FABRIC SOFTENER ACTIVE COMPOSITION

Abstract

A fabric softener active composition, comprising as component A at least 50% by weight of a bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.5 to 1.99, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of the fatty acid moieties, calculated for the free fatty acid, of from 0.5 to 50, and as component B a (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulphate fatty acid ester having the same fatty acid moieties as component A, and wherein the molar ratio of component B to component A is from 0.05 to 0.20.

Claims

1-13. (canceled)

14. A fabric softener active composition, comprising: a) as component A, at least 50% by weight of a bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester having a molar ratio of fatty acid moieties to amine moieties of from 1.5 to 1.99, an average chain length of the fatty acid moieties of from 16 to 18 carbon atoms and an iodine value of the fatty acid moieties, calculated for the free fatty acid, of from 0.5 to 50; and b) as component B, a (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulphate fatty acid ester having the same fatty acid moieties as component A; wherein the molar ratio of component B to component A is from 0.05 to 0.20.

15. The fabric softener active composition of claim 14, wherein the molar ratio of fatty acid moieties to amine moieties is from 1.85 to 1.99.

16. The fabric softener active composition of claim 14, wherein the iodine value of the fatty acid moieties, calculated for the free fatty acid, is from 5 to 40.

17. The fabric softener active composition of claim 14, wherein the iodine value of the fatty acid moieties, calculated for the free fatty acid, is from 15 to 35.

18. The fabric softener active composition of claim 14, wherein the combined amount of components A and B is from 85 to 99% by weight.

19. The fabric softener active composition of claim 14, wherein component A comprises less than 6% by weight of multiply unsaturated fatty acid moieties.

20. The fabric softener active composition of claim 14, wherein the cis-trans-ratio of double bonds of unsaturated fatty acid moieties of component A is higher than 55:45.

21. The fabric softener active composition of claim 14, comprising less than 2% by weight of water.

22. The fabric softener active composition of claim 14, comprising less than 0.5% by weight of water.

23. The fabric softener active composition of claim 14, comprising less than 10% by weight of solvents having a flash point of less than 20° C.

24. The fabric softener active composition of claim 14, comprising less than 1% by weight of solvents having a flash point of less than 20° C.

25. The fabric softener active composition of claim 14, further comprising up to 9.9% by weight of at least one solvent selected from glycerol, ethylene glycol, propylene glycol, dipropylene glycol and C1-C4 alkyl monoethers of ethylene glycol, propylene glycol and dipropylene glycol.

26. The fabric softener active composition of claim 14, further comprising 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.

27. The fabric softener active composition of claim 14, further comprising from 1.5 to 10% by weight of a bis-(2-hydroxypropyl)-methylamine fatty acid ester containing the same fatty acid moieties as component A.

28. The fabric softener active composition of claim 18, wherein the cis-trans-ratio of double bonds of unsaturated fatty acid moieties of component A is higher than 55:45.

29. The fabric softener active composition of claim 28, comprising less than 2% by weight of water.

30. The fabric softener active composition of claim 29, further comprising 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.

31. A method for making the fabric softening composition of claim 14, comprising the steps: a) reacting a mixture, containing (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-methylamine and bis-(2-hydroxypropyl)-methylamine at a molar ratio of from 0.05 to 0.20, with a fatty acid having an average chain length of from 16 to 18 carbon atoms and an iodine value of from 0.5 to 50, in a molar ratio of fatty acid to amine of from 1.51 to 2.0, with removal of water at a temperature of from 160 to 220° C. until the acid value of the reaction mixture is in the range from 1 to 10 mg KOH/g; and b) reacting the product of step a) with dimethyl sulphate at a molar ratio of dimethyl sulphate to amine of from 0.90 to 0.97 until the total amine value of the reaction mixture is in the range from 1 to 8 mg KOH/g.

32. The method of claim 31, wherein, in step b), said the molar ratio of dimethyl sulphate to amine is from of from 0.92 to 0.95

33. The method of claim 31, wherein the molar ratio of fatty acid to amine is from 1.86 to 2.0.

Description

EXAMPLES

Example 1

[0040] 1372 g (4.98 mol) of a partially hydrogenated vegetable fatty acid having an iodine value of 19.5 and an average chain length of the fatty acid moieties of 17.3 was placed with 0.2% by weight of 50% by weight hypophosphorous acid in an electrically heated reactor equipped with a thermometer, a mechanical stirrer and a rectifying column. 380 g (2.58 mol) of an amine mixture, containing 93% by weight bis-(2-hydroxypropyl)-methylamine and 7% by weight (2-hydroxypropyl)-(1-methyl-2 hydroxyethyl)-methylamine, was added with stirring. The resulting mixture was heated with stirring to 190° C. and was kept at this temperature for 4 h at ambient pressure, distilling off water through the rectifying column. The pressure was then reduced to 10 mbar and the mixture was further stirred at 190° C., water being removed with a vacuum pump until an acid value of the reaction mixture of 6.7 mg KOH/g was reached. The resulting mixture was then cooled to 70° C., 299.7 g (2.37 mol) of dimethyl sulphate was added and the resulting mixture was stirred for 2 h at 70 to 90° C.

[0041] The resulting fabric softener active composition was a viscous liquid at 90° C., having a total amine value of 4.8 mg KOH/g. HPLC analysis (Waters Spherisorb® SCX column, methanol eluent with a formic acid triethylamine buffer, RI detection) showed the bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester to be composed of 8.2% monoester and 91.8% diester (rel. area percentages). .sup.13C NMR spectra of the composition showed bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid monoester, bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid diester and (2-hydroxypropyl)-(1-methyl-2 hydroxyethyl)-dimethylammonium methylsulphate fatty acid diester in molar ratios of 0.14 : 0.75 : 0.11.

Example 2 (Comparative Example)

[0042] 237 g (2.34 mol) triethylamine were added to a solution of 176.6 g (1.2 mol) bis-(2-hydroxypropyl)-methylamine in 2500 g dichloromethane. 690 g (2.34 mol) of fatty acid chloride, prepared from the fatty acid used in example 1, were added drop wise with stirring and cooling to keep the temperature in a range of 40 to 45° C. The mixture was stirred for a further 12 h at this temperature, cooled to ambient temperature and 4000 g dichloromethane were added. The resulting solution was washed several times with saturated aqueous NaCl solution, aqueous Ca(OH).sub.2 solution and 50% by weight aqueous K.sub.2CO.sub.3 solution and dried with Na.sub.2SO.sub.4. Dichloromethane was distilled off to provide 628 g of an esteramine mixture having an acid value of 2.3 mg KOH/g.

[0043] 108.5 g (0.86 mol) of dimethyl sulphate were added to the esteramine mixture at 65 to 90° C. and the resulting mixture was for 2 h at this temperature.

[0044] The resulting fabric softener active composition was a viscous liquid at 90° C., having a total amine value of 5.5 mg KOH/g. HPLC analysis showed the bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid ester to be comprised of 6.2% monoester and 93.8% diester (rel. area percentages). .sup.13C NMR spectra of the composition showed bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid monoester and bis-(2-hydroxypropyl)-dimethylammonium methylsulphate fatty acid diester in molar ratios of 0.084 : 0.916, but no (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulphate fatty acid ester.

Example 3 (Comparative Example)

[0045] Example 2 was repeated using a mixture of 95.5% by weight bis-(2-hydroxypropyl)-methylamine and 4.5% by weight (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-methylamine instead of pure bis-(2-hydroxypropyl)-methylamine. 641 g of an esteramine mixture having an acid value of 2.6 mg KOH/g were obtained and reacted with 107.1 g (0.85 mol) of dimethyl sulphate as in example 2.

[0046] The resulting fabric softener active composition was a viscous liquid at 90° C., having a total amine value of 5.9 mg KOH. .sup.13C NMR spectra of the composition showed bis-(2-hydroxypropyl)-dimethylammonium methylsulfate fatty acid monoester, bis-(2-hydroxypropyl)-dimethylammonium methylsulfate fatty acid diester and (2-hydroxypropyl)-(1-methyl-2-hydroxyethyl)-dimethylammonium methylsulfate fatty acid diester in molar ratios of 0.10 : 0.86 : 0.04.

[0047] Example 4

[0048] A rinse cycle fabric softener containing 7.7% by weight fabric softener active composition of example 1, 0.044% by weight formic acid, 0.01% by weight HCl, 0.02% by weight CaCl.sub.2, 0.007% by weight hydroxyethylidene-1,1-diphosphonic acid monosodium salt (NaHEDP), 0.1% by weight polydimethylsiloxane Dow Corning® MP-10 antifoam emulsion, 2.4% by weight perfume, less than 0.1% by weight dye and the remainder water was prepared as follows.

[0049] The fabric softener active composition, preheated to 85° C., was added with stirring with a Rushton turbine to a mixture of water, formic acid, HCl, CaCl.sub.2 and NaHEDP kept at 63-64° C. The resulting dispersion was cooled to room temperature and the further components were added with stirring with a high shear mixer at 8000 min.sup.−1 for 15 s.

[0050] The resulting rinse cycle fabric softener had a viscosity of 742 mPa*s determined after 24 h with a Brookfield® DV-E viscosimeter at 20° C. and a rotation speed of 60 min.sup.−1.

Example 5 (Comparative Example)

[0051] Example 4 was repeated using the fabric softener active composition of example 2.

[0052] The resulting rinse cycle fabric softener had a viscosity of 49 mPa*s.

Example 6 (Comparative Example)

[0053] Example 4 was repeated using the fabric softener active composition of example 3.

[0054] The resulting rinse cycle fabric softener had a viscosity of 281 mPa*s.

Example 7

[0055] Example 4 was repeated using 5.2% by weight fabric softener active composition of example 1, 0.045% by weight formic acid, 0.01% by weight HCl, 0.02% by weight CaCl.sub.2, 0.007% by weight hydroxyethylidene-1,1-diphosphonic acid monosodium salt (NaHEDP), 0.1% by weight polydimethylsiloxane Dow Corning® MP-10 antifoam emulsion, 2.2% by weight perfume, 0.03% by weight cationic acrylic polymer thickener Rheovis® CDE supplied by BASF, less than 0.1% by weight dye and the remainder water.

[0056] The resulting rinse cycle fabric softener had a viscosity of 44 mPa*s. No phase separation was observed after storage for 3 weeks at 20° C.

Example 8 (Comparative Example)

[0057] Example 7 was repeated using the fabric softener active composition of example 2.

[0058] The resulting rinse cycle fabric softener had a viscosity of 13 mPa*s. Phase separation occurred during storage for 3 weeks at 20° C.

Example 9 (Comparative Example)

[0059] Example 7 was repeated using the fabric softener active composition of example 3. The resulting rinse cycle fabric softener had a viscosity of 29 mPa*s. No phase separation was observed after storage for 3 weeks at 20° C.

[0060] Examples 3 to 9 demonstrate that a rinse cycle fabric softener made from the fabric softener active composition of the present invention has higher viscosity and better storage stability compared with a rinse cycle fabric softener made from a fabric softener active composition containing only component A and no component B or containing components A and B with a molar ratio of component B to component A of less than 0.05.