Aziridinyl functional compound
The present invention relates to compound (I) comprising at least one functional group A and at least one functional group B, wherein the functional groups A has structural formula A: wherein R 1 is H, R 2 , R 3 and R 4 are independently chosen from H, methyl or ethyl, m is 1-6; and the functional groups B has structural formula B: R 5 is H or methyl, X is O or NH, Z′ is a polyalkoxy group or an omega-alkoxy polycaprolacton group, Y′ is a collection of atoms covalently connected in linear or branched configuration n″ is 0 or 1, and m′ is an integer from 1-6; with the proviso that the summed amount of the number of functional groups A and the number of functional groups B in compound (I) is from 2-13; and the compound has a molecular weight in the range from 800-10000 Dalton.
1 . A compound (I) having a molecular weight, determined using MALDI-TOF mass spectrometry, in a range from 600 to 5000 Dalton, consisting of a), b) and c), wherein a) a group W, b) at least one functional group A, and c) at least one functional group B, and wherein each one of the functional groups A and B is connected to the group W, and wherein a summed amount of the number of functional groups A and the number of functional groups B in compound (I) is from 2 to 13,
and wherein
the group W consists of at least one functionality selected from the group consisting of aliphatic hydrocarbon functionality, cycloaliphatic hydrocarbon functionality, aromatic hydrocarbon functionality, isocyanurate functionality, iminooxadiazindione functionality, ether functionality, ester functionality, amide functionality, carbonate functionality, urethane functionality, urea functionality, biuret functionality, allophanate functionality, uretdione functionality and any combination thereof,
and wherein
the functional groups A has structural formula A:
wherein
R 1 is H,
R 2 , R 3 and R 4 are independently chosen from H, methyl or ethyl,
m is 1 to 6,
R′ and R″ are according to (1) or (2):
(1) R′=H or an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms, and
R″=H, an aliphatic hydrocarbon group containing from 1 to 14 carbon atoms, a cycloaliphatic hydrocarbon group containing from 5 to 12 carbon atoms, an aromatic hydrocarbon group containing from 6 to 12 carbon atoms, CH 2 0 (C═O) R′″, CH 2 —O R″″, or CH 2 (OCR″″HCR′″″H)˜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,
(2) R′ and R″ form together a saturated cycloaliphatic hydrocarbon group containing from 5 to 8 carbon atoms; and
the functional groups B has structural formula B:
m′ is an integer from 1 to 6, R 5 is H or methyl, X is O or NH, and
Y′ is a collection of at most 100 atoms covalently connected in linear or branched configuration which collection of atoms consists of i) carbon and hydrogen atoms, or ii) carbon, hydrogen and oxygen atoms.
2 . The compound (I) of claim 1 , wherein R 2 is H, R 3 is CH 3 and R 4 is H.
3 . The compound according to claim 1 , wherein m is 1, R′ is H and R″=an alkyl group containing from 1 to 4 carbon atoms.
4 . The compound (I) of claim 1 , wherein R 5 is H.
5 . The compound (I) of claim 1 , wherein X is O.
6 . The compound (I) of claim 1 , wherein the summed amount of the number of functional groups A and the number of functional groups B in compound (I) is from 3 to 10.
7 . The compound (I) of claim 1 , wherein the molecular weight is in a range of from 600 Daltons to 3800 Daltons.
8 . A 100% radiation curable composition containing less than 5 wt. % of water and volatile organic solvent by weight of a solids content of the composition and comprises i) at least one compound (I) of claim 1 , and ii) at least one compound (II) selected from the group consisting of polyester (meth)acrylates, polyether (meth)acrylates, epoxy (meth)acrylates, amino (meth)acrylates, polycarbonate (meth)acrylates, (poly)urethane (meth)acrylates, and (meth)acrylated (meth)acrylics.
9 . The composition of claim 8 , wherein the compound (II) has (meth)acryloyl ester groups.
10 . The composition of claim 8 , wherein the compound (II) has acryloyl ester groups.
11 . The composition of claim 8 , wherein the amount of the compound (I) is least 2 wt. % and at most 40 wt. % relative to a total amount of the composition, and an amount of compound (II) is at least 60 wt. % and at most 90 wt. %, relative to the total amount of the composition.
12 . The composition of claim 8 , wherein a molar ratio of aziridinyl groups of the following structural formula
to ethylenically unsaturated bonds in the compound (I) is in a range of from 1:5 to 1:1.
13 . The composition of claim 8 , wherein the composition is UV-curable.
14 . An ink composition comprising the composition of claim 8 .