IP Library Granted Patent US 12,172,954
Granted Patent B2
US 12,172,954 · App. 17/954,874 · Granted Dec 24, 2024

Alkoxylated secondary alcohol

Inventors: Jean-Philippe Gillet (Brignais, FR); Thierry Beillon (Sainte Foy les Lyon, FR)
Assignee: Arkema France
C07C43/13C07C41/03C08G65/2609C08G65/2663E04F11/1834E04F11/1844E04F2011/1819
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Quick Facts
Patent No.
US 12,172,954
App. No.
17/954,874
Granted
Dec 24, 2024
Kind
B2
Abstract

The invention relates to a compound of following formula (I): a preparation process, uses thereof and compositions containing the same, wherein R 1 and R 2 , represent, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 6 carbon atoms, where the sum of the carbon atoms of the groups R 1 and R 2 ranges from 2 to 7, and where R 1 and R 2 may also form, together and with the carbon atom bearing them, a 6-, 7-, or 8-membered ring; n is an integer of between 1 and 100, limits included; A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide, butylene oxide units and mixtures thereof; the group formed by R 1 , R 2 and the carbon atom to which R 1 and R 2 are attached has a degree of branching equal to 0, 1 or 2.

Claims (23)

1. A compound of formula (I) below:

wherein:

R 1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, pentyl or hexyl;

R 2 is ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, pentyl or hexyl, or where R 1 and R 2 may also form, together with the carbon atom to which R 1 and R 2 are attached, a 6- or 7- or membered ring;

n is an integer between, limits inclusive, 1 and 100;

A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; and

the group formed by R 1 , R 2 and the carbon atom to which R 1 and R 2 are attached has a degree of branching equal to 0, 1 or 2.

2. The compound as claimed in claim 1 , wherein the group formed by R 1 , R 2 and the carbon atom to which R 1 and R 2 are attached has a degree of branching of 1 or 2.

3. The compound as claimed in claim 1 , wherein the group formed by R 1 , R 2 and the carbon atom to which R 1 and R 2 are attached is a 4-methyl-2-pentyl radical.

4. A process for preparing a compound of formula (I) as defined in claim 1 , comprising the following successive steps:

(a) reacting a secondary alcohol of formula (II) below:

R 1 CH(OH)R 2   (II),

in which R 1 and R 2 are as defined in claim 1 ,

with n ethylene oxide(s), where n is as defined in claim 1 ,

in the presence of at least one catalyst of dimetallic cyanide type; and

(b) reacting the product obtained from step (a) with one or more oxides chosen from ethylene oxide, propylene oxide and butylene oxide, and mixtures thereof, in the presence of at least one catalyst of dimetallic cyanide type.

5. The process as claimed in claim 4 , wherein the secondary alcohol of formula (II) has a weight-average molar mass ranging from 70 to 200 g/mol.

6. The process as claimed in claim 4 , wherein the secondary alcohol of formula (II) is methylisobutylcarbinol.

7. The process as claimed in claim 4 , wherein the catalyst of dimetallic cyanide type is zinc hexacyanocobaltate.

8. The process as claimed in claim 4 , wherein the content of catalyst of dimetallic cyanide type ranges from 1 to 1000 ppm relative to the content of secondary alcohol of formula (II).

9. The process as claimed in claim 4 , wherein the ethylene oxide/secondary alcohol of formula (II) mole ratio ranges from 2 to 100.

10. The compound of formula (I) as defined in claim 1 , where the compound is one or more of a nonionic surfactant, low-foaming surfactant, wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescer, compatibilizer, emulsifying agent, dispersant, chemical intermediary, corrosion inhibitor, demulcent, plasticizer, sequestrants, mineral deposition inhibitor, ionic liquid, stabilizer, lubricant, bitumen additive, deinking additive, oil gellant, ore flotation collector, processing aid in manufacturing plastics, antistatic agent, and fertilizer coating additive.

11. A composition comprising at least one compound of formula (I) as defined in claim 1 , and one or more aqueous, organic or aqueous-organic solvents, optionally with one or more additives and fillers.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2024
From: GILLET, JEAN-PHILIPPE; BEILLON, THIERRY
To: ARKEMA FRANCE
Reel/Frame 068576/0762 →