Polyetheramines with low melting point

Patent metadata

Field	Value
Publication number	US-10266649-B2
Application number	US-201615544765-A
Country	US
Kind code	B2
Filing date	Jan 21, 2016
Priority date	Jan 26, 2015
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

Described herein are substituted polyetheramines with a low melting point which are obtainable by condensation of at least two N-(hydroxyalkyl)amines to obtain a polyetheramine and subsequent reaction of at least one remaining hydroxy group and/or, if present, at least one secondary amino group of said polyetheramine with ethylene oxide and at least one further alkylene oxide to obtain a substituted polyetheramine. Uses of such substituted polyetheramines in fields of cosmetic formulations, as crude oil emulsion brakers, in pigment dispersions of ink jets, in electro paintings, or in cementitious compositions as well as methods wherein said substituted polyetheramines are used in said fields are described herein.

First claim

The invention claimed is:

1. Substituted polyetheramine obtainable by
(a) Condensation of at least two N-(hydroxyalkyl)amines, wherein said N-(hydroxyalkyl)amines are independently selected from the group consisting of N-(hydroxyalkyl)amines according to formula la and Ib, respectively:

wherein
A is independently selected from the group consisting of linear C 1 -alkylene, branched C 1 -alkylene, linear C 2 -alkylene, branched C 2 -alkylene, linear C 3 -alkylene, branched C 3 -alkylene, linear C 4 -alkylene, branched C 4 -alkylene, linear C 5 -alkylene, branched C 5 -alkylene, linear C 6 -alkylene, and branched C 6 -alkylene, R 3 , R 3* , R 4 , R 4* , R 5 , R 5* , R 6 , R 6* , R 7 , R 7* and R 8 are independently selected from the group consisting of H; linear substituted alkyl; branched substituted alkyl; linear non-substituted alkyl; branched non-substituted alkyl; substituted acycloalkyl; non-substituted acycloalkyl; substituted aryl; and non-substituted aryl to obtain a polyetheramine; and
(b) reacting at least one of the following: (i) at least one remaining hydroxy group and, (ii) at least one secondary amino group of the polyetheramine obtained in (a) with ethylene oxide and at least one further alkylene oxide selected from the group consisting of propylene oxide, butylene oxide, and pentene oxide
to obtain a substituted polyetheramine which is substituted with at least one alkylenoxy unit E,
wherein E is an alkylenoxy unit according to formula II:

wherein

said —(R 1 —O) n — unit is an inner block;
R 1 is independently selected from the group consisting of 1,2-propylene, 1,2-butylene, and 1,2-pentene;
R 2 is independently selected from the group consisting of H, any of C 1 to C 22 alkyl, and any of C 7 to C 22 aralkyl
m is an integer independently selected from values in the range of from 5 to 18;
n is an integer independently selected from values in the range of from 1 to 5; and
p is an integer independently selected from values in the range of from 2 to 14.

2. Substituted polyetheramine according to claim 1 , wherein said substituted polyetheramine is further modified by at least one of quaternization, protonation, sulfation, transsulfation, and phosphation.

3. Substituted polyetheramine according to claim 1 , wherein A is a C 1 -alkylene.

4. Substituted polyetheramine according to claim 1 , wherein N-(hydroxyalkyl)amines according to formula la and not N-(hydroxyalkyl)amines according to formula lb are condensed.

5. Substituted polyetheramine according to claim 1 , wherein at least one of R 3 , R 3* , R 4 , R 4* , R 5 , R 5* , R 6 , R 6* , R 7 and R 7* is independently selected from the group consisting of H, methyl and ethyl.

6. Substituted polyetheramine according to claim 1 , wherein R 8 is selected from the group consisting of H, methyl, ethyl, and butyl.

7. Substituted polyetheramine according to claim 1 , wherein R 1 is 1,2-propylene.

8. Substituted polyetheramine according to claim 1 , wherein R 2 is one of H, C 1 alkyl, C 2 alkyl, C 3 alkyl, and C 4 alkyl.

9. Substituted polyetheramine according to claim 1 , wherein m is 10 to 12.

10. Substituted polyetheramine according to claim 2 , wherein said substituted polyetheramine is further modified by at least one of quaternization and quaternization with additional sulfation.

11. Substituted polyetheramine according to claim 1 , wherein R 3* , R 4* , R 5* R 6* , and R 7* are H, and R 3 , R 4 , R 5 , R 6 , R 7 are one of H and methyl.

12. Substituted polyetheramine according to claim 1 , wherein n is 2 to 3.

13. Substituted polyetheramine according to claim 1 , wherein p is 8 to 9.

Assignees

• Basf Se
• Procter & Gamble

Inventors

• Ebert Sophia
• Ludolph Bjoern
• Loughnane Brian J

Classifications

• C10G33/04

  with chemical means · CPC title

• C08G65/26

  from cyclic ethers and other compounds · CPC title

• C11D1/44

  Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines · CPC title

• C08G73/02

  Polyamines · CPC title

• B01D17/04

  Breaking emulsions · CPC title