Difunctional, amine-based surfactants, and their precursors, preparation, compositions and use
A technology of surfactant and composition, applied in the field of preparing these surfactants
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Embodiment 1A
[0066] Example 1A: Preparation C 12 -Diquaternary ammonium compound-TM (N,N,N,N',N',N'-hexamethyl-2-(dodecyloxy)-1,3-propanediammonium dichloride)
[0067] Step 1: Preparation of C from 1,3-dichloropropan-2-yloxydodecane 12 -Diamine 2 (N,N,N',N'-tetramethyl-2-(dodecyloxy)-1,3-propanediamine)
[0068] In N with propeller impeller and removable glass sleeve 2 In the purged 450ml Parr reactor, 17.7 grams (g) N 2 1,3-Dichloropropan-2-yloxydodecane (59.5 mmol) sparged. The reactor was then charged with a non-degassed solution of 115.8 g of dimethylamine (40% in water, Aldrich; 1.028 mmol; 17.3 equivalents) via cannula. The reactor was sealed and stirring and heating started. The temperature reached a maximum of 119°C within 100 minutes and then stabilized at 106-108°C for 16 hours. The reactor was then cooled to 80°C and the pressure was slowly released into copious 1N HCl through a gas disperser. Opening the reactor at room temperature revealed a cloudy white lower layer an...
Embodiment 1B
[0071] Example 1B: Preparation C 16 -Diquaternary ammonium compound-TM (N,N,N,N',N',N'-hexamethyl-2-(hexadecyloxy)-1,3-propanediammonium dichloride)
[0072] Step 1: Preparation of N,N,N',N'-tetramethyl-2-(hexadecyloxy)-1,3-propane from 1,3-dichloropropan-2-yloxyhexadecane Diamine (C 16 - diamine 2)
[0073] In N with propeller impeller and removable glass sleeve 2 A purged 450 ml Parr reactor was charged with 26.80 g of 1,3-dichloropropan-2-yloxyhexadecane (75.8 mmol) via syringe and 130.35 g of dimethylamine solution (40 g in water at 40 mM) via cannula. %, Aldrich; 1.157 mmol; 15.3 equivalents). Put the reactor at 10psi N 2 Lower seal and heat to 105-116°C (90-110 psi) for 19 hours. After cooling to 30 °C, the reactor was evacuated and then filled with flowing N 2 Purge for about 75 minutes. Pour the reactor contents into a separatory funnel with 200ml water and 100ml hexane. Wash the aqueous part twice with 100 ml hexane and wash the combined organic part with anh...
Embodiment 1C
[0076] Example 1C: Preparation of C Dibetaine (2,2'-(dodecyl-2-yloxypropane-1,3-diyl)bis)(dimethylammonionediyl)bis acetate)
[0077] 24.6g (0.211 mol) sodium chloroacetate, 4.58g (0.043 mol) sodium carbonate, 26.77g (0.0852 mol) N, N, N', N'-tetramethyl-2-deca were charged in a 250ml round bottom flask Dialkoxypropyl-1,3-diamine, 90 ml methanol and 10 ml water. After heating to reflux for two days, the mixture was cooled in an ice bath, filtered and the filter cake was rinsed with methanol. The filtrate was concentrated to give 47.8 g of 2,2'-(dodec-2-yloxypropane-1,3-diyl)bis) containing 5% by weight of sodium chloride (ion selective electrode). (Dimethylaminodiyl) diacetate salt as a clear oil. 1 H NMR (D 2 O), ppm: (δ) 4.6-4.9 (br m), 3.9 (br, m), 3.3 (br s), 2.4 (br s), 2.25 (s), 1.2-1.8 (br s), 0.9 ( s). 13 C NMR (D 2 (0), ppm: (δ) 170.4, 170.3, 170.2, 170.1, 75.0, 73.4, 67.2, 67.4, 67.8, 68.3, 54.6, 54.9, 55.0, 55.5, 55.8, 16 to 51, multiplet. Mass spectrum: C ...
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