Claims
- 1. 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.tbd.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.tbd.C--, --C.tbd.C--C.tbd.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 contain one or more heteroatoms selected from N, O or S and is saturated or unsaturated or N is a direct bond; 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.tbd.N; and n' is one; 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.
- 2. A curable composition of claim 1 wherein
- (a) when component (A) is an epoxy resin represented by Formula I, in which X is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 6 carbon atoms and when it is a halogen atom, it is chlorine or bromine;
- (b) when component (A) is an epoxy resin represented by Formula II, in which X is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 6 carbon atoms and when it is a halogen atom, it is chlorine or bromine;
- (c) component (B) is a compound represented by the following Formulas XVII or XVIII ##STR43## wherein X.sup.2 is independently a hydroxyl, carboxylic acid, --SH, or --NHR.sup.2 group; R.sup.2 is an alkyl group having from 1 to about 4 carbon atoms; X.sup.3 is NH.sub.2, NH.sub.2 --SO.sub.2 --, NH.sub.2 --CO--, or NH.sub.2 --Z.sup.8 --O--; Z.sup.8 is an alkyl or cycloalkyl group having from 1 to about 12 carbon atoms; Z.sup.7 is independently be a divalent hydrocarbyl group having from 1 to about 10 carbon atoms, --O--, --CO--, --SO--, --SO.sub.2 --, --S--, --S--S--, --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 --, --N.dbd.N--, --CO--NR.sup.1 --, --NR.sup.1 --CO--, -- CO--NR.sup.1 --NR.sup.1 --CO--, --C.tbd.C--, --C.tbd.C--C.tbd.C--, --CO--S--, --S--CO--, --CR.sup.1 .dbd.N--, --N.dbd.CR.sup.1 --, --CO--O--, --O--CO--, --CR.sup.1 .dbd.CR.sup.1 --CO--, --CO--CR.sup.1 .dbd.CR.sup.1 --, --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, ##STR44## and 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.tbd.N; 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 zero to 2; each Z' is independently a --CO--, --O--CO--, --CO--O--, --CO--NR.sup.1 --, or --NR.sup.1 --CO-- group: each R.sup.1 is independently hydrogen or an aliphatic hydrocarbon group having from 1 to about 4 carbon atoms and each n' independently has a value of zero or one; or any combination of any two or more compounds represented by the aforementioned Formulas XVII and XVIII; and
- (d) components (A) and (B) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.05:1 to about 0.8:1.
- 3. A curable composition of claim 2 wherein
- (a) when component (A) is an epoxy resin represented by Formula I, X is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 4 carbon atoms and when it is a halogen atom, it is bromine
- (b) when component (A) is an epoxy resin represented by Formula II, X is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 4 carbon atoms and when it is a halogen atom, it is bromine; and
- (c) in component (B), when X is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 4 carbon atoms and when it is a halogen atom, it is chlorine or bromine.
- 4. A curable composition of claim 1 wherein
- (a) component (B) is hydroquinone, bisphenol A, 4,4'-dihydroxydiphenylmethane, 4,4'-thiodiphenol, 4,4'-sulfonyldiphenol, 4,4'-dihydroxydiphenyl oxide, 4,4'-dihydroxybenzophenone, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 3,3',5,5'-tetrachlorobisphenol A, 3,3'-dimethoxybisphenol A, 4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-.alpha.,.alpha.'-diethylstilbene, 4,4'-dihydroxy.alpha.-methylstilbene, 4,4'-dihydroxybenzanilide, 4,4'-dihydroxy-2,2'-dimethylazoxybenzene, 4,4'-dihydroxy-.alpha.-cyanostilbene, bis(4-hydroxyphenyl)terephthalate, N,N'-bis(4-hydroxyphenyl)terephthalamide, bis(4'-hydroxybiphenyl)terephthalate, 4,4'-dihydroxyphenylbenzoate, bis(4'-hydroxyphenyl)-1,4-benzenediimine, 4,4"-dihydroxybiphenylbenzoate, 1,4-bis(4'-hydroxyphenyl-1'-carboxamide)benzene, 1,4-bis(4'-hydroxyphenyl-1'-carboxy)benzene, 4,4'-bis(4"-hydroxyphenyl-1"-carboxy)biphenyl, terephthalic acid, 4,4'-benzanilide dicarboxylic acid, 4,4'-phenylbenzoate dicarboxylic acid, 4,4'-stilbenedicarboxylic acid, aniline, 4'-sulfonamido-N-phenylbenzamide, 4'-sulfonamido-N'-phenyl-4-chlorobenzamide, 4-amino-1-phenylbenzoate, 4-amino-N-phenylbenzamide, N-phenyl-4-aminophenyl-1-carboxamide, phenyl-4-aminobenzoate, biphenyl-4-aminobenzoate, 1-phenyl-4'-aminophenylterephthalate or mixtures thereof: and
- (b) components (A) and (B) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.1:1 to about 0.5:1.
- 5. A curable composition of claim 3 wherein
- (a) component (B) is hydroquinone, bisphenol A, 4,4'-dihydroxydiphenylmethane, 4,4'-thiodiphenol, 4,4'-sulfonyldiphenol. 4,4'-dihydroxydiphenyl oxide, 4,4'-dihydroxybenzophenone, 1-bis(4-hydroxyphenyl)-1-phenylethane, 3,3',5,5'-tetrachlorobisphenol A, 3,3'-dimethoxybisphenol A, 4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-.alpha.,.alpha.'-diethylstilbene, 4,4'-dihydroxy-.alpha.-methylstilbene, 4,4'-dihydroxybenzanilide, 4,4'-dihydroxy-2,2'-dimethylazoxybenzene, 4 4'-dihydroxy-.alpha.-cyanostilbene, bis(4-hydroxyphenyl)terephthalate, N,N'-bis(4-hydroxyphenyl)terephthalamide, bis(4'-hydroxybiphenyl)terephthalate, 4'-dihydroxyphenylbenzoate, bis(4'-hydroxyphenyl)-1,4-benzenediimine, 4,4'-dihydroxybiphenylbenzoate, 1,4-bis(4'-hydroxyphenyl-1'-carboxamide)benzene, 4-bis(4'-hydroxyphenyl-1'-carboxy)benzene, 4,4'-bis(4'-hydroxyphenyl-1'-carboxy)biphenyl, terephthalic acid, 4,4'-benzanilide dicarboxylic acid, 4,4'-phenylbenzoate dicarboxylic acid, 4,4'-stilbenedicarboxylic acid, aniline, 4'-sulfonamido-N-phenylbenzamide, 4'-sulfonamido-N'-phenyl-4-chlorobenzamide, 4-amino-1-phenylbenzoate, 4-amino-N-phenylbenzamide, N-phenyl-4-aminophenyl-1-carboxamide, phenyl-4-aminobenzoate, biphenyl-4-aminobenzoate, 1-phenyl-4'-aminophenylterephthalate or mixtures thereof; and
- (b) components (A) and (B) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.1:1 to about 0.5:1.
- 6. A curable composition comprising (1) 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.tbd.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.tbd.C--, --C.tbd.C--C.tbd.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=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 contain one or more heteroatoms selected from N, O or S and is saturated or unsaturated or X.sup.2 is a direct bond; 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.tbd.N; and n' is one; 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.
- 7. A curable composition of claim 6 wherein;
- (a) when component (A-1) is an epoxy resin represented by Formulas I or 11 and when X therein is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 6 carbon atoms and when it is a halogen atom, it is chlorine or bromine;
- (b) component (B) is an epoxy resin represented by the following Formulas V, VI, VII, VIII, IX, X or XI ##STR50## wherein each A is independently a divalent hydrocarbyl group having from 1 to about 12 carbon atoms, --O--, --S--, --S--S--, --SO--, --SO.sub.2 --, or --CO--; each A' is independently a divalent hydrocarbon group having from 1 to about 6 carbon atoms: Q is a single bond, --CH.sub.2 --S--CH.sub.2 --, --(CH.sub.2).sub.n1 --, or ##STR51## each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each R.sup.2 and R.sup.3 is independently hydrogen, a hydrocarbyl or halohydrocarbyl group having from 1 to about 6 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.tbd.N; m has a value from about 1 to about 10: m' has an average value from about 0.01 to about 12: ml has an average value from about 1 to about 12: m.sup.2 has a value from about 1 to about 12: n' has a value of zero or 1; n" has an average value from about zero to about 3 and n.sup.1 has an average value from about 1 to about 10;
- (c) components (A-1) and (A-2) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.05:1 to about 0.8:1;
- (d) component (A) is present in an amount of from about to about 99 percent by weight based on the combined quantities of components (A) and (B); and
- (e) component (B) is present in an amount of from about 99 to about 1 percent by weight based on the combined quantities of components (A) and (B).
- 8. A curable composition of claim 7 wherein;
- (a) when component (A-1) is an epoxy resin represented by Formulas I or Il and when X therein is a hydrocarbyl or hydrocarbyloxy group, it has from 1 to about 4 carbon atoms and when it is a halogen it is bromine:
- (b) component (A-2) is a compound represented by the following Formulas XVII or XVIII ##STR52## wherein X.sup.2 is independently a hydroxyl, carboxylic acid, --SH, or --NHR.sup.2 group: R.sup.2 is an alkyl group having from 1 to about 4 carbon atoms; X.sup.3 is NH.sub.2, NH.sub.2 --SO.sub.2 --, NH.sub.2 --CO--, or NH.sub.2 --Z.sup.8 --O--; Z.sup.8 is an alkyl or cycloalkyl group having from 1 to about 12 carbon atoms; Z.sup.7 independently is a divalent hydrocarbyl group having from 1 to about 10 carbon atoms, --O--, --CO--, --SO--, --SO.sub.2 --, --S--, --S--S--, --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 --, --N.dbd.N--, --CO--NR.sup.1 --, --NR.sup.1 --CO--, --CO--NR.sup.1 --NR.sup.1 --CO--, --C.tbd.C--, --C.tbd.C--C.tbd.C--, --CO--S--, --S--CO--, --CR.sup.1 .dbd.N--, --N.dbd.CR.sup.1 --, --CO--O--, --O--CO--, --CR.sup.1 .dbd.CR.sup.1 --CO--, --CO--CR.sup.1 .dbd.CR.sup.1 --, --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, ##STR53## and 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.tbd.N; Z.sup.2 is a group represented by a cyclic or bicyclic ring system containing from 5 to about 12 carbon atoms is cycloaliphatic, polycycloaliphatic, aromatic or a combination thereof; n is zero to 2; each Z' is independently a --CO--, --O--CO--, --CO--O--, --CO--NR.sup.1 --, or --NR.sup.1 --CO-- group; each R.sup.1 is independently hydrogen or an aliphatic hydrocarbon group having from 1 to about 4 carbon atoms and each n' independently has a value of zero or one; or any combination of any two or more compounds represented by the aforementioned Formulas XVII and XVIII;
- (c) components (A-1) and (A-2) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.05:1 to about 0.9:1;
- (d) component (A) is present in an amount of from about 10 to about 80 percent by weight based on the combined quantities of components (A) and (B); and
- (e) component (B) is present in an amount of from about 90 to about 20 percent by weight based on the combined quantities of components (A) and (B).
- 9. A curable composition of claim 6 wherein
- (a) component (2) is hydroquinone, bisphenol A, 4,4'-dihydroxydiphenylmethane, 4,4'-thiodiphenol, 4,4'-sulfonyldiphenol, 4,4'-dihydroxydiphenyl oxide, 4,4'-dihydroxybenzophenone, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 3,3',5,5'-tetrachlorobisphenol A, 3,3'-dimethoxybisphenol A, 4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-.alpha.,.alpha.'-diethylstilbene, 4,4'-dihydroxy-.alpha.-methylstilbene, 4,4'-dihydroxybenzanilide. 4,4'-dihydroxy-2,2'-dimethylazoxybenzene. 4,4'-dihydroxy-.alpha.-cyanostilbene, bis(4-hydroxyphenyl)terephthalate, N,N'-bis(4-hydroxyphenyl)terephthalamide, bis(4'-hydroxybiphenyl)terephthalate, 4,4'-dihydroxyphenylbenzoate, bis(4'-hydroxyphenyl)-1,4-benzenediimine, 4,4"-dihydroxybiphenylbenzoate, 1,4-bis(4'-hydroxyphenyl-1'-carboxamide)benzene, 1,4-bis(4'-hydroxyphenyl-1'-carboxy)benzene, 4,4'-bis(4"-hydroxyphenyl-1"-carboxy)biphenyl, terephthalic acid, 4,4'-benzanilide dicarboxylic acid, 4,4'-phenylbenzoate dicarboxylic acid. 4,4'-stilbenedicarboxylic acid, aniline, 4'-sulfonamido-N-phenylbenzamide, 4'-sulfonamido-N'-phenyl-4-chlorobenzamide, 4-amino-1-phenylbenzoate, 4-amino-N-phenylbenzamide, N-phenyl-4-aminophenyl-1-carboxamide, phenyl-4-aminobenzoate, biphenyl-4-aminobenzoate, 1-phenyl-4'-aminophenylterephthalate or mixtures thereof:
- (b) components (A-1) and (A-2) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.1:1 to about 0.5:1:
- (c) component (A) is present in an amount of from about 10 to about 50 percent by weight based on the combined quantities of components (A) and (B); and
- (d) component (B) is present in an amount of from about 90 to about 50 percent by weight based on the combined quantities of components (A) and (B).
- 10. A curable composition of claim 8 wherein
- (a) component (2) is hydroquinone, bisphenol A, 4,4'-dihydroxydiphenylmethane, 4,4'-thiodiphenol, 4,4'-sulfonyldiphenol, 4,4'-dihydroxydiphenyl oxide, 4,4'-dihydroxybenzophenone, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 3,3',5,5'-tetrachlorobisphenol A, 3,3'-dimethoxybisphenol A, 4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-.alpha.,.alpha.'-diethylstilbene, 4,4'-dihydroxy-.alpha.-methylstilbene, 4,4'-dihydroxybenzanilide, 4,4'-dihydroxy-2,2'-dimethylazoxybenzene, 4,4'-dihydroxy-.alpha.-cyanostilbene, bis(4-hydroxyphenyl)terephthalate, N,N'-bis(4-hydroxyphenyl)terephthalamide, bis(4'-hydroxybiphenyl)terephthalate, 4,4'-dihydroxyphenylbenzoate, bis(4'-hydroxyphenyl)-1,4-benzenediimine, 4,4"-dihydroxybiphenylbenzoate, 1,4-bis(4'-hydroxyphenyl-1'-carboxamide)benzene, 1,4-bis(4'-hydroxyphenyl-1'-carboxy)benzene, 4,4'-bis(4"-hydroxyphenyl-1"-carboxy)biphenyl, terephthalic acid, 4,4'-benzanilide dicarboxylic acid, 4,4'-phenylbenzoate dicarboxylic acid, 4,4'-stilbenedicarboxylic acid, aniline, 4'-sulfonamido-N-phenylbenzamide, 4'-sulfonamido-N'-phenyl-4-chlorobenzamide, 4-amino-1-phenylbenzoate, 4-amino-N-phenylbenzamide, N-phenyl-4-aminophenyl-1-carboxamide, phenyl-4-aminobenzoate, biphenyl-4-aminobenzoate, 1-phenyl-4'-aminophenylterephthalate or mixtures thereof: and
- (b) components (A-1) and (A-2) are employed in amounts which provide a ratio of active hydrogen atoms per epoxide group of from about 0.1:1 to about 0.5:1.;
- (c) component (A) is present in an amount of from about 10 to about 50 percent by weight based on the combined quantities of components (A) and (B); and
- (d) component (B) is present in an amount of from about 90 to about 50 percent by weight based on the combined quantities of components (A) and (B).
- 11. A curable composition of claim 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 wherein said polyamine containing one or more rodlike mesogenic moieties is represented by the following Formula XIX ##STR54## wherein at least about 80 percent of the --(Z.sup.1 --Z.sup.2 ).sub.n --Z.sup.1 -- linkages and the Z.sup.9 groups are in the para position with respect to each other: each R.sup.1 is independently hydrogen or an aliphatic hydrocarbon group having from 1 to about 12 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.tbd.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.tbd.C--, --C.tbd.C--C.tbd.C--, --N.dbd.N--, --CO--S--, --S--CO--, --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--, --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--, ##STR55## 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.sup.9 is independently a --NHR.sup.1, --O--(CHR.sup.1).sub.n --CHR.sup.1 --NHR.sup.1, --NR.sup.1 --(CHR.sup.1).sub.n --CHR.sup.1 --NHR.sup.1, ##STR56## 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; or the following Formula X ##STR57## wherein Z.sup.3 is ##STR58## 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 contain one or more heteroatoms selected from N, O or S and is saturated or unsaturated or X.sup.1 is a direct bond; each 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 1 to about 12 carbon atoms, a halogen atom, --NO.sub.2, or --C.tbd.N; and n' is one; and Z.sup.9 is as hereinbefore defined.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part of application Ser. No. 07/562,182 filed Aug. 3, 1990, now abandoned which is incorporated herein by reference in its entirety.
US Referenced Citations (11)
Foreign Referenced Citations (3)
Number |
Date |
Country |
58-206579 |
Dec 1983 |
JPX |
61-151800 |
Jun 1986 |
JPX |
60235353 |
May 1987 |
JPX |
Non-Patent Literature Citations (1)
Entry |
"Amine Cured Glass Fibre Composites", Varma et al., Indian Journal of Technology, vol. 21, Jul. 1983, pp. 265-267. |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
562182 |
Aug 1990 |
|