US 12,077,652 B2
Oxidatively curable coating composition
Johannes Wietse De Boer, Leiden (NL); Ronald Hage, Leiden (NL); Karin Maaijen, Leiden (NL); Yfranka Petronella Areke Roelofsen, Leiden (NL); and Peter Comba, Heidelberg (DE)
Assigned to Milliken Industrials Limited, Wigan (GB)
Appl. No. 17/257,502
Filed by Milliken Industrials Limited, Wigan (GB)
PCT Filed Jul. 4, 2019, PCT No. PCT/GB2019/051901
§ 371(c)(1), (2) Date Dec. 31, 2020,
PCT Pub. No. WO2020/008205, PCT Pub. Date Jan. 9, 2020.
Claims priority of application No. 18181908 (EP), filed on Jul. 5, 2018.
Prior Publication US 2022/0073701 A1, Mar. 10, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C08K 5/3432 (2006.01); C09D 167/08 (2006.01)
CPC C08K 5/3432 (2013.01) [C09D 167/08 (2013.01)] 13 Claims
 
1. A formulation comprising an oxidatively curable alkyd-based resin and a chelant of the formula (I) or formula (II):

OG Complex Work Unit Chemistry
wherein:
each D is independently selected from the group consisting of thiazol-2-yl, thiazol-4-yl, pyrazin-2-yl, quinolin-2-yl, pyrazol-3-yl, pyrazol-1-yl, pyrrol-2-yl, imidazol-2-yl, imidazol-4-yl, benzimidazol-2-yl, pyrimidin-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl and 1,2,3-triazol-4-yl, each of which may be optionally substituted by one or more groups independently selected from the group consisting of —F, —Cl, —Br, —OH, —OC1-C4alkyl, —NH—CO—H, —NH—CO—C1-C4alkyl, —NH2, —NH—C1-C4alkyl, and —C1-C4alkyl;
each E is independently selected from the group consisting of pyridin-2-yl, thiazol-2-yl, thiazol-4-yl, pyrazin-2-yl, quinolin-2-yl, pyrazol-3-yl, pyrazol-1-yl, pyrrol-2-yl, imidazol-2-yl, imidazol-4-yl, benzimidazol-2-yl, pyrimidin-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl and 1,2,3-triazol-4-yl, each of which may be optionally substituted by one or more groups independently selected from the group consisting of —F, —Cl, —Br, —OH, —OC1-C4alkyl, —NH—CO—H, —NH—CO—C1-C4alkyl, —NH2, —NH—C1-C4alkyl, and —C1-C4alkyl;
R1 and the or each R2 are independently selected from the group consisting of C1-C24alkyl, C6-10arylC1-C6alkyl, C6-10aryl, C5-C10heteroarylC1-C6alkyl, each of which may be optionally substituted by one or more groups selected from —F, —Cl, —Br, —OH, —OC1-C4alkyl, —NH—CO—H, —NH—CO—C1-C4alkyl, —NH2, —NH—C1-C4alkyl and —SC1-C4alkyl; and CH2CH2N(R8)(R9),
wherein N(R8)(R9) is selected from the group consisting of di(C1-44alkyl)amino; di(C6-10aryl)amino in which each of the aryl groups is independently optionally substituted with one or more C1-20alkyl groups; di(C6-10arylC1-6alkyl)amino in which each of the aryl groups is independently optionally substituted with one or more C1-20alkyl groups; NR7, in which R7 and the nitrogen atom N to which it is attached represent a heterocycloalkyl group optionally substituted with one or more C1-20alkyl groups, which is connected to the remainder of R1 or R2 through the nitrogen atom N; di(heterocycloalkylC1-6alkyl)amino, in which each of the heterocycloalkyl groups is independently optionally substituted with one or more C1-20alkyl groups; and di(heteroarylC1-6alkyl)amino, wherein each of the heteroaryl groups is independently optionally substituted with one or more C1-20alkyl groups;
R3 and R4 are independently selected from hydrogen, C1-C8alkyl, C1-C8alkyl-O—C1-C8alkyl, C6-C10aryloxyC1-C8alkyl, C6-C10aryl, C1-C8hydroxyalkyl, C6-C10arylC1-C6alkyl and C5-C10heteroarylC1-C6alkyl, and —(CH2)0-4C(O)OR5 wherein R5 is independently selected from: hydrogen, C1-C8alkyl and C6-10aryl;
Q represents a bridge selected from the group consisting of a C1-6alkylene moiety, a C6-10arylene moiety or a moiety comprising one or two C1-3alkylene units and one C6-10arylene unit, which bridge is optionally substituted one or more times with independently selected C1-24alkyl groups and OH groups; and
X is selected from C═O, —[C(R6)2]0-3- wherein each R6 is independently selected from hydrogen, hydroxyl, C1-C4alkoxy and C1-C4alkyl; and
wherein the formulation comprises less than 0.00005% by weight of ions of each of vanadium and copper.