Polyetherimides with improved melt stability

Patent metadata

Field	Value
Publication number	US-10676571-B2
Application number	US-201314094104-A
Country	US
Kind code	B2
Filing date	Dec 2, 2013
Priority date	Dec 2, 2013
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

A polyetherimide composition comprises the polymerization product of a catalyzed imidization product of a 3-substituted phthalic anhydride and a sulfone diamine having improved melt stability and reduced corrosivity, and a method of manufacture thereof.

First claim

What is claimed is:

1. A method for the manufacture of a polyetherimide composition having improved melt stability, the method consisting of catalyzing imidization of a 3-substituted phthalic anhydride of the formula

with a sulfone diamine selected from 3,3′-diaminodiphenyl sulfone, 3,4′-diaminodiphenyl sulfone, 4,4′-diaminodiphenyl sulfone, and combinations thereof with a hexa(C 1-6 )alkylguanidinium salt catalyst, a α,ω-bis(penta(C 1-6 )alkylguanidinium)(C 1-6 )alkane salt catalyst or a combination thereof in the presence of a solvent, to provide a bis(phthalimide) composition comprising a residue of the catalyst and a 3,3′-bis(phthalimide) of the formula

wherein the 3-substituted phthalic anhydride and the sulfone diamine convert to the 3,3′-bis(phthalimide) to at least 99% completion, and
catalyzing polymerization of the 3,3′-bis(phthalimide) and an alkali metal salt of a dihydroxy aromatic compound of the formula
MO—Z—OM

in the presence of the catalyst that catalyzes the imidization of the 3-substituted phthalic anhydride and the sulfone diamine to form the polyetherimide composition consisting of
a residue of the catalyst and
a polyetherimide of the formula

wherein in the foregoing formulae
X is selected from fluoro, chloro, bromo, iodo, and combinations thereof;
R is selected from 3,3′-diphenylene sulfone, 3,4′-diphenylene sulfone, 4,4′-diphenylene sulfone, and combinations thereof;
M is an alkali metal;
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 combinations thereof; and
n is an integer greater than 1;
wherein the polyetherimide has a Tg that is more than 247° C., no detectable amount of sodium aryl phosphinate salt, and,
wherein the polyetherimide, in molten form, has a viscosity that is the same viscosity as the initial viscosity or less than the initial viscosity after the polyetherimide is exposed to a temperature that is at least 400° C. for at least 5 minutes, the initial viscosity being the viscosity the polyetherimide has after the polyetherimide has been exposed to at least 400° C. for six minutes.

2. The method of claim 1 , wherein the polyetherimide is exposed to a temperature of 770° F. (410° C.).

3. The method of claim 1 , wherein the 3-substituted phthalic anhydride and the sulfone diamine converts to the 3,3′-bis(phthalimide) in a conversion of at least 99.5%.

4. The method of claim 1 , wherein the polyetherimide has a glass transition temperature, Tg, that is at least 260° C.

5. The method of claim 4 , wherein X is chloro, and Z is 2,2-(4-phenylene) isopropylidene.

6. The method of claim 1 , wherein the polyetherimide retains a melt stability that is at least 95% when the polyetherimide is exposed to a temperature of 770° F. (410° C.) for 9 minutes.

7. The method of claim 1 , wherein the catalyst is present in an amount ranging from 0.05 to 1 mole % based on the moles of the sulfone diamine during the imidization, and a second catalyst is added before the polymerization, wherein the second catalyst is the same catalyst used for the imidization.

8. The method of claim 1 , wherein the catalyst is hexaethylguanidinium chloride.

9. The method of claim 1 , wherein the 3,3′-bis(phthalimide) composition and the polyetherimide composition are manufactured in the same vessel.

10. The method of claim 1 , wherein X is chloro, fluoro, or bromo, 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.

11. The method of claim 1 , wherein less than 1000 ppm of the residue of the catalyst, based on the weight of the polyetherimide is present in the polyetherimide composition.

12. An article comprising the polyetherimide composition manufactured by the method of claim 1 .

13. The article of claim 12 , selected from a sheet, film, multilayer sheet, multilayer film, molded part, extruded shape, coated part, molded shape, pellet, powder, foam, fiber, fibrid, flaked fiber, and combinations thereof.

14. The article of claim 12 , wherein the article is a molded part.

15. The article of claim 14 , wherein the molded part is an injection molded part.

16. The article of claim 12 , wherein the article is a sheet or film and further comprises a conductive metal layer disposed on a side thereof.

17. The article of claim 12 , wherein the article is an optical lens.

18. The article of claim 12 , wherein the article is an optical fiber connector, an electrical connector, an LED reflector, a printed circuit board substrate, or a reflector for automotive headlamp.

19. A polyetherimide composition consisting of
(i) a polyetherimide of the formula

and
(ii) a residue of a guanidinium catalyst and optionally, a residue of a catalyst selected from quaternary ammonium salts, quaternary phosphonium salts, pyridinium salts, imidazolium salts, and combinations thereof, wherein the guanidinium catalyst comprises hexa(C 1-6 )alkylguanidinium salt catalyst, a α,ω-bis(penta(C 1-6 )alkylguanidinium)(C 1-6 )alkane salt catalyst or a combination thereof, wherein the guanidinium catalyst residue is present in an amount less than 1000 ppm, based on the weight of the polyetherimide,
the polyetherimide being a catalyzed polymerization reaction product of (1) a 3,3′-bis(phthalimide) composition comprising a catalyzed imidization product of a 3-substituted phthalic anhydride and a sulfone diamine selected from 3,3′-diaminodiphenyl sulfone, 3,4′-diaminodiphenyl sulfone, 4,4′-diaminodiphenyl sulfone, and combinations thereof, and (2) an alkali metal salt of a dihydroxy aromatic compound, the imidization product being catalyzed by the guanidinium catalyst;
wherein
the substituted 3-phthalic anhydride has a formula

the sulfone diamine has a formula
H 2 N—R—NH 2 ,

the 3,3′-bis(phthalimide) has a formula

and
the alkali metal salt of the dihydroxy aromatic compound has a formula
MO—Z—OM,

wherein in the foregoing formulae,
X is selected from fluoro, chloro, bromo, iodo, and combinations thereof;
R is selected from 3,3′-diphenylene sulfone, 3,4′-diphenylene sulfone, 4,4′-diphenylene sulfone, and combinations thereof;
M is an alkali metal;
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 combinations thereof; and
n is an integer greater than 1;
wher

Assignees

• Sabic Global Technologies Bv

Inventors

• Zhou Hao
• Chellamuthu Manojkumar
• Royer Aaron

Classifications

• B29C45/00

  Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor (injection blow-moulding B29C49/06) · CPC title

• C08G73/1071 Primary

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title

• B29C49/00

  Blow-moulding, i.e. blowing a preform or parison to a desired shape within a mould; Apparatus therefor · CPC title

• B29K2079/085

  Thermoplastic polyimides, e.g. polyesterimides, PEI, i.e. polyetherimides, or polyamideimides; Derivatives thereof · CPC title

• Y10T428/31681

  Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.] · CPC title