Low foam surfactant composition and methods of making the same
View Patent ↗There is provided herein a low foam surfactant composition comprising: (a) di-trisiloxane alkoxylate component of the general formula (I): (R 1 R 2 R 3 SiO) 2 (R 4 )Si—R 5 —Si(R 6 )(OSiR 7 R 8 R 9 ) 2 (I); and, (b) mono-trisiloxane alkoxylate component of the general formula (II): (R 12 R 13 R 14 SiO) 2 Si(R 15 )R 16 (II) wherein di-trisiloxane alkoxylate (I) is soluble in mono-trisiloxane alkoxylate and methods of making the same.
1. A low foam surfactant composition comprising
a) di-trisiloxane alkoxylate component of formula (I):
(R 1 R 2 R 3 SiO) 2 (R 4 )Si—R 5 —Si(R 6 )(OSiR 7 R 8 R 9 ) 2 (1)
where R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 each independently is methyl, ethyl or linear or branched monovalent hydrocarbon radical of 3 or 4 carbon atoms,
R 5 is a divalent polyalkyleneoxide group of the structure:
—(R 10 ) a O(C 2 H 4 O) b (C 3 H 6 O) c (C 4 H 8 O) d —(R 11 ) e —
where R 10 and R 11 each independently is a linear or branched divalent hydrocarbon radical of from 2 to 6 carbon atoms, a and e each independently is 0 or 1, b is 0 or greater, c is 1 or greater, and d is 0 or greater, provided that 1≤b+c+d≤20; and,
b) mono-trisiloxane alkoxylate component of formula (II):
(R 12 R 13 R 14 SiO) 2 Si(R 15 )R 16 (11)
where R 12 , R 13 , R 14 and R 15 each independently is a linear or branched monovalent hydrocarbon radical of from 1 to 4 carbon atoms, and
R 16 is a monovalent polyalkyleneoxide group of the structure:
—R 17 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i —R 18
where —R 17 is a linear or branched divalent hydrocarbon radical of from 2 to 6 carbon atoms,
R 18 is hydrogen, monovalent hydrocarbon radical of from 1 to 4 carbon atoms or acetyl, and g, h and i each independently is 0 or greater, provided that 1≤g+h+i≤15;
and, wherein di-trisiloxane alkoxylate (I) is soluble in mono-trisiloxane alkoxylate (II).
2. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are methyl, divalent polyalkyleneoxide group R 5 is such that R 10 and R 11 each independently is a hydrocarbon radical of 3 or 4 carbon atoms, a and e are 1, b is 4 to 6, c is 1.5 to 3 and d is 0 or 1; and in formula (II), R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 or 4 carbon atoms, R 18 is hydrogen, g is 4 to 6, his 1.5 to 3 and i is 0.
3. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are methyl, divalent polyalkyleneoxide group R 5 is such that R 10 and R 11 each independently is a hydrocarbon radical of 3 or 4 carbon atoms, a and e are 1, b is 0 or 1, c is 1 to 8 and d is 0 or 1; and in formula (II), R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 or 4 carbon atoms, R 18 is hydrogen, g is 4 to 6, his 1.5 to 3 and i is 0.
4. The low foam surfactant composition of claim 3 wherein c is 1 to 4.
5. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are methyl, divalent polyalkyleneoxide group R 5 is such that R 10 and R 11 each independently is a hydrocarbon radical of 3 or 4 carbon atoms, a and e are 1, b is 1 to 4, c is 1 and d is 0 or 1; and in formula (II), R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 or 4 carbon atoms, R 18 is hydrogen, g is 4 to 6, h is 1.5 to 3 and i is 0.
6. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are methyl, divalent polyalkyleneoxide group R 5 is such that R 10 and R 11 each independently is a hydrocarbon radical of 3 or 4 carbon atoms, a and e are 1, b is 4 to 8, c is 1.5 to 3 and d is 0 or 1; and in formula (II), R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 or 4 carbon atoms, R 18 is hydrogen, g is 6 to 8, and h and i are 0.
7. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are methyl, divalent polyalkyleneoxide group R 5 is such that a and e are each 0, b is 4 to 8, c is 1.5 to 3, and d is 0 or 1; and in formula (II), R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 or 4 carbon atoms, R 18 is hydrogen, g is 6 to 8, and h and i are 0.
8. The low foam surfactant composition of claim 1 wherein in formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are each methyl, divalent polyalkyleneoxide group R 5 is such that R 10 and R 11 each independently is a hydrocarbon radical of 3 or 4 carbon atoms, a and e are 1, b is 6 to 9, c is 1 and d is 0; and wherein component (b) each of R 12 , R 13 , R 14 and R 15 are methyl, R 17 is a hydrocarbon radical of 3 to 4 carbon atoms, R 18 is hydrogen, subscript g is 6 to 8, subscript h and i are each 0.
9. The low foam surfactant composition of claim 1 wherein in formula (I) R 5 is of the formula
—(CH 2 CH(R 25 )CH 2 ) a —O(C 2 H 4 O) b (C 3 H 6 O) c —(CH 2 CH(R 26 )CH 2 ) e —
where subscripts a, b, c and e are as defined, and R 25 and R 26 are each independently hydrogen or methyl.
10. The low foam surfactant composition of claim 9 wherein in R 5 , b is 0 or from 4 to about 10 and c is from 1 to about 9.
11. The low foam surfactant composition of claim 10 wherein in R 5 , a is 1, b is 5, c is 2.5 and e is 0 and R 25 and R 26 are hydrogen.
12. The low foam surfactant composition of claim 1 wherein component (a) is present in an amount of from about 5 to about 95 weight % and component (b) is present in an amount of from about 5 to about 95 weight % based on the combined weight of components (a) and (b).
13. The low foam surfactant composition of claim 1 wherein component (a) is present in an amount of from about 10 to about 30 weight % and component (b) is present in an amount of from about 70 to about 90 weight % based on the combined weight of components (a) and (b).
14. A method of making the low foam surfactant composition of claim 1 comprising combining:
a) di-trisiloxane alkoxylate component of the formula (I):
(R 1 R 2 R 3 SiO) 2 (R 4 )Si—R 5 —Si(R 6 )(OSiR 7 R 8 R 9 ) 2 (1)
where R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 and R 9 each independently is methyl, ethyl or linear or branched monovalent hydrocarbon radical of 3 or 4 carbon atoms,
R 5 is a divalent polyalkyleneoxide group having the structure:
—(R 10 ) a O(C 2 H 4 O) b (C 3 H 6 O) e (C 4 H 8 O) d —(R 11 ) e —
where R 10 and R 11 each independently is a linear or branched divalent hydrocarbon radical of from 2 to 6 carbon atoms, a and e each independently is 0 or 1, b is 0 or greater, c is 1 or greater, and d is 0 or greater, provided that 1≤b+c+d≤20; with
b) mono-trisiloxane alkoxylate component of the formula (11):
(R 12 R 13 R 14 SiO) 2 Si(R 15 )R 16 (11)
where R 12 , R 13 , R 14 and R 15 each independently is a linear or branched monovalent hydrocarbon radical of from 1 to 4 carbon atoms, and
R 16 is a monovalent polyalkyleneoxide group of the structure:
—R 17 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i —R 18
where —R 17 is a divalent hydrocarbon radical containing from 2 to 6 carbon atoms,
R 18 is hydrogen, vinyl, allyl, methallyl, propenyl, monovalent hydrocarbon radical of from 1 to 4 carbon atoms or acetyl, and subscripts g, hand i each independently is 0 or greater, provided that 1≤g+h+i≤15;
wherein di-trisiloxane alkoxylate (I) is soluble in mono-trisiloxane alkoxylate(II).
15. The low foam surfactant composition of claim 1 obtained by the hydrosilylation process which comprises reacting a mixture of diolefinically-modified polyalkylene oxide of formula (V):
R 22 O(C 2 H 4 O) k (C 3 H 6 O) m (C 4 H 8 O) p —R 23 (V)
where k, m and p are ≤0 provided that 1≤k+m+p≤20, and where R 22 and R 23 each independently is an olefinically modified group of the structure:
CH 2 ═C(R 24 )—(CH 2 ) r —
where R 24 is hydrogen or methyl and subscript r is 0 to 4, and mono alkenyl-terminated polyalkylene oxide component of formula (VI):
CH 2 ═C(R 21 )—(CH 2 ) r —O—(C 2 H 4 O) k (C 3 H 6 O) m (C 4 H 8 O) p —R 18 (VI)
where R 18 is hydrogen, monovalent hydrocarbon radical of from 1 to 4 carbon atoms or acetyl, R 21 is hydrogen or methyl, and k, m and p are as defined, and r is 0 to 4, with 1,1,1,3,5,5,5-heptaalkyltrisiloxane wherein the alkyl groups each independently contains from 1 to 4 carbon atoms, in the presence of a hydrosilylation catalyst, the hydrosilylation producing a mixture of component (a) of formula (I) and component (b) of formula (II).
16. The low foam surfactant composition of claim 15 where at least 5 percent of the R 18 groups is hydrogen, the process employing an excess of 1,1,1,3,5,5,5-heptaalkyltrisiloxane and a dehydrocondensation catalyst, wherein the excess 1,1,1,3,5,5,5-heptaalkyltrisiloxane reacts with terminal hydroxyl groups of formula (VI) to produce in situ a mixture of component (a) of formula (I) and component (b) of formula (II).
17. The low foam surfactant composition of claim 16 wherein hydrosilylation reaction product (b) of formula (II) is such that R 18 is hydrogen and at least a portion of same is then reacted with 1,1,1,3,5,5,5-heptaalkyltrisiloxane wherein the alkyl groups each independently contains from 1 to 4 carbon atoms to produce hydrosilylation reaction product (a) of formula (I).
18. The low foam surfactant composition of claim 1 further comprising an agrochemical active ingredient.
19. The low foam surfactant composition of claim 18 wherein the agrochemical active ingredient is one or more of a herbicide, insecticide, fungicide, growth regulator, micronutrient or fertilizer.
20. A crop or plant having the agrochemical composition of claim 18 applied thereto.
21. The low foam surfactant composition of claim 1 as a component of a coating composition, personal care composition, home care composition or composition for oil or gas application.
22. The low foam surfactant composition of claim 1 which has a level of foam that is less than 1,000 ml of foam, when 200 ml of a 0.1 wt % amount of the low foam surfactant composition is added to a 2 L graduated cylinder wherein the composition is a solution that is subjected to a nitrogen sparge through the solution through a stainless steel fit at a rate of 1 L per minute for one minute.
23. The low foam surfactant composition of claim 1 , comprising an amount of the di-trisiloxane alkoxylate component of formula (I) effective to reduce the amount of foam produced by the mono-trisiloxane alkoxylate component of formula (II), in the absence of the di-trisiloxane alkoxylate component.
24. The low foam surfactant composition of claim 23 , wherein the composition has a level of foam that is less than a surfactant composition that contains only the mono-trisiloxane alkoxylate component by at least 50% when measured by a test in which 200 ml of a 0.1 wt % amount of the low foam surfactant composition is added to a 2 L graduated cylinder wherein the composition is a solution that is subjected to a nitrogen sparge through the solution through a stainless steel fit at a rate of 1 L per minute for one minute and permitted to settle for one minute thereafter.