IP Library Granted Patent US 9,650,595
Granted Patent B2
US 9,650,595 · App. 14/808,560 · Granted May 16, 2017

Quaternary ammonium hydroxides

Inventor: Charles B. Little (Austin, TX)
Assignee: Sachem, Inc.
C11D7/5004C07C215/40C07C217/28C07D295/088C11D3/28C11D3/30C11D3/43C11D7/3209C11D7/3218C11D7/3227C11D7/3281C07C2101/04C11D1/62
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Quick Facts
Patent No.
US 9,650,595
App. No.
14/808,560
Granted
May 16, 2017
Kind
B2
Abstract

A composition including (a) a quaternary ammonium hydroxide having a general formula (I): as defined herein, and (b) a dipolar aprotic solvent substantially free of water.

Claims (16)

1. A composition of matter, wherein the composition comprises:

a quaternary ammonium hydroxide having a general formula (I):

wherein in the general formula (I):

R 1 may be C 1 -C 18 linear or branched alkyl, C 2 -C 18 linear or branched alkanol, C 3 -C 18 linear or branched polyol, benzyl, or substituted benzyl, wherein when present, substituted benzyl is substituted with one or more of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or halogen, or R 1 may have the following general formulae (i) or (ii):

 wherein in general formulae (i) and (ii), R 6 is independently C 1 -C 4 branched or unbranched alkyl,

R 2 and R 3 may be independently C 1 -C 18 linear or branched alkyl, C 2 -C 18 linear or branched alkanol, C 3 -C 18 linear or branched polyol, benzyl, or substituted benzyl, wherein when present, substituted benzyl is substituted with one or more of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or halogen, or

R 1 is as defined above, and R 2 and R 3 may together form a heterocyclic ring containing the quaternary ammonium N atom of the general formula (I) and 4 to 7 carbon atoms, or

R 1 is as defined above, and R 2 and R 3 may together form a heterocyclic ring containing the quaternary ammonium nitrogen atom of the general formula (I), and either a second nitrogen atom or an oxygen atom and 3 to 6 carbon atoms, wherein the second nitrogen atom may be substituted with one or two groups independently selected from C 1 -C 18 linear or branched alkyl, C 2 -C 18 linear or branched alkanol, C 3 -C 18 linear or branched polyol, benzyl, or substituted benzyl, wherein when present, substituted benzyl is substituted with one or more of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or halogen, or

R 1 , R 2 , and R 3 together may form a bicyclic structure containing from two to four carbon atoms between first and second bridgehead positions, wherein the quaternary N atom of the general formula (I) is at the first bridgehead position, and a carbon or a tertiary or quaternary nitrogen is at the second bridgehead position, wherein when the second bridgehead position is a carbon or a quaternary nitrogen, the carbon or quaternary nitrogen is substituted with R 5 , in which R 5 is H or a C 1 -C 4 branched or unbranched alkyl group, and

R 4 is C 1 -C 18 linear or branched alkyl, phenyl or substituted phenyl, or benzyl or substituted benzyl, wherein when present, substituted phenyl or substituted benzyl is substituted with one or more of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or halogen, with the provisos that, if R 4 is mono-substituted phenyl, the substituent is other than a 4-fluoro or a 4-alkyl group; and if R 4 is di-substituted phenyl, the di-substituted phenyl is other than 2,5-dimethylphenyl.

2. The composition of claim 1 wherein the quaternary ammonium hydroxide has general formula (II):

wherein, in general formula (II), each of a, b and c are independently 2-4, R 5 is H or a C 1 -C 4 branched or unbranched alkyl.

3. The composition of claim 1 wherein the quaternary ammonium hydroxide has general formula (III):

wherein, in general formula (III), each of a, b and c are independently 2-4, R 5 is a C 1 -C 4 branched or unbranched alkyl, and X is a halide or OH.

4. The composition of claim 1 wherein the quaternary ammonium hydroxide has general formula (IV):

wherein in general formula (IV), each of a, b and c are independently 2-4.

Assignments (3)
SECURITY INTEREST Recorded Aug 4, 2026
From: SACHEM, INC.
To: FIRST BUSINESS SPECIALTY FINANCE, LLC
Reel/Frame 075521/0429 →
RELEASE OF SECURITY INTEREST Recorded Jun 10, 2025
From: PNC BANK, NATIONAL ASSOCIATION
To: SACHEM, INC.; SACHEM ASIA, INC.
Reel/Frame 071368/0642 →
SECURITY INTEREST Recorded May 6, 2024
From: SACHEM, INC.; SACHEM ASIA, INC.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 067318/0340 →
Continuity (2)
Division 13430985 · Mar 27, 2012
Related Publication 20150329475A1 · Nov 19, 2015