Polyetherimide compositions, methods of manufacture, and articles formed therefrom
View Patent ↗A method for the manufacture of a polyetherimide composition includes catalyzing the reaction of a dianhydride and an organic diamine with a catalyst selected from guanadinium salts, pyridinium salts, imidazolium salts, tetra(C 6-24 )aryl ammonium salts, tetra(C 7-24 arylalkylene) ammonium salts, dialkyl heterocycloaliphatic ammonium salts, bis-alkyl quaternary ammonium salts, (C 7-24 arylalkylene)(C 1-16 alkyl) phosphonium salts, (C 6-24 aryl)(C 1-16 alkyl)phosphonium salts, phosphazenium salts and combinations thereof, optionally in the presence of a solvent.
1. A method for the manufacture of a polyetherimide composition, the method comprising catalyzing the reaction of a dianhydride and an organic diamine with a guanidinium salt catalyst, optionally in the presence of a solvent, to provide the polyetherimide composition comprising a residue of the catalyst and a polyetherimide;
wherein
the dianhydride has the formula
the diamine has the formula
H 2 N—R—NH 2 ; and
the polyetherimide has the formula
wherein in the forgoing formulae:
T is —O— or a group of the formula —O—Z—O—, wherein Z is an aromatic C 6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 C 1-8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof;
R is selected from an aromatic hydrocarbon group having 6 to 27 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a halogenated derivative thereof, a cycloalkylene group having 3 to 20 carbon atoms, a halogenated derivative thereof, a divalent group of the formula
wherein Q 1 is selected from —O—, —S—, —C(O)—, —SO 2 —, —SO—, and —C y H 2y — and a halogenated derivative thereof wherein y is an integer from 1 to 5, and —(C 6 H 10 ) z — wherein z is an integer from 1 to 4, and an aromatic hydrocarbyl moiety having from 1 to 6 aromatic groups; and
n is an integer greater than 1;
wherein the catalyst is present in an amount of 0.01 to 2 mole %, based on the moles of the diamine.
2. The method of claim 1 , wherein the reaction of the dianhydride and the diamine is complete in less than or equal to 20 hours.
3. The method of claim 1 , comprising combining the dianhydride, the organic diamine, the catalyst, and optionally the solvent before heating the combination.
4. The method of claim 1 , wherein the reaction is conducted under melt polymerization conditions.
5. The method of claim 1 , wherein the reaction is conducted under solution polymerization conditions.
6. The method of claim 1 , wherein the reaction is conducted in the further presence of an endcapping agent.
7. The method of claim 6 , wherein the endcapping agent is phthalic anhydride, aniline, a C1-C18 linear, branched or cyclic aliphatic monoamine or a monofunctional aromatic amine.
8. The method of claim 1 , wherein the molar ratio of the dianhydride to the organic diamine is 0.9:1 to 1.5:1.
9. The method of claim 1 , wherein the catalyst is present in an amount of 0.2 to 1.0 mole percent, based on the moles of the organic diamine.
10. The method of claim 1 , wherein the catalyst is present in an amount of 0.1 to 1 mole %, based on the moles of the organic diamine.
11. The method of claim 1 , wherein the catalyst is hexaethylguanidinium chloride.
12. The method of claim 1 , wherein the catalyst is a guanidinium salt, and a residue of the guanidinium salt is present in the polyetherimide composition in an amount less than 1000 ppm, based on parts by weight of the polyetherimide composition.
13. The method of claim 1 , wherein the polyetherimide composition comprises less than 100 ppm of a sodium aryl phosphinate salt, based on the weight of the polyetherimide composition.
14. The method of claim 13 , wherein the polyetherimide composition comprises no detectable amount of the sodium aryl phosphinate salt.
15. The method of claim 1 , wherein
R is a divalent radical of the formula —(C 6 H 10 ) z — wherein z is an integer from 1 to 4,
and combinations thereof, wherein Q 1 is selected from a single bond, —O—, —S—, —C(O)—, —SO 2 —, —SO—, —C y H 2y — wherein y is an integer from 1 to 5, and combinations thereof; and
Z is a divalent group of formula
wherein
R a and R b are each a halogen atom or a monovalent hydrocarbon group and can be the same or different;
X a is a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic group;
p and q are each independently integers of 0 to 4; and
c is 0 or 1.
16. The method of claim 1 , wherein
Z is 2,2-(4-phenylene)isopropylidene, and
R is m-phenylene, p-phenylene, diarylsulfone, or a group of the formula
wherein Q 1 is —is a member selected from the group of a single bond, —O—, —S—, —C(O)—, —SO 2 —, —SO—, —C y H 2y wherein y is an integer from 1 to 5, and combinations thereof.
17. A method for the manufacture of a polyetherimide composition, the method comprising catalyzing the reaction of a dianhydride and an organic diamine with a guanidinium salt catalyst, optionally in the presence of a solvent, to provide the polyetherimide composition comprising a residue of the catalyst and a polyetherimide;
wherein
the dianhydride has a formula of
the diamine has a formula of
H 2 N—R—NH 2 ; and
the polyetherimide has a formula of
wherein in the forgoing formulae:
R is selected from
and combinations thereof; and
n is an integer greater than 1;
wherein the reaction of the dianhydride and the diamine is complete in less than or equal to 20 hours; and
wherein the catalyst is present in an amount of 0.01 to 2 mole %, based on the moles of the diamine.
18. The method of claim 17 , wherein the reaction is conducted under melt polymerization conditions.
19. The method of claim 17 , wherein the reaction is conducted under solution polymerization conditions.
20. The method of claim 17 , wherein the reaction is conducted in the further presence of an endcapping agent.
21. The method of claim 20 , wherein the endcapping agent is phthalic anhydride, aniline, a C1-C18 linear, branched or cyclic aliphatic monoamine, or a monofunctional aromatic amine.
22. The method of claim 17 , wherein the molar ratio of the dianhydride to the organic diamine is 0.9:1 to 1.5:1.
23. The method of claim 17 , wherein the catalyst is present in an amount of 0.2 to 1.0 mole percent, based on the moles of the organic diamine.
24. The method of claim 17 , wherein the catalyst is present in an amount of 0.1 to 1 mole %, based on the moles of the organic diamine.
25. The method of claim 17 , wherein the catalyst is hexaethylguanidinium chloride.
26. A composition comprising
a guanidinium salt catalyst;
a dianhydride having a formula of
and
a diamine having a formula of
H 2 N—R—NH 2
wherein in the forgoing formulae:
T is —O— or a group of the formula —O—Z—O—, wherein Z is an aromatic C 6-24 monocyclic or polycyclic moiety optionally substituted with 1 to 6 C 1-8 alkyl groups, 1 to 8 halogen atoms, or a combination thereof; and
R is selected from an aromatic hydrocarbon group having 6 to 27 carbon atoms, a halogenated derivative thereof, a straight or branched chain alkylene group having 2 to 10 carbon atoms, a halogenated derivative thereof, a cycloalkylene group having 3 to 20 carbon atoms, a halogenated derivative thereof, a divalent group of the formula
wherein Q 1 is selected from —O—, —S—, —C(O)—, —SO 2 —, —SO—, and —C y H 2y — and a halogenated derivative thereof wherein y is an integer from 1 to 5, and —(C 6 H 10 ) z — wherein z is an integer from 1 to 4, and an aromatic hydrocarbyl moiety having from 1 to 6 aromatic groups;
wherein the catalyst is present in an amount of 0.01 to 2 mole %, based on the moles of the diamine.
27. The composition of claim 26 , further comprising an endcapping agent.