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US 11,566,107 B2Granted
Etheramine mixture containing polyether diamines and method of making and using the same
AssigneeHuntsman Petrochemical Corporation
InventorsHoward P. Klein, Terry L. Renken, Cheng-Kuang Li
Life of this patent
Estimating the term…
Abstract
An etheramine mixture comprising one or more polyether diamines, methods for its production, and its use as a curing agent for epoxy resins. The etheramine mixture may also be used in the preparation of polyamides and polyurea compounds.
Claims19
An etheramine mixture comprising:
- one or more polyether diamines of formula (I):
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 0 to 9 with the caveat that if one of x or y is 0, then the other is in a range of from 1 to 9;
- and the sum of x and y is in a range of from 1 to 10;
- at least one or more polyether diamines of formula (III):
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 1 to 9;
- and the sum of x and y is in a range of from 2 to 10;
- and
- less than 10 wt. % of a monoether diamine based on the total weight of the etheramine mixture.
11 more elements
A method for producing an etheramine mixture, comprising:
- charging a hydrophobic diol to an alkoxylation reaction zone;
- contacting the hydrophobic diol with an ethylene oxide in the alkoxylation reaction zone to provide a precursor diol, wherein the ratio of moles of ethylene oxide to hydrophobic diol is in a range of from greater than 2:1 to 10:1;
- and
- charging the precursor diol to a reductive amination zone and reductively aminating the precursor diol to form an etheramine mixture containing one or more polyether diamines of formula (I):
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 0 to 9 with the caveat that if one of x or y is 0, then the other is in a range of from 1 to 9;
- and the sum of x and y is in a range of from 1 to 10;
- one or more polyether diamines of the formula (III)
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 1 to 9;
- and the sum of x and y is in a range of from 2 to 10;
- and
- less than 10 wt. % of monoether diamine based on the total weight of the etheramine mixture.
14 more elements
An etheramine mixture produced by a method comprising the steps of:
- charging a hydrophobic diol to an alkoxylation reaction zone;
- contacting the hydrophobic diol with an ethylene oxide in the alkoxylation reaction zone to provide a precursor diol, wherein the ratio of moles of ethylene oxide to hydrophobic diol is in a range of from greater than 2:1 to 10:1;
- and
- charging the precursor diol to a reductive amination zone and reductively aminating the precursor diol to form the etheramine mixture containing one or more polyether diamines of formula (I):
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 0 to 9 with the caveat that if one of x or y is 0, then the other is in a range from 1 to 9;
- and the sum of x and y is in a range of from 1 to 10;
- one or more polyether diamines of the formula (III)
- wherein:
- R is a radical of a hydrophobic diol after removal of the two hydroxyl groups from the hydrophobic diol;
- n is in a range of from 1 to 3;
- x and y are each in a range of from 1 to 9;
- and the sum of x and y is in a range of from 2 to 10;
- and
- less than 10 wt. % of monoether diamine based on the total weight of the etheramine mixture.
14 more elements
Dependencies are inferred from the claim text.