Aromatic hydroxyl-containing compounds containing organosiloxane moieties, epoxy compounds and cured products thereof
AssigneeThe Dow Chemical Company
InventorsZeng K. Liao, Chun S. Wang
Life of this patent
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Abstract
Compounds are prepared which contain both an organosiloxane moiety and either a phenolic hydroxyl group or an epoxide group. Also disclosed are curable and cured compositions.
Claims25
An advanced resin prepared by reacting (1) at least one compound containing an average of more than one aromatic hydroxyl group per molecule;
- and (2) at least one compound containing an average of more then one vicinal epoxy group per molecule;
- with the proviso that at least one compound of components (2) or (2) is a compound which contains at least one organosiloxane moiety and which compound containing at least one organosiloxane moiety is represented by the following general formulas I or II ##STR13## wherein Ar is any divalent or multivalent aromatic moiety or divalent or multivalent inert substituted aromatic moiety;
- each R is independently hydrogen or an alkyl group having from 1 to about 3 carbon atoms;
- each X" is independently a divalent aliphatic or a divalent cycloaliphatic group or a divalent alkoxy or or a divalent cycloalkoxy group having from 2 to about 12 carbon atoms;
- Z is an n.sup.2 -valent entity containing at least one organosiloxane moiety;
- n.sup.1 has a value from 1 to about 3;
- and n.sup.2 has a value from 1 to about 200;
- with the proviso that (a) when n.sup.2 has a value of 1, n.sup.1 has a value greater than 1;
- and (b) the group(s) ##STR14## is (are) attached to a silicon atom.
A curable composition comprising (A) at least one compound having an average of more than one vicinal epoxy group and at least one organosiloxane moiety per molecule;
- and (B) at least one curing agent for component (A), which during agent is free of aromatic hydroxyl groups;
- wherein component (A) is an advanced resin which has an average of more than one glycidyl group per molecule prepared by reacting (1) at least one compound containing an average of more than one aromatic hydroxyl group per molecule;
- and (2) at least one compound containing an average of more than one vicinal epoxy group per molecule;
- with the proviso that at least one compound of components (1) or (2) is a compound which contains at least one organosiloxane moiety and which compound containing at least one organosiloxane moiety is represented by the following general formulas I or II
- Z--(X"--Ar--(OH).sub.n1).sub.n2 Formula I
- wherein Ar is any divalent or multivalent aromatic moiety or divalent or multivalent inert substituted aromatic moiety;
- each R is independently hydrogen or an alkyl group having from 1 to about 3 carbon ##STR18## atoms;
- each X" is independently a divalent aliphatic or a divalent cycloaliphatic group or a divalent alkoxy or or a divalent cycloalkoxy group having from 2 to about 12 carbon atoms;
- Z is an n.sup.2 -valent entity containing at least one organosiloxane moiety;
- n.sup.1 has a value from 1 to about 3;
- and n.sup.2 has a value from 1 to about 200;
- with the proviso that when n.sup.2 has a value of 1, n.sup.1 has a value greater than 1.
A curable composition comprising (A) at least one compound having an average of more than one vicinal group per molecule and (B) at least one compound having an average of more than one aromatic hydroxyl group per molecule;
- with the proviso that at least one compound of components (A) and (B) is a compound which contains at least one organosiloxane moiety wherein component (A) contains a compound having an average or more than one vicinal epoxy and at least one organosiloxane moiety per molecule, said compound being represented by the following general formula II ##STR24## wherein Ar is any divalent or multivalent aromatic moiety or monovalent or multivalent inert substituted aromatic moiety;
- each R is independently hydrogen or an alkyl group having from 1 to 3 carbon atoms;
- each X" is independently a divalent aliphatic or a divalent cycloaliphatic group or a divalent alkoxy or a divalent cycloalkoxy group having from 2 to about 12 carbon atoms;
- Z is an n.sup.2 -valent entity containing at least one organosiloxane moiety;
- n.sup.1 has a value from 1 to about 3;
- and n.sup.2 has a value from 1 to about 200;
- with the proviso that (a) when n.sup.2 has a value of 1, n.sup.1 has a value greater than 1;
- and (b) the group(s) ##STR25## is (are) attached to a silicon atom.
A curable composition comprising (A) at least one compound having an average of more than one vicinal epoxy group per molecule and (B) at least one compound having an average of more than one aromatic hydroxyl group per molecule, said compound being represented by the following general formulas X, XI, XII, or XIII ##STR37## wherein each R' is independently a hydrocarbyl group having from 1 to about 20 carbon atoms;
- each Y is a hydrocarbyl group having from 2 to about 20 carbon atoms or an entity represented by the following formulas XXII, XXIII, XXIV, XXV, XXVI, XXVII, or XXVIII with the proviso that at least an average of more than one Y is other than a hydrocarbyl group:
- ##STR38## wherein each A is independently a divalent hydrocarbyl group having from 1 to about 20 carbon atoms, --O--, --S--, --S--S--, --SO--, --SO.sub.2 --, or --CO--;
- each A' is independently a divalent hydrocarbyl group having from 1 to about 20 carbon atoms;
- each Q is independently hydrogen or an alkyl group having from 1 to about 10 carbon atoms;
- each Q' is independently a tetravalent hydrocarbyl group having from 1 to about 20 carbon atoms;
- each R is independently hydrogen or an alkyl group having from 1 to about 3 carbon atoms;
- each X is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 12 carbon atoms, a halogen atom, or a hydroxyl group;
- each X' is independently hydrogen or a monovalent aliphatic or a monovalent cycloaliphatic group;
- each X" is independently a divalent aliphatic or a divalent cycloaliphatic group or a divalent alkoxy or a divalent cycloalkoxy group having from 2 to about 12 carbon atoms;
- each Z' is hydrogen;
- each m independently has an average value from about 0.01 to about 8;
- each m' independently has an average value from about zero to about 8;
- each n independently has a value of zero or 1;
- each n' independently has an average value from about 0.001 to about 20;
- each n.sup.1 independently has a value from 1 to about 3;
- each p independently has a value from zero to about 10;
- each p' independently has an average value from zero to about 8;
- and each s, t and u independently has a value from 1 to about 3 with the proviso that the sum of s, t and u satisfies the valency of the ring;
- each x independently has a value from zero to about 500;
- each x' independently has a value from 2 to about 500;
- each x" independently has a value from 3 to about 50;
- and the sum of x and x' is from about 2 to about 1000.
Dependencies are inferred from the claim text.