Composition for Wetting of Hydrophobic Soils

Abstract

A mixture for treating a hydrophobic surface and a method for treating hydrophobic surfaces is provided. The mixture comprises: a wetting agent comprising; a compound of Formula I:

R.sup.1((CH.sub.2CH.sub.2O).sub.nR.sup.2).sub.x  Formula I wherein: R.sup.1 is a core group derived from a linear, cyclic or branched polyol with 1-55 carbons or a linear, cyclic or branched polyamine with 1-22 carbons wherein hydrogens on the alcohol group or hydrogens on the amine group are replaced with (CH.sub.2CH.sub.2O).sub.n or R.sup.1 is defined by —R.sup.6(—C(═O)O—).sub.m; R.sup.2 is a hydrophobic group preferably selected from the group consisting of R.sup.3, the elements necessary to form an ester, specifically —COR.sup.4, or the elements necessary to form a urethane, specifically —CONHR.sup.5; R.sup.3-R.sup.5 are each independently an alkyl of 6-22 carbons, wherein the alkyl is a linear, cyclic or branched and preferably linear; n, on average is 4-100; x is 2-20; R.sup.6 represents a bond or a linear, cyclic or branched alkyl with 6-22 carbons; and m is 2-20.

Claims

1. A mixture for treating a hydrophobic surface comprising: a wetting agent comprising; a compound of Formula I:
R.sup.1((CH.sub.2CH.sub.2O).sub.nR.sup.2).sub.x  Formula I wherein: R.sup.1 is a core group derived from a linear, cyclic or branched polyol with 1-55 carbons or a linear, cyclic or branched polyamine with 1-22 carbons wherein hydrogens on the alcohol group or hydrogens on the amine group are replaced with (CH.sub.2CH.sub.2O).sub.n or R.sup.1 is defined by —R.sup.6(—C(═O)O—).sub.m; R.sup.2 is a hydrophobic group preferably selected from the group consisting of R.sup.3, the elements necessary to form an ester, specifically —COR.sup.4, or the elements necessary to form a urethane, specifically —CONHR.sup.5; R.sup.3-R.sup.5 are each independently an alkyl of 6-22 carbons, wherein the alkyl is a linear, cyclic or branched and preferably linear; n, on average is 4-100; x is 2-20; R.sup.6 represents a bond or a linear, cyclic or branched alkyl with 6-22 carbons; and m is 2-20.

2. The mixture for treating a hydrophobic surface of claim 1 wherein each said hydrogens on said alcohol group or each said hydrogen on said amine group are replaced with (CH.sub.2CH.sub.2O).sub.n.

3. The mixture for treating a hydrophobic surface of claim 1 wherein said Formula I is defined by: ##STR00004## wherein e is 3-6.

4. The mixture for treating a hydrophobic surface of claim 1 wherein said R.sup.1 comprises 5-20 carbons.

5. The mixture for treating a hydrophobic surface of claim 1 wherein said R.sup.3-R.sup.5 are each independently an alkyl of 12-18 carbons.

6. The mixture for treating a hydrophobic surface of claim 1 wherein n on average is 6-30.

7. The mixture for treating a hydrophobic surface of claim 1 wherein x is 3-8.

8. The mixture for treating a hydrophobic surface of claim 1 wherein R.sup.6 has 12-18 carbons.

9. The mixture for treating a hydrophobic surface of claim 1 wherein said m is 2-8.

10. The mixture for treating a hydrophobic surface of claim 9 wherein said m is 2.

11. The mixture for treating a hydrophobic surface of claim 1 wherein said Formula I has an HLB 7-14.

12. The mixture for treating a hydrophobic surface of claim 1 wherein said compound of Formula I has a molecular weight of 1200-1800.

13. The mixture for treating a hydrophobic surface of claim 1 wherein said compound of Formula I has a hydroxyl number of 40.0-48.0.

14. The mixture for treating a hydrophobic surface of claim 1 wherein said wetting agent further comprising a compound defined by Formula II:
R.sup.8—O—(C.sub.2H.sub.4O).sub.b(C.sub.3H.sub.6O).sub.c—R.sup.8  Formula II wherein: b is 0 to 500; c is 0 to 500; and each R.sup.8 is independently H, or an alkyl group with 1 to 4 carbon atoms.

15. The mixture for treating a hydrophobic surface of claim 14 wherein said wetting agent comprises 1-95 wt % said Formula II.

16. The mixture for treating a hydrophobic surface of claim 14 wherein said compound defined by Formula II has a molecular weight of 300 to 51,000.

17. The mixture for treating a hydrophobic surface of claim 1 wherein said wetting agent further comprising a compound defined by Formula III:
R.sup.9—O—(CH.sub.2CH.sub.2O).sub.z(CHR.sup.10CH.sub.2O).sub.pR.sup.11  Formula III wherein: z is from 1 to 50; p is 0-50; R.sup.9 is a branched or linear alkyl, alkenyl, aryl or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.10 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.11 is selected from H and alkyl groups having from 1 to 30 carbon atoms.

18. The mixture for treating a hydrophobic surface of claim 17 wherein said wetting agent comprises 1-95 wt % said Formula III.

19. The mixture for treating a hydrophobic surface of claim 1 wherein said wetting agent further comprising a compound defined by Formula IV:
R.sup.12CO.sub.a(CH.sub.2CH.sub.2O).sub.q(CHR.sup.13CH.sub.2O).sub.rCO.sub.dR.sup.14  Formula IV wherein: q is from 1 to 50; r is 1-50; a is from 1 to 2; d is from 1 to 2; R.sup.12 is an alkyl or alkenyl group having up to 60 carbons or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.13 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.14 is selected from H and alkyl groups having from 1 to 30 carbon atoms.

20. The mixture for treating a hydrophobic surface of claim 19 wherein said wetting agent comprises 1-95 wt % said Formula IV.

21. The mixture for treating a hydrophobic surface of claim 1 further comprising a surfactant.

22. The mixture for treating a hydrophobic surface of claim 21 further wherein said surfactant is a silicone surfactant.

23. The mixture for treating a hydrophobic surface of claim 1 wherein said hydrophobic surface comprises soil.

24. The mixture for treating a hydrophobic surface of claim 1 further comprising water.

25. A method for treating a hydrophobic surface comprising: forming a wetting agent comprising; a compound of Formula I:
R.sup.1((CH.sub.2CH.sub.2O).sub.nR.sup.2).sub.x  Formula I wherein: R.sup.1 is a core group derived from a linear, cyclic or branched polyol with 1-20 carbons or a linear, cyclic or branched polyamine with 1-20 carbons wherein hydrogens on the alcohol group or hydrogens on the amine group are replaced with (CH.sub.2CH.sub.2O).sub.n or R.sup.1 is defined by —R.sup.6(—C(═O)O—).sub.m; R.sup.2 is a hydrophobic group preferable selected from the group consisting of R.sup.3, the elements necessary to form an ester, specifically —COR.sup.4, or the elements necessary to form a urethane, specifically —CONHR.sup.5; R.sup.3-R.sup.5 are each independently an alkyl of 6-22 carbons, wherein the alkyl is a linear, cyclic or branched and preferably linear; n, on average is 4-100; x is 2-20; R.sup.6 represents a bond or a linear, cyclic or branched alkyl with 6-22 carbons; and m is 2-20; and applying said wetting agent to said hydrophobic surface.

26. The method for treating a hydrophobic surface of claim 25 wherein each said hydrogens on said alcohol group or each said hydrogen on said amine group are replaced with (CH.sub.2CH.sub.2O).sub.n.

27. The method for treating a hydrophobic surface of claim 25 wherein said Formula I is defined by: ##STR00005## wherein e is 3-6.

28. The method for treating a hydrophobic surface of claim 25 wherein said R.sup.1 comprises 5-55 carbons.

29. The method for treating a hydrophobic surface of claim 25 wherein said R.sup.3-R.sup.5 are each independently an alkyl of 12-18 carbons.

30. The method for treating a hydrophobic surface of claim 25 wherein n on average is 6-30.

31. The method for treating a hydrophobic surface of claim 25 wherein x is 3-8.

32. The method for treating a hydrophobic surface of claim 25 wherein R.sup.6 has 12-18 carbons.

33. The method for treating a hydrophobic surface of claim 25 wherein said m is 2-8.

34. The method for treating a hydrophobic surface of claim 25 wherein said m is 2.

35. The method for treating a hydrophobic surface of claim 25 wherein said Formula I has an HLB 7-14.

36. The method for treating a hydrophobic surface of claim 25 wherein said applying is selected from the group consisting of dipping, spraying and wiping.

37. The method for treating a hydrophobic surface of claim 25 wherein said applying is done in a single-application or in multiple applications.

38. The method for treating a hydrophobic surface of claim 37 wherein said multiple applications are 7 to 10 days apart.

39. The method for treating a hydrophobic surface of claim 25 wherein said compound of Formula I has a molecular weight of 1200-1800.

40. The method for treating a hydrophobic surface of claim 25 wherein said compound of Formula I has a hydroxyl number of 40.0-48.0.

41. The method for treating a hydrophobic surface of claim 35 wherein said wetting agent further comprising a compound defined by Formula II:
R.sup.8—O—(C.sub.2H.sub.4O).sub.b(C.sub.3H.sub.6O).sub.c—R.sup.8  Formula II wherein: b is 0 to 500; c is 0 to 500; and each R.sup.8 is independently H, or an alkyl group with 1 to 4 carbon atoms.

42. The method for treating a hydrophobic surface of claim 41 wherein said wetting agent comprises 1-95 wt % said Formula II.

43. The method for treating a hydrophobic surface of claim 41 wherein said compound defined by Formula II has a molecular weight of 300 to 51,000.

44. The method for treating a hydrophobic surface of claim 25 wherein said wetting agent further comprising a compound defined by Formula III:
R.sup.9—O—(CH.sub.2CH.sub.2O).sub.z(CHR.sup.10CH.sub.2O).sub.pR.sup.11  Formula III wherein: z is from 1 to 50; p is 0-50; R.sup.9 is a branched or linear alkyl, alkenyl, aryl or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.10 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.11 is selected from H and alkyl groups having from 1 to 30 carbon atoms.

45. The method for treating a hydrophobic surface of claim 44 wherein said wetting agent comprises 1-95 wt % said Formula III.

46. The method for treating a hydrophobic surface of claim 25 wherein said wetting agent further comprising a compound defined by Formula IV:
R.sup.12CO.sub.a(CH.sub.2CH.sub.2O).sub.q(CHR.sup.13CH.sub.2O).sub.rCO.sub.dR.sup.14  Formula IV wherein: q is from 1 to 50; 6 is 1-50; a is from 1 to 2; d is from 1 to 2; R.sup.12 is an alkyl or alkenyl group having up to 60 carbons or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.13 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.14 is selected from H and alkyl groups having from 1 to 30 carbon atoms.

47. The method for treating a hydrophobic surface of claim 46 wherein said wetting agent comprises 1-95 wt % said Formula IV.

48. The method for treating a hydrophobic surface of claim 25 further comprising a surfactant.

49. The method for treating a hydrophobic surface of claim 48 further wherein said surfactant is a silicone surfactant.

50. The method for treating a hydrophobic surface of claim 25 wherein said hydrophobic surface comprises soil.

51. The method for treating a hydrophobic surface of claim 25 further comprising water.

Description

DESCRIPTION

[0042] The present invention is also related to a mixture for, and method of, enhancing water retention of soils and providing plant nutrients thereto over an extended period of time using capped PEG's. Furthermore, the present invention is generally related to the use of capped PEG's to enhance the infiltration of water and/or aqueous compositions through hydrophobic/water repellent soil. More particularly, the present invention is related to the use of capped PEG's to rapidly improve the hydrophilicity of such soil.

[0043] The invention is further related to a new method for improving the water transport characteristics of hydrophobic soils. The applicants have found that the application of certain hydrophobic, water insoluble polymers or blends thereof, to hydrophobic soil or turf will improve the ability of water to penetrate the soil surface and infiltrate the treated layers of soil.

[0044] This invention is also related to a method of treating turf and soil to alleviate drought stress and soil capping and to improve water conservation in soil. The instant invention further relates to a method of promoting the transport of water through medium and coarse-grained soils.

[0045] The present invention is related to capped PEG's, and the use thereof in wetting of soils, wherein the capped PEG comprises a core group, R.sup.1 as will be defined herein, with 2-20 PEG groups extending therefrom wherein the PEG groups have an average of 4-100 —CH.sub.2CH.sub.2O— groups and each PEG group is terminated with a hydrophobe.

[0046] Through diligent research it has been surprisingly realized that by changing the terminal hydroxyl groups of the PEG polymer to hydrophobic groups of sufficient size, the wetting agent can be sufficiently anchored to the hydrophobic soil particle surfaces thereby changing the surface to a hydrophilic one. These terminal hydrophobic groups, when chosen properly, continue to anchor the PEG chains so that they resist removal by multiple irrigation or rain events. It is believed that they also slow microbial attack and thus improve their durability in soil. The hydrophobic terminal groups may be connected to the PEG chain through ether, ester, or isocyanate linkages.

[0047] The present invention is related poly(ethylene glycol) (PEG) polymers capped on both ends with either ester, ether, or isocyanate groups of sufficient size which, when applied to hydrophobic soils or other plant growth media, the moisture transport and moisture retention properties are greatly enhanced. Plant health is also improved and the incidence of localized dry spot is reduced. These new polymer compositions do not require the incorporation of either random or block groups derived from propylene oxide (PO), also referred to as poly(propylene glycols) (PPG) which is contrary to the expectations in the art.

[0048] The capped PEG is generally defined by Formula I:

R.sup.1((CH.sub.2CH.sub.2O).sub.nR.sup.2).sub.x  Formula I

wherein:
R.sup.1 is a core group derived from a linear, cyclic or branched polyol with 1-20 carbons or a linear, cyclic or branched polyamine with 1-20 carbons, and more preferably 5-20 carbons, wherein the hydrogen on the alcohol group or the hydrogens on the amine group are replaced with a PEG; alternatively, R.sup.1 is defined by —R.sup.6(—C(═O)O—).sub.m;
R.sup.2 is a hydrophobic group preferably selected from the group consisting of R.sup.3, the elements necessary to form an ester, specifically —COR.sup.4, or the elements necessary to form a urethane, specifically —CONHR.sup.5;
R.sup.3-R.sup.5 are each independently an alkyl of 6-22 carbons, and more preferably 12-18 carbons, wherein the alkyl is a linear, cyclic or branched and preferably linear;
n, on average, is 4-100 and more preferably 6-30;
x is 2-20, and more preferably 3-8;
R.sup.6 represents a bond or a linear, cyclic or branched alkyl with 6-22 carbons and more preferably 12-18 carbons; and
m is 2-20, preferably 2-8 and most preferably 2.

[0049] The reaction to form embodiments of the invention from polyols is represented by Reaction Scheme 1:

##STR00001##

[0050] The reaction to form embodiments of the invention from polyamines is represented by Reaction Scheme 2:

##STR00002##

[0051] In Reaction Scheme 1 and Reaction Scheme 2, R.sup.1, R.sup.3-R.sup.5, n and x are as defined above. In Formula I and Reaction Schemes 1 and 2 the hydroxyl hydrogens and amine hydrogens are all illustrated as being reacted for convenience with the understanding that some hydroxyl hydrogens and some amine hydrogens may not be reacted due to kinetics, steric hindrances and the like as would be fully understood to those of skill in the art. In an embodiment all hydroxyl hydrogens or amine hydrogens are reacted in accordance with Reaction 1 or Reaction 2.

[0052] The core group can comprise a linear, cyclic or branched alkyl, aryl, alkaryl or alkenyl with 1-54 carbons, and more preferably 5-36 carbons, or a diester comprising the group —OC(═O)—R.sup.6—(C(═O)O—).sub.m-1 wherein R.sup.6 is a bond or a linear, cyclic or branched alkyl with 1-20 carbons. R.sup.1 can comprise, or R.sup.6 can represent cyclic alkyls of 4-8 carbons.

[0053] The longer the EO chain, the better the ability of the polymer when coated onto a hydrophobic surface to draw, or wick, water along the surface and the more water soluble or dispersible it becomes. However, the longer the EO chain, the more readily it may be rinsed off the surface of the soil particle. Therefore, it is preferable that the EO chain length be, on average, 4-100 EO units long, or —CH.sub.2CH.sub.2O— units, long. More preferably 6-30 EO units long

[0054] The longer the hydrophobe chain at the ends of the EO chain, the less water soluble or dispersible the capped PEG will be, and the better it will be at anchoring the polymer onto the surface of the soil particle. Thus, balancing the length of the EO chain to improve water movement must be balanced by increasing the length of the hydrophobe chain. Hydrophobes may be alkyls, aryls, alkaryls, alkenyls, or aromatic groups with five or greater carbon atoms. In general, the length of the hydrophobe chain is preferably at least six carbons and preferably not more than 22 carbons long, preferably at least 12 to no more than 18 carbons long.

[0055] The number of EO groups and the size of the hydrophobic chain terminating the EO groups are preferably chosen to obtain a hydrophilic/lipophilic balance (HLB) of 7-14.

[0056] The PEG chains may be present in the core of the molecule, as may be prepared by ethoxylating either glycerin or trimethylol propane, with 3 branches, or pentaerythritol, with 4 branches, or sorbitol, with 6 branches. The ethoxylated polyol would then be terminated with a hydrophobic group as described elsewhere herein resulting in a capped PEG having the formula:

##STR00003##

wherein e is 3 for when glycerin is the starting material, e is 4 for pentaerythritol as the starting material and is 6 for sorbitol as the starting material.

[0057] A multiply-branched PEG moiety is preferably capped with multiple hydrophobic groups to impart sufficient durability to function well. Preferably, all of the branches are capped with hydrophobic groups so that no uncapped chains remain that may reduce the durability of the coating on the soil particles.

[0058] Many of these capped PEG polymers have sufficient water solubility that they may be dispersed into water on their own and still impart a highly durable hydrophilic coating onto a hydrophobic soil particle. However, capped PEG polymers that are not readily dispersible in water may be combined with capped PEG polymers that are dispersible in water so that the combination is dispersible in water. These combinations may have the best resistance to rinsing off the treated soil.

[0059] The esterification of the alkoxylated product can be carried out by methods known such as by the use of acidic catalyst. Suitable acidic catalysts for this purpose are, for example, methanesulfonic acid, butanesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid, alkyl benzenesulfonic acid and/or sulfosuccinic acid.

[0060] In addition, it is advisable to carry out the esterification reaction at elevated temperatures, for example at temperatures of 140° to 275° C. and preferably 150° to 185° C. and continuously to remove the water of reaction from the equilibrium. The quantity of fatty acid used should be selected so that there are 1.0 to 1.2 and preferably 1.0 to 1.1 moles of fatty acid for every mole of the polyethylene oxide, C.sub.1-C.sub.24 alkyl ether alkoxylate. This ensures that the esterification of the hydroxyl groups is substantially quantitative. If desired, a residual content of free fatty acid in the end reaction product may be neutralized with alkali metal hydroxide solution.

[0061] The emulsion of the capped PEG polymer of Formula I may then be conveniently applied to the hydrophobic surface or soil by any of a number of methods including dipping, spraying, or wiping the emulsion onto the surface to be treated. After drying to remove the water vehicle, a coating of the inventive polymer remains on the treated surface rendering it hydrophilic. The hydrophilic coating is durable to repeated rinsings with water.

[0062] A thin coating of the capped PEG polymer of Formula I on the hydrophobic surfaces or soils is adequate to render it hydrophilic. Application of larger amounts of the polymer of Formula I to a hydrophobic surface to make a thicker coating will not necessarily improve its hydrophilicity.

[0063] Amounts of the inventive polymer coating or emulsion necessary for adequate wettability of the hydrophobic surface or soil will vary with the desired level of hydrophilicity and depth of coverage. Moisture movement through treated soils will be improved according to the depth of treatment. Accordingly, the amount of dilution of the polymer of Formula I with water and emulsifiers will best be determined by consideration of the depth of the root zone and the amount of diluted emulsion needed to percolate down to the desired depth. The concentration and volume of the emulsion of the inventive polymer may then be adjusted so that the volume of water and emulsion is sufficient to carry the polymer down to the desired depth to treat the soil particle surfaces.

[0064] In general, the polymers of Formula I have low water solubility and some will separate when added to water. These must be emulsified into water for delivery to the hydrophobic soils to be treated via a water spray or other irrigation method. If necessary, the polymers of Formula I may be emulsified in water with any of a number of emulsifiers. Emulsifiers may be chosen to give best stability of the polymer of Formula I in a concentrated form as well as in diluted form for application to hydrophobic surfaces or soils. Preferred emulsifiers include nonionic surfactants, and especially preferred are nonionic ethylene oxide/propylene oxide block copolymers. A surface tension reducing additive may optionally be added to ensure adequate wetting of the hydrophobic surface or soil. Emulsifiers for soil application should be chosen so as not to damage turf or plant life.

[0065] Polymers of Formula I can be diluted in water emulsion to 2% active ingredient or less for application to soil or to hydrophobic surfaces. The diluted solution may be applied to soil at a rate sufficient to allow treatment of the soil surface to a depth to encompass the entire turf root zone.

[0066] The treated hydrophobic surface becomes rapidly wettable by water, and will cause the treated surface to wick water (cause water to rise vertically up a treated surface). In the case of soils, the ability of water to penetrate soils is greatly increased. Dew formation on treated surfaces such as grass is also prevented.

[0067] The compounds of Formula I thus exhibit excellent ability to provide the necessary water adhesion to the hydrophobic surface of the water repellent soil via the hydrophobic groups of the surfactant itself and therefore provide the beneficial wetting characteristics and thus water transport, through the hydrophobic soil. Any adhered water droplets will be pulled into the sand and/or soil by further adhesion by other particles or through cohesion with other water droplets. Thus, such a wetting agent effectively permits appreciable and necessary amounts of moisture to penetrate the topsoil for beneficial moisture supply to the subterranean roots on a consistent and continuous basis for a relatively long period of time.

[0068] The compounds of Formula I are useful for improving the water transport characteristics of hydrophobic surfaces.

[0069] The invention is also directed to a method for improving the water penetration rate through hydrophobic surfaces, inhibiting the formation of dew on grass, other plant surfaces, or other hydrophobic surfaces by applying an effective amount of a mixture of compounds having the Formula I as defined above. The invention further provides a process for increasing the wetting rate of water repellent soil which comprises the steps of: (i) preparing an aqueous wetting agent composition comprising: (a) a compound of the Formula I (b) optionally a surfactant, and (c) water; and (ii) intimately contacting the water repellent soil with an effective amount of the wetting agent composition.

[0070] The instant invention also provides a process for rapidly increasing the hydrophilicity and infiltration of water into water repellent soil matrices. The process consists of applying to the water repellent soil an effective amount of a wetting agent composition comprising a mixture of the Formula I.

[0071] The invention also provides a method for improvement and prevention of dry spots on the grass surface of a golf course comprising applying an effective amount of a mixture of the Formula I. An effective amount is that amount sufficient to improve the wetting rate of the hydrophobic soil. An effective amount is typically about 0.5 to about 20 ounces of wetting agent per 1000 ft.sup.2 of surface. More preferably the effective amount is about 1 to about 10 ounces of wetting agent per 1000 ft.sup.2 of surface. Even more preferably the effective amount is about 3 to about 7 ounces of wetting agent per 1000 ft.sup.2 of surface. If the application is below the effective amount dark spots will occur. If the application is above the effective amount no additional benefits are observed and material is wasted which is undesirable.

[0072] The compositions of the invention unexpectedly exhibit significantly enhanced infiltration, or wetting, rates in water repellent soil over that previously achieved in the prior art.

[0073] The compounds of Formula I are prepared in accordance with Reaction Scheme 1 or 2 by alkoxylation with the required amount of ethylene oxide in the presence of potassium hydroxide at a temperature between 100° C. and 150° C. and more preferably at about 130° C. After the initial reaction, the residual volatiles are removed by stirring under vacuum such as for 30 minutes at 120° C. If required, depending on the degree of ethoxylation one desires, additional ethylene oxide may be optionally added at about 140° C. and allowed to react completely. Residual volatiles would then again be removed by stirring under vacuum such as for 30 minutes at about 120° C. The temperature would then be reduced to about 60° C. and phosphoric acid would be added and stirred for about 30 minutes. The resulting product is typically a viscous clear oil having a molecular weight (MW) in the range of approximately 1200-1800 typically with a hydroxyl number in the range of 40.0-48.0.

[0074] The clear oil above is then heated to a temperature between about 80° C. and about 90° C. and then a fatty acid is added in the presence of an acid esterification catalyst. The mixture is heated to about 180°-190° C. with a nitrogen sparge for about 35-40 hours with water distillate being removed. The product ester is then cooled to about 85°-90° C. and then sodium carbonate is added and stirred for about 1 hour. Subsequently, about 50% hydrogen peroxide is added and allowed to stir for about 1 hour. After heating to about 100°-110° C., vacuum is applied and water removed. The resulting mass is cooled to about 50°-60° C. and filtered to remove suspended solids. The product is a viscous clear liquid having the desired acid values, hydroxyl number and saponification value.

[0075] After the alkoxylation, the alkoxylated alcohols formed as intermediate products are subjected to esterification. The carboxylic acid component used for this purpose would be selected from linear or branched saturated or unsaturated fatty acids having 1 to 24 carbon atoms. The fatty acid chain may also be substituted with hydroxyl groups.

[0076] Typical examples of the fatty acid esterifying agents include lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, 12-hydroxystearic acid, arachidonic acid, gadoleic acid, behenic acid, dimeric fatty acids, dimeric acids of the above fatty acids and erucic acid. Oleic acid, stearic acid and isostearic acid and technical mixtures thereof are preferred.

[0077] As usual in oleochemistry, these acids may also be present in the form of the technical cuts obtained in the pressure hydrolysis of natural fats and oils, for example palm oil, palm kernel oil, coconut oil, olive oil, sunflower oil, rapeseed oil or beef tallow. Fatty acids containing 12 to 18 carbon atoms are preferred, those containing 16 to 18 carbon atoms being particularly preferred.

[0078] The instant invention specifically relates to the discovery that wetting agent compositions comprising compounds of the Formula I significantly and unexpectedly enhance water and aqueous composition transport or infiltration through the solid matrices of hydrophobic/water repellent soil, as well as or better than ethylene oxide and propylene oxide copolymers. Additionally, it has been found that these compositions are highly efficacious over a wide range of concentrations which is of critical importance in achieving maximum agronomic and/or hydrological benefit when the compositions are to be used in irrigation scenarios. The benefit is realized in the reduction in run-off and in the delivery of water-soluble fertilizers.

[0079] Additionally, the compounds of Formula I of the invention are formulated as an additive for hydrophobic soil for treating sandy areas, soils, or areas including both sand and soil; such as lawns, greens, pastures, beaches, dry desert-like areas, and the like; for effective moisture penetration. The formulations of the invention are also used for reducing localized dry spot formation within lawns or greens by providing long-term wetting treatments comprising the application of a soil additive formulation to a target lawn or green, wherein said soil additive formulation comprises the compounds of Formula I as noted above. The application can be done in a single-application, in a split application spaced 7 to 10 days apart formulations, or in other frequencies as necessary.

[0080] The formulations containing the compounds of Formula I and the method of treating sandy areas with such formulations may thus be utilized for the provision of moisture penetration benefits in sandy areas alone. In such a manner, the sandy area, such as a beach, may be modified to permit water penetration therein, to prevent unsightly water pools, for example, after raining, or to dry desert-like areas in order to permit water penetration to sustain root systems of plant-life which would not grow otherwise.

[0081] The compounds of Formula I exhibit an excellent ability to provide the necessary water adhesion to the otherwise hydrophobic surface of the water repellent soil via the hydrophobic groups of the surfactant itself and therefore provide the beneficial wetting characteristics and water transport properties through the hydrophobic soil. Any adhered water droplets will be pulled into the sand and/or soil by further adhesion by other particles or through cohesion with other water droplets. The wetting agent effectively permits appreciable and necessary amounts of moisture to penetrate the topsoil for beneficial moisture supply to the subterranean roots on a consistent and continuous basis for a relatively long period of time.

[0082] The soil additive formulation may comprise a wetting agent consisting essentially of Formula I or, in an embodiment, the wetting agent may comprise about 0.1-99% by weight compounds of Formula I with additional wetting agents; more preferably the wetting agent comprises about 1-99% by weight Formula I; even more preferably about 5-95% by weight Formula I; more preferably about 10-90% by weight Formula I, with the remainder a mix of other additives as noted below.

[0083] In order to best ensure initial penetration of the wetting agents within the target topsoil areas, it is preferable to include at least one secondary compound within the formulation for further lowering of the surface tension at the topsoil surface which is also compatible with the aforementioned wetting agent having Formula I. The lowering of the surface tension allows more rapid penetration of the wetter into the soil profile. Such a secondary compound can be an alkoxylated, preferably ethoxylated alcohol surfactant, such as a branched or unbranched C.sub.6-C.sub.60 alcohol ethoxylate or alkoxylated, preferably ethoxylated C.sub.8-C.sub.40 fatty acid for utilization in combination with the aforementioned wetting agent of Formula I.

[0084] The alkoxylated secondary compounds may be branched or unbranched in configuration. Examples of preferred types of alcohol alkoxylates for this purpose include C.sub.6-C.sub.60 alkyl, or alkylaryl EO/PO surfactants, linear or branched, and secondary or primary hydroxyl in type, including mixtures of surfactants comprising from 1 to 95 wt % of at least one surfactant selected from polyalkylene oxide compounds having general Formula II, general Formula III or general Formula IV wherein general Formula III is:

R.sup.8—O—(C.sub.2H.sub.4O).sub.b(C.sub.3H.sub.6O).sub.c—R.sup.8  Formula II

wherein b is 0 to 500; c is 0 to 500; and each R.sup.8 is independently H, or an alkyl group with 1 to 4 carbon atoms; wherein the polyalkylene oxide has a preferred molecular weight in the range of 300 to 51,000; and a second optional different surfactant comprising a compound of general Formula III:

R.sup.9—O—(CH.sub.2CH.sub.2O).sub.z(CHR.sup.10CH.sub.2O).sub.pR.sup.11  Formula III

wherein z is from 1 to 50; p is 0-50; R.sup.9 is a branched or linear alkyl, alkenyl, aryl or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.10 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.11 is selected from H and alkyl groups having from 1 to 30 carbon atoms. Suitable secondary surfactants also include carboxylic and dicarboxylic esters of the general Formula V:

R.sup.12CO.sub.a(CH.sub.2CH.sub.2O).sub.q(CHR.sup.13CH.sub.2O).sub.rCO.sub.dR.sup.14  Formula IV

wherein q is from 1 to 50; r is 1-50; a is from 1 to 2; d is from 1 to 2; R.sup.12 is an alkyl or alkenyl group having up to 60 carbons or an aryl group optionally having an alkyl group substituent, the alkyl group having up to 60 carbon atoms; R.sup.13 is selected from H and alkyl groups having from 1 to 2 carbon atoms; and R.sup.14 is selected from H and alkyl groups having from 1 to 30 carbon atoms.

[0085] Additional secondary compounds can also be silicone surfactants, alkyl polyglycosides, alkyl sulfonates, alkyleth sulfonates, alkyl sulfosuccinates, or alkaryl sulfonates which are widely known by those skilled in the art to reduce surface tension.

[0086] The compounds of Formula I can also prevent development of dry spots on the grass surface of a golf course and also improve and reduce already developed dry spots by sprinkling said compound along with a carrier on the grass surface of a golf course.

EXAMPLES

Soil Wettability/Durability Testing

[0087] Hydrophobicity of fabric. As a control, a swatch of unfinished woven polypropylene fabric was dipped into isopropyl alcohol (IPA) to remove any surface treatment. The alcohol was subsequently evaporated from the fabric by suspending it in an ambient air flow for 24 hours, leaving nothing on the control. The wettability of the fabric was then tested by gently applying a droplet of water to the surface of the fabric and observing the time required for complete absorption of the droplet. Control 1 confirms that the untreated polypropylene fabric was very hydrophobic and not water-wettable.

TABLE-US-00001 TABLE 1 Example Control 1 Example 1 product 0 isopropyl alcohol 100% Wet pick up 100% Amount surfactant deposited  0% Time to absorbance of water droplet no absorption within 10 minutes

[0088] Wettability of hydrophobic fabric—Application of surfactants to impart hydrophilicity to a hydrophobic surface. A solution of 2.0% of surfactant(s) and either A) 98% demineralized water (DMW) or B) 1:1 DMW:anhydrous isopropyl alcohol (IPA) was prepared. The solution was applied to a finish-free polypropylene fabric by a dip method so that the wet-pick-up of the fabric was 100%. The diluent was subsequently evaporated from the fabric by suspending it in an oven for until dry, leaving 2% by weight of the surfactant(s) on the test fabric. The wettability of the fabric was then tested by gently applying a droplet of water to the surface of the fabric and observing the time required for complete absorption of the droplet.

[0089] Durability of hydrophilic treatment. After measuring the 2% treated fabric swatch for wettability, the swatch was immersed fully in ambient tap water and then dried in an oven. After removing from the oven and cooling, the wettability of the fabric was then tested by gently applying a droplet of water to the surface of the fabric and observing the time required for complete absorption of the droplet. This cycle of rinsing, drying, and retesting was repeated generating samples which were tested for up to 5 rinses or >60 seconds for full absorption time, whichever happened first.

Results of Soil Wettability and Durability Testing

[0090] Examples tested are in Table 2. Examples were tested in 2% DMW for soil wetting and durability with results reported in seconds with <1 indicating less than 1 second and more than 60 seconds indicated by >60 in Tables 3-5.

TABLE-US-00002 TABLE 2 Noted on Tables Example 3-5 as Blend of EO/PO block copolymers, dioleate and STD PO1 sodium dioctyl sulfosuccinate difunctional EO/PO block copolymer, 80% PO STD PO2 reverse block copolymer, 74% PO, 26% EO STD PO3 POE (50) Sorbitol hexaoleate F1-1 PEG 600 dioleate F1-2 POE (50) Sorbitol oleic coconut mixed fatty acid F1-3 ester 1:3 blend of POE (26) Castor oil trilaurate:PEG 600 F1-4 Dioleate 1:1 blend of POE (26) Castor oil trilaurate:PEG 600 F1-5 Dioleate 3:1 blend of POE (26) Castor oil trilaurate:PEG 600 F1-6 Dioleate PEG 6000 distearate F1-7 PEG 400 distearate F1-8 POE (150) Pentaerythritol tetrastearate F1-9 POE (26) Glycerin mono-oleate F1-10 POE (26) Glycerin dioleate F1-11 POE (26) Glycerin trioleate F1-12 POE (26) Glycerin dicocoate F1-13 POE (26) Glycerin tricocoate F1-14 POE (12) lauryl alcohol dimer acid diester F1-15 POE (23) lauryl alcohol dimer acid diester F1-16 POE (30) Pentaerythritol tetrastearate F1-17 POE (37) Ethylene diamine tetraoleate F1-18 POE (37) Ethylene diamine tetraoleate F1-19 Blend of POE (26) Glycerin hydroxystearic acid F1-20 ester, PEG 600 dioleate, and sodium dioctyl sulfosuccinate POE (12) lauryl alcohol adipic acid diester F1-21 POE (23) lauryl alcohol adipic acid diester F1-22 POE (12) lauryl alcohol terephthalic acid ester F1-23

TABLE-US-00003 TABLE 3 STD STD STD PO 1.sup.1 PO 2.sup.1 PO 3.sup.1 F1-1.sup.1 F1-2.sup.1 F1-3.sup.1 F1-4.sup.1 F1-5.sup.1 F1-6.sup.1 Initial <1 <1 <1 <1 <1 1.84 <1 <1 <1 1 rinse <1 1.99 1.97 <1 <1 2.10 <1 <1 <1 2 rinse 1.09 >60 >60 <1 1.29 >60 2.36 1.08 <1 3 rinses 1.22 <1 5.67 7.68 1.41 <1 4 rinses 1.52 3.51 >60 >60 2.1 <1 5 rinses 1.77 6.05 12.21 1.42 .sup.1in DMW

TABLE-US-00004 TABLE 4 F1-7.sup.1 F1-8.sup.1 F1-9.sup.1 F1-10.sup.1 F1-11.sup.1 F1-12.sup.2 F1-13.sup.1 F1-14.sup.2 F1-15.sup.1 Initial >60 4.40 6.59 12.63 5.99 3.27 2.06 1.71 2.60 1 rinse 6.58 19.28 >60 >60 3.52 20.31 2.50 4.58 2 rinse 6.53 29.25 3.72 >60 3.46 8.67 3 rinses 7.78 2.63 14.21 19.65 4 rinses 8.33 2.67 14.93 29.69 5 rinses 9.69 2.47 >60 32.97 .sup.1in DMW .sup.2in 1:1 DMW:IPA

TABLE-US-00005 TABLE 5 F1-16.sup.2 F1-17.sup.1 F1-18.sup.1 F1-19.sup.2 F1-20.sup.1 F1-21.sup.1 F1-22.sup.1 F1-23.sup.1 Initial 12.39 <1 3.46 2.20 3.74 1.91 12.68 <1 1 rinse 43.25 <1 4.05 2.57 4.00 3.00 17.11 <1 2 rinse >60 1.03 5.25 3.14 5.63 2.44 53.26 1.05 3 rinses 4.03 5.71 2.91 20.33 1.59 >60 2.41 4 rinses >60 4.85 3.06 >60 1.31 27.32 5 rinses 3.01 2.93 1.35 >60 .sup.1in DMW .sup.2in 1:1 DMW:IPA

[0091] Test data presented in Table 1 and Tables 3-5 is time in seconds for a water droplet placed on a cloth sample to wick into the sample. The rate at which the water droplet wicks into the sample is representative of the ability of the water droplet to wet hydrophobic soil after treatment with shorter times being preferred. PO-containing wetting agents were used as standards for comparison. Soil wettability is determined in the initial reading. Durability is determined through multiple rinse cycles.

[0092] Not all results are presented for all samples.

[0093] The invention has been described with reference to preferred embodiments without limit thereto. One of skill in the art would realize additional embodiments which are described and set forth in the claims appended hereto.