Cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture

Patent metadata

Field	Value
Publication number	US-11773053-B2
Application number	US-201716769845-A
Country	US
Kind code	B2
Filing date	Dec 20, 2017
Priority date	Dec 20, 2017
Publication date	Oct 3, 2023
Grant date	Oct 3, 2023

Abstract

The present invention concerns new cationic quaternary ammonium compounds which exhibit excellent adsorption properties on negatively charged surfaces. These ones can notably be obtained firstly by reacting an internal ketone with a twin-tail amine under reductive amination conditions to obtain a twin tail triamine, then subjecting the twin tail triamine to a quaternization reaction. They can also obtained be obtained by the quaternization reaction of a certain diamine.

First claim

The invention claimed is:

1. A compound of general formula (I)

wherein R n and R m independently represent a C 3 -C 27 alkyl group,
R 1 to R 6 , which may be the same or different at each occurrence, represent hydrogen or a C 1 -C 8 alkyl group or wherein a pair of substituents selected from R 1 , R 2 and R 3 in formula (I) or from R 4 , R 5 and R 6 in formula (I), optionally form a divalent hydrocarbon radical with 2 to 6 carbon atoms thereby forming a ring structure with the nitrogen atom to which they are attached,
wherein at least one of R 1 to R 6 is a methyl group, and
X 1 and X 2 , which are the same or different at each occurrence, represent a linear or branched divalent hydrocarbon radical with 1 to 24 carbon atoms which can be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups.

2. The compound of formula (I) in accordance with claim 1 , wherein X 1 and X 2 are —(CH 2 ) m with m being an integer equal to 2 to 20 and R 1 to R 6 are hydrogen or an alkyl group with 1 to 6 carbon atoms.

3. The compound in accordance with claim 2 wherein X 1 and X 2 are —(CH 2 ) 3 — and R 1 to R 6 are methyl.

4. The compound of formula (I) in accordance with claim 1 , wherein X 1 and X 2 are a branched divalent hydrocarbon group, which may be optionally substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups and R 1 to R 6 are as defined.

5. The compound of formula (I) in accordance with claim 1 , wherein X 1 and X 2 are a branched or linear divalent hydrocarbon group containing 2 to 20 carbon atoms substituted and/or interrupted by one or more heteroatoms or heteroatom containing groups and R 1 to R 6 are as defined.

6. The compound of formula (I) in accordance with claim 1 , wherein X 1 and X 2 are a divalent aliphatic group containing 2 to 20 carbon atoms with the exception of —(CH 2 ) 3 — and R 1 to R 6 are as defined.

7. The compound of formula (I) in accordance with claim 1 , wherein X 1 , X 2 , R n , and R m are as defined in claim 1 and R 1 to R 6 are a C 2 -C 8 alkyl group.

8. A process for the preparation of a compound of formula (I) as defined in claim 1 , the process comprising reacting an internal ketone K1 of formula (V), which can be obtained by a process P of decarboxylative ketonization, with a twin-tail amine of formula (VI) under reductive amination conditions to obtain a twin tail triamine of formula (VII) in accordance with the following general reaction scheme

wherein R n , R m , R 1 to R 4 , X 1 and X 2 have the meaning as defined in claim 1 in a first step, followed by a second step in which the reaction product obtained in the first step is quaternized to obtain the bicationic quaternary ammonium salt of formula (I).

9. The process of claim 8 , wherein in the second step, the twin-tail triamine of formula (VII) is reacted with a dialkylsulfate wherein the alkyl groups in the dialkylsulfate have from 1 to 8 carbon atoms.

10. The process in accordance with claim 8 , further comprising a step wherein the internal ketone K1 of formula (V) is synthesized by a process P of decarboxylative ketonization reaction of a fatty acid, a fatty acid derivative or a mixture thereof in a liquid phase with a metal compound as catalyst in a reaction medium, said process P being characterized in that a ketone K2 at liquid state, which is identical or similar to the internal ketone K1, is introduced into the reaction medium.

11. The process of claim 9 , wherein the dialkylsulfate is dimethyl sulfate.

Assignees

• Rhodia Operations

Inventors

• Back Olivier
• Hong Bing
• Guirardel Matthieu

Classifications

• C07C211/63 Primary

  having quaternised nitrogen atoms bound to acyclic carbon atoms · CPC title

• C02F1/5272

  using specific organic precipitants · CPC title

• C02F1/547

  Tensides · CPC title

• C07C209/68

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title

• C02F1/56

  Macromolecular compounds · CPC title