Etheramines prepared from a mixture of two or more multifunctional alcohol initiators, and their use as curatives or intermediates for polymer synthesis

Patent metadata

Field	Value
Publication number	US-11292873-B2
Application number	US-201916668006-A
Country	US
Kind code	B2
Filing date	Oct 30, 2019
Priority date	Nov 5, 2013
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

Implementations described herein generally relate to etheramine mixtures formed from a mixture of two or more multifunctional alcohol initiators, processes for the etheramine mixtures production, and its use as a curing agent or as a raw material in the synthesis of polymers. In one implementation, the process comprises mixing a polyol initiator having a melting point greater than a processing temperature and a polyol initiator having a melting point less than the processing temperature to form a polyol initiator mixture having a melting point less than the processing temperature, charging the polyol initiator mixture to an alkoxylation reaction zone, contacting the polyol initiator mixture with an alkylene oxide in the alkoxylation reaction zone to provide a mixture of alkoxylated precursor polyols and charging the mixture of alkoxylated precursor polyols to a reductive amination zone and reductively aminating the mixture of alkoxylated precursor polyols to form the etheramine mixture.

First claim

The invention claimed is:

1. A composition comprising an etheramine mixture that comprises the reaction product of ammonia and a mixture of alkoxylated precursor polyols;
wherein the reaction is conducted under reductive amination reaction conditions;
wherein the mixture of alkoxylated polyols is the reaction product of a polyol initiator mixture having a melting point less than a processing temperature with an alkylene oxide; and
wherein the polyol initiator mixture comprises a first polyol initiator having a melting point greater than the processing temperature and a second polyol initiator having a melting point less than the processing temperature,
wherein the etheramine mixture comprises an etheramine of formula (I):

wherein R 5 and R 6 are identical or different and are each, independently of one another, hydrogen, a linear or branched C 1 to C 5 alkyl group, a linear or branched C 2 -C 5 alkenyl group, or a substituted or unsubstituted C 6 -C 12 aryl group and m+n equals a non-zero whole number between one and six, and
wherein the etheramine mixture further comprises

wherein R 9 and R 10 are identical or different and are each, independently of one another, hydrogen, a linear or branched C 1 to C 5 alkyl group, a linear or branched C 2 -C 5 alkenyl group, or a substituted or unsubstituted C 6 -C 12 aryl group and x+y equals a non-zero whole number between one and six.

2. The composition of claim 1 , wherein the weight ratio of the first polyol initiator to the second polyol initiator is between 30:70 and 90:10.

3. The composition of claim 2 , wherein the composition is clear and has a melting point of 60° C. or less.

4. The composition of claim 1 , wherein the composition is an epoxy resin system.

5. The composition of claim 1 , wherein the first polyol initiator is a solid and the second polyol initiator is a liquid at processing temperatures.

6. The composition of claim 5 , wherein the polyol initiator mixture is a liquid at processing temperatures.

7. A composition comprising:

wherein R 5 and R 6 are identical or different and are each, independently of one another, hydrogen, a linear or branched C 1 to C 5 alkyl group, a linear or branched C 2 -C 5 alkenyl group, or a substituted or unsubstituted C 6 -C 12 aryl group and m+n equals a non-zero whole number between one and six; and

wherein R 9 and R 10 are identical or different and are each, independently of one another, hydrogen, a linear or branched C 1 to C 5 alkyl group, a linear or branched C 2 -C 5 alkenyl group, or a substituted or unsubstituted C 6 -C 12 aryl group and x+y equals a non-zero whole number between one and six.

8. The composition of claim 7 , comprising:
from about 10% by weight to about 90% by weight of the etheramine of formula (I), based on the total weight of the composition; and
from about 10% by weight to about 90% by weight of the at least one etheramine of formula (III), based on the total weight of the composition.

Assignees

• Huntsman Petrochemical Llc

Inventors

• Zhou Hui
• Lewis David C
• Klein Howard P
• Renken Terry L
• Patterson Leah

Classifications

• C08G18/3234

  cycloaliphatic · CPC title

• C08G59/504 Primary

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title

• C08G2650/50

  containing nitrogen, e.g. polyetheramines or Jeffamines(r) · CPC title

• C07C217/42

  having etherified hydroxy groups and at least two amino groups bound to the carbon skeleton · CPC title