Quaternary ammonium hydroxides of polyamines

Patent metadata

Field	Value
Publication number	US-12077730-B2
Application number	US-201917270881-A
Country	US
Kind code	B2
Filing date	Jul 29, 2019
Priority date	Aug 30, 2018
Publication date	Sep 3, 2024
Grant date	Sep 3, 2024

Abstract

The present disclosure provides a quaternary ammonium hydroxide solution comprising a reaction product of a polyamine and an organic oxirane. The quaternary ammonium hydroxide solution may be used in various applications, such as in removing chemical residue from a metal or dielectric surface.

First claim

The invention claimed is:

1. A quaternary ammonium hydroxide solution comprising the reaction product of (i) a polyamine having a formula:

where each R 1 is independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group, an alkyloxyalkyl group, a hydroxylated alkyl group, a hydroxylated alkyloxyalkyl group or two R 1 groups may be joined to form a cyclic amine, with the proviso that the R 1 groups are selected in such a combination that at least one tertiary nitrogen is formed and that each R1 group has less than 6 carbon atoms; x is 0 or an integer of 1 to 10; n is an integer of at least 2; R′ is an alkyl group with 2 to 10 carbon atoms, an aryl group, alkaryl group, or unsaturated hydrocarbyl with 2 to 10 carbon atoms, or a group containing O or N in combination with C and H and may form a cyclic structure; and (ii) an organic oxirane having the formula

where each R is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an unsaturated alkyl group, an aryl group an aralkyl group or one or more R groups may form a cyclic structure containing 3 to 12 carbon atoms and optionally the R groups may contain one or more oxygen atoms wherein the concentration of quaternized amines in the quaternary ammonium hydroxide solution ranges from 10% by weight to 70% by weight, based on the total amount of the quaternized ammonium hydroxide solution.

2. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is bis(3-dimethylaminopropyl) ether.

3. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is bis(2-morpholinoethyl) ether.

4. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is bis(2-dimethylaminoethyl)amine.

5. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is N, N, N-tris(3-dimethylaminopropyl)amine.

6. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is N, N, N′, N″, N″-pentamethyldiethylenetriamine.

7. The quaternary ammonium hydroxide solution of claim 1 wherein the polyamine is N, N, N′, N″, N″-pentamethyldipropylenetriamine.

8. The quaternary ammonium hydroxide solution of claim 1 wherein the organic oxirane is ethylene oxide.

9. The quaternary ammonium hydroxide solution of claim 1 wherein the organic oxirane is propylene oxide.

10. The quaternary ammonium hydroxide solution of claim 1 wherein the quaternary ammonium hydroxide solution contains 1 mole percent or more of quaternary ammonium compounds having at least two quaternary groups compared to the total moles of quaternary compounds.

11. The quaternary ammonium hydroxide solution of claim 1 further comprising water.

12. The quaternary ammonium hydroxide solution of claim 1 further comprising a miscible organic solvent.

13. A composition for removing chemical residue from a metal surface or dielectric surface comprising the quaternary ammonium hydroxide solution of claim 1 .

14. A method for removing chemical residue from a metal surface or dielectric surface comprising contacting the metal surface or dielectric surface with the composition of claim 1 .

15. A method of forming quaternary ammonium hydroxide solution of claim 1 comprising (i) contacting the polyamine with the organic oxirane in situ to convert the polyamine to a polyamine comprising a tertiary group and (ii) allowing the polyamine comprising the tertiary amine group to further react with the organic oxirane to form the quaternary ammonium hydroxide.

16. The method of claim 15 wherein the polyamine is N,N′-bis(2-aminoethyl)piperazine.

17. The method of claim 15 wherein the polyamine is N,N′-bis(3-aminopropyl)piperazine.

18. The method of claim 15 wherein the polyamine is bis(2-dimethylaminoethyl) ether.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Champion Donald H
• Lewis David C
• Uriarte Juventino
• Zhou Hui
• Zhang Ke
• Zheng Chai

Classifications

• C11D7/26

  containing oxygen · CPC title

• C11D3/20

  containing oxygen {(C11D3/162, C11D3/164, C11D3/166, C11D3/168 take precedence)} · CPC title

• C11D7/3209

  Amines or imines with one to four nitrogen atoms; Quaternized amines · CPC title

• G03F7/425

  containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen · CPC title

• C11D2111/22

  Electronic devices, e.g. PCBs or semiconductors · CPC title