Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
2001-06-14
2002-12-17
Vollano, Jean F. (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
C558S026000, C558S027000
Reexamination Certificate
active
06495595
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a surfactant system for general use in agricultural compositions, including, but not limited to herbicidal, fungicidal and insecticidal formulations comprised of two components: an alkoxylated tristyrylphenol hemi-sulfate ester neutralized to the desired pH with an appropriate amount of an alkoxylated alkyl amine.
BACKGROUND OF THE INVENTION
Alkylphenol ethoxylates (APE's) and their anionic derivatives are surfactants that are well known to industry and have historically been relied upon heavily by agricultural chemical producers. However, formulations containing APEs do not always provide the most desirable combination of design specifications, e.g. product efficacy, working parameters and cost. Traditional non-APE surfactant systems have not been readily adaptable substitutes for APE surfactants. For example, calcium dodecylbenzene sulfonic acid used in conjunction with alkoxylated amines have not been as robust as the APE's and their derivatives due to unacceptable performance in one or more key performance areas, such as emulsion stability, acute toxicity, temporal and thermal stability, chemical and physical stability; solution, suspension or dilution dynamics; shear stress tolerance; viscosity; or lack of compatibility with mixing partners.
Phosphate esters of alcohol ethoxylates, which are non-APE surfactants found in many industrial uses, have long term stability problems due to hydrolytically driven transesterification and saponification reactions involving the mono-ester, di-ester, and free acid components of the surfactant mixture. Sulfated surfactants in flowable formulations are typically prone to hydrolytic decomposition, particularly when the formulations are stored in hot, summer warehouse conditions. Thus, there has been a need for an alternative surfactant system which could be easily made from readily available and cost effective raw materials and would be robust to chemical and physical conditions which might be encountered by the formulated product in its life span.
SUMMARY OF THE INVENTION
Surprisingly, it has now been discovered that certain aromatic acids such as alkoxylated tristyrylphenol hemi-sulfate esters which have been neutralized with alkoxylated amines are suitable as alternative ionic surfactants for general use in agricultural products. Even though ethoxylated tristyrylphenol hemi-sulfate esters fall into the general classification of APE's, the tristyrylphenol group is structurally very different from known or conventional APE surfactants. The surfactants of the instant invention may be in the form of a surfactant compound, or composition containing one or more the surfactant compounds or salts. In one embodiment of the invention, the compositions containing the instant surfactant compounds do not contain or are substantially free of known or conventional APEs. The surfactants of the instant invention are obtained from combining the appropriate alkoxylated tristyrylphenol hemi-sulfate ester with the appropriate alkoxylated amine.
The steric configuration of the tristyrylphenol group protects the surfactant from hydrolytic cleavage typically observed in other known anionic sulfate ester surfactant systems.
DETAILED DESCRIPTION OF THE INVENTION
One aspect of the invention concerns the compounds of Formula (1):
(
H
-
B
)
+
A
−
(1)
wherein A
−
is the conjugate base of the acid H-A, wherein H-A is an alkoxylated tristyrylphenol hemi-sulfate ester; and the (H-B)
+
is the conjugate acid of the base B, wherein B is an alkoxylated amine. A preferred aspect of the invention are the compounds having the formula (H-B)
+
A
−
, where A
−
is the anion of the formula:
wherein each R
1
independently is a straight chain or branched C
2
-C
4
alkylene, n is a number from 1 to 50 inclusive, and wherein (H-B)
+
is the cation of the formula:
wherein R
2
is selected from the group consisting of hydrogen, C
1
-C
24
alkyl and C
2
-C
24
alkenyl-CH
2
-, each R
3
independently is a straight chain or branched C
2
-C
4
alkylene, x is a number from 1 to 50 inclusive and y is a number from 0 to 50 inclusive. “Independently” in the context of the R
3
definition means that R
3
may be selected independently in all respects. Thus, the substituents —(R
3
O)
x
—H and —(R
3
O)
y
—H as a whole may be composed of different R
3
groups, and each of the substituents themselves also may be composed of different R
3
groups.
A more preferred embodiment of the invention are the compounds of formula (1) wherein A
−
is:
wherein n is from about 4 to 25 (preferably 4 to 16, especially 8); and wherein (H-B)
+
is the cation of the formula:
wherein R
2
is selected from the group consisting of n-octadecyl, n-hexadecyl and cis-9-octadecenyl, and x+y is a number from about 2 to 15 (preferably 4 to 9). A feature of the invention is where x+y is 5.
The invention also concerns the compound or salt produced from the process of neutralizing an alkoxylated tristyrylphenol hemi-sulfate ester of formula (2) infra (also referred to as HA) with an alkoxylated amine of formula (3) infra (also herein referred to as B). The ammoniumsulfate compounds or the product from the process of combining an aromatic acid HA with an alkoxylated amine B (to the extent there is a difference) are both features of the instantly disclosed invention. The scope of the invention disclosed herein should not be construed to be limited by any particular chemical theory relating to the complexation, equilibration, reaction or acid-base chemistry of the components used to make the surfactants or other ingredients used to make other ultimately useful formulations such as, pesticide formulations. In this regard, another aspect of the invention is the surfactant composition comprising one or more aromatic acids and one or more alkoxylated amines wherein the constituent components may or may not have interacted chemically so as to result in a change in form of the components. The invention encompasses the static composition of the appropriate components admixed together as well as the chemically integrated surfactant composition comprising at least one aromatic acid and at least one alkoxylated amine. “Static composition” denotes the composition composed of components wherein the components have not substantially changed by virtue of their combination with other composition components. “Chemically integrated composition” means a composition that results from the natural equilibration, complexation, dissociation or other chemical transformation if any that may occur after combination of the components and prior to ultimate use of the surfactant in a pesticide formulation. Therefore, the “chemically integrated composition” of the instant invention by definition encompasses the situation where there is a “static composition” as well as any resultant composition occurring at any point in time between initial creation and ultimate use in the field of products containing the surfactant. In other words, the disclosed invention is not limited to a static composition of chemically unaltered constituent components.
Another aspect of the invention is the surfactant composition produced as a whole from the combination of the aromatic acid HA and the alkoxylated amine base B to the extent it is composed of products other than ammoniumsulfate compounds. Such a composition may contain chemically unaltered starting materials as well as other reaction products or by-products from reaction, equilibration, dissociation or complexation of the components in the composition.
The invention also includes the process for obtaining a surfactant which is useful as a substitute for known or conventional APE's. In addition to the surfactant product or the product-by-process, the process of obtaining or making any of the surfactants is herein disclosed as part of the invention. The invention also includes the method of using the surfactant compounds of formula (1) and compositions thereof as subs
Chow Victor Shui-Chiu
Hopkinson Michael James
Moore Carolyn Estep
Shannon Tammy Tyler
Hamilton Thomas
Syngenta Participations (AG)
Teoli, Jr. William A.
Vollano Jean F.
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