Using novel amines to stabilize quaternary trialkylalkanolamines

Patent metadata

Field	Value
Publication number	US-10264785-B2
Application number	US-201715582883-A
Country	US
Kind code	B2
Filing date	May 1, 2017
Priority date	Apr 13, 2012
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

New stabilizers for solutions of choline hydroxide and related quaternary trialkylalkanolamines are disclosed. The stabilizers are alkyl hydroxylamines, hydrazines, hydrazides, or derivates thereof, including compounds containing more than one such functionality. The new stabilizers are effective at concentrations less than about 1000 ppm, and choline hydroxide solutions stabilized with the compounds described herein typically have Gardner Color change less than about 2.0 after six months at reasonable temperatures.

First claim

The invention claimed is:

1. A composition comprising a quaternary trialkylalkanolamine in an alcohol, ether or sulfoxide solvent at a concentration between about 0.1 wt % and about 45 wt % with a stabilizer selected from the group consisting of at least one alkyl hydroxylamine.

2. A composition comprising a quaternary trialkylalkanolamine in an ether or sulfoxide solvent at a concentration between about 0.1 wt % and about 80 wt % and a stabilizer selected from the group consisting of at least one alkyl hydroxylamine.

3. The composition of claim 1 , wherein the quaternary trialkylalkanolamine is choline hydroxide.

4. The composition of claim 1 , wherein the stabilizer is DEHA.

5. The composition of claim 1 , wherein a concentration of the stabilizer in the composition is not more than about 1 wt %.

6. The composition of claim 5 , wherein the concentration of the stabilizer in the composition is not more than about 500 ppm.

7. The composition of claim 5 , wherein the concentration of the stabilizer in the composition is not more than about 300 ppm.

8. The composition of claim 1 , wherein the composition has a Gardner Color change less than about 2.0 after 6 months.

9. A method of stabilizing a quaternary trialkanolamine solution comprising:
blending a liquid stabilizer consisting of at least one dialkylhydroxylamine with a quaternary trialkanolamine in an alcohol, ether or sulfoxide solvent at a concentration between about 0.1 wt % and about 45 wt % to form the stabilized quaternary trialkanolamine solution.

10. The method of claim 9 , wherein the liquid stabilizer is DEHA.

11. The method of claim 9 , wherein the quaternary trialkylalkanolamine is formed from a reaction mixture comprising a trialkylamine and an alkylene oxide, and the liquid stabilizer is blended with the reaction mixture before forming the quaternary trialkylalkanolamine.

12. The method of claim 9 , wherein the stabilizer is present in the stabilized solution at a concentration less than about 1000 ppm.

13. A method of forming a stabilized quaternary trialkylethanolamine solution, comprising blending a quaternary trialkylethanolamine with an alcohol, ether or sulfoxide solvent and a stabilizer selected from the group consisting of least one alkyl hydroxylamine to form a quaternary trialkylethanolamine solution wherein the quaternary trialkylethanolamine is present at a concentration between about 0.1 wt % and about 45 wt % and the stabilizer is present in an amount such that the stabilized quaternary trialkylethanolamine solution has a concentration of the stabilizer that is less than about 1000 ppm.

14. The method of claim 13 , wherein the stabilized quaternary trialkylethanolamine solution has a Gardner Color change less than about 2.0 after 6 months.

15. The method of claim 9 , wherein the stabilized quaternary trialkanolamine solution has a Gardner Color change less than about 2.0 after 6 months.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Ferguson Dave C

Classifications

• A01N25/22 Primary

  containing ingredients stabilising the active ingredients · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• C07C213/10 Primary

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C215/40

  with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton · CPC title

• C09K15/18

  containing an amine or imine moiety · CPC title