US 11,891,476 B2
Phenalkamine epoxy curing agents from methylene bridged poly(cyclohexyl-aromatic) amines and epoxy resin compositions containing the same
Gauri Sankar Lal, Whitehall, PA (US); and Michael Cook, Macungie, PA (US)
Assigned to Evonik Operations GmbH, Essen (DE)
Filed by Evonik Operations GmbH, Essen (DE)
Filed on Oct. 22, 2020, as Appl. No. 17/076,866.
Claims priority of provisional application 62/933,024, filed on Nov. 8, 2019.
Prior Publication US 2021/0139642 A1, May 13, 2021
Int. Cl. C08G 59/62 (2006.01); C08G 59/40 (2006.01); C08G 59/50 (2006.01); C09D 163/00 (2006.01)
CPC C08G 59/623 (2013.01) [C08G 59/4014 (2013.01); C08G 59/5033 (2013.01); C09D 163/00 (2013.01)] 5 Claims
 
1. A curing agent composition comprising a phenalkamine mixture comprising six phenalkamines of formulas (VII), (VIII), (IX), (X), (XI), and (XII):

OG Complex Work Unit Chemistry
wherein n=0, 2, 4, or 6; and R′=H, C1-C10 alkyl, Ph, a C5-C6 cycloaliphatic group, or a C5-C10 aromatic group and further comprising an additional amine having at least two amine functionalities selected from
diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), hexamethylenediamine (HMDA), 1,3-pentanediamine, 2-methyl-1,5-pentanediamine, triaminononane, N-(2-aminoethyl)-1,3-propanediamine (N3-Amine), N,N′-1,2-ethanediylbis-1,3-propanediamine (N4-amine), dipropylenetriamine; an arylaliphatic amine, m-xylylenediamine (mXDA), p-xylylenediamine, a cycloaliphatic amine, 1,3-bis(aminomethyl)cyclohexylamine (1,3-BAC), isophorone diamine (IPDA), 4,4′-methylenebiscyclohexanamine, 1,2-diaminocyclohexylamine (DCHA), aminopropylcyclohexylamine (APCHA), a methylene bridged poly (cycloaliphatic-aromatic) amine, an aromatic amine, m-phenylenediamine, diaminodiphenylmethane (DDM), diaminodiphenylsulfone (DDS); a polyalkoxyamine where the alkoxy group can be an oxyethylene, oxypropylene, oxy-1,2-butylene, oxy-1,4-butylene or co-polymers thereof, 4,7-dioxadecane-1,10-diamine, I-propanamine, 3,3′-(oxybis(2,1-ethanediyloxy))bis(diaminopropylated diethylene glycol), poly(oxy-(methyl-1,2-ethanediyl)), α-(2-aminomethylethyl) ω-(2-aminomethylethoxy), triethyleneglycoldiamine and oligomers, poly(oxy(methyl-1,2-ethanediyl)), αα′-(oxydi-2,1-ethanediyl)bis(ω-(aminomethylethoxy)), bis(3-amino-propyl)polytetrahydrofuran 350, bis(3-aminopropyl)polytetrahydrofuran 750, poly(oxy(methyl-1,2-ethanediyl)), α-hydro-ω-(2-aminomethylethoxy)ether with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (3:I), and diaminopropyldiaminopropyl dipropylene glycol,
amidoamine and polyamide curing agents and
Mannich bases of phenolic compounds with amines and formaldehyde.