IP Library Patent Application 18712736
Patent Application
App. No. 18/712,736

PRODUCTION OF ANHYDROUS QUATERNARY AMMONIUM HYDROXIDES

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Patent No.
US None
App. No.
18/712,736
Abstract

A method for the synthesis of anhydrous quaternary ammonium hydroxides having the formula (NR 1 R 2 R 3 R 4 ) OH, wherein R 1 , R 2 , R 3 and R 4 are the same as or different from one another and are each individually selected from H, C 1 -C 10 alkyls including linear or cyclo alkyls, and C 6 -C 12 aryls by reacting an alkylene oxide with a tertiary amine having the formula R 1 R 2 R 3 N wherein R 1 , R 2 , and R 3 are the same or different and are each individually selected from C 1 -C 10 alkyls including linear and cyclo alkyls, C 1 -C 10 hydroxyalkyls, C 6 -C 12 aryls, and formulations having anhydrous quaternary ammonium hydroxides.

Claims (21)

1 . A method for the synthesis of an anhydrous quaternary ammonium hydroxide comprising:

reacting an alkylene oxide with a tertiary amine having the formula R1R2R3N wherein R1, R2, and R3 are the same or different and are each individually selected from C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls, to produce an anhydrous quaternary ammonium hydroxide having the formula (NR 1 R 2 R 3 R 4 ) OH, wherein R 1 , R 2 , R 3 , and R 4 are the same as or different from one another and are each individually selected from H, C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls.

2 . The method of claim 1 , wherein the alkylene oxide is selected from ethylene oxide, propylene oxide, butylene oxide, allyl glycidyl ether, hexene oxide, styrene oxide, epichlorohydrin, cyclohexene oxide and spiro-epoxy oxindole.

3 . The method of claim 1 , wherein the tertiary amine is selected from trimethylamine, triethylamine, tripropylamine, dimethylethylamine, diethylmethylamine, dimethylethanolamine, methyldiethanolamine, triethanolamine, dimethylpropanolamine, diethylethanolamine and methylethylpropanolamine.

4 . The method of claim 1 , wherein the reaction is performed in an aqueous environment.

5 . The method of claim 1 , wherein the reaction produces byproducts including water and unreacted amine.

6 . The method of claim 5 , wherein the reaction produces less than about 5% by weight water as byproduct.

7 . An electronic application formulation comprising an anhydrous quaternary ammonium hydroxide as claimed in claim 1 .

8 . The electronic application formulation of claim 7 , further comprising a solvent including isopropyl alcohol or an ethylene oxide reactive solvent.

9 . The electronic application formulation of claim 7 , further comprising water.

10 . An anhydrous quaternary ammonium hydroxide composition obtained by reacting an alkylene oxide with a tertiary amine having the formula R1R2R3N wherein R1, R2, and R3 are the same or different and are each individually selected from C 1 -C 10 alkyls, C 1 -C 10 hydroxyalkyls and C 6 -C 12 aryls.

11 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the alkylene oxide is selected from ethylene oxide, propylene oxide, butylene oxide, allyl glycidyl ether, hexene oxide, styrene oxide, epichlorohydrin, cyclohexene oxide, and spiro-epoxy oxindole.

12 . The anhydrous quaternary ammonium hydroxide composition of claim 11 , wherein the alkylene oxide is ethylene oxide.

13 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein R1, R2 and R3 are individually selected from C 1 -C 10 alkyls.

14 . The anhydrous quaternary ammonium hydroxide composition of claim 13 , wherein R1, R2 and R3 are individually selected from methyl and ethyl.

15 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein R1, R2 and R3 are individually selected from C 1 -C 10 hydroxyalkyls.

16 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein a molar ratio of alkylene oxide to tertiary amine present in the reaction ranges from about 6:1 to about 1:3.

17 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the reaction is performed in the presence of a solvent including N-methyl-2-pyrrolidone, dimethyl sulfoxide, dimethylacetamide, t-butyl alcohol, ethylene glycol, or propylene glycol.

18 . The anhydrous quaternary ammonium hydroxide composition of claim 10 , wherein the reaction is conducted at a temperature in the range from about 30° C. to about 60° C.

19 . The anhydrous quaternary ammonium hydroxide composition of claim 18 , wherein the reaction is conducted at a pressure less than about 60 psi.

20 . A method for etching, stripping or cleaning a surface of a semiconductor device including contacting the surface with the electronic application formulation of claim 7 .

Assignments (3)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 19, 2024
From: ZHOU, HUI; ZHANG, KE
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 067767/0286 →