IP Library Granted Patent US 8,883,712
Granted Patent B2
US 8,883,712 · App. 13/643,486 · Granted Nov 11, 2014

Fabric softening composition

Inventors: Hans-Jürgen Köhle (Mainhausen, DE); Ulrike Kottke (Linsengericht-Grossenhausen, DE); Hans Henning Wenk (Mülheim a. d. Ruhr, DE); Harald Jakob (Hasselroth, DE)
Assignee: Evonik Degussa GmbH
C11D1/835C11D1/667C11D3/2079C11D1/62C11D3/2013C07C219/06C11D3/0015C07C213/06
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Quick Facts
Patent No.
US 8,883,712
App. No.
13/643,486
Granted
Nov 11, 2014
Kind
B2
Abstract

A fabric softening composition which comprises as component A a tertiary or quaternary ammonium salt of formulae (I) or (II): R 1 R 2 R 3 N + CH 2 CHR 4 OC(═O)R 5 X −   (I) R 1 R 2 R 3 N + (CH 2 ) 3 NHR(═O)R 5 X −   (II) in which R 1 is hydrogen, methyl or ethyl, R 2 and R 3 , independently of one another, are C 1-4 alkyl or C 2-4 hydroxyalkyl, R 4 is hydrogen or methyl, R 5 is a linear C 15-21 alkyl or alkenyl radical and X − is a monovalent anion, and as component B a nonionic softener with only one long-chain hydrocarbon radical bonded to a polar radical having at least one free hydroxy group, where fatty alcohol alkoxylate or fatty acid alkoxylate are excluded as component B, exhibits a good softening effect and forms storage-stable dispersions if the molar ratio of component A to component B is in the range from 2:1 to 1:3, the difference between the average chain length of the long-chain hydrocarbon radicals of components A and B is at most 2 carbon atoms and the hydrocarbon radicals of components A and B have on average in each case at most 0.5 double bonds per hydrocarbon radical. Such a composition can be produced by reacting a fatty acid, a C 2-6 diol or C 3-9 polyol, and a tertiary alkanolamine or a diamine having a tertiary and primary amino group in a suitable molar ratio with the removal of water and subsequent alkylation or protonation.

Claims (56)

1. A fabric softening composition, comprising:

a) as component A, at least one tertiary or quaternary ammonium salt, selected from compounds of formulae (I) and (II):

R 1 R 2 R 3 N + CH 2 CHR 4 OC(═O)R 5 X −   (I)

R 1 R 2 R 3 N + (CH 2 ) 3 NHC(═O)R 5 X −   (II)

wherein:

R 1 is hydrogen, methyl or ethyl,

R 2 and R 3 , independently of one another, are a C 1-4 alkyl or C 2-4 hydroxyalkyl,

R 4 is hydrogen or methyl,

R 5 is a linear C 15-21 alkyl or alkenyl radical and

X − is a monovalent anion,

and

b) as component B, at least one nonionic softener selected from the group consisting of fatty acids, monoesters of fatty acids with a C 2-6 diol or C 3-9 polyol, and monoesters of fatty alcohols with a C 2-6 hydroxycarboxylic acid,

and wherein:

i) the molar ratio of the total amount of component A to the total amount of component B is in the range from 2:1 to 1:3,

ii) the difference between the average chain length of the long-chain hydrocarbon radicals of components A and B is at most 2 carbon atoms,

iii) the hydrocarbon radicals of components A and B have on average in each case at most 0.5 double bonds per hydrocarbon radical and

iv) the total amount of tertiary and quaternary ammonium salts carrying two long-chain hydrocarbon radicals of 15 to 21 carbon atoms in the composition is at most 80 mol % of the total amount of components A;

v) wherein the total fraction of component A and component B in the composition is at least 50% by weight.

2. The fabric softening composition of claim 1 , wherein the total amount of tertiary and quaternary ammonium salts carrying two long-chain hydrocarbon radicals of 15 to 21 carbon atoms in the composition is at most 50 mol % of the total amount of components A.

3. The fabric softening composition of claim 1 , wherein the total fraction of component A and component B in the composition is at least 80% by weight.

4. The fabric softening composition of claim 1 , comprising at most 10% by weight of water.

5. The fabric softening composition of claim 1 , wherein component B is selected from the group consisting of fatty acids and fatty acid monoesters of glycerol, diglycerol, triglycerol, sorbitol and sorbitan.

6. The fabric softening composition of claim 1 , wherein, in formulas (I) and (II), R 2 is a C 1-4 alkyl radical.

7. The fabric softening composition of claim 6 , wherein, in formulas (I) and (II), R 2 is a methyl radical.

8. The fabric softening composition of claim 1 , wherein in formulas (I) and (II), R 2 and R 3 , independently of one another, are C 1-4 alkyl radicals.

9. The fabric softening composition of claim 8 , wherein in formulas (I) and (II), R 2 and R 3 are methyl radicals.

10. The fabric softening composition of claim 1 , wherein R 1 is methyl, in formula (I) R 2 and R 3 , independently of one another, are methyl, 2-hydroxyethyl or 2-hydroxypropyl, in formula (II) R 2 and R 3 are methyl, and X − is chloride or methylsulphate.

11. The fabric softening composition of claim 1 , wherein component A and component B comprise the same long-chain hydrocarbon radical.

12. An aqueous rinse cycle fabric softener comprising 70 to 98% by weight of water and 2 to 25% by weight of the fabric softening composition of claim 1 .

13. A method of producing an aqueous rinse cycle fabric softener, comprising adding the composition of claim 1 in liquid form to water or an aqueous solution.

14. A process for producing the fabric softening composition of claim 1 , comprising:

a) reacting a mixture comprising

n mol of a C 16-22 fatty acid with an iodine number of at most 45,

m mol of a C 2-6 diol or C 3-9 polyol and

p mol of an alkanolamine of the formula R 2 R 3 NCH 2 CHR 4 OH, in which R 2 and R 3 , independently of one another, are methyl, 2-hydroxyethyl or 2-hydroxypropyl and R 4 is hydrogen or methyl,

where the ratio of p:m is in the range from 2:1 to 1:3 and

n:(p+m) is in the range from 0.75 to 1.4,

at a temperature in the range from 140 to 210° C. with removal of water and

b) reacting the mixture obtained in step a) with either

i) an alkylating agent at a temperature in the range from 50 to 100° C. until at least 90% of the tertiary amino groups have been quaternized; or

ii) an acid until at least 98% of the tertiary amino groups have been protonated.

15. The process of claim 14 , wherein in step b), the mixture obtained in step a) is reacted with an alkylating agent at a temperature in the range from 50 to 100° C. until at least 90% of the tertiary amino groups have been quaternized and said alkylating agent is either dimethyl sulphate or methyl chloride.

16. The process of claim 14 , wherein in step b), the mixture obtained in step a) is reacted with an acid until at least 98% of the tertiary amino groups have been protonated and said acid is a carboxylic acid having 1 to 3 carbon atoms.

17. A process for producing the fabric softening composition of claim 1 , comprising:

a) reacting a mixture comprising:

n mol of a C 16-22 fatty acid with an iodine number of at most 45,

m mol of a C 2-6 diol or C 3-9 polyol and

p mol of N,N-dimethyl-1,3-propanediamine,

where the ratio of p:m is in the range from 2:1 to 1:3 and

n is in the range from 0.75*m+p to 1.4*m+p,

at a temperature in the range from 140 to 210° C. with removal of water and

b) reacting the mixture obtained in step a) with either:

i) an alkylating agent at a temperature in the range from 50 to 100° C. until at least 90% of the tertiary amino groups have been quaternized; or

ii) an acid until at least 98% of the tertiary amino groups have been protonated.

18. The process of claim 17 , wherein in step b), the mixture obtained in step a) is reacted with an alkylating agent at a temperature in the range from 50 to 100° C. until at least 90% of the tertiary amino groups have been quaternized and said alkylating agent is either dimethyl sulphate or methyl chloride.

19. The process of claim 17 , wherein in step b), the mixture obtained in step a) is reacted with an acid until at least 98% of the tertiary amino groups have been protonated and said acid is a carboxylic acid having 1 to 3 carbon atoms.

Assignments (2)
CHANGE OF NAME Recorded Feb 27, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052039/0274 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2012
From: KOHLE, HANS-JURGEN; KOTTKE, ULRIKE; WENK, HANS HENNING; JAKOB, HARALD
To: EVONIK DEGUSSA GMBH
Reel/Frame 029252/0128 →
Priority Claims (1)
EP 10161296 · Apr 28, 2010 · regional
Continuity (1)
Related Publication 20130053299A1 · Feb 28, 2013