Trimethylolpropane tris(2-methyl-1-aziridinepropionate) synthesis

Yield:-

Reaction Conditions:

Stage #1: 1,1,1-tri(hydroxymethyl)propane;acrylic acidwith hydroquinone in toluene at 50 - 80; for 6 h;
Stage #2: with hydroquinone at 60; for 1 h;
Stage #3: 2-Methylaziridine at 5 - 20; for 28 h;Darkness;

Steps:

1 Example 1

(1) 72 g of acrylic acid and 32 g of trimethylol propane were homogeneously mixed,Followed by the addition of cerium sulfate 1.8-2.5 grams,0.4 g of hydroquinone and 60 g of toluene;(2) heating to 50 ° C with stirring, introducing air for about 2 hours,And heated to reflux at 80 ° C for about 4 hours,The whole process to keep stirring;(3) After cooling to 60 ° C, 45 ml of water was added,After stirring for 20 minutes, the mixture was allowed to stand for 15 minutes or longer,After layering to remove the lower liquid;(4) the upper liquid,Washed twice with a sodium hydroxide solution having a concentration of 15% by mass,And then washed with saturated sodium chloride solution 2 to 3 times,And finally washed with water 2 to 3 times;(5) heated to about 60 ° C for half an hour,Then add 0.1 g of hydroquinone,Rotary steam for 30 minutes,Get light yellow transparent liquid;(6) light yellow transparent liquid 60 grams placed in an ice bath (5 below),A solution of 26 g of 2-methylaziridine,About 4 hours to drop finished,Half an hour later moved to a brown bottle;(7) was allowed to stand at room temperature for 24 hours,Trimethylolpropane - tris (2-methyl-1-aziridinyl) propionate;(8) Trimethylolpropane-tris (2-methyl-1-aziridinyl) propionate The peel strength of the peelable protective film obtained by curing the aqueous polyurethane dispersion is 300 to 500 N / m.

References:

CN106220543,2016,A Location in patent:Paragraph 0006; 0007; 0008