Polycarbonate with reduced color
View Patent ↗A method of making polycarbonate includes the steps of forming polycarbonate by a melt transesterification method using an activated diaryl carbonate, and compounding the polycarbonate with a phosphorus-containing compound that has an abstractable proton or hydrolyzable group. The phosphorus-containing compound is compounded with the polycarbonate in an amount sufficient to result in an improvement in the color properties of the polycarbonate as compared to pellets formed from the same polycarbonate without addition of the phosphorus-containing compound.
1. A method of making polycarbonate, comprising the steps of:
(a) forming polycarbonate by a melt transesterification method using an activated diaryl carbonate, and
(b) compounding the polycarbonate with a phosphorus-containing compound that has an abstractable proton or hydrolyzable group, wherein the phosphorous-containing compound is compounded with the polycarbonate in an amount sufficient to result in an increase in the L* color value, thereby improving the color properties of the polycarbonate as compared to pellets formed from the same polycarbonate without addition of the phosphorus-containing compound.
2. The method of claim 1 , wherein the phosphorus-containing compound is a compound having structure I or II:
wherein R 1 and R 2 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
3. The method of claim 2 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
4. The method of claim 1 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
5. The method of claim 4 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
6. The method of claim 4 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ), dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ), diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 ), propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C 12 H 24 N 3 OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP), N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 ClN 2 OP), hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 P), diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P-phenylphosphonic diamide (C 10 H 17 N 2 OP).
7. The method of claim 1 , wherein the activated diaryl carbonate is bismethylsalicylcarbonate.
8. The method of claim 7 , wherein the phosphorus-containing compound is phosphorous acid.
9. The method of claim 7 , wherein the polycarbonate is a terpolymer.
10. The method of claim 9 , wherein the phosphorus-containing compound is phosphorous acid.
11. The method of claim 1 , wherein the phosphorous-containing compound is compounded with the polycarbonate in an amount of at least 5 ppm.
12. The method of claim 1 , wherein the phosphorous containing compound is compounded with the polycarbonate in an amount such that the molar ratio of phosphorous atoms to transesterification catalyst (P/cat) used in forming the polycarbonate is between 1 and 20.
13. A method for reducing the color of a polycarbonate made by transesterification using an activated diaryl-carbonate, said method comprising the steps of a compounding the phosphorus-containing compound that has an abstractable proton or hydrolyzable group, wherein the phosphorous-containing compound is compounded with the polycarbonate in an amount sufficient to result in an increase in the L* color value, thereby improving the color properties of the polycarbonate as compared to pellets formed from the same polycarbonate without addition of the phosphorus-containing compound.
14. The method of claim 13 , wherein the polycarbonate before compounding with the phosphorus-containing compound has an L* value of less than 80, and after compounding has an L* value of greater than 80.
15. The method of claim 13 , wherein the phosphorus-containing compound comprises a compound having structure I, II:
wherein R 1 and R 2 are independently hydrogen; O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy; O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
16. The method of claim 13 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
17. The method of claim 13 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
18. The method of claim 17 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
19. The method of claim 17 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ), dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ), diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 ), propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C 12 H 24 N 3 OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP), N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 ClN 2 OP), hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 P), diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P-phenylphosphonic diamide (C 10 H 17 N 2 OP).
20. The method of claim 13 , further comprising the step of:
(c) forming polycarbonate pellets from the polycarbonate compounded with a phosphorus-containing compound.
21. A polycarbonate composition, characterized in that the polycarbonate contains quinone residues, internal ester linkages derived form the activated diaryl carbonate and at least ppb levels of phosphorous, and an L* value of greater than 85.
22. A method of making a stabilized polycarbonate blend, comprising the steps of:
(a) forming polycarbonate by a melt transesterification method using a diaryl carbonate and a quinone-type monomer, and
(b) compounding the polycarbonate with a phosphorus-containing compound and a UV stabilizer having a free —OH group, thereby forming a blend,
wherein the phosphorus-containing compound has an abstractable proton or hydrolyzable group, and
wherein the phosphorous-containing compound is compounded with the UV stabilizer and the polycarbonate in an amount sufficient to result in an increase in the retention of UV stabilizer in the blend and an increase the retention of molecular weight of the polycarbonate in the blend during a molding step, thereby improving the melt stability properties of the blend as compared to a blend formed from the same polycarbonate and UV stabilizer without the addition of the phosphorus-containing compound during a similar molding step.
23. The method of claim 22 , wherein the phosphorus-containing compound is a compound having structure I or II:
wherein R 1 and R 2 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
24. The method of claim 23 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
25. The method of claim 22 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
26. The method of claim 25 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
27. The method of claim 25 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ), dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ), diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 ), propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C 12 H 24 N 3 OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP), N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 C1N 2 OP), hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 P), diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P-phenylphosphonic diamide (C 10 H 17 N 2 OP).
28. The method of claim 22 , wherein the diaryl carbonate is an activated diaryl carbonate and is bismethylsalicylcarbonate.
29. The method of claim 28 , wherein the phosphorus-containing compound is phosphorous acid.
30. The method of claim 22 , wherein the amount phosphorous-containing compound compounded with the polycarbonate and the UV stabilizer is in an amount to provide a molar ratio of phosphorus atoms to transesterification catalyst used in forming the polycarbonate (P/cat) of between 1:1 and 10:1.
31. The method of claim 30 , wherein the molar ratio is between 5:1 and 10:1.
32. The method of claim 22 , wherein the quinone-type monomer is selected from the group consisting of hydroquinone, methylhydroquinone, butylhydroquinone, and phenylhydroquinone.
33. A stabilized polycarbonate blend, comprising
(a) a melt polycarbonate comprising a residue from a quinone-type monomer,
(b) a UV stabilizer having a free —OH group, and
(c) a phosphorus-containing compound having an abstractable proton or hydrolyzable group, wherein the phosphorous-containing compound is present in the blend in an amount sufficient to result in an increase in the retention of UV stabilizer in the blend and an increase the retention of molecular weight of the polycarbonate in the blend during a molding step, thereby improving the melt stability properties of the blend as compared to a blend formed from the same polycarbonate and UV stabilizer without the addition of the phosphorus-containing compound during a similar molding step.
34. The blend of claim 33 , wherein the phosphorus-containing compound is a compound having structure I or II:
wherein R 1 and R 2 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
35. The blend of claim 34 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
36. The blend of claim 33 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
37. The blend of claim 36 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
38. The blend of claim 36 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ), dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ), diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 ), propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C 12 H 24 N 3 OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP), N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 C1N 2 OP), hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 P), diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P-phenylphosphonic diamide (C 10 H 17 N 2 OP).
39. The blend of claim 38 , wherein the phosphorus-containing compound is phosphorous acid.
40. The blend of claim 33 , wherein the blend further comprises a transesterification catalyst and wherein the phosphorous-containing compound is present in the blend in an amount to provide a molar ratio of phosphorus atoms to transesterification catalyst (P/cat) of between 1:1 and 10:1.
41. The blend of claim 40 , wherein the molar ratio is between 5:1 and 10:1.
42. The blend of claim 33 , wherein the quinone-type monomer is selected from the group consisting of hydroquinone, methylhydroquinone, butylhydroquinone, and phenylhydroquinone.
43. A method of making a stabilized polycarbonate blend, comprising the steps of:
(a) forming polycarbonate by a melt transesterification method using a activated diaryl carbonate, and
(b) compounding the polycarbonate with a phosphorus-containing compound and a UV stabilizer having a free -OH group, thereby forming a blend,
wherein the phosphorus-containing compound has an abstractable proton or hydrolyzable group, and
wherein the phosphorous-containing compound is compounded with the UV stabilizer and the polycarbonate in an amount sufficient to result in an increase in the retention of UV stabilizer in the blend and an increase the retention of molecular weight of the polycarbonate in the blend during a molding step, thereby improving the melt stability properties of the blend as compared to a blend formed from the same polycarbonate and UV stabilizer without the addition of the phosphorus-containing compound during a similar molding step.
44. The method of claim 43 , wherein the phosphorus-containing compound is a compound having structure I or II:
wherein R 1 and R 2 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
45. The method of claim 44 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
46. The method of claim 43 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
47. The method of claim 46 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
48. The method of claim 46 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ), dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ), diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 ), propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C 12 H 24 N 3 OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP), N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 ClN 2 OP), hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 P), diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P phenylphosphonic diamide (C 10 H 17 N 2 OP).
49. The method of claim 43 , wherein the diaryl carbonate is an activated diaryl carbonate and is bismethylsalicylcarbonate.
50. The method of claim 49 , wherein the phosphorus-containing compound is phosphorous acid.
51. The method of claim 43 , wherein the amount phosphorous-containing compound compounded with the polycarbonate and the UV stabilizer is in an amount to provide a molar ratio of phosphorus atoms to transesterification catalyst used in forming the polycarbonate (P/cat) of between 1:1 and 10:1.
52. The method of claim 51 , wherein the molar ratio is between 5:1 and 10:1.
53. A stabilized polycarbonate blend, comprising
(a) a melt polycarbonate comprising a residue from an activated diaryl carbonate,
(b) a UV stabilizer having a free -OH group, and
(c) a phosphorus-containing compound having an abstractable proton or hydrolyzable group,
wherein the phosphorous-containing compound is present in the blend in an amount sufficient to result in an increase in the retention of UV stabilizer in the blend and an increase the retention of molecular weight of the polycarbonate in the blend during a molding step, thereby improving the melt stability properties of the blend as compared to a blend formed from the same polycarbonate and UV stabilizer without the addition of the phosphorus-containing compound during a similar molding step.
54. The blend of claim 53 , wherein the phosphorus-containing compound is a compound having structure I or II:
wherein R 1 and R 2 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy,
wherein R 3 and R 4 are independently hydrogen; hydroxy, O—(NH 4 )+; OH; linear, branched or cyclic C 1 -C 36 alkyl or alkoxy; optionally substituted phenyl, aryl, phenoxy, or aryloxy.
55. The blend of claim 54 , wherein the phosphorus-containing compound is selected from the group consisting of: dimethyl phosphinic acid, dibutyl phosphinic acid, diphenyl phosphinic acid, 2-methylphenyl (phenyl) phosphinic acid, 3,5-dimethylphenyl (phenyl) phosphinic acid, 3-methoxyphenyl(phenyl)phosphinic acid, 4-methoxyphenyl(phenyl)phosphinic acid, 1-methylheptyl(phenyl)phosphinic acid, 4-ethoxyphenyl(phenyl)phosphinic acid, bis(4-methoxyphenyl)phosphinic acid, dioctylphosphinic acid, bis(2,4,4-trimethylpentyl)phosphinic acid, diammonium hydrogen phosphate, diphenyl phosphate, diphenyl phosphite, 4-(tert-pentyl)phenyl phosphate, (R)-(−)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate, and di(2-ethylhexyl) phosphate, phosphorous acid, and mono-zinc phosphate Zn(H 2 PO 4 ) 2 .
56. The blend of claim 53 , wherein the phosphorus-containing compound comprises a compound having structure III or IV:
wherein R′ is an alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x , (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 5 and R 6 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy phosphate ester or acid and phosphite ester or acid;
wherein R′ is alkoxyl, phenoxy, aryloxy or aralkyloxy, NR x (where R x is H, alkyl, aryl or aralkyl), OC(═O)R x or OP(═O)R x , and R 7 and R 8 are independently hydrogen, hydroxy; linear or cyclic C 1 -C 36 alkyl or alkoxy; phenyl, aryl, phenoxy, or aryloxy, phosphate ester or acid, and phosphite ester or acid.
57. The blend of claim 56 , wherein the phosphorus-containing compound is selected from the group consisting of: distearyl pentaerythritol diphosphite, n-butyl diphenylphosphinite, 2-phenylethyl diphenylphosphinate, 1-naphthyl diphenylphosphinate, methyl diphenylphosphinite, ethyl diphenylphosphinite, n-butyl diphenylphosphinite, methylcyclohexyl diphenylphosphinate, triphenyl phosphite, diisodecyl phenyl phosphite, tri-para-tolyl phosphate, tri-n-propyl phosphate, methyl diphenyl phosphate, tri-n-butyl phosphate triphenyl phosphate, cyclohexyl diphenyl phosphate, bis(3,5-dimethylphenyl) 4-ethylphenyl phosphate, tris(3,4-dimethylphenyl) phosphate, tris(4-tert-butylphenyl) phosphate, trans-1,4-cyclohexanediol bis(diphenyl phosphate), trisnonylphenyl phosphate, triisodecyl phosphite, tris(tridecyl) phosphate, and trilauryl phosphite.
58. The blend of claim 56 , wherein the phosphorus-containing compound is selected from the group consisting of: phosphorus pentoxide (P 4 O 10 ), pyrophosphoric acid (H 4 O 7 P 2 ), magnesium pyrophosphate (H 4 MgO 7 P 2 ,) dimethyl acid pyrophosphate (C 2 H 8 O 7 P 2 ,) diethyl acid pyrophosphate (C 4 H 12 O 7 P 2 ), potassium pyrophosphate (H 4 KO 7 P 2 ), tetraethyl diphosphate (C 8 H 20 O 7 P 2 , propylphosphonic anhydride (C 9 H 21 O 6 P 3 ), tris(N,N-tetramethylene)phosphoric acid triamide (C12H24N3OP), methylphosphonic bis(dimethylamide) (C 5 H 15 N 2 OP) N,N,N′,N′-tetramethylphosphorodiamidic chloride (C 4 H 12 ClN 2 OP) hexamethylphosphoramide (C 6 H 18 N 3 OP), 1,3-dimethyl-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine-2,4-dione (C 9 H 11 N 2 O 2 ) diphenyl 1-piperidinylphosphonate (C 17 H 20 NO 3 P), phenyl N,N,N′,N′-tetramethyldiamidophosphate (C 10 H 17 N 2 O 2 P), and N,N,N′,N′-tetramethyl-P-phenylphosphonic diamide (C 10 H 17 N 2 O 2 P).
59. The blend of claim 53 , wherein the phosphorus-containing compound is phosphorous acid.
60. The blend of claim 53 , wherein the blend further comprises a transesterification catalyst and wherein the phosphorous-containing compound is present in the blend in an amount to provide a molar ratio of phosphorus atoms to transesterification catalyst (P/cat) of between 1:1 and 10:1.
61. The blend of claim 60 , wherein the molar ratio is between 5:1 and 10:1.