NZ720940A - Antidrift composition - Google Patents
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Abstract
The present invention relates to a solid, water-soluble fast-dissolving antidrift composition comprising a urea-based complex-forming component (i) complexed with at least a portion of an antidrift component (ii), and an adjuvant component (iii) a super-spreader surfactant with all, some, or none of the super-spreader surfactant being complexed with the urea-based complex-forming component (i). This composition alleviates the problems associated with spray drift such as the movement of herbicides or other sprayed agricultural treatment material away from the target area. This composition also alleviates the problems associated with a slow dissolution rate.
Description
ANTIDRIFT COMPOSITION
FIELD OF THE INVENTION
This invention relates to complexes of urea—based complex-forming nds
and ifi agents for controlling the droplet size of aqueous sprays, particularly those intended
for agricultural use.
BACKGROUND OF THE INVENTION
Spray drift, or off-target drift, is an increasingly important n of the
agricultural industry. Spray drift is the movement of herbicides or other sprayed agricultural
treatment material away from the target area resulting in wasted al, possible damage to
nearby crops and plants and/or pollution of local surface water. When agriculmral compositions
are sprayed onto crops, a drop size distribution results. While small drops, lly defined as
less than 150 s, traditionally provide better crop coverage, they are also more prone to
drifting. Large drops, commonly regarded as those with diameters r than 400 microns,
tend to resist drift but are prone to bouncing off crop surfaces resulting in reduced coverage and
effectiveness. The optimum drop size range for minimizing drift and maximizing deposition
effectiveness is generally considered to be 0 microns.
Reducing the amount of small droplets can significantly reduce spray drift. This
is currently being achieved by employing new nozzle technology or through the use of relatively
high molecular weight water-soluble polymers as antidn'fi agents. ift additives include
acrylamide homopolymers and mers, polysaccharides such as guar, guar derivatives and
xanthan gums and polyalkylene oxides such as polyethylene oxides. One problem with these
and other known antidrifi additives is that they are often difficult to dissolve in water. A second
problem is that the larger drops that they produce tend not to adhere well to the target crops.
SUIVIMARY OF THE INVENTION
In accordance with the present ion, a solid, soluble, fast-dissolving
antidrifi composition is provided which comprises a ased x-forming component (i)
complexed with an antidrift component (ii).
The antidrifi composition of this invention when incorporated in an aqueous spray
formulation, e.g., one employed in agriculture, provides drift reduction properties very similar to
those of its non-complexed antidrifi component (ii). However, unlike difficult~to—dissolve non—
complexed ift ent (ii), when antidrift component (ii) is complexed with urea-based
complex forming component (i), the antidritt composition herein greatly decreases the amount of
mixing time required to dissolve its complexed antidrifi component (ii) in the aqueous spray
composition. As a further advantage, when added to an agricultural spray, urea-based complex-
forming component (i) of the autidrift composition provides a source of fertilizer apart fiom and
in addition to any other fertilizer(s) with which the antidrift ition may be combined.
BRIEF DESCRIPTION OF THE DRAWING
Fig. 1 is a schematic illustration of the spray booth apparatus employed herein for
measuring spray drift.
DESCRIPTION OF THE ION
In the specification and claims that follow, certain terms and expressions shall be
understood as having the designated gs.
The singular forms "a", "an" and "the" include the plural unless the t clearly
indicates otherwise.
As used herein, the term "may" indicates a ility of an occurrence within a
set of circumstances; a possession of a specified property, characteristic or function; and/or
qualifies another verb by expressing one or more of an ability, capability, or possibility
associated with the qualified verb. Accordingly, usage of "may" indicates that a modified term is
apparently riate, capable, or suitable for an indicated capacity, function or usage while
taking into account that in some circumstances the modified term may mes not be
appropriate, capable or suitable. For example, in some circumstances an event or capacity can be
expected, while in other circumstances the event or capacity does not or cannot occur, such
distinction being captured by the term "may".
All ranges in the specifications and claims are ive of the endpoints and are
independently combinable. It will be understood that any numerical range recited herein is
intended to include all sub-ranges within that range and any combination of the s
endpoints of such ranges or subranges.
{0011] The term "solid" as it applies to the antidrift composition ofthe invention shall be
understood as including an essentially water~free composition as well as one containing a small
amount of water, e.g., ranging from a ible amount up to 10% by weight water and even
higher, provided the water-containing composition exhibits a solid appearance and when
provided in a particulate form, e. g., powder, granules, pellets, prills, or the like, exhibits some
degree of flowability.
The expression "water—soluble" shall be understood herein to be synonymous with
”water-dispersible”.
The expression "fast-dissolving" shall be understood to refer to that characteristic
property of the antidrift ition of the invention whereby a given quantity of the antidrift
composition in particulate form will achieve te dissolution in an s medium in
significantly less time, e.g., in at least 30%, preferably in at least 50% and more preferably in at
least 70%, less time than an lent amount of a mechanical mixture, i.e., a non-complexed
mixture, ofurea—based complex-forming component (i) and antidrifi component (ii), each of
comparable particulate form, under substantially identical dissolution conditions.
The term "complex" as used herein shall be understood to be synonymous with
"clathrate“, rate complex", "cage compound", "host-guest x“, "inclusion
compound", "inclusion complex", and "adduct" as these terms and expressions are understood in
the art. While the e nature of the antidrifi—containing complex of the invention is not
known with certainty, the x exhibits properties that differ from a simple mechanical
mixture of its urea-based x-forming component (i) and antidrifc ent (ii).
The term "adjuvant" as used herein refers to any optional component that when
incorporated in the antidrifi composition of the invention imparts a functionally useful property
thereto, e.g., dispersing, wetting, spreading, etc., and/or enhances a functionally useful property
already sed in some degree by the antidrift composition.
The term "superspreader" as used herein refers to those adjuvant surfactants that
have the property of "superspreading", or "super-wetting". Superspreadmg/supemetting is the
ability of a drop of a solution of a superspreader surfactant to spread to a diameter that is greater
than the diameter of a drop of distilled water on a hydrophobic surface, and also greater than the
diameter to which a solution ofwater and non-superspreading surfactant spreads on the
hydrophobic surface. In addition to this difference in spread er, the contact angle of a
drop of superspreader surfactant solution on a surface is larger than that of a non-superspreading
surfactant solution on the same surface.
As previously indicated, the antidrift ition of this invention is a solid
water-soluble complex ofurea-based complex—forming component (i), i.e., the "host" of a "host-
guest" complex with ifi component (ii) as the ”guest“ of the "host-guest" compleit. Each of
these components of the antidrifi composition herein, ranges oftheir amounts in the antidrift
composition, general s for the preparation of the antidrift composition and specific
examples illustrating various embodiments of the antidn'fi composition and their application will
now be described.
A. Components of the Antidrift Composition
1. Urea-based Complex-forming Component 1i]
Urea based complex—forming component (i) ofthe antidrifi composition of the
ion can be ed from at least one ofurea and urea tive capable of forming a
complex with antidrift component (ii). Among the urea-based complex—forming urea derivatives
that can be used herein with generally good results are thiourea, urea formaldehyde, urea
hydrate, urea phosphate and urea sulfate (monocarbamide dihydrogen e).
Employing urea and/or any complex~forming urea derivative, ing any of
those entioned, complexed with antidrifi component (ii) has the advantages of rendering
the typically lt-to-dissolve antidrifi ent (ii) more readily dissolved in the intended
aqueous spray composition and where such spray composition is to be used in agriculture,
providing a significant source of fertilizer. Urea phosphate onally provides a source of
phosphate and urea sulfate may additionally function as an herbicide, again, in the case of an
agricultural spray.
2. 'fi Component (ii)
Antidriit component (ii) of the antidritt composition of the invention can be
ed from among any ofthe known antidn'fi agents including, without limitation, ric
antidrift agents such as polysaccharides, acrylamide homopolymers and copolymers and their
salts, e.g., their alkali metal salts, in particular, those of sodium and potassium, their ammonium
salts, their di- and trialkylamine salts, their di- and triallcanolamine salts, and the like,
copolymers of maleic acid and conjugated diene including their salts such as those
aforementioned, polyalkylene oxides such as polyethylene oxide, polypropylene oxide and
poly(ethylene oxide-co~propylene oxide), polyvinylpyrrolidone, and their mixtures. These and
other known types ofpolymeric drift agents are lly of relatively high molecular weight,
e.g., on the order of from 10,000 to 50,000,000, and preferably from 0 to 25,000,000,
weight average molecular weight.
Specific examples of useful ccharide antidrift agents include guar, guar
derivatives such as hydroxylpropyl guar (HPG), carboxymethyl ypropyl guar (CMHPG),
xanthan gum, and mixtures thereof.
Specific examples of acrylamide polymers e rylamide homopolymers
and polyacrylamide copolymers and their alkali metal salts such as poly(acrylamide-co-acrylic
acid), poly(acrylarnide-co-acrylic acid, Na salt), polyacrylarnidoalkylsulfonic acid salts, and
mixtures thereof.
Among the useful polyalkylene oxides are the polyethylene oxides and mixtures
thereof.
3. Optional Adj uvant Component (iii)
The antidrift composition of the invention can optionally contain one or more
adjuvant components (iii) known for incorporation in s agricultural sprays. One or more
of these optional adjuvant components (iii) may be d with urea-based complex-forming
component (i) and/or antidrift component (ii) prior to forming the complex resulting in the
antidriit composition of the invention thus offering the possibility that depending on its identity,
some or all of a particular adjuvant component (iii) may also be complexed by urea-based
complex-forming component (i). In addition to or in lieu of the foregoing, one or more optional
adjuvant components (iii) may be admixed with the antidn'it composition once the latter is
formed in which case the resulting composition will constitute a physical mixture of the antidrifi
composition and nt component(s) (iii). Where an optional adjuvant component (iii) is a
liquid, the nature and amount of the liquid incorporated in the antidn'ft composition will be such
that the resulting composition continues to appear as a solid.
Among the many kinds of optional adjuvant components (iii) that can be included
in the antidrift composition of the ion are superspreader tants of both the
organosilicon and ganosilicon types and non—superspreading surfactants of both these
types, one or more ofwhich may be complexed in whole or in part with urea-based complex-
forrning component (i), and antifoam additives, anticaking/free flow ves, rs, dyes, and
so forth.
In a preferred embodiment of the antidrift ition herein, urea-based
complex-forming component (i), in addition to being complexed with ifr component (ii), is
complexed with a superspreader tant. The preader surfactant of the preferred
antidrift composition functions in an aqueous agricultural spray composition to improve the
wetting and spreading of the droplets of the spray composition on the target plants.
The superspreader surfactant can be selected from among any of the known and
conventional superspreader surfactants, e.g., the organosilicon superspreader surfactants
disclosed in US. Patent Nos. 7,507,775; 7,645,720; 7,652,072; 7,700,797; 7,879,916; and,
7,935,842, and in US. Patent Application Publication 2007/013161 1, the entire contents of
which are incorporated by reference herein, and the non~organosilicon superspreader surfactants,
e. g., those sed in US. Patent Nos. 5,821,195; 6,130,186; 6,475,953; 265; and,
7,964,552, the entire contents of which are also incorporated by nce herein.
It is within the scope of this invention to employ a mixture of organosilicon
superspreader surfactant(s) and non—organosilicon superspreader surfactant(s), e.g., as disclosed
in aforementioned US. Patent No. 7,964,552, as optional adjuvant components (iii). Additional
combinations of adjuvant surfactants that may advantageously be included in the antidrifi
composition ofthe invention include organosilicon superspreader surfactant and non-
superspreading organosilicon surfactant; organosilicon superspreader surfactant and nonsuperspreading
, non—organosilicon surfactant; non-organosilicon superspreader surfactant and
non-superspreading organosilicon tant; non-organosilicon preader surfactant and
non-superspreading, non-organosilicon surfactant; and, non-superspreading organosilicon
surfactant and non-superspreading, non-organosilicon surfactant. The weight ratios of the
different types of surfactants in these mixtures can vary widely, e.g., from 12100 to 100:1,
preferably from 1:50 to 50:1 and more preferably from 1:20 to 20:1. All, part or none of these
surfactant mixtures may be complexed with ased complex-forming component (i) of the
antidrifi ition herein. Where only part of a given tant e is complexed with
ureabased complex-forming component (i), the weight ratio of the different types of surfactants
in the mixture may ntially correspond to, or significantly differ from, that ofthe mixture
prior to being complexed.
More particularly, the organosilicon superspreader surfactant can be selected fi‘om
any one or more ofthe known and conventional tri- and tetrasiloxane alkoxylate and/or
hydrolysis-resistant types.
entative of the superspreader surfactants are the polysiloxane alkoxylates
of general formula (I):
(R'RZR3Sioia)(R“RSSiom)n(R"R‘OSiom)p(R7R8R9Siom) (I)
wherein n is 0 or 1; p is 1 or 2; R1 to R8 are methyl; R9 is methyl or, when R10 is methyl, R9 is
R”; R10 is methyl or Rn with R11 being a polyalkylene oxide group of general formula (11):
R]3(C2H40)w(C3H60)x(C4Hs0)le2 (H)
in which w, x and y are independently an integer from 0 to 20, with the o that w is greater
than or equal to 2 and w+x+y is in a range of from 2 to 20; R12 is a hydrogen atom, an aliphatic
radical or an acetyl group; and, R‘3 is a divalent aliphatic radical having the structure (111):
——CH2CH(RM)(R‘5)ZO— (III)
in which R14 is a hydrogen atom or an aliphatic radical, Rls is a divalent aliphatic radical of l to
6 carbon atoms and z is O or 1.
ally advantageous polysiloxane alkoxylates (l) for providing optional
superspreader surfactant of the antidrift composition herein are the trisiloxane alkoxylates, e.g.,
trisiloxane ethoxylates, trisiloxane ethoxylate~propoxylates, etc.
loxane alkoxylates (I) can be prepared in a known manner, specifically, by
the hydrosilylation reaction of a silicon hydride-containing organosiloxane with an unsaturated
polyalkylene oxide.
A number ofpolysiloxane alkoxylates (I) are commercially available such as
Silwet L~77, Silwet 408, Silwet 806, SF1188A and SF1288, all from Momentive Performance
als Inc.
Representative of the hydrolysis-resistant superspreaders are the carbosilane,
disiloxane and hindered trisiloxane surfactants such as those hereinafter described.
le ysis-resistant carbosilane surfactants include those of general
formula (IV):
(R‘6>(R”)(R‘8)Si—R‘9—SirR2°)(R“)<R”) (IV)
wherein R”, R”, R”, R20 and R2' are each independently selected from the group consisting of l
to 6 monovalent hydrocarbon radicals, aryl and a hydrocarbon group of 7 to 10 carbon atoms
containing an aryl group; R19 is a divalent arbon group of l to 3 carbons; R22 is a
polyalkylene oxide group of general formula (V):
R”<02H40)i(csH60)c(ciHsDirk“ (V)
in which R23 is a divalent linear or branched hydrocarbon radical having structure (V1):
—CHZCH(R”>(R26>gO—— (VI)
in which R25 is hydrogen or ; R26 is a divalent alkyl radical of 1 to 6 carbon atoms where
the subscript g may be 0 or l; R”1 is selected from the group consisting of hydrogen,'rnonovalent
hydrocarbon radical of 1 to 6 carbon atoms and acetyl, subject to the limitation that subscripts d,
e and f are zero or ve and satisfy the following relationships:
2§d+e+f§ 20 with d2?“
Hydrolysis-resistant carbosilane surfactant (IV) can be prepared in a known
manner, e. g., through the use ofhydrosilylation reaction to graft an olefinically unsaturated (i.e.,
vinyl, allyl or methallyl) polyalkylene oxide onto a compound of the a:
(R‘6)(R‘7)(R18)Si——-Rl9—Si(RZ°)(R21)H
n Rm-R21 each has the aforedescribed meaning.
Among the le hydrolysis-resistant disiloxane surfactants are those of general
formula (VII):
MM' (V11)
wherein M is thzzgnzgsiom and M' is 113012311232Sio"2 in which R27 is selected from the
group
consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms or R33 in
which R33 is selected from the group consisting of R3‘1R35R3f’SiR37 and 1R32)SiR37 in
which R“; R35 and R36 each independently is selected from the group consisting ofmonovalent
hydrocarbon radical of from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon
radical of from 6 to 13 carbon atoms and R37 is a divalent hydrocarbon radical of from 1 to 3
carbon atoms; R28 and R29 each ndently is selected from the group consisting of
monovalent hydrocarbon radical of from 1 to 6 carbon atoms or R”, and R30 is a polyalkylene
oxide group selected from the group consisting of R38(C2H4C)){,(C3H60)l,(C4H;;O),;R39~ and
R37SiR3’R32(R33(C2HiO)a(C3I-I50)b(C4HgO)cR39) in which R38 is a divalent linear or branched
hydrocarbon radical having the structure (VIII):
—CH20H(R4°)(R“)(10— (VIIl)
in which R40 is hydrogen or methyl; R‘” is a divalent alkyl radical of l to 6 carbon atoms in
which subscript d may be 0 or I; R39 is selected from the group consisting of hydrogen,
lent arbon radical of from 1 to 6 carbon atoms and acetyl subject to the limitation
that subscripts a, b and c are zero or positive and satisfy the ing onships:
2§a+b+c§20 with a; 2,
and R3 and R32 each independently is selected from the group of lent hydrocarbon
radicals having from 1 to 6 carbon atoms or R”.
Disiloxane surfactant (VII) can be prepared in a known manner, e.g., by reacting a
compound ofthe formulaM” in which M” is the hydride precursor ofthe M' structural unit in
disiloxane (VII) under hydrosilylation conditions with an olefinically unsaturated (i.e., vinyl,
allyl or methallyl) polyalkylene oxide.
Useful hindered hydrolysis-resistant hisiloxane superspreader surfactants for
complexing with complex—forming component (i) e first trisiloxane surfactant (IX), second
trisiloxane surfactant (XI) and third tn'siloxane surfactant (XIV) as hereinafter defined:
first hydrolysis-resistant oxane ofgeneral formula (11X):
M‘D’M2 (1X)
wherein M‘ is (R42)(R43)(R44)Siou2, M2 is (R45)(R46)(R47)Si01/2 and D‘ is (R48)(Z)Si0m in
which R42 is selected from a branched or linear hydrocarbon group of from 2 to 4 carbon atoms,
aryl and alkyl hydrocarbon group of4 to 9 carbon atoms containing an aryl substituent of 6 to 20
carbon atoms; R43, R44, R45, R46, R47 and R48 each independently is selected fiom the group
consisting ofmonovalent hydrocarbon radical of 1 to 4 carbon atoms and hydrocarbon radical of
4 to 9 s containing an aryl group of from 6 to 20 carbon atoms, and Z is an alkyleneoxide
group of general formula (X):
R“9(Czr140)iicimoiitciHsorR” (X)
in which R49 is a linear or branched divalent hydrocarbon radical of 2, 3, 5, 6, 7, 8 or 9 carbon
atoms; R50 is selected from the group consisting of hydrogen, monovalent hydrocarbon ls
of from 1 to 6 carbon atoms and acetyl, and in which the subscripts a, b and c are zero or positive
and satisfy the following onships:
2§a+b+c§20 with a; 2;
second hydrolysis—resistant trisiloxane of general formula (XI):
MSDZM“ (XI)
wherein M3 is R52)(R53)Si01/2, M4 is (R54)(R55)(R56)Si01,2 and D2 is (R57)(Z')Si02/2 in
which R“, R52, R53, R54, R55, R56 and RS7 each independently is selected from the group
consisting of monovalent hydrocarbon radical of l to 4 carbon atoms, aryl and alkyl hydrocarbon
group of4 to 9 carbon atoms containing an aryl substituents of 6 to 20 carbon atoms; 2' is a
kylene oxide group of general formula (XII):
lemme»(03H60>C(C4H80)iR59 (XE)
in which R58 is selected from a branched or linear divalent hydrocarbon radical of the general
formula (XIII):
—C4H30(C2H40)—— (XIII)
in which R59 is ed from the group consisting ofhydrogen, monovalent hydrocarbon l
of from 1 to 6 carbon atoms and acetyl, and in which the subscripts d, e and f are zero or positive
and satisfy the following relationships:
2§d+e+f§ 20 with da 2; and,
third hydrolysis-resistant trisiloxane of general formula (XIV):
M5D3M" (XIV)
wherein M5 is R5')(R62)Siom, M6 is (R63)(R64)(R65)SiO./2 and D3 is (R66)(Z")Si02,2 in
which R60, R“, R62, R63, R64 and R65 each independently is selected from the group consisting of
monovalent hydrocarbon radical of l to 4 carbon atoms, aryl, and alkyl hydrocarbon group of 4
to 9 carbon atoms ning an aryl substituent of 6 to 20 carbon atoms, R66 is a linear or
branched hydrocarbon radical of 2 to 4 carbons; Z" is a polyalkylene oxide group of general
formula (XV):
R67 (C2m0)3(C3H50)h(C4HsO)iR68 (XV)
wherein R67 is a linear or branched divalent hydrocarbon radical of2, 3, 5, 6, 7, 8, or 9 carbon
atoms; R68 is selected from the group ting of hydrogen, monovalent hydrocarbon radical of
from 1 to 6 carbon atoms and acetyl, and in which subscripts g, h and i are zero or ve and
satisfy the following relationships:
2§g+h+i§20 with (0,22.
Hindered, hydrolysis—resistant tn'siloxanes (IX), (XI) and (XII) can be prepared in
a known manner, e.g., by reacting the silicone e precursor of one of the aid
trisiloxanes under hydrosilylation reaction conditions with an olefinically unsaturated (i.e., vinyl,
allyl or methally1)polyalkylene oxide.
Useful ganosilicon superspreader surfactants include Capstone®
flurosurfactants t), and RhodasurfiE DA—530 (Rhodia).
Useful non—superspreading organosilicon surfactants include Silwet® L—8610, L—
8020, L—6900, L~6988 and .
Useful non—superspreading, non-organosilicon surfactants include those of the
anionic, nonionic, cationic and amphoteric varieties.
Suitable non-superspreading, non-organosilicon anionic surfactants include
sodium dodecyl sulfate, alkylcarboxylic acids (Lutensit® AN 45 (BASF)), sodium fatty alcohol
polyglycol ether sulfates (Emulphor® PAS 30 (BASH), sodium laureth sulfate (Rhodapex®
ESB 7O FEA2 (RhodiaD, and the like.
Suitable non~organosilicon nonionic surfactants, which depending on structure
may or may not be superspreading, include nonylphenol and octylphenol ethoxylates, ethylene
propylene oxide block copolymers such as the Pluronics® (BASF), fatty l
ethoxylates n® emulsifiers (BASFD, alcohol ethoxylates (Rhodasurf® surfactants
(Rhodia)) and the like.
Where an organosilicon superspreader surfactant (iii) is present in the antidrifi
composition, it can be especially advantageous to include a non-organcsilicon nonionic
surfactant of l formula (XVI):
CH3<CH2)¢(C)dolR7° (XVI)
wherein R69 is the same or different and is selected fiom the group consisting ofhydrogen and an
alkyl of l to 4 carbon atoms; 0 is 5 to 9, d is 0 to 4, c+d is 5 to 9 and t is 0 or 1; R70 is anonionic
hydrophilic moiety with the proviso that when t is 0, R70 is
and when t is l, R70 is selected from the group consisting of (i) ]f{C3H5O]gH and
(ii) 5)h-C5H1005 in which fiS 1 to 40, g is 0 10 40 and h is 1 t0 4, all as disclosed in U.S.
Patent No. 5,558,806, the entire contents of which are incorporated by reference herein.
Combinations oforganosilicon-containing superspreader surfactant (iii) and nonionic
cosurfactant (XVI) that can advantageously be incorporated in the antidrift composition herein
include the products Agrospred 100 and Agrospred 730, both available fiom Momentive
Performance Materials Inc.
Suitable non-organosilicon cationic surfactants include tallow amine ethoxylates,
trimethylalkylammonium chloride, and the like.
Suitable non-organosilicon amphoteric surfactants include the etaines and
cocamidobetaines, all of which are able to be complexed with urea-based complex-forming
component (i).
Specific antifoam additives include silicone oils, silica/silicone oil blends, silicone
resins, alkoxylated cloud-point antifoarns, and the like; c anticaking/free—flow additives
include silica, calcium silicate, sodium silicate, tricalcium phosphate, bentonite, aluminum
silicate, magnesium trisilicate, and the like; and, specific stickers include latexes, and the like.
Where utilized, these and other al nt components (iii) can be
incorporated in the antidrifi ition ofthe invention in known and conventional amounts.
4. Optional Formulation Component (iv)
it is also within the scope of the ion to provide the antidrifi composition
herein as a semi-wet paste or even as a fully dissolved or dispersed liquid concentrate in which
case any added water, organic solvent, etc, employed in providing the ift composition in
one of these forms can be considered an optional formulation ent (iv).
S. Ranges ofAmounts of Components (i), (ii), and al Adjuvant
Component (iii) in the Antidrift Composition
Provided that urea-based complex-fanning component (i) is present in the
antidrift composition of the invention in at least an amount that is ive to form a complex
with significant amounts of antidrift component (ii), e.g., at least 50, preferably at least 80, and
more preferably at least 95, weight percent of ifi component (ii), and ifi component
(ii) is present in the antidritt ition in at least an amount that is effective to provide
iable drifi control of the aqueous spray composition to which the antidrifi composition is
added, components (i) and (ii) ofthe antidrifi composition can be present therein within broadly
specific amounts.
Thus, e.g., the antidriit composition of the invention can contain an amount of
complex-forming component (i), antidrift component (ii) and optional adjuvant component (iii),
within one of the weight parts ranges A, B and C as hereinafter set forth (with weight parts
values for a particular antidriit composition ng 100 weight percent):
Component of Weight Pans Ranges A, B and C
the Antidrift
Common. . “—C
70—95 80—98
0540
6. General Preparative Procedures
The antidn'ft composition ofthe invention can be readily ed by a variety of
procedures. Thus, e. g., the desired s of antidrifi component (ii) and, if ed, optional
adjuvant component (iii), can be dissolved in an aqueous and/or organic solvent solution of the
desired amount of urea-based complex-forming component (i) followed by removal ofthe
water/orgaInc solvent to e a substantially solid material which, if desired, can be
ized, granulated, flaked, pelletized, prilled or otherwise processed to provide ly
convenient end-user forms for addition to aqueous spray media. Organic solvents le for
this purpose include low boiling polar solvents such as methanol, ethanol, propanol, isopropanol,
acetone, methylethylketone, dimethylformamide, dimethylsulfoxide, and the like. Removal of
solvent can be accelerated by application of suitable levels of heat and/or reduced pressure.
Drying can be accomplished employing any of several known and conventional techniques for
removing solvent(s) from ved , e.g., natural air drying, oven drying, drum drying,
spray drying, evaporative drying under ambient or reduced pressure, supercritical , etc.
Where such drying techniques result in a bulk solid or fairly large lumps of solid
material, it is generally desirable to grind, mill or otherwise reduce the dry material to some
particulate form, e.g., powder, granules, flakes, pellets, prills, etc., in order to facilitate packaging
and/or handling by end-users. Whether the particulates are produced by grinding/milling the
dried material or are produced directly from a on or melt by such techniques as spray
drying, prilling, and the like, the particulates can range widely as to both average particle size
and particle size bution Antidrifi compositions having average particle sizes of from 50 u
to 10 mm, and preferably from 200 u to 5 mm, and in which from 50 to 70, and preferably from
60 to 90, weight percent of the compositions are made up of particles having
average sizes of
from 400 n to 1 mm, are generally quite suitable forms of the compositions herein.
In accordance with another procedure for producing the ift composition of
the invention, the desired amounts of antidn'ft component (ii) and, optionally, adjuvant
component (ii), can be uniformly ved in the desired amount ofmolten urea-based complex-
forming component (i) (in the case of essentially pure or cal grade urea, at or above its
melting point of 133-135°C) and following cooling and solidification of the mixture, further
sing ofthe mixture, e.g., grinding or milling to provide powder, as previously indicated.
To rate dissolution of antidrifi component (ii) and any optional nt component (iii)
into the molten ased x-forming component (i), a minor amount of water, e.g., up to
% by weight, may be added to complex-forming component (i) prior to heating the resulting
mixture to its (reduced) melt temperature.
B. Aqueous Spray Compositions ning the Antidn'ft Composition of the
Invention
The antian composition of the present invention is especially useful for addition
to aqueous spray compositions intended for agricultural (inclusive of horticultural, turf and/or
forestry) application. The amounts of antidrift ition to be added to a given aqueous spray
composition will, of course, be that which is effective to significantly reduce drift ofthat
particular spray composition.
Determining the ive range of amounts of antidrifi composition for a given
aqueous spray composition will be influenced by a variety of factors including the precise
formulation of the antidrifi composition, the desired distribution of droplet sizes for the spray
composition under consideration, the spray conditions and the nature of the target
plants/crops/vegetation.
Optimum amounts of antidrifi composition for a c spray composition and
spraying operation can be readily determined employing routine experimental testing procedures
such as those described below.
For many spray compositions, amounts of antidrift composition ofthis invention
ranging from 0.01 to 5, and preferably from 0.1 to 1, weight percent can be incorporated therein
with generally good drift reduction results.
Agricultural sprays, which in addition to water and the soluble antidrift
composition of the ion, will include one or more known and conventional active
ingredients, fertilizers, micronutrients, adjuvants, agricultural excipients, cosurfactants, etc, such
as those now bed.
1. Pesticides
Pesticidal sprays include at least one pesticide. Optionally, the pesticidal spray
may include excipients, cosuifactants, solvents, foam control agents, tion aids, biologicals,
micronutrients, izers, and the like. The term "pesticide" means any compound that is used
to destroy pests, e. g., rodenticides, insecticides, miticides, acaricides, fungicides, herbicides, and
so forth. Illustrative examples ofpesticides that can be ed include, but are not limited to,
growth regulators, photosynthesis tors, pigment inhibitors, mitotic disrupters, lipid
biosynthesis inhibitors, cell wall inhibitors, and cell membrane disrupters. The amount of
pesticide employed in a spray composition will vary with the particular type of pesticide.
Specific es ofpesticide compounds that can be incorporated in a spray composition
include, but not limited to, herbicides and growth regulators such as: phenoxy acetic acids,
phenoxy propionic acids, phenoxy butyric acids, benzoic acids, triazines and s—triazines,
substituted ureas, uracils, bentazon, desmedipham, methazole, phenmedipham, pyridate,
amitrole, clornazone, flun'done, norflurazone, dinitroanilines, isopropalin, oryzalin,
pendimethalin, prodiamine, trifluralin, glyphosate, sulfonylureas, imidazolinones, clethodim,
diclofop—methyl, fenoxaprop-ethyl, op-p-butyl, haloxyfop—methyl, quizalofop,
sethoxydim, dichlobenil, en, bipyridylium compounds, and the like.
Fungicide compositions that can be utilized in the s spray composition
include, but are not d to, aldimorph, tridemorph, dodemorph, dimethomorph; flusilazol,
azaconazole, onazole, epoxiconazole, furconazole, propiconazole, tebuconazole and the
like; imazalil, anate, benomy] carbendazirn, chlorothialonil, dicloran, trifloxystrobin,
fluoxystrobin, dimoxystrobin, azoxystrobin, anil, prochloraz, flusulfamide, famoxadone,
captan, maneb, mancozeb, dodicin, dodine, metalaxyl, and the like.
Insecticide, larvacide, miticide and e compounds that can incorporated in
the aqueous spray ition include, but are not limited to, Bacillus thuringiensis (or Bt),
spinosad, abamectin, doramectin, lepimectin, pyrethn‘ns, carbaryl, primicarb, aldicarb,
methomyl, antitraz, boric acid, imeforrn, novaluron, bistrifluron, triflumuron,
diflubenzuron, imidacloprid, diazinon, acephate, endosulfan, kelevan, dimethoate, azinphos-
ethyl, azinphos—methyl, izoxathion, chlorpyrifos, tezine, lambda-cyhalothrin, perrnethrin,
bifenthrin, cypermethrinm, and the like.
2. izers and Micronutrients
Fertilizers and micronutrients include, but not limited to, zinc sulfate, ferrous
sulfate, ammonium sulfate, urea, urea ammonium en, ammonium thiosulfate, potassium
sulfate, monoammonium phosphate, urea phosphate, calcium nitrate, boric acid, potassium and
sodium salts of boric acid, oric acid, magnesium hydroxide, manganese carbonate,
calcium polysulfide, copper sulfate, manganese sulfate, iron e, calcium sulfate, sodium
molybdate, calcium chloride, and the like.
3. Adjuvants and Agg'cultural Excipients
Many pesticide applications require the addition of an nt to the aqueous
foliar surfaces. Often that nt is a
spray formulation to provide wetting and spreading on
surfactant that is capable ofperforming several functions such as increasing spray droplet
retention on difficult to wet leaf surfaces, enhancing spreading to improve spray coverage and
providing penetration of herbicide into the plant cuticle.
Buffers, preservatives and other standard agricultural excipients known in the art
may also be ed in the spray composition.
Suitable organic solvents for inclusion in the spray composition include alcohols,
ic solvents, oils (e. g., mineral oil, vegetable oil, silicone oil, and so forth), lower alkyl
esters ofvegetable oils, fatty acids, ketones, glycols, hylene glycols, diols, paraffinics, and
so forth. Particular ts e 2, 2, 4-trirnethyl, l-3~pentane diol and alkoxylated
(especially ethoxylated) versions thereof as illustrated in US. Pat. No. 5,674,832, the entire
contents ofwhich are incorporated by reference herein, and n—methyl—pyrrolidone.
4. Cosurfactants
Useful cosurfactants herein include ic, cationic, anionic, amphoteric and
zwitterionic surfactants and any of their mixtures. Surfactants are typically hydrocarbon-based,
silicone—based or arbon—based.
Moreover, other cosurfactants having short chain hydrophobes that do not
interfere with superspreading, e.g., those described in US. Patent No. 5,558,806, the entire
contents h are orated by reference herein, are also useful.
Useful surfactants include alkoxylates, especially ethoxylates, containing block
copolymers including copolymers of ethylene oxide, propylene oxide, butylene oxide, and
es thereof; alkylarylalkoxylates, especially ethoxylates or propoxylates and their
tives including alkyl phenol ethoxylate; arylarylalkoxylates, especially ethoxylates or
propoxylates. and their derivatives; amine alkoxylates, ally amine ethoxylates; fatty acid
alkoxylates; fatty alcohol alkoxylates; alkyl sulfonates; alkyl benzene and alkyl naphthalene
sulfonates; sulfated fatty alcohols, amines or acid amides; acid esters of sodium isethionate;
esters of sodium sulfosuccinate; sulfated or sulfonated fatty acid esters; petroleum sulfonates; N-
acyl sarcosinates; allcyl polyglycosides; alkyl ethoxylated amines, and the like.
Specific es include alkyl acetylenic diols (Surfynols®, Air Products),
pyrrilodone based surfactants (e.g., Surfadone® LP 100, Ashland), 2-ethyl hexyl sulfate, isodecyl
alcohol ethoxylates (e.g., urt® DA 530, Rhodia), ethylene diamine alkoxylates
(Tetronics®, BASF), ethylene propylene oxide copolymers (Pluronics®, BASF), -
type tants a) and diphenyl ether gemini—type surfactants (DOWFAX®, Dow
Chemical).
Preferred surfactants include ethylene oxide/propylene oxide copolymers
(BO/PO); amine ethoxylates (tallowamine ethoxylates); alkyl polyglycosides; oxo-tridecyl
alcohol ethoxylates, and so forth.
5. Other Aqueous Spray Components
The aqueous spray composition can include one or more other agrochemical
components. Suitable such agrochemical components are growth regulators, biologicals, plant
nutritionals, nic mineral oil, methylated seed oils (i,e. methylsoyate or methylcanolate),
vegetable oils (such as soybean oil and canola oil), water conditioning agents such as
Choice.RTM. and Industries, Greeley, Colo.) and Quest (Helena Chemical, Collierville,
Tenn), modified clays such as SurroundRTM. (Englehard Corp.,), foam control agents, wetting
, dispersants, emulsifiers and deposition aids.
[0075! Agricultural spray compositions may be made by combining in any combination
and/or sequence in a manner known in the art, such as mixing, water, one or more of the above
spray components and the antidrifi ition of the present invention, either as a tank-mix, or
as an "In—can" formulation. The term mix" means the addition of at least one agrochemical
to a spray medium, such as water or oil, at the point of use. The term "In-can" refers to a
formulation or concentrate containing at least one agrochemical component. The "In-can"
formulation may then be diluted to its application concentration at the point ofuse, typically in a
tanlemix, or it may be used undiluted.
C. Examples Illustrating the Antidrift Composition of the Invention
1. Determination of Spray Drifi
Spray drift was determined in the examples that follow employing the spray booth
apparatus of Figure 1 that has been modified to function in the manner of a small wind . A
flat-fan spray nozzle (UNUET 8002B) was fixed in place at the top of the booth, about 56 cm
from the right hand side ofthe hood. A heat gun in "fan mode" was used as a wind source and
placed to the right ofthe spray. A water sensitive paper coupon was held on the opposite side of
the spray‘ This setup is shown in Figure l. The spray drift tests were run at a spray pressure of
2.85-3.00 atrn and the spray time was 10 seconds. Three to four sprays were run for each
solution. The amount of drift was ined by averaging the number of drops counted in five
0.125 cm2 circles on each water sensitive paper coupon. The coupons measured approximately
1.8 x 2.5 cm. Water was sprayed as a control at the beginning and end of each set.
2. Determination of Spreading! getting
The spreading ability of the various superspreaders utilized herein was determined
by depositing a single drop (10 microliters) of solution onto a clean, flat polystyrene dish. The
polystyrene surfaces were cleaned by rinsing with isopropanol and then with deionized water.
The dishes were then dried with dry nitrogen gas. The diameters of the resulting drops were then
measured Each solution was tested 2 to 4 times and the average er was calculated.
es 1-10
In these and all ofthe other examples that follow, all percentage amounts of
indicated materials are by weight.
Spray drift and spreading tests were carried out on a ical mixture of a
rylamide (PAM) antidrifc agent (Zetag 1100, BASF) and a complex of urea and a
hydrolysis-resistant carbosilane superspreader surfactant ("Silicone A") (Example 2) made by
adding the superspreader surfactant to molten urea. The results ofthese tests, presented in Table
1 below, show that this mixture exhibits a level of drift reduction that is substantially lent
to that exhibited by a similar concentration ofPAM antidrifi agent (Example 7) and
wetting/spreading properties that are significantly better than deionized water (Examples 1 and
8) e the low tration of Silicone A.
Table 1: Spray Drift and Spreading Test Results Data for Various Urea Complexes
Aueous nra Coma n
% Spray Drift St Dev
% Silicone % Diameter St Dev
iale Test Samle Descn‘ otion Evaluated Urea A PAM 0125mm2 0.1.‘250m2 mm
Tali—-mmechanical blend of 97% 0.33 0.296 0024 0.010 3.7 1.6 10.3
urea complex ining
7.6% Silicone A) and 3%
PAM -
Linea complex containing 0.833 0.790 O033
1.2% PAM and 4.0%
ne A and made from
aq. soln of these
com - unents
urea complex containing 0.435 0391 0033 0.010
2.3% PAM and 7.74%
Silicone A and made from
an. soln of these
cornonents
urea complex containing 0.904 0.813 0.070 0021
2.3% PAM and 7.74%
Silicone A and made from
aq. soln of these
urea complex containing 50.00 0000 0010
1.96% PAM made from
molten urea .—
m_—m----—mm
While the mechanical mixture of urea/Silicone A superspreader complex and
PAM (Example 2) yields a free-flowing particulate product providing excellent drift control and
good spreading ties, it does not address the poblern of the characteristically slow
dissolution of the PAM antidrift agent. In addition there1s a n that the two kinds of
particulates in the mixture, i.e., urea/Silicone A complex and PAM, will separate from each other
to some extent during storage thereby resulting in a heterogenous mixture that may complicate
achieving the required proportioning when ing the aqueous spray composition.
In Example 6, and in accordance with the invention, the PAM antidrifi component
was dissolved within the molten urea to complex the PAM. This liquid mixture was then cast
onto a room temperature aluminum dish to form a e solid. This solid inclusion complex was
then broken up and ground to form a white, free-flowing powder.
Urea inclusion complexes containing both the antidrift agent and superspreader
surfactant were ed by dissolving the superspreader, ift agent and urea in water in the
desired ratio. The water was then removed by evaporation by placing the solution in an oven at
80-95°C for 2—3 days resulting in white and semi-crystalline solids. When ground, the ing
antidrifi compositions were white, free-flowing s les 3-5).
When diluted to achieve a superspreader concentration of 0.033% and a PAM
concentration of0.01% (Examples 3 and 4), these inclusion complexes reduced spray drift as
well as the control solution of 0.01% PAM (Example 7). Surprisingly, the urea inclusion
complexes ples 3 and 4 also exhibited better spreading than the 0.033% control solution
of Silicone A superspreader (Example 9). The urea/PAM/Silicone A superspreader ion
complex ofExample 4 was also evaluated at approximately twice the initial concentration
resulting in a PAM concentration of0.021% and a superspreader concentration of 0.070%
(Example 5). This complex ted excellent drift reduction and better spreading/wetting than
the more dilute complex solutions of Examples 3 and 4. The complex ofExample 5 also showed
better spreading/wetting that the 0.070% control solution of Silicone A superspreader
(Example 10). Example 6, a urea ion complex ofPAM with no superspreader Silicone A,
showed excellent drift reduction but very poor spreading ties comparable to those
observed with water thus demonstrating that urea by itselfdoes not improve spreading/wetting
properties.
Examples 11~21
Another set of urea/PAM/Silicone A superspreader inclusion complexes were
ed as indicated in Table 2 below. The complexes of Examples 12-15 were made via the
aqueous solution procedure described above in order to determine how much Silicone A
superspreader and PAM could be incorporated in the inclusion complex. Examples 16 and 18
were made with polycrylamide-polyacrylic acid (PAM-FAA) copolymcr having a nominal
weight average lar weight of 15,000 (Aldrich) as the antidrifi agent instead ofPAM.
Example 16, like Examples 12-15, was made via the aqueous solution procedure. Examples 17
and 18 were prepared fiom molten urea with PAM and PAM—FAA copolymer, respectively. All
ofthese complexes were sprayed at a dilution ing an antidrifi component tration of
0.015%. At these dilutions, the Silicone A concentration of Examples 12-16 was 0.050% while
those of Examples 17 and 18 was 0.041%. The results of spray—drift and spreading/wetting tests
are summarized in Table 2 below.
Table 2: Spray Drift and Spreading Test s for Various Urea Complexes
Sara Com on
% Test
Sample Silicone PAM or StDev
Examle Test Sam -le Descri ntion Dianmeter PAMPAA O1 . mm
I11 l—248E—valuatedU-Drea/”—flm 12 urea complexoontainlng 1-.18 0.050 O015
1 20% PAM and 4.03% Silicone
com- ments
13 urea complex containing 0.649 0015
231% PAM and 7.67% Silicone
A made from aq. soln of
com - s
14 urea complex containing 3.00% 0.44 0.015
made from aq. soln of
com 0 o nenls
urea complex containing 3.99% 0.376 0.050 0.015
PAM and 13.31% Silicone A
made from aq. soln of
comments
.s O) urea complex containing 2.31% 0849 0.050 0015
PAM/FAA (Aldrich) and 7.67%
e A made from aq. soln of
ccmonents
‘7 IIWIIII
PAM and 5.5% Silicone A made
from molten urea
.a. 8 urea complex containing 2.0% 0.750 D041 O015
PAM/FAA (Aldrich) and 5.5%
Silicone A made from molten
urea
——.m0000 0015
Im21IIIIII.I=I0050
As shown in the Table 2 data, all of the urea/antidrifi agent/Silicone A
superspreader inclusion complexes les 12-18) provided levels of spray-drift reduction
essentially equivalent to that of the PAM control (Example 19). In addition, these inclusion
complexes provided better spreading/wetting properties than the lent concentration of
Silicone A superspreader in water (Example 20).
Polyacrylarnides such as Zetag 1100 (BASF) currently do not have EPA ”inert"
status under Title 40, Code of Federal tions Sec. 180.960. However PAM/FAA
copolymers with average molecular weights in atomic mass units (amu) equal to or greater than
1200, and PAM/PAA/Na polymers (CAS#250853) with a number average molecular weight
(amu) of at least 18,000, are considered "inert" under this regulation and are thus acceptable for
use in agricultural sprays.
Examples 22-29
Urea ion complexes containing PAM-FAA copolymer, sodium salt (PAM—
PAA—Na) (Zetag 4100, BASF), both without and with Silicone A superspreader, were made from
molten urea as was a ison urea inclusion complex containing PAM and Silicone A.
Aqueous herbicidal spray compositions were prepared containing 0.75% of these urea inclusion
complexes and 1% glyphosate isopropyiamine salt ("glyphosate [PA salt") herbicide and
evaluated for reduction of drift, increased spreading and herbicidal performance when d
on velvetleaf. The results of these tests are summarized in Table 3 below.
Table 3: Spray Drifi and Spreading Data for Various Urea xes
w- ueous HerbicidaISraCom-- on
%Test % PAMor Spray Drift Spread Contml % Centre
% Giy— “/o PAMFAA. (drops/ Diameter atter1 after 2
Exame Test Sam-ls Descriiion uhosate Evaiuat
r uneaSificoneA Na (1—1250112m-mw_eek341
23 urea complex containing 7500. 0041 0.015 8.7
% PAM and 55%
Silicone A
1.0% ANa and no
Silicone A
urea complex containing 0750 0.71 0.038 O0075
1.0% PAM-PAA-Na and
.0% Silicone A
-———n——-_237 n-flmnwManna-urn:
n_—-___-
As shown in the data of Table 3, the greatest reduction in drift was achieved with
urea/PAM-PAA—Na complex ning no Silicone A superspreader (Example 24). The
addition of Silicone A superspreader to the urea/PAM-PAA—Na inclusion complex of Example
resulted in a slight increase in drift. While the urea/PAM/Silicone A inclusion complex of
Example 23 resulted in slightly better drift reduction than the urea/PAM-PAA-Na/Silicone A
complex ofExample 25, twice as much PAM was required to achieve this result.
Drop-spreading tests showed that ons containing ne A superspreader
resulted in average drop spread diameters of approximately 20 mm regardless ofwhether or not
they had been part of a urea inclusion complex and regardless of r or not glyphosate
herbicide was present. The compositions that did not contain Silicone A superspreader did not
spread well, with resulting drop diameters being about 5 mm.
The three herbicidal compositions containing urea ion complexes
(Examples 23-25) were sprayed on velvetleaf. A solution of0.042% Silicone A and 1%
glyphosate IPA salt (Example 26) was used as a control as was a plain 1% glyphosate [PA salt
solution (Example 27). After one week the three herbicidal compositions containing the urea
inclusion complexes and glyphosate IPA salt (Examples 23-25) were more effective at killing the
velvetleaf than the Silicone A and glyphosate IPA salt control (Example 26) which was slightly
more effective that the 1% glyphosate control (Example 27). Afier two weeks, the three urea
inclusion complexes and the silicon A/glyphosate [PA salt combination (Examples 23-26) all
exhibited greater than 90% idal effectiveness while the glyphosate IPA salt control
provided only 81% herbicidal effectiveness.
Exam les 30~38
Larger batches of urea inclusion xes containing PAM-PAA—Na antidrifi
agent and Silicone A superspreader were prepared in order to fy any possible ms that
might result when scaling up from 40-50 g to 120—150 g batch ties. The three inclusion
complexes all contained 5% Silicone A superspreader and different concentrations ofPAM-
PAA-Na antidrifi component. s spray compositions ning 0.75% of each of these
inclusion complexes were then prepared and tested for spray drift control and spreading/wetting
ties. The results of these studies are presented in Table 4 below.
Table 4: Spray Drift and Spreading Test s Data for Complexes and
Mixtures ofUrea and PAM—PAA—Na Copolymer Antidrifi Agent
Aueous Sta Com- «ition
Average
Spray Average
% Drift
% Sample ne Antidritt
Exam-la——_——__&Test Sam-1e -tion Evaluated %Urea A
31 urea x containing 075 0705 00375 0.0075 5.0 24 23.5
1% PAM~PAA~Na and 5%
Silicone A
1.33% PAM-PAANa and
% Silicone A
urea complex containing 0.707 0.0375 00050
% Sllioone A I III-I
PAM-FAA coo mer “-0.0075
urea and PAM-PAA—Na
Silicone A _-__—-_—223
37 mechanical mixture of - 0.705 0.0375n---
urea and Silicone A
38 ——-—-——
As observed with the smaller scale lots, the inclusion complexes ofTable 4
(Examples 31-33) ted good drift control that was equivalent to that provided by the control
samples ofPAM-PAA—Na with and without urea (Examples 34 and 35). The urea inclusion
complexes also exhibited spreading/wetting properties that were as good as or better that that
obtained with the s Silicone A solution (Example 36). The solution of Silicone A with
urea (Example 37) spread a little better than the ne A solution (Example 36). The inclusion
complexes of Examples 31 and 32 resulted in drop diameters that were a little better than the
Silicone A solution. The inclusion complex of Exhibit 33 demonstrated significantly better
spreading/wetting properties than the silicone superspreader solution of Example 36.
Examples 39-47
[0097} The effect of complexing the antidrifi agent in urea on the dissolution time ofthe
antidrift agent was also evaluated. Full ution was considered to have been achieved when a
solution appeared clear and was lump—free when poured. The s ofthese dissolution studies
are presented in Tables 5 and 6 as follows:
Table 5: Dissolution Time for Various PAM-PAA-Na Compositions
Final Pa‘lide Size i PAMPAANa
(diernelerw % Sample % Fnal Urea %
. i Disses/ed Solvent Cmoerdafion Tme min
“a“W IIIWIWI
complex (15% Pam/v}-Nn
98.5% urea
III-IIIcomplex(1.5%Pamin98.5%urea
DI water
IIIIIIIIureainDlwater
IIIIEI
As the dissolution data in Table 5 show, both the flaked and ground antidrift
composition of the invention (Examples 39 and 40) ved in less than 5 minutes whereas the
PAM~PAA—Na copolymer required 185-200 minutes to dissolve in the aqueous urea solutions
(Examples 41 and 42) and 245 minutes to dissolve in water (Example 43).
Table 6: Dissolution Times for s PAM-PAA—Na Compositions
Examle Test Sem-le -tion % Urea Cool mer ne A Time min
441% urea complex (94% 0.940 0.010 0.050
urea. 1% PAMFAA-Na
-and 5% Silicone A-Sam-le 1
P—AMFAA-Na I 0.010 IIfiI
_urea and PAM—PAA—Na 0.940 0.010 _m_
As the ution data in Table 6 show, Example 44, a 1% on of urea
inclusion complex (94% urea, 1% PAM-PAA—Na and 5% Silicone A) required 9 minutes of
continuous rolling to fully dissolve. Example 45 was prepared by sequentially dissolving the
individual components of Example 44. The urea, a fine powder, and Silicone A, a liquid, were
added first. These ients went into solution very quickly. The PAM-PAA—Na, a fine,
granular solid, was then added. The PAM-PAA—Na required 135 minutes to fiilly dissolve.
Example 46, PAM—PAA—Na by itself, required 690 minutes to full)r go into solution. However,
when mixed with urea in Example 47, the PAM-PAA—Na ved in just 90 minutes. It is clear
from these dissolution studies that the presence of urea accelerates the solubilization of PAM-
PAA—Na. It is also evident that the PAM-PAA—Na component of the urea/PAM-PAA—
licone A inclusion complex dissolves much faster than the equivalent amount of non-
complexed PAM-PAA—Na in a urea solution.
Examples 48~57
These examples illustrate antidn'i’c compositions of the invention containing a
conventional trisiloxane superspreader surfactant ("Silicone B").
Two urea complexes were prepared, one in the absence of water ("dry
preparation") and one to which water was added ("wet preparation"). For both ations, 94g
urea, 1g PAM-PAA-Na antidrifi component and 5g Silicone B superspreader component were
added to a flask. In the case of the wet ation, 10g DI water were also added to its flask.
Each flask was then attached to a Rotovap and a nitrogen blanket was applied. The flasks were
partially ged in an oil bath set at 150°C and rotated at approximately 100 rpm until the
urea melted and the PAM—PAA—Na and Silicone B components dissolved n.
Dissolution times (min) for the dry— and wet-prepared urea/PAM-PAA—Na/
Silicone B complexes and spreading test results are presented in Table 7 below:
Table 7: Urea Complex Dissolution Times and Spreading Results after 1 and 5
Weeks Storage of ing on
1 Week 5Weeks
Spreadst diameter
-_--'“'“ml-l—Dm_lwater ——mfi-
n---un-—Wet O—375 O0375
The spreading data in Table 7 show that the urea complexes of Examples 49 and
50 spread just as well as the equivalent concentration of Silicone B superspreader in the control
(Example 51) trating that the wetting ties of Silicone B are not adversely affected
by either the urea complex-forming component or the PAM—PAA—Na antidrift ent and
that the Silicone B does not undergo significant hydrolysis either during the synthesis of the
urea/PAM—APP-Na/Silicone B complex or during 5 weeks of storage.
As the dissolution data in Table 7 show, the on of water to the mixture
providing the wet urea complex of e 50 resulted in a dissolution time of 25 minutes in
contrast to the dissolution time of 45 minutes for the dry urea complex of Example 49. While
the wet urea complex of Example 50 contains some small amount ofwater, when ground the
resulting product exhibited some degree of lity. Removal of some or all of this water to
provide an essentially water-free complex, e.g., one comparable in appearance and flow to the
dry urea complex of Example 49, may be carried out to improve the sability of the wet
urea complex ofExample 50.
The spray—drift test results for the dry~ and wet-prepared urea xes of
es 49 and 50 of Table 7 are presented in Table 8 below:
Table 8: Urea Complex Drift Results
Average
Spray Drift St Dev
Test Sample % Sample % (drops! (drops/
E-xam-le Desert-lion Evaluated % Urea Silicone B
——__P-AM-PAA0—.125cm20—.125cm2296
-Examrte49
Exam -le 49
Exam I la 50
_——__——*56 10% PAM-FAA-Na--_-_———
The spray-drift data presented in Table 8 demonstrate that aqueous solutions of
both the dry complex (Examples 53 and 54) and the wet complex (Example 55) reduced spray
drift by approximately 75% in comparison with the water controls (Examples 52 and 57) and
produced only slightly more drift than the PAM-APPaNa control solution (Example 56).
es 58-75
{0111] Employing either the solvent solution procedure or the molten urea-based
complex-forming ent (i) procedure described above and illustrated in the examples, the
antidrift compositions of Table 9 below further illustrating the invention can be prepared:
Table 9: Additional Antidrifi Compositions
% Optional
Superspreader
% Urea-based Complex— % Antidrift Adiuvant % Opfional onal Adjuvant
Example forming Component (i) Component (ii) Component (iii) Component(s) (iii)
m 90%.... amps
83% urea 10%CMHPG 7% silicone A — - -
93% miourea mam—FAA
A 47% urea; 1% PAM~PAA 2.5% ne B 2.5% anionic surfactant"
47% thiourea
62% urea; 2% PAM 3% nonionic surfactant
% urea formaldehyde 3% latex sticker5
70% urea; 1.5% PAM-PAA-Na 7.5% Silicone C
21% urea formaldehyde
93.5% urea hydrate 1% PAM 5% Silicone C 05% silicone antifoam
90% urea hydrate 5% xanthan gum 4% Silicone C 1% tailow amine
40% urea; 1% PAM-FAA 6% Silicone C 3% anionic surfactant
50% urea hydrate
—89.5% urea phosphate 2% PAM-PAA-Na 8% Silicone C 0.5% silicone antifoam
—92% urea phosphate 1% PAM—PAA5Na 5% Silicone D 2% latex sticker
80% urea; 1.2% PAM-PAA-Na 6% Silicone D
12.8% urea phosphate
—935% urea sulfate 1 5% PAM 5% Silicone o_
91% urea sulfate 1.5% PAM 7.5% Silicone D_
72 45% urea; 1.5% PAM-FAA 4.5% Silicone A 4% trimethylinonanoi ethoxylate'
70% urea phosphate; 1% A 2.5% Silicone B 2.5% alkylpoiyglucoside
24% urea sulfate
33% urea hydrate; 09% A-Na 6% Silicone A 0.1% ne arn'
60%urea phosphate
-11% urea sulfate80% urea hydrate, 14% PAMFAA-Na 7.5% Silicone A 0.1% sodium silicate
HPG=—hydroxypropyl guar
CMHPG = carboxymethyl hydroxypropyi guar
Silicone C = hydrolysis—resistant disiloxane superspreader surfactant
Silicone D = hydrolysis—resistant oxane superspreader tant
Triton X—100 (Dow)
Sodium dodecyl sulfate
Sag 47, Momentive Performance Materials Inc.
2‘ TMN-6 Dow
9 ol GD 70, BASF
1° Antifoam OR90, Momentive Performance Materials Inc.
While the invention has been described with reference to particular embodiments,
those skilled in the art will understand that various changes may be made and equivalents may be
tuted for elements thereof without ing from the scope of the invention. It is intended
that the invention not be limited to the particular embodiments sed but that it include all
embodiments falling within the scope of the appended claims.
Claims (1)
1. A solid, water-soluble antidrift composition which comprises a urea—based x—forming component (i) complexed with at least a portion of an antidrift component (ii), the ift composition further ing an adjuvant component (iii) which is a superspreader surfactant with all, some or none of the superspreader surfactant being xed with urea—based complex—forming component (i), wherein ased complex—forming component (i) is at least one member selected from the group consisting of urea, ea, urea formaldehyde, urea hydrate, urea phosphate and urea sulfate, wherein the antidrift component (ii) is selected from the group consisting of amylamide homopolymers and copolymers and their salts, wherein the superspreader surfactant is at least one organosilicon surfactant selected from the group consisting of polysiloxane alkoxylate surfactant (1), hydrolysis—resistant carbosilane tant (IV), hydrolysis—resistant disiloxane surfactant (VII), first hydrolysis-resistant trisiloxane surfactant (IX), second hydrolysis- resistant trisiloxane surfactant (XI) and third hydrolysis-resistant oxane (XIV) as hereinafter defined: polysiloxane alkoxylate surfactant of general formula (I): (R‘R2R3SioUZXRtRSs
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/558,513 US9034960B2 (en) | 2012-07-26 | 2012-07-26 | Antidrift composition |
NZ70364212 | 2012-09-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ720940A true NZ720940A (en) | 2018-07-27 |
Family
ID=62947686
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ720940A NZ720940A (en) | 2012-07-26 | 2012-09-12 | Antidrift composition |
Country Status (1)
Country | Link |
---|---|
NZ (1) | NZ720940A (en) |
-
2012
- 2012-09-12 NZ NZ720940A patent/NZ720940A/en unknown
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