Salts of etheramines and polymeric acid

1. A salt of a hydrophobic etheramine and of a polymeric acid, wherein the hydrophobic etheramine is selected from the group consisting of an etheramine of formula (I), an etheramine of formula (II),

and a mixture of etheramines of formula (I) and formula (II), and wherein R 1 -R 12 are independently selected from H, alkyl, cycloalkyl, aryl, alkylaryl, or arylalkyl,

at least one of R 1 —R 6 and at least one of R 7 -R 12 is different from H,

A 1 -A 9 are independently from each other linear or branched propylene or linear or branched butylene,

the sum of x+y is in the range of from 2 to 200,

x≥1 and y≥1,

and x 1 +y 1 is in the range of from 2 to 200, x 1 ≥1 and y 1 ≥1.

2. The salt according to claim 1 , wherein each of A 1 -A 9 is one of a linear or a branched propylene.

3. The salt according to claim 1 , wherein R 3 and R 9 are each an ethyl group, R 1 , R 2 , R 5 R 6 , R 7 , R 8 , R 11 , R 12 are each H, and R 4 and R 10 are each a butyl group.

4. The salt according to claim 1 , wherein the polymeric acid is a polyacrylic acid with a molecular weight (Mw) of from 1,000 g/mol to 1,000,000 g/mol determined by gel permeation chromatography and referring to the free acid.

5. The salt according to claim 1 , wherein the polymeric acid is a copolymer of acrylic acid and maleic acid with a molecular weight of from 1,000 g/mol to 1,000,000 g/mol.

6. A salt of a hydrophobic etheramine and of a polymeric acid, wherein the hydrophobic etheramine is an etheramine of formula (IV),

wherein R═H or ethyl, k=0 or 1, A represents at least one of (a) one of a linear or a branched propylene and (b) one of a linear or a branched butylene group, wherein A may be the same as or different from one another, the sum of x, y and z lies in the range of 3 to 100, x≥1, y≥1 and z≥1.

7. A salt of a hydrophobic etheramine and of a polymeric acid, wherein the hydrophobic etheramine is selected from the group consisting of an etheramine of formula (V), an etheramine of formula (VI),

and a mixture of etheramines of formula (V) and formula (VI) and wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H and one of a linear or branched alkyl group with 2 to 16 carbon atoms; A 1 , A 2 , A 3 and A 4 are independently selected from at least one of (a) a linear or branched propylene and (b) one of a linear or branched butylene, the sum of x+y is in the range of 2 to 100 and x≥1 and y≥1.

8. The salt according to claim 7 , wherein A 1 , A 2 , A 3 and A 4 are propylene.

9. The salt according to claim 7 , wherein R 1 is a linear alkyl group with 2 to 8 carbon atoms and R 2 , R 3 and R 4 are hydrogens.

10. The salt according to claim 7 , wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, a methyl group and an ethyl group and A 1 , A 2 , A 3 and A 4 are one of linear or branched butylene.

11. The salt according to claim 10 , wherein the polymeric acid is one of a homopolymer of a carboxylic acid or a copolymer of acrylic acid and maleic acid.

12. A salt of a hydrophobic etheramine and of a polymeric acid obtainable by a process comprising the following steps:

a) the reaction of 1,3-diols of formula (III) with at least one of propylene oxide and butylene oxide, wherein the molar ratio of 1,3-diol to propylene oxide and/or butylene oxide is in the range of 1:2 to 1:10,

with R 1 -R 6 are independently of one another H, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl and at least one group selected from R 1 -R 6 is different from H (compound A),

b) the amination of the alkoxylated 1,3-diols (compound A) with ammonia in the presence of a catalysator (compound B),

c) the mixing of compound B to an aqueous solution of a polymeric acid at 25° C., wherein the molar ratio of the polycarboxylic acid groups to amino groups in compound B lies in the range of 100:1 to 1:1,

d) the removal of the water from the aqueous solution by one of spray-drying using a gas with an inlet temperature of at least 125° C. spray granulation using a gas with an inlet temperature of at least 125° C. distillation under reduced pressure, and phase separation followed by distillation.

13. The salt of claim 12 , wherein the process further comprises milling the resulting solid.

14. A salt of a hydrophobic etheramine and of a polymeric acid obtainable by a process comprising the following steps:

a) the reaction of glycerine or 1,1,1-trimethylolpropane with at least one of butylene oxide and propylene oxide, wherein the molar ratio of glycerine or 1,1,1-trimethylolpropane to butylene oxide and/or propylene oxide is in the range of 1:3 to 1:10 (compound C),

b) the amination of the alkoxylated glycerine or 1,1,1-trimethylolpropane (compound A) with ammonia in the presence of a catalysator (compound D),

c) the mixing of compound D to an aqueous solution of a polymeric acid at 25° C., wherein the molar ratio of the polycarboxylic acid groups to amino groups in compound B lies in the range of 100:1 to 1:1,

d) the removal of the water from the aqueous solution by one of spray-drying using a gas with an inlet temperature of at least 125° C. spray granulation using a gas with an inlet temperature of at least 125° C. distillation under reduced pressure, and phase separation followed by distillation.

15. The salt of claim 14 , wherein the process further comprises milling the resulting solid.

16. A salt of a hydrophobic etheramine and of a polymeric acid obtainable by a process comprising the following steps:

a) the reaction of 1,2-dialcohols of formula (VII) with at least one of propylene oxide and butylene oxide, wherein the molar ratio of 1,2-dialcohol to propylene oxide and/or butylene oxide is in the range of 1:2 to 1:100,

wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H and a linear or branched alkyl group with 2 to 16 carbon atoms (compound E),

b) the amination of the alkoxylated 1,2-dialcohol (compound E) with ammonia in the presence of a catalysator (compound F),

c) the mixing of compound F to an aqueous solution of a polymeric acid at 25° C., wherein the molar ratio of the polycarboxylic acid groups to amino groups in compound B lies in the range of 100:1 to 1:1,

d) the removal of the water from the aqueous solution by one of spray-drying using a gas with an inlet temperature of at least 125° C. spray granulation using a gas with an inlet temperature of at least 125° C. distillation under reduced pressure, and or by phase separation followed by distillation.

17. The salt of claim 16 , wherein the process further comprises milling the resulting solid.