Ammonia → HCID 21966223, compound

Temperature

110 °C

Next, 150.0 parts by weight of a 17.3% aqueous solution of sodium sulfide was added dropwise over 4.5 hours at 5° C. to 42° C., and subsequently, the mixture was stirred for 40 minutes. Production of a tetraol compound of formula (4) was confirmed from NMR data. Next, 117.4 parts by weight of thiourea having a purity of 99.90% was introduced, and 84.3 parts by weight of hydrochloric acid gas having a purity of 90.7% was blown therein. The mixture was stirred for 3 hours under reflux at 110° C., and thereby a reaction which forms thiuronium salt was carried out. The reaction mixture was cooled to 45° C., and then 214.0 parts by weight of toluene was added thereto, and the mixture was cooled to 26° C. 158.4 parts by weight of a 25 wt % aqueous ammonia solution was introduced over 25 minutes at 26° C. to 46° C., and a hydrolytic reaction was carried out by aging the mixture for 1 hour at 54° C. to 62° C. Thus, a toluene solution of a polythiol containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components was obtained. 59.4 parts by weight of 36% hydrochloric acid was added to the toluene solution, and acid washing for 30 minutes at 33° C. to 40° C. was performed two times. 118.7 parts by weight of degassed water (dissolved oxygen concentration: 2 ppm) was added thereto, and washing for 30 minutes at 35° C. to 45° C. was performed five times. Toluene and a trace amount of water were removed under heating at reduced pressure, and then the residue was filtered under reduced pressure using a 1.2 μm PTFE type membrane filter, and thus 115.0 parts by weight of a polythiol compound containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components was obtained. The properties of the polythiol compound thus obtained are shown in Table-1. Measurement of the viscosity after 7 hours of the polymerizable composition was carried out in the same manner as in Example C-1. The results are shown in Table-2.

1. stirringThe mixture was stirred for 3 hours
2. customa reaction which
3. temperatureThe reaction mixture was cooled to 45° C.
4. temperaturethe mixture was cooled to 26° C
5. customa hydrolytic reaction
6. customfor 1 hour
7. customat 54° C. to 62° C
8. customwas obtained
9. washwashing for 30 minutes at 33° C. to 40° C.
10. addition118.7 parts by weight of degassed water (dissolved oxygen concentration: 2 ppm) was added
11. washwashing for 30 minutes at 35° C. to 45° C.
12. customToluene and a trace amount of water were removed
13. temperatureunder heating at reduced pressure
14. filtrationthe residue was filtered under reduced pressure
15. filtrationfilter
16. additionthus 115.0 parts by weight of a polythiol compound containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components
17. customwas obtained
18. customThe properties of the polythiol compound thus obtained
19. customafter 7 hours

ORD record

ord-de7e1d1e5a4f4474aedba14b13573685

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181180B2