Sugar/gluconoamide alkoxylate compositions and uses thereof
Compositions comprising a sugar alkoxylate and processes for preparing said compositions are provided. The compositions can be used as a bio-film inhibitor, rheology modifier, emulsion breaker, and/or emulsion inverter. Additionally, the compositions can be used in methods of breaking and/or inverting an emulsion of water and oil.
1 . A surfactant composition comprising a sugar alkoxylate, wherein the sugar alkoxylate is obtained by the process of:
reacting a sugar lactone with a polyamine, alkanolamine, or combination thereof to form a sugar amide; and
alkoxylating the sugar amide in the presence of an alkoxylating agent to form the sugar alkoxylate.
2 . The composition of claim 1 wherein the molar ratio of sugar lactone to polyamine is about 2:1 or greater.
3 . The composition of claim 1 wherein the sugar lactone is selected from the group consisting of 1,5-D-gluconolactone, 1,4-D-galactonolactone, D-mannono-1,4-lactone, ascorbic acid, lactide, d-lactone, d-caprolactone, ε-caprolactone, g-butyrolactone, gluonic acid d-lactone, b-propiolactone, coumarin, whiskey lactone, and combinations thereof.
4 . The composition of claim 3 wherein the sugar lactone is 1,5-D-gluconolactone.
5 . The composition of claim 1 —wherein the polyamine is a polyamine of formula (I): H 2 N—X—NH 2 , wherein X is —(CH 2 ) m —, —(Ar)—, —(CH 2 Ar) n —, —(CH 2 ) o Ar(CH 2 ) o ) p —, or —(CH 2 ) q NH(CH 2 ) q ) r —, wherein m, n, o, and q are an integer from 1 to 10 and p and r are an integer from 1 to 100.
6 . The composition of claim 1 wherein the polyamine is selected from the group consisting of ethylenediamine, 1,6-hexamethylenediamine, diethylenetriamine, tetraethylenepentamine, 1,3-phenylenediamine, 1,4-phenylenediamine, 1,2-diphenyl-1,2-ethylenediamine, propylenediamine, isopropylenediamine, butylenediamine, piperazine, pentylenediamine piperazine, N,N′-Bis-(2-aminoethyl) piperazine, piperazinoethylethylenediamine, aminoethylpiperazine, triethylenetetramine, pentaethylenehexamine, hexaethyleneheptamine tris(2-aminoethyl)amine, dipropylenetriamine, dimethylaminopropylamine, diisopropylenetriamine, dibutylenetriamine, di-sec-butylenetriamine, triethylenetetraamine, tripropylenetetraamine, triisobutylenetetraamine, tetraethylenepentamine, dimethylaminopropylamine polyethylenepolyamine, and combinations thereof.
7 . The composition of claim 1 wherein the molar ratio of alkoxylating agent to sugar amide is at least about 7:1.
8 . The composition of claim 1 wherein the alkoxylating agent is selected from the group consisting of ethylene oxide, propylene oxide, styrene oxide, butylene oxide, and combinations thereof.
9 . The composition of claim 1 wherein alkoxylating the sugar amide comprises a series of two or more alkoxylations, each comprising an alkoxylating agent.
10 . A surfactant composition comprising a sugar alkoxylate, wherein the sugar alkoxylate is obtained by the process of:
reacting a sugar lactone with a polyamine, alkanolamine, or combination thereof to form a sugar amide; and
alkoxylating the sugar amide in the presence of an alkoxylating agent to form the sugar alkoxylate;
wherein the sugar lactone is d-gluconolactone, wherein the polyamine is a polyamine of formula (I): H 2 N—X—NH 2 , and wherein the sugar amide is a sugar amide of formula (II):
wherein X is —(CH 2 ) m —, —(Ar)—, —(CH 2 Ar) n —, —(CH 2 ) o Ar(CH 2 ) o ) p —, or —(CH 2 ) q NH(CH 2 ) q ) r —, wherein m, n, o, and q are an integer from 1 to 10 and p and r are an integer from 1 to 100.
11 . The composition of claim 10 wherein alkoxylating the sugar amide of formula (II) comprises:
contacting the sugar amide of formula (II) with propylene oxide to form an intermediate composition; and
contacting the intermediate composition with ethylene oxide to form the sugar alkoxylate.
12 . The composition of claim 11 wherein the sugar alkoxylate has the structure of formula (III):
wherein a 1 to a 10 are integers and the sum of a 1 to a 10 is an integer from 1 to 100 and R 1 is hydrogen, alkyl, or aryl.
13 . The composition of claim 12 , wherein R 1 is hydrogen, C 1 to C 8 alkyl, or phenyl.
14 . The composition of claim 12 , wherein R 1 is hydrogen or methyl.
15 . The composition of claim 11 , wherein the sugar alkoxylate has the structure of Formula IIIA:
wherein b 1 to b 10 are integers and the sum of the integers of b 1 to b 10 is 1 to 100.
16 . A polymer composition comprising:
a water-in-oil emulsion comprising an aqueous phase comprising water and a water-soluble or water-dispersible polymer, and an oil phase comprising an oil and an emulsifying agent;
an inverting surfactant; and
a surfactant composition comprising a sugar alkoxylate, wherein the sugar alkoxylate is obtained by the process of:
reacting a sugar lactone with a polyamine, alkanolamine, or combination thereof to form a sugar amide; and
alkoxylating the sugar amide in the presence of an alkoxylating agent to form the sugar alkoxylate.
17 . A method of dissolving the water-soluble or water-dispersible polymer of the polymer composition of claim 16 comprising contacting the water-in-oil emulsion with the surfactant composition.
18 . A method of breaking an emulsion of water and oil comprising introducing an effective amount of an emulsion breaker composition into contact with the emulsion to destabilize the emulsion, wherein the emulsion breaker composition comprises a surfactant composition of claim 1 .
19 . A method of inverting an emulsion of water and oil comprising introducing an effective amount of an emulsion inverter composition into contact with the emulsion to destabilize the emulsion, wherein the emulsion inverter composition comprises a surfactant composition of claim 1 .
20 . A method of inhibiting bio-film comprising introducing an effective amount of a bio-film inhibitor, wherein the bio-film inhibitor comprises a surfactant composition of claim 1 .