Polyetheramines based on 1,3-dialcohols

Patent metadata

Field	Value
Publication number	US-10414856-B2
Application number	US-201515513637-A
Country	US
Kind code	B2
Filing date	Sep 10, 2015
Priority date	Sep 25, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

This invention relates to polyetheramines based on 1,3-dialcohols, in particular to an etheramine mixture comprising at least 90% by weight, based on the total weight of the etheramine mixture, of an amine of Formula (I) and/or (II),

wherein R 1 -R 12 are independently selected from H, alkyl, cycloalkyl, aryl, alkylaryl, or arylalkyl, wherein at least one of R 1 -R 6 and at least one of R 7 -R 12 is different from H, wherein A 1 -A 9 are independently selected from linear or branched alkylenes having 2 to 18 carbon atoms, wherein Z 1 -Z 4 are independently selected OH, CH 2 CH 2 CH 2 NH 2 , NH 2 , NHR′ or NR′R″, wherein the degree of amination is <50%, wherein R′ and R″ are independently selected from alkylenes having 2-6 carbon atoms, and wherein the sum of x+y is in the range of from 2 to 200, wherein x≥1 and y≥1; and x 1 +y 1 is in the range of from 2 to 200.

First claim

The invention claimed is:

1. An etheramine mixture comprising at least 90% by weight, based on the total weight of the etheramine mixture, of an etheramine of at least one of Formula (I) and an etheramine of at least one of Formula (II),

wherein R1-R12 are independently selected from H, alkyl, cycloalkyl, aryl, alkylaryl, or arylalkyl, wherein at least one of R1-R6 and at least one of R7-R12 is different from H,
wherein A1-A9 are independently selected from one of linear or branched alkylenes having 2 to 18 carbon atoms, wherein Z1-Z4 are independently selected from OH, CH2CH2CH2NH2, NH2, NHR′ or NR′R″, wherein the degree of amination is <50%,
wherein R′ and R″ are independently selected from alkylenes having 2 to 6 carbon atoms, and wherein the sum of x+y is in the range of from 2 to 200, wherein x≥1 and y≥1; and
x1+y1 is in the range of from 2 to 200.

2. The etheramine mixture according to claim 1 , wherein the etheramine mixture comprises at least 95% by weight, based on the total weight of the etheramine mixture, of the etheramine of Formula (I) and the etheramine of Formula (II).

3. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), x+y is in the range of from 2 to 20.

4. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), x+y is in the range of from 3 to 20.

5. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), the degree of amination lies in the range of 30% to <50%.

6. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), A1-A9 are independently selected from the group consisting of ethylene, propylene, and butylene.

7. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), each of A1-A9 is propylene.

8. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), R1, R2, R5, R6, R7, R8, R11, and R12 are H and R3, R4, R9, and R10 are independently selected from C1-16 alkyl or aryl.

9. The etheramine mixture according to claim 1 , wherein in said etheramine of Formula (I) or Formula (II), R1, R2, R5, R6, R7, R8, R11, and R12 are H and R3, R4, R9, and R10 are independently selected from a butyl group, an ethyl group, a methyl group, a propyl group, or a phenyl group.

10. The etheramine mixture according to claim 1 , wherein in said etheramine Formula (I) or Formula (II), R3 and R9 are each an ethyl group, R1, R2, R5 R6, R7, R8, R11, R12 are each H, R4 and R10 are each a butyl group.

11. The etheramine mixture according to claim 1 , wherein the etheramine of each of Formula (I) and Formula (II) has a weight average molecular weight of about 290 to about 1000 grams/mole.

12. The etheramine mixture according to claim 1 , wherein the etheramine of each of Formula (I) and Formula (II) is reacted with an acid.

13. A process for the manufacture of an etheramine mixture comprising at least 90% by weight, based on the total weight of the etheramine mixture, of an etheramine of at least one of Formula (I) and an etheramine of at least one of Formula (II) according to claim 1 comprising the following steps:
a) reacting a 1,3-diol of Formula (III) with C2-C18 alkylene oxides, wherein the molar ratio of 1,3-diol to C2-C18 alkylene oxides is in the range of 1:2 to 1:10,

wherein R1-R6 are independently of one another H, alkyl, cycloalkyl, aryl, alkylaryl, or arylalkyl and at least one group selected from R1-R6 is different from H, followed by one of:
b1) aminating the alkoxylated 1, 3-diols with ammonia, and
b2) reductive cyanoethylation of the alkoxylated 1, 3-diols.

14. The process according to claim 13 , wherein the molar ratio of 1,3-diol to C2-C18 alkylene oxides is in the range of 1:3 to 1:8.

15. The process according to claim 13 , wherein the molar ratio of 1,3-diol to C2-C18 alkylene oxides is in the range of 1:4 to 1:6.

16. The process according to claim 13 , wherein the C2-C18 alkylene oxides are selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and a mixture thereof.

17. The process according to claim 13 , wherein the C2-C18 alkylene oxide is propylene oxide.

18. The process according to claim 13 , wherein the 1,3-diol of formula (III) is selected from the group consisting of 2-butyl-2-ethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-methyl-2-phenyl-1,3-propanediol, 2,2-dimethyl-1,3-propandiol, and 2-ethyl-1,3-hexandiol.

19. The process according to claim 13 , wherein the amination is carried out in the presence of copper-, nickel- or cobalt-containing catalyst.

20. The process according to claim 19 , wherein the catalytically active material of the catalysts, 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.

21. A composition for use in at least one of personal care, shampoo, and body wash formulations, the composition comprising the etheramine mixture of claim 1 .

22. A composition for use as a curing agent, the composition comprising the etheramine mixture of claim 1 .

23. A composition for use as a reactant in the production of polymers, the composition comprising the etheramine mixture of claim 1 .

24. A composition for use in at least one of polyurethanes, polyureas, and thermoplastic polyamide adhesives, the composition comprising the etheramine mixture of claim 1 .

Assignees

• Basf Se

Inventors

• Ebert Sophia
• Ludolph Bjoern
• Eidamshaus Christian
• Scialla Stefano
• Christmas Kevin
• Eichstadt Waun Amy
• Loughnane Brian J
• Rees Darren
• Huelskoetter Frank

Classifications

• C09J177/06

  Polyamides derived from polyamines and polycarboxylic acids (C09J177/10 takes precedence) · CPC title

• B29C33/56

  Coatings {, e.g. enameled or galvanised}; Releasing, lubricating or separating agents {(in-mould coating B29C37/0028; using or applying separating agents B29C37/0067)} · CPC title

• C08G18/5024 Primary

  containing primary and/or secondary amino groups · CPC title

• C08G65/3255

  Ammonia · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title