triethoxy(3-isocyanatopropyl)silane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-Propanediol (2.9 g, 38.0 mmol) is reacted with 3-isocyanatopropyltriethoxy silane (16.4 g, 76.0 mmol) and 0.2% dibutyltin dilaurate catalyst. The reaction is conducted under nitrogen at room temperature in a glass vessel with mechanical stirring. An exotherm occurs after 15 minutes and the reaction is complete after 2 hours as evidenced by infrared spectroscopy. The following TEOS macromer is obtained ##STR9## as a low viscosity liquid, MW 508.72, which is stable at room temperature. The reaction is conducted under nitrogen at room temperature in a glass vessel with mechanical stirring the reaction is complete after 2 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-Propanediol (2.9 g, 38.0 mmol) is reacted with 3-isocyanatopropyltriethoxy silane (16.4 g, 76.0 mmol) and 0.2% dibutyltin dilaurate catalyst. The reaction is conducted under nitrogen at room temperature in a glass vessel with mechanical stirring. An exotherm occurs after 15 minutes and the reaction is complete after 2 hours as evidenced by infrared spectroscopy. The following TEOS macromer is obtained ##STR9## as a low viscosity liquid, MW 508.72, which is stable at room temperature. The reaction is conducted under nitrogen at room temperature in a glass vessel with mechanical stirring the reaction is complete after 2 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Isocyanatopropyltriethoxysilane (12.4 g, 50 mmol) is added dropwise over a period of 25 minutes to vigorously stirred 3-aminopropyltriethoxy-silane (11.6 g, 50 mmol). After sixty minutes, the exothermic reaction is complete yielding a white waxy solid with the following structure: ##STR7## After sixty minutes the exothermic reaction is complete yielding a white waxy solid with the following structure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Isocyanatopropyltriethoxysilane (12.4 g, 50 mmol) is added dropwise over a period of 25 minutes to vigorously stirred 3-aminopropyltriethoxy-silane (11.6 g, 50 mmol). After sixty minutes, the exothermic reaction is complete yielding a white waxy solid with the following structure: ##STR7## After sixty minutes the exothermic reaction is complete yielding a white waxy solid with the following structure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 3-isocyanatopropyltriethoxysilane (74 g; 0.31 mole) was slowly added 30 g (0.30 mole) of N,N-dimethyl-1,3-propanediamine. There was a significant exotherm. The product was purified by strip distillation at 205° C. (0.1 torr). NMR (CDCl3) 0.40-0.9 (m; 2H), 1.22 (t; 9H), 1.4-1.9 (m; 4H), 2.21 (s; 6H), 2.33 (t; 2H), 2.9-3.4 (m; 4H), 3.81 (q; 6H), 5.8 (b, 2H) ppm. IR (neat film) 3340, 2980, 2940, 1635, 1575, 1105, 1080, 960, 780 cm-1. The product was purified by strip distillation at 205° C. (0.1 torr)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloroethylamine hydrochloride (73.86 g, 0.70 mol, 1.00 eq) is initially charged in ethanol (2.0 l) in a 4 l three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to −78° C., and sodium ethoxide (226.83 g, 0.70 mol, 1.00 eq, 21% in ethanol) is added. 3-Isocyanatopropyl(triethoxysilane) (173.15 g, 0.70 mol, 1.00 eq) is then added dropwise at −78 to −65° C. within 3 h and then the mixture is heated to 50° C. Potassium thioacetate (79.95 g, 0.70 mol, 1.00 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 4 h, the mixture is cooled to room temperature and the suspension is filtered. The filtrate is freed of the solvent on a rotary evaporator and dried under reduced pressure. The (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—S—CH2CH3 product (288.02 g, quant.) is obtained as an orange oil. reflux condenser the mixture is heated to 50° C the mixture is heated to reflux After a reaction time of 4 h, the mixture is cooled to room temperature the suspension is filtered The filtrate is freed of the solvent on a rotary evaporator dried under reduced pressure

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloroethylamine hydrochloride (73.86 g, 0.70 mol, 1.00 eq) is initially charged in ethanol (2.0 l) in a 4 l three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to −78° C., and sodium ethoxide (226.83 g, 0.70 mol, 1.00 eq, 21% in ethanol) is added. 3-Isocyanatopropyl(triethoxysilane) (173.15 g, 0.70 mol, 1.00 eq) is then added dropwise at −78 to −65° C. within 3 h and then the mixture is heated to 50° C. Potassium thioacetate (79.95 g, 0.70 mol, 1.00 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 4 h, the mixture is cooled to room temperature and the suspension is filtered. The filtrate is freed of the solvent on a rotary evaporator and dried under reduced pressure. The (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—S—CH2CH3 product (288.02 g, quant.) is obtained as an orange oil. reflux condenser the mixture is heated to 50° C the mixture is heated to reflux After a reaction time of 4 h, the mixture is cooled to room temperature the suspension is filtered The filtrate is freed of the solvent on a rotary evaporator dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A ten gram sample of N"-[2-hydroxy-3-[3-(trimethoxysilyl)propoxy]propyl]-N,N,N',N'-tetramethylguanidine, prepared in Example 2, was dissolved in 5 g of toluene. To this solution was added, under a stream of argon gas, 7.1 g of 3-isocyanatopropyltriethoxysilane. The resulting mixture was stirred at ambient temperature for one hour. At the end of this time, analysis of the reaction mixture by infrared spectroscopy indicated the absence of hydroxyl function. The reaction mixture, containing 71% by weight of [3-(triethoxysilyl)propyl]carbamic acid, [2-[[bis(dimethylamino)methylene]amino]-1-[[3-(trimethoxysilyl)propoxy]methyl]ethyl]ester, was used without further puriofication as an accelerator.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, [C4F9SO2N(CH3)CH2]2CHOC(O)NH(CH2)3Si(OCH2CH3)3 was prepared as follows. A three-necked round bottom 500 ml flask fitted with a stirrer, heating mantle, condenser, nitrogen inlet, Dean-Stark trap and thermometer was charged with about 204.6 grams of the [C4F9SO2N(CH3)CH2]2CHOH (0.3 mol), and about 250 grams methyl ethyl ketone. The mixture was heated for about 1 hour at about 100° C. and about 50 grams of material was removed using the Dean-Stark trap. The mixture was cooled to about 30° C., and about 74.4 grams of OCN(CH2)3Si(OCH2CH3)3 (0.3 mol), and three drops of stannous octanoate were added. The resulting mixture was heated at about 75° C. under nitrogen for about 16 hours. A three-necked round bottom 500 ml flask fitted with a stirrer heating mantle, condenser, nitrogen inlet, Dean-Stark trap and thermometer about 50 grams of material was removed The mixture was cooled to about 30° C. The resulting mixture was heated at about 75° C. under nitrogen for about 16 hours

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, [C4F9SO2N(CH3)CH2]2CHOC(O)NH(CH2)3Si(OCH2CH3)3 was prepared as follows. A three-necked round bottom 500 ml flask fitted with a stirrer, heating mantle, condenser, nitrogen inlet, Dean-Stark trap and thermometer was charged with about 204.6 grams of the [C4F9SO2N(CH3)CH2]2CHOH (0.3 mol), and about 250 grams methyl ethyl ketone. The mixture was heated for about 1 hour at about 100° C. and about 50 grams of material was removed using the Dean-Stark trap. The mixture was cooled to about 30° C., and about 74.4 grams of OCN(CH2)3Si(OCH2CH3)3 (0.3 mol), and three drops of stannous octanoate were added. The resulting mixture was heated at about 75° C. under nitrogen for about 16 hours. A three-necked round bottom 500 ml flask fitted with a stirrer heating mantle, condenser, nitrogen inlet, Dean-Stark trap and thermometer about 50 grams of material was removed The mixture was cooled to about 30° C. The resulting mixture was heated at about 75° C. under nitrogen for about 16 hours