Process for making benzoxazines

Patent metadata

Field	Value
Publication number	US-10227313-B2
Application number	US-201815868848-A
Country	US
Kind code	B2
Filing date	Jan 11, 2018
Priority date	Oct 27, 2014
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

A synthesis process for making a benzoxazine compound containing at least one benzoxazine unit from aromatic amine containing at least one primary amino group, at least one phenolic compound with at least one ortho-hydrogen, and alkyl formcel. In one embodiment, the aromatic amine is reacted with alkyl formcel to generate an alkoxymethyl intermediate compound. Subsequently, the intermediate compound is reacted with a phenol to generate the benzoxazine compound. In another embodiment, the benzoxazine compound is formed by reacting aromatic amine with alkyl formcel and phenol in one reaction step. Also disclosed is a method for isolating the alkoxymethyl compound formed by reacting aromatic amine with alkyl formcel. The isolated alkoxymethyl compound is useful as a reactant in a subsequent reaction.

First claim

What is claimed is:

1. A synthesis process comprising reacting an aromatic amine with an alkyl formcel for a sufficient time for the consumption of the aromatic amine so as to form an alkoxymethyl intermediate compound or a mixture of alkoxymethyl intermediate compounds, wherein the aromatic amine is selected from structures represented by Formulas I, II and III:

wherein a=1 or 2; and b=0-50;
in Formula III, X and Y are linking groups that are independently selected from a direct bond, O, S, SO2, P=O, (Ph)P=O, OP(═O)O, C=O, substituted or unsubstituted alkylene, substituted or unsubstituted alkylidene, oxoalkylene, substituted or unsubstituted cycloaliphatic or aromatic group, where Ph is phenyl; Z is H or NH 2 ; R 5 , R 6 , R 7 and R 8 are same or different and are independently selected from hydrogen, halogen, substituted or unsubstituted alkyl, alkenyl, alkynyl or alkoxy of C1 to C20 carbon atoms, carboxyl, cyano, aryl, aralkyl or aryloxy group, and optionally, R 5 and R 6 taken together and/or R 7 and R 8 taken together being a part of a saturated or unsaturated fused carbocyclic ring, which optionally contains O, N or S atoms in the ring;
in Formula II, when a=1, X is as define for Formula III, and when a=2, X is one of the following:

and the alkoxymethyl intermediate compound is represented by the following Formula VII:

where x=0-10 and y=1-10; R′=H or R; R=C1-C12 straight chain, branched chain, acyclic or cyclic, saturated or unsaturated group; and Ar is the aromatic residue part of the amine of Formulas I, II or III.

2. The synthesis process of claim 1 , wherein the alkyl formcel is methyl formcel.

Assignees

• Cytec Ind Inc

Inventors

• Gupta Ram B
• Gupta Manav

Classifications

• C07C317/34

  having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring · CPC title

• C07C315/04

  by reactions not involving the formation of sulfone or sulfoxide groups · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D265/16 Primary

  with only hydrogen or carbon atoms directly attached in positions 2 and 4 · CPC title

• C07C317/36

  with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms · CPC title