Interfacial processes for preparing photoactive additives

Abstract

Different interfacial processes for producing photoactive additives are disclosed. Generally, the photoactive additives are formed from a photoactive moiety, a first linker moiety, and a diol chain extender. The resulting additives can be crosslinked with other polymers upon exposure to UV radiation.

1 . A process for preparing a photoactive additive from a monohydroxybenzophenone, a dihydroxy compound, a carbonate precursor, a tertiary amine catalyst, water, and a water-immiscible organic solvent, comprising:
 combining the monohydroxybenzophenone, dihydroxy compound, tertiary amine catalyst, water, and water-immiscible solvent to form a reaction mixture; and   adding the carbonate precursor to the reaction mixture to obtain the photoactive additive.   
     
     
         2 . The process of  claim 1 , wherein the carbonate precursor is phosgene, the dihydroxy compound is bisphenol-A, and the water-immiscible organic solvent is methylene chloride. 
     
     
         3 . The process of  claim 1 , wherein a second end-capping agent is present in the reaction mixture in addition to the monohydroxybenzophenone. 
     
     
         4 . The process of  claim 3 , wherein the second end-capping agent is selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, octylphenol, and p-cyanophenol. 
     
     
         5 . The process of  claim 1 , wherein the reaction mixture further comprises a phase transfer catalyst. 
     
     
         6 . The process of  claim 1 , wherein the pH of the reaction mixture is maintained from about 8.5 to about 10 while the carbonate precursor is added to the reaction mixture. 
     
     
         7 . The process of  claim 1 , wherein the carbonate precursor is added to the reaction mixture over a time period of about 30 minutes to about 40 minutes. 
     
     
         8 . The process of  claim 1 , wherein the resulting photoactive additive contains about 100 ppm or less of diarylcarbonates. 
     
     
         9 . The process of  claim 1 , wherein the resulting photoactive additive does not contain residual pyridine. 
     
     
         10 . The process of  claim 1 , wherein the resulting photoactive additive comprises about 0.5 mole % to 5.0 mole % endcap groups derived from the monohydroxybenzophenone. 
     
     
         11 . The process of  claim 1 , wherein the resulting photoactive additive has a weight-average molecular weight of between 17,000 and 80,000 Daltons, as measured by GPC using a UV detector and polycarbonate molecular weight standards. 
     
     
         12 . The process of  claim 11 , wherein the ratio of the polydispersity index (PDI) measured using a UV detector to the PDI measured using an RI detector is 1.8 or less, when using a GPC method and polycarbonate molecular weight standards. 
     
     
         13 . The process of  claim 1 , wherein the resulting photoactive additive has a MVR of 2 to 4 cc/10 min measured according to ASTM D1238 at 300° C./1.2 kg. 
     
     
         14 . The process of  claim 1 , wherein the resulting photoactive additive has a MVR of 8 to 12 cc/10 min measured according to ASTM D1238 at 300° C./1.2 kg. 
     
     
         15 . A process for preparing a photoactive additive from a monohydroxybenzophenone, a dihydroxy compound, a carbonate precursor, a tertiary amine catalyst, water, and a water-immiscible organic solvent, comprising:
 combining the dihydroxy compound, tertiary amine catalyst, water, and water-immiscible solvent to form a reaction mixture;   adding the carbonate precursor to the reaction mixture over a first time period; and   adding the monohydroxybenzophenone to the reaction mixture during the first time period to obtain the photoactive additive.   
     
     
         16 . The process of  claim 15 , wherein the carbonate precursor is phosgene, the dihydroxy compound is bisphenol-A, and the water-immiscible organic solvent is methylene chloride. 
     
     
         17 . The process of  claim 15 , wherein the monohydroxybenzophenone is dissolved in a solvent prior to being added to the reaction mixture, the solvent being either the water-immiscible organic solvent or water containing a base. 
     
     
         18 . The process of  claim 17 , wherein the monohydroxybenzophenone is dissolved in a dilute aqueous sodium hydroxide solution. 
     
     
         19 . The process of  claim 18 , wherein the solution contains from about 1 to about 2 moles of NaOH per mole of the monohydroxy compound, and contains from about 5 wt % to about 20 wt % of the monohydroxy compound. 
     
     
         20 . The process of  claim 15 , wherein the monohydroxybenzophenone is added to the reaction mixture over a portion of the first time period corresponding to from 10% to about 40% of the total charge of the carbonate precursor. 
     
     
         21 . The process of  claim 15 , wherein a second end-capping agent is present in the reaction mixture in addition to the monohydroxybenzophenone. 
     
     
         22 . The process of  claim 15 , wherein the resulting photoactive additive contains less than 700 ppm of diarylcarbonates. 
     
     
         23 . The process of  claim 15 , wherein the resulting photoactive additive comprises about 0.5 mole % to 5.0 mole % endcap groups derived from the monohydroxybenzophenone. 
     
     
         24 . The process of  claim 15 , wherein the resulting photoactive additive has a weight-average molecular weight of between 17,000 and 80,000 Daltons, as measured by GPC using a UV detector and polycarbonate molecular weight standards. 
     
     
         25 . The process of  claim 24 , wherein the ratio of the PDI measured using a UV detector to the PDI measured using an RI detector is 1.5 or less when using a GPC method and polycarbonate molecular weight standards. 
     
     
         26 . The process of  claim 15 , wherein the resulting photoactive additive has a MVR of 2 to 4 cc/10 min measured according to ASTM D1238 at 300° C./1.2 kg. 
     
     
         27 . The process of  claim 15 , wherein the resulting photoactive additive has a MVR of 8 to 12 cc/10 min measured according to ASTM D1238 at 300° C./1.2 kg.