US 9,868,683 B2Granted

Multi-functional phenolic resins

AssigneeEmpire Technology Development LLC

InventorGeorgius Abidal Adam

Life of this patent

Estimating the term…

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.

Claims5

Dependent claims

A compound of formula I:

wherein:
a is an integer from 1 to 10;
R1 is H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)nH, —(CH2—CH2—CH2—O)nH, or —(CH2—CH2—O)n—(CH2—CH(CH3)—O)nH, where each n is, independently, an integer from 1 to 18;
each R2 is, independently, H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)pH, —(CH2—CH2—CH2—O)pH, or —(CH2—CH2—O)p—(CH2—CH(CH3)—O)pH, where each p is, independently, an integer from 1 to 18;
R3 is H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)qH, —(CH2—CH2—CH2—O)qH, or —(CH2—CH2—O)q—(CH2—CH(CH3)—O)qH, where each q is, independently, an integer from 1 to 18;
R4 is —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)r—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)rH, —(CH2—CH2—CH2—O)rH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each r is, independently, an integer from 1 to 18;
R5 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)t—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)tH, —(CH2—CH2—CH2—O)tH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each t is, independently, an integer from 1 to 18;
R6 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)v—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)vH, —(CH2—CH2—CH2—O)vH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each v is, independently, an integer from 1 to 18;
each R7 is, independently, —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—NH2, —N(CH3)2, —O-(alkylene)-CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)w—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)wH, —(CH2—CH2—CH2—O)wH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each w is, independently, an integer from 1 to 18;
R8 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)x—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)xH, —(CH2—CH2—CH2—O)xH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each x is, independently an integer from 1 to 18;
Z is
and
Y is Cl, Br, F, or I.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/898,420Filed 13 Jun 2013
Published: US 2016/0137570 A119 May 2016
Granted: 16 Jan 2018
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07C 39/15
Polycyclic with no unsaturation outside the aromatic rings: with all hydroxy groups on non-condensed rings , e.g. phenylphenol
C07C 37/20
By reactions increasing the number of carbon atoms: using aldehydes or ketones
C07C 41/01
Preparation of ethers; Preparation of compounds having [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups or[IMAGE…:…
C07C 43/1783
Containing six-membered aromatic rings: with hydroxy or -O-metal groups bound to the aromatic rings

Family

US 2016/0137570 A1Pre-grant publication · published 19 May 2016
US 9,868,683 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of formula I:

wherein:
a is an integer from 1 to 10;
R1 is H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)nH, —(CH2—CH2—CH2—O)nH, or —(CH2—CH2—O)n—(CH2—CH(CH3)—O)nH, where each n is, independently, an integer from 1 to 18;
each R2 is, independently, H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)pH, —(CH2—CH2—CH2—O)pH, or —(CH2—CH2—O)p—(CH2—CH(CH3)—O)pH, where each p is, independently, an integer from 1 to 18;
R3 is H, Z, —C(═O)—CH═CH2, —(CH2—CH2—O)qH, —(CH2—CH2—CH2—O)qH, or —(CH2—CH2—O)q—(CH2—CH(CH3)—O)qH, where each q is, independently, an integer from 1 to 18;
R4 is —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)r—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)rH, —(CH2—CH2—CH2—O)rH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each r is, independently, an integer from 1 to 18;
R5 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)t—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)tH, —(CH2—CH2—CH2—O)tH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each t is, independently, an integer from 1 to 18;
R6 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)v—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)vH, —(CH2—CH2—CH2—O)vH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each v is, independently, an integer from 1 to 18;
each R7 is, independently, —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—NH2, —N(CH3)2, —O-(alkylene)-CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)w—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)wH, —(CH2—CH2—CH2—O)wH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each w is, independently, an integer from 1 to 18;
R8 is —OH, —NH2, —O—Z, —N(Z)2, —N(CH2—O—Z)2, —N(CH2OH)2, —N(CH2CH2—O—Z)2, —N(CH2NH2)2, —N(CH2CH2OH)2, —CH2—O—Z, —CH2—OH, —CH2—NH2, —N(CH3)2, —O-(alkylene)- CH3, —CH2—Y, —NCO, —O—C(═O)—(CH2)x—CH3, —NH—Z, —N[CH2O—C(═O)—CH═CH2]2, —NH—C(═O)CH═CH2, —CH2CH2—O—Z, —CH2CH2OH, —O—C(═O)—CH═CH2, —N(CH2—CH2—NH2)2, —(CH2—CH2—O)xH, —(CH2—CH2—CH2—O)xH, —N[CH2—CH2—O—C(═O)—CH═CH2]2, or —N[CH2—CH2—NH—C(═O)—CH═CH2]2, where each x is, independently an integer from 1 to 18;
Z is
and
Y is Cl, Br, F, or I.

10 more elements

Facts

Application

14/898,420Filed 13 Jun 2013

Published

US 2016/0137570 A119 May 2016

Granted

16 Jan 2018

Term ends

Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07C 39/15
Polycyclic with no unsaturation outside the aromatic rings: with all hydroxy groups on non-condensed rings , e.g. phenylphenol
C07C 37/20
By reactions increasing the number of carbon atoms: using aldehydes or ketones
C07C 41/01
Preparation of ethers; Preparation of compounds having [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups or[IMAGE…:…
C07C 43/1783
Containing six-membered aromatic rings: with hydroxy or -O-metal groups bound to the aromatic rings