30 seconds. A plurality of droplets were placed at a sufficient distance on the pre-cleaned polypropylene surface. The results were obtained as average values. At least 6 droplets were analyzed for each sample. All measurements were carried out at ambient temperature and relative humidity.

[0103] Static surface tension measurement: The static surface tension values of the freshly mixed 0.1 wt% aqueous surfactant solution were measured at room temperature by the Wilhelmy Plate method based on the recommendations of the equipment company (in accordance with ASTM D1331-20) using a force tensiometer (Attension, Biolin Scientific). Three surface tension measurement values were recorded for each sample and the average value was obtained. Before each measurement, the Wilhelmy plate was rinsed and subjected to pyrolysis treatment by flame. The calibration of the apparatus was checked by measuring the surface tension of DI water at the start of the measurement.

[0104] Dynamic surface tension measurement: The dynamic surface tension of the freshly mixed 0.1 wt% aqueous surfactant solution with a surface lifetime between 10 milliseconds and 100,000 milliseconds was measured using a hydrophobic-coated glass capillary with a diameter of 0.256 mm by a bubble pressure tensiometer (Kruss, model BP2). The capillary was cleaned between samples using a detergent solution, then rinsed with DI water and then dried with a Kimwipe. Before the experimental measurement, the calibration of the apparatus was checked by measuring the surface tension of DI water.

[0105] Determination of the foaming index: The foaming behavior of the surfactant was evaluated using the SITA Messtechnik foaming tester R-2000. Approximately 900 mL of freshly mixed 0.1 wt% solution was filled into the reservoir of the apparatus, and the test parameters were input using the software of the apparatus. Each sample was tested three times at room temperature. To foam, 250 mL of the solution was filled into a cylindrical glass container and mixed with a bottom propeller at 800 rpm for 10 seconds. After the mixing cycle, the height of the foam formed on top of the liquid was measured by the conductivity probe of the apparatus, and the foam volume was recorded in mL units by the software of the apparatus. This process was repeated 30 times, and the cumulative foaming was recorded for 30 consecutive mixing steps. After completing three runs for each sample, the average foam volume for each mixing step was calculated. The foaming index was defined as the total foam volume at the end of 30 mixing steps and was calculated by summing the average values of the foam volume for each mixing step using Excel software (Table 2).

Table 4

[0106] Coating formulations were prepared using the binder resins shown in Table 3. Binder No. 3 was prepared by diluting Neocryl XK-98 with DI water to a solids content of 33%.

Table 5

[0107] Coating formulations consisting of binder resin, butyl carbitol (BC) as a co-solvent, and a transparent red iron oxide pigment dispersion (Disperfin® WD 400, Rockwood pigments, Germany) were prepared using a Red Devil® mixing device. The Brookfield viscosity of each coating formulation was measured at 25 °C using a Brookfield DV3T device with spindle #2 at 200 rpm. The details of the formulations and the Brookfield viscosities are shown in Table 4.

Table 6

[0108] Test method for evaluating surfactant examples: Each surfactant example in the coating formulation was tested using the following test method.

[0109] Foaming evaluation: The foaming property of the surfactant example in the coating formulation was measured by mixing 0.2 wt% of the surfactant in each coating formulation for 5 minutes in a 4-ounce glass jar using a Red Devil (trademark) 5400 paint mixer. The initial height of the liquid before mixing and the final height of the liquid + foam immediately after mixing were marked on the glass jar. The foam height was determined as the difference between the final height and the initial height.

[0110] Wetting performance evaluation: The wetting performance was evaluated by applying each coating formulation onto a Shield Leneta (trademark) chart (WB form B# 5127) using a BYK-Gardner drawdown applicator. To better distinguish between samples, a new method of drawdown with a thin film of 25-micron wet film thickness (WFT) was developed for a 100-micron WFT generally used in the industry. This new approach allowed for better discrimination between surfactant samples and thus helped establish the structure-property relationship. The wetting performance was visually evaluated for pinholes, craters, and other coating defects. An evaluation scale of 1 - 5 was recorded for each drawdown. For example, an evaluation of 1 was recorded for the surfactant example with the lowest wetting, and an evaluation of 5 was recorded for the surfactant example with the best wetting.

[0111] Results of surfactant performance: Table 5 shows the foam heights of the example surfactants in coating formulations A, B, and C at 0.2 wt% surfactant solids, and Table 6 shows the application performance as a visual evaluation of substrate wetting.

Table 7

Table 8

Claims

1. (i) Reactant A: an aliphatic polyether polyol having a weight-average molecular weight of approximately 100 to approximately 4000, (ii) Reactant B: comprising a reaction product with an epoxy compound having at least one epoxy group per molecule, A surfactant having a molar equivalent ratio of "reactant A" to "reactant B" of approximately 1:0.5 to approximately 1:

4.

2. (i) Reactant B: An epoxy compound having at least one epoxy group per molecule, (ii) Reactant C: The surfactant according to claim 1, further comprising a reaction product with an aliphatic alkoxylated alcohol having a weight-average molecular weight of about 100 to about 4000.

3. The surfactant according to claim 1 or 2, wherein the aliphatic polyether polyol is a polyalkylene glycol.

4. The surfactant according to claim 1 or 2, wherein the aliphatic polyether polyol is polyethylene glycol (PEG).

5. The polyethylene glycol is PEG 100, PEG 200, PEG 300, PEG 400, PEG 500, PEG 600, PEG 700, PEG 800, PEG 900, PEG 1000, PEG 1100, PEG 1200, PEG 1300, PEG 1400, PEG 1500, PEG 1600, PEG 1700, PEG 1800, PEG 1900, PEG 2000, PEG 2100, PEG 2200, PEG 2300, PEG 2400, PEG 2500, PEG 2600, PEG 2700, PEG 2800, PEG 2900, PEG 3000, PEG 3100, PEG 3200, PEG 3300, PEG 3400, PEG 3500, PEG The surfactant according to claim 4, selected from the group consisting of PEG 3600, PEG 3700, PEG 3800, PEG 3900, and PEG 4000.

6. The surfactant according to claim 1 or 2, wherein the epoxy compound is an alkyl glycidyl ether or an allyl glycidyl ether.

7. The surfactant according to claim 6, wherein the alkyl glycidyl ether is selected from the group consisting of 2-ethylhexyl glycidyl ether (EHGE), n-butyl glycidyl ether, octyl glycidyl ether, 2-hexyldecyl glycidyl ether, 2-octyldodecyl glycidyl ether, 2-heptylundecyl glycidyl ether, 2-(1,3,3-trimethylbutyl)octyl glycidyl ether, 2-decyltetradecyl glycidyl ether, 2-dodecylhexadecyl glycidyl ether, and 2-tetradecyloctadecyl glycidyl ether.

8. The surfactant according to claim 6, wherein the alkyl glycidyl ether is 2-ethylhexyl glycidyl ether (EHGE).

9. The surfactant according to claim 1 or 2, wherein the reaction product of reactant A and reactant B comprises a mixture of a monofunctionalized polyol and at least one polyfunctionalized polyol.

10. The surfactant according to claim 9, wherein the reactant B is an alkyl glycidyl ether, and the reaction product of the reactant A and the reactant B includes a polyol monofunctionalized with an alkyl glycidyl ether and a polyol polyfunctionalized with an alkyl glycidyl ether.

11. The reaction product of reactant A and reactant B is (i) A polyol monofunctionalized with approximately 0.05% to approximately 40.0% alkylglycidyl ether, (ii) The surfactant according to claim 10, comprising a polyol polyfunctionalized with approximately 60.0% to approximately 99.95% alkyl glycidyl ether.

12. The surfactant according to claim 1 or 2, wherein the aliphatic polyether polyol is polyethylene glycol and the epoxy compound is 2-ethylhexyl glycidyl ether.

13. The surfactant according to claim 12, wherein the molar equivalent ratio of polyethylene glycol to 2-ethylhexylglycidyl ether is about 1:

2.

14. A method for producing a surfactant according to claim 1, A method comprising the step of (i) reacting about 1 molar equivalent of an aliphatic polyether polyol and (ii) about 2 molar equivalents of an epoxy compound in the presence of about 0.05 molar equivalents of a base to form a mixture of a monofunctionalized polyol with the epoxy compound and at least one polyol polyfunctionalized with the epoxy compound.

15. The method according to claim 14, wherein the epoxy compound has at least one epoxy group per molecule.

16. The method according to claim 14, wherein the epoxy compound is an alkylglycidyl ether or an allylglycidyl ether.

17. The method according to claim 14, wherein the reaction is carried out at a temperature of about 80°C to about 120°C.

18. The aforementioned base, (i) an amine selected from the group consisting of triethylamine, 4-(dimethylamino)pyridine, and 1,1,3,3-tetramethylguanidine; and (ii) Oxides, hydroxides, carbonates, and bicarbonates of sodium, potassium, and calcium, and combinations thereof The method according to claim 14, selected from the group consisting of the following.

19. The method according to claim 14, wherein the base is sodium hydroxide or potassium hydroxide.

20. (i) Polyethylene glycol (PEG) having a weight-average molecular weight of approximately 100 to approximately 4000, (ii) Reaction product with 2-ethylhexylglycidyl ether (EHGE), One molar equivalent of PEG reacts with two molar equivalents of EHGE to form a mixture of monofunctionalized PEG, difunctionalized PEG, trifunctionalized PEG, tetrafunctionalized PEG, and pentafunctionalized PEG. 【Chemistry 1】 It has a general structure represented by, Each C 11 H 22 O 2 The units are independent, 【Chemistry 2】 or 【Transformation 3】 And, Each C 11 H 22 O 2 The units are attached to the polyethylene glycol core or another C 11 H 22 O 2 unit by a carbon-oxygen single bond, n = 2 to 90, and a + b = 1 to 5. PEG monofunctionalized by EHGE, where a+b = 1, PEG, which is bifunctionalized by EHGE, where a+b = 2, PEG trifunctionalized by EHGE, where a+b = 3, PEG that has been quadrifunctionalized by EHGE, where a+b = 4, A surfactant comprising a reaction product containing pentafunctionalized PEG by EHGE, where a+b = 5.

21. The surfactant according to claim 2, wherein the aliphatic alkoxylated alcohol has the following structure. 【Chemistry 4】 (In the formula, R is a linear or branched alkyl group having 1 to 20 carbon atoms, R 1 = H and / or CH 3 (n=1 to 25)

22. The aliphatic alkoxylated alcohol has 3 to 23 ethoxylate units. 6-20 The surfactant according to claim 21, selected from the group consisting of alcohol ethoxylates.

23. (i) A surfactant according to claim 1 or 2 in an amount of approximately 5.0% to approximately 99.5% by weight, (ii) A composition comprising at least one additive in an amount of about 0.5% to about 95.0% by weight.

24. The composition according to claim 23, wherein the at least one additive is selected from the group consisting of flocculants, film-forming agents, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersants, defoamers, wet edge additives, wetting agents, humectants, waxes, colorants, thickeners, anti-solidification agents, anti-foaming agents, UV absorbers, pigments, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, insecticides, antioxidants, and plasticizers.

25. The composition according to claim 23, which is used in paper products, metal coatings, architectural coatings, graphic arts, textile materials, films, sheets, composite materials, printing inks, inkjet printing, flocks and other adhesives, hair care products, skin care products, nail care products, household products, livestock / agriculture, wood coatings, textile products, nonwoven coatings, and seed applications.

26. (i) A surfactant according to claim 1 or 2 in an amount of about 0.1% by weight to about 5.0% by weight, (ii) at least one film-forming polymer in an amount of approximately 5.0% to approximately 85.0% by weight, (iii) A coating composition comprising at least one additive in an amount of about 10.0% to about 94.9% by weight.

27. The coating composition according to claim 26, wherein the film-forming polymer is selected from the group consisting of acrylic, vinyl acrylic, styrene-acrylic copolymer, styrene-butadiene copolymer, vinyl acetate-ethylene copolymer, butadiene-acrylonitrile copolymer, polyepoxide, polyurethane, polyamide, urethane acrylic, vinyl ester of neodecanoic acid, and polyester.

28. The coating composition according to claim 26, wherein the at least one additive is selected from the group consisting of flocculants, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersants, defoamers, wet edge additives, wetting agents, humectants, waxes, colorants, thickeners, anti-solidification agents, anti-foaming agents, UV absorbers, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, insecticides, antioxidants, pigments, and plasticizers.

29. The coating composition according to claim 28, wherein the pigment is selected from the group consisting of phthalocyanine, iron oxide, titanium dioxide, zinc oxide, indigo, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silica, talc, calcium carbonate, and mixtures thereof.

30. The coating composition according to claim 26, which is used for lacquer coatings, primer coatings, inkjet printing, top coatings, varnish coatings, architectural coatings, wood coatings, printing inks, or metal or non-metal coatings.

31. The coating composition according to claim 26, coated on a substrate selected from the group consisting of porous and non-porous substrates, paper, nonwoven materials, textiles, leather, wood, concrete, stonework, metals, nonmetals, house wraps, building materials, fiberglass, polymer articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, airbags, fabrics, ceramics, yarns and blends, textile substrates, knitted substrates, natural substrates, synthetic substrates, and recycled substrates.

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