Oxyalkylene-substituted m-amidoaniline intermediate

Details Oxyalkylene-substituted m-amidoaniline intermediate Oxyalkylene-substituted m-amidoaniline intermediate

1999-03-05

2000-05-30

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

534729, 534855, C07D 4104

Patent

active

060692766

ABSTRACT:
This invention relates to very specific oxyalkylene-substituted m-amidoaniline compounds as intermediates for the production of poly(oxyalkylene)-substituted diazo (or other type) colorants. Such an inventive intermediate compound is produced in a single step by reacting an oxyalkylene oxide or alkoxy oxyalkylester having at least three carbon atoms (branched or unbranched), glycidol, or a glycidyl group directly with m-acetoamidoaniline (as a preferred example) at a relatively low temperature. Propylene oxide is the preferred compound. The propylene oxide selectively reacts with the amine group on the base compound without propoxylating the amido group. Such a specific method thus does not require extra time- and cost-consuming steps of protecting the amido nitrogen from attack. After production, this intermediate may be reacted with, for example, a diazotized aromatic amine to ultimately form a diazo colorant. The resultant oxypropylene groups may subsequently be reacted with other compounds, such as anhydrides, isocyanates, esters, and the like, to produce any number of different colorants.

REFERENCES:
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patent: 2155755 (1939-04-01), Felix et al.
patent: 2286795 (1942-06-01), Dickey et al.
patent: 2436100 (1948-02-01), Dickey
patent: 2771466 (1956-11-01), Towne et al.
patent: 4113721 (1978-09-01), Hauser et al.
patent: 4871371 (1989-10-01), Harris

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