US2017233357A1PendingUtilityA1
Phenolic epoxy compounds
Est. expiryFeb 15, 2033(~6.6 yrs left)· nominal 20-yr term from priority
Inventors:Georgius Abidal Adam
C08G 59/3218C08G 59/08C07D 303/36C07D 303/27C07D 303/23C07C 215/50C07C 43/1785C07C 39/12C07D 303/30C07D 301/28C07C 37/20C07C 213/02C07C 41/01
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Claims
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
exact text as granted — not AI-modifiedWhat is claimed is:
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.Join the waitlist — get patent alerts
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