IP Library Granted Patent US 9,012,365
Granted Patent B2
US 9,012,365 · App. 12/518,029 · Granted Apr 21, 2015

Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts

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Quick Facts
Patent No.
US 9,012,365
App. No.
12/518,029
Granted
Apr 21, 2015
Kind
B2
Abstract

The present invention generally relates to a method for minimizing the formation of insoluble salts of phenoxy herbicides. The method comprises (1) mixing a compatibility agent, amine salts of phenoxy acid herbicides, and a chemical containing non-amine cations in a aqueous system to form a stable and non-nozzle plugging solution; and (2) application of said stable and non-nozzle plugging solution onto target plants.

Claims (129)

1. A herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide, (b) non-amine cations, and (c) at least one compatibility agent in an amount effective to prevent the formation of insoluble salts of said phenoxy acid herbicide,

wherein said compatibility agent comprises a substance selected from the group consisting of alkoxylated quaternary surfactant, alkyl quaternary surfactant, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil alkoxylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide and combinations thereof,

wherein the ratio of said at least one amine salt of a phenoxy acid herbicide to said compatibility agent is from 20:1 to 1:2 by weight, and

wherein said herbicidal formulation does not comprise glyphosate.

2. The formulation of claim 1 wherein said phenoxy acid herbicide is selected from the group consisting of a phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and combinations thereof.

3. The formulation of claim 1 wherein said compatibility agent is

i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and A is C i H 2i where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion, f is zero to 10; m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; A is C i H 2i , where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion; f is zero to 10; p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a provision that p is greater than q;

iii. an amidoamine of the formula:

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

iv. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i , where i is 2 to 4; n, m, p, and q all is 1 to 20 independently; x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1;

v. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms; A is C i H 2i , where i is 2 to 4; m is 1 to 30, and n is 1 to 30;

vi. tristyrylphenol ethoxylate with 8 -30 EO and its phosphate or salts thereof;

vii. EO/PO block and random copolymer of the formula,

R1 OA′) x H

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′ is C2 or C3, x is 30 to 300, EO:PO >40:60 (weight ratio);

viii. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

ix. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

x. Hydroxides of sodium, potassium, ammonium and mixtures thereof; or

xi. mixtures thereof.

4. The formulation of claim 3 wherein said compatibility agent is selected from the group consisting of tallowamine 2-15EO methylchloride quaternary, cocoamine 2-15EO methylchloride quaternary, cocotrimethyl quaternary ammonium chloride, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tall oil and diethylenetriamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyryrphenol +13-20EO, C4 with average 52EO and 42PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulfonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate-36 EO, coco duoamine-3EO, and mixtures thereof.

5. The formulation of claim 3 wherein the phenoxy acid herbicide is 2,4-D.

6. The formulation of claim 5 wherein the ratio of 2,4-D amine salt to the compatibility agent is from 10:1 to 1:1.5 by weight.

7. The formulation of claim 5 wherein the ratio of 2,4-D amine salt to the compatibility agent is from 5:1 to 1:1 by weight.

8. The formulation of claim 5 wherein the concentration of 2,4-D amine salt is from 0.1 to 40% by weight, based on the weight of the formulation.

9. The formulation of claim 5 wherein the concentration of 2,4-D amine salt is from 1 to 30% by weight, based on the weight of the formulation.

10. The formulation of claim 5 wherein the concentration of 2,4-D amine salt is from 2 to 20% by weight, based on the weight of the formulation.

11. A method for improving the compatibility of an amine salt of phenoxy acid herbicide with non-amine cations in a herbicidal formulation, said method comprising adding at least one compatibility agent to a herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide and (b) non-amine cations, wherein the at least one compatibility agent is added to said formulation in a sufficient amount to improve the compatibility of said amine salt of said phenoxy acid herbicide with said non-amine cations,

wherein said compatibility agent comprises at least one alkoxylate quaternary surfactant, alkyl quaternary surfactant, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil ethoxylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide or combinations thereof,

wherein the ratio of said at least one amine salt of a phenoxy acid herbicide to said compatibility agent is from 20:1 to 1:2 by weight, and

wherein the herbicidal formulation does not comprise glyphosate.

12. The method of claim 11 wherein said herbicide is selected from the group consisting of a phenoxy acid herbicide of phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and mixtures thereof.

13. The method of claim 11 wherein said compatibility agent is

i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and A is C i H 2i where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion, f is zero to 10; m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; A is C i H 2i , where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion; f is zero to 10; p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

iii. an amidoamine of the formula:

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

iv. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i , where i is 2 to 4; n, m, p, and q all are 1 to 20 independently; x and y is 0 to 5 independently with a proviso that x+y are greater than or equal to 1;

v. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms; A is C i H 2i where i is 2 to 4; m is 1 to 30, and n is 1 to 30;

vi. tristyrylphenol ethoxylate with 8 - 30 moles ethoxylation and its phosphate or salts thereof;

vii. EO/PO block and/or random copolymer of the formula,

R1 OA′) x H

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′ is C2 or C3, x is 30 to 300, EO:PO>40:60 (weight ratio);

viii. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

ix. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

x. Hydroxides of sodium, potassium, ammonium and mixtures thereof; or

xi. mixtures thereof.

14. The method of claim 11 wherein said compatibility agent is selected from the group consisting of tallowamine 2-15EO methyl chloride quaternary, cocoamine 2-15 EO methylchloride quaternary, coco trimethly quaternary ammonium chloride, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyrylphenol +13-20EO, C4 with average of 52EO and 46PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulphonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate 36EO, coco duoamine-3EO, and mixtures thereof.

15. The method of claim 11 wherein the phenoxy acid herbicide is 2,4-D.

16. The method of claim 15 wherein the ratio of 2,4-D amine salt to the compatibility agent is from 10:1 to 1:1.5 by weight, based on the weight of the formulation.

17. The method of claim 15 wherein the concentration of 2,4-D amine salt is from 0.1 to 40% by weight, based on the weight of the formulation.

18. The formulation of claim 3 wherein in formula i) , A is C 2 H 4 , f =0, g =0, m +n is 2 to 20, R2 is methyl group, p =1, and X is chloride.

19. The formulation of claim 3 wherein in formula ii) A is C 2 H 4 , f =0, g =0, R2 is methyl group, R3 is a methyl group, R4 is a methyl group, p =1, and X is chloride.

20. The formulation of claim 3 wherein in formula iv), R1 is derived from tall oil, coconut oil, soya oil, corn, and/or tallow.

21. The formulation of claim 3 wherein X − is a compatible i anion selected from the group consisting of methyl sulfate and chloride.

22. The formulation of claim 13 wherein X − is a compatible i anion selected from the group consisting of methyl sulfate and chloride.

23. The formulation of claim 1 wherein the non-amine cations are selected from the group consisting of ammonium, potassium, sodium, calcium, magnesium cations, and combination thereof.

24. The method of claim 11 wherein the non-amine cations are selected from the group consisting of ammonium, potassium, sodium, calcium, magnesium cations, and combination thereof.

25. A herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide, (b) non-amine cations, and (c) at least one compatibility agent in an amount effective to prevent the formation of insoluble salts of said phenoxy acid herbicide, wherein the ratio of said at least one amine salt of a phenoxy acid herbicide to said compatibility agent is from 20:1 to 1:2 by weight, with the proviso that the herbicidal formulation does not comprise phosphate esters or glyphosate.

26. The formulation of claim 25 wherein said phenoxy acid herbicide is selected from the group consisting of a phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and combinations thereof.

27. The formulation of claim 25 wherein said compatibility agent comprises a substance selected from the group consisting of alkoxylated quaternary surfactant, alkyl quaternary surfactant, alkoxylated amine, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil alkoxylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide and combinations thereof.

28. The formulation of claim 27 wherein said compatibility agent is

i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and A is C i H 2i where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion, f is zero to 10; m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; A is C i H 2i where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion; f is zero to 10; p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a provision that p is greater than q;

iii. an alkoxylated amine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; A is C i H 2i , where i is 2 to 4; and B is C j H 2j where j is 2 to 6; f is zero to 10; m and n is an integer of from 0-30 with the proviso that m+n is at least 1, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p;

iv. an amidoamine of the formula :

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

v. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i , where i is 2 to 4; n, m, p, and q all is 1 to 20 independently; x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1;

vi. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms; A is C i H 2i where i is 2 to 4; m is 1 to 30, and n is 1 to 30;

vii. tristyrylphenol ethoxylate with 8 -30 EO and its phosphate or salts thereof;

viii. EO/PO block and random copolymer of the formula,

R1 OA′) x H

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′ is C2 or C3, x is 30 to 300, EO:PO>40:60 (weight ratio);

ix. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

x. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

xi. Hydroxides of sodium, potassium, ammonium and mixtures thereof; or

xii. mixtures thereof.

29. The formulation of claim 28 wherein said compatibility agent is selected from the group consisting of tallowamine 2-15EO methylchloride quaternary, cocoamine 2-15EO methylchloride quaternary, cocotrimethyl quaternary ammonium chloride, cocoamine ethoxylate 2-20EO, tallowamine ethoxylate 2-20EO, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tall oil and diethylenetriamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyryrphenol +13-20EO, C4 with average 52EO and 42PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulfonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate-36 EO, coco duoamine-3EO, and mixtures thereof.

30. A method for improving the compatibility of an amine salt of phenoxy acid herbicide with non-amine cations in a herbicidal formulation, said method comprising adding at least one compatibility agent to a herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide and (b) non-amine cations, wherein the at least one compatibility agent is added to said formulation in a sufficient amount to improve the compatibility of said amine salt of said phenoxy acid herbicide with said non-amine cations, wherein the ratio of said at least one amine salt of a phenoxy acid herbicide to said compatibility agent is from 20:1 to 1:2 by weight, with the proviso that the compatibility agent does not comprise phosphate esters or glyphosate.

31. The method of claim 30 wherein said herbicide is selected from the group consisting of a phenoxy acid herbicide of phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and mixtures thereof.

32. The method of claim 30 wherein said compatibility agent comprises at least one alkoxylate quaternary surfactant, alkyl quaternary surfactant, alkoxylated amine, amidoamine, alkoxylate of the reaction product of fatty acid and polyamines, ethoxylate of the reaction product of fatty acid and triethanolamine, tristyrylphenol ethoxylate, EO-PO block or random copolymer, alkyl olefin sulfonate, alkylbenzenesulfonate amine salt, castor oil ethoxylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide or combinations thereof.

33. The method of claim 32 wherein said compatibility agent is i. an alkoxylated quaternary surfactant of the formula:

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2 is a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; and A is C i H 2i where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion, f is zero to 10; m and n is an integer of from 1-30 with the proviso that m+n is at least 2, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

ii. an alkyl quaternary surfactant of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; R2, R3, and R4 is independently a straight or branched chain, saturated or unsaturated alkyl group having from 1 to 4 carbon atoms; A is C i H 2i , where i is 2 to 4; B is C j H 2j where j is 2 to 6; and X − is a compatible anion; f is zero to 10; p is 1 to 7 and g is any number from zero to 6 for each p and independent of p, and q is 1 to 7 with a proviso that p is greater than q;

iii. an alkoxylated amine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 8 to 22 carbon atoms; A is C i H 2i where i is 2 to 4; and B is C j H 2j where j is 2 to 6; f is zero to 10; m and n is an integer of from 0-30 with the proviso that m+n is at least 1, p is 1 to 7 and g is any number from zero to 6 for each p and independent of p;

iv. an amidoamine of the formula :

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms;

v. Alkoxylated amido polyamines of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i where i is 2 to 4; n, m, p, and q all is 1 to 20 independently; x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1;

vi. the reaction products of fatty acid and triethanolamine and its alkoxylated products of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkylene group having from 8 to 22 carbon atoms; A is C i H 2i where i is 2 to 4; m is 1 to 30, and n is 1 to 30;

vii. tristyrylphenol ethoxylate with 8 -30 EO and its phosphate or salts thereof;

viii. EO/PO block and random copolymer of the formula,

R1 OA′) V H

wherein R1 is H, or C4 to C10 linear or branched alkyl, A′ is C2 or C3, x is 30 to 300, EO:PO>40:60 (weight ratio);

ix. alkyl olefin sulfonate having an alkyl chain length between C8 and C18 and salts thereof;

x. castor oil EO-PO alkoxylate having a total of 25 to 50 EO+PO units;

xi. Hydroxides of sodium, potassium, ammonium and mixtures thereof; or

xii. mixtures thereof.

34. The method of claim 33 wherein said compatibility agent is selected from the group consisting of tallowamine 2-15EO methyl chloride quaternary, cocoamine 2-15 EO methylchloride quaternary, coco trimethly quaternary ammonium chloride cocoamine ethoxylate 2-20EO, tallowamine ethoxylate 2-20EO, C13 etheramine-5EO, C8-C12 dimethylpropylamine, ethoxylate 10EO of the reaction product of tallow fatty acid with triethanolamine, tristyrylphenol +13-20EO, C4 with average of 52EO and 46PO, EO-PO-EO Block copolymer (50% EO) MW 4600, sodium lauryl olefin sulphonate, dodecylbenzene sulfonate isopropylamine salt, castor oil ethoxylate 36EO, coco duoamine-3EO, and mixtures thereof.

35. A herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide, (b) non-amine cations, and (c) at least one compatibility agent in an amount effective to prevent the formation of insoluble salts of said phenoxy acid herbicide, wherein the at least one compatibility agent is selected from the group consisting of amidoamines.

36. The formulation of claim 35 wherein said phenoxy acid herbicide is selected from the group consisting of a phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and combinations thereof.

37. The formulation of claim 35 wherein the compatibility agent is

iv. an amidoamine of the formula :

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; or

v. an alkoxylated amido polyamine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i where i is 2 to 4; n, m, p, and q all is 1 to 20 independently; x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1.

38. A method for improving the compatibility of an amine salt of phenoxy acid herbicide with non-amine cations in a herbicidal formulation, said method comprising adding at least one compatibility agent to a herbicidal formulation comprising (a) at least one amine salt of a phenoxy acid herbicide and (b) non-amine cations, wherein the at least one compatibility agent is selected from the group consisting of amidoamines, and wherein the at least one compatibility agent is added to said formulation in a sufficient amount to improve the compatibility of said amine salt of said phenoxy acid herbicide with said non-amine cations.

39. The method of claim 38 wherein said herbicide is selected from the group consisting of a phenoxy acid herbicide of phenoxyacetic herbicide, phenoxybutyric herbicide, phenoxypropionic herbicide, aryloxyphenoxypropionic herbicide, 4- CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 4-CPB, 2,4-DB, 3,4-DB, MCPB, cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, and mixtures thereof.

40. The method of claim 38 wherein the compatibility agent is

iv. an amidoamine of the formula:

where R1 a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; or

v. an alkoxylated amido polyamine of the formula

wherein R1 is a straight or branched chain, saturated or unsaturated alkyl group having from 7 to 21 carbon atoms; A is C i H 2i where i is 2 to 4; n, m, p, and q all is 1 to 20 independently; x and y is 0 to 5 independently with a provision of x+y greater than or equal to 1.

Assignments (4)
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2017
From: AKZO NOBEL N.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 044427/0759 →
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST INVENTOR'S NAME PREVIOUSLY RECORDED ON REEL 022921 FRAME 0846. ASSIGNOR(S) HEREBY CONFIRMS THE FROM SUN, JINIXIA SUSAN TO SUN, JINXIA SUSAN. Recorded Jul 22, 2009
From: SUN, JINXIA SUSAN; ZHU, SHAWN; KHAN, SHUAIB A.
To: AKZO NOBEL N.V.
Reel/Frame 022988/0293 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2009
From: SUN, JINIXIA SUSAN; ZHU, SHAWN; KHAN, SHUAIB A.
To: AKZO NOBEL N.V.
Reel/Frame 022921/0846 →