ALIPHATIC POLYIMIDES FROM A 1:1 MOLAR RATIO OF DIAMINE AND UNSATURATED MONOANHYDRIDE OR UNSATURATED DIACID
Aliphatic polyimides are synthesized by a 1:1 molar ratio reaction of an unsaturated monoanhydride or an unsaturated diacid with a diamine. Bio-derived monomers are particularly useful in the synthesis of the aliphatic polyimides.
1 . An aliphatic polyimide selected from the group consisting of:
and combinations thereof, wherein in is greater than about 20, wherein n is greater than about 20, and wherein R is H for maleic anhydride and CH 3 for citraconic anhydride, and X═(CH 2 ) z ,
wherein x is 1 to 1000 wherein y is 1 to 100, and wherein z is 2 to 12.
2 . The aliphatic polyimide of claim 1 , wherein the aliphatic polyimide selected from the group consisting of
(a) poly-(3-methylene-2,5-dioxo-1-pyrrolidine-N-ethylene amino);
(b) poly-3-(2,5-dioxo-1-pyrrolidine-N-decamethylene amino);
poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-bis-trimethylene poly-dimethyl siloxane amino);
(c) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-dodecamethylene amino);
(d) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-polyoxypropylene amino);
(e) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-decamethylene amino);
(f) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-ethylene amino);
(g) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-hexamethylene amino);
(h) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-nonamethylene amino);
(i) poly-3-(4-methyl-2,5-dioxo-1-pyrrolidine-N-tetramethylene amino); and
(j) combinations thereof.
3 . The aliphatic polyimide of claim 1 , wherein the aliphatic polyimide is represented by the formula
wherein the polyimide is formed by the reaction of a diamine to a monoanhydride at a 1:1 molar ratio, giving a ring-opened amic acid, followed by self polymerization of the ring-opened amic acid at a temperature of about 220° C. to form the aliphatic polyimide, wherein the monohydride is citraconic anhydride or maleic anhydride.
4 . The aliphatic polyimide of claim 1 , wherein m is greater than about 150, wherein x is about 5 to about 25, wherein y is 2 to about 35, wherein the glass transition temperature ranges from −30° C. to 160′C.
5 . The aliphatic polyimide of claim 1 , wherein the aliphatic polyimide is represented by the formula
wherein the polyimide is formed by the reaction of a diamine to a monoanhydride at a 1:1 molar ratio, giving a ring-opened amic acid, followed by self polymerization of the ring-opened amic acid at a temperature of about 220′C to form the aliphatic polyimide, wherein the monoanhydride is itaconic anhydride.
6 . The aliphatic polyimide of claim 1 , wherein n is greater than about 150, wherein x is about 5 to about 25, wherein y is about 2 to about 35, and wherein the glass transition temperature is about 160° C.
7 . The aliphatic polyimide of claim 1 , wherein the aliphatic polyimide is represented by the formula
wherein the polyimide is formed by the reaction of a diamine to a diacid at a 1:1 molar ratio, giving a ring-opened arnic acid, followed by self polymerization of the ring-opened amic acid at high temperature to form the aliphatic polyimide, wherein the diacid is citraconic acid.
8 . The aliphatic polyimide of claim 1 , wherein m is greater than about 20, wherein x is about 5 to about 25, and wherein y is about 2 to about 35.
9 . An aliphatic polyimide comprising poly-3-(4-alkyl-2,5-dioxo-1-pyrrolidine-N-alkylene amino).
10 . An aliphatic polyimide comprising poly-3-(3-alkylene-2,5-dioxo-1-pyrrolidine-N-alkylene amino).
11 . An aliphatic polyimide which is a reaction product of a 1:1 molar ratio of an unsaturated monoanhydride or an unsaturated diacid with a diamine.
12 . The aliphatic polyimide of claim 11 , wherein the unsaturated monoanhydride is selected from the group consisting of maleic anhydride, itaconic anhydride, citraconic anhydride, and combinations thereof.
13 . The aliphatic polyimide of claim 11 , wherein the unsaturated diacid is selected from the group consisting of itaconic acid, citraconic acid, or combinations thereof.
14 . The aliphatic polyimide of claim 11 , wherein the diamine is selected from the group consisting of 1,10 diaminodecane, hexamethylenediamine, 1,4 diaminobutane, ethylene diamine, 1, 9 diaminononane, aminopropyl terminated polydimethylsiloxane, polyetheramine, 1, 12 diaminododecane, and combinations thereof.
15 . The aliphatic polyimide of claim 1 , wherein any one of the monoanhydrides or the diacids or the diamines is a bio-derived monomer.
16 . A compound comprising the aliphatic polyimide of claim 1 and one or more functional additives.
17 . The compound of claim 16 , 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.