Compositions containing an etheramine

Patent metadata

Field	Value
Publication number	US-11274267-B2
Application number	US-202016796344-A
Country	US
Kind code	B2
Filing date	Feb 20, 2020
Priority date	Mar 24, 2016
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

The present disclosure relates generally to cleaning compositions and, more specifically, to cleaning compositions containing an etheramine that is suitable for removal of stains from soiled materials.

First claim

What is claimed is:

1. A method of forming an etheramine:
the method comprising reductive cyanoethylation of an alkoxylated 1,3-diol mixture with an acrylonitrile in the presence of a base followed by hydrogentation with hydrogen and a catalyst to form an etheramine of Formula (I), Formula (II), or a mixture thereof:

wherein each of R 1 -R 12 is 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, each of A 1 -A 9 is independently selected from linear or branched alkanediyl groups having 2 to 18 carbon atoms, wherein each of Z 1 -Z 4 is independently selected from —OH and linear —OCH 2 CH 2 CH 2 NH 2 , wherein the degree of amination of each of the etheramines of Formula (I) and Formula (II) is equal to or greater than 50%, wherein the sum of x+y is in the range of about 2 to about 200, wherein x≥1 and y≥1, and the sum of x 1 +y 1 is in the range of about 2 to about 200.

2. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises an A 1 -A 9 that is independently selected from linear or branched alkanediyl groups having 2-10 carbon atoms, most preferably 2-5 carbon atoms.

3. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises an A 1 -A 9 that is independently selected from linear or branched alkanediyl groups having 2-5 carbon atoms.

4. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises a sum of x+y is in the range of about 2 to about 20.

5. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises a sum of x 1 +y 1 is in the range of about 2 to about 20.

6. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises an A 1 -A 9 that is independently selected from linear or branched alkanediyl groups having 2-5 carbon atoms, wherein the sum of x+y is in the range of about about 2 to about 10, and wherein the sum of x 1 +y 1 is in the range of about 2 to about 10, wherein x 1 ≥1 and y 1 ≥1.

7. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises a degree of amination of said etheramine of Formula (I) and/or Formula (II) is equal to or greater than about 55%.

8. The method of claim 1 , wherein in said etheramine of Formula (I) or Formula (II), x+y is in the range of about 2 to about 8 and x 1 +y 1 is in the range of about 2 to about 8.

9. The method of claim 1 , wherein the etheramine of Formula (I), Formula (II), or a mixture thereof comprises an etheramine mixture comprising at least 95%, more preferably at least 90%, by weight of said etheramine mixture, of said etheramine of Formula (I), said etheramine of Formula(II), or a mixture thereof.

10. The method of claim 1 , wherein in said etheramine of Formula (I) or Formula (II), each of A 1 -A 9 is independently selected from the group consisting of ethylene, propylene, butylene, and mixtures thereof, preferably each of A 1 -A 9 is propylene.

11. The method of claim 1 , wherein in said etheramine of Formula (I) or Formula (II), each of R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 11 , and R 12 is H and each of R 3 , R 4 , R 9 , and R 10 is independently selected from C1-C16 alkyl or aryl, preferably each of R 3 , R 4 , R 9 , and R 10 is independently selected from a butyl group, an ethyl group, a methyl group, a propyl group, or a phenyl group.

12. The method of claim 1 , wherein in said etheramine of Formula (I) or Formula (II), each of R 3 and R 9 is an ethyl group, each of R 4 and R 10 is a butyl group, and each of R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 11 , and R 12 is H.

13. The method of claim 1 , wherein in said etheramine of Formula (I) or Formula (II), each of R 1 , R 2 , R 7 , and R 8 is H and each of R 3 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , and R 12 is independently selected from an ethyl group, a methyl group, a propyl group, a butyl group, a phenyl group, or H.

14. The method of claim 1 , wherein said etheramine has a weight average molecular weight of about 290 to about 1000 grams/mole.

15. The method of claim 1 , wherein said etheramine has a weight average molecular weight of about 290 to about 900 grams/mole.

16. The method of claim 1 , wherein said etheramine has a weight average molecular weight of about 300 to about 450 grams/mole.

17. The method of claim 1 , wherein the base comprises alkaline hydroxides and substituted ammonium hydroxide.

18. The method of claim 1 , wherein the catalyst for hydrogenation of the nitrile function to the corresponding amine comprises one or more of Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, or Pt.

Assignees

• Procter & Gamble

Inventors

• Scialla Stefano
• Loughnane Brian Joseph
• HENKE Karie Marie
• Frankenbach Gayle Marie
• Nash Jr J Frank
• Hayes Michael Patrick
• Venegas Manuel G
• Ludolph Bjoern
• Ebert Sophia Rosa
• Eidamshaus Christian
• Davis Jan Richard
• Fairweather Neil Thomas

Classifications

• G06F30/392

  Floor-planning or layout, e.g. partitioning or placement · CPC title

• C11D17/042

  Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions · CPC title

• C11D3/3723

  Polyamines or polyalkyleneimines · CPC title

• C11D1/72

  Ethers of polyoxyalkylene glycols · CPC title

• C11D3/30 Primary

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