Biodegradable super-spreading, organomodified trisiloxane

Patent metadata

Field	Value
Publication number	US-10299471-B2
Application number	US-201615574513-A
Country	US
Kind code	B2
Filing date	May 30, 2016
Priority date	Jun 16, 2015
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

The invention relates to polyether-modified siloxanes which are both superspreading and readily biodegradable. In particular, the invention is directed to a composition including polyether-modified siloxanes of formula (I)

M a D b D′ c   Formula (I)
with M=R 1 3 SiO 1/2 , D=R 1 2 SiO 2/2 , D′=R 1 R 2 SiO 2/2 , where a is 2, b is between 0 and 0.1, c is between 1.0 and 1.15, 0 and 1.05, R 1 are independently hydrocarbyl having 1 to 8 carbon atoms, preferably methyl, ethyl, propyl or phenyl radicals, especially preferably methyl radicals, R 2 are independently a polyether radical of the formula (II)

—R 3 O[CH 2 CH 2 O] m [CH 2 CH(CH 3 )O] n R 5   Formula (II)
where m=3.4 to 11.0, n=2.5 to 8.0, wherein m/n=1.9 to 2.8, and R 3 are independently divalent hydrocarbyl radicals having 2 to 8 carbon atoms, and R 5 is hydrogen, wherein the polyether-modified siloxanes of formula (I) having a biodegradability of greater than 60%.

First claim

The invention claimed is:

1. A composition comprising polyether-modified siloxanes of formula (I)
M a D b D′ c   Formula (I)

with M is R 1 3 SiO 1/2 , D is R 1 2 SiO 2/2 , D′ is R 1 R 2 SiO 2/2 ,
where
a is 2
b is between 0 and 0.1,
c is between 1.0 and 1.15,
R 1 are independently hydrocarbyl having 1 to 8 carbon atoms,
R 2 are independently a polyether radical of the formula (II)
—R 3 O[CH 2 CH 2 O] m [CH 2 CH(CH 3 )O] n R 5   Formula (II)

where
m is from 3.4 to 11.0,
n is from 2.5 to 8.0,
and wherein m/n is from 1.9 to 2.8,
R 3 are independently divalent hydrocarbyl radicals having 2 to 8 carbon atoms,
R 5 is hydrogen
the polyether-modified siloxanes of formula (I) having a biodegradability of from 60% to 100% and wherein the molar mass of the polyether radical M(PE) is between 520 g/mol and 660 g/mol.

2. The composition according to claim 1 , wherein the sum total of m+n is from 9 up to 19.

3. The composition according to claim 2 , wherein a 0.1 percent by weight solution of the polyether-modified siloxanes of formula (I) in water has a spreading area of from 10 to 60 cm 2 .

4. The composition according to claim 2 , wherein the polyether-modified siloxanes of the formula (I) have an index c between 1 and 1.05, where the m/n ratio is 0.8 to 2.8 and a 0.1% by weight solution of these siloxanes in water has a spreading area of 15 to 60 cm 2 .

5. The composition according to claim 1 , wherein a 0.1 percent by weight solution of the polyether-modified siloxanes of formula (I) in water has a spreading area of from 10 to 60 cm 2 .

6. The composition according to claim 1 , wherein the polyether-modified siloxanes of the formula (I) have an index c between 1 and 1.05, where the m/n ratio is 0.8 to 2.8 and a 0.1% by weight solution of these siloxanes in water has a spreading area of 15 to 60 cm 2 .

7. The composition according to claim 1 , wherein the polyether-modified siloxanes of the formula (I) have a biodegradability of greater than 60%, and the index c is additionally between 1 and 1.05, where the R 5 radical is hydrogen and a 0.1% by weight solution in water has a spreading area of 15 to 60 cm 2 .

8. An adjuvant in crop protection wherein the adjuvant comprises the composition according to claim 1 .

9. A tank mix additive for spray liquors wherein the tank mix additive comprises the composition according to claim 1 .

10. The composition according to claim 1 , wherein the sum total of m+n is from 9.5 to 15.

11. The composition according to claim 1 , wherein the sum total of m+n is from 10 to 12.

12. The composition according to claim 1 , wherein b is 0, c is between 1.00 and 1.10, m is from 3.6 to 9.9, n is from 2.7 to 7.5, R 3 is selected from the group consisting of ethylene, propylene, 1-methylpropylene, 1,1-dimethylpropylene radical, and the polyether-modified siloxanes of formula (I) has a biodegradability of from 63% to 100%.

13. The composition according to claim 1 , wherein b is 0, c is between 1.00 and 1.05, m is from 4.5 to 8.5, n is from 3.0 to 6.0, R 3 is —CH 2 CH 2 CH 2 —, and the polyether-modified siloxanes of formula (I) having a biodegradability of from 65% to 100%.

14. The composition according to claim 1 , wherein a 0.1 percent by weight solution of the polyether-modified siloxanes of formula (I) in water has a spreading area of from 15 to 50 cm 2 .

15. The composition according to claim 1 , wherein a 0.1 percent by weight solution of the polyether-modified siloxanes of formula (I) in water has a spreading area of from 20 to 40 cm 2 .

16. A process for preparing polyether-modified siloxanes, comprising the steps of
a) purifying an H-siloxane of the formula (V)
M a D b D′ d   (V)

with M=R 1 3 SiO 1/2 , D=R 1 2 SiO 2/2 , D′=R 1 R 2 SiO 2/2 ,
where
a is 2,
b is between 0 and 0.1,
d is between 1.16 and 3,
R 1 are independently hydrocarbyl having 1 to 8 carbon atoms,
R 2 is hydrogen
b) reacting the purified product of step a) in the manner of a hydrosilylation with a terminally unsaturated polyether of the formula (VI)
R 4 O[CH 2 CH 2 O] m [CH 2 CH(CH 3 )O] n R 5   (VI)

where
m is from 3.4 to 11.0, n is from 2.5 to 8.0,
wherein m/n is from 1.9 to 2.8,
R 5 are each independently hydrocarbyl radicals having 1 to 16 carbon atoms or hydrogen, preferably hydrogen or methyl, especially hydrogen,
R 4 are independently monovalent terminally unsaturated hydrocarbyl having 2 to 8 carbon atoms and
wherein the molar mass of the polyether radical M(PE) is between 520 g/mol and 660 g/mol.

17. The process according to claim 16 , wherein the H-siloxane of the formula (V) is purified by employing a thermal separation process.

18. The process according to claim 16 , wherein R 1 is selected from the group consisting of methyl, ethyl, propyl or phenyl radicals, m is from 4.5 to 8.5, n is from 2.7 to 7.5, wherein m/n is from 0.55 to 3.00,
R 5 is selected from the group consisting of hydrogen or methyl, and
R 4 is selected from the group consisting of CH 2 ═CH 2 —, CH 2 ═CHCH 2 —, CH 2 ═CHCH(CH 3 )—, CH 2 ═CHC(CH 3 ) 2 , especially preferably CH 2 ═CHCH 2 —.

19. The process according to claim 16 , wherein R 1 is a methyl radical, n is from 3.0 to 6.0, wherein m/n is from 0.8 to 2.8,
R 5 is hydrogen, and
R 4 is CH 2 ═CHCH 2 —.

20. The process according to claim 16 , wherein in m/n is from 1.9 to 2.8.

Assignees

• Evonik Degussa Gmbh

Inventors

• Hänsel René
• Sieverding Ewald
• Ferenz Michael
• Windbiel Gerd
• Jacobi Andrea

Classifications

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• C08G2230/00

  Compositions for preparing biodegradable polymers · CPC title

• C08G65/336

  containing silicon · CPC title

• A01N25/06

  Aerosols · CPC title

• A01N47/36

  containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof · CPC title