N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and fluids containing an N-hydroxyalkylated polyamine
View Patent ↗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 comprising Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
at least one of R 4 and R 5 are 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 both R 4 and R 5 are unsaturated C 2 -C 20 acyclic hydrocarbyls.
4. The N-hydroxyalkylated polyamine of claim 1 , where R 3 is a saturated C 5 -C 10 acyclic hydrocarbyl, and R 4 and R 5 independently are C 5 -C 15 acyclic hydrocarbyls.
5. A drilling fluid comprising:
an aqueous phase;
an oleaginous phase; and
an N-hydroxyalkylated polyamine comprising 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.
6. The drilling fluid of claim 5 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl group or at least one of R 4 and R 5 are unsaturated C 2 -C 20 acyclic hydrocarbyls.
7. The drilling fluid of claim 5 , where Formula (I) comprises unsaturated or saturated cyclic hydrocarbyls formed from R 1 , R 2 , R 4 and R 5 , the cyclic hydrocarbyls being selected from cyclohexane, cyclohexene, benzene, naphthalene, or decahydronapthalene.
8. The drilling fluid of claim 7 , where the cyclic hydrocarbyls are substituted with one or more of alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated or unsaturated C 2 -C 20 acyclic hydrocarbyls, or combinations thereof.
9. The drilling fluid of any of claim 7 , where the cyclic hydrocarbyls are substituted with at least two acyclic hydrocarbyls or at least one C 2 -C 20 aminoalkoxy comprising two terminal hydroxyls.
10. An N-hydroxyalkylated polyamine comprising Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
both R 4 and R 5 are unsaturated C 2 -C 20 acyclic hydrocarbyls; and
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
11. The N-hydroxyalkylated polyamine of claim 10 , where R 3 is a saturated C 5 -C 10 acyclic hydrocarbyl, and R 4 and R 5 independently are C 5 -C 15 acyclic hydrocarbyls.
12. The N-hydroxyalkylated polyamine of claim 10 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl.
13. An N-hydroxyalkylated polyamine comprising Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is a saturated C 5 -C 10 acyclic hydrocarbyl;
R 4 and R 5 are independently are C 5 -C 15 acyclic hydrocarbyls; and
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
14. An N-hydroxyalkylated polyamine comprising Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
Formula (I) comprises unsaturated or saturated cyclic hydrocarbyls formed from R 1 , R 2 , R 4 and R 5 , the cyclic hydrocarbyls being selected from cyclohexane, cyclohexene, benzene, naphthalene, or decahydronapthalene;
the cyclic hydrocarbyls are substituted with at least two acyclic hydrocarbyls; and
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
15. The N-hydroxyalkylated polyamine of claim 14 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl.
16. The N-hydroxyalkylated polyamine of claim 14 , where the cyclic hydrocarbyls are substituted with one or more of an alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated or unsaturated C 2 -C 20 acyclic hydrocarbyls, or combinations thereof.
17. The N-hydroxyalkylated polyamine of claim 14 , where the cyclic hydrocarbyls are substituted with at least two acyclic hydrocarbyls.
18. The N-hydroxyalkylated polyamine of claim 14 , where the cyclic hydrocarbyls are substituted with at least one C 2 -C 20 aminoalkoxy comprising two terminal hydroxyls.