Interfacial processes for preparing photoactive additives
View Patent ↗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 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;
wherein the monohydroxybenzophenone is dissolved in a dilute aqueous sodium hydroxide solution prior to being added to the reaction mixture, wherein the solution contains from about 1 to about 2 moles of NaOH per mole of the monohydroxybenzophenone, and contains from about 5 wt % to about 20 wt % of the monohydroxybenzophenone.
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 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.
4. The process of claim 1 , wherein a second end-capping agent is present in the reaction mixture in addition to the monohydroxybenzophenone.
5. The process of claim 4 , wherein the second end-capping agent is selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, octylphenol, and p-cyanophenol.
6. The process of claim 1 , wherein the resulting photoactive additive contains less than 700 ppm of diarylcarbonates.
7. 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.
8. 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.
9. The process of claim 8 , wherein the resulting photoactive additive has a weight-average molecular weight of between 17,000 and 35,000 Daltons, as measured by GPC using a UV detector and polycarbonate molecular weight standards.
10. The process of claim 8 , 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.
11. 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.
12. 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.
13. 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;
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.
14. The process of claim 13 , wherein the carbonate precursor is phosgene, the dihydroxy compound is bisphenol-A, and the water-immiscible organic solvent is methylene chloride.
15. The process of claim 13 , 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.
16. The process of claim 15 , wherein the monohydroxybenzophenone is dissolved in a dilute aqueous sodium hydroxide solution.
17. The process of claim 16 , 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.
18. The process of claim 13 , wherein a second end-capping agent is present in the reaction mixture in addition to the monohydroxybenzophenone.
19. The process of claim 18 , wherein the second end-capping agent is selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, octylphenol, and p-cyanophenol.
20. The process of claim 13 , wherein the resulting photoactive additive contains less than 700 ppm of diarylcarbonates.
21. The process of claim 13 , wherein the resulting photoactive additive comprises about 0.5 mole % to 5.0 mole % endcap groups derived from the monohydroxybenzophenone.
22. The process of claim 13 , 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.
23. The process of claim 22 , wherein the resulting photoactive additive has a weight-average molecular weight of between 17,000 and 35,000 Daltons, as measured by GPC using a UV detector and polycarbonate molecular weight standards.
24. The process of claim 22 , 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.
25. The process of claim 13 , 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.
26. The process of claim 13 , 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.