Organomodified monosilyl compound, its preparation and applications thereof

Patent metadata

Field	Value
Publication number	US-10233200-B2
Application number	US-201715681750-A
Country	US
Kind code	B2
Filing date	Aug 21, 2017
Priority date	Aug 21, 2017
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

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.

First claim

The invention claimed is:

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 —
—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

Assignees

• Momentive Performance Mat Inc
• Momentive Performance Matericals Inc

Inventors

• Mukherjee Narayan
• Policello George A

Classifications

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• C07F7/081 Primary

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• A01N37/10

  Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof · CPC title

• A01N25/24

  containing ingredients to enhance the sticking of the active ingredients · CPC title

• A01N25/30

  characterised by the surfactants · CPC title