	US 12,281,072 B2
	Multi-aziridine compound
Gerardus Cornelis Overbeek, Geleen (NL); Patrick Johannes Maria Stals, Geleen (NL); Daan Van Der Zwaag, Geleen (NL); Alfred Jean Paul Bückmann, Geleen (NL); and Josephus Christiaan Van Oorschot, Geleen (NL)
Assigned to Covestro (Netherlands) B.V., Geleen (NL)
Appl. No. 17/794,440
Filed by COVESTRO (NETHERLANDS) B.V., Geleen (NL)
PCT Filed Jan. 21, 2021, PCT No. PCT/EP2021/051392 § 371(c)(1), (2) Date Jul. 21, 2022, PCT Pub. No. WO2021/148570, 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 2023/0127229 A1, Apr. 27, 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) at least 2 of the following structural units (A):

whereby

R₁is H;

R₂and R₄are independently chosen from H, a linear group containing from 1 to 8 carbon atoms and optionally containing one or more heteroatoms, a branched or cyclic group containing from 3 to 8 carbon atoms and optionally containing one or more heteroatoms, phenyl, benzyl, or pyridinyl;

R₃is chosen from a linear group containing from 1 to 8 carbon atoms and optionally containing one or more heteroatoms, a branched or cyclic group containing from 3 to 8 carbon atoms and optionally containing one or more heteroatoms, phenyl, benzyl, or pyridinyl;

or R₂and R₃(in case R₂is different than H) may be part of the same cyclic group containing from 3 to 8 carbon atoms;

R′ and R″ are independently H or an aliphatic hydrocarbon group containing from 1 to 12 carbon atoms; and

b) a molecular weight of from 600 to 20000 Daltons, wherein the molecular weight is determined using MALDI-TOF mass spectrometry; and

the multi-aziridine compound is obtained by reacting at least a polyisocyanate and a compound (B) with the following structural formula:

D]_n

whereby n is an integer equal to or larger than 2, Z is an n-valent radical or a mixture of n-valent radicals and D has the following structural formula:

whereby the molar ratio of moiety D to isocyanate moieties on polyisocyanates is from 0.5 to 2.