US 12,378,189 B2
Multi-aziridine compound
Patrick Johannes Maria Stals, Geleen (NL); Daan Van Der Zwaag, Geleen (NL); Alfred Jean Paul Bückmann, Geleen (NL); Gerardus Cornelis Overbeek, Geleen (NL); and Jan Van Riel, Geleen (NL)
Assigned to Covestro (Netherlands) B.V., Geleen (NL)
Appl. No. 17/791,860
Filed by COVESTRO (NETHERLANDS) B.V., Geleen (NL)
PCT Filed Jan. 21, 2021, PCT No. PCT/EP2021/051389
§ 371(c)(1), (2) Date Jul. 8, 2022,
PCT Pub. No. WO2021/148567, PCT Pub. Date Jul. 29, 2021.
Claims priority of application No. 20153154 (EP), filed on Jan. 22, 2020; application No. 20153159 (EP), filed on Jan. 22, 2020; application No. 20153239 (EP), filed on Jan. 22, 2020; application No. 20153240 (EP), filed on Jan. 22, 2020; application No. 20153242 (EP), filed on Jan. 22, 2020; application No. 20153245 (EP), filed on Jan. 22, 2020; application No. 20153246 (EP), filed on Jan. 22, 2020; application No. 20153249 (EP), filed on Jan. 22, 2020; application No. 20153250 (EP), filed on Jan. 22, 2020; application No. 20153251 (EP), filed on Jan. 22, 2020; application No. 20153253 (EP), filed on Jan. 22, 2020; application No. 20153628 (EP), filed on Jan. 24, 2020; application No. 20153630 (EP), filed on Jan. 24, 2020; and application No. 20187717 (EP), filed on Jul. 24, 2020.
Prior Publication US 2023/0097706 A1, Mar. 30, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 203/10 (2006.01); C07D 251/32 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 413/14 (2006.01); C07D 487/14 (2006.01); C08F 220/18 (2006.01); C08G 18/02 (2006.01); C08G 18/08 (2006.01); C08G 18/12 (2006.01); C08G 18/22 (2006.01); C08G 18/24 (2006.01); C08G 18/28 (2006.01); C08G 18/30 (2006.01); C08G 18/32 (2006.01); C08G 18/34 (2006.01); C08G 18/38 (2006.01); C08G 18/42 (2006.01); C08G 18/44 (2006.01); C08G 18/48 (2006.01); C08G 18/66 (2006.01); C08G 18/67 (2006.01); C08G 18/73 (2006.01); C08G 18/75 (2006.01); C08G 18/76 (2006.01); C08G 18/79 (2006.01); C08G 18/83 (2006.01); C08K 5/3412 (2006.01); C08K 5/3492 (2006.01); C08L 63/00 (2006.01); C09D 7/20 (2018.01); C09D 7/45 (2018.01); C09D 7/63 (2018.01); C09D 7/65 (2018.01); C09D 11/101 (2014.01); C09D 133/02 (2006.01); C09D 133/04 (2006.01); C09D 175/04 (2006.01); C09D 175/08 (2006.01); C09D 175/12 (2006.01)
CPC C07D 203/10 (2013.01) [C07D 251/32 (2013.01); C07D 403/12 (2013.01); C07D 403/14 (2013.01); C07D 413/14 (2013.01); C07D 487/14 (2013.01); C08F 220/1804 (2020.02); C08G 18/027 (2013.01); C08G 18/0823 (2013.01); C08G 18/0866 (2013.01); C08G 18/12 (2013.01); C08G 18/227 (2013.01); C08G 18/246 (2013.01); C08G 18/282 (2013.01); C08G 18/2825 (2013.01); C08G 18/283 (2013.01); C08G 18/2865 (2013.01); C08G 18/2875 (2013.01); C08G 18/302 (2013.01); C08G 18/3228 (2013.01); C08G 18/3231 (2013.01); C08G 18/3275 (2013.01); C08G 18/348 (2013.01); C08G 18/3842 (2013.01); C08G 18/4291 (2013.01); C08G 18/44 (2013.01); C08G 18/4808 (2013.01); C08G 18/4825 (2013.01); C08G 18/4854 (2013.01); C08G 18/4862 (2013.01); C08G 18/4879 (2013.01); C08G 18/6692 (2013.01); C08G 18/6715 (2013.01); C08G 18/73 (2013.01); C08G 18/755 (2013.01); C08G 18/758 (2013.01); C08G 18/765 (2013.01); C08G 18/792 (2013.01); C08G 18/798 (2013.01); C08G 18/833 (2013.01); C08K 5/3412 (2013.01); C08K 5/34924 (2013.01); C08K 5/34926 (2013.01); C08L 63/00 (2013.01); C09D 7/20 (2018.01); C09D 7/45 (2018.01); C09D 7/63 (2018.01); C09D 7/65 (2018.01); C09D 11/101 (2013.01); C09D 133/02 (2013.01); C09D 133/04 (2013.01); C09D 175/04 (2013.01); C09D 175/08 (2013.01); C09D 175/12 (2013.01); C08G 2150/00 (2013.01)] 22 Claims
 
1. A multi-aziridine compound having:
a) from 2 to 6 of the following structural units (A):

OG Complex Work Unit Chemistry
whereby
m is an integer from 1 to 6; and
R′ and R″ are according to (1) or (2):
(1) R′=H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms,
R″=a cycloaliphatic hydrocarbon group containing from 5 to 12 carbon atoms, an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, CH2—O—(C═O)—R′″, CH2—O—R″″, or CH2—(OCR′″″HCR′″″H)n—OR″″″, whereby R′″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″ is an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms or an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, n being from 1 to 35, R′″″ independently being H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms and R″″″ being an aliphatic hydrocarbon group containing from 1 to 4 carbon atoms, and
(2) R′ and R″ form together a saturated cycloaliphatic hydrocarbon group containing from 5 to 8 carbon atoms;
b) one or more linking chains wherein each one of these linking chains links two of the structural units A, whereby a linking chain is the shortest chain of consecutive atoms that links two structural units A; and
c) a molecular weight in the range from 840 Daltons to 5000 Daltons, wherein the molecular weight is determined using MALDI-TOF mass spectrometry.