Multi-functional phenolic resins

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Quick Facts

Patent No.: US 9,868,683
App. No.: 14/898,420
Granted: Jan 16, 2018
Kind: B2

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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.

Claims (18)

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 .

Assignments (3)

SECURITY INTEREST Recorded Jan 29, 2019

From: EMPIRE TECHNOLOGY DEVELOPMENT LLC

To: CRESTLINE DIRECT FINANCE, L.P.

Reel/Frame 048373/0217 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2015

From: ADAM, GEORGIUS ABIDAL

To: ADAMS INVENTION CONSULTING PTY LTD

Reel/Frame 037286/0911 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2015

From: ADAMS INVENTION CONSULTING PTY LTD

To: EMPIRE TECHNOLOGY DEVELOPMENT LLC

Reel/Frame 037286/0925 →