Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester
View Patent ↗In a method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester by quaternizing a tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate the quaternizing is carried out in the presence of a solid acid scavenger. The method can provide a fabric softener active composition, comprising from 65 to 98% by weight of at least one tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester, the corresponding non-quaternized tris-(2-hydroxyethyl)-amine fatty acid esters in amounts providing a total amine number of the composition of from 2 to less than 7 mg KOH/g, and from 1 to 1500 ppm methanol.
1. A fabric softener active composition, comprising
a) from 65 to 98% by weight of at least one tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester,
b) the corresponding non-quaternized tris-(2-hydroxyethyl)-amine fatty acid esters in amounts providing a total amine number of the composition of from 2 to less than 7 mg KOH/g, and
c) from 1 to 1500 ppm methanol.
2. The fabric softener active composition of claim 1 , comprising from 10 to 800 ppm methanol.
3. The fabric softener active composition of claim 1 , further comprising up to 35% by weight of a solvent selected from the group consisting of ethanol, 1-propanol, 2-propanol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, C 1 -C 4 -alkyl monoethers of ethylene glycol, C 1 -C 4 -alkyl monoethers of propylene glycol and mixtures thereof.
4. The fabric softener active composition of claim 1 , wherein said tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester has an average molar ratio of fatty acid moieties to nitrogen of from 1.4 to 2.0.
5. The fabric softener active composition of claim 1 , wherein the fatty acid moieties of said tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester have an iodine value of from 0.5 to 120.
6. The fabric softener active composition of claim 1 , wherein the fatty acid moieties of said tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester have an average chain length of from 16 to 18 carbon atoms.
7. The fabric softener active composition of claim 1 , wherein said tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester comprises less than 10 mol-% polyunsaturated fatty acid moieties.
8. The fabric softener active composition of claim 1 , wherein the tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester is made by a method comprising a step of quaternizing a tris-(2-hydroxyethyl)-amine fatty acid ester with dimethylsulfate, wherein the quaternizing is carried out in the presence of a solid acid scavenger.
9. The fabric softener active composition of claim 8 , wherein the solid acid scavenger in said method is selected from the group consisting of alkali metal carbonates, alkali metal hydrogen carbonates, alkaline earth metal carbonates, alkaline earth metal oxides and alkaline earth metal hydroxides.
10. The fabric softener active composition of claim 9 , wherein the solid acid scavenger in said method is sodium carbonate or sodium hydrogen carbonate.
11. The fabric softener active composition of claim 8 , wherein the solid acid scavenger in said method consists of particles having a median particle size of at least 100 μm.
12. The fabric softener active composition of claim 8 , wherein, after quaternizing in said method, the solid acid scavenger is separated by filtration or centrifugation.
13. The fabric softener active composition of claim 12 , wherein, in said method, a solvent selected from the group consisting of ethanol, 1-propanol, 2-propanol ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, C 1 -C 4 -alkyl monoethers of ethylene glycol, C 1 -C 4 -alkyl monoethers of propylene glycol and mixtures thereof, is added after quatermizing and before separating the solid acid scavenger.
14. The fabric softener active composition of claim 13 , wherein the separated solid acid scavenger is washed with said solvent to give a washing liquid and the washing liquid is reused for adding solvent after quaternizing.
15. The fabric softener active composition of claim 8 , wherein the molar ratio of dimethylsulfate to tris-(2-hydroxyethyl)-amine fatty acid ester in said method is from 0.9 to 0.98.
16. The fabric softener active composition of claim 8 , wherein quaternizing in said method is carried out at a temperature of from 60 to 95° C.
17. The fabric softener active composition of claim 8 , wherein the tris-(2-hydroxyethyl)-amine fatty acid ester in said method has an average molar ratio of fatty acid moieties to nitrogen of from 1.4 to 2.0.
18. The fabric softener active composition of claim 8 , wherein the fatty acid moieties of said tris-(2-hydroxyethyl)-amine fatty acid ester in said method have an iodine value of from 0.5 to 120.
19. The fabric softener active composition of claim 8 , wherein the fatty acid moieties of said tris-(2-hydroxyethyl)-amine fatty acid ester have an average chain length of from 16 to 18 carbon atoms.
20. The fabric softener active composition of claim 8 , wherein the tris-(2-hydroxyethyl)-amine fatty acid ester comprises less than 10 mol-% polyunsaturated fatty acid moieties.