Etheramines based on 1,2-dialcohols

Patent metadata

Field	Value
Publication number	US-9974985-B2
Application number	US-201514710845-A
Country	US
Kind code	B2
Filing date	May 13, 2015
Priority date	May 15, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The invention relates to etheramines of formula (I) or formula (II) or a mixture of etheramines of formula (I) and formula (II) based on 1,2-dialcohols, wherein R 1 is a linear or branched alkyl group with 2 to 16 carbon atoms, R 2 is a hydrogen or an alkyl group with 1 to 16 carbon atoms, x≥1 and y≥1 and the sum of x+y is between 2 and 10, and A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of linear and/or branched alkylenes having 2 to 18 carbon atoms and wherein 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.

The invention further relates to etheramines obtainable by the alkoxylation and amination of 1,2-dialcohols.

First claim

The invention claimed is:

1. A composition comprising etheramines of formula (I) and formula (II),

wherein
R 1 is a linear or branched alkyl group with 2 to 16 carbon atoms,
R 2 is a hydrogen or an alkyl group with 1 to 16 carbon atoms,
x≥1 and y≥1 and the sum of x+y is between 2 and 10, and
A 1 , A 2 , A 3 and A 4 are independently selected from the group consisting of linear and/or branched alkylenes having 2 to 18 carbon atoms,
wherein Z 1 -Z 4 are independently selected from OH, NH 2 , NHR′ or NR′R″, wherein at least one of Z 1 or Z 2 and at least one of Z 3 or 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 composition according to claim 1 , wherein A 1 , A 2 , A 3 and A 4 are independently selected from 1,2-propylene or 1,2-butylene.

3. The composition according to claim 1 , wherein A 1 , A 2 , A 3 and A 4 are each 1,2-propylene.

4. The composition according to claim 1 , wherein x+y is in the range of from 3 to 6.

5. The composition according to claim 1 , wherein R 1 is a linear or branched alkyl group with 3 to 16 carbon atoms and R 2 is hydrogen or an alkyl group with 1 to 16 carbon atoms.

6. The composition according to claim 1 , wherein R 1 is a linear alkyl group with 3 to 8 carbon atoms and R 2 is hydrogen.

7. The composition according to claim 1 , wherein Z 1 to Z 4 are each NH 2 .

8. The composition according to claim 1 , wherein the etheramine of formula (I) and formula (II) has a weight average molecular weight of from about 270 to about 1000 grams/mole.

9. The composition according to claim 1 , wherein the etheramines of formula (I) and formula (II) are reacted with an acid.

10. A process for the manufacture of a composition comprising etheramines of formula (I) and formula (II) according to claim 1 comprising the following steps:
alkoxylation of a 1,2-dialcohol of formula (III) with C 2 -C 18 alkylene oxides, wherein the molar ratio of the 1,2-dialcohol of formula (III) to C 2 -C 18 alkylene oxides is in the range of 1:2 to 1:10,

wherein R 1 is a linear or branched alkyl group with 3 to 16 carbon atoms and R 2 is a hydrogen or an alkyl group with 1 to 16 carbon atoms,
amination of the alkoxylated 1,2-dialcohol with ammonia.

11. The process according to claim 10 , wherein the molar ratio of 1,2-dialcohol to C 2 -C 18 alkylene oxides is in the range of 1:3 to 1:8.

12. The process according to claim 10 , wherein the molar ratio of 1,2-dialcohol to C 2 -C 18 alkylene oxides is in the range of 1:4 to 1:6.

13. The process according to claim 10 , wherein the C 2 -C 18 alkylene oxides are selected from propylene oxide, butylene oxide or a mixture thereof.

14. The process according to claim 10 , wherein the C 2 -C 18 alkylene oxide is propylene oxide.

15. The process according to claim 10 , wherein the 1,2-dialcohol of formula (III) is selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-dodecanediol, 1,2-tetradecandiol, 1,2 hexadecandiol and 1,2 octadecandiol.

16. The process according to claim 10 , wherein the amination is carried out in the presence of a catalyst that comprises at least one of copper, nickel or cobalt.

17. The process according to claim 16 , wherein the catalyst, before the reduction thereof with hydrogen, comprises oxygen compounds of aluminum, of copper, of nickel and of cobalt, and in the range from 0.2 to 5.0% by weight of oxygen compounds of tin, calculated as SnO.

18. A personal care product comprising the composition of claim 1 .

19. The personal care product of claim 18 selected from a shampoo or a body wash formulation.

20. A curing agent for epoxy resins comprising the composition of claim 1 .

21. A polymer selected from a polyurethane, a polyurea, or a thermoplastic polyamide adhesive comprising the composition of claim 1 .

22. A composition comprising etheramines of formula (I) and formula (II),

wherein
R 1 is a linear or branched alkyl group with 2 to 16 carbon atoms,
R 2 is a hydrogen or an alkyl group with 1 to 16 carbon atoms,
x≥1 and y≥1 and the sum of x+y is between 2 and 10, and
A 1 , A 2 , A 3 and A 4 are independently selected from 1,2-propylene or 1,2-butylene, and at least one of A 1 , A 2 , A 3 or A 4 is 1,2-propylene,
wherein Z 1 to Z 4 are independently selected from OH, NH 2 , NHR′ or NR′R″, wherein at least one of Z 1 or Z 2 and at least one of Z 3 or Z 4 is NH 2 , NHR′ or NR′R″, wherein R′ and R″ are independently selected from alkylenes having 2 to 6 carbon atoms.

23. The composition according to claim 22 , wherein A 1 , A 2 , A 3 and A 4 are each 1,2-propylene, and x+y is in the range of from 3 to 6.

24. The composition according to claim 23 , wherein R 1 is a linear alkyl group with 3 to 8 carbon atoms, R 2 is hydrogen, and Z 1 to Z 4 are each NH 2 .

Assignees

• Basf Se

Inventors

• Ebert Sophia
• Ludolph Björn
• Wigbers Christof Wilhelm
• Boeckh Dieter
• Huelskoetter Frank
• Scialla Stefano
• Christmas Kevin
• Rees Darren
• Loughnane Brian J

Classifications

• A61Q19/10 Primary

  Washing or bathing preparations · CPC title

• A61K8/45

  Derivatives containing from 2 to 10 oxyalkylene groups · CPC title

• C11D3/30

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

• C11D3/3723

  Polyamines or polyalkyleneimines · CPC title

• C07C217/46 Primary

  the carbon skeleton being acyclic and unsaturated · CPC title