Multi-functional phenolic resins

Patent metadata

Field	Value
Publication number	US-9868683-B2
Application number	US-201314898420-A
Country	US
Kind code	B2
Filing date	Jun 13, 2013
Priority date	Jun 13, 2013
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

Disclosed herein are compositions and methods of making phenolic compounds and phenolic resins. The resins include multifunctional epoxies, amino glycidyl derivatives, alkanoate derivatives, alkyl ether derivatives, and multi-functional amines prepared from hydroxymethyl derivatives of novolac resin.

First claim

What is claimed is:

1. A compound of formula I:

wherein:
a is an integer from 1 to 10;
R 1 is H, Z, —C(═O)—CH═CH 2 , —(CH 2 —CH 2 —O) n H, —(CH 2 —CH 2 —CH 2 —O) n H, or —(CH 2 —CH 2 —O) n —(CH 2 —CH(CH 3 )—O) n H, where each n is, independently, an integer from 1 to 18;
each R 2 is, independently, H, Z, —C(═O)—CH═CH 2 , —(CH 2 —CH 2 —O) p H, —(CH 2 —CH 2 —CH 2 —O) p H, or —(CH 2 —CH 2 —O) p —(CH 2 —CH(CH 3 )—O) p H, where each p is, independently, an integer from 1 to 18;
R 3 is H, Z, —C(═O)—CH═CH 2 , —(CH 2 —CH 2 —O) q H, —(CH 2 —CH 2 —CH 2 —O) q H, or —(CH 2 —CH 2 —O) q —(CH 2 —CH(CH 3 )—O) q H, where each q is, independently, an integer from 1 to 18;
R 4 is —NH 2 , —O—Z, —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 NH 2 ) 2 , —N(CH 2 CH 2 OH) 2 , —CH 2 —O—Z, —CH 2 —OH, —CH 2 —NH 2 , —N(CH 3 ) 2 , —O-(alkylene)- CH 3 , —CH 2 —Y, —NCO, —O—C(═O)—(CH 2 ) r —CH 3 , —NH—Z, —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —CH 2 CH 2 —O—Z, —CH 2 CH 2 OH, —O—C(═O)—CH═CH 2 , —N(CH 2 —CH 2 —NH 2 ) 2 , —(CH 2 —CH 2 —O) r H, —(CH 2 —CH 2 —CH 2 —O) r H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , where each r is, independently, an integer from 1 to 18;
R 5 is —OH, —NH 2 , —O—Z, —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 NH 2 ) 2 , —N(CH 2 CH 2 OH) 2 , —CH 2 —O—Z, —CH 2 —OH, —CH 2 —NH 2 , —N(CH 3 ) 2 , —O-(alkylene)- CH 3 , —CH 2 —Y, —NCO, —O—C(═O)—(CH 2 ) t —CH 3 , —NH—Z, —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —CH 2 CH 2 —O—Z, —CH 2 CH 2 OH, —O—C(═O)—CH═CH 2 , —N(CH 2 —CH 2 —NH 2 ) 2 , —(CH 2 —CH 2 —O) t H, —(CH 2 —CH 2 —CH 2 —O) t H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , where each t is, independently, an integer from 1 to 18;
R 6 is —OH, —NH 2 , —O—Z, —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 NH 2 ) 2 , —N(CH 2 CH 2 OH) 2 , —CH 2 —O—Z, —CH 2 —OH, —CH 2 —NH 2 , —N(CH 3 ) 2 , —O-(alkylene)- CH 3 , —CH 2 —Y, —NCO, —O—C(═O)—(CH 2 ) v —CH 3 , —NH—Z, —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —CH 2 CH 2 —O—Z, —CH 2 CH 2 OH, —O—C(═O)—CH═CH 2 , —N(CH 2 —CH 2 —NH 2 ) 2 , —(CH 2 —CH 2 —O) v H, —(CH 2 —CH 2 —CH 2 —O) v H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , where each v is, independently, an integer from 1 to 18;
each R 7 is, independently, —OH, —NH 2 , —O—Z, —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 NH 2 ) 2 , —N(CH 2 CH 2 OH) 2 , —CH 2 —O—Z, —CH 2 —NH 2 , —N(CH 3 ) 2 , —O-(alkylene)-CH 3 , —CH 2 —Y, —NCO, —O—C(═O)—(CH 2 ) w —CH 3 , —NH—Z, —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —CH 2 CH 2 —O—Z, —CH 2 CH 2 OH, —O—C(═O)—CH═CH 2 , —N(CH 2 —CH 2 —NH 2 ) 2 , —(CH 2 —CH 2 —O) w H, —(CH 2 —CH 2 —CH 2 —O) w H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , where each w is, independently, an integer from 1 to 18;
R 8 is —OH, —NH 2 , —O—Z, —N(Z) 2 , —N(CH 2 —O—Z) 2 , —N(CH 2 OH) 2 , —N(CH 2 CH 2 —O—Z) 2 , —N(CH 2 NH 2 ) 2 , —N(CH 2 CH 2 OH) 2 , —CH 2 —O—Z, —CH 2 —OH, —CH 2 —NH 2 , —N(CH 3 ) 2 , —O-(alkylene)- CH 3 , —CH 2 —Y, —NCO, —O—C(═O)—(CH 2 ) x —CH 3 , —NH—Z, —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —CH 2 CH 2 —O—Z, —CH 2 CH 2 OH, —O—C(═O)—CH═CH 2 , —N(CH 2 —CH 2 —NH 2 ) 2 , —(CH 2 —CH 2 —O) x H, —(CH 2 —CH 2 —CH 2 —O) x H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , where each x is, independently an integer from 1 to 18;
Z is

and
Y is Cl, Br, F, or I.

2. The compound of claim 1 , wherein R 1 , R 2 , and R 3 are each independently H.

3. The compound of claim 1 , wherein R 4 is —NH 2 , —N(CH 3 ) 2 , —O—C(═O)—CH═CH 2 , —NCO, —O—C(═O)—(CH 2 ) r —CH 3 , —NH—C(═O)CH═CH 2 , —O—Z, —O—(CH 2 ) 7 —CH 3 , —NH—Z, or —N(CH 2 CH 2 OH) 2 .

4. The compound of claim 1 , wherein R 5 , R 6 , R 7 , and R 8 are each independently —NH 2 , —N(CH 3 ) 2 , —O—C(═O)—CH═CH 2 , —NCO, —O—C(═O)—(CH 2 ) y —CH 3 , C(═O)CH═CH 2 , —O—Z, —O—(CH 2 ) 7 —CH 3 , —NH—Z, or —N(CH 2 CH 2 OH) 2 .

5. The compound of claim 1 , wherein R 1 is —H, each R 2 is —H, R 3 is —H, R 4 is —NH—C(═O)CH═CH 2 , R 5 is —NH—C(═O)CH═CH 2 , R 6 is —NH—C(═O)CH═CH 2 , each R 7 is —NH—C(═O)CH═CH 2 , and R 8 is —NH—C(═O)CH═CH 2 .

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal

Classifications

• C07C37/20

  using aldehydes or ketones · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C08G8/08 Primary

  of formaldehyde, e.g. of formaldehyde formed in situ · CPC title

• C08G8/28

  Chemically modified polycondensates · CPC title