# US 10,370,331 B2 · Polymerization inhibitor compositions

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- Number: US 10,370,331 B2
- Document ID: US10370331B2
- Status: Granted
- Kind: B2
- Application number: 15/915,201
- Filed: 2018-03-08
- Published: 2018-09-13
- Granted: 2019-08-06
- Earliest claimed: 2017-03-09
- Assignees: Ecolab USA Inc.
- Applicants: Ecolab USA Inc.
- Inventors: Jonathan Masere; Javier Florencio; Ramon Colorado, Jr.; Andrew R. Neilson; David Youdong Tong
- Web page: https://patentgrep.com/patent/US10370331B2

## CPC

- C07D 211/94: Oxygen atom, e.g. piperidine N-oxide
- C07C 7/20: Use of additives, e.g. for stabilisation
- C07C 51/50: Use of additives, e.g. for stabilisation
- C07C 67/62: Use of additives, e.g. for stabilisation
- C07C 231/22: Separation; Purification; Stabilisation; Use of additives (separation of optical isomers C07C231/20)
- C08F 2/40: using retarding agents
- Y02P 20/10: Process efficiency
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Disclosed herein are compositions including between 20 wt % and 50 wt % of a nitroxyl compound such as 2,2,6,6-tetramethylpiperidinyl-1-oxyl. The compositions are stable under field conditions of transportation and storage. The compositions remain homogeneous and pumpable or pourable at temperatures between −20° C. and 60° C., even when temperatures fluctuate in this range over a period of 10 days to 5 years, and even where the container used to transport and store the composition is made from metal or includes a metal surface contacting the composition.

## Claims

### Claim 1

A composition comprising about 30 wt % to 50 wt % of one or more nitroxyl compounds;
about 20 wt % to 30 wt % water;
about 25 wt % to 35 wt % diethylene glycol monobutyl ether; and
about 1 wt % to 10 wt % of a hydrocarbon solvent, the hydrocarbon solvent comprising one or more of bis(2-hydroxyethyl) ether, dimethyl benzene-1,2-dicarboxylate, 4-methyl-1,3-dioxolan-2-one, 4-oxa-2,6-heptandiol, 2-(2-hydroxy-propoxy)-propan-1-ol, 2-(2-hydroxy-1-methyl-ethoxy)-propan-1-ol, 2-ethylhexan-1-ol, propane-1,2-diol, and 1-acetoxy-2-butoxyethane.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the composition comprises about 35 wt % to 50 wt % of the one or more nitroxyl compounds.

### Claim 3 (depends on 1)

The composition of claim 1 wherein the composition comprises about 40 wt % to 50 wt % of the one or more nitroxyl compounds.

### Claim 4 (depends on 1)

The composition of claim 1 wherein the one or more nitroxyl compounds are selected from 2,2,6,6-tetramethylpiperidinyl-1-oxyl, 1-hydroxy-2,2,6,6-tetramethylpiperidine, 4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl, 4-oxo-2,2,6,6-tetramethylpiperidinyl-1-oxyl, 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, 1-hydroxy-4-oxo-2,2,6,6-tetramethylpiperidine.

### Claim 5 (depends on 1)

The composition of claim 1 wherein the one or more nitroxyl compounds consists essentially of 4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl.

### Claim 6 (depends on 1)

The composition of claim 1 wherein the composition is enclosed in a container.

### Claim 7 (depends on 6)

The composition of claim 6 wherein the container comprises a metal surface contacting the composition.

### Claim 8 (depends on 7)

The composition of claim 7 wherein the metal is a stainless steel.

### Claim 9 (depends on 1)

The composition of claim 1 wherein the composition is stable and is pumpable or pourable between −20° C. and 60° C.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the composition is stable and is pumpable or pourable between −10° C. and 60° C.

### Claim 11 (depends on 1)

The composition of claim 1 wherein the composition is stable and is pumpable or pourable for a period of about 10 days to 5 years.

### Claim 12 (depends on 1)

The composition of claim 1 wherein the composition is stable and is pumpable or pourable over a temperature range of −20° C. to 60° C. and a temporal range of about 10 days to 5 years, further wherein the temperature varies within the temperature range over the temporal range.

### Claim 13

A method comprising
a) forming a composition comprising about 20 wt % to 50 wt % of one or more nitroxyl compounds, about 20 wt % to 30 wt % water, about 25 wt % to 35 wt % diethylene glycol monobutyl ether, and about 1 wt % to 10 wt % of a hydrocarbon solvent, the hydrocarbon solvent comprising one or more of bis(2-hydroxyethyl) ether, dimethyl benzene-1,2-dicarboxylate, 4-methyl-1,3-dioxolan-2-one, 4-oxa-2,6-heptandiol, 2-(2-hydroxy-propoxy)-propan-1-ol, 2-(2-hydroxy-1-methyl-ethoxy)-propan-1-ol, 2-ethylhexan-1-ol, propane-1,2-diol, and 1-acetoxy-2-butoxyethane;
b) storing the composition in an enclosed container for a period of about 10 days to 5 years under conditions wherein the composition reaches a temperature between 0° C. and 20° C. at least once during the storage period;
c) removing the composition from the container by pumping or pouring; and
d) applying the composition to an industrial process stream comprising one or more unsaturated polymerizable compounds.

### Claim 14 (depends on 13)

The method of claim 13 wherein the removing, the applying, or both are carried out at a temperature between 0° C. and −20° C.

### Claim 15 (depends on 13)

The method of claim 13 wherein the method further includes transporting the composition.

### Claim 16 (depends on 13)

The method of claim 13 wherein the container comprises a metal surface and storing the composition comprises contacting the composition with the metal surface.