US 10,619,008 B2Granted

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

AssigneePolyOne Corporation

InventorsYannan Duan, Roger W. Avakian

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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.

Claims4

Dependent claims

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.

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/305,817Filed 23 Apr 2015 · us provisional application
Priority: 25 Apr 2014
Published: US 2017/0044319 A116 Feb 2017
Granted: 14 Apr 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C08G 73/10
Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule: polyimides; Polyester-imides;…
C08G 73/0273
Polyamines: polyamines containing heterocyclic moieties in the main chain
C08G 73/105
Polyimides containing oxygen in the form of ether bonds in the main chain: with oxygen only in the diamino moiety
C08G 73/106
Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain: containing silicon

Family

Application61/984,636Us provisional application · filed 25 Apr 2014
US 2017/0044319 A1Pre-grant publication · published 16 Feb 2017
US 10,619,008 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

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.

11 more elements

Facts

Application

15/305,817Filed 23 Apr 2015 · us provisional application

Priority

25 Apr 2014

Published

US 2017/0044319 A116 Feb 2017

Granted

14 Apr 2020

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C08G 73/10
Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule: polyimides; Polyester-imides;…
C08G 73/0273
Polyamines: polyamines containing heterocyclic moieties in the main chain
C08G 73/105
Polyimides containing oxygen in the form of ether bonds in the main chain: with oxygen only in the diamino moiety
C08G 73/106
Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain: containing silicon