Alkyl glycidyl ether-capped diamine foam controlling agent

Details Alkyl glycidyl ether-capped diamine foam controlling agent Alkyl glycidyl ether-capped diamine foam controlling agent

2002-02-01

2004-06-08

Metzmaier, Daniel S. (Department: 1712)

Compositions

Co, s, negative element, or acid, bindant containing

C564S475000, C564S477000, C524S244000, C106S031430, C106S031970, C504S363000, C423S228000, C423S242700, C516S129000, C516S203000

Reexamination Certificate

active

06746623

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to the use of alkyl glycidyl ether-capped diamines as foam controlling 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 [R. Höfer and coworkers, in B. Elvers, J. F. Rounsaville and G. Schulz, eds.,
Ullmann's Encyclopedia of Industrial Chemistry
, Vol. A11, 5
th
Ed., VCH Publishers, New York, 1988, p. 466-488]. Foam problems can arise during production, processing and application. The importance of foam control and elimination is well-appreciated in applications such as waterborne coatings, inks, adhesives, lubricants, over-print varnishes and agricultural formulations and in industrial processes such as oil well drilling, completion and production, acid gas scrubbing, food processing, pulp and paper processing, fermentation, metal treatment, polymer and chemical synthesis, waste-water treatment and textile dying.
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, completion, production, distillation, extraction, gas and liquid scrubbing and other operations leads to a number of operating difficulties and significant economic consequences. In acid gas sweetening, or scrubbing, 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 [V. E. Lewis and W. F. Minyard,
Antifoaming and Defoaming in Refineries in Foams: Fundamentals and Applications in the Petroleum Industry
, Adv. Chem. Ser., 1994, 242, p 461-483].
Defoamers and antifoams are additives that are used to reduce or eliminate problematic foam. An “antifoam” refers to a long-acting additive which prevents foam formation. A “defoamer” is an additive that yields rapid knock-down of existing foam thereby reducing or eliminating the foam. Herein, the term “foam control agent” is used to refer to additives that prevent and/or control foam since many applications and processes require both foam prevention and reduction or elimination.
Foam control agents act to prevent or eliminate foam by countering foam stabilizing forces and accelerating the rate of foam film drainage. Conventional foam control agents utilized in waterborne systems include silicones, dispersed hydrophobic solids, hydrocarbon fluids and polyalkyleneoxide polymers.
In many applications, 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, over-print varnishes 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, the entrainment of air and the creation of foam is a problem under high-speed application conditions.
In addition to the development of multi-functional foam control agents, there is considerable interest in the industry in foam control agents with improved environmental characteristics. This increased environmental concern has been, in part, due to the poor environmental characteristics of currently used foam control agents and new environmental regulations. Such negative characteristics include poor biodegradation, a potential to bioaccumulate and high aquatic toxicity. Thus, not only is it desirable to obtain foam control agents which provide excellent foam prevention or elimination and dynamic wetting, but it is also highly desirable that such new materials are environmentally-friendly.
Highly effective foam control agents, which contain 100 percent active ingredient, have low color and low odor characteristics, can be used effectively under a wide range of operating conditions and do not adversely affect formulation performance or result in the disruption of downstream processes, are highly desirable. Moreover, there is a need in the industry for antifoaming and defoaming agents that exhibit positive ancillary surface properties, such as wetting, dispersion, emulsification, solubilization, flow and leveling.
Foam control agents are widely used in polymer production and processing since 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 [H. F. Mark, N. M. Bikales, C. G. Overberger, G. Menges and J. I. Kroschwitz, Eds.,
Encyclopedia of Polymer Science and Engineering
, 2
nd
Ed. Vol 2, John Wiley and Sons, New York, 1985, p. 59].
Selection of an appropriate foam control agent is key to the successful production, transfer and application of waterborne coatings, inks and adhesives. Defoamers are required in most waterborne coating formulations since they contain wetting agents, emulsifiers, dispersants and other additives which are capable of stabilizing foam [R. A. Reinhardt et. al.,
Defoamer Selection in Waterborne Coatings
, Journal of Coatings Technology, 1998, 70, 157]. Problematic foam can lead to gloss and color loss, craters, pinholes, fish-eyes, orange peel, crawling, poor recoatability, poor color acceptance, adhesion loss and haze development.
U.S. Pat. No. 4,650,000 discloses that cationic quaternary ammonium salts of the adducts of diamines and C
8
-C
18
alkyl glycidyl ethers are 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.
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 ethylenediamine and butyl glycidyl ether was shown to be effective for copper recovery in the froth flotation of copper sulfide.
CH 313159 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 C
8
and greater alkylglycidyl ethers and the corresponding alkylated amines formed by subsequent reactions with ethylene oxide, dimethyl sulfate, chloroacetic acid and other reagents.
JP 2001-107083 discloses 1:1 adducts of amines and alkyl glycidyl ethers for use in laundry detergent compositions.
JP 450119973 discloses adducts prepared by the reaction of amines and C
6
to C
16
alkyl glycidyl ethers as effective bactericidal surfactants. These compounds all contain carboxylate groups.
JP 200010268 discloses the use of adducts containing ethylenically unsaturated groups in photosensitive pastes. In particular, adducts of diamines and glycidyl methacrylate were used.
U.S. Pat. No. 3,931,430 discloses a method for using the reaction products of diamines and polyamines and C
4
-C
16
glycidyl esters and ethers as desensitizers for pressure-sensitive recording sheets. These desensiti

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