IP Library Granted Patent US 8,563,499
Granted Patent B2
US 8,563,499 · App. 13/072,703 · Granted Oct 22, 2013

Fabric softener active composition

Inventors: Hans-Jürgen Köhle (Mainhausen, DE); Matthias Schöppner (Bad Soden Salmünster, DE); Axel Euler (Steinau an der Strasse, DE); Harald Jakob (Hasselroth, DE); Saji John Meledathu (Chester, VA); Todd L. Kurth (Chester, VA); Delbert G. Young (Groveland, IL); Ingo Hamann (Chesterfield, VA); Georg Schick (Krefeld, DE)
Assignee: Evonik Degussa GmbH
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Quick Facts
Patent No.
US 8,563,499
App. No.
13/072,703
Granted
Oct 22, 2013
Kind
B2
Abstract

A fabric softener active composition, comprising from 65 to 95% by weight of a bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.80 to 1.96, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of from 0 to 50, from 2 to 8% by weight of a fatty acid triglyceride having an average chain length of the fatty acid moieties of from 10 to 14 carbon atoms and an iodine value of from 0 to 15, and from 3 to 12% by weight of an alcohol selected from ethanol, 1-propanol and 2-propanol has low melt viscosity, high stability towards dealkylation in the molten state and low flammability.

Claims (26)

1. A fabric softener active composition, comprising:

a) from 65 to 95% by weight of a bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester, having a molar ratio of fatty acid moieties to amine moieties of from 1.80 to 1.96, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 50;

b) from 2 to 8% by weight of a fatty acid triglyceride having an average chain length of the fatty acid moieties of from 10 to 14 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 15; and

c) from 3 to 12% by weight of an alcohol selected from ethanol, 1-propanol and 2-propanol.

2. The fabric softener active composition of claim 1 , comprising from 3 to 6% by weight of said fatty acid triglyceride.

3. The fabric softener active composition of claim 2 , comprising from 6 to 10% by weight of said alcohol.

4. The fabric softener active composition of claim 3 , wherein the fatty acid triglyceride is a coconut oil or a hydrogenated coconut oil.

5. The fabric softener active composition of claim 4 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

6. The fabric softener active composition of claim 3 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

7. The fabric softener active composition of claim 3 , wherein the combined amount of said fatty acid triglyceride and said alcohol is from 10 to 15% by weight.

8. The fabric softener active composition of claim 7 , wherein the fatty acid triglyceride is a coconut oil or a hydrogenated coconut oil.

9. The fabric softener active composition of claim 8 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

10. The fabric softener active composition of claim 1 , wherein the combined amount of said fatty acid triglyceride and said alcohol is from 10 to 15% by weight.

11. The fabric softener active composition of claim 10 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

12. The fabric softener active composition of claim 1 , wherein the fatty acid triglyceride is a coconut oil or a hydrogenated coconut oil.

13. The fabric softener active composition of claim 12 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

14. The fabric softener active composition of claim 1 , wherein the fatty acid moieties of the bis-(2-hydroxyethyl)-dimethylammonium chloride fatty acid ester have an iodine value, calculated for the free fatty acid, of from 15 to 35.

15. A method for making a fabric softener active composition according to claim 1 , comprising the steps:

a) reacting a mixture comprising from 78 to 95% by weight bis-(2-hydroxyethyl)-methylamine fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.80 to 1.96, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 50, from 2 to 9% by weight of a fatty acid triglyceride having an average chain length of the fatty acid moieties of from 10 to 14 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 15, and from 3 to 13% by weight of an alcohol selected from ethanol, 1-propanol and 2-propanol with an excess of methyl chloride at a temperature of from 60 to 120° C. to provide a reaction mixture, and

b) separating unreacted methyl chloride from the reaction mixture of step a) by distilling off a mixture of methyl chloride and said alcohol, condensing alcohol from said mixture of methyl chloride and alcohol and returning condensed alcohol to said reaction mixture to provide a content of alcohol of from 3 to 12% by weight.

16. The method of claim 15 , wherein the mixture of methyl chloride and alcohol is distilled off at a total pressure of from 0.2 to 1 bar.

17. A method for making a fabric softener active composition according to claim 1 , comprising the steps

a) reacting a mixture comprising from 88 to 98% by weight bis-(2-hydroxyethyl) -methylamine fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.80 to 1.96, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 50, from 2 to 9% by weight of a fatty acid triglyceride having an average chain length of the fatty acid moieties of from 10 to 14 carbon atoms and an iodine value, calculated for the free fatty acid, of from 0 to 15, and from 0 to 3% by weight of an alcohol selected from ethanol, 1-propanol and 2-propanol with an excess of methyl chloride at a temperature of from 60 to 120° C. to provide a reaction mixture,

b) adding more of the alcohol to the reaction mixture of step a) to provide a content of alcohol of from 3 to 12% by weight, and

c) separating unreacted methyl chloride from the mixture of step b) by distilling off a mixture of methyl chloride and said alcohol, condensing alcohol from said mixture of methyl chloride and alcohol and returning condensed alcohol to said reaction mixture to provide a content of alcohol of from 3 to 12% by weight.

18. The method of claim 17 , wherein the mixture of methyl chloride and alcohol is distilled off at a total pressure of from 0.2 to 1 bar.

Assignments (6)
CHANGE OF NAME Recorded Jan 26, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051697/0756 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2011
From: EVONIK GOLDSCHMIDT CORPORATION
To: EVONIK DEGUSSA GMBH
Reel/Frame 026390/0155 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 19, 2011
From: MELEDATHU, SAJI JOHN; KURTH, TODD L.; YOUNG, DELBERT G.; SCHICK, GEORG
To: EVONIK GOLDSCHMIDT CORPORATION
Reel/Frame 026307/0758 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 19, 2011
From: EVONIK DEGUSSA CORPORATION
To: EVONIK DEGUSSA GMBH
Reel/Frame 026310/0754 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2011
From: KOHLE, HANS-JURGEN; SCHOPPNER, MATTHIAS; EULER, AXEL; JAKOB, HARALD
To: EVONIK DEGUSSA GMBH
Reel/Frame 026290/0533 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2011
From: HAMANN, INGO
To: EVONIK DEGUSSA CORPORATION
Reel/Frame 026263/0480 →
Continuity (2)
Provisional Application 61319997 · Apr 1, 2010
Related Publication 20110245139A1 · Oct 6, 2011