Epoxy-derived covalent adaptable networks and methods of their production

A method for preparing a composition comprising an epoxy-derived covalent adaptable network, comprising the following steps:

• a) providing at least one amine of formula (II) comprising primary amine groups, at least one vinylogous precursor of formula (III) comprising vinylogous precursor groups, and at least one epoxide comprising (2+a) epoxide groups
• wherein
• X1, X2 and each occurrence of X3 are individually selected from O, CR10R11 and NR12;
• R10, R11 and R12 are individually selected from H or methyl;
• W1, W2 and each occurrence of W3 each represent a functional groups so that —X1—C(═O)—W1, —X2—C(═O)—W2 and —X3—C(═O)—We constitute a vinylogous precursor group;
• B represents an amine linking moiety;
• C represents a vinylogous precursor linking moiety;
• wherein the amine linking moiety B and the vinylogous precursor linking moiety C each comprising or consisting of a group independently selected from the group consisting of alkyls, alkenyls, alkynyls, aryls, cycloalkyls and aryl alkyls, wherein one or more of the carbon atoms in the backbone of said alkyls, alkenyls, alkynyls, aryls, cycloalkyls and aryls alkyls may be replaced by a heteroatom independently selected from O, S, N and Si and/or wherein said alkyl, alkenyl, alkynyl aryl, cycloalkyl or arylalkyl may be unsubstituted or further substituted;
• a, b, and c individually represent an integer higher than or equal to 0;
• and
• b) contacting the compounds provided in step (a) thereby obtaining an epoxy-derived covalent adaptable network;
• wherein a vinylogous precursor group consists of or comprises a functional group which is capable of forming a vinylogous urethane, vinylogous amide or vinylogous urea upon reacting with a primary amine;
• wherein the average functionality F, determined before the compounds are contacted and determined over all compounds provided in step (a), is at least 2.01, the average functionality F being defined as
• F
• =
• ∑
• n
• i
• (
• 2
• +
• a
• i
• )
• +
• ∑
• n
• j
• (
• 2
• +
• b
• j
• )
• +
• ∑
• n
• k
• (
• 2
• +
• c
• k
• )
• ∑
• n
• i
• +
• ∑
• n
• j
• +
• ∑
• n
• k
• wherein ni is the number of moles of epoxide with functionality (2+ai);
• nj is the number of moles of amine of formula (II) with functionality (2+bj) and nk is the number of moles of vinylogous precursor of formula (III) with functionality (2+Ck);
• and
• wherein the ratio P, determined before the compounds are contacted and determined over all compounds provided in step (a), is more than 1, the ratio P being defined as
• P
• =
• ∑
• n
• j
• (
• 2
• +
• b
• j
• )
• ∑
• n
• i
• (
• 2
• +
• a
• i
• )
• +
• ∑
• n
• k
• (
• 2
• +
• c
• k
• )
• .