# US 2022/0017481 A1 · Method for purification of a bisphenol a dianhydride composition, bisphenol a dianhydride composition, poly(etherimide) derived from the bisphenol a dianhydride composition, and articles prepared therefrom

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- Number: US 2022/0017481 A1
- Document ID: US20220017481A1
- Status: Published application
- Kind: A1
- Application number: 17/418,446
- Filed: 2020-01-30
- Published: 2022-01-20
- Earliest claimed: 2019-01-31
- Assignees: Shpp Global Technologies B.V.
- Applicants: Shpp Global Technologies B.V.
- Inventors: James Patrick SCHULTE II
- Web page: https://patentgrep.com/patent/US20220017481A1

## CPC

- C07D 307/89: with two oxygen atoms directly attached in positions 1 and 3
- B01D 9/0054: {Use of anti-solvent}
- B01D 39/1669: {Cellular material}
- C08G 73/1014: {in the form of (mono)anhydrid}
- C08G 73/1053: {with oxygen only in the tetracarboxylic moiety}
- C08G 73/1064: {containing sulfur}
- C08G 73/1071: {Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain}
- B01D 2009/0086: {Processes or apparatus therefor}
- B01D 2201/184: Special form, dimension of the openings, pores of the filtering elements
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A method for the purification of a bisphenol A dianhydride composition includes contacting the bisphenol A dianhydride composition with a halogenated solvent to form a solution, and one or more of filtering the solution to remove ionic species; washing the solution with aqueous media to remove ionic species; crystallizing bisphenol A dianhydride from the solution to remove ionic species; and contacting the solution with an adsorbent to remove ionic species. A purified bisphenol A dianhydride composition is also described. The bisphenol A dianhydride composition can be used in the preparation of a poly(etherimide), and poly (etherimides) made from the bisphenol A dianhydride composition can be useful for forming a variety of articles.

## Claims

### Claim 1

A method for the purification of a bisphenol A dianhydride composition comprising
a bisphenol A dianhydride of the formula
wherein Ra and Rh are each independently a halogen or a monovalent Ci e alkyl group and p and q are each independently an integer of 0 to 4; and
at least one of sodium ions, potassium ions, calcium ions, zinc ions, aluminum ions, titanium ions, iron ions, phosphorus ions, phosphate ions, sulfate ions, chloride ions, nitrate ions, and nitrite ions;
the method comprising:
contacting the bisphenol A dianhydride composition with a halogenated solvent to form a solution; and
one or more of:
filtering the solution to remove ionic species;
washing the solution with aqueous media to remove ionic species;
crystallizing bisphenol A dianhydride from the solution to remove ionic species; and
contacting the solution with an adsorbent to remove ionic species.

### Claim 2 (depends on 1)

The method of claim 1, wherein the method includes filtering the solution, wherein the filtering comprises passing the solution through a filter having a pore size of less than or equal to 2 micrometers.

### Claim 3 (depends on 1)

The method of claim 1, wherein the method includes washing the solution with aqueous media, wherein the aqueous media comprises an aqueous caustic solution, and optionally, subsequently washing the solution with water.

### Claim 4 (depends on 1)

The method of claim 1, wherein the method includes crystallizing the bisphenol A dianhydride from the solution wherein crystallizing bisphenol A dianhydride comprises optionally adding an antisolvent to the solution and cooling to a temperature effective to provide a slurry.

### Claim 5 (depends on 4)

The method of claim 4, wherein the antisolvent is a non-polar solvent.

### Claim 6 (depends on 1)

The method of claim 1, wherein the method includes contacting the solution with the adsorbent, wherein the adsorbent comprises celite, diatomaceous earth, silica, alumina, or a combination thereof, and wherein the method further comprises filtering the solution comprising the adsorbent through a filter having a pore size of 16 micrometers or less.

### Claim 7 (depends on 1)

The method of claim 1, wherein the halogenated solvent comprises ortho-dichlorobenzene, para-dichlorobenzene, meta-dichlorobenzene, trichlorobenzene, or a combination thereof.

### Claim 8 (depends on 1)

The method of claim 1, wherein the divalent bonds of the bisphenol A group are in the 3,3′ position, the 3,4′ position, or the 4,4′ position.

### Claim 9 (depends on 1)

The method of claim 1, wherein the bisphenol A dianhydride is an isomer mixture.

### Claim 10 (depends on 1)

A bisphenol A dianhydride made by the method of claim 1, wherein the purified bisphenol A dianhydride comprises
less than 25 ppm each of sodium ions, potassium ions, calcium ions, zinc ions, aluminum ions, titanium ions, iron ions, and phosphorus ions; and
less than 50 ppm each of phosphate ions, sulfate ions, chloride ions, nitrate ions, and nitrite ions.

### Claim 11 (depends on 1)

The method of claim 1, wherein the bisphenol A dianhydride composition is made by a method comprising
hydrolyzing a bisphenol A bisimide to form a corresponding bisphenol A tetraacid salt; contacting the bisphenol A tetraacid salt with a mineral acid to form a corresponding bisphenol A tetraacid;
contacting the bisphenol A tetraacid with a halogenated solvent to form a reaction mixture;
heating the reaction mixture to a temperature effective to form the corresponding bisphenol A dianhydride from the bisphenol A tetraacid, optionally in the presence of a mineral acid; and
isolating the bisphenol A dianhydride from the reaction mixture;
wherein the method is carried out in the absence of an organic acid, an organic anhydride different from the bisphenol A dianhydride, or both.

### Claim 12 (depends on 1)

A poly(etherimide) comprising repeating units derived from polymerization of the purified bisphenol A dianhydride composition made by the method of claim 1 and an organic diamine, wherein the poly(etherimide) comprises less than 25 ppm each of sodium ions, potassium ions, calcium ions, zinc ions, aluminum ions, titanium ions, iron ions, and phosphorus ions and less than 25 ppm each of phosphate ions, sulfate ions, chloride ions, nitrate ions, and nitrite ions.

### Claim 13 (depends on 12)

The poly(etherimide) of claim 12, wherein the organic diamine is 4,4′-diaminodiphenylsulfone, 3,4′-diaminodiphenylsulfone, 3,3′-diaminodiphenylsulfone, meta-phenylene diamine, para-phenylene diamine, ortho-phenylene diamine, or a combination thereof.

### Claim 14 (depends on 12)

An article comprising the poly(etherimide) of claim 12.

### Claim 15

A method for purification of a bisphenol A tetraacid composition comprising a bisphenol A tetraacid of the formula
wherein Ra and Rb are each independently a halogen or a monovalent Ci 6 alkyl group and p and q are each independently an integer of 0 to 4; and
at least one of sodium ions, potassium, calcium, sulfate, phosphate, nitrate, nitrite, and chloride ions;
the method comprising:
washing the bisphenol A tetraacid composition with water at a temperature of 85 to 95 degrees;
optionally, agitating the composition during the washing; and
collecting a purified bisphenol A tetraacid composition;
wherein the purified bisphenol A tetraacid composition comprises less than 100 ppm each of sodium ions, potassium ions, calcium ions and less than 900 ppm each of sulfate ions, phosphate ions, nitrate ions, and nitrite ions.
