Aliphatic polyimides from unsaturated monoanhydride or unsaturated diacid reacted with both monoamine and diamine

Patent metadata

Field	Value
Publication number	US-10619008-B2
Application number	US-201515305817-A
Country	US
Kind code	B2
Filing date	Apr 23, 2015
Priority date	Apr 25, 2014
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

Aliphatic polyimides are synthesized by a reaction of 2 moles of an unsaturated monoanhydride or an unsaturated diacid with both one mole of a diamine and one mole of a monoamine. Imidization of intermediates so formed from those reactions resolve to 6 possible bicyclic imidic structures bridged by monoamidic or saturated hydrocarbon spans, more likely the latter. Bio-derived monomers are particularly useful in the synthesis of the aliphatic polyimides.

First claim

What is claimed is:

1. An aliphatic polyimide, wherein the aliphatic polyimide is selected from the group consisting of:
(a) a mixture of poly-3-N-butylamino-methylene-3′-methylene-((1,1′-decane-1,10-diyl)-bis-(pyrrolidine-2,5-dione)), poly-3,3′-methylene-((1,1′-decane-1,10-diyl)-bis-(pyrrolidine-2,5-dione)), and poly-[3-N-butylamino-methylene-3′-methylene-((1,1′-decane-1,10-diyl)-bis-(pyrrolidine-2,5-dione))]-co-[3,3′-methylene-((1,1′-decane-1,10-diyl)-bis-(pyrrolidine-2,5-dione))];
(b) a mixture of poly-3-N-butylamino-methylene-3′-methylene-((1,1′-ethane-1,2-diyl)-bis-(pyrrolidine-2,5-dione)), poly-3,3′-methylene-((1,1′-ethane-1,2-diyl)-bis-(pyrrolidine-2,5-dione)), and poly-[3-N-butylamino-methylene-3′-methylene-((1,1′-ethane-1,2-diyl)-bis-(pyrrolidine-2,5-dione))]-co-[3,3′-methylene-((1,1′-ethane-1,2-diyl)-bis-(pyrrolidine-2,5-dione))];
(c) a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-butane-1,4-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-butane-1,4-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-((1,1′-butane-1,4-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-butane-1,4-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))];
(d) a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))];
(e) a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-dodecane-1,12-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-dodecane-1,12-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-((1,1′-dodecane-1,12-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-dodecane-1,12-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]; and
(f) a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-ethane-1,2-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-ethane-1,2-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-((1,1′-ethane-1,2-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-ethane-1,2-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))];
(g) a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-hexane-1,6-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-hexane-1,6-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-(1,1′-hexane-1,6-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-hexane-1,6-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))];
(h) all a mixture of poly-4-N-butylamino-yl-4′-yl-((1,1′-nonane-1,9-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-nonane-1,9-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-((1,1′-nonane-1,9-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-nonane-1,9-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))];
(i) a mixture of poly-4-N-butylamino-yl-4′-yl-(1,1′-bis-trimethylene polydimethyl siloxane-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-bis-trimethylene polydimethyl siloxane)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-(1,1′-bis-trimethylene polydimethyl siloxane-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-(1,1′-bis-trimethylene polydimethyl siloxane-bis-(3-methyl-pyrrolidine-2,5-dione))];
(j) a mixture of poly-4-N-butylamino-yl-4′-yl-(1,1′-polyoxypropylene-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-polyoxypropylene)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-butylamino-yl-4′-yl-(1,1′-polyoxypropylene-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-(1,1′-polyoxypropylene-bis-(3-methyl-pyrrolidine-2,5-dione))];
(k) a mixture of poly-4-N-tetradecylamino-yl-4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)), poly-4,4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione)) and poly-[4-N-tetradecylamino-yl-4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]-co-[4,4′-yl-((1,1′-decane-1,10-diyl)-bis-(3-methyl-pyrrolidine-2,5-dione))]; and
(l) combinations thereof.

2. A compound comprising the aliphatic polyimide of claim 1 and one or more functional additives.

3. The compound of claim 2 , wherein the functional additive is selected from the group consisting of adhesion promoters; biocides; anti-fogging agents; anti-static agents; bonding, blowing and foaming agents; dispersants; fillers, fibers, and extenders; flame retardants; smoke suppressants; impact modifiers; initiators; lubricants; micas; pigments, colorants and dyes; plasticizers; processing aids; release agents; silanes, titanates and zirconates; slip and anti-blocking agents; stabilizers; stearates; ultraviolet light absorbers; viscosity regulators; waxes; catalyst deactivators, and combinations of them.

4. An article molded or extruded from the compound of claim 2 .

Assignees

• Polyone Corp

Inventors

• Duan Yannan
• Avakian Roger W

Classifications

• C08G73/106

  containing silicon · CPC title

• C08G73/0273

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C08G73/124

  the unsaturated precursors containing oxygen in the form of ether bonds in the main chain · CPC title

• C08G73/121

  Preparatory processes from unsaturated precursors and polyamines · CPC title

• C08G73/105

  with oxygen only in the diamino moiety · CPC title