IP Library › Granted Patent US 10,233,200

Granted Patent B2

US 10,233,200 · App. 15/681,750 · Granted Mar 19, 2019

Organomodified monosilyl compound, its preparation and applications thereof

Inventors: Narayan Mukherjee (Croton-on-Hudson, NY); George A Policello (Ossining, NY)

Assignee: Momentive Performance Matericals Inc.

C07F7/081 A01N25/02 A01N25/24 A01N37/10

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 10,233,200
App. No.: 15/681,750
Granted: Mar 19, 2019
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

Organomodified monosilyl compounds as defined herein exhibit excellent resistance to hydrolysis over a wide range of pH and excellent wetting properties. The organomodified monosilyl compounds are advantageously employed as wetting agents in any of a wide variety of products such as agrochemical compositions, cosurfactants, coatings, personal care products and home care products.

Claims (88)

1. An organomodified monosilyl compound of the general formula:

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 organomodifed monosilyl compound of claim 1 , wherein R 1 is a 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, from 2 to 4 of R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are methyl and subscripts m and n each independently is 0 or 1.

3. The organomodified monosilyl compound of claim 2 , 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—, 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, subscript a is from 1 to about 20, subscript b is from 0 to about 10 and the sum of subscripts a and b is from 1 to about 20.

4. The organomodified monosilyl compound of claim 3 , wherein subscript a is from 2 to about 15.

5. The organomodified monosilyl compound of claim 4 , wherein subscript b is from 0 to about 6 and the sum of subscripts a and b is from 2 to about 15.

6. The organomodified monosilyl compound of claim 3 , wherein subscript a is from 4 to about 10.

7. The organomodified monosilyl compound of claim 6 , wherein subscript b is from 0 to about 4 and the sum of subscripts a and b is from about 4 to about 10.

8. The organomodified monosilyl compound of claim 3 , wherein subscript b is from 0 to about 6.

9. An agrochemical composition comprising a wetting agent-effective amount of at least one organomodified monosilyl compound of claim 8 .

10. An agrochemical composition comprising a wetting agent-effective amount of at least one organomodified monosilyl compound of claim 3 .

11. The organomodified monosilyl compound of claim 2 , 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.

12. An agrochemical composition comprising a wetting agent-effective amount of at least one organomodified monosilyl compound of claim 11 .

13. The organomodified monosilyl compound of claim 2 , 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 organomodified compound 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. An agrochemical composition comprising a wetting agent-effective amount of at least one organomodified monosilyl compound of claim 13 .

16. The organomodified monosilyl compound of claim 2 which 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.

17. An agrochemical composition comprising a wetting agent-effective amount of at least one organomodified monosilyl compound of claim 16 .

18. The organomodified monosilyl compound of claim 2 which 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 —