Surfactants comprising polyol / monoalcohol-epoxy products and methods of making same, compositions and methods of using same

Abstract

Disclosed herein is a surfactant comprising the reaction product of: (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of from about 100 to about 4000; and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the ratio of the molar equivalents of the "reactant A" to the molar equivalents of the "reactant B" is from about 1: 0.5 to about 1: 4. Also disclosed is a process for the preparation of surfactants and compositions comprising surfactants, in particular coating compositions.

Description

Technical Field

[0001] The present application relates to a surfactant comprising the 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 ratio of the molar equivalent of "reactant A" to the molar equivalent of "reactant B" is from about 1:0.5 to about 1:4. Background Art

[0002] Surfactants are commonly used in coating formulations to promote the wetting of the coating to the substrate and the wetting of the resin to the pigment. Surfactants can also increase the life of the coating by increasing shelf stability, and improve the flexibility (latitude) of the formulation by preventing the instability of the coating composition when different ingredients are added. Low levels of surfactants are usually used to achieve these goals, and surfactant combinations can be used to give one or more of the above-mentioned properties. Surfactants are usually non-volatile compounds in environmental settings; therefore, surfactants remain in the coating after drying. At the low amount commonly used, the effect on polymer hardness or coating performance is small. If there is an excessive amount of surfactant in the water-based coating composition, the wet coating may foam excessively, and the thickening effect of the thickener is poor, and the cured coating may have water sensitivity, poor external durability, and poor anti-adhesion, anti-fouling and anti-marking properties. Therefore, surfactants are usually used in as small a dose as possible to achieve their beneficial properties while avoiding any negative results.

[0003] In the application of coating formulations, the ability to reduce the surface tension of water is crucial, because the reduction in surface tension generally corresponds to improved substrate wettability. Coatings, inks, adhesives, fountain solutions, cleaning compositions and agricultural formulations are all examples of aqueous compositions. Surfactants are commonly used to reduce the surface tension in water-based systems, thereby improving surface coverage, reducing defects, and making dispersion more uniform. When the system is in a static state, it is crucial to balance the surface tension performance. The ability of surfactants to reduce surface tension and provide wetting under high-speed application conditions (i.e., high surface formation rate) is measured by dynamic surface tension.

[0004] US Patent 7550542B2 discloses a synthetic polymer having a water-soluble or water-swellable polymer backbone and end groups and / or intermediate groups of hydrophobe blocks of alkyl compounds or aromatic compounds containing polymerizable cyclic monomers or polymerizable double bond (or olefin) groups or derivatives thereof. The hydrophobe blocks are composed of two or more identical or different hydrophobe units. These synthetic polymers are used as rheology modifiers, particularly in latex paints.

[0005] US Patent 8388806 B2 describes a hydrophobically modified polyethylene glycol for use in pitch and sticky matter control in pulp and papermaking processes.

[0006] PCT Application 202006554A1 provides a composition comprising an oil, a surfactant and an optional charged polymer complex and a method of making the composition. The composition may also include an aqueous phase to provide a microemulsion. The technology also provides methods of using such compositions in home care and personal care.

[0007] JP Patent 05659340B2 describes a surfactant obtained by reacting 1 mol of a polyoxyalkylene compound containing a polyoxyalkylene compound with 1 to 8 mols of a 6-21 C alkyl glycidyl ether.

[0008] JP Publication No. 2003253197A describes an antifouling agent comprising a crosslinked polymer formed by ring-opening addition polymerization of an epoxy compound selected from monoalcohol glycidyl ether and polyalcohol glycidyl ether and a hydroxylated compound selected from monoalcohol, polyalcohol and polyoxyalkylene compound formed by substituting a monoalcohol or polyalcohol with a polyoxyalkylene group.

[0009] JP Publication No. 2011088113A describes an emulsifier comprising a compound obtained by reacting (a) a glycidyl ether with (b) a water-soluble polyolefin alcohol having hydroxyl groups at both ends of the molecular chain to form an adduct, and then reacting the adduct with (c) an organic diisocyanate.

[0010] US publication 20080188673A1 describes low surface tension surfactants based on ether alcohols and provides their use as surfactants in aqueous coating formulations, the surfactants being prepared by reacting at least one hydroxy compound.

[0011] CN publication 112939898A describes a series of epoxy compounds, one end of which is an epoxy group that reacts with polyester, alkyd resin or acrylic resin; the other end is an ether chain part, which is suitable for casting materials, fiberglass winding, mold making, coatings, and medical applications.

[0012] There is a need for surfactants with high surface activity in pigment dispersibility, wetting, and surfactant compositions effective in lacquer coatings, primer coatings, inkjet printing, topcoats, clearcoats, and metallic or non-metallic coatings.

[0013] The present invention relates to an improved surfactant comprising the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents 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 the coating formulation of the present invention.

[0014] It is therefore an object of the present invention to provide a surfactant that provides well balanced surface tension and dynamic surface tension as well as low foaming properties which will be widely accepted in the coatings, inks, adhesives and agricultural formulations industries.

[0015] The surfactants added to the compositions of the present invention act as wetting agents and dispersants to improve the coating properties so that it has reduced film defects such as fish eyes and pits.

[0016] The present invention includes a surfactant and a composition thereof for use in a coating composition, which comprises the 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 ratio of the molar equivalent of "reactant A" to the molar equivalent of "reactant B" is from about 1:0.5 to about 1:4. Summary of the invention

[0017] The main aspect of the present application is to provide a surfactant and a composition thereof, which comprises the 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 of "reactant A" to the number of epoxy groups in "reactant B" is about 1:0.5 to about 1:4.

[0018] In another aspect, the present application provides a surfactant, which further comprises the 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.

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

[0020] In another aspect, the present application provides a method for preparing a surfactant, comprising: 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 equivalents of a base to form a mixture of a polyol monofunctionalized with an epoxy compound and at least one polyol multifunctionalized with an epoxy compound. In another aspect, the present application provides a surfactant, comprising the following reaction products: (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, the general structure of which is:

[0021]

[0022] Among them, each C 11 H 22 The O2 unit is independently

[0023]

[0024] Among them, each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit;

[0025] Where n=2 to 90, and a+b=1 to 5, which includes:

[0026] a+b=1, PEG monofunctionalized by EHGE;

[0027] a+b=2, PEG difunctionalized by EHGE;

[0028] a+b=3, PEG trifunctionalized by EHGE;

[0029] a+b=4, PEG tetrafunctionalized by EHGE; and

[0030] a+b=5, PEG pentafunctionalized by EHGE.

[0031] In another aspect, the present application provides a surfactant comprising the reaction product of: (i) an aliphatic alkoxylated alcohol R-(OCH2CHR1) n-OH; and (ii) 2-ethylhexyl glycidyl ether (EHGE); wherein 1 molar equivalent of an aliphatic alkoxylated alcohol is reacted 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, the general structure of which is:

[0032]

[0033] Among them, each C 11 H 22 The O2 unit is independently

[0034]

[0035] Among them, each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit;

[0036] Wherein, R = a straight chain alkyl or branched chain alkyl having 1 to 20 carbons; R1 = H and / or CH3, and n = 1 to 25;

[0037] Wherein, a=1 to 5, which includes:

[0038] a=1, aliphatic alkoxylated alcohol monofunctionalized by EHGE;

[0039] a = 2, aliphatic alkoxylated alcohol difunctionalized by EHGE;

[0040] a=3, aliphatic alkoxylated alcohol trifunctionalized by EHGE;

[0041] a=4, aliphatic alkoxylated alcohol tetrafunctionalized by EHGE; and

[0042] a=5, aliphatic alkoxylated alcohol pentafunctionalized by EHGE.

[0043] In another aspect, the present application provides a composition comprising (i) about 5.0 wt % to about 99.5 wt % of a surfactant, which comprises the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4; and (iii) about 0.5 wt % to about 95.0 wt % of at least one additive.

[0044] In another aspect, the present application provides a composition comprising (i) from about 5.0 wt % to about 99.5 wt % of a surfactant comprising:

[0045] (a) the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4, and wherein the surfactant further comprises the 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

[0046] (b) from about 0.5% to about 95.0% by weight of at least one additive.

[0047] In another aspect, the present application provides a coating composition comprising: (i) about 0.1 wt % to about 5.0 wt % of a surfactant, which comprises the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4; and (iii) about 5.0 wt % to about 85.0 wt % of at least one film-forming polymer; and (iv) about 10.0 wt % to about 94.9 wt % of at least one additive.

[0048] In another aspect, the present application provides a coating composition comprising:

[0049] (I) from about 0.1% to about 5.0% by weight of a surfactant comprising: (a) the reaction product of: (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of from about 100 to about 4000, and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4, and (b) the 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 from about 100 to about 4000;

[0050] (II) from about 5.0% to about 85.0% by weight of at least one film-forming polymer; and

[0051] (III) from about 10.0% to about 94.9% by weight of at least one additive. DETAILED DESCRIPTION

[0052] Before explaining in detail at least one aspect of the disclosed and / or claimed inventive concept, it should be understood that the disclosed and / or claimed inventive concept is not limited in its application to the construction details and arrangements of components or steps or methods set forth in the following description or shown in the accompanying drawings. The disclosed and / or claimed inventive concept can be used in other aspects or practiced or implemented in a variety of ways. In addition, it should be understood that the words and terms used herein are for descriptive purposes only and should not be considered limiting.

[0053] Unless otherwise defined herein, the technical terms used in connection with the disclosed and / or claimed inventive concepts shall have the meanings commonly understood by those of ordinary skill in the art. In addition, unless the context otherwise requires, singular terms shall include plural terms and plural terms shall include the singular.

[0054] The singular indefinite articles ("a", "an") and definite articles ("the") include the plural forms unless the context clearly dictates otherwise or clearly implies to the contrary. The terms "comprising / comprised of" include the more restrictive meanings "consisting essentially of" and "consisting of".

[0055] For purposes of the following detailed description, except in any operating examples or where otherwise indicated, the numbers expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in the specification and attached claims are approximations that may vary depending upon the desired properties to be obtained in practicing the present invention.

[0056] All percentages, parts, ratios and proportions used herein are by weight of the total composition, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.

[0057] All publications, articles, treatises, patents, patent publications, and other references cited herein are incorporated herein in their entirety for all purposes to the extent consistent with the disclosure herein.

[0058] As used in this disclosure, unless otherwise indicated, the following terms shall be understood to have the following meanings.

[0059] The term "at least one" will be understood to include any number of one and 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 be extended to 100 or 1000 or more, depending on the term attached to it. In addition, the amount of 100 / 1000 should not be considered as limiting the lower limit or upper limit.

[0060] As used herein, the words "comprising" (and any form thereof, such as the infinitive (comprise) and the third person singular (comprises)), "having" (and any form thereof, such as the infinitive (have) and the third person singular (has)), "including" (and any form thereof, such as the third person singular (includes) and the infinitive (include)), or "containing" (and any form thereof, such as the third person singular (contains) and the infinitive (contain)) are inclusive or open-ended, and do not exclude additional, unrecited elements or method steps.

[0061] As used herein, the term "surfactant" refers to any amphiphilic molecule that reduces surface tension when added to water.

[0062] As used herein, the term "moiety" or "moieties" refers to a portion or functional group of a molecule.

[0063] The term "substituted" means that the specified group or moiety has one or more substituents.

[0064] The term "functionalized" with respect to any moiety refers to the presence of one or more functional groups in the moiety. Multiple functional groups can be introduced into the moiety by one or more functionalization reactions known to those of ordinary skill in the art. It is understood that an alcohol or polyol "functionalized" with an epoxide or glycidyl ether has reacted so that at least one hydroxyl group of the alcohol or polyol has formed an ether bond to a carbon atom of the epoxide group of the epoxide or glycidyl ether, and so that at least one epoxide group of the epoxide or glycidyl ether is ring-opened after attack by the alcohol or polyol to generate new hydroxyl groups.

[0065] As used herein, the term "aliphatic polyether polyol" refers to reactant A, 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.

[0066] 00, 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, PEG 4000, PEG 4100, PEG 4200, PEG 4300, PEG 4400, PEG 4500, PEG 4600, PEG 4700, PEG 4800, PEG 4900, PEG 500 3400, PEG 3500, PEG3600, PEG 3700, PEG 3800, PEG 3900 and PEG 4000.

[0067] In one non-limiting embodiment, the epoxy compound used as reactant B in the claimed invention is an alkyl glycidyl ether, wherein the alkyl group is a saturated or unsaturated linear or branched aliphatic hydrocarbon group having 3 to 24 carbon atoms. According to another non-limiting embodiment of the present application, the epoxy compound can be a primary linear alkyl glycidyl ether, such as 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-octadecyl glycidyl ether, n-octadecenyl glycidyl ether (oleyl glycidyl ether), behenyl glycidyl ether, etc.; a primary branched alkyl glycidyl ether, such as 2-ethylhexyl glycidyl ether, 2-hexyldecyl glycidyl ether, etc. glycidyl ether, such as tertiary alkyl glycidyl ether, ...

[0068] As used herein, the term "aliphatic alkoxylated alcohol" refers to a material having the following structure, reactant C:

[0069]

[0070] wherein R is a straight or branched alkyl group having 1 to 20 carbons; R1=H and / or CH3 and n=1 to 25.

[0071] In a non-limiting embodiment, the "aliphatic alkoxylated alcohol" includes a 6-20 Alcohol ethoxylates (3-23EO). Examples of such surfactants are available from BASF and Sasol Performance Chemicals

[0072]

[0073] In another non-limiting embodiment, the present application discloses a method for preparing a surfactant, comprising: reacting (i) about 1 molar equivalent of an aliphatic polyether polyol and (ii) about 2 molar equivalents of an alkyl glycidyl ether in the presence of about 0.05 molar equivalents of a base to form a mixture of a polyol monofunctionalized with an alkyl glycidyl ether and at least one polyol multifunctionalized with an alkyl glycidyl ether, wherein the reaction is carried out at a temperature of about 80° C. to about 120° C. in the presence of a base selected from (i) amines, including but not limited to 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.

[0074] In another non-limiting embodiment, the present application discloses the reaction of (i) polyethylene glycol and (ii) 2-ethylhexyl glycidyl ether, wherein the ratio of molar equivalents of polyethylene glycol to molar equivalents of 2-ethylhexyl glycidyl ether is from about 1:0.5 to about 1:4.

[0075] In another non-limiting embodiment, the present application discloses a method for preparing a surfactant, comprising: 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 an epoxy compound and at least one polyol multifunctionalized with an epoxy compound in the presence of about 0.05 molar equivalent of a base, wherein the reaction is carried out at a temperature of about 80° C. to about 120° C. in the presence of a base selected from (i) amines, including but not limited to 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.

[0076] In another non-limiting embodiment, the present application discloses that the ratio of the molar equivalents of polyethylene glycol to the molar equivalents of 2-ethylhexyl glycidyl ether is from about 1:0.5 to about 1:4.

[0077] In another embodiment, the present application discloses a surfactant comprising a polyol monofunctionalized with an alkyl glycidyl ether in an amount of about 0.05% to about 0.5%, or about 0.5% to about 1% by weight, or about 1% to about 2.5% by weight, or about 2.5% to about 5% by weight, or about 5% to about 10% by weight, or 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 wt % to about 35 wt %, or about 35 wt % to about 40 wt %; and a polyol multifunctionalized with an alkyl glycidyl ether 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 %.

[0078] In one embodiment, the present application discloses a surfactant comprising the 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 with EHGE, PEG difunctionalized with EHGE, PEG trifunctionalized with EHGE, PEG tetrafunctionalized with EHGE, and PEG pentafunctionalized with EHGE, the general structure of which is:

[0079]

[0080] Among them, each C 11 H 22 The O2 unit is independently

[0081]

[0082] Among them, each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit; wherein n=2 to 90 and a+b=1 to 5, including: a+b=1, PEG monofunctionalized by EHGE; a+b=2, PEG difunctionalized by EHGE; a+b=3, PEG trifunctionalized by EHGE; a+b=4, PEG tetrafunctionalized by EHGE; and a+b=5, PEG pentafunctionalized by EHGE.

[0083] In another embodiment, the present application provides a surfactant comprising the reaction product of: (i) an aliphatic alkoxylated alcohol R-(OCH2CHR1) n -OH; and (ii) 2-ethylhexyl glycidyl ether (EHGE); wherein 1 molar equivalent of an aliphatic alkoxylated alcohol is reacted 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, the general structure of which is:

[0084]

[0085] Among them, each C 11 H 22 The O2 unit is independently

[0086]

[0087] Among them, each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit;

[0088] wherein R is a linear or branched alkyl group having 1 to 20 carbon atoms, R1 = H and / or CH3 and n = 1 to 25;

[0089] Wherein, a=1 to 5, which includes:

[0090] a=1, aliphatic alkoxylated alcohol monofunctionalized by EHGE;

[0091] a = 2, aliphatic alkoxylated alcohol difunctionalized by EHGE;

[0092] a=3, aliphatic alkoxylated alcohol trifunctionalized by EHGE;

[0093] a=4, aliphatic alkoxylated alcohol tetrafunctionalized by EHGE; and

[0094] a=5, aliphatic alkoxylated alcohol pentafunctionalized by EHGE.

[0095] In one embodiment, the present application provides a composition comprising (i) about 5.0 wt % to about 99.5 wt % of a surfactant, which comprises the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4; and (iii) about 0.5 wt % to about 95.0 wt % of at least one additive.

[0096] In one embodiment, the present application provides a composition comprising (i) from about 5.0 wt % to about 99.5 wt % of a surfactant comprising:

[0097] (a) the 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 ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4; and wherein the surfactant further comprises the 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

[0098] (b) from about 0.5% to about 95.0% by weight of at least one additive.

[0099] In another embodiment, the present application discloses a coating composition comprising: (i) about 0.1 wt % to about 5.0 wt % of a surfactant comprising the reaction product of: (a) reactant A: an aliphatic polyether polyol having a weight average molecular weight of about 100 to about 4000, and (b) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4; and (ii) about 5.0 wt % to about 85.0 wt % of at least one film-forming polymer; and (iii) about 10.0 wt % to about 94.9 wt % of at least one additive.

[0100] In one embodiment, the present application discloses a coating composition comprising:

[0101] (I) from about 0.1% to about 5.0% by weight of a surfactant comprising: (a) the reaction product of: (i) reactant A: an aliphatic polyether polyol having a weight average molecular weight of from about 100 to about 4000, and (ii) reactant B: an epoxy compound having at least one epoxy group per molecule, wherein the ratio of the molar equivalents of "reactant A" to the molar equivalents of "reactant B" is from about 1:0.5 to about 1:4, and (b) the 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 from about 100 to about 4000;

[0102] (II) from about 5.0% to about 85.0% by weight of at least one film-forming polymer; and

[0103] (III) from about 10.0% to about 94.9% by weight of at least one additive.

[0104] According to another embodiment of the present application, the composition comprising the surfactant of the claimed invention is used in a variety of coating applications including, but not limited to, paper products, metal coatings, architectural coatings, graphic arts, fiber materials, films, sheets, composite materials, printing inks, inkjet printing, flock and other adhesives, hair care products, skin care products, nail care products, household products, animal husbandry / agriculture, wood coatings, textile products, nonwoven coatings, and seed applications.

[0105] In one embodiment, the present application discloses a composition comprising at least one additive, wherein the at least one additive is selected from the group consisting of: coalescing agents, film formers, emulsifiers, stabilizers, rheology modifiers, cosolvents, dispersants, defoamers, wet edge additives, wetting agents, humectants, waxes, colorants, thickeners, anticaking agents, antifoaming agents, UV absorbers, pigments, antifreeze agents, gel inhibitors, preservatives, hydrophobic agents, adhesion promoters, biocides, antioxidants and plasticizers.

[0106] In another embodiment, the present application discloses that the molecular weight of the fatty alkoxylated alcohol ranges from about 100 Daltons to about 4000 Daltons. In some embodiments, the molecular weight of the fatty alkoxylated alcohol ranges from about 100 Daltons to about 200 Daltons, or about 200 Daltons to about 300 Daltons, or about 300 Daltons to about 400 Daltons, or about 400 Daltons to about 500 Daltons, or about 500 Daltons to about 600 Daltons, or about 600 Daltons to about 700 Daltons, or about 700 Daltons to about 800 Daltons, or about 800 to about 900 Daltons, or about 900 Daltons to about 1000 Daltons, or about 1000 Daltons to about 1500 Daltons, or about 1500 Daltons to about 2000 Daltons, or about 2000 Daltons to about 2500 Daltons, or about 2500 Daltons to about 3000 Daltons, or about 3000 Daltons to about 3500 Daltons, or about 3500 Daltons to about 4000 Daltons.

[0107] In another embodiment, the present application discloses a composition comprising 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 %.

[0108] In another embodiment, the present application discloses that in a composition comprising one or more additives, the amount of the additive is from about 0.5 wt % to about 1 wt %, or from about 1 wt % to about 2.5 wt %, or from about 2.5 wt % to about 5 wt %, or from about 5 wt % to about 10 wt %, or from about 10 wt % to about 15 wt %, or from about 15 wt % to about 20 wt %, or from about 20 wt % to about 25 wt %, or from about 25 wt % to about 30 wt %, or from about 30 wt % to about 35 wt %, based on the total weight of the composition. %, 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 %.

[0109] In another embodiment, the present application discloses a coating composition comprising a surfactant, wherein the amount of the surfactant is from about 0.1 wt % to about 0.2 wt %, or from about 0.2 wt % to about 0.3 wt %, or from about 0.3 wt % to about 0.4 wt %, or from about 0.4 wt % to about 0.5 wt %, from about 0.5 wt % to about 0.6 wt %, from about 0.6 wt % to about 0.7 wt %, from about 0.7 wt % to about 0.8 wt %, from about 0.8 wt % to about 0.9 wt %, from about 0.9 wt % to about 1.0 wt %, from about 1.0 wt % to about 2 wt %, or from about 2.0 wt % to about 3.0 wt %, from about 3.0 wt % to about 4.0 wt %, or from about 4.0 wt % to about 5.0 wt %.

[0110] In another non-limiting embodiment, the present application discloses a coating composition comprising 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.

[0111] In another embodiment, the present application discloses a coating composition comprising one or more additives, wherein the amount of the one or more additives is from about 10 wt % to about 15 wt %, or from about 15 wt % to about 20 wt %, or from about 20 wt % to about 25 wt %, or from about 25 wt % to about 30 wt %, or from about 30 wt % to about 35 wt %, or from about 35 wt % to about 40 wt %, or from about 40 wt % to about 45 wt %, or from about 45 wt % to about 50 wt %, or from about 50 wt % to about 55 wt %, or from about 55 wt % to about 60 wt %, or from about 60 wt % to about 65 wt %, or from about 65 wt % to about 70 wt %, or from about 70 wt % to about 75 wt %, or from about 75 wt % to about 80 wt %, or from about 80 wt % to about 85 wt %, or from about 85 wt % to about 90 wt %, or from about 90 wt % to about 94.9 wt %.

[0112] In another embodiment of the present application, the coating composition including the coalescing agent may include, but is not limited to, ester alcohols, benzoate ethers, glycol ethers, glycol ether esters, and N-methyl-2-pyrrolidone.

[0113] In another embodiment of the present application, the composition comprising an emulsifier is selected from anionic emulsifiers such as monoethanolamine oleate, diethanolamine oleate or triethanolamine oleate, stearate, diethylethanolamine oleate, stearate, 2-amino-2-methyl-1-propanol stearate (2-amino 2-methylpropan-1-ol stearate), sulfonated compounds (e.g. sodium lauryl sulfate, Turkey red oil, etc.) and sulfonated compounds (e.g. sodium hexadecyl sulfonate); cationic emulsifiers, such as quaternary ammonium compounds (e.g. hexadecyltrimethylammonium bromide, dodecyldimethylbenzylammonium chloride, etc.); amphoteric emulsifiers (e.g. lecithin); and nonionic emulsifiers, such as fatty alcohols (dodecyl alcohol, hexadecyl alcohol, stearyl alcohol or palmityl alcohol), partial fatty acid esters of polyhydroxy alcohols with saturated fatty acids (glyceryl monostearate, pentaerythritol monostearate, ethylene glycol monostearate, propylene glycol monostearate), partial fatty acid esters of polyhydroxy alcohols with unsaturated fatty acids (e.g. glyceryl monooleate, pentaerythritol monooleate), polyoxyethylene esters of fatty acids (e.g. polyoxyethylene stearate), polymerization products of ethylene oxide and propylene oxide with fatty alcohols (fatty alcohol polyglycol ethers), or polymerization products of ethylene oxide and propylene oxide with fatty acids (fatty acid ethoxylates).

[0114] In one embodiment, the present application discloses a composition comprising a suitable rheology modifier to control viscosity over a wide range of shear rates. In addition, the coating composition comprises a rheology modifier, such as finely divided silica, layered silicate or polymerized cellulose, and a nonionic synthetic associative thickener (NSAT) compound.

[0115] 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, etc. In addition, suitable dispersants for use in the present composition are anionic polymers, such as homopolymers and copolymers based on polycarboxylic acids, including those that are hydrophobically modified, for example, polyacrylic acid or polymethacrylic acid or maleic anhydride with monomers such as styrene, acrylates or methacrylates, isobutylene and other hydrophilic comonomers or hydrophobic comonomers, as well as salts of the above dispersants and mixtures thereof.

[0116] In order to prevent the evaporation of water from the composition before the coating is completely dry, a suitable humectant may be added. Examples of such humectants are ethylene glycol, ethylene glycol dimethyl ether and polyethylene glycol.

[0117] Suitable defoaming agents in the composition may include silicone-based defoaming agents, mineral oil-based defoaming agents, and the like.

[0118] In another embodiment of the present application, the composition containing the antifoaming agent may include but is not limited to animal oil type antifoaming agents and vegetable oil type antifoaming agents, fatty acid type antifoaming agents, nonionic antifoaming agents (polyether antifoaming agents), acetylene glycol antifoaming agents, fluorine antifoaming agents, silicone antifoaming agents, mineral oil antifoaming agents, and phosphate antifoaming agents.

[0119] In another embodiment of the present application, a thickener is added to the composition to achieve the desired viscosity and flow properties. The thickener may include, but is not limited to, cellulose derivatives, including hydroxyethyl cellulose, methyl cellulose, and carboxymethyl cellulose, and the thickener may be used in the composition.

[0120] Suitable thickeners may include, but are not limited to, polyvinyl alcohol (PVA), hydrophobically modified alkali-soluble emulsions (referred to in the art as HASE emulsions), alkali-soluble or alkali-swellable emulsions (referred to in the art as ASE emulsions), hydrophobically modified ethylene oxide-urethane polymers (referred to in the art as HEUR thickeners), and cellulosic thickeners such as hydroxymethyl cellulose (HMC), hydroxyethyl cellulose (HEC), hydrophobically modified 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 used as thickeners are fumed silica, attapulgite clay and other types of clays, titanate chelating agents, and the like.

[0121] "Antifreeze" refers to an additive that prevents freezing. Suitable antifreeze agents may include, but are not limited to, alcohols, polyols such as glycerol, glycols such as propylene glycol, and polyol fatty acid esters or derivatives thereof.

[0122] One or more low-dose preservatives may be added to the composition to prevent the growth of microorganisms. Preservatives may include, but are not limited to, 2-methyl-4-isothiazoline-3-one (MIT), 1,2-benzisothiazolin-3-one (BIT), 5-chloro-2-methyl-4-isothiazoline-3-one (CMIT), 2-octyl-4-isothiazoline-3-one (Off), 3-iodo-2-propynylbutylcarbamate (IPBC), oxyfluorfen, thiabendazole, terbutryn, zinc pyrithione (ZnPy), and suitable mildew inhibitors and biocides in the composition include zinc oxide, isothiazolone, and triazole.

[0123] In another embodiment of the present application, suitable latex adhesion promoters in the composition include, but are not limited to, homopolymers, copolymers or terpolymers, such as, for example, polymers or copolymers of acrylic acid or methacrylic acid, polyvinyl acetate, styrene-acrylic acid copolymers, styrene-butadiene copolymers, vinyl acetate-acrylic acid copolymers, ethylene-vinyl acetate copolymers, vinyl acetate-versatate vinyl ester copolymers, vinyl acetate-maleic acid vinyl ester copolymers, vinyl acetate-vinyl chloride-acrylic acid terpolymers, ethylene-vinyl acetate-acrylic acid terpolymers and urethane polymers. The polymer may contain up to about 10% by weight of monomers containing functional groups (such as, but not limited to, carboxylic acid groups, phosphate groups, sulfate groups, sulfonate groups and amide groups), other monomers and mixtures thereof.

[0124] The composition of the present disclosure may also include at least one pigment. The pigment may be selected from phthalocyanine, iron oxide, titanium dioxide, zinc oxide, indigo, hydrated aluminum oxide, barium sulfate, calcium silicate, clay, silicon dioxide, talc, calcium carbonate and mixtures thereof. The titanium dioxide grade used in the composition is surface modified with a variety of inorganic oxides such as silicates, aluminates and zirconates. Aluminum silicate, nepheline syenite, mica, calcium carbonate and / or diatomaceous earth may also be used.

[0125] The composition of the present disclosure may also include at least one film-forming polymer. The film-forming polymer of the present disclosure may be selected from a variety of polymers known in the relevant art. For example, these film-forming polymers may be derived from a variety of olefin-unsaturated monomers, such as ethylene monomers, vinyl monomers, and acrylic monomers. Examples of such monomers may include, but are not limited to, acrylic acid, methacrylic acid, methacrylate, styrene, α-methylstyrene, vinyl chloride, acrylonitrile, methacrylonitrile, urea-methacrylate, vinyl acetate, vinyl esters of branched tertiary monocarboxylic acids, itaconic acid, crotonic acid, maleic acid, fumaric acid, and ethylene. C4-C8 conjugated dienes may also be included, such as 1,3-butadiene, isoprene, and chloroprene. The film-forming polymer may also be a copolymerization product of more than one monomer to achieve several desired properties, particularly in latex paints containing little or no volatile organic compounds (VOC). Examples of suitable film-forming polymers may 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 ester of neodecanoic acid, vinyl propionate, butadiene, acrylonitrile, maleate, and fumarate. In a non-limiting embodiment of the present disclosure, the film-forming polymer is selected from acrylic acid, vinyl-acrylic acid and styrene-acrylic acid, styrene-butadiene copolymers, vinyl acetate ethylene, butadiene-acrylonitrile copolymers, polyepoxides, polyurethanes, polyamides, vinyl ester of neodecanoic acid, and polyesters.

[0126] Examples of other suitable film-forming polymers may include, but are not limited to, alkyds, cellulose (cellulose nitrate and cellulose esters), coumarone-indene, epoxies, esters, hydrocarbons, melamines, natural resins, oleoresins, phenolics, polyamides, polyesters, rosins, siloxanes, terpenes, ureas, and urethanes.

[0127] Additives may be included in small amounts, i.e., less than about 10% by weight based on the total weight of the composition. Such additives include co-solvents, wet edge additives, wetting agents, waxes, colorants, anticaking agents, UV absorbers, gel inhibitors, hydrophobic agents, and antioxidants.

[0128] In one embodiment, the present application discloses a coating composition for use in paint coatings, primer coatings, inkjet printing, top coatings, clear coatings, architectural coatings, wood coatings, printing inks, and metallic or non-metallic coatings.

[0129] The coating composition in the form of a paint may include enamel, lacquer, varnish, undercoat, primer, sealant, filler, stopper, and the like.

[0130] In one embodiment, the present application discloses a coating composition applied to a substrate selected from porous substrates and non-porous substrates, paper, nonwoven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wraps, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, furniture upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and blended substrates, woven substrates, non-woven substrates, knitted substrates, natural substrates, synthetic substrates, and recycled substrates.

[0131] In addition, some aspects of the present application are described in detail by the following examples. The examples given herein are for illustrating the present application, but are not intended to limit the present application.

[0132] Example

[0133] Synthesis scheme reaction of PEG and EHGE

[0134]

[0135] Each C 11 H 22 The O2 unit is independently

[0136]

[0137] And each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit, and wherein a+b=1 to 5, n=2 to 90;

[0138] For monosubstituted surfactant adducts, a+b=1.

[0139] For disubstituted surfactant adducts, a+b=2.

[0140] For tri-substituted surfactant adducts, a+b=3.

[0141] For tetra-substituted surfactant adducts, a+b=4.

[0142] For pentasubstituted surfactant adducts, a+b=5.

[0143] Experimental step 1 (batch step) : The reaction of PEG and EHGE was performed using the following one-pot procedure: polyethylene glycol, 2-ethylhexyl glycidyl ether, and potassium hydroxide were mixed in a container, which was sealed and maintained under a nitrogen atmosphere. The reaction mixture was stirred and heated to 100°C for 7 to 19 hours and then cooled to room temperature. This procedure was used for the following examples.

[0144] Example 1: According to experimental procedure 1, PEG 400 (28.50 g), 2-ethylhexyl glycidyl ether (6.64 g) and potassium hydroxide (200 mg) were reacted at 100°C for 19 hours.

[0145] Example 2: According to the experimental procedure 1, PEG 400 (11.00 g), 2-ethylhexyl glycidyl ether (20.49 g) and potassium hydroxide (77 mg) were reacted at 100°C for 19 hours.

[0146] Example 4: According to the experimental procedure 1, PEG 300 (111.51 g), 2-ethylhexyl glycidyl ether (138.49 g) and potassium hydroxide (1.043 g) were reacted at 100°C for 7 hours.

[0147] Experimental procedure 2 (slow addition step) : The reaction of PEG and EHGE was carried out using the following slow addition procedure: Polyethylene glycol and potassium hydroxide were mixed in a container, which was sealed and maintained under a nitrogen atmosphere. The reaction mixture was stirred and heated to 100°C. When the temperature reached 100°C, 2-ethylhexyl glycidyl ether was slowly added over about 1 hour. The reaction mixture was stirred at 100°C for 30 minutes, then at 120°C for 3 to 3.5 hours, and then cooled to room temperature. This procedure was used for the following examples.

[0148] Example 3: According to experimental procedure 2, PEG 200 (87.00 g), 2-ethylhexyl glycidyl ether (162.07 g) and potassium hydroxide (1.22 g) were reacted.

[0149] Example 5: According to experimental procedure 2, PEG 400 (520.00 g), 2-ethylhexyl glycidyl ether (484.35 g) and potassium hydroxide (3.65 g) were reacted.

[0150] Example 6: According to experimental procedure 2, PEG 600 (160.00 g), 2-ethylhexyl glycidyl ether (99.35 g) and potassium hydroxide (748 mg) were reacted.

[0151] Example 7: According to experimental procedure 2, PEG 1000 (190.00 g), 2-ethylhexyl glycidyl ether (70.79 g) and potassium hydroxide (533 mg) were reacted.

[0152] Example 8: According to experimental procedure 2, PEG 2000 (210.50 g), 2-ethylhexyl glycidyl ether (39.21 g) and potassium hydroxide (398 mg) were reacted.

[0153] Example 9: According to experimental procedure 2, PEG 4000 (228.50 g), 2-ethylhexyl glycidyl ether (21.28 g) and potassium hydroxide (396 mg) were reacted.

[0154] LCMS: LCMS was used to separate mixtures of substituted PEGs and determine the relative abundance of PEGs with varying degrees of substitution. Peaks corresponding to unsubstituted PEG, monosubstituted PEG, disubstituted PEG, trisubstituted PEG, and tetrasubstituted PEG were well resolved by HPLC and could be reliably integrated.

[0155] Procedure: About 0.1 g of each sample was mixed 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 6520QTOF LC / MS using an Agilent 1260 HPLC and MassHunter software.

[0156] HPLC conditions:

[0157]

[0158] MS conditions:

[0159]

[0160] Table 1 lists the product distributions determined for the reaction products of Examples 1-7.

[0161] Table 1: Product distribution of substituted PEGs determined by LCMS, area %

[0162]

[0163] Contact angle, static surface tension, dynamic surface tension and foaming measurements of surfactants:

[0164] Solution preparation: Aqueous solutions of surfactants were prepared by mixing 1 g of adduct and 1000 g of DI water (filtered through Millipore-Q, pH 6.3 to 6.7) at room temperature. The resulting solution was mixed for 24 hours using a magnetic stirrer before further measurements. The solution pH of the selected samples was about 7.4.

[0165] Contact Angle Measurements: A clear, self-adhesive, 0.002 inch thick polypropylene film (McMaster-Carr #5577149-01) was used as a substrate to measure the contact angle of a 0.1 wt % aqueous solution of surfactant.

[0166] Kruss's Drop Shape Analysis System DSA 305 was used to determine the contact angle value between the sample droplet and the polypropylene surface. A disposable 1 mL syringe was used to automatically dispense the sample drops. The contact angle of each droplet was automatically determined by the instrument fitting model software (Kruss AdvanceDrop Shape V 1.5.1) and recorded once per second within 30 seconds. Multiple droplets were placed on the pre-cleaned polypropylene surface at a sufficient distance, and the results were reported as average values. At least 6 droplets were analyzed for each sample. All measurements were performed at ambient temperature and relative humidity.

[0167] Static surface tension measurements: Static surface tension values ​​of freshly mixed 0.1 wt% aqueous solutions of surfactants were measured at room temperature using a tensiometer (Attension, BiolinScientific) according to the Wilhelmy Plate method based on the instrument company's recommendations (in accordance with ASTM D1331-20). For each sample, three surface tension measurements were recorded and the average was reported. Prior to each measurement, the Wilhelmy plate was rinsed and pyrolyzed with a flame. At the beginning of the measurement, the calibration of the equipment was checked by measuring the surface tension of DI water.

[0168] Dynamic surface tension measurements: The dynamic surface tension of freshly mixed 0.1 wt % aqueous solutions of surfactants with surface age ranging from 10 ms to 100,000 ms was measured using a bubble pressure tensiometer (Kruss, Model BP2) using a 0.256 mm diameter hydrophobic coated glass capillary. The capillary was cleaned with a detergent solution between sampling and rinsed with DI water and then wiped dry with a Kimwipe. Prior to experimental measurements, the calibration of the equipment was checked by measuring the surface tension of DI water.

[0169] Foaming index determination: The foaming behavior of surfactants was evaluated using the SITAMesstechnik foam tester R-2000. About 900 mL of freshly mixed 0.1 wt % solution was filled into the instrument reservoir, and the test parameters were entered using the instrument software. Each sample was tested 3 times at room temperature. In order to form foam, 250 mL of solution was filled in 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 above the liquid was measured with the conductive probe of the instrument, and the foam volume (mL) was recorded with the instrument software. This step was repeated 30 times, and the foam accumulated by 30 continuous mixing steps was recorded. For each sample, after completing three experiments, the average foam volume of each mixing step was calculated. The foaming index is defined as the total foam volume at the end of 30 mixing steps, and the average value of the foam volume of each mixing step is added and calculated using Excel software (Table 2).

[0170] Table 2: Contact angle, static surface tension, dynamic surface tension and foaming measurements

[0171]

[0172] *PP = Polypropylene

[0173] Coating formulations were prepared using the binder resins shown in Table 3. Binder #3 was prepared by diluting Neocryl XK-98 with DI water to achieve a 33% solids level.

[0174] Table 3: Binder resins used in coating formulations

[0175]

[0176] Neopac TM E-180 is a solvent-free aromatic acrylic urethane dispersion recommended for floor coatings from DSM Coating Resins.

[0177] Neocryl TM XK-98 is a self-crosslinking acrylic copolymer emulsion provided by DSM Coating Resins

[0178] Using Red Devil TM Mixing equipment to prepare a dispersion of binder resin, co-solvent butyl carbitol (BC) and transparent red iron oxide pigment (Rockwood pigments) The coating formulations were composed of WD 400, Germany). The Brookfield viscosity of each coating formulation was measured on a Brookfield DV3T instrument using spindle #2 at 200 rpm at 25°C. The formulation details and Brookfield viscosity are shown in Table 4.

[0179] Table 4: Brookfield Viscosities of Coating Formulations

[0180]

[0181] Test Methods for Evaluating Surfactant Examples: Each surfactant example was tested in a coating formulation using the following test method.

[0182] Foaming Evaluation: The foaming properties of the surfactant examples in the coating formulations were evaluated by using Red Devil TM 5400 paint mixer was measured by mixing 0.2 wt% surfactant in each coating formulation in a 4 oz glass jar for 5 minutes. The initial height of the liquid before mixing and the final height of the liquid plus 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.

[0183] Wetting Performance Evaluation: Wetting performance was evaluated by applying each coating formulation to a sealed Leneta TM The films were evaluated on a wet film thickness (WFT) chart (WB form B#5127). A new method was developed to better differentiate samples by stretching the films at 25 micron WFT, compared to the 100 micron WFT typically used in the industry. Using this new method, the differences between surfactant samples were better observed, helping to establish structure-property relationships. Wetting performance was visually rated for pinholes, pits, and other coating defects. A rating scale of 1 to 5 was used to record each stretch; for example, the worst wetting surfactant example was rated 1 and the best wetting surfactant example was rated 5.

[0184] Surfactant Performance Results: Table 5 gives the foam height of the example surfactants at 0.2 wt % surfactant solids in Coating Formulation A, Coating Formulation B, and Coating Formulation C, and Table 6 gives the application performance in terms of visual rating of substrate wetting.

[0185] Table 5: Foam height of Example surfactants in coating formulations A, B, and C

[0186]

[0187] XP 80 is a surfactant provided by BASF. 8-7 Ethoxylate is a surfactant supplied by Sasol Inc.

[0188] Table 6: Example surfactants in coating formulations A, B, and C in sealed Leneta TM Application performance on Chart.

[0189]

Claims

1. A surfactant comprising the 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 ratio of the molar equivalents of "Reactant A" to the molar equivalents of "Reactant B" is from about 1:0.5 to about 1:

4.

2. The surfactant according to claim 1, wherein the surfactant further comprises the 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.

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 surfactant according to claim 4, wherein the polyethylene glycol is 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, PEG3800, 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. A 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 monofunctional polyol and at least one multifunctional 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 comprises a polyol monofunctionalized with an alkyl glycidyl ether and a polyol multifunctionalized with an alkyl glycidyl ether.

11. A surfactant according to claim 10, wherein the reaction product of reactant A and reactant B comprises: (i) from about 0.05% to about 40.0% of a polyol monofunctionalized with an alkyl glycidyl ether; and (ii) from about 60.0% to about 99.95% of a polyol multifunctionalized with an 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 ratio of the molar equivalents of polyethylene glycol to the molar equivalents of 2-ethylhexyl glycidyl ether is about 1:

2.

14. A method for preparing the surfactant of claim 1 or 9, comprising: (i) about 1 molar equivalent of an aliphatic polyether polyol and (ii) about 2 molar equivalents of an epoxy compound are reacted 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 multifunctionalized with the epoxy compound.

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

16. The method according to claim 14, wherein the epoxy compound is an alkyl glycidyl ether or an allyl glycidyl 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 method according to claim 14, wherein the base is selected from: (i) an amine selected from 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.

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

20. A surfactant comprising the 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); in, One molar equivalent of PEG reacts with two 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, the general structure of which is: Among them, each C 11 H 22 The O2 unit is independently Among them, each C 11 H 22 The O2 unit is linked to the polyethylene glycol core or another C 11 H 22 O2 unit; Where n=2 to 90, and a+b=1 to 5, which includes: a+b=1, PEG monofunctionalized by EHGE; a+b=2, PEG difunctionalized by EHGE; a+b=3, PEG trifunctionalized by EHGE; a+b=4, PEG tetrafunctionalized by EHGE; and a+b=5, PEG pentafunctionalized by EHGE.

21. The surfactant according to claim 2, wherein the structure of the fatty alkoxylated alcohol is: wherein R is a straight or branched chain alkyl group having 1 to 20 carbons; R1=H and / or CH3, and n=1 to 25.

22. The surfactant according to claim 21, wherein the fatty alkoxylated alcohol is selected from C 2-6-hydroxy-1-nitro-2-ol having 3 to 23 ethoxylate units. 6-20 Alcohol ethoxylate.

23. A composition comprising: (i) from about 5.0% to about 99.5% by weight of the surfactant of claim 1 or 2; and (ii) from about 0.5% to about 95.0% by weight of at least one additive.

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

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

26. A coating composition comprising: (i) from about 0.1% to about 5.0% by weight of the surfactant of claim 1 or 2; (ii) from about 5.0% to about 85.0% by weight of at least one film-forming polymer; and (iii) from about 10.0% to about 94.9% by weight of at least one additive.

27. The coating composition of claim 26, wherein the film-forming polymer is selected from the group consisting of acrylic acid, ethylene acrylic acid, styrene-acrylic acid copolymers, styrene-butadiene copolymers, vinyl acetate-ethylene copolymers, butadiene-acrylonitrile copolymers, polyepoxides, polyurethanes, polyamides, urethane acrylates, vinyl esters of neodecanoic acid, and polyesters.

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

29. The coating composition of claim 28, wherein the pigment is selected from the group consisting of phthalocyanine, iron oxides, 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, wherein the composition is used for paint coatings, primer coatings, inkjet printing, top coatings, varnish coatings, architectural coatings, wood coatings, printing inks or metallic coatings or non-metallic coatings.

31. The coating composition according to claim 26, wherein the composition is coated on a substrate selected from the group consisting of porous and non-porous substrates, paper, nonwoven materials, textiles, leather, wood, concrete, masonry, metals, non-metals, house wraps, building materials, fiberglass, polymeric articles, face masks, medical drapes and gowns, carpets, upholstery, tents, awnings, air bags, fabrics, ceramics, yarns, and blended, woven, knitted, natural, synthetic, and recycled substrates.

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