Imidazoline functionalized oxidized fatty substance emulsifiers and methods

Patent metadata

Field	Value
Publication number	US-2017306067-A1
Application number	US-201515520707-A
Country	US
Kind code	A1
Filing date	Oct 23, 2015
Priority date	Oct 23, 2014
Publication date	Oct 26, 2017
Grant date	—

Abstract

Imidazoline functionalized oxidized fatty substance emulsifiers are made by obtaining a fatty substance composition; performing an oxidative oligomerization of the fatty substance composition to produce an oxidized fatty substance composition comprising from about 10 to about 75% by weight of oligomeric fatty acid components based on the total weight of fatty acid containing components in the composition; reacting the oxidized fatty substance composition with a polyamine comprising at least one ethylene diamine functional group with at least three hydrogens attached to the two nitrogens to form an aminoethylamido functionalized oxidized fatty substance composition; and forming an imidazoline functionalized oxidized fatty substance emulsifier from the amino-ethylamido functionalized oxidized fatty substance composition. Such compositions are particularly useful in asphalt applications and corrosion inhibition.

First claim

1 . A method for making an imidazoline functionalized oxidized fatty substance emulsifier comprising the steps of:
(a) obtaining a fatty substance composition; (b) performing an oxidative oligomerization of the fatty substance composition to produce an oxidized fatty substance composition comprising from about 10 to about 75% by weight of oligomeric fatty acid components based on the total weight of fatty acid containing components in the composition; (c) reacting the oxidized fatty substance composition with a polyamine comprising at least one ethylene diamine functional group with at least three hydrogens attached to the two nitrogens to form an aminoethylamido functionalized oxidized fatty substance composition; and (d) forming an imidazoline functionalized oxidized fatty substance emulsifier from the aminoethylamido functionalized oxidized fatty substance composition.

2 . The method of claim 1 , wherein the oxidative oligomerization step comprises the steps
(b-1) heating the fatty substance composition; and (b-2) passing an oxygen-containing stream through the heated fatty substance composition to produce the oxidized fatty substance composition.

3 . The method of claim 1 , wherein the oxidized fatty substance composition comprises a trimodal molecular weight distribution of the fatty acid containing components.

4 . The method of claim 1 , wherein the oxidized fatty substance composition comprises
a trimodal molecular weight distribution of fatty acid containing components, wherein about 30 to about 70% by weight of fatty acid compounds in the oxidized fatty substance composition are in the low molecular weight range of the trimodal molecular weight distribution, about 10 to about 30% by weight of fatty acid compounds in the oxidized fatty substance composition are in the medium molecular weight range of the trimodal molecular weight distribution, and about 10 to about 65% by weight of fatty acid compounds in the oxidized fatty substance composition are in the high molecular weight range of the trimodal molecular weight distribution.

5 . The method of claim 1 , wherein the oxidized fatty substance composition comprises from about 30 to about 70% by weight of compounds having a fatty acid component that are monomers; from about 5 to about 20% by weight of compounds having a fatty acid component that are dimers, and from about 5 to about 65% by weight of compounds having a fatty acid component having three or more mers, based on the total amount of compounds having a fatty acid component in the oxidized fatty substance composition.

6 . The method of claim 5 , wherein
the monomers of the oxidized fatty substance composition have an average molecular weight ranging from about 200 to about 1000 (g/mol), the dimers of the oxidized fatty substance composition have an average molecular weight ranging from about 600 to about 2000 (g/mol), and the compounds having three or more mers of the oxidized fatty substance composition have an average molecular weight ranging from about 900 to about 3000 (g/mol).

7 . The method of claim 5 , wherein
the monomers of the oxidized fatty substance composition have an average molecular weight ranging from about 600 to about 2000 (g/mol), the dimers of the oxidized fatty substance composition have an average molecular weight ranging from about 1200 to about 4000 (g/mol), and the compounds having three or more mers of the oxidized fatty substance composition have an average molecular weight ranging from about 1800 to about 6000 (g/mol).

8 . The method of claim 5 , wherein
the monomers of the oxidized fatty substance composition have an average molecular weight ranging from about 900 to about 3000 (g/mol), the dimers of the oxidized fatty substance composition have an average molecular weight ranging from about 1800 to about 6000 (g/mol), and the compounds having three or more mers of the oxidized fatty substance composition have an average molecular weight ranging from about 2100 to about 9000 (g/mol).

9 . The method of claim 1 , wherein the oxidized fatty substance composition has a viscosity of at least 40 cSt at 100° C.

10 . (canceled)

11 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of fatty acids or their salts, and combinations thereof.

12 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of the fatty acid esters C 1 -C 6 alkyl mono-alcohols and combinations thereof.

13 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of the mono-, di-, or tri- fatty acid esters of glycerol and combinations thereof.

14 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of fatty acid components having an average molecular weight ranging from about 200 to about 1000 (g/mol).

15 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of fatty acid components having an average molecular weight ranging from about 600 to about 2000 (g/mol).

16 . The method of claim 1 , wherein at least about 60% by weight of the compounds having a fatty acid component in the fatty substance composition from step (a) are compounds selected from the group consisting of fatty acid components having an average molecular weight ranging from about 900 to about 3000 (g/mol) (g/mol).

17 . The method of any of claims 1 - 8 , wherein the fatty substance composition from step (a) are components recovered from a member of the group selected from the group consisting of soybean oil, linseed oil, canola oil, rapeseed oil, cottonseed oil, sunflower oil, palm oil, peanut oil, safflower oil, corn oil, corn stillage oil, tall oil, and combinations thereof.

18 . The imidazoline functionalized oxidized fatty substance emulsifier made by the process of claim 1 .

19 . (canceled)

20 . An asphalt emulsion composition comprising the imidazoline functionalized oxidized fatty substance emulsifier of claim 18 .

21 . The asphalt emulsion composition of claim 20 , wherein the asphalt emulsion composition is selected from a slurry seal composition or a microsurfacing composition.

22 . (canceled)

23 . A corrosion inhibitor composition comprising the imidazoline functionalized oxidized fatty substance emulsifier of claim 18 .

Assignees

• Cargill Inc

Inventors

• Kurth Todd L
• Stauduhar Suzanne

Classifications

• C08L95/005 Primary

  Aqueous compositions, e.g. emulsions · CPC title

• C23F11/145

  Amides; N-substituted amides · CPC title

• C08K5/109

  of carbonic acid {, e.g. R-O-C(=O)-O-R} · CPC title

• C08F210/02 Primary

  Ethene · CPC title

• C08K5/16

  Nitrogen-containing compounds {(C08K5/0091 takes precedence)} · CPC title