Perfluoroalkyl-substituted amines as epoxy resin curing agents

An epoxy resin composition comprising:

• (1) an epoxy resin containing two or more epoxy groups per molecule and
• (2) an amine containing at least one perfluoroalkyl group and one or more primary and/or secondary amino groups per molecule of the formula:
• ##STR42## wherein R.sub.f ' is a C.sub.1 -C.sub.15 perfluoroalkyl group, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom, a C.sub.1 -C.sub.16 alkyl group, a phenyl group having or not 1 to 4 substituents selected from the group consisting of halogen atoms and C.sub.1 -C.sub.4 alkyl groups, a phenyl(C.sub.1 -C.sub.4)alkyl group having or not on the benzene ring 1 to 4 substituents selected from the group consisting of halogen atoms and C.sub.1 -C.sub.4 alkyl groups, a tri(C.sub.1 -C.sub.3)alkoxysilyl group or a C.sub.1 -C.sub.15 perfluoroalkyl group, R.sup.5 is a C.sub.1 -C.sub.8 alkylene group, --(CH.sub.2).sub.r O(C.sub.s H.sub.2s O).sub.t --(CH.sub.2).sub.r --(r, s and t being each an integer of 1 to 8), ##STR43## (R.sup.6, R.sup.7 and R.sup.8 being each a hydrogen atom, a methyl group, a methoxy group, a chlorine atom or a bromine atom), ##STR44## (R' being an oxygen atom, a sulfur atom, a sulfonyl group or a C.sub.1 -C.sub.4 alkylene, and B being a methyl group, a methoxy group, a chlorine atom or a bromine atom), ##STR45## (R.sup.9 and R.sup.10 being each a hydrogen atom, a methyl group or a methoxy group and x being an integer of 1 to 4), ##STR46## (Y being a chlorine atom or a bromine atom, y being an integer of 1 to 4 and a being an integer of 1 to 3) or ##STR47## (z being an integer of 1 to 4), A.sup.3, A.sup.4, A.sup.5 and A.sup.6 are each a C.sub.1 -C.sub.4 alkylene group, a C.sub.2 -C.sub.4 alkylene group substituted with one or two hydroxyl groups, a methyleneoxy(C.sub.3 -C.sub.4)alkylene group in which one of the hydrogen atoms in the alkylene moiety is substituted with a hydroxyl group or a phenylene group, k, k', l, l', p, p', q and q' are each 0 or 1, at least one of them being 1.

An epoxy resin composition comprising:

• (1) an epoxy resin containing two or more epoxy groups per molecule and
• (2) an amine containing at least one perfluoroalkyl group and one or more primary and/or secondary amino groups per molecule of the formula:
• ##STR49## wherein R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are each a hydrogen atom, a C.sub.1 -C.sub.16 alkyl group, a phenyl group having or not 1 to 4 substituents selected from the group consisting of halogen atoms and C.sub.1 -C.sub.4 alkyl groups, a phenyl(C.sub.1 -C.sub.4)alkyl group having or not on the benzene ring 1 to 4. substituents selected from the group consisting of halogen atoms and C.sub.1 -C.sub.4 alkyl groups, a tri(C.sub.1 -C.sub.3)alkoxysilyl group or a C.sub.1 -C.sub.15 perfluoroalkyl group, at least one of them being a perfluoroalkyl group, A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, and A.sup.7 are each a C.sub.1 -C.sub.4 alkylene group, a C.sub.2 -C.sub.4 alkylene group substituted with one or two hydroxyl groups, a methyleneoxy(C.sub.3 -C.sub.4)alkylene in which one of the hydrogen atoms in the alkylene moiety is substituted with a hydroxyl group or a phenylene group, m.sub.1, m.sub.2, m.sub.3, m.sub.4, m.sub.5, m.sub.6, m.sub.7, n.sub.1, n.sub.2, n.sub.3, n.sub.4, n.sub.5, n.sub.6 and n.sub.7 are each 0 or 1, at least one of m and n for R representing a perfluoroalkyl group being 1 and w is an integer of 1 to 10.