IP Library Granted Patent US 6,887,830
Granted Patent B2
US 6,887,830 · App. 10/175,535 · Granted May 3, 2005

Surfactant adjuvants useful in herbicide compositions

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Quick Facts
Patent No.
US 6,887,830
App. No.
10/175,535
Granted
May 3, 2005
Kind
B2
Abstract

Surfactant adjuvants that improve the bioefficacy of herbicides by combining known surfactancy, or wetting characteristics, of sulfosuccinate or sulfosuccinamate-based surfactants, with the proven bioefficiacy characteristics of alkoxylated amine-based surfactants. The surfactant adjuvants contain an amine-based surfactant, and a sulfosuccinate or sulfosuccinamate-based surfactant. The surfactant adjuvants are combined with herbicidal active ingredients, and optionally, one or more formulation aids to form herbicide compositions that have a reduced tendency to cause eye and skin irritation and can be used to control unwanted weeds or vegetation.

Claims (46)

1. A herbicide composition that comprises:

a. a herbicidally effective amount of a herbicidal active ingredient; and

b. a surfactant component comprising an amine-based surfactant and a sulfosuccinate or sulfosuccinamate-based surfactant, wherein the surfactant component is present in an amount sufficient to enhance the effectiveness of the herbicidal active ingredient, and wherein the sulfosuccinate-based surfactant comprises a sulfosuccinate with the following general structure:

a mixture of (a) and (b);

where R 1 is hydrogen, or a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group with from zero to about thirty carbon atoms; R 2 is an alkylene group with from about two to about six carbon atoms, or a mixture thereof; R 3 , R 4 , and R 5 are each independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the same or different and may vary from zero to about sixty,

and wherein the sulfosuccinamate-based surfactant comprises a sulfosuccinamate with following general structure:

a mixture of (a) and (b);

where R 1 is a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group or mixtures thereof with from about one to about thirty carbon atoms; R 2 is either an alkylene group with from about two to about six carbon atoms, or a saturated or unsaturated alkyl, aryl, or alkylaryl group with from about one to about thirty carbon atoms; R 3 , R 4 , and R 5 are each independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the is the same or different and may vary from zero to about sixty.

2. The composition of claim 1 , wherein the amine-based surfactant comprises an alkoxylated amine surfactant.

3. The composition of claim 2 , wherein the alkoxylated amine surfactant is selected from the group consisting of polyoxyalkyleneamines, polyalkoxylate polyamines, cocoamine alkoxylates, tallow amine alkoxylates, soya amine alkoxylates, synthetic alkoxylated amines derived from primary alcohols, alkydiamine alkoxylates, etheramine alkoxylates, alkyletheramines, alkyletheramine alkoxylates, the methyl and ethyl quaternary ammonium salts thereof, and the amine oxides thereof.

4. The composition of claim 1 , wherein the herbicidal active ingredient comprises glyphosate or a salt thereof.

5. The composition of claim 1 , wherein the surfactant component further comprises water and a formulation aid.

6. The composition of claim 5 , wherein the formulation aid is selected from the group consisting of glycols, anti-freeze agents, dyes, thickening agents, anti-foaming agents, UV stabilizers, pH adjusting agents, and mixtures thereof.

7. The composition of claim 6 , wherein the composition has a reduced tendency to cause eye and skin irritation.

8. A herbicide composition that comprises:

a. a herbicidally effective amount of glyphosate or a salt thereof; and

b. a surfactant component comprising an amine-based surfactant, and a sulfosuccinate or sulfosuccinamate-based surfactant, wherein the surfactant component is present in an amount sufficient to enhance the effectiveness of the herbicidal active ingredient, and wherein the sulfosuccinate-based surfactant comprises a sulfosuccinate with following general structure:

a mixture of (a) and (b);

where R 1 is hydrogen, or a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group or mixtures thereof with from zero to about thirty carbon atoms; R 2 is an alkylene group with from about two to about six carbon atoms, or a mixture thereof; R 3 , R 4 , and R 5 are independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the same of different and may vary from 0 to 60, and wherein the sulfosuccinamate-based surfactant comprises a sulfosuccinamate with following general structure:

a mixture of (a) and (b);

where R 1 is a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group or mixtures thereof with from about one to about thirty carbon atoms; R 2 is either an alkylene group with from about two to about six carbon atoms, or a saturated or unsaturated alkyl, aryl, or alkylaryl group with from about one to about thirty carbon atoms; R 3 , R 4 , and R 5 are each independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the same or different and may vary from zero to about sixty.

9. The composition of claim 8 , wherein the amine-based surfactant comprises an alkoxylated amine surfactant.

10. The composition of claim 9 , wherein the alkoxylated amine surfactant is selected from the group consisting of polyoxyalkyleneamines, polyalkoxylate polyamines, cocoamine alkoxylates, tallow amine alkoxylates, soya amine alkoxylates, synthetic alkoxylated amines derived from primary alcohols, alkydiamine alkoxylates, etheramine alkoxylates, alkyletheramines, alkyletheramine alkoxylates, the methyl and ethyl quaternary ammonium salts thereof, and the amine oxides thereof.

11. The composition of claim 8 , wherein the surfactant component further comprises water and a formulation aid.

12. The composition of claim 11 , wherein the formulation aid is selected from the group consisting of anti-freeze agents, dyes, thickening agents, anti-foaming agents, pH adjusting agents, and mixtures thereof.

13. The composition of claim 8 , wherein from about 25% to about 45% by mass of the surfactant component comprises the sulfosuccinate or sulfosuccinamate-based surfactant.

14. The composition of claim 8 , wherein from about 45% to about 60% by mass of the surfactant component comprises the amine-based surfactant.

15. The composition of claim 8 , wherein from about 5% to about 20% by mass of the surfactant component comprises water and a formulation aid.

16. The composition of claim 8 , wherein the composition has a reduced tendency to cause eye and skin irritation.

17. A method of killing or controlling weeds or unwanted vegetation comprising the step of applying a herbicidally effective amount of the composition of claim 1 to the foliage or tissue of the weeds or unwanted vegetation.

18. A method of killing or controlling weeds or unwanted vegetation comprising the step of applying a herbicidally effective amount of the composition of claim 8 to the foliage or tissue of the weeds or unwanted vegetation.

19. A method of preparing a herbicidally effective composition comprising the steps of:

a. blending a surfactant component comprising an amine-based surfactant and a sulfosuccinate or sulfosuccinamate-based surfactant, wherein the sulfosuccinate-based surfactant comprises a sulfosuccinate with following general structure:

a mixture of (a) and (b);

where R, is hydrogen, or a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group or mixtures thereof with from zero to about thirty carbon atoms; R 2 is an alkylene group with from about two to about six carbon atoms, or a mixture thereof; R 3 , R 4 , and R 5 are each independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the same or different and may vary from zero to about sixty, and wherein the sulfosuccinamate-based surfactant comprises a sulfosuccinamate with following general structure:

a mixture of (a) and (b);

where R 1 is a straight or branched chain, unsaturated or saturated alkyl, aryl, or alkylaryl group or mixtures thereof with from about one to about thirty carbon atoms; R 2 is either an alkylene group with from about two to about six carbon atoms, or a saturated or unsaturated alkyl, aryl, or alkylaryl group with from about one to about thirty carbon atoms; R 3 , R 4 , and R 5 are each independently hydrogen, or a straight or branched chain, unsaturated or saturated alkyl or alkyloxy group with from zero to about twenty-five carbon atoms; and, x is the same or different and may vary from zero to about sixty; and

b. mixing a sufficient amount of the surfactant component with a herbicidal active ingredient to enhance the effectiveness of the herbicidal active ingredient.

20. The method of claim 19 , wherein the amine-based surfactant comprises an alkoxylated amine surfactant.

21. The method of claim 19 , wherein the alkoxylated amine surfactant is selected from the group consisting of polyoxyalkyleneamines, polyalkoxylate polyamines, cocoamine alkoxylates, tallow amine alkoxylates, soya amine alkoxylates, synthetic alkoxylated amines derived from primary alcohols, alkydiamine alkoxylates, etheramine alkoxylates, alkyletheramines, alkyletheramine alkoxylates, the methyl and ethyl quaternary ammonium salts thereof, and the amine oxides thereof.

22. The method of claim 19 , wherein the herbicidal active ingredient comprises glyphosate or a salt thereof.

23. The method of claim 19 , wherein the surfactant component further comprises water and a formulation aid.

24. The method of claim 23 , wherein the formulation aid is selected from the group consisting of glycols, anti-freeze agents, dyes, thickening agents, anti-foaming agents, UV stabilizers, pH adjusting agents, and mixtures thereof.

25. A method of preparing a composition, comprising the steps of:

a. blending a surfactant component comprising an amine-based surfactant and a sulfosuccinate or sulfosuccinamate-based surfactant, and

b. mixing a sufficient amount of the surfactant component with a herbicidal active ingredient to enhance the effectiveness of the herbicidal active ingredient, wherein a herbicidally effective composition having a reduced tendency to cause eye and skin irritation is produced.

Assignments (10)
ENTITY CONVERSION Recorded Jul 1, 2020
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 053532/0371 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2020
From: HUNTSMAN PETROCHEMICAL LLC
To: INDORAMA VENTURES OXIDES LLC
Reel/Frame 051649/0173 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN UNITED STATES TRADEMARKS AND PATENTS Recorded Jun 13, 2018
From: JPMORGAN CHASE BANK, N.A.
To: HUNTSMAN PETROCHEMICAL CORPORATION (N/K/A HUNTSMAN PETROCHEMICAL LLC)
Reel/Frame 046356/0616 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM AN ASSIGNMENT TO A SECURITY AGREEMENT PREVIOUSLY RECORDED ON REEL 025857 FRAME 0137. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 026515/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 025857/0137 →
RELEASE OF SECURITY INTEREST Recorded Feb 8, 2011
From: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT (F/K/A BANKERS TRUST COMPANY, AS COLLATERAL AGENT)
To: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN ETHYLEMEAMINES LLC; HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 025765/0853 →
SECURITY INTEREST Recorded Nov 17, 2005
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 016987/0496 →
SECURITY AGREEMENT Recorded Jan 28, 2005
From: HUNSTMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS AGENT
Reel/Frame 015661/0547 →
GRANT OF SECURITY INTEREST IN U.S. TRADEMARKS AND PATENTS Recorded Dec 4, 2003
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS (FORMERLY KNOWN AS BANKER TRUST COMPANY), AS COLLATERAL AGENT
Reel/Frame 014782/0186 →
SECURITY INTEREST Recorded Oct 15, 2002
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS (FORMERLY KNOWN AS BANKERS TRUST COMPANY), AS AGENT
Reel/Frame 013362/0237 →