Multi-functional phenolic resins

Inventor: Georgius Abidal Adam (Edensor Park, AU)

Assignee: Empire Technology Development LLC

C07C39/15 C07C37/20 C07C41/01 C07C43/1783 C07C67/00 C07C69/54 C07C213/02 C07C215/50 C07C231/02 C07C233/20 C07C263/10 C07C265/08 C07D301/28 C07D303/30 C07D303/36 C08G8/08 C08G8/28 C08L61/14

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Quick Facts

Patent No.: US 9,868,683
App. No.: 14/898,420
Filed: Dec 14, 2015
Granted: Jan 16, 2018
Kind: B2
Examiner: OH, TAYLOR V
Art Unit: 1625
USPC: 549/517

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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 (5)

RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019, AT REEL/FRAME 048373/0217 Recorded Jun 22, 2026

From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT

To: EMPIRE TECHNOLOGY DEVELOPMENT LLC

Reel/Frame 075799/0053 →

RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025

From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT

To: EMPIRE TECHNOLOGY DEVELOPMENT LLC

Reel/Frame 072936/0464 →

SECURITY INTEREST Recorded Jan 29, 2019

From: EMPIRE TECHNOLOGY DEVELOPMENT LLC

To: CRESTLINE DIRECT FINANCE, L.P.