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US 5,296,570 AGranted
Curable mixtures of mesogenic epoxy resins and mesogenic polyamines and cured compositions
AssigneeThe Dow Chemical Company
InventorsJimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
Life of this patent
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Abstract
Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
Claims16
A product resulting from curing a curable composition comprising
- (I) an advanced epoxy resin prepared by reacting
- (A) one or more epoxy resins containing one or more rodlike mesogenic moieties, said epoxy resin being those represented by either the following Formula I ##STR38## wherein at least about 80 percent of the --(Z.sup.1 --Z.sup.2).sub.n --Z.sup.1 -- linkages and the glycidyl ether groups are in the para position with respect to each other;
- each R and R.sup.1 is independently hydrogen or an aliphatic hydrocarbon group having from 1 to about 4 carbon atoms;
- each X is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 12 carbon atoms, a halogen atom, --NO.sub.2, or --C.ident.N;
- each Z.sup.1 is independently --CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.N--N.dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CO--O--CH.sub.2 --, --CR.sup.1 .dbd.CR.sup.1 --CO--O--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CH.sub.2 --CH.sub.2 --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CO--O--, --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CO--NR.sup.1 --, --NR.sup.1 --CO--, --CO--NR.sup.1 --NR.sup.1 --CO--, --C.ident.C--, --C.ident.C--C.ident.C--, --N.dbd.N--, --CO--S--, --S--CO--, --CR.sup.1 .dbd.CR.sup.1 --O--CO--CH.sub.2 --, --CH.sub.2 --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --O--CO--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CH.sub.2 --CH.sub.2 --CO--O--, --O--CO--CH.sub.2 --CH.sub.2 --, --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup. 1 .dbd.CR.sup.1 --O--CO--, a direct single bond when n.gtoreq.1, ##STR39## Z.sup.2 is a group represented by a cyclic or bicyclic ring system containing from 5 to about 12 carbon atoms and is cycloaliphatic, polycycloaliphatic, aromatic or a combination thereof;
- n is 0 to 2;
- each Z' is independently a --CO--, --O--CO--, --CO--O--, --CO--NR.sup.1 --, or --NR.sup.1 --CO-- group and each n' independently has a value of zero or one;
- with the proviso that each Z.sup.1 can also independently be ##STR40## --CR.sup.1 .dbd.N--, --N.dbd.CR.sup.1 --, --CO--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CO--, --CO--O--, or --O--CO-- when Z.sup.2 is not a benzene ring and when n.noteq.0;
- or the following Formula II ##STR41## wherein Z.sup.3 is ##STR42## and Z.sup.4 is --CO--O--, --O--CO--, --NR.sup.1 --CO-- or --CO--NR.sup.1 --;
- X.sup.1 is a divalent hydrocarbyl group having from 1 to about 10 carbon atoms which can optionally contain one or more heteroatoms selected from N, O or S and is saturated or unsaturated or X.sup.1 is a direct bond;
- wherein R, R1 and X are as hereinbefore defined, or any combination of any two or more epoxy resins represented by the aforementioned Formulas I and II;
- with
- (B) at least one compound having an average of more than one active hydrogen atom per molecule;
- and
- wherein components (A) and (B) are employed in quantities which provide a ratio of active hydrogen atoms per epoxide group of from about 0.01:1 to about 0.95:1;
- and
- (II) a curing amount of one or more polyamines containing one or more rodlike mesogenic moieties.
14 more elements
A product resulting from curing a curable composition comprising (I) a blend comprising
- (A) an advanced epoxy resin prepared by reacting
- (1) one or more epoxy resins containing one or more rodlike mesogenic moieties, said epoxy resin being those represented by either the following Formula I ##STR45## wherein at least about 80 percent of the --(Z.sup.1 --Z.sup.2).sub.n --Z.sup.1 -- linkages and the glycidyl ether groups are in the para position with respect to each other;
- each R and R.sup.1 is independently hydrogen or an aliphatic hydrocarbon group having from 1 to about 4 carbon atoms;
- each X is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 12 carbon atoms, a halogen atom, --NO.sub.2, or --C.ident.N;
- each Z.sup.1 is independently --CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.N--N.dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CO--O--CH.sub.2 --, --CR.sup.1 .dbd.CR.sup.1 --CO--O--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CH.sub.2 --CH.sub.2 --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd. CR.sup.1 --CO--O--, --O--CO--CR.sup.1 .dbd.CR.sup.1 --, --CO--NR.sup.1 --, --NR.sup.1 --CO--, --CO--NR.sup.1 --NR.sup.1 --CO--, --C.ident.C--, --C.ident.C--C.ident.C--, --N.dbd.N--, --CO--S--, --S--CO--, --CR.sup.1 .dbd.CR.sup.1 --O--CO--CH.sub.2 --, --CH.sub.2 --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --O--CO--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CH.sub.2 --CH.sub.2 --CO--O--, --O--CO--CH.sub.2 --CH.sub.2 --, --CO--O--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --O--CO--, a direct single bond when n.gtoreq.1, ##STR46## Z.sup.2 is a group represented by a cyclic or bicyclic ring system containing from 5 to about 12 carbon atoms and is cycloaliphatic, polycycloaliphatic, aromatic or a combination thereof;
- n is 0 to 2;
- each Z' is independently a --CO--, --O--CO--, --CO--O--, --CO--NR.sup.1 --, or --NR.sup.1 --CO-- group and each n' independently has a value of zero or one;
- with the proviso that each Z.sup.1 can also independently be ##STR47## --CR.sup.1 .dbd.N--, --N.dbd.CR.sup.1 --, --CO--CR.sup.1 .dbd.CR.sup.1 --, --CR.sup.1 .dbd.CR.sup.1 --CO--, --CO--O--, or --O--CO-- when Z.sup.2 is not a benzene ring and when n.noteq.0;
- or the following Formula II ##STR48## wherein Z.sup.3 is ##STR49## and Z.sup.4 is --CO--O--, --O--CO--, --NR.sup.1 --CO-- or --CO--NR.sup.1 --;
- X.sup.1 is a divalent hydrocarbyl group having from 1 to about 10 carbon atoms which can optionally contain one or more heteroatoms selected from N, O or S and is saturated or unsaturated or X.sup.1 is a direct bond;
- wherein R, R1 and X are as hereinbefore defined;
- or any combination of any two or more epoxy resins represented by the aforementioned Formulas I and II;
- with
- (2) at least one compound having an average of more than one active hydrogen atom per molecule;
- and
- wherein components (1) and (2) are employed in quantities which provide a ratio of active hydrogen atoms per epoxide group of from about 0.01:1 to about 0.95:1;
- and
- (B) one or more polyepoxides which are substantially free of rodlike mesogenic moieties;
- and (II) a curing amount of one or more polyamines containing one or more rodlike mesogenic moieties.
16 more elements
Dependencies are inferred from the claim text.