Etheramine mixture containing polyether diamines and method of making and using the same

1. 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.

2. The etheramine mixture of claim 1 , wherein 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 for each of the one or more polyether diamines of formula (I) and formula (III).

3. The etheramine mixture of claim 1 , wherein the hydrophobic diol has 6 to 15 carbon atoms for each of the one or more polyether diamines of formula (I) and formula (III).

4. The etheramine mixture of claim 3 , wherein the hydrophobic diol is selected from a cycloaliphatic diol, a hydrogenated aromatic diol, a linear alkyl diol, or a combination thereof.

5. The etheramine mixture of claim 3 , wherein the hydrophobic diol is a cyclopentane diol or a cyclohexane diol.

6. The etheramine mixture of claim 1 , wherein the sum of x and y is in a range of from 3 to 6 for each of the one or more polyether diamines of formula (I) and formula (III).

7. The etheramine mixture of claim 1 , wherein at least 60% of the amine groups of the one or more polyether diamines of formula (I) are primary amines.

8. 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.

9. The method of claim 8 , wherein 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 for each of the one or more polyether diamines of formula (I) and formula (III).

10. The method of claim 8 , wherein the hydrophobic diol has 6 to 15 carbon atoms for each of the one or more polyether diamines of formula (I) and formula (III).

11. The method of claim 10 , wherein the hydrophobic diol is selected from a cycloaliphatic diol, a hydrogenated aromatic diol, a linear alkyl diol, or a combination thereof.

12. A method for producing an epoxy resin system, comprising:

providing the etheramine mixture of claim 1 ;

providing an epoxy resin;

contacting the etheramine mixture and the epoxy resin to form an epoxy resin system.

13. A method for producing a cured epoxy resin system, comprising:

providing an etheramine mixture of claim 1 ;

providing an epoxy resin;

contacting the etheramine mixture and the epoxy resin to form an epoxy resin system; and

curing the epoxy resin system.

14. The method of claim 13 , wherein the step of curing the epoxy resin system comprises subjecting the epoxy resin system to a temperature ranging from about 5° C. to 30° C. for a time ranging from 6 to 24 hours.

15. A method for producing a polyurea comprising reacting the etheramine mixture of claim 1 with an organic polyisocyanate.

16. A polyurea produced by the method of claim 15 .

17. 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.

18. The mixture of claim 17 , wherein 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 for each of the one or more polyether diamines of formula (I) and (formula (III).

19. A composite formed by the method of claim 13 .