Methods for purifying 2-aryl-3,3-bis(hydroxyaryl)phthalimidines

• US 7,790,832 B2
• Filed: 09/04/2007
• Issued: 09/07/2010
• Est. Priority Date: 12/14/2005
• Status: Active Grant

• Current Assignee: SHPP Global Technologies BV
• Original Assignee: Sabic Innovative Plastics IP BV (Government of Saudi Arabia)
• Inventors: Ganesan, Balakrishnan, Bhotla, Venkata Rama Narayanan Ganapathy, Nadkarni, Pradeep Jeevaji, Kishan, Gurram, Satyanarayana, Kumar Arun, Singh, Ravindra Vikram, Shanumgam, Suresh
• Primary Examiner(s): Boykin; Terressa M
• Application Number:
  US11/849,523
• Publication Number:
  US 20080058497A1
• Time in Patent Office: 1,099 Days
• Field of Search: 528/196, 528/198, 528/210, 548/467, 548/472, 548/487, 514/415, 526/64
• US Class Current: 528/196
• CPC Class Codes: C07D 209/46 with an oxygen atom in position 1
• CPC Class Codes: C08G 64/12 containing nitrogen

Abstract

A method for purifying a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine comprises contacting a crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine with a purification agent, removing a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound from the crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine, and producing a purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product comprising less than 200 parts per million of the 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound. The purification agent is selected from the group consisting of an acidic material, an organic acid chloride, an organic anhydride, or a combination thereof. The 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound has a formula:

wherein each R¹ is independently selected from a group consisting of a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 0 to 4; and Ar¹ and Ar² are independently at each occurrence an aromatic radical. The purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidines have low color, and are useful for preparing polymers, such as polycarbonates having a low color. The polycarbonates are useful for producing articles.

Claims

1. A method for purifying a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound, the method comprising:

contacting a crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound with a solid acidic material, an organic acid chloride, an organic anhydride, a solution of a mineral acid in a polar organic solvent, a solution of an organosulfonic acid having 2 or more carbon atoms in an organic solvent, acetic acid, or a combination thereof, to remove a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound having a formula;

2. The method of claim 1, further comprising treating the purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product with a polar organic solvent and reducing an APHA value of the product to less than 20 as measured using test method ASTM D1209.

3. The method of claim 1, wherein the solid acidic material comprises an acidic metal oxide, an acidic organic polymer, or a combination of the acidic metal oxide and the acidic organic polymer.

4. The method of claim 3, wherein the acidic metal oxide comprises an acidic silica, an acidic alumina, an acid-washed carbon, or a sulfated zirconia.

5. The method of claim 3, wherein the acidic organic polymer is selected from the group consisting of a poly(vinylsulfonic acid), a poly(vinylphosphonic acid), and an acidic ion exchange resin.

6. The method of claim 5, wherein the acidic ion exchange resin is a sulfonated polystyrene-divinylbenzene copolymer crosslinked with up to 20 weight percent of divinylbenzene relative to an overall weight of the acidic ion exchange resin.

7. The method of claim 3, wherein the organosulfonic acid having 2 or more carbon atoms is selected from the group consisting of ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, octanesulfonic acid, dodecylbenzenesulfonic acid, and a combination of the foregoing organosulfonic acids.

8. The method of claim 1, wherein the acid in a polar organic solvent is an alcoholic mineral acid, wherein the mineral acid is selected from the group consisting of phosphoric acid, hydrochloric acid, and a combination of the foregoing mineral acids.

9. The method of claim 1, wherein the organic anhydride is phthalic anhydride.

10. The method of claim 1, further comprising recycling the purification agent, wherein the purification agent is an acidic ion exchange resin.

11. The method of claim 1, further comprising contacting the purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product with a metal oxide for a period of time effective to reduce one more metal impurity concentrations to less than 500 parts per billion of each metal and produce an ultra-pure 2-aryl-3,3-bis(hydroxyaryl)phthalimidine.

12. The method of claim 11, wherein the metal oxide comprises a basic metal oxide, a neutral metal oxide, or an acidic metal oxide.

13. The method of claim 11, wherein the metal oxide is selected from the group consisting of an acidic silica and an acidic alumina.

14. The method of claim 11, further comprising washing the metal oxide with an aqueous mineral acid prior to contacting the purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product with the metal oxide.

15. The method of claim 14, wherein the aqueous mineral acid is hydrochloric acid.

16. The method of claim 11, wherein the one or more metal impurities is selected from the group consisting of iron, calcium, zinc, aluminum, and sodium.

17. The method of claim 1, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine is 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimidine.

18. A polymer comprising structural units derived from the purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product of claim 1.

19. A polycarbonate comprising structural units derived from the purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product of claim 2 and having an APHA value of less than 20 as measured using test method ASTM D1209, and

wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine has the structure of formula (I):

27. The method of claim 16, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has less than 500 parts per billion of each of iron, calcium, sodium, aluminum, and zinc individually.

20. A method for preparing an ultra-pure 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product, the method comprising:

contacting a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine with a solid acidic material, an organic acid chloride, an organic anhydride, a solution of an acid in a polar organic solvent, a solution of an organosulfonic acid having 2 or more carbon atoms in an organic solvent, acetic acid, or a combination thereof, to produce a purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product comprising one or more metal impurities at a concentration of greater than 500 parts per billion of each metal, and less than 200 parts per million of a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine having a formula;

21. The method of claim 20, further comprising treating the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine with a polar organic solvent prior to contacting with the metal oxide adsorbent, to produce a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine having an APHA value of less than 10 as measured using test method ASTM D1209.

28. The method of claim 20, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has less than 500 parts per billion of each of iron, calcium, sodium, aluminum, and zinc individually.

22. A method for preparing a polycarbonate polymer comprising structural units derived from a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound, the method comprising:

reacting a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound with a carbonate precursor to produce the polycarbonate polymer, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has less than 200 parts per million of a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine having a formula;

23. The method of claim 22, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has less than 500 parts per billion of at least three of iron, calcium, sodium, aluminum, and zinc.

24. The method of claim 22, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has an APHA value of less than 20 as measured using test method ASTM D1209.

25. The method of claim 22, wherein the polycarbonate has a yellowness index of less than 10 as measured using test method ASTM E313-00.

29. The method of claim 22, wherein the 2-aryl-3,3-bis(hydroxyaryl)phthalimidine compound has less than 500 parts per billion of each of iron, calcium, sodium, aluminum, and zinc individually.

26. A polycarbonate comprising structural units derived from an ultra-pure 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimidine product, wherein the ultra-pure 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimidine product comprises less than 200 parts per million of 2-phenyl-3-(4-aminophenyl)-3-(4-hydroxyphenyl)phthalimidine;

and less than 500 parts per billion of at least three of iron, calcium, sodium, aluminum, and zinc individually.

30. The polycarbonate of claim 26, wherein the 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimidine compound has less than 500 parts per billion of each of iron, calcium, sodium, aluminum, and zinc individually.