Compositions comprising reverse micelles and methods for their use
View Patent ↗Compositions containing a reverse micelle comprising a first compound and a second compound are disclosed, wherein the second compound is configured to change conformation in response to a stimulus, a first conformation selected for formation of the reverse micelle, and a second conformation selected for disruption of the reverse micelle; and wherein the first compound is selected to interact with the first conformation of the second compound to form the reverse micelle.
1. A composition comprising a first compound and second compound in an oil wherein:
the first compound comprises an organic acid, sodium chloride, hydrogen phthalate, or a substituted or unsubstituted cinnamic acid or a salt or ester thereof;
the second compound has a first conformation that forms a reverse micelle interaction with the first compound;
the second compound has a second conformation that disrupts or prevents formation of a reverse micelle;
the second compound changes conformation in response to a stimulus; and
the viscosity of the composition is higher in the presence of the reverse micelle than in the absence of the reverse micelle.
2. The composition according to claim 1 , wherein the second compound is a surfactant.
3. The composition according to claim 1 , wherein the stimulus is at least one of photostimulation and electric stimulation.
4. The composition according to claim 1 , wherein the change in conformation is reversible.
5. The composition according to claim 1 , wherein the second compound is capable of disrupting the reverse micelle in response to irradiation with ultraviolet light.
6. The composition according to claim 1 , wherein the second compound comprises a photoswitchable azobenzene-modified surfactant.
7. The composition according to claim 1 , wherein the second compound comprises a quaternary ammonium salt of an azobenzene compound.
8. The composition according to claim 1 , wherein the second compound comprises a compound represented by the following general formula (1):
wherein R 2 , R 3 and R 4 each independently represent a lower alkyl group or form a pyridinium with the nitrogen atom, R 5 represents an alkyl group, L represents an alkylene group or an alkylene-oxy group and X represents a halogen atom.
9. The composition according to claim 8 , wherein the second compound comprises at least one selected from the group consisting of 4-butylazobenzene-4′-(oxyethyl)trimethylammonium bromide, 4-butylazobenzene-4′-(oxyethyl)trimethylammonium chloride, 4-hexylazobenzene-4′-(oxyethyl)trimethylammonium bromide, 4-hexylazobenzene-4′-(oxyethyl)trimethylammonium chloride, 4-octylazobenzene-4′-(oxyethyl)trimethylammonium bromide, and 4-octylazobenzene-4′-(oxyethyl)trimethylammonium chloride.
10. The composition according to claim 6 , wherein the second compound comprises a quaternary ammonium salt other than the photoswitchable azobenzene-modified surfactant.
11. The composition according to claim 10 , wherein the second compound comprises a compound represented by the following general formula (2):
wherein R 1 represents an alkyl group having 14 to 18 carbon atoms, R 2 , R 3 and R 4 each independently represent a lower alkyl group or forms a pyridinium with the nitrogen atom, and X represents a halogen atom.
12. The composition according to claim 10 , wherein the second compound comprises at least one selected from the group consisting of cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, cetylpyridinium chloride, octadecyltrimethylammonium bromide, octadecyltrimethylammonium chloride and octadecylpyridinium chloride.
13. The composition according to claim 1 , wherein the second compound is capable of disrupting the reverse micelle in response to electrolytic oxidation.
14. The composition according to claim 1 , wherein the second compound comprises a redox-active ferrocenyl surfactant.
15. The composition according to claim 14 , wherein the redox-active ferrocenyl surfactant comprises (11-ferrocenylundecyl)trimethylammonium bromide.
16. The composition according to claim 1 , wherein the second compound further comprises a quaternary ammonium salt, and the first compound comprises at least one selected from the group consisting of a substituted cinnamic acid, an unsubstituted cinnamic acid, a salt thereof and an ester thereof.
17. The composition according to claim 16 , wherein the quaternary ammonium salt comprises at least one selected from the group consisting of cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, cetylpyridinium chloride, octadecyltrimethylammonium bromide, octadecyltrimethylammonium chloride, and octadecylpyridinium chloride.
18. The composition according to claim 16 , wherein the first compound comprises at least one selected from the group consisting of cis-cinnamic acid, trans-cinnamic acid, sodium cinnamate, potassium cinnamate, α-methylcinnamic acid, 2-methylcinnamic acid, 2-fluorocinnamic acid, 2-(trifluoromethyl)cinnamic acid, 2-chlorocinnamic acid, 2-methoxycinnamic acid, 2-hydroxycinnamic acid, 2-nitrocinnamic acid, 2-carboxycinnamic acid, trans-3-fluorocinnamic acid, 3-(trifluoromethyl)cinnamic acid, 3-chlorocinnamic acid, 3-bromocinnamic acid, 3-methoxycinnamic acid, 3-hydroxycinnamic acid, 3-nitrocinnamic acid, 4-methylcinnamic acid, 4-fluorocinnamic acid, trans-4-(trifluoromethyl)-cinnamic acid, 4-chlorocinnamic acid, 4-bromocinnamic acid, 4-methoxycinnamic acid, 4-hydroxycinnamic acid, 4-nitrocinnamic acid, 3,3-dimethoxycinnamic acid, ethyl 4-methoxycinnamate, isopropyl 4-methoxycinnamate, octyl 4-methoxycinnamate, 2-ethoxyethyl 4-methoxycinnamate, sodium 4-methoxycinnamate, potassium 4-methoxycinnamate and glyceryl ethylhexanoate dimethoxycinnamate.
19. The composition according to claim 4 , wherein the first compound comprises at least one selected from the group consisting of a substituted cinnamic acid, an unsubstituted cinnamic acid, a salt thereof and an ester thereof.
20. The composition according to claim 1 , wherein the first compound comprises an organic acid.
21. The composition according to claim 20 , wherein the organic acid composes salicylic acid.
22. The composition according to claim 1 , wherein the oil comprises at least one selected from the group consisting of mineral oil, plant oil and synthetic oil.
23. The composition according to claim 1 , wherein the oil comprises at least one selected from the group consisting of paraffin oil, naphthene oil, aliphatic acid or derivative thereof, grease-base oil, poly-a-olefin, polyol ester and siloxane.
24. The composition according to claim 1 , having viscosity at 40° C. in the presence of the reverse micelle higher than viscosity at 40° C. in the absence of the reverse micelle.
25. The composition of claim 1 , wherein the viscosity of the composition in the presence of the reverse micelle is about 4×10 −3 to about 1000×10 −3 Pa·s at 40° C.
26. A composition comprising a first compound and a second compound in an oil wherein:
the second compound comprises at least one selected from cetyltrimethylammonium chloride, cetylpyridinium chloride, octadecyltrimethylammonium bromide, and octadecyltrimethylammonium chloride;
the second compound has a first conformation that forms a reverse micelle interaction with the first compound;
the second compound has a second conformation that disrupts or prevents formation of a reverse micelle;
the second compound changes conformation in response to a stimulus; and
the viscosity of the composition is higher in the presence of the reverse micelle than in the absence of the reverse micelle.
27. The composition of claim 26 further comprising an azobenzene-modified surfactant.
28. The composition of claim 26 further comprising at least one selected from a substituted or unsubstituted cinnamic acid, a salt thereof and an ester thereof.
29. The composition of claim 26 , wherein the viscosity of the composition in the presence of the reverse micelle is about 4×10 −3 to about 1000×10 −3 Pa·s at 40° C.
30. A composition comprising a first compound and a second compound in an oil wherein:
the first compound comprises an organic acid, sodium chloride, hydrogen phthalate, or a substituted or unsubstituted cinnamic acid or a salt or ester thereof;
the second compound comprises at least one selected from cetyltrimethylammonium chloride, cetylpyridinium chloride, octadecyltrimethylammonium bromide, and octadecyltrimethylammonium chloride;
the second compound has a first conformation that forms a reverse micelle interaction with the first compound;
the second compound has a second conformation that disrupts or prevents formation of a reverse micelle;
the second compound changes conformation in response to a stimulus; and
the viscosity of the composition is higher in the presence of the reverse micelle than in the absence of the reverse micelle.
31. The composition of claim 30 further comprising an azobenzene-modified surfactant.
32. The composition of claim 30 , wherein the viscosity of the composition in the presence of the reverse micelle is about 4×10 −3 to about 1000×10 −3 Pa·s at 40° C.