Urea-containing silanes, their preparation and their use
A urea silane, silane technology, applied in chemical instruments and methods, organic chemistry, compounds of Group 4/14 elements of the periodic table, etc., can solve problems such as poor reinforcement characteristics and high rolling resistance
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Embodiment 1
[0208] Embodiment 1: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 2 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 and elemental sulfur preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 4 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 (similar to the first method according to the invention)
[0209] At the beginning will (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 2 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 (5.00 g, 7.7 mmol, 1.00 equiv) and elemental sulfur (0.50 g, 15.5 moles, 2.00 equiv) were added to dry N 2 A purged three-necked flask with a stirrer, reflux condenser, and internal thermometer, the mixture was heated to 140°C and stirred for 2 hours. After cooling a viscous red oil (EtO) was obtained 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 4 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 The product (4.16 g, 75.8% of theory), which subsequently solidified, gave an orange solid.
[0210] 1 H...
Embodiment 2
[0216] Embodiment 2: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NH 2 、OCN-CH 2 CH 2 -Cl and Na 2 S 4 Preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 4 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 (similar to the second method according to the invention)
[0217] In the first reaction step, 3-aminopropyltriethoxysilane (73.05 g, 0.33 mol, 1.00 equiv) was initially charged to pentane (2.5 l) in a 4 l three-necked flask which With precision glass stirrer, internal thermometer, addition funnel and reflux condenser, and cooled to -78°C. 2-Chloroethyl isocyanate (34.82 g, 0.33 mol, 1.00 equiv) was added dropwise at -78°C to -70°C over 4.5 hours, and then the mixture was allowed to warm to room temperature. The white suspension was filtered, washed with pentane, and washed with N 2 Let dry overnight. (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 The -Cl intermediate (113.41 g, quantitative) was a white flaky powder.
[0218] In the second reaction ste...
Embodiment 3
[0223] Embodiment 3: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NH 2 、OCN-CH 2 CH 2 -Cl and Na 2 S 4 Preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S 4 -CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 CH 2 -Si(OEt) 3 (similar to the second method according to the invention)
[0224] In the first reaction step, 3-aminopropyltriethoxysilane (154.95 g, 0.70 mol, 1.00 equiv) was initially charged to ethanol (3.0 l) in a 4 l three-necked flask with a precision Glass stirrer, internal thermometer, addition funnel and reflux condenser, and cooled to -78°C. 2-Chloroethyl isocyanate (73.86 g, 0.70 mol, 1.00 equiv) was added dropwise over 1 hour at -78°C to -60°C during which time a bulky salt precipitated. The mixture was then heated to 50°C and sodium polysulfide (Na 2 S 4 , 57.62 g, 0.35 mol, 1.00 equiv), and the mixture was heated to reflux. After a reaction time of 4.5 hours, the mixture was cooled to room temperature and the suspension was filtered. The filtrate was freed o...
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