Hydrolysis resistant organomodified disiloxane surfactants
View Patent ↗Disiloxane compounds of the formula MM′ Where M comprises either branched allyl hydrocarbon substituents or silanyl substituents and M′ comprises an alkylpolyalkyleneoxide substituent. The disiloxane compounds of the invention exhibit an enhanced resistance to hydrolysis outside a pH range ranging from 6 to 7.5, and are useful as surfactants.
1. A silicone composition comprising a silicone having the formula:
MM′
where
M=R 1 R 2 R 3 SiO 1/2 ;
M′=R 4 R 5 R 6 SiO 1/2 ;
with R 1 selected from the group consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms and R 7 , where R 7 is selected from the group consisting of
R 8 R 9 R 10 SiR 12 and (R 4 R 5 R 6 )SiR 12 (Si(R 2 R 3 )SiO 1/2 )
with R 8 , R 9 , and R 10 each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon radicals having from 6 to 13 carbon atoms and R 12 is a divalent hydrocarbon radical having from 1 to 3 carbon atoms,
R 2 and R 3 are each independently selected from the group of from 1 to 6 carbon atom monovalent hydrocarbon radicals or R 1 , with R 4 an alkylpolyalkyleneoxide of the general formula:
R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14
where R 13 is a divalent linear or branched hydrocarbon radical having the structure:
—CH 2 —CH(R 15 )(R 16 ) d O—
where R 15 is H or methyl; R 16 is a divalent alkyl radical of 1 to 6 carbons where the subscript d may be 0 or 1;
R 14 is selected from the group consisting of H, monovalent hydrocarbon radicals of from 1 to 6 carbon atoms and acetyl where the subscripts a, b and c are zero or positive and satisfy the following relationships:
2≦ a+b+c≦ 20 with a≧ 2,
and R 5 and R 6 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 4 .
2. The composition of claim 1 where R 1 is iso-propyl.
3. The composition of claim 1 where R 1 is iso-butyl.
4. The composition of claim 1 where R 1 is tert-butyl.
5. The composition of claim 1 where R 1 is R 7 where R 7 has the formula:
R 8 R 9 R 10 SiR 12 with R 8 , R 9 , and R 10 each methyl and R 12 is a divalent hydrocarbon radical having 2 carbon atoms.
6. The composition of claim 1 where R 15 is hydrogen.
7. The composition of claim 1 where R 2 is methyl.
8. The composition of claim 2 where R 15 is hydrogen.
9. The composition of claim 2 where R 2 is methyl.
10. The composition of claim 3 where R 15 is hydrogen.
11. The composition of claim 3 where R 2 is methyl.
12. The composition of claim 4 where R 15 is hydrogen.
13. The composition of claim 4 where R 2 is methyl.
14. The composition of claim 5 where R 15 is hydrogen.
15. The composition of claim 5 where R 2 is methyl.
16. A silicone composition comprising a silicone having the formula:
MM′
where
M=R 1 R 2 R 3 SiO 1/2 ;
M′=R 4 R 5 R 6 SiO 1/2 ;
with R 1 selected from the group consisting of branched monovalent hydrocarbon radical of from 3 to 6 carbon atoms and R 7 , where R 7 is selected from the group consisting of
R 8 R 9 R 10 SiR 12 and (R 4 R 5 R 6 )SiR 12 (Si(R 2 R 3 )SiO 1/2 )
with R 8 , R 9 , and R 10 each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms and monovalent aryl or alkaryl hydrocarbon radicals having from 6 to 13 carbon atoms and R 12 is a divalent hydrocarbon radical having from 1 to 3 carbon atoms,
R 2 and R 3 are each independently selected from the group of from 1 to 6 carbon atom monovalent hydrocarbon radicals or R 1 , with R 4 an alkylpolyalkyleneoxide of the general formula:
R 13 (C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c R 14
where R 13 is a divalent linear or branched hydrocarbon radical having the structure:
—CH 2 —CH(R 15 )(R 16 ) d O—
where R 15 is H or methyl; R 16 is a divalent alkyl radical of 1 to 6 carbons where the subscript d may be 0 or 1;
R 14 is selected from the group consisting of H, monovalent hydrocarbon radicals of from 1 to 6 carbon atoms and acetyl where the subscripts a, b and c are zero or positive and satisfy the following relationships:
2≦ a+b+c≦ 20 with a≧ 2,
and R 5 and R 6 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 6 carbon atoms or R 4 wherein said silicone composition has an enhanced resistance to hydrolysis.
17. The composition of claim 16 where R 1 is iso-propyl.
18. The composition of claim 16 where R 1 is iso-butyl.
19. The composition of claim 16 where R 1 is tert-butyl.
20. The composition of claim 16 where R 1 is R 7 where R 7 has the formula:
R 8 R 9 R 10 SiR 12 with R 8 , R 9 , and R 10 each methyl and R 12 is a divalent hydrocarbon radical having 2 carbon atoms.
21. The composition of claim 16 where R 15 is hydrogen.
22. The composition of claim 16 where R 2 is methyl.
23. The composition of claim 17 where R 15 is hydrogen.
24. The composition of claim 17 where R 2 is methyl.
25. The composition of claim 18 where R 15 is hydrogen.
26. The composition of claim 18 where R 2 is methyl.
27. The composition of claim 19 where R 15 is hydrogen.
28. The composition of claim 19 where R 2 is methyl.
29. The composition of claim 20 where R 15 is hydrogen.
30. The composition of claim 20 where R 2 is methyl.
31. An aqueous emulsion wherein the discontinuous phase comprises water and the continuous phase comprises the composition of claim 1 .
32. An aqueous emulsion wherein the discontinuous phase comprises water and the continuous phase comprises the composition of claim 16 .
33. An aqueous emulsion wherein the continuous phase comprises water and the discontinuous phase comprises the composition of claim 1 .
34. An aqueous emulsion wherein the continuous phase comprises water and the discontinuous phase comprises the composition of claim 16 .
35. A non-aqueous emulsion wherein the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of claim 1 .
36. A non-aqueous emulsion wherein the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of claim 16 .
37. A non-aqueous emulsion wherein the continuous phase comprises a non-aqueous hydroxylic solvent and the discontinuous phase comprises the composition of claim 1 .
38. A non-aqueous emulsion wherein the continuous phase comprises a non-aqueous hydroxylic solvent and the discontinuous phase comprises the composition of claim 16 .