Etheramines based on dialcohols

Patent metadata

Field	Value
Publication number	US-10414719-B2
Application number	US-201515129169-A
Country	US
Kind code	B2
Filing date	Mar 11, 2015
Priority date	Mar 27, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

This invention relates to etheramines based on dialcohols, wherein the etheramines comprise at least three linear or branched C4-alkylene groups and a process for the manufacture of these etheramines.

First claim

The invention claimed is:

1. A mixture of etheramines of formula (I)

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;
A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of linear alkylenes having 2 to 18 carbon atoms and branched alkylenes having 2 to 18 carbon atoms;
wherein at least three selected from the group consisting of A 1 , A 2 , A 3 and A 4 are linear or branched butylene;
the sum of x+y is in the range of 3 to 100 and x≥1 and y≥1;
Z 1 -Z 4 are independently selected from OH, NH 2 , NHR′ or NR′R″, wherein at least one of Z 1 -Z 2 and at least one of Z 3 -Z 4 is NH 2 , NHR′ or NR′R″, wherein R′ and R″ are independently selected from alkylenes having 2 to 6 carbon atoms.

2. The mixture according to claim 1 , wherein x+y is in the range of from 3 to 10.

3. The mixture according to claim 1 , wherein A 1 , A 2 , A 3 and A 4 are linear or branched butylene.

4. The mixture according to claim 1 , wherein R 1 is a methyl group and R 2 , R 3 and R 4 are H.

5. The mixture according to claim 1 , wherein Z 1 -Z 4 are NH 2 .

6. The mixture according to claim 1 , wherein said etheramine of formula (I) or formula (II) has a weight average molecular weight of about 250 to about 700 grams/mole.

7. A composition comprising the mixture as defined in claim 1 and further comprises an etheramine of formula (VI)

and/or an etheramine of formula (VII)

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;
A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of linear alkylenes having 2 to 18 carbon atoms and branched alkylenes having 2 to 18 carbon atoms;
wherein at least one of A 1 , A 2 , A 3 and A 4 is linear or branched butylene;
the sum of k+m is below 3 and wherein k≥1 and m≥1;
Z 1 -Z 4 are independently selected from OH, NH 2 , NHR′ or NR′R″, wherein at least one of Z 1 -Z 2 and at least one of Z 3 -Z 4 is NH 2 , NHR′ or NR′R″, wherein R′ and R″ are independently selected from alkylenes having 2 to 6 carbon atoms.

8. The mixture according to claim 1 , wherein the etheramine mixture is reacted with an acid.

9. A process for the manufacture of the mixture as defined in claim 1 comprising the following steps:
a) reacting a dialcohol of Formula (III) with C 2 -C 18 alkylene oxides, wherein the molar ratio of dialcohol to C 2 -C 18 alkylene oxides is in the range of from 1:3 to 1:10,

wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, a methyl group or an ethyl group; and

b) aminating the alkoxylated dialcohols with ammonia.

10. The process according to claim 9 , wherein the molar ratio of dialcohol to C 2 -C 18 alkylene oxides is in the range of 1:3 to 1:4.

11. The process according to claim 9 , wherein the C 2 -C 18 alkylene oxides are selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide or a mixture thereof.

12. The process according to claim 9 , wherein the C 2 -C 18 alkylene oxide is butylene oxide.

13. The process according to claim 9 , wherein the dialcohol of formula (III) is selected from the group consisting of 1,2-propanediol, 1,2-butanediol, 1,2-ethanediol, 3,4-hexanediol and 2,3-pentanediol.

14. The process according to claim 9 , wherein the amination is carried out in the presence of copper-containing catalyst, nickel-containing catalyst or cobalt-containing catalyst.

15. A personal care composition comprising the mixture as defined in claim 1 .

16. A shampoo and/or body wash formulation comprising the mixture as defined in claim 1 .

17. A curing agent for epoxy resins or as a reactant in the production of polymers comprising the mixture as defined in claim 1 .

18. A polyurethane, polyurea, or a thermoplastic polyamide adhesives comprising the mixture as defined in claim 1 .

19. The mixture according to claim 3 , wherein R 1 is a methyl group and R 2 , R 3 and R 4 are H and Z 1 -Z 4 are NH 2 .

Assignees

• Basf Se

Inventors

• Ebert Sophia
• Ludolph Björn
• Wigbers Christof W
• Eidamshaus Christian
• Boeckh Dieter
• Huelskoetter Frank
• Loughnane Brian J
• Eichstadt Waun Amy
• Christmas Kevin
• Rees Darren
• Scialla Stefano

Classifications

• C08G18/3228

  acyclic · CPC title

• A61K8/45

  Derivatives containing from 2 to 10 oxyalkylene groups · CPC title

• C11D3/30

  Amines; Substituted amines {; Quaternized amines} · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• C07C217/08 Primary

  the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom · CPC title