US 12,146,030 B2
Method for producing non-isocyanate polyurethanes
Jose Garcia Miralles, Duesseldorf (DE); Maryluz Moreno Rueda, Tarragona (ES); Zeynep Beyazkilic, Tarragona (ES); Raquel Gavara Castell, Nules (ES); and Xavier Elias Pera, Terrassa (ES)
Assigned to Henkel AG & Co. KGaA, Duesseldorf (DE)
Filed by Henkel AG & Co. KGaA, Duesseldorf (DE)
Filed on Jun. 29, 2021, as Appl. No. 17/362,110.
Application 17/362,110 is a continuation of application No. PCT/EP2019/084398, filed on Dec. 10, 2019.
Claims priority of application No. 19382006 (EP), filed on Jan. 4, 2019.
Prior Publication US 2021/0324141 A1, Oct. 21, 2021
Int. Cl. C08G 71/04 (2006.01); C07D 209/42 (2006.01); C07D 235/30 (2006.01); C07D 295/135 (2006.01)
CPC C08G 71/04 (2013.01) [C07D 209/42 (2013.01); C07D 235/30 (2013.01); C07D 295/135 (2013.01)] 8 Claims
 
1. A method for producing a non-isocyanate-based polyurethane, comprising:
(1) providing a cyclic carbonate component,
(2) providing an amine component selected from the group consisting of a primary amine, a secondary amine, and combination thereof, and
(3) providing a single catalyst component that performs the ring opening reaction of the cyclic carbonate component with the amine component, selected from the group consisting of:
(a) an amidoindole derivative represented by Formula (I),

OG Complex Work Unit Chemistry
wherein R1 and R2 each independently represents a hydrogen, a halogen, a nitro group, a cyano group, a hydroxyl group, a C1-C6 alkyl group, a halo-C1-C6 alkyl group, a hydroxy-C1-C6 alkyl group, a cyclo-C3-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a halo-C1-C6 alkoxy group, an ester group, a carbonyl group, a C1-C6-alkoxycarbonyl group, an aryloxycarbonyl group, a C1-C6-alkylsulfinyl group, an arylsulfinyl group, a C1-C6-alkylsulfonyl group, an arylsulfonyl groups, or a sulfamoyl group,
(b) a benzimidazole derivative represented by Formula (II),

OG Complex Work Unit Chemistry
wherein R3 and R4 each independently represents a hydrogen, a halogen, a nitro group, a cyano group, a hydroxyl group, a C1-C6 alkyl group, a halo-C1-C6 alkyl group, a hydroxy-C1-C6 alkyl group, a cyclo-C3-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a halo-C1-C6 alkoxy group, an ester group, a carbonyl group, a C1-C6-alkoxycarbonyl group, an aryloxycarbonyl group, a C1-C6-alkylsulfinyl group, an arylsulfinyl group, a C1-C6-alkylsulfonyl group, an arylsulfonyl groups, or a sulfamoyl group, and
(c) a squaramide derivative represented by Formula (III),

OG Complex Work Unit Chemistry
wherein R5 and R6 each independently represents a hydrogen, a halogen, a nitro group, a cyano group, a hydroxyl group, a C1-C6 alkyl group, a halo-C1-C6 alkyl group, a hydroxy-C1-C6 alkyl group, a cyclo-C3-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a halo-C1-C6 alkoxy group, an ester group, a carbonyl group, a C1-C6-alkoxycarbonyl group, an aryloxycarbonyl group, a C1-C6-alkylsulfinyl group, an arylsulfinyl group, a C1-C6-alkylsulfonyl group, an arylsulfonyl groups, or a sulfamoyl group, and
R7 represents a cyclo-C3-C6 alkyl group, a phenyl, a naphthyl, or a 5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from N, O, and S, optionally substituted by a halogen, a nitro group, a cyano group, a hydroxyl group, a C1-C6 alkyl group, a halo-C1-C6 alkyl group, a hydroxy-C1-C6 alkyl group, a cyclo-C3-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a halo-C1-C6 alkoxy group, a phenyl, a naphthyl, or a 5-10 membered heteroaryl consisting of carbon atoms and 1-3 heteroatoms selected from N, O, and S.