Sabic Innovative Plastics IP B.v.

General Electric Company

Suresh Shanmugam

Anantharaman Dhanabalan

Pradeep Jeevaji Nadkarni

Gautam Chatterjee

Gurram Kishan

Veeraraghavan Srinivasan

Balakrishnan Ganesan

Vinod Kumar Rai

Ravindra Vikram Singh

Katherine Campbell Glasgow

Venkata Rama Narayanan Ganapathy Bhotla

Kumar Arun Satyanarayana

Rajshekhar Basale

Venkata Rama Narayanan Ganapathy Bholta

Surendra Kulkarni

Gv Ramanarayanan

S Arun Kumar

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 Ris 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 Arand Arare 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.

Purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidines

Disclosed herein is a method comprising reacting a phenolphthalein material and a primary hydrocarbyl amine in the presence of an acid catalyst to form a reaction mixture comprising 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the phenolphthalein material comprises greater than or equal to 95 weight percent phenolphthalein, based on the total weight of phenolphthalein material; quenching the reaction mixture and treating the quenched reaction mixture to obtain a first solid. The first solid is then triturated with a trituration solvent and washed to obtain a second solid, wherein the second solid comprises greater than or equal to 97 weight percent 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, based on the total weight of the second solid. The second solid may be polymerized to form a polycarbonate.

Methods for producing and purifying 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine monomers and polycarbonates derived therefrom

A composition comprising a polycarbonate, wherein the polycarbonate has a weight average molecular weight of greater than 15,000, comprises more than 15 mole percent structural units derived from a 2-aryl-3,3-bis(4-hydroxyaryl)phthalimide: 

Disclosed herein is a method for producing a 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine. The method comprises forming a reaction mixture comprising at least one substituted or unsubstituted phenolphthalein, at least one substituted or unsubstituted primary hydrocarbyl amine, and an acid catalyst; and heating the reaction mixture to a temperature of less than 180&#xb0; C. to remove a distillate comprising water and form a crude 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine product; where the 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine has a formula: where Ris selected from the group consisting of a hydrogen and a hydrocarbyl group, and Ris selected from the group consisting of a hydrogen, a hydrocarbyl group, and a halogen.

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Bengaluru, India

Suresh Shanmugam