Method Of Making An Alkoxylated Polyethylenimine Product

Abstract

A method of making an alkoxylated polyethyleneimine (APEI) product having reduced discoloration includes treating a composition including a component selected from the group of polyethyleneimine (PEI), alkoxylated polyethyleneimine (APEI) intermediate, and combinations thereof that is used to make the APEI product. The method of treating the composition includes adding water to the composition in an amount of from 2 to 20 parts by weight, based on the total weight of the composition. The water is stripped from the composition within a relatively low temperature range of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, based on the total weight of the composition, is present in the composition. The aqueous solutions of APEI product thus made have Gardner color values of less than 6.

Description

RELATED APPLICATIONS

This patent application claims priority to and all advantages of U.S. Provisional Patent Application Nos. 60/650,990 and 60/650,914 which, were filed on Feb. 8, 2005.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The subject invention relates to a method of making an alkoxylated polyethyleneimine product. More specifically, the subject invention relates to a method of treating a composition including a component selected from the group of polyethyleneimine, an alkoxylated polyethyleneimine intermediate, and combinations thereof to improve the appearance of the alkoxylated polyethyleneimine product in an aqueous solution.

2. Description of the Related Art

Alkoxylated polyethylenimines (APEIs) are known in the art, as are methods of making APEI products including the APEIs. Among the APEIs, propoxylated polyethylenimines (PPEIs) and ethoxylated polyethylenimines (EPEIs) are most common in commercial applications. The EPEIs are commonly used in consumer products, especially laundry detergents, and generally function as dispersants by chelating cationic particles, such as clay particles, and holding them in solution. The EPEIs hold the particles in suspension until the particles are removed through a rinsing process, thus preventing the particles from re-depositing on the fabric in the laundry.

Current methods of making the APEI products start from a composition including polyethyleneimines (PEIs). A method of making the composition including the PEIs is by reacting ethylenediamine (EDA) and ethylenimine (EI) under acid catalysis, in solvents such as water. An example of a common EI is aziridine, which is a three-member ring having a reactive nitrogen. The EI is polymerized through a ring-opening reaction involving the reactive nitrogen of the aziridine. The reaction is maintained until the amount of unreacted EI falls below a predetermined level. The resulting polyethylenimines (PEIs) in the composition have primary, secondary, and tertiary amine functionalities that are available for further chemical conversion, e.g. alkoxylation with alkylene oxides such as ethylene oxide to form APEI. The ethoxylation of PEIs is described in Houben-Weyl, Methoden der organischen Chemie, 4. Ed., Vol. 14/2, p. 440 ff. (1963) and Vol. E 20, p. 1367 f. (1987).

One of the problems with current APEI products is discoloration in aqueous solutions including the APEI products. Incorporation of APEI products that cause significant discoloration in consumer products is undesirable since it can distort the desired color and appearance of the consumer products, which in turn can diminish consumer appeal. The discoloration of the aqueous solutions including the APEI products is typically measured using a UV-VIS spectrophotometer or by comparing the aqueous solutions including the APEI products to color standards such as Gardner color standards. In such measurements, the APEI products are diluted with solvents like water or alcohols, e.g. methanol or ethanol, THF, DMF or aqueous acids, to concentrations that are practical to determine coloristic properties. These concentrations can range from 5 to 30% by weight for the active polymer. Measurements of the coloristic properties are conducted at various wavelengths that can range from 350 to 800 nm and are carried out in one or two channel UV/Vis-spectrophotometers.

It is known in the art that impurities present in compositions including the PEI produce significant discoloration and high color in the aqueous solutions of APEI product made from them. However, there is no way of knowing from the appearance of the composition including the PEI whether aqueous solutions of APEI product with sufficiently low color can be made, since the compositions including the PEI are generally of low color, in the range of 1 to 3 by the Gardner standard.

Hydrides, such as sodium or potassium borohydride, are thought to improve the color of the aqueous solutions of APEI product and are often used in the manufacturing process. The aqueous solutions of APEI product manufactured following the conventional processes are highly colored and the formation of color bodies is unpredictable. For the aqueous solutions of APEI product manufactured following the conventional processes, Gardner color values are typically above 10 and often in the range of 14-18. Aqueous solutions of APEI product having Gardner color values greater than 10 are considered significantly discolored, and their utility in consumer products is inhibited. It is desirable to obtain aqueous solutions of APEI product with Gardner color values less than 6, which are presently unattainable through the use of the hydride or other measures alone.

U.S. Pat. No. 6,451,961 to Suzuki et al. suggests a method of treating compositions including PEI that have been produced from EI, which in turn was manufactured via a dehydration reaction of monoethanolamine in the presence of a catalyst. The method includes adding water to the PEI in an amount of from 1 to 95 parts water, based on the weight of the PEI to form the composition including the PEI. At least 15 percent of the added water is then distilled out of the composition at a temperature of from 212 to 392° F. and at reduced pressure to remove volatile impurities such as excess ethanolamine and other low-boiling residual components such as ammonia, lower alkyl amines, and aldehydes. According to the '961 patent, those volatile impurities cause offensive smell and a reduction in stability of the polyethyleneimines when present.

While it is obvious that water and other volatile compounds that are not chemically bound to the PEIs will be more quickly removed from the composition at higher temperatures, there could be factors that control the outcome of alkoxylation of the PEIs other than the removal of volatile impurities. Specific factors that may control the outcome of alkoxylation include the reaction of products of carbonyl compounds with the nitrogen functionality of the PEIs, subsequent removal of those products through distillation, and possible structural changes of the PEIs due to the removal of cross-linking building blocks. Such factors are not accounted for by the treatment method of the '961 patent. Furthermore, ethanolamine and ammonia, which are removed in the treatment method of the '961 patent, are not considered harmful in the sense of causing discoloration. More specifically, the functionalities of the ethanolamine and ammonia are also found in compositions including the PEI and/or the APEI product. Ethanolamine and ammonia are known to readily participate in the alkoxylation process, leading to colorless APEI products. Hence many of the impurities removed in the '961 patent need not be removed to reduce discoloration of the aqueous solutions of APEI product, and the drawbacks of the presence of the ethanolamine and ammonia are not experienced by the consumer since the ethanolamine and ammonia are consumed during the production of the APEI product, thus yielding minute amounts of high molecular weight products in the APEI product that are chemically similar to the APEI. Finally, the presence of water in the composition including the PEI negatively affects alkoxylation beyond the reaction of one equivalent mole of alkylene oxide for each functionality of the PEI. As a result, the presence of excessive quantities of water during alkoxylation to produce the APEI product, which has more than one moles of alkylene oxide for each functionality of the PEI, is undesirable.

There remains an opportunity to provide a method of making APEI products that consistently exhibit improved color properties in aqueous solutions of the APEI products, namely Gardner color values of less than 6, without affecting the chemical structure or properties of the APEI products.

SUMMARY OF THE INVENTION AND ADVANTAGES

The subject invention provides a method of treating a composition and a method of making an alkoxylated polyethyleneimine (APEI) product. The composition includes impurities. The composition also includes a component selected from the group of polyethyleneimine (PEI), alkoxylated polyethyleneimine (APEI) intermediate, and combinations thereof. The method of treating the composition includes the step of adding water to the composition. The water and at least a portion of the impurities are stripped from the composition at a temperature of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, based on the total weight of the composition, is present in the composition. The method of making the APEI product further includes the step of alkoxylating the component in the composition to make the APEI product.

By stripping the water and the impurities from the composition within the temperature range of from 158 to 203° F., and by stripping until less than 0.2 parts by weight water, based on the total weight of the composition, is present in the composition, a sufficient amount of certain impurities that cause high discoloration in the APEI products are removed from the composition to improve color properties in the APEI products made from the composition, while retaining other impurities in the composition that are not harmful in the sense of causing discoloration. Furthermore, the impurities are removed without causing structural changes in the PEI and/or APEI intermediate in the composition.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a flow chart of one method of making the alkoxylated polyethyleneimine product of the present invention.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Referring to FIG. 1, a method of making an alkoxylated polyethyleneimine (APEI) product may include the step of making a composition including polyethyleneimine (PEI). The PEI is made by starting with a di- or polyamine such as ethylene diamine (EDA), ethylenimine (EI) such as aziridine, water, and an acid catalyst. Acid catalysts such as sulfuric acid, carbonic acid, or any lower carboxylic acid catalyst, e.g., C1 to C6, may be used for the production of the composition including the PEI. Specific examples of suitable acid catalysts include sulfuric, formic, and carbonic acids. The PEIs in the composition are available at a range of molecular weights and have a number average molecular weight of at least 150, more preferably from 600 to 30,000. An example of a composition including PEI that is one formed from carbon dioxide catalysis, in the presence of water, in which the PEI has a number average molecular weight of about 600.

The catalysts used to make the PEI in the composition form adducts with the PEI. As is known in the art, conjugate bases, i.e., sulfate, formate, or carbonate ions, depending on which catalyst is used, and the adducts those bases form with the PEI, exhibit different chemical characteristics when those adducts are further processed.

The resulting PEI in the composition has primary and secondary tertiary amine functionalities that are available for further alkoxylation with alkylene oxides, such as ethylene oxide or propylene oxide, to make APEI products such as ethoxylated polyethyleneimines (EPEIs), propoxylated polyethylenimines (PPEIs), respectively. The ethoxylation of PEIs is described in Houben-Weyl, Methoden der organischen Chemie, 4. Ed., Vol. 14/2, p. 440 ff. (1963) and Vol. E 20, p. 1367 f. (1987), both of which are hereby incorporated by reference.

A ratio of primary, secondary and tertiary amine functionalities in the PEI can be determined via an established NMR-methodology. Table 1 summarizes data from recent analyses of PEI made under acid catalysis and having a number average molecular weight of about 600:

TABLE 1
	Primary amine	Secondary amine	Tertiary amine
Sample	functionalities	functionalities	functionalities
PEI, Mn = 600	49% of total	25% of total	26% of total
	amine groups	amine groups	amine groups
	(13.3 g/100 g)	(6.8 g/100 g)	(7.2 g/100 g)

The determination of water content of the composition including the PEI is important because the composition including a component selected from the group of PEI, APEI intermediate, and combinations thereof is subjected to a method of treating by adding more water to remove impurities in the composition that cause discoloration of the APEI product made from the composition. The composition may be treated at any time prior to alkoxylation to make the APEI product under catalysis other than by water. For example, the composition including the component selected from the group of PEI, APEI intermediate, and combinations thereof may be treated at the site of production of the composition or at the site of alkoxylation of the PEI in the composition. Resulting aqueous solutions of the APEI product exhibit high transmission, i.e., reduced discoloration.

In one embodiment, the method of treating the composition includes adding water to the composition including the PEI. The water may be added to the composition including the PEI in an amount of from 2 to 20 parts by weight, based on the total weight of the composition. Alternatively, the composition may already include water in the amount of from 2 to 20 parts by weight such that additional water need not be added. The composition including the PEI and water is heated to a relatively low temperature of from 158 to 203° F. It is to be appreciated, however, that the water may be added to the composition including the PEI after the composition has been heated into the above temperature range. Additionally, the composition including the PEI and water is typically subjected to a pressure of from 0.1 to 250 mm Hg to effectively create a vacuum. It is desirable to achieve a low water content in the composition including the PEI. As such, the water and at least a portion of the impurities are stripped from the composition by maintaining the composition within the above temperature and pressure ranges until the less than or equal to 0.2 parts by weight, typically less than or equal to 0.1 parts by weight of water, based on the total weight of the composition, is present in the composition. A non-condensable gas sparge may also be used, and the composition including the PEI and water may be subjected to agitation to aid in stripping the water from the composition. The non-condensable gas may be selected from the group of, but is not limited to, nitrogen, argon, and combinations thereof. Stripping water can remove at least a portion of the impurities that, during the alkoxylation of the PEI in the composition, will lead to highly colored aqueous solutions of the APEI product. The step of stripping the water from the composition concomitantly removes at least a portion of the impurities that cause discoloration.

The stripping step may take up to 40 hours depending on the initial amount of water added to the composition including the PEI, the pressure, and the use of the sparge by a non-condensable gas.

It was found that the main cause leading to discoloration of the aqueous solutions of the APEI product is linked to the impurities in the composition including the PEI. Although it was hypothesized in the prior art that aldehydes were the main cause of discoloration, experimentation disproved the link between aldehydes and discoloration of the aqueous solutions of the APEI product. The addition of water to the composition including the PEI, coupled with stripping the water and at least a portion of the impurities from the composition at the relatively low temperature of from 158 to 203° F. and pressure of from 0.1 to 250 mm Hg, removes at least a portion of the impurities in the composition that are most problematic in terms of causing discoloration, while typically retaining at least a portion of select impurities in the composition that do not cause discoloration of the aqueous solutions of the APEI product. Such select impurities include ethanolamine and ammonia, which participate in alkoxylation of the PEI in the composition and contain functionalities that are also present in the PEI or the APEI product. Furthermore, the relatively low temperature ensures that more PEI will be retained in the composition, as compared to prior art processes that use higher temperatures for removing the impurities. As a result of treating the composition, aqueous solutions of APEI product made from the composition that has been thus treated are visually considerably lighter and have Gardner color values, as measured in accordance with ASTM D 1544-04, of less than 6, typically from 2 to 4. Similar Gardner color values are also achieved through another method, specifically a method of treating a composition including an adduct of a conjugate base and polyethyleneimine, a component selected from the group of polyethyleneimine, alkoxylated polyethyleneimine intermediate, and combinations thereof, and, optionally, water, as set forth in PCT Application No. ______ entitled “Method of Making an Alkoxylated Polyethyleneimine”, and filed on even date herewith, the disclosure of which is hereby incorporated by reference in its entirety.

In one embodiment, the composition including the PEI and the APEI product may be made at the same facility. Due to spatial constraints and the shear volume of APEI product produced from the composition including the PEI, the composition including the PEI may be produced at one facility and shipped to other facilities, where logistics may allow for more efficient delivery of the APEI product. Alternatively, PEI may be partially alkoxylated with alkylene oxide, in an amount less than a full charge of the alkylene oxide required to make the APEI product, to form the composition including the APEI intermediate to cut down on production inefficiencies. Typically, the APEI intermediate has about 1 alkylene oxide molecule for each functionality of the PEI.

In another embodiment of the present invention, the composition including the APEI intermediate is subjected to the method of treating the composition. Typically, the composition is treated prior to the addition of hydroxide and subsequent alkoxylation to make the APEI product. More specifically, water is added to the composition including the APEI intermediate and stripped from the composition at the temperature of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, typically less than or equal to 0.1 parts by weight of water, based on the total weight of the composition including the APEI intermediate, is present in the composition.

The presence of water, after the composition including the APEI intermediate is formed from the PEI, is undesirable because side reactions take place between the water and the additional alkylene oxide that is added to the composition including the APEI intermediate to make the APEI product. Thus, any water that is added to the composition must be stripped at some time before the composition including the APEI intermediate is alkoxylated to make the APEI product under base catalysis in order to avoid formation of unwanted impurities, such as polyethylene glycol.

A typical PEI used in the method of the present invention has an average functionality of about 14. That is, on average, 14 functional groups (N—H functionalities) are present on each PEI molecule. To form the APEI product by way of the composition including the APEI intermediate, the PEI is partially alkoxylated with only a portion of the total alkylene oxide to be used, thus resulting in the composition including the APEI intermediate. Then, the APEI intermediate in the composition is alkoxylated with the rest of the alkylene oxide under base catalysis to effectively form the APEI product. To form the APEI product, the PEI or APEI intermediate in the composition is alkoxylated with a total of from 5 to 40 alkylene oxide molecules for each functionality of the PEI. Preferably, the PEI or APEI intermediate in the composition is alkoxylated with from 10 to 30, more preferably about 20, alkylene oxide molecules for each functionality of the PEI, to make the APEI product. Since the PEI has about 14 functionalities, the APEI product has from 70 to 560 moles of alkylene oxide for each mole of PEI.

A borohydride may be added to the composition including the component selected from the group of the PEI, the APEI intermediate and combinations thereof. The borohydride may be selected from the group of potassium borohydride (KBH₄), sodium borohydride, and combinations thereof. Typically, the borohydride is added before alkoxylating the PEI in the composition to form the APEI intermediate or APEI product. The borohydride is typically present in an amount of from 0.05 to 0.5 parts by weight based on the total weight of the composition and reduces aldehydes or other undesirable compounds still present in the composition. A hydroxide selected from the group of potassium hydroxide, sodium hydroxide, and combinations thereof may also be added to the composition at this point to catalyze the alkoxylation of the PEI with the alkylene oxide, provided that the PEI is first subjected to the above method of treatment. The composition including the KBH₄ is then heated to a temperature of from 160 to 200° F. for up to one hour, water is added, and alkylene oxide is charged at higher temperatures as described in Houben-Weyl.

The following examples illustrate compositions and Gardner color values that may be obtained for aqueous solutions of APEI product produced using various components and methods outlined above.

Example 1

500 g of PEI-600 (PEI of 600 mol. Wt, 14 functionality) and 20.3 g of water are added to a clean and dry nitrogen purged autoclave to form a composition. The composition is heated to 170-180° F. with agitation. While heating, the autoclave is evacuated to 3.7 mm Hg. A nitrogen sparge through a dip tube aids mass transfer. This operation is continued until less than or equal to 0.2 parts by weight water, based on the total weight of the composition, is present in the composition. Potassium borohydride is added and the composition is agitated for 2 hours at 170-180° F. After cooling to <140° F., the vacuum is relieved and 90 g of water added. After agitating at 122-140° F. for 30 minutes, the composition is heated to 266° F. and the autoclave inertized with 34 psig nitrogen.

The PEI in the composition is converted to PEI-20 EO, i.e., EPEI product, having 20 moles EO at each available site. More specifically, the composition, including 500 g of PEI along with the water and potassium borohydride, is added to a clean, dry and nitrogen purged autoclave along with 18 grams of 45% potassium hydroxide. The composition is heated to 284-300° F. and subjected to agitation and vacuum until no more water distills off. The vacuum is released, the autoclave is padded with 34 psig nitrogen for safety reasons, and 10.3 kg of ethylene oxide are charged at 284-300° F. while keeping the composition inerted with 34 psig nitrogen. After all ethylene oxide is in the autoclave, the composition is reacted out at 284-300° F. to constant pressure to make the EPEI product, cooled to below 80° C., water is added to obtain an aqueous solution including from 70 to 90 parts by weight (or any other desired concentration) of the EPEI product, based on the total weight of the aqueous solution, and the aqueous solution is discharged. The aqueous solution of the EPEI product in water is lighter in color than the Comparative Examples, with a Gardner color value of 3.0.

Example 2

49.7 kg of PEI-600 (PEI of 600 mol. Wt, 14 functionality) and 9.95 kg of water are added to a clean and dry nitrogen purged autoclave to form a composition. The composition is heated to 170-180° F. with agitation. While heating, the autoclave is evacuated to 50 mm Hg. A nitrogen sparge through a dip tube aids mass transfer. This operation is continued until less than or equal to 0.1 parts by weight of water, based on the total weight of the composition, is present in the composition. Potassium borohydride is added and the composition agitated for 3 hours at 170-180° F. After cooling to <140° F., the vacuum is relieved and 6.7 kg of water added. After agitating at 122-140° F. for 45 minutes, the composition is heated to 248-257° F. and the autoclave inertized with 34 psig nitrogen.

The PEI in the composition is converted to PEI-20 EO, i.e., EPEI product, having 20 moles EO at each available site. More specifically, a portion of the composition, including 17.6 kg of PEI along with the water and potassium borohydride, is added to a clean, dry and nitrogen purged autoclave along with 0.69 kg of 45% potassium hydroxide. The composition is heated to 287-300° F. and subjected to agitation and vacuum until no more water distills off. The vacuum is released, the autoclave is padded with 34 psig nitrogen for safety reasons, and 362 kg of ethylene oxide are charged at 287-300° F. while keeping the composition inerted with 34 psig nitrogen. After all ethylene oxide is in the autoclave, the composition is reacted out at 287-300° F. to constant pressure to make the EPEI product, cooled to below 80° C., water is added to obtain an aqueous solution including from 70 to 90 parts by weight (or any other desired concentration) of the EPEI product, based on the total weight of the aqueous solution, and the aqueous solution is discharged. The aqueous solution of the EPEI product in water is lighter in color than the Comparative Examples, with a Gardner color value of 3.0.

Example 3

64.3 kg of PEI-600 (PEI of 600 mol. Wt, 14 functionality) and 12.8 kg of water are added to a clean and dry nitrogen purged autoclave to form a composition. The composition is heated to 170-180° F. with agitation. While heating, the autoclave is evacuated to 50 mm Hg. A nitrogen sparge through a dip tube aids mass transfer. This operation is continued until less than or equal to 0.1 parts by weight of water, based on the total weight of the composition, is present in the composition. Potassium borohydride is added and the composition agitated for 3 hours at 170-180° F. After cooling to <140° F., the vacuum is relieved and 11.7 kg of water added. After agitating at 122-140° F. for 45 minutes, the composition is heated to 248-257° F. and the autoclave inertized with 34 psig nitrogen.

The PEI in the composition is converted to PEI-20 EO, i.e., EPEI product, having 20 moles EO at each available site. More specifically, a portion of the composition, including 17.8 kg of PEI along with the water and potassium borohydride, is added to a clean, dry and nitrogen purged autoclave along with 0.69 kg of 45% potassium hydroxide. The composition is heated to 287-300° F. and subjected to agitation and vacuum until no more water distills off. The vacuum is released, the autoclave is padded with 34 psig nitrogen for safety reasons, and 366 kg of ethylene oxide are charged at 287-300° F. while keeping the composition inerted with 34 psig nitrogen. After all ethylene oxide is in the autoclave, the composition is reacted out at 142-148° C. to constant pressure to make the EPEI product, cooled to below 80° C., water is added to obtain an aqueous solution including from 70 to 90 parts by weight (or any other desired concentration) of the EPEI product, based on the total weight of the aqueous solution, and the aqueous solution is discharged. The aqueous solution of the final EPEI in water is light in color with a Gardner color value of 3.0.

Comparative Example 1

259 g of PEI-600 (PEI of 600 mol. Wt, 14 functionality) are added to a clean and dry nitrogen purged autoclave together with potassium borohydride to form a composition. The composition is heated to 174-185° F. with agitation. While heating, the autoclave is evacuated to 50 mm Hg. A nitrogen sparge through a dip tube aids mass transfer. This operation is continued for 5 minutes, and then the vacuum is released with nitrogen. After cooling to <140° F., 49 g of water are added. After agitating at 122-140° F. for 15 minutes, the composition is heated to 248-257° F. and the autoclave is inertized with 34 psig nitrogen.

The PEI in the composition is converted to PEI-20 EO, i.e., EPEI product, having 20 moles EO at each available site. More specifically, the composition, including 259 g of PEI along with the water and potassium borohydride, is added to a clean, dry and nitrogen purged autoclave along with 18 g of 45% potassium hydroxide. The composition is heated to 287-300° F. and subjected to agitation and vacuum until no more water distills off. The vacuum is released, the autoclave is padded with 34 psig nitrogen for safety reasons, and 5.32 kg of ethylene oxide are charged at 287-300° F. while keeping the composition inerted with 34 psig nitrogen. After all ethylene oxide is in the autoclave, the composition is reacted out at 287-300° F. to constant pressure to make the EPEI product, cooled to below 80° C., water is added to obtain an aqueous solution including from 70 to 90 parts by weight (or any other desired concentration) of the EPEI product, based on the total weight of the aqueous solution, and the aqueous solution is discharged. The aqueous solution of the EPEI product in water has a brownish-yellow color with a Gardner color value of 8.0.

Comparative Example 2

46.9 kg of PEI-600 (PEI of 600 mol. Wt, 14 functionality) are added to a clean and dry nitrogen purged autoclave to form a composition. The composition is heated to 174-185° F. with agitation. While heating, the autoclave is evacuated to 50 mm Hg. A nitrogen sparge through a dip tube aids mass transfer. This operation is continued for 15 minutes, and then the vacuum is released with nitrogen. Potassium borohydride is added and the composition agitated for 2 hours at 176-185° F. After cooling to <140° F., 8.1 kg of water are added. After agitating at 122-140° F. for 15 minutes, the composition is heated to 248-257° F. and the autoclave is inertized with 34 psig nitrogen.

The PEI in the composition is converted to PEI-20 EO, i.e., EPEI product, having 20 moles EO at each available site. More specifically, a portion of the composition, including 21.2 kg of PEI along with the water and potassium borohydride, is added to a clean, dry and nitrogen purged autoclave along with 0.56 kg of 45% potassium hydroxide. The composition is heated to 287-300° F. and subjected to agitation and vacuum until no more water distills off. The vacuum is released, the autoclave is padded with 34 psig nitrogen for safety reasons, and 436 kg of ethylene oxide are charged at 287-300° F. while keeping the composition inerted with 34 psig nitrogen. After all ethylene oxide is in the autoclave, the composition is reacted out at 287-300° F. to constant pressure to make the EPEI product, cooled to below 80° C., water is added to obtain an aqueous solution including from 70 to 90 parts by weight (or any other desired concentration) of the EPEI product, based on the total weight of the aqueous solution, and the aqueous solution is discharged. The aqueous solution of the EPEI product in water has a brownish-yellow color with a Gardner color value of 15.0.

Obviously, many modifications and variations of the present invention are possible in light of the above teachings. The invention may be practiced otherwise than as specifically described within the scope of the appended claims. In addition, the reference numerals in the claims are merely for convenience and are not to be read in any way as limiting.

Claims

1. A method of treating a composition, said method comprising the steps of:

providing the composition including impurities and a component selected from the group of polyethyleneimine, alkoxylated polyethyleneimine intermediate, and combinations thereof;

adding water to the composition; and

stripping the water and at least a portion of the impurities from the composition including the component at a temperature of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, based on the total weight of the composition, is present in the composition.

2. A method as set forth in claim 1 wherein the water is added in an amount of from 2 to 20 parts by weight based on the total weight of the composition.

3. A method as set forth in claim 1 wherein the water is stripped at a pressure of from 0.1 to 250 mm Hg.

4. A method as set forth in claim 1 wherein the water is stripped in the presence of a non-condensable gas sparge.

5. A method as set forth in claim 1 further comprising the step of agitating the composition including the water during the step of stripping the water.

6. A method as set forth in claim 1 further comprising the step of adding a borohydride selected from the group of potassium borohydride, sodium borohydride, and combinations thereof to the composition.

7. A method as set forth in claim 1 wherein the polyethyleneimine in the composition has a number average molecular weight of at least 150.

8. A method as set forth in claim 1 wherein the alkoxylated polyethyleneimine intermediate in the composition has a number average molecular weight of at least 1000.

9. A method as set forth in claim 1 wherein the composition is substantially free of alkoxylated polyethyleneimine intermediate.

10. A method of making an alkoxylated polyethyleneimine product comprising the steps of:

adding water to a composition including impurities and a component selected from the group of polyethyleneimine, alkoxylated polyethyleneimine intermediate, and combinations thereof;

stripping the water and at least a portion of the impurities from the composition including the component at a temperature of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, based on the total weight of the composition, is present in the composition; and

alkoxylating the component in the composition to make the alkoxylated polyethyleneimine product.

11. A method as set forth in claim 10 wherein the water is added in an amount of from 2 to 20 parts by weight based on the total weight of the composition.

12. A method as set forth in claim 10 wherein the water is stripped at a pressure of from 0.1 to 250 mm Hg.

13. A method as set forth in claim 10 wherein the water is stripped in the presence of a non-condensable gas sparge.

14. A method as set forth in claim 10 further comprising the step of agitating the composition including the water during the step of stripping the water.

15. A method as set forth in claim 10 further comprising the step of adding a borohydride to the composition.

16. A method as set forth in claim 10 wherein the polyethyleneimine has a number average molecular weight of at least 150.

17. A method as set forth in claim 10 where the alkoxylated polyethyleneimine intermediate has about 1 mole of alkylene oxide for each functionality of the polyethyleneimine.

18. A method as set forth in claim 10 further comprising the step of adding a hydroxide selected from the group of potassium hydroxide, sodium hydroxide, and combinations thereof to the composition prior to the step of alkoxylating and subsequent to the step of stripping the water.

19. A method as set forth in claim 18 wherein the component in the composition is alkoxylated with from 5 to 40 alkylene oxide molecules for each functionality of the polyethyleneimine to make the alkoxylated polyethyleneimine product.

20. A method as set forth in claim 19 further comprising the step of forming an aqueous solution including from 70 to 90 parts by weight of the alkoxylated polyethyleneimine product based on the total weight of the aqueous solution.

21. A method as set forth in claim 20 wherein the aqueous solution of the alkoxylated polyethyleneimine product has a Gardner color value of less than or equal to 6 as measured in accordance with ASTM D 1544-04.

22. A method as set forth in claim 10 further comprising the step of partially alkoxylating polyethyleneimine with an alkylene oxide to form the composition including the alkoxylated polyethyleneimine intermediate.

23. A method as set forth in claim 22 where the alkoxylated polyethyleneimine intermediate has about 1 alkylene oxide molecule for each functionality of the polyethyleneimine.

24. A method as set forth in claim 22 further comprising the step of adding a hydroxide selected from the group of potassium hydroxide, sodium hydroxide, and combinations thereof to the composition prior to the step of alkoxylating and subsequent to the step of stripping the water.

25. A method as set forth in claim 24 wherein the alkoxylated polyethyleneimine intermediate in the composition is alkoxylated with a balance of the alkylene oxide to obtain from 5 to 40 alkylene oxide molecules for each functionality of the polyethyleneimine to make the alkoxylated polyethyleneimine product.

26. A method as set forth in claim 25 further comprising the step of forming an aqueous solution including from 70 to 90 parts by weight of the alkoxylated polyethyleneimine product based on the total weight of the aqueous solution.

27. A method as set forth in claim 26 wherein the alkoxylated polyethyleneimine product has a Gardner color value of less than or equal to 6 as measured in accordance with ASTM D 1544-04.

28. A method of treating a composition, said method comprising the steps of:

providing the composition including impurities, water, and polyethyleneimine;

optionally, adding water to the composition to attain from 2 to 20 parts by weight water based on the total weight of the composition; and

stripping the water and at least a portion of the impurities from the composition at a temperature of from 158 to 203° F. until less than or equal to 0.2 parts by weight of water, based on the total weight of the composition, is present in the composition.

29. A method as set forth in claim 28 wherein the composition is provided having from 2 to 20 parts by weight of water.

30. A method as set forth in claim 28 wherein the water is stripped at a pressure of from 0.1 to 250 mm Hg.

31. A method as set forth in claim 28 wherein the water is stripped in the presence of a non-condensable gas sparge.

32. A method as set forth in claim 28 further comprising the step of agitating the composition including the water during the step of stripping the water.

33. A method as set forth in claim 28 further comprising the step of adding a borohydride selected from the group of potassium borohydride, sodium borohydride, and combinations thereof to the composition.

34. A method as set forth in claim 28 wherein the polyethyleneimine in the composition has a number average molecular weight of at least 150.