N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and fluids containing an N-hydroxyalkylated polyamine

Patent metadata

Field	Value
Publication number	US-10934249-B2
Application number	US-201916353607-A
Country	US
Kind code	B2
Filing date	Mar 14, 2019
Priority date	Jan 3, 2018
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Saudi Arabian Oil Co

Inventors

• Hilfiger Matthew
• Reddy B Raghava

Classifications

• C09K8/36

  Water-in-oil emulsions · CPC title

• C07C215/14 Primary

  the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups · CPC title

• C07B41/02

  of hydroxy or O-metal groups · CPC title

• C07C215/10

  with one amino group and at least two hydroxy groups bound to the carbon skeleton · CPC title

• C07C213/04

  by reaction of ammonia or amines with olefin oxides or halohydrins · CPC title