US 12,359,070 B2
Naphthalocyanine and phthalocyanine chromophores
Hans Reichert, Basel (CH); Rene Fischer, Basel (CH); Marie-Pascale Perritaz, Schweizerhalle (CH); Helmut Reichelt, Ludwigshafen am Rhein (DE); Oliver Seeger, Ludwigshafen am Rhein (DE); and Korinna Dormann, Ludwigshafen am Rhein (DE)
Assigned to BASF SE, Ludwigshafen am Rhein (DE)
Appl. No. 17/430,150
Filed by BASF SE, Ludwigshafen am Rhein (DE)
PCT Filed Feb. 10, 2020, PCT No. PCT/EP2020/053342
§ 371(c)(1), (2) Date Aug. 11, 2021,
PCT Pub. No. WO2020/165099, PCT Pub. Date Aug. 20, 2020.
Claims priority of application No. 19156571 (EP), filed on Feb. 12, 2019.
Prior Publication US 2022/0098413 A1, Mar. 31, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C09B 47/067 (2006.01); B41M 3/14 (2006.01); C09B 69/10 (2006.01); C09D 11/328 (2014.01); G02B 5/22 (2006.01)
CPC C09B 47/067 (2013.01) [B41M 3/14 (2013.01); C09B 69/108 (2013.01); C09D 11/328 (2013.01); G02B 5/223 (2013.01)] 15 Claims
 
1. A printing ink formulation, comprising a compound of formula

OG Complex Work Unit Chemistry
wherein
M1 is Al(R15), or Ga(R15),
R15 is OR16;
R11 and R14 are independently of each other H, F, OR17″, SR17″, or NR17R17′,
R12 and R13 are independently of each other H, F, OR17″, SR17″, NHR17, or NR17R17′, or R12 and R13 together with the C atoms to which they are bonded form a 6-membered aromatic ring, which may optionally be substituted,
R16 is a group of formula

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
or

OG Complex Work Unit Chemistry
X1 is O, S or NH,
X2 is

OG Complex Work Unit Chemistry
w+x+y+z=4 to 20;
R9 and R10 are the same or different and are each independently hydrogen, or a methyl group;
R17, R17′ and R17″ are independently of each other a C1-C12alkyl group, (CH2CH2O)nOR18, or phenyl; or
R17 and R17′ together with the C atoms to which they are bonded form together a 5- or 6-membered saturated N-heterocyclic ring, which is optionally substituted by 1 or 2 methyl groups;
R18 is a C1-C12alkyl group;
R19 is OH, or NH2;
R20 is H, or a C1-C4alkyl group;
R30 and R31 are independently of each other hydrogen, or a C1-C4alkyl group; or
R30 and R31 form a five, or six-membered ring, which may optionally be substituted,
R32 is a C1-C25alkyl group, or a C2-C25alkenyl group,
a is 0, or 1; b is 0, or 1; b′ is 0, or 1; c is 1;
n is 0, 1, 2, 3 or 4; and
n1 is 0, or a value from 1 to 10.