WO2008134389A1

WO2008134389A1 - Novel alkoxylate-containing compositions

Info

Publication number: WO2008134389A1
Application number: PCT/US2008/061364
Authority: WO
Inventors: Johan A. Thoen; Camiel F. Bartelink; Pierre T. Varineau
Original assignee: Dow Global Technologies Inc.
Priority date: 2007-04-27
Filing date: 2008-04-24
Publication date: 2008-11-06
Also published as: CA2685319A1; BRPI0809790A2; EP2152653A1; MX2009011606A; JP2010526778A; RU2009143873A; CN101668728A

Abstract

Compositions comprising novel alkylene oxide-extended alkoxylates of a linear or branched 1,3-dialkyloxy-2-propanol are disclosed. In these compositions the alkoxylates may offer a variety of desirable properties, including but not limited to service in formulations as surfactants, detergents, wetting agents, defoam/low foam agents, stabilizers, and the like. The compositions may include products such as detergents, pharmaceuticals, paints and coatings, plastics, oilfield chemicals, agricultural agents, and the like.

Description

NOVEL ALKOXYLATE-CONTAINING COMPOSITIONS

BACKGROUND OF THE INVENTION

1. Technical Field

[0001] This invention relates to the field of alkyloxy-ether alkoxylates. More particularly, it relates to compositions and processes using novel alkyloxy-ether alkoxylates.

2. Background of the Art

[0002] Surfactants are used in the chemical and manufacturing industries for a wide variety of purposes. These include, for example, imparting wettability and detergency in products including wetting agents, emulsifiers, rinse aids, defoam/low foam agents, spray cleaning agents, drug delivery agents, emulsifiers for herbicides and pesticides, metal cleaning agents, paints, coatings, agricultural spread and crop growth agents, stabilizing agents for latexes, paints and paper processing and products, and the like. One group of frequently-employed surfactants is the nonionic surfactants. The nonionic surfactants tend to be generally less sensitive to hard water and to generate less foam than some other types of surfactants, making many of nonionic surfactants useful as foam suppressants. Unfortunately, however, many of these surfactants in current use are alkylphenol-based compounds. Alkylphenol-based compounds have recently come under environmental scrutiny, and thus, compositions such as formulations and products containing them may eventually face restrictions.

[0003] Thus, there is a need in the art to identify compositions such as formulations and products that employ non-ionic surfactants that are not based on alkylphenols.

SUMMARY OF THE INVENTION

[0004] Accordingly, the present invention provides, in one aspect, a composition comprising a linear or branched alkylene oxide-extended 1 ,3-dialkyloxy-2-propanol alkoxylate.

[0005] In another aspect, the present invention provides a method of preparing a composition comprising incorporating in a composition a linear or branched alkylene oxide-extended 1 ,3-dialkyloxy-2-propanol alkoxylate.

DETAILED DESCRIPTION OF THE INVENTION

[0006] The compositions of the invention are in many cases made in a convenient and cost-effective manner, using any of a variety of novel linear or branched, alkylene oxide-extended 1 ,3-dialkyloxy-2-propanol alkoxylates. Preparation of the alkoxylates is described hereinbelow, and also described in detail in co-filed provisional patent applications (Attorney Docket Nos. C-65,202P and C- 65,205P), which are incorporated herein by reference in their entireties. [0007] The starting materials include, first, epichlorohydrin, also termed 1 - chloro-2,3-epoxypropane. Those skilled in the art will be aware of a large number of commercial sources for this material, which may be generally prepared by the reaction of propylene and an allyl chloride, or, for instance, by the conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, such as is described in WO 2006020234 A1 , the disclosure of which is incorporated herein by reference in its entirety.

[0008] The second starting material is an alcohol, which may be linear or branched. This alcohol, in some non-limiting embodiments, has from 3 to 28 carbon atoms, and in other non-limiting embodiments, has from 4 to 12 carbon atoms. In particularly preferred embodiments the alkyl chain may include from 6 to 10 carbon atoms. The alcohol may be a primary, secondary or tertiary alcohol; may be saturated or unsaturated; and may optionally contain one or more heteroatoms. For example, in certain non-limiting embodiments appropriate selections may include renewable feedstocks, such as bio-glycerin; 2-ethylhexanol; certain NEODOL™ branched alcohols marketed by Shell Chemical Company; certain EXXAL™ branched alcohols marketed by Exxon-Mobil Corporation; combinations thereof; and the like. In other non-limiting embodiments, suitable alcohols may include, for example, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, 4-propyl-1 -decanol, 3-butyl-1 -nonanol, 2-methyl-4- propyl-1 -decanol, 3-methyl-1 -heptanol, 3-methyl-2-heptanol, 3-methyl-3-heptanol, 2- ethyl-1 -hexanol, 2-methyl-1 -heptanol, 2-methyl-1 -pentanol, combinations thereof, and the like. Thus, in certain non-limiting embodiments the alcohol may be selected such that it contains as its alkyl moiety a moiety selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl aliphatics; methyl-, ethyl-, propyl- and butyl-branched pentyl-, hexyl-, heptyl-, octyl-, nonyl-, decyl-, undecyl-, dodecyl- and tridecyl- aliphatics; combinations thereof; and the like. In certain non-limiting embodiments the alcohol may be, for example, a branched heptanol, or a linear or branched alcohol produced according to methods such as those described in WO 2003024910 A1 , assigned to Sasol Tech PTY LTD, the disclosure of which is incorporated herein by reference in its entirety. For example, in certain non-limiting embodiments, 2-methylpentanol or 2-methylheptanol may be selected.

[0009] The alcohol may also optionally contain, as heteroatoms, elements selected from Groups IVA, VA, VIA and VIIA of the Periodic Table of the Elements, including, but not limited to, elements such as sulfur, phosphorus, and silicon; non- metals such as nitrogen, fluorine and oxygen; combinations thereof; and the like. [0010] The first step to prepare the alkoxylate is to react the epichlorohydrin with a stoichiometric excess of the alcohol. Such requires addition of the epichlorohydrin in any manner in which the desired stoichiometric excess may be maintained. For example, on a large or commercial scale, the epichlorohydrin may be added to the alcohol continuously. In contrast, on a smaller scale (e.g., laboratory scale), a "stepwise" manner may be more conveniently employed. This may comprise adding an amount of the epichlorohydrin in each of at least three steps, and in some non- limiting embodiments, in each of at least five steps. Time between steps may be varied, provided that the desired excess of alcohol is maintained throughout the reaction. In certain non-limiting embodiments, that time may be from about 30 minutes to about 90 minutes; in other non-limiting embodiments, it may be from about 45 minutes to about 75 minutes; and in still other non-limiting embodiments, it may be about 60 minutes. The stepwise addition may be particularly helpful in controlling the exotherm for such small-scale reactions.

[0011] The stoichiometric excess is defined herein as meaning that, at all times throughout the reaction, the alcohol is present in the reaction in an amount that is at least three times the stoichiometric amount based on the epichlorohydrin, i.e., the alcohol:epichlorohydrin molar ratio is at least about 3:1 . However, it has been found useful in some embodiments to begin with a much greater excess of the alcohol, such as from about 10:1 to about 20:1 , and then to increase the relative amount or rate of addition of epichlorohydrin until, toward the end of the reaction, there is approximately a 3:1 alcohol:epichlorohydrin ratio. In other non-limiting embodiments, successful reactions may be carried out by maintaining ratios of from about 15:1 to about 16:1 throughout most of the reaction, whether the epichlorohydrin is being added stepwise or continuously, and then increasing the amount or rate of addition of epichlorohydrin toward the end of the reaction such that the ratio of alcohol:epichlorohydrin drops to about 3:1 . In addition to aiding exotherm control, employing such a controlled protocol in incorporating the epichlorohydrin into the reaction may assist in reducing the amount of so-called heavies. These heavies, which result from further reaction of the alkyloxy-ether, are impurities in the end product that have a boiling point that is higher than that of the desired alkyloxy-ether.

[0012] This reaction also desirably includes the presence of an alkaline environment and a phase transfer catalyst. The alkaline environment may be obtained by addition of a metal hydroxide, including a Group 1 A metal, for example, sodium hydroxide or potassium hydroxide. In certain non-limiting embodiments, the metal hydroxide may be combined with the alcohol prior to addition of the epichlorohydrin, while in other, though in some cases less preferred, embodiments, the metal hydroxide and alcohol may be combined simultaneously with the epichlorohydrin.

[0013] Overall molar proportions of the alcohol, metal hydroxide and epichlorohydrin may range, and/or be varied, in certain non-limiting embodiments, from about 1 /0.7/0.06 to a final molar ratio of from about 1 /0.7/0.2 to 1 /0.7/0.33, and, in a particular embodiment, to about 1/0.7/0.3. In other non-limiting embodiments, the proportion of alcohol/metal hydroxide/epichlorohydrin, either immediately following each addition of the epichlorohydrin where such is done stepwise, or in continuous productions, throughout most of the duration of the reaction, may range from about 1/0.7/0.01 to about 1/0.7/0.8, preferably from about 1/0.7/0.02 to about 1/0.7/0.1 , and more preferably from about 1/0.7/0.05 to about 1/0.7/0.07. In certain non-limiting embodiments this ratio may be ramped up, toward the end of the reaction, to range from about 1/0.7/0.2 to 1/0.7/0.33, preferably about 1/0.7/0.33. [0014] The phase transfer catalyst used for the reaction between the alcohol and the epichlorohydrin may be selected from those typically known to those skilled in the art. For example, those that may be selected include salts having anions selected from the group consisting of halide, methylsulfate, and hydrogensulfate, such as alkyldimethylbenzylammonium salt, tetraalkylammonium salt, N,N,N-trialkyl- 3-alkyloxy-2-hydroxypropylammonium salt and alkyltrimethyl-ammonium salt. Other examples include trialkylamine, N,N-dialkylamino-3-alkyloxy-2-propanol, tetrabutylammonium bromide, tetrabutylammonium hydrogensulfate, cetyltrimethylammonium chloride, lauryldimethylbenzyl-ammonium chloride, N, N- dimethylamino-3-hexyloxy-2-propanol, N,N-dimethyl-amino-3-octyloxy-2-propanol, N,N-dimethylamino-3-dodecyloxy-2-propanol, N,N-dimethylamino-3-octadecyloxy-2- propanol, N,N-dimethylamino-3-(1 Η,1 Η,2'H,2Η-perfluoro)hexyloxy-2-propanol, N,N-dimethyl-amino-3-(1 Η,1 Η,2Η,2Η-perfluoro)-octyloxy-2-propanol, N,N-bis(2- hydroxyethyl)-amino-3-hexyloxy-2-propanol, N,N-bis(2-hydroxyethyl)amino-3- octyloxy-2-propanol, N,N-bis(2-hydroxyethyl)amino-3-dodecyloxy-2-propanol, N, N- bis(2-hydroxyethyl)amino-3-octadecyloxy-2-propanol, N,N-bis(2-hydroxyethyl)- amino-3-1 Η,1 Η,2'H,2Η-perfluoro)hexyloxy-2-propanol, N,N-bis(2-hydroxypropyl- ammonium methylsulfate, N,N,N-trimethyl-3-octyloxy-2-hydroxypropylammonium methylsulfate, N,N,N-trimethyl-3-dodecyloxy-2-hydroxy-propylammonium methylsulfate, N,N,N-thmethyl-3-octyloxy-2-hydroxypropyl-ammonium chloride, N, N, N- trimethyl-3-octyloxy-2-hydroxypropylammonium bromide, N,N-bis(2-hydroxyethyl)-N- methyl-3-hexyloxy-2-hydroxypropylammonium methylsulfate, N,N-bis(2-hydroxy- ethyl)-N-methyl-3-octyloxy-2-hydroxypropyl-ammonium methylsulfate, N,N-bis(2- hydroxyethyl)-N-methyl-3-dodecyloxy-2-hydroxypropylammonnium methylsulfate, N,N-bis(2-hydroxyethyl)-N-methyl-3-octadecyloxy-2-hydroxpropylammonium methylsulfate, N,N-bis(2-hydroxyethyl)-N- methyl-3-(1 'H,1 'H,2'H,2'H-perfluoro)- hexyloxy-2-hydroxy-propylammonium methyl-sulfate, N,N-bis(2-hydroxyethyl)-N- methyl-3-(1 Η,1 Η,2'H,2Η-perfluoro)-octyloxy- 2-hydroxypropylammonium methylsulfate, an esterified compound of octanoic acid and N,N-dimethyl-3-oxtyloxy-2- propanol, an esterified compound of hexadecanoic aid and N,N-dimetyl-3-octyloxy- 2-propanol, and the like. Combinations of any of the above may alternatively be selected.

[0015] The reaction of the epichlorohydrin and alcohol is desirably carried out at a temperature of from about 1 O⁰C to about 100⁰C and a pressure of from about 1 atmosphere (atm) to about 10 atm, i.e., about 760-7600 Torr. Appropriate mixing of the reactants to maximize contact thereof is desirable upon, and during, each addition of the epichlorohydrin. Such may be accomplished by any means or method known to those skilled in the art, such as, for example, an impeller mixer, a blade mixer, a recirculation mixer, or the like.

[0016] The result of the reaction is formation of a reaction product. This reaction product may be, in certain non-limiting embodiments, primarily a dialkyl-ether of the selected alcohol, with good selectivity at the 1 - and 3-positions. In other non-limiting embodiments, the linear or branched 1 ,3-dialkyl-ether may be at least about 50 percent; in other non-limiting embodiments, the 1 ,3-dialkyl-ether may be at least about 65 percent; and in still other non-limiting embodiments, the 1 ,3-dialkyl-ether may be at least about 75 percent; all based on the weight of the reaction product, i.e., not including the unreacted alcohol.

[0017] In a second step, the reaction product obtained as described hereinabove is then reacted with an alkylene oxide to form a 1 ,3-dialkyl-ether alkoxylate. Suitable alkylene oxides are any having, in certain non-limiting embodiments, from 2 to 12 carbon atoms. These include, for example, ethylene oxide, propylene oxide, butylene oxide, and the like. In certain embodiments, ethylene oxide may be selected. In other non-limiting embodiments, propylene oxide may be selected, and in still other non-limiting embodiments, a mixture of ethylene oxide and propylene oxide may be selected. Where a mixture of alkylene oxides is used, the result is a copolymer.

[0018] This second step, to form the 1 ,3-dialkyl-ether alkoxylate, is desirably carried out in the presence of at least one ionic catalyst. In one particularly desirably embodiment, at least two ionic catalysts are used, in sequence, with a cationic catalyst employed during the addition of the first few moles of alkylene oxide, and then an anionic catalyst used during the addition of the desired remainder of the alkylene oxide. Alternatively, a single ionic catalyst, or single type of ionic catalyst (i.e., either cationic or anionic), may be used throughout the second alkoxylation. [0019] Possible selections for a cationic catalyst may include acidic catalysts, i.e., cationic polymerization catalysts, such as those known as Friedel-Crafts type reaction catalysts. Such may include, for example, fluorides and chlorides of boron, aluminum, iron, tin and titanium, and complexes of such halides with ethyl ether. In one embodiment, boron trifluoride may be selected. In another embodiment, trifluoromethane sulfonic acid may be selected. In still other embodiments, sulfuric acid or phosphoric acid may be selected. Combinations of any of the above may also be used.

[0020] Possible selections for an anionic catalyst may include alkaline catalysts, i.e., anionic polymerization catalysts, such as Group 1 A metal hydroxides, for example, potassium hydroxide. Alkali metal alcoholates, for example, of the initial alcohol, or the corresponding alcoholate of the 1 ,3-dialkyloxy-2-propanol made during the first stage of the process, may also be selected. Such catalysts may be made in situ by reacting the neutralized product of the first reaction stage with an alkali metal, alkali metal oxide or hydroxide, or may be obtained as neat compositions. Combinations of anionic catalysts may also be selected. [0021] The proportion of the linear or branched 1 ,3-dialkyl-ether, i.e., the 1 ,3- dialkyloxy-2-propanol, to the alkylene oxide may range as a molar ratio of from about 1 :2 to about 1 :20. In certain non-limiting embodiments this ratio may be from about 1 :3 to about 1 :15, and in other non-limiting embodiments it may range from about 1 :5 to about 1 :12.

[0022] The final linear or branched, alkylene oxide-extended 1 ,3-dialkyloxy-ether alkoxylate may be used in formulations and compositions in any desired amount. However, it is commonly known to those skilled in the art that levels of surfactant in many applications may range from about 0.05 to about 50 weight percent, more frequently from about 0.1 to about 30 weight percent, and in some uses from about 0.5 to about 20 weight percent. Those skilled in the art will be able to determine usage amounts via a combination of general knowledge of the applicable field as well as routine experimentation where needed.

[0023] Compositions of the invention include a wide variety of formulations and products made therefrom. These include, but are not limited to, polyurethanes, epoxies, thermoplastics, paints, coatings, metal products, agricultural products including herbicides and pesticides, oilfield products, pulp and paper products, textiles, water treatment products, flooring products, inks, colorants, pharmaceuticals, cleaning products, personal care products, lubricants, and a combinations of these. In these and other formulations and products, the alkoxylate may contribute a property such as surfactancy, detergency, wetting, re- wetting, foam reduction, latex stabilization, drug delivery capability, emulsification, improved rinsing, plasticization, reactive dilution, rheology modification, improved suspension, pseudoplasticization, thickening, capping capability, curing, impact modification, lubrication, emulsification and micro-emulsification, a combination thereof, or the like.

[0024] Examples of these applications include the alkoxylates' utility as surfactants in general; as reactive diluents in casting, encapsulation, flooring, potting, adhesives, laminates, reinforced plastics, and filament windings; as coatings for electrotechnical applications such as encapsulation of both magnetic and high voltage coils; as wetting agents; as rinse aids; as defoam/low foam agents; as spray cleaning agents; as drug delivery agents; as emulsifiers for herbicides and pesticides; as metal cleaning agents; as suspension aids and emulsifiers for paints and coatings; as mixing enhancers in preparing microheterogeneous mixtures of organic compounds in polar and non-polar carrier fluids for agricultural spread and crop growth agents; as stabilizing agents for latexes; as microemulsifiers for pulp and paper products; and the like. In one non- limiting embodiment, compositions utilizing the alkoxylates may include microemulsions used for organic synthesis, formation of inorganic and organic particles, polymerization, and bio-organic processing and synthesis, as well as combinations thereof. In another non-limiting embodiment, the alkoxylates described herein may serve to dilute higher viscosity epoxy resins based on, for example, bisphenol-A, bisphenol-F, and novolak, as well as other thermoplastic and thermoset polymers such as polyurethanes and acrylics. They may also find use in rheology modification of liquid systems such as inks, emulsions, paints, and pigment suspensions, where they may be also used to impart pseudoplasticity or thixotropic flow behavior. In these and other uses the alkoxylates may offer good and, in some cases, excellent performance, as well as relatively low cost. [0025] It is commonly known to those skilled in the art that levels of surfactant in such applications, and formulations therefor, may range from about 0.05 to about 50 weight percent, more frequently from about 0.1 to about 30 weight percent, and in some uses, from about 0.5 to about 20 weight percent. Those skilled in the art will be able to determine usage amounts via a combination of general knowledge of the applicable field, as well as routine experimentation where needed. [0026] The description hereinabove is intended to be general and is not intended to be inclusive of all possible embodiments of the invention. Similarly, the examples hereinbelow are provided to be illustrative only and are not intended to define or limit the invention in any way. Furthermore, those skilled in the art will be fully aware that other embodiments within the scope of the claims will be apparent, from consideration of the specification and/or practice of the invention as disclosed herein. Such other embodiments may include selections of specific alcohols, catalysts, and combinations of such compounds; proportions of such compounds; mixing and reaction conditions, vessels, and protocols; performance and selectivity; additional applications of the linear or branched, alkylene-oxide extended dialkyl- ether alkoxylates not specifically addressed herein; and the like; and those skilled in the art will recognize that such may be varied within the scope of the appended claims hereto.

EXAMPLES Example 1

A. Preparation of a branched 1 ,3-dialkyloxy-2-propanol

[0027] To a 1 -liter bottle in a film hood, without rigorous exclusion of air or moisture, is added about 24.4 g of tetrabutylammonium bromide, about 66.4 g of sodium hydroxide that has been ground to a fine powder, and about 305.7 g of 2- methyl-1 -heptanol. The bottle is shaken to dissolve the tetrabutylammonium bromide. About 13.1 g of 1 -chloro-2,3-epoxypropane is then added and the bottle is shaken to mix the suspension.

[0028] After one hour about 13.1 g of 1 -chloro-2,3-epoxypropane is added again and the bottle is shaken to mix the suspension. Three more additions of 1 -chloro- 2,3-epoxypropane are carried out at one-hour intervals, for a total of five such additions, totaling 65.4 g of 1 -chloro-2,3-epoxypropane. The reaction is monitored by gas chromatography until all of the 1 -chloro-2,3-epoxypropane is consumed. [0029] The reaction product is then analyzed to contain a proportion of 1 ,3-di-(2- methylheptyloxy)-2-propanol.

[0030] The reaction described herein is repeated 16 times. The combined batches are then filtered through a coarse sintered glass funnel to remove salt and unreacted sodium hydroxide and the filtrate is washed with deionized water. Light fractions, primarily 2-methyl-1 -heptanol, are removed by stripping on a rotary evaporator with a heating bath set at 9O⁰C, by lowering the pressure at a rate to prevent bumping until a final pressure of about 0.5 mm is reached. The stripped material has a higher proportion of the 1 ,3-di-(2-methylheptyloxy)-2-propanol.

B. Separation of the 1 ,3-dH2-methylheptyloxy)-2-propanol

[0031 ] The stripped material is distilled in a batch distillation apparatus consisting of a 2-liter kettle heated with a heating mantle, magnetic stirring, a thermowell, and a one-piece distilling head/condenser. The distillation is conducted by reducing the pressure to full vacuum pump pressure (0.2 to 0.5 mm) and slowly increasing the mantle temperature. Cuts taken below an overhead temperature of 155⁰C contain light fractions such as 2-methyl-1 -heptanol and 1 -(2-methylheptyloxy)-3-chloro-2- propanol. The 1 ,3-di-(2-methylheptyloxy)-2-propanol is the overhead product when the overhead temperature is from about 138-16O⁰C and the kettle temperature is below 200⁰C.

C. Further separation of the 1 ,3-di-(2-methylheptyloxy)-2-propanol [0032] The initial distillation in part "B" hereinabove results in a product including both 1 ,3-di-(2-methylheptyloxy)-2-propanol and the undesirable contaminant, 1 -(2- methylheptyloxy)-3-chloro-2-propanol. A strong base is added to the distillation product in an attempt to convert the 1 -(2-methylheptyloxy)-3-chloro-2-propanol to 2- methylheptyl glycidyl ether, which is expected to react further to form the high boiling compound. The cuts from the first distillation, contaminated with 1 -(2- methylheptyloxy)-3-chloro-2-propanol, are combined with the remaining stripped material and treated with sodium hydride. The sodium hydride is a 60 percent by weight solution in mineral oil as received from a commercial producer, but the weight of this initial charge, recorded as the weight of the crude 1 ,3-di-(2-methylheptyloxy)- 2-propanol solution, does not include the mineral oil. This initial charge is roughly estimated to be equimolar to the chlorohydrin concentration and results in a reduction of the 1 -(2-methylheptyloxy)-3-chloro-2-propanol concentration. Repeating the sodium hydride treatment reduces the 1 -(2-methylheptyloxy)-3-chloro-2-propanol concentration further. The resulting hydride material is washed with dilute HCI followed by a wash with saturated sodium carbonate.

[0032] The crude washed material is then subjected to another batch distillation as described hereinabove. Cuts are collected when the overhead temperature is from about 138-16O⁰C and are combined to give a relatively high proportion of 1 ,3- di-(2-methylheptyloxy)-2-propanol.

D. Preparation of the branched ether-alkoxylate (ethoxylation of 1 ,3-di-(2- methylheptyloxy)-2-propanol)

[0034] In separate reactions, five samples of the purified 1 ,3-di-(2- methylheptyloxy)-2-propanol are individually reacted with varying molar amounts of ethylene oxide, using potassium hydroxide (KOH), trifluoromethane sulfonic acid (CF₃SO₃H), or boron trifluoride (BF₃) as the catalyst. The molar amounts are 2, 6, 9 and 12, with two samples prepared using 2 moles of ethylene oxide each.

E. Use of the ether-alkoxylate of 1 ,3-dH2-methylheptyloxy)-2-propanol in a latex formulation

[0035] A reactor is charged with 81 .3 parts by weight of water, which already contains 1 weight percent of seed latex. The kettle is heated to about 8O⁰C. and purged with nitrogen. Over a period of about 4 hours, two separate mixtures are fed into the reactor. One mixture consists of about 50 parts by weight of butylacrylate, about 47.5 parts by weight of styrene, about 1 .5 parts by weight of acrylic acid and about 1.0 parts by weight of methacrylic acid. The other mixture consists of about 19.0 parts by weight of water, about 1 .5 parts by weight of ethoxylated-[1 ,3-di-(2- methylheptyloxy)-2-propanol], about 0.1 parts by weight of sodium hydroxide (20 percent by weight) in water, and about 0.7 parts by weight of potassium persulfate. After addition, the reactor is held at about 8O⁰C for about 30 minutes, and then allowed to cool down to about 3O⁰C. The latex product thereby formed contains about 44.4 percent solids, and the monomer conversion is about 99 percent of theoretical. This latex product is useful as component for a paint formulation, an adhesive formulation, or a paper coating formulation. Example 2

[0036] A Draves Wetting Test is carried out as a test of performance of the wetting capability of aqueous surfactant solutions representing one embodiment of the inventive compositions. This test involves determining the time required for a cotton skein to sink when immersed in the aqueous surfactant solutions of various concentrations. The data represent the concentration required to wet the skein in 20 seconds. This information is useful for evaluating, for example, hard-surface cleaners where rapid wetting and penetration is critical. The results are shown in Table 1 , wherein is apparent that very low concentrations of the surfactant produce acceptable wetting capability, and that longer chain alkylene oxide moieties appear to further increase the wetting capability.

Table 1

Claims

WHAT IS CLAIMED IS:

1. A composition comprising a linear or branched alkylene oxide-extended 1 ,3-dialkyloxy-2-propanol alkoxylate.

2. The composition of claim 1 wherein the alkoxylate contains an alkyloxy moiety that is linear.

3. The composition of claim 1 wherein the alkoxylate contains an alkyloxy moiety that is branched.

4. The composition of claim 1 wherein the alkoxylate includes from 2 to 12 repeating alkylene oxide units.

5. The composition of claim 1 wherein the alkoxylate contains an alkyloxy moiety having from 3 to 28 carbon atoms.

6. The composition of claim 5 further comprising at least one heteroatom selected from the group consisting of elements Group IVA, VA, VIA and VIIA, and combinations thereof.

7. The composition of claim 1 wherein the alkoxylate contributes to the composition a property selected from the group consisting of surfactancy, detergency, wetting, re-wetting, foam reduction, latex stabilization, drug delivery capability, emulsification and micro-emulsification, improved rinsing, plasticization, reactive dilution, rheology modification, improved suspension, pseudoplasticization, thickening, capping capability, curing, impact modification, lubrication, and combinations thereof.

9. The composition of claim 1 wherein the composition is a formulation selected from the group consisting of a polyurethane formulation, an epoxy formulation, a paint formulation, a coating formulation, a metal working formulation, an agricultural formulation, an oilfield formulation, a pulp and paper processing formulation, a textile formulation, a water treatment formulation, a flooring formulation, an ink formulation, a colorant formulation, a pharmaceutical formulation, a cleaning formulation, an agricultural crop formulation, a lubricant formulation, a personal care product formulation, a latex formulation, an emulsion polymerization formulation, a suspension polymerization formulation, an emulsification process formulation, a suspension process formulation, a dispersion process formulation, and combinations thereof.

10. The method of claim 1 wherein the composition is a product selected from the group consisting of a polyurethane, an epoxy, a thermoplastic, a paint, a coating, a metal product, an agricultural product, an oilfield product, a pulp or paper product, a textile, a water treatment product, a flooring, an ink, a colorant, a pharmaceutical, a cleaning product, a personal care product, a lubricant, and combinations thereof

1 1 . A method of preparing a composition comprising incorporating in a composition a linear or branched, alkylene oxide-extended 1 ,3-dialkyloxy-2-propanol alkoxylate.

12. The method of claim 1 1 wherein the alkoxylate contains an alkyloxy moiety that is linear.

13. The method of claim 1 1 wherein the alkoxylate contains an alkyloxy moiety that is branched.

14. The method of claim 1 1 wherein the alkoxylate includes from 2 to 12 repeating alkylene oxide units.

15. The method of claim 1 1 wherein the alkoxylate contains an alkyloxy moiety having from 3 to 28 carbon atoms.

16. The method of claim 15 wherein the alkyloxy moiety contains at least one heteroatom selected from the group consisting of elements of Groups IVA, VA, VIA and VIIA, and combinations thereof.

17. The method of claim 1 1 wherein the alkoxylate is used in an amount from about 0.05 to about 50 percent by weight.

18. The method of claim 17 wherein the alkoxylate is used in an amount from about 0.1 to about 30 percent by weight.

19. The method of claim 18 wherein the alkoxylate is used in an amount from about 0.5 to about 20 percent by weight.

20. The method of claim 1 1 wherein the composition is a formulation selected from the group consisting of a polyurethane formulation, an epoxy formulation, a paint formulation, a coating formulation, a metal working formulation, an agricultural formulation, an oilfield formulation, a pulp and paper processing formulation, a textile formulation, a water treatment formulation, a flooring formulation, an ink formulation, a colorant formulation, a pharmaceutical formulation, a cleaning formulation, an agricultural crop formulation, a lubricant formulation, a personal care product formulation, a latex formulation, an emulsion polymerization formulation, a suspension polymerization formulation, an emulsification process formulation, a suspension process formulation, a dispersion process formulation, and combinations thereof.

21 . The method of claim 1 1 wherein the composition is a product selected from the group consisting of a polyurethane, an epoxy, a thermoplastic, a paint, a coating, a metal product, an agricultural product, an oilfield product, a pulp or paper product, a textile, a water treatment product, a flooring, an ink, a colorant, a pharmaceutical, a cleaning product, a personal care product, a lubricant, and combinations thereof