IP Library Granted Patent US 10,918,109
Granted Patent B2
US 10,918,109 · App. 15/714,243 · Granted Feb 16, 2021

Lecithin-based spray adjuvant containing organosilicon wetting agents

Inventors: George A. Policello (Ossining, NY); Jeferson A. Naue (Yorktown Heights, NY); Narayan Mukherjee (Hudson, NY)
Assignee: Momentive Performance Materials Inc.
A01N57/12A01N25/04A01N25/06A01N25/30A01N55/00C07F7/081C08G77/485C08G65/00C08G2650/34
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,918,109
App. No.
15/714,243
Granted
Feb 16, 2021
Kind
B2
Abstract

The present disclosure relates to an adjuvant composition comprising lecithin; and, an organosilicon surfactant of formula (I): R 1 —Si(CH 3 ) 2 —Z  (I) wherein: R 1 is a branched monovalent hydrocarbon group of from 5 to 8 carbon atoms containing at least two methyl groups; Z is R 2 or R 3 ; R 2 is CH 2 CH 2 CH 2 —O C 2 H 4 —O) a (C 3 H 6 O) b (C 4 H 8 O) c —R 4 in which R 4 is hydrogen, a linear or branched monovalent hydrocarbon group of from 1 to about 4 carbon atoms or an acyl group, subscript a is from 1 to about 20, subscript b is from 0 to about 19, subscript c is from 0 to about 19 and the sum of subscripts a, b and c is from 1 to about 20; and, R 3 is —CH 2 CH 2 CH 2 —O—CH(OH)CH 2 —N + (CH 3 ) 2 —R 5 [X − ] in which R 5 is a linear or branched hydrocarbon group of from 1 to about 4 carbon atoms or an acetyl group and X − is a saturated or unsaturated carboxylate anion of from 2 to about 22 carbon atoms optionally containing 1 or 2 hydroxyl groups.

Claims (99)

1. An adjuvant composition comprising:

a) lecithin; and,

b) an organosilicon surfactant of general formula (I):

R 1 —Si(CH 3 ) 2 —Z

wherein:

R 1 is a branched monovalent hydrocarbon group of from 5 to 8 carbon atoms containing at least two methyl groups;

Z is R 2 or R 3 ;

R 2 is CH 2 CH 2 CH 2 —O C 2 H 4 —O) a (C 3 H 6 O) b (C 4 H 8 O) c —R 4 in which R 4 is hydrogen, a linear or branched monovalent hydrocarbon group of from 1 to about 4 carbon atoms or an acyl group, subscript a is from 1 to about 20, subscript b is from 0 to about 19, subscript c is from 0 to about 19 and the sum of subscripts a, b and c is from 1 to about 20; and,

R 3 is —CH 2 CH 2 CH 2 O—CH(OH)CH 2 —N + (CH 3 ) 2 —R 5 [X − ] in which R 5 is a linear or branched hydrocarbon group of from 1 to about 4 carbon atoms or an acetyl group and X − is a saturated or unsaturated carboxylate anion of from 2 to about 22 carbon atoms containing 0 to 2 hydroxyl groups.

2. The adjuvant composition of claim 1 wherein the lecithin component (a) contains from 10 to 70 weight percent lecithin as phosphalidylcholine with the balance being selected from phosphatidylethanolamine, phosphalidylinositol, phosphatidic acid, glycolipids, complexed sugars and triglycerides, having a hydrophilic-lipophilic balance between 2 and 15.

3. The adjuvant composition of claim 1 wherein the lecithin component (a) has an average acetone insoluble (AI) content of more than 60 weight percent.

4. The adjuvant composition of claim 2 wherein the lecithin component (a) has an average acetone insoluble (AI) content of more than 60 weight percent.

5. The adjuvant composition of claim 1 wherein the organosilicon surfactant (b) of the general formula (I) is such that R 1 is the branched alkyl group:

CR 6 R 7 R 8 (CR 9 R 10 ) m (CR 11 R 12 ) n CHR 13 CH 2 —

in which R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 each independently is hydrogen or methyl, and wherein from 2 to 4 of the R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 groups are methyl and the subscripts m and n are each independently 0 or 1.

6. The adjuvant composition of claim 5 wherein R 1 contains from 2 to 4 methyl groups, CR 6 R 7 R 8 is selected from the group consisting of H 3 C—, (H 3 C) 2 CH— and (H 3 C) 3 C—, the subscripts m and/or n are 0, Z is R 2 and R 2 is —CH 2 CH 2 CH 2 —O—(C 2 H 4 O) a (C 3 H 6 O) b —R 4 in which R 4 is hydrogen, linear or branched alkyl of from 1 to 4 carbon atoms, or an acyl group, the subscript a is from 1 to about 20, subscript b is from 0 to about 10, and the sum of the subscripts a and b is from 1 to about 20.

7. The adjuvant composition of claim 6 wherein the subscript a is from 2 to about 15.

8. The adjuvant composition of claim 6 wherein the subscript a is from 4 to about 10.

9. The adjuvant composition of claim 6 wherein the subscript b is from 0 to about 6.

10. The adjuvant composition of claim 7 wherein subscript b is from 0 to about 6 and the sum of subscripts a and b is from 2 to about 15.

11. The adjuvant composition of claim 8 wherein subscript b is from 0 to about 4 and the sum of subscripts a and b is from about 4 to about 10.

12. The adjuvant composition of claim 5 , wherein R 1 contains from 2 to 4 methyl groups, CR 6 R 7 R 8 is H 3 C—, (H 3 C) 2 CH— or (H 3 C) 3 C—, m and/or n are 0 or 1, Z is R 3 and R 3 is —CH 2 CH 2 CH 2 —O—CH 2 (OH)—CH 2 —N + (CH 3 ) 2 —R 5 [X − ] in which R 5 is a linear or branched alkyl of from 1 to about 4 carbon atoms.

13. The adjuvant composition of claim 5 , wherein R 1 contains from 2 to 4 methyl groups, CR 1 R 2 R 3 is (H 3 C) 2 CH— or (H 3 C) 3 C—, m is 0 or 1, n is 0, Z is R 3 and R 3 is —CH 2 CH 2 CH 2 O—CH(OH)—CH 2 —N + (CH 3 ) 2 —R 5 [X − ] in which R 5 is a linear or branched alkyl group of from 1 to about 4 carbon atoms and X″ is a carboxylate anion of from 2 to about 10 carbon atoms and from 0 to 2 hydroxyl groups.

14. The adjuvant composition of claim 13 , wherein X − is a carboxylate anion of from 2 to about 6 carbon atoms and from 0 to 2 hydroxyl groups.

15. The adjuvant composition of claim 5 wherein the organosilicon surfactant is at least one ether- or polyether-modified monosilyl compound selected from the group consisting of:

CR 6 R 7 R 8 (CR 9 R 10 ) m (CR 11 R 12 ) n —CHR 13 —CH 2 —Si(CH 3 ) 2 —

—Z

(H 3 C) 2 CHCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 H

(H 3 C) 3 CCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 CH 3

(H 3 C) 2 CHCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O(CH 2 H 4 O) 5 (C 3 H 6 O) 2.5 H

(CH 3 ) 2 CHCH(CH 3 )CH(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(CH 2 CH 2 O) 4 H

H 3 CCH 2 CH(CH 3 )CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 H

H 3 CCH 2 C(CH 3 ) 2 CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 H

(H 3 C) 2 CHCH(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 CH 3

H 3 CCH 2 C(CH 3 ) 2 C(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O(CH 2 H 4 O) 5 (C 3 H 6 O) 2.5 H

(H 3 C) 2 CHCH 2 CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(CH 2 CH 2 O) 5 H

(H 3 C) 3 CCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH 2 CH 2 OH

(H 3 C) 2 CHCH(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—(C 2 H 4 O) 7.5 H

(H 3 C) 3 CCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O(CH 2 H 4 O) 5 (C 3 H 6 O) 2.5 H.

16. The adjuvant composition of claim 5 wherein the organosilicon surfactant of the general formula (I) is at least one quaternary ammonium-modified monosilyl compound selected from the group consisting of:

CR 6 R 7 R 8 (CR 9 R 10 ) m (CR 11 R 12 ) n —CHR 13 —CH 2 —Si(CH 3 ) 2 —

—Z

(H 3 C) 2 CHCH 2 CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 3 CH 2 COO − ]

(H 3 C) 2 CHCH(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 3 CH 2 COO − ]

H 3 CCH 2 C(CH 3 ) 2 C(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [(CH 2 OH) 2 (CH 3 )C—COO − ]

(H 3 C) 3 CCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [(CH 2 OH) 2 (CH 3 )C—COO − ]

(H 3 C) 3 CCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH 2 CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 2 CH 2 OH [(CH 2 OH) 2 (CH 3 )C—COO − ]

(H 3 C) 2 CHCH 2 CH2—Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 3 CH 2 COO − ]

(H 3 C) 2 CHCH(CH 3 )CH(CH 3 )CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 2 (OH)CH 2 COO − ]

H 3 CCH 2 CH(CH 3 )CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 2 (OH)CH 2 COO − ]

H 3 CCH 2 C(CH 3 ) 2 CH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 2 (OH)CH 2 COO − ]

(H 3 C) 2 CHCH 2 CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 2 (OH)CH 2 CH 2 COO − ]

H 3 CC(CH 3 ) 2 CH 2 CH 2 CH 2 —CH 2 —Si(CH 3 ) 2 —

—CH 2 CH 2 CH 2 —O—CH(OH)CH 2 N + (CH 3 ) 2 —

CH 2 CH 3 [CH 2 (OH)CH 2 COO − ].

17. The adjuvant composition of claim 1 wherein organosilicon surfactant (I) is present therein at 1 to 99 weight percent of the total weight of lecithin and organisilicon surfactant (I).

18. The adjuvant composition of claim 1 further comprising at least one acidification agent.

19. The adjuvant composition of claim 1 further comprising at least one wetting agent.

20. The adjuvant composition of claim 1 further comprising at least one component selected from the group consisting of foam control agent, organic solvent and water.

21. The adjuvant composition of claim 1 further comprising at least one acidification agent and at least one wetting agent.

22. The adjuvant composition of claim 1 containing from 1 to 10 weight percent of organosilicon surfactant(s) (I) by total weight of lecithin and organosilicon surfactants (I).

23. An agrochemical formulation, comprising:

the adjuvant composition of claim 1 combined with a pesticide, a defoliant, or a plant nutrient; or combinations thereof.

24. An agrochemical formulation, comprising:

the adjuvant composition of claim 1 combined with a plant growth regulator, a fertilizer; or combinations thereof.

25. A method of controlling pests on a plant, providing nutrients to a plant, or defoliating a plant, comprising the step of spraying the agrochemical formulation of claim 23 onto the plant.

26. A method of plant growth regulation or plant fertilization, comprising the step of spraying the agrochemical formulation of claim 24 onto external tissue of the plant.

Assignments (10)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2017
From: POLICELLO, GEORGE; NAUE, JEFERSON; MUKHERJEE, NARAYAN
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 043736/0988 →