IP Library › Granted Patent US 9,034,960
Granted Patent B2
US 9,034,960 · App. 13/558,513 · Granted May 19, 2015

Antidrift composition

Inventors: William L. Brown (Pleasantville, NY); George A. Policello (Ossining, NY)
Assignee: Momentive Performance Materials Inc.
A01N57/20C08L33/26C08K5/544
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Quick Facts
Patent No.
US 9,034,960
App. No.
13/558,513
Filed
Jul 26, 2012
Granted
May 19, 2015
Kind
B2
Art Unit
1762
USPC
524/188
Abstract

A solid, water-soluble fast-dissolving antidrift composition includes a urea-based complex-forming component (i) complexed with an antidrift component (ii), the antidrift composition optionally further including an adjuvant component (iii).

Claims (120)

1. A solid, water-soluble, fast-dissolving antidrift composition which comprises a urea-based complex-forming component (i) complexed with at least a portion of an antidrif component (ii), and as adjuvant component (iii) a superspreader surfactant with all, some or none of the superspreader surfactant being complexed with urea-based complex-forming component (i).

2. The antidrift composition of claim 1 wherein the superspreader surfactant is at least one organosilicon surfactant selected from the group consisting of polysiloxane alkoxylate surfactant (I), hydrolysis-resistant carbosilance surfactannt (IV), hydrolysis-resistant disiloxane surfactant (VII), first hydrolysis-resistant trisiloxane surfactant (IX), second hydrolysis-resistant trisiloxane surfactant (XI) and third hydrolysis-resistant trisiloxane (XIV) as hereinafter defined:

polysiloxane alkoxylate surfactant of general formula (I):

(R 1 R 2 R 3 SiO 1/2 )(R 4 R 5 SiO 2/2 ) n (R 6 R 10 SiO 2/2 ) p (R 7 R 8 R 9 SiO 1/2 )  (I)

wherein n is 0 or 1; p is 1 or 2; R 1 to R 8 are methyl; R 9 is methyl or, when R 10 is methyl, R 9 is R 11 ; R 10 is methyl or R 11 with R 11 being a polyalkylene oxide group of general formula (II):

R 13 (C 2 H 4 O) w (C 3 H 6 O) x (C 4 H 8 O) y R 12   (II)

in which w, x and y are independently an integer from 0 to 20, with the proviso that w is greater than or equal to 2 and w+x+y is in a range of from 2 to 20; R 2 is a hydrogen atom, an aliphatic radical or an acetyl group; and, R 13 is a divalent aliphatic radical having the structure (III):

—CH 2 CH(R 14 )(R 15 ) z O—  (III)

in which R 14 is a hydrogen atom or an aliphatic radical, R 15 is a divalent aliphatic radical of 1 to 6 carbon atoms and z is 0 or 1;

hydrolysisis-resistant carbosilane surfactants of general formula (IV):

(R 16 )(R 17 )(R 18 )Si—R 19 —Si(R 20 )(R 21 )(R 22 )   (IV)

wherein R 16 , R 17 , R 18 , R 20 and R 21 are each independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl and a hydrocarbon group of 7 to 10 carbon atoms containing an aryl group; R 19 is a divalent hydrocarbon group of 1 to 3 carbons; R 22 is a polyalkylene oxide group of general formula (V):

R 23 (C 2 H 4 O) d (C 3 H 6 O) e (C 4 H 8 O) f R 24   (V)

in which R 23 is a divalent linear or branched hydrocarbon radical having structure (VI):

—CH 2 CH(R 25 )(R 26 ) g O—  (VI)

in which R 25 is hydrogen or methyl; R 26 is a divalent alkyl radical of 1 to 6 carbon atoms where the subscript g may be 0 or 1; R 24 is selected from the group consisting of hydrogen, monovalent hydrocarbon radical of 1 to 6 carbon atoms and acetyl, subject to the limitation that subscripts d, e and f are zero or positive and satisfy the following relationships:

2 ≦d+e+f≦ 20 with d≧ 2;

hydrolysis-resistant disiloxane surfactants of general formula (VII):

MM′  (VII)

wherein M is R 27 R 28 R 29 SiO 1/2 and M′ is R 30 R 31 R 32 SiO 1/2 in which R 27 is selected from the group consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms or R 33 in which R 33 is selected from the group consisting of R 34 R 35 R 36 SiR 37 and (R 30 R 31 R 32 )SiR 37 ) in which R 34 , R 35 and R 36 each independently is selected from the group consisting of monovalent hydrocarbon radical of from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon radical of from 6 to 13 carbon atoms and R 37 is a divalent hydrocarbon radical of from 1 to 3carbon atoms; R 28 and R 29 each independently is selected from the group consisting of monovalent hydrocarbon radical of from 1 to 6 carbon atoms or R 27 , and R 30 is a polyalkylenc oxide group selected from the group consisting of R 38 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 39 and

R 37 SiR 31 R 32 (R 38 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 39 ) in which R 38 is a divalent linear or branched hydrocarbon radical having the structure (VIII):

—CH 2 CH(R 40 )(R 41 ) d O—  (VIII)

in which R 40 is hydrogen or methyl; R 41 is a divalent alkyl radical of 1 to 6 carbon atoms in which subscript d may be 0 or 1; R 39 is selected from the group consisting of hydrogen, monovalent hydrocarbon 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 following relationships:

2 ≦a+b+c≦ 20 with a≧ 2,

and R 31 and R 32 each independently is selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 30 ;

first hydrolysis-resistant trisiloxane of general formula (IX):

M 1 D 1 M 2   (IX)

wherein M 1 is (R 42 )(R 43 )(R 44 )SiO 1/2 ,M 2 is (R 45 )(R 46 )(R 47 )SiO 1/2 and D 1 is (R 48 )(Z)SiO 2/2 in which R 42 is selected from a branched or linear hydrocarbon group of from 2 to 4 carbon atoms, aryl and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituent of 6 to 20 carbon atoms; R 43 , R 44 , R 45 ,R 46 , R 47 and R 48 each independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms and hydrocarbon radical of 4 to 9 carbons containing an aryl group of from 6 to 20 carbon atoms, and Z is an alkyleneoxide group of general formula (X):

R 49 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 50   (X)

in which R 49 is a linear or branched divalent hydrocarbon radical of 2, 3, 5, 6, 7, 8 or 9 carbon atoms; R 50 is selected from the group consisting of hydrogen, monovalent hydrocarbon radicals 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 relationships:

2 ≦a+b+c≦ 20 with a≧ 2;

second hydrolysis-resistant trisiloxane of general formula (XI):

M 3 D 2 M 4   (XI)

wherein M 3 is (R 51 )(R 52 )(R 53 )SiO 1/2 , M 4 is R 54 )(R 55 )(R 56 )SiO 1/2 and D 2 is (R 57 )(Z′)SiO 2/2 in which R 51 , R 52 , R 53 ,R 54 , R 55 , R 56 and R 57 each independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms, aryl and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituents of 6 to 20 carbon atoms; Z′ is a polyalkylene oxide group of general formula (XII):

R 58 (C 2 H 4 O) d (C 3 H 6 O) e (C 4 H 8 O) f R 59   (XII)

in which R 58 is selected from a branched or linear divalent hydrocarbon radical of the general formula (XIII):

—C 4 H 8 O(C 2 H 4 O)—  (XIII)

in which R 59 is selected from the group consisting of hydrogen, monovalent hydrocarbon radical 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 d≧ 2; and,

third hydrolysis-resistant trisiloxane of general formula (XIV):

M 5 D 3 M 6   (XIV)

wherein M 5 is (R 60 )(R 61 )(R 62 )SiO 1/2 , M 6 is (R 63 )(R 64 )(R 65 )SiO 1/2 and D 3 is (R 66 )(Z″)SiO 2/2 in which R 60 , R 61 , R 62 , R 63 , R 64 and R 65 each independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms, aryl, and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituent of 6 to 20 carbon atoms, R 66 is a linear or branched hydrocarbon radical of 2 to 4 carbons; Z″ is a polyalkylene oxide group of general formula (XV):

R 67 (C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 68   (XV)

wherein R 67 is a linear or branched divalent hydrocarbon radical of 2, 3, 5, 6, 7, 8, or 9 carbon atoms; R 68 is selected from the group consisting 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 positive and satisfy the following relationships:

2 ≦g+h+i≦ 20 with g≧ 2.

3. The antidrift composition of claim 1 further comprising at least one adjuvant component (iii) selected from the group consisting of organosilicon superspreader surfactant, non-organosilicon superspreader surfactant, non-superspreading organosilicon surfactant, non-superspreading, non-organosilicon surfactant, antifoam additive, anticaking/free flow additive, sticker and dye.

4. The antidriti composition of claim 1 further comprising as adjuvant component (iii) at least one mixture of surfactants selected from the group consisting of organosilicon superspreader surfactant and non-organosilicon superspreader surfactant; organosilicon superspreader surfactant and non-superspreading organosilicon surfactant; organosilicon superspreader surfactant and non-superspreading, non-organosilicon surfactant; non-organosilicon superspreader surfactant and non-superspreading organosilicon surfactant; non-organosilicon superspreader surfactant and non-superspreading, non-organosilicon surfactant; and, non-superspreading organosilicon surfactant and non-superspreading, non-organosilicon surfactant, with all, some or none of a mixture, or a surfactant component of a mixture, being complexed with urea-based complex-forming component (i).

5. The antidrift composition of claim 4 wherein the non-organosilicon surthetant is of general formula (XVI):

wherein R 69 is the same or different and is selected from the group consisting of hydrogen and an alkyl of 1 to 4 carbon atoms; c is 5 to 9, d is 0 to 4, c+d is 5 to 9 and t is 0 or 1; R 70 is a nonionic hydrophilic moiety with the proviso that when t is 0, R 70 is

and when t is 1, R 70 is selected from the group consisting of (i) [C 2 H 4 O] f [C 3 H 6 O] g H and (ii) (C 6 H 9 O 5 ) h —C 6 H 10 O 5 in which f is 1 to 40, g is 0 to 40 and h is 1 to 4.

6. The antidrill composition of claim 5 wherein the non-organosilicon surfactant is admixed with an organosilicon superspreader surfactant and/or non-organosilicon superspreader surfactant.

7. A solid, water-soluble, fast-dissolving antidrift composition which comprises a urea-based complex-forming component (i) which is at least one member selected from the group consisting of urea, thiourea, urea formaldehyde, urea hydrate, urea phosphate and urea sulfate complexed with an antidrift component (ii) which is at least one member selected from the group consisting of guar, guar derivative, xantham gum, polyacrylamide homopolymer and polyacrylamide copolymer, the antidrift composition optionally including at least one adjuvant component (iii) selected from the group consisting of organosilicon superspreader surfactant, non-organosilicon superspreader surfactant, non-superspreading organosilicon surfactant, non-superspreading, non-organosilicon surfactant, antifoam additive, anticakingifree flow additive, sticker and dye.

8. The antidrift composition of claim 7 further complexed with, as adjuvant component (iii), an organosilicon superspreader surfactant selected from the group consisting of polysiloxane alkoxylate surfactant (I), hydrolysis-resistant carbosilane surfactant (IV), hydrolysis-resistant disiloxane surfactant (VII), first hydrolysis-resistant trisiloxane surfactant (IX), second hydrolysis-resistant trisiloxane surfactant (XI) and third hydrolysis-resistant trisiloxane (XIV) as hereinafter defined:

polysiloxane alkoxylate surfactant of general formula (I):

(R 1 R 2 R 3 SiO 1/2 )(R 4 R 5 SiO 2/2 ) n (R 6 R 10 SiO 2/2 ) p (R 7 R 8 R 9 SiO 1/2 )  (I)

wherein n is 0 or 1; p is 1 or 2; R 1 to R 8 are methyl; R 9 is methyl or, when R 10 is methyl, R 9 is R 11 ; R 10 is methyl or R 11 with R 11 being a polyalkylene oxide group of general formula (II):

R 13 (C 2 H 4 O) w (C 3 H 6 O) x (C 4 H 8 O) y R 12   (II)

in which w, x and y are independently an integer from 0 to 20, with the proviso that w is greater than or equal to 2 and w+x+y is in a range of from 2 to 20; R 12 is a hydrogen atom, an aliphatic radical or an acetyl group; and, R 13 is a divalent aliphatic radical having the structure(III):

—CH 2 CH(R 14 )(R 15 ) z O—  (III)

in which R 14 is a hydrogen atom or an aliphatic radical, R 15 is a divalent aliphatic radical of 1 to 6 carbon atoms and z is 0 or 1;

hydrolysisis-resistant carbosilane surfactants of general formula (IV):

(R 16 )(R 17 )(R 18 )Si—R 19 —Si(R 20 )(R 2 )(R 22 )   (IV)

wherein R 16 , R 17 , R 18 , R 20 and R 21 are each independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl and a hydrocarbon group of 7 to 10 carbon atoms containing an aryl group; R 19 is a divalent hydrocarbon group of 1 to 3 carbons; R 22 is a polyalkvlene oxide group of general formula (V):

R 23 (C 2 H 4 O) d (C 3 H 6 O) e (C 4 H 8 O) f R 24   (V)

in which R 23 is a divalent linear or branched hydrocarbon radical having structure (VI):

—CH 2 CH(R 25 )(R 26 ) g O—  (VI)

in which R 25 is hydrogen or methyl; R 26 is a divalent alkyl radical of 1 to 6 carbon atoms where the subscript g may be 0 or 1; R 24 is selected from the group consisting of hydrogen, monovalent hydrocarbon radical of 1 to 6 carbon atoms and acetyl, subject to the limitation that subscripts d, e and f are zero or positive and satisfy the following relationships:

2 ≦d+e+f≦ 20 with d≧ 2;

hydrolysis-resistant disiloxane surfactants of general formula (VII):

MM′   (VII)

wherein M is R 27 R 28 R 29 SiO 1/2 and M′ is R 30 R 31 R 32 SiO 1/2 in which R 27 is selected from the group consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms or R 33 in which R 33 is selected from the group consisting of R 34 R 35 R 36 SiR 37 and (R 30 R 31 R 32 )SiR 37 ) in which R 34 , R 35 and R 36 each independently is selected from the group consisting of monovalent hydrocarbon radical of from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon radical of from 6 to 13 carbon atoms and R 37 is a divalent hydrocarbon radical of from 1 to 3 carbon atoms; R 28 and R 29 each independently is selected from the group consisting of monovalent hydrocarbon radical of from 1 to 6 carbon atoms or R 27 , and R 30 is a polyalkylene oxide group selected from the group consisting of R 38 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 39 and

R 37 SiR 31 R 32 (R 38 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 39 ) in which R 38 is a divalent linear or branched hydrocarbon radical having the structure (VIII):

—CH 2 CH(R 40 )(R 41 ) d O—tm (VIII)

in which R 40 is hydrogen or methyl; R 41 is a divalent alkyl radical of 1 to 6 carbon atoms in which subscript d may be 0 or 1; R 39 is selected from the group consisting of hydrogen, monovalent hydrocarbon 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 following relationships:

2≦ a+b+c≦ 20 with a≧2,

and R 31 and R 32 each independently is selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 30 ;

first hydrolysis-resistant trisiloxane of general formula (IX):

M 1 D 1 M 2   (IX)

wherein M 1 is (R 42 )(R 43 )(R 44 )SiO 1/2 , M 2 is (R 45 )(R 46 )(R 47 )SiO 1/2 and D 1 is (R 48 )(Z)SiO 2/2 in which R 42 is selected from a branched or linear hydrocarbon group of from 2 to 4 carbon atoms, aryl and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituent of 6 to 20 carbon atoms; R 43 , R 44 , R 45 , R 46 , R 47 and R 48 each independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms and hydrocarbon radical of 4 to 9 carbons containing an aryl group of from 6 to 20 carbon atoms, and Z is an alkyleneoxide group of general formula (X):

R 49 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 50   (X)

in which R 49 is a linear or branched divalent hydrocarbon radical of 2, 3, 5, 6, 7, 8 or 9 carbon atoms; R 50 is selected from the group consisting of hydrogen, monovalent hydrocarbon radicals 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 relationships:

2 ≦a+b+c≦ 20 with a≧ 2;

second hydrolysis-resistant trisiloxane of general formula (XI):

M 3 D 2 M 4   (XI)

wherein M 3 is (R 51 )(R 52 )(R 53 )SiO 1/2 , M 4 is (R 54 )(R 55 )(R 56 )SiO 1/2 and D 2 is (R 57 )(Z′)SiO 2/2 in which R 51 , R 52 , R 53 , R 54 , R 55 , R 56 and R 57 each independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms, aryl and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituents of 6 to 20 carbon atoms; Z′ is a polyalkylene oxide group of general formula (XII):

R 58 (C 2 H 4 O) d (C 3 H 6 O) e (C 4 H 8 O) f R 59   (XII)

in which R 58 is selected from a branched or linear divalent hydrocarbon radical of the general formula (XIII):

—C 4 H 8 O(C 2 H 4 O)—  (XIII)

in which R 59 is selected from the group consisting of hydrogen, monovalent hydrocarbon radical 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 d≧ 2; and,

third hydrolysis-resistant trisiloxanc of general formula (XIV):

M 5 D 3 M 6   (XIV)

wherein M 5 is (R 60 )(R 61 )(R 62 )SiO 1/2 , M 6 is (R 63 )(R 64 )(R 65 )SiO 1/2 and D 3 is (R 66 )(Z″)SiO 2/2 in which R 60 , R 61 , R 62 , R 63 , R 64 and R 65 independently is selected from the group consisting of monovalent hydrocarbon radical of 1 to 4 carbon atoms, aryl, and alkyl hydrocarbon group of 4 to 9 carbon atoms containing an aryl substituent of 6 to 20 carbon atoms, R 66 is a linear or branched hydrocarbon radical of 2 to 4 carbons; Z″ is a polyalkylene oxide group of general formula (XV):

R 67 (C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 68   (XV)

wherein R 67 is a linear or branched divalent hydrocarbon radical of 2, 3, 5, 6, 7, 8, or 9 carbon atoms; R 68 is selected from the group consisting 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 positive and satisfy the following relationships:

2 ≦g+h+i≦ 20 with g≧ 2.

9. The antidrift composition of claim 8 further comprising as adjuvant component (iii) a non-organosilicon surfactant of general formula (XVI):

wherein R 69 is the same or different and is selected from the group consisting of hydrogen and an alkyl of from 1 to 4 carbon atoms; c is 5 to 9, d is 0 to 4, c+d is 5 to 9 and t is 0 or 1; R 70 is a nonionic hydrophilic moiety with the proviso that when t is 0, R 70 is

and when t is 1, R 70 is selected from the group consisting of (i) [C 2 H 4 O] f [C 3 H 6 O] g H and (ii) (C 6 H 9 O 5 ) h —C 6 H 10 O 5 , in which f is 1 to 40, g is 0 to 40 and h is 1 to 4.

10. The antidrift composition of claim 7 wherein at least 50 weight percent of antidrift component (ii) is complexed with urea-based complex-forming component (i), the antidrift composition comprising 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:

Weight Parts Ranges A, B and C

Component

A

B

C

(i)

 55-99.9

70-95

80-98

(ii)

0.1-25  

0.5-10 

1-5

(iii)

0-20

 1-20

 1-15.

11. A process for producing the solid, water-soluble, fast-dissolving antidrift composition of claim 1 which comprises forming a complex of urea-based complex-forming component (i) and antidrift component (ii), the resulting fast-dissolving antidrift composition in particulate form exhibiting a dissolution time in aqueous medium that is at least 30% less than that of an equivalent amount of non-complexed urea-based complex-thrilling component (i) and antidrift component (ii) of comparable particulate form under substantially identical dissolution conditions.

12. The process of claim 11 wherein the resulting fast-dissolving antidrift composition exhibits a dissolution time in aqueous medium that is at least 50% less than that of an equivalent amount of non-complexed urea-based complex-forming component (i) and antidrift component (ii) of comparable particulate form under substantially identical dissolution conditions.

13. The process of claim 11 wherein the resulting fast-dissolving antidrift composition exhibits a dissolution time in aqueous medium that is at least 70% less than that of an equivalent amount of non-complexed urea-based complex-forming component (i) and antidrift component (ii) of comparable particulate form under substantially identical dissolution conditions.

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Continuity (1)
Related Publication 20140031467A1 · Jan 30, 2014