IP Library › Patent Application 15584363
Patent Application
App. No. 15/584,363

PHENOLIC EPOXY COMPOUNDS

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Patent No.
US None
App. No.
15/584,363
Abstract

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.

Claims (57)

1 . A compound of Formula II:

wherein:

X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —;

R 1 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 2 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 3 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 4 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 5 is OH or —O—Z;

R 6 is OH or —O—Z;

Z is

and

Y is Cl, Br, F, or I.

2 . The compound of claim 1 , wherein X is —CH 2 —, —C(CH 3 ) 2 —, or —C(Cl) 2 —.

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

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

5 . The compound of claim 1 , wherein R 3 is OH, —O—Z, —N(Z) 2 , NH 2 , —N(CH 2 OH) 2 , or —O—C—(CH 3 ) 3 .

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

7 . The compound of claim 1 , wherein:

X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —;

R 1 is OH, —O—Z, —N(Z) 2 , NH 2 , —N(CH 2 OH) 2 , or —O—C—(CH 3 ) 3 ;

R 2 is OH, —O—Z, —N(Z) 2 , NH 2 , —N(CH 2 OH) 2 , or —O—C—(CH 3 ) 3 ;

R 3 is OH, —O—Z, —N(Z) 2 , NH 2 , —N(CH 2 OH) 2 , or —O—C—(CH 3 ) 3 ;

R 4 is OH, —O—Z, —N(Z) 2 , NH 2 , —N(CH 2 OH) 2 , or —O—C—(CH 3 ) 3 ;

R 5 is OH or —O—Z; and

R 6 is OH or —O—Z.

8 . The compound of claim 7 , wherein R 1 is OH, R 2 is OH, R 3 is OH, R 4 is OH, R 5 is OH, R 6 is OH, and X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —.

9 . The compound of claim 8 , wherein R 1 is OH, R 2 is OH, R 3 is OH, R 4 is OH, R 5 is OH, R 6 is OH, and X is —CH 2 —.

10 . The compound of claim 8 , wherein R 1 is OH, R 2 is OH, R 3 is OH, R 4 is OH, R 5 is OH, R 6 is OH, and X is —C(CH 3 ) 2 —.

11 . The compound of claim 7 , wherein R 1 is O—Z, R 2 is —O—Z, R 3 is —O—Z, R 4 is —O—Z, R 5 is —O—Z, R 6 is —O—Z, and X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —.

12 . The compound of claim 11 , wherein R 1 is —O—Z, R 2 is —O—Z, R 3 is —O—Z, R 4 is —O—Z, R 5 is —O—Z, R 6 is —O—Z, and X is —CH 2 —.

13 . The compound of claim 11 , wherein R 1 is —O—Z, R 2 is —O—Z, R 3 is —O—Z, R 4 is —O—Z, R 5 is —O—Z, R 6 is —O—Z, and X is —C(CH 3 ) 2 —.

14 . The compound of claim 7 , wherein R 1 is NH 2 , R 2 is NH 2 , R 3 is NH 2 , R 4 is NH 2 , R 5 is OH, R 6 is OH, and X is —CH 2 —.

15 . The compound of claim 7 , wherein R 1 is —N(CH 2 OH) 2 , R 2 is —N(CH 2 OH) 2 , R 3 is —N(CH 2 OH) 2 , R 4 is —N(CH 2 OH) 2 , R 5 is OH, R 6 is OH, and X is —CH 2 —.

16 . The compound of claim 7 , wherein R 1 is —N(Z) 2 , R 2 is —N(Z) 2 , R 3 is —N(Z) 2 , R 4 is —N(Z) 2 , R 5 is OZ, R 6 is OZ, and X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —.

17 . The compound of claim 16 , wherein R 1 is —N(Z) 2 , R 2 is —N(Z) 2 , R 3 is —N(Z) 2 , R 4 is —N(Z) 2 , R 5 is OZ, R 6 is OZ, and X is —CH 2 —.

18 . The compound of claim 16 , wherein R 1 is —N(Z) 2 , R 2 is —N(Z) 2 , R 3 is —N(Z) 2 , R 4 is —N(Z) 2 , R 5 is OZ, R 6 is OZ, and X is —C(Cl) 2 —.

19 . The compound of claim 7 , wherein R 1 is —O—C—(CH 3 ) 3 , R 2 is —O—C—(CH 3 ) 3 , R 3 is —O—C—(CH 3 ) 3 , R 4 is —O—C—(CH 3 ) 3 , R 5 is OH, R 6 is OH, and X is —C(CH 3 ) 2 —.

20 . A method of preparing a compound of Formula II:

wherein:

X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, or —C(F) 2 —;

R 1 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 2 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 3 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 4 is OH, —O—Z, —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 , —N(CH 2 CH 2 OH) 2 , NH 2 , —CH 2 —O—Z, —CH 2 CH 2 —O—Z, —CH 2 OH, —CH 2 NH 2 , —CH 2 —Y, —O—C—(CH 3 ) 3 , or —O-(alkylene)-CH 3 ;

R 5 is OH or —O—Z;

R 6 is OH or —O—Z;

Z is

and

Y is Cl, Br, F, or I,

the method comprising:

contacting a phenolic compound with a formaldehyde or a paraformaldehyde to form a hydroxymethyl compound; and

contacting the hydroxymethyl compound with an epihalohydrin compound, a diethanolamine compound, or an ammonia to form the compound.

21 . The method of claim 20 , wherein the phenolic compound is phenol, bisphenol A, bisphenol F, bisphenol S, bisphenol sulphone, bisphenol sulfoxide, bisphenol chloral, bisphenolvinylidene dichloride, or bisphenol methylenedifluoride.

22 . The method of claim 20 , wherein the hydroxymethyl compound is trihydroxymethyl phenol, tetrahydroxymethyl bisphenol A, tetrahydroxymethyl bisphenol F, tetrahydroxymethyl bisphenol S, tetrahydroxymethyl bisphenol sulphone, tetrahydroxymethyl bisphenol sulfoxide, tetrahydroxymethyl bisphenol chloral, tetrahydroxymethyl bisphenolvinylidene dichloride, or tetrahydroxymethyl bisphenol methylenedifluoride.

23 . The method of claim 20 , wherein contacting the phenolic compound with the formaldehyde or the paraformaldehyde comprises contacting about 1 mole of the phenolic compound with about 3 moles to about 5 moles of the formaldehyde or the paraformaldehyde in presence of a basic catalyst.

24 . The method of claim 20 , wherein contacting the hydroxymethyl compound with the epihalohydrin compound comprises contacting about 1 mole of the hydroxymethyl compound with about 2 moles to about 10 moles of the epihalohydrin compound in presence of a reaction catalyst.

25 . The method of claim 24 , wherein contacting the hydroxymethyl compound with the epihalohydrin compound in the presence of the reaction catalyst comprises adding an organic solvent.

Assignments (3)
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.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2017
From: ADAM, GEORGIUS ABIDAL
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 042212/0287 →