Alkyl glycidyl ether-capped polyamine foam control agents

Details Alkyl glycidyl ether-capped polyamine foam control agents Alkyl glycidyl ether-capped polyamine foam control agents

2001-07-20

2003-12-02

Metzmaier, Daniel S. (Department: 1712)

Colloid systems and wetting agents; subcombinations thereof; pro

Compositions containing an agent for breaking ; processes of...

Continuous liquid phase colloid system and discontinuous gas...

C208S206000, C208S207000, C504S358000, C510S499000, C162S158000, C008S551000, C524S244000, C524S245000

Reexamination Certificate

active

06656977

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to the use of the reaction products of polyamines and alkyl glycidyl ethers as foam control agents.
BACKGROUND OF THE INVENTION
Foam control or elimination in many waterborne applications and industrial processes is critical for obtaining optimal performance in application and high process efficiency. The importance of foam control and elimination in applications such as waterborne coatings, inks, adhesives, and agricultural formulations and in industrial processes such as oil well pumping, petroleum gas scrubbing, cleansing and disinfecting, food processing, pulp and paper processing, fermentation, metal treatment, polymer and chemical synthesis, waste-water treatment and textile dying and finishing is well-appreciated in the art.
Foam control agents are widely used in polymer production and processing, as foam can lead to reduced production capacity, efficiency and equipment problems. In particular, severe foaming problems commonly result upon stripping unreacted monomers from the polymer product.
Undesirable foam can lead to inefficient mixing, poor productivity, reduced vessel capacity and equipment failure in many common industrial processes. For instance, foaming in refinery processes such as drilling, production, stimulation, distillation, extraction, gas and liquid scrubbing and other operations leads to a number of operating difficulties and significant economic consequences. In acid gas sweetening, gases such as carbon dioxide and hydrogen sulfide are removed via scrubbing with an aqueous amine solution. Problematic foam can occur during both the scrubbing or regeneration steps in this process.
Defoamers and antifoams are additives that are used to reduce or eliminate problematic foam. An “antifoam” refers to a long-acting agent which prevents foam formation. A “defoamer” is a material that yields rapid knock-down of existing foam. Herein, the term “foam control agent” is used to refer to additives that eliminate and/or control foam since many applications and processes require both foam prevention and reduction or elimination.
In many applications it is desired that foam control agents exhibit positive ancillary surface properties, such as wetting, dispersion, emulsification, solubilization, flow and leveling. For example, defoamers and antifoams that act as wetting agents will greatly reduce surface defects in coatings, inks, adhesives and agricultural formulations. In addition, such multi-functional materials will allow for the reduction or elimination of wetting agents in a waterborne composition, thereby reducing the total amount of additives. The ability of a material to act as a wetting agent in waterborne formulations is assessed by its ability to reduce the surface tension of water. Equilibrium surface tension performance is important when a system is at rest. However, the ability to reduce surface tension under dynamic conditions is of great importance in applications where high surface creation rates are utilized. Such applications include the spraying, rolling and brushing of coatings, adhesives or agricultural formulations, or high-speed gravure or ink-jet printing. Dynamic surface tension is a fundamental quantity which provides a measure of the ability of a substance to reduce surface tension and provide wetting under high-speed application conditions. Also, it is under such high speed application conditions where the entrainment of air and the creation of foam is a problem.
Adducts prepared by the reaction of polyamines with alkyl glycidyl ethers (epoxies) may be found in the literature. Such amines have been utilized in a variety of applications. Depending upon the polyamine, five or more epoxy reagents may be used to form a completely adducted amine. The majority of examples in the literature contain amines which are not fully adducted.
U.S. Pat. No. 4,650,000 discloses adducts prepared by the reaction of polyamines with C6-C18 alkyl glycidyl ethers have been shown to be effective surfactants for the formation of microemulsions containing a hydrocarbon oil and aqueous acid solutions used to treat subterranean rock formations surrounding oil and gas wells. In this case, the amine surfactants were all utilized in the microemulsions as cationic quaternary ammonium salts.
U.S. Pat. No. 4,797,202 discloses N-(hydrocarbyl)-&agr;,&ohgr;-alkanediamines as collectors for the recovery of minerals from mineral ores by froth flotation. In particular, the 1:1 adduct of diethylenetriamine and 2-ethylhexyl glycidyl ether was shown to be effective for copper recovery in the froth flotation of copper sulfide.
CH 313 159 discloses a process for the preparation of stable dye and stripper baths containing positively charged amine additives. The baths contain 1:1 adducts of diamines and polyamines and C8 and greater alkylglycidyl ethers and the corresponding alkylated amines formed by subsequent reactions with ethylene oxide, dimethyl sulfate, chloroacetic acid and other reagents.
U.S. Pat. No. 4,311,618 discloses the use of a water soluble cleanser concentrate comprising an ionic surfactant, a non-ionic surfactant, an amphoteric dissociating agent and an organic aprotic solvent. The hydrochloride salt of the 1:2 adduct of diethylenetriamine and 2-ethylhexyl glycidyl ether is shown in Example 5.
JP52018047 discloses adducts prepared by the reaction of polyamines and up to 3 C6-C16 alkyl glycidyl ethers have been utilized as bactericides.
JP 450119973 discloses similar compounds which also contain carboxylate groups have been shown to be effective bactericidal surfactants.
U.S. Pat. No. 3,931,430 discloses the use of reaction products of diamines and polyamines and C4-C16 glycidyl esters and ethers as desensitizers for pressure-sensitive recording sheets. These desensitizers must be soluble in an oil vehicle used to make non-aqueous ink for offset printing.
SUMMARY OF THE INVENTION
The present invention relates to the use of the reaction products of polyamines and alkyl glycidyl ethers of the formula:
where
n and m are 2 or 3,
x is 1-6,
R′ is a C4 to C22 alkyl group,
for controlling, i.e., reducing, preventing or eliminating, foam in waterborne compositions and industrial processes that otherwise manifest foaming. According to this invention, the foam control agent may be prepared from any C4 to C22 alkyl glycidyl ether and polyamine consistent with the above formula. These foam control agents are low color, low odor, 100% active materials.
Not all alkyl glycidyl ether-capped polyamines are capable of reducing or eliminating foam and certain adducts in fact add problematic foam to waterborne systems. Therefore, the correct combination of polyamine and alkyl glycidyl ether group and an optimum degree of adduction is essential for the reduction and/or elimination of foam. Thus, suitable alkyl glycidyl ether-capped polyamines are those that generate an initial foam height at least 30% less than a 0.1 wt % aqueous solution of dioctyl sodium sulfosuccinate (DOSS) when added at 0.1 wt % to the aqueous DOSS solution, as measured according to ASTM D 1173-53 at ambient temperature.
By “water-based”, “waterborne”, “aqueous” or “aqueous medium”, we mean, for purposes of this invention, a solvent or liquid dispersing medium which comprises water, preferably at least 90 wt %, and most preferably at least 95 wt %, water. Obviously, an all water medium is also included.
As another embodiment of the invention, the foam control agents may be utilized as wetting agents.
There are significant advantages associated with the use of these alkyl glycidyl ether-capped polyamines as foam control agents in water-based compositions and processes and these advantages include one or more of the following:
foam control agents which have low odor and color;
foam control agents which comprise 100% active ingredient and thus do not require carrier fluids, solvents or other additives and exhibit improved shelf stability;
waterborne coatings and inks which have low volatile organic content, thus making these formulations environmentally favorable;
foam

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