Phenolic epoxy compounds
Disclosed herein are compositions and methods of making phenolic compounds, and resins comprising these phenolic compounds. The compounds include multifunctional epoxies, amino glycidyl derivatives, and multi-functional amines prepared from hydroxymethyl derivatives of phenols and bisphenols. In one embodiment, a compound is of formula I wherein R 1 is H or Z; each R 2 , R 3 , and R 4 , independently, are —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , —O—Z, —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ; and Z is
1. A compound of Formula I:
wherein:
R 1 is H or Z;
R 2 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , —O—Z, —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, or —O—C—(CH 3 ) 3 ;
R 3 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , —O—Z, —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH or —O—C—(CH 3 ) 3 ;
R 4 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , —O—Z, —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH or —O—C—(CH 3 ) 3 ; and
Z is
2. The compound of claim 1 , wherein:
R 1 is H or Z;
R 2 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , or;
R 3 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , or; and
R 4 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 NH 2 ) 2 , or.
3. The compound of claim 1 , wherein:
R 1 is Z;
R 2 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , or —N(CH 2 CH 2 —O—Z) 2 ;
R 3 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , or —N(CH 2 CH 2 —O—Z) 2 ; and
R 4 is —N(Z) 2 , —N(CH 2 —O—Z) 2 , or —N(CH 2 CH 2 —O—Z) 2 .
4. The compound of claim 1 , wherein R 1 is Z, R 2 is —N(Z) 2 , R 3 is —N(Z) 2 , and R 4 is —N(Z) 2 .
5. The compound of claim 1 , wherein R 1 is Z, and each of R 2 is —N(CH 2 —O—Z) 2 , R 3 is —N(CH 2 —O—Z) 2 , and R 4 is —N(CH 2 —O—Z) 2 .
6. The compound of claim 1 , wherein R 1 is Z, and each of R 2 is —N(CH 2 CH 2 —O—Z) 2 , R 3 is —N(CH 2 CH 2 —O—Z) 2 , and R 4 is —N(CH 2 CH 2 —O—Z) 2 .
7. The compound of claim 1 , wherein:
R 1 is H;
R 2 is —N(CH 2 OH) 2 or —N(CH 2 NH 2 );
R 3 is —N(CH 2 OH) 2 or —N(CH 2 NH 2 ); and
R 4 is —N(CH 2 OH) 2 or —N(CH 2 NH 2 ).
8. The compound of claim 1 , wherein R 1 is H, R 2 is —N(CH 2 OH) 2 , R 3 is —N(CH 2 OH) 2 , and R 4 is —N(CH 2 OH) 2 .
9. The compound of claim 1 , wherein R 1 is H, R 2 is —N(CH 2 NH 2 ) 2 , R 3 is —N(CH 2 NH 2 ) 2 , and R 4 is —N(CH 2 NH 2 ) 2 .
10. The compound of claim 1 , wherein R 1 is H, R 2 is —N(CH 2 —O—Z) 2 , R 3 is —N(CH 2 —O—Z) 2 , and R 4 is —N(CH 2 —O—Z) 2 .