N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and fluids containing an N-hydroxyalkylated polyamine
N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and drilling fluids containing N-hydroxyalkylated polyamines are provided, in which the N-hydroxyalkylated polyamine includes Formula (I): where R 1 and R 2 are independently a —C or —CH group; R 3 is an aliphatic hydrocarbyl; R 4 and R 5 are independently acyclic hydrocarbyls, or R 1 , R 2 , R 4 , and R 5 are covalently connected to form a cyclic hydrocarbyl; and R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
1. An N-hydroxyalkylated polyamine of Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
R 4 and R 5 are independently acyclic hydrocarbyls, or R 1 , R 2 , R 4 , and R 5 are covalently connected to form an unsaturated cyclic hydrocarbyl, wherein the unsaturated cyclic hydrocarbyl is substituted with one or more of an alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated C 2 -C 20 acyclic hydrocarbyls, or unsaturated C 2 -C 20 acyclic hydrocarbyls; and
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
2. The N-hydroxyalkylated polyamine of claim 1 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl.
3. The N-hydroxyalkylated polyamine of claim 1 , where at least one of R 4 and R 5 are unsaturated C 2 -C 20 acyclic hydrocarbyls.
4. The N-hydroxyalkylated polyamine of claim 1 , where the unsaturated cyclic hydrocarbyl is substituted with at least two acyclic hydrocarbyls.
5. The N-hydroxyalkylated polyamine of claim 1 , where the unsaturated cyclic hydrocarbyl is substituted with at least one C 2 -C 20 aminoalkoxy comprising two terminal hydroxyls.
6. The N-hydroxyalkylated polyamine of claim 1 , where R 1 , R 2 , R 4 and R 5 form an unsaturated cyclic hydrocarbyl, wherein the unsaturated cyclic hydrocarbyl is selected from Formulas (III) to (XVII):
where R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 independently are H, alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, or combinations of these, and
where at least one of R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 is not H.
7. A drilling fluid comprising:
an aqueous phase;
an oleaginous phase; and
an N-hydroxyalkylated polyamine of Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls; and
R 1 , R 2 , R 4 and R 5 , form a cyclic hydrocarbyl, the cyclic hydrocarbyl being selected from Formulas (II) to (XVIII):
wherein, R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 independently are H, alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, or combinations of these.
8. The drilling fluid of claim 7 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl group.
9. The drilling fluid of claim 7 , where the cyclic hydrocarbyl is substituted with one or more of alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated C 2 -C 20 acyclic hydrocarbyls, or combinations thereof.
10. The drilling fluid of claim 7 , where the cyclic hydrocarbyl is substituted with at least one C 2 -C 20 aminoalkoxy comprising two terminal hydroxyls.
11. The N-hydroxyalkylated polyamine of claim 1 , where R 4 and R 5 are independently acyclic hydrocarbyls.