Process for producing (co)polycarbonate and (co)polycarbonate composition

• US 5,387,628 A
• Filed: 09/09/1993
• Issued: 02/07/1995
• Est. Priority Date: 03/11/1992
• Status: Expired due to Fees

• Current Assignee: Daicel Chemical Industries Limited
• Original Assignee: Daicel Chemical Industries Limited
• Inventors: Fukuda, Yutaka, Matsumoto, Toshihiro, Kanno, Tatsuya, Oshino, Yasuhiro, Kuwana, Takaaki, Yamato, Tsutomu, Iguchi, Yoshihiro
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US08/119,368
• Time in Patent Office: 516 Days
• Field of Search: 524/117, 524/119, 524/120, 524/126, 524/130, 524/132, 524/133, 524/135, 524/601, 524/611, 524/710
• US Class Current: 524/117
• CPC Class Codes: C08G 63/64 Polyesters containing both carboxylic ester groups and carbonate groups
• CPC Class Codes: C08G 64/307 and phenols
• CPC Class Codes: C08K 5/524 Esters of phosphorous acids, e.g. of H3PO3
• CPC Class Codes: C08L 69/00 Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Abstract

A process for producing a (co)polycarbonate or a (co)polyestercarbonate having a high molecular weight and excellent hue, heat stability and mechanical properties by reacting a dihydroxyl compound with a diester of carbonic acid and/or a diester of dicarbonic acid in the presence of a transesterification catalyst, wherein at least part of the reaction process is conducted in the presence of a specified organic phosphorus compound, or, in the presence of a specified organic phosphorus compound and a hindered phenol compound. A (co)polycarbonate or (co)polyester-carbonate composition having excellent hue, heat stability and mechanical properties, comprising a (co)polycarbonate and/or a (co)polyestercarbonate and, a specified organic phosphorus compound, or, a specified organic phosphorus compound and a hindered phenol compound.

Claims

1. A melt polycondensation process for producing a (co)polycarbonate composition or a (co)polyestercarbonate composition comprising adding an organic phosphorus compound selected from the group consisting of compounds represented by the following general formulas ( 1) to (6), or, an organic phosphorus compound selected from the group consisting of compounds represented by the following general formulas (1) to (6) and a hindered phenol compound to a (co)polycarbonate or a (co)polyestercarbonate, said (co)polycarbonate and said (co)polyestercarbonate being obtained by reacting an aromatic dihydroxy compound with one or more members selected from the group consisting of a diester of carbonic acid and a diester of dicarboxylic acid:

##STR44## wherein R^a, R^b and R^c each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which is unsubstituted or substituted;

##STR45## wherein R^d, R^e, R^f, R^g, R^h, Rⁱ, R^j and R^k each represents a hydrogen atom or a straight-chain or branched alkyl group having 1 to 12 carbon atoms, R^q and R^r each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms and R^s and R^t each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms;

##STR46## wherein R^u and R^v each represents a straight-chain or branched alkyl group having 1 to 20 carbon atoms and R^w represents a phenyl or aralkyl group which is unsubstituted or substituted.

2. The process according to claim 1, wherein the organic phosphorus compound is one member selected from the group consisting of triethyl phosphite, triisopropyl phosphite, triisodecyl phosphite, tridodecyl phosphite, phenyl diisodecyl phosphite, diphenyl isodecyl phosphite, triphenyl phosphite, phenyl bis(4-nonylphenyl) phosphite, tris(4-octylphenyl) phosphite, tris(4-(1-phenylethyl)phenyl) phosphite, tris(2,4-di-tert-butylphenyl) phosphite, tris(4-nonylphenyl) phosphite, diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphonate, tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-biphenylene diphosphite of the following formula:

##STR47## pentaerythritol di[(2,6-di-tert-butyl-4-methylphenyl) phosphite] of the following formula;

##STR48## pentaerythritol di[(2,4-di-tert-butylphenyl) phosphite] of the following formula;

##STR49## tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-(2,2-diphenylpropane) phosphite of the following formula;

##STR50## dialkoxyphenylphosphoric acids of the following formula;

##STR51## wherein R^u and R^v each represent a straight-chain or branched alkyl group having 1 to 20 carbon atoms and Ph represents a phenyl group,

and the phosphonite compound of the following formula;

##STR52##

3. The process according to claim 1, wherein the organic phosphorus compound is one number selected from the group consisting of tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-biphenylene diphosphite of the following formula:

##STR53## tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-(2,2-diphenylpropane) phosphite of the following formula;

##STR54## and dialkoxyphenylphosphoric acids of the following formula;

##STR55## wherein R^u and R^v each represent a straight-chain or branched alkyl group having 1 to 20 carbon atoms and Ph represents a phenyl group.

4. The process according to claim 1, wherein the hindered phenol compound is one member selected from the group consisting of octadecyl propionate-3-(3,5-di-t-butyl-4-hydroxyphenyl), N,N'"'"'-hexamethylene-bis(3,5-di-t-butyl-4-hydroxyhydrocinnamamide), triethylene glycol bis[3-(3-t-butyl-5-methyl-4hydroxyphenyl)propionate], 1,6-hexanediol-bis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-t-butyl-4-hydroxybenzyl phosphonate-diethyl ester, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene and compounds of the following formulas:

##STR56##

5. The process according to claim 1, wherein the hindered phenol compound is one member selected from the group consisting of N,N'"'"'-hexamethylene-bis(3,5-di-t-butyl-4-hydroxyhydrocinnamamide), triethylene glycol bis[3(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-t-butyl-4-hydroxybenzyl phosphonate-diethyl ester and compounds of the following formulas:

##STR57##

6. The process according to claim 1, wherein the reacting of said aromatic dihydroxy compound with one or more members selected from the group consisting of a diester of carbonic acid and a diester of dicarboxylic acid is conducted in the presence of a transesterification catalyst.

7. The process according to claim 6, wherein the transesterification catalyst is a basic compound containing a nitrogen atom in the molecule.

8. The process according to claim 7, wherein the basic compound is one member selected from the group consisting of aliphatic primary amines, aliphatic secondary amines, aliphatic tertiary amines, alicyclic primary amines, alicyclic secondary amines, alicyclic tertiary amines, aromatic primary amines, aromatic secondary amines, aromatic tertiary amines, quaternary ammonium salts and ammonia.

9. The process according to claim 7, wherein the basic compound is one member selected from the group consisting of ammonia, ammonium hydroxide compounds, ammonium borohydride compounds, ammonium tetraarylborates, pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidines, quinolines, pyrazoles, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

10. The process according to claim 7, wherein the basic compound is one member selected from the group consisting of pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

11. The process according to claim 7, wherein the basic compound is 4-dimethylaminopyridine or 4-pyrrolidinopyridine.

12. The process according to claim 6, wherein the transesterification catalyst is a basic compound containing a nitrogen atom in the molecule, and one or more members selected from the group consisting of an alkaline metal compound and an alkaline earth metal compound.

13. The process according to claim 12, wherein the basic compound is one member selected from the group consisting of aliphatic primary amines, aliphatic secondary amines, aliphatic tertiary amines, alicyclic primary amines, alicyclic secondary amines, alicyclic tertiary amines, aromatic primary amines, aromatic secondary amines, aromatic tertiary amines, quaternary ammonium salts and ammonia.

14. The process according to claim 12, wherein the basic compound is one member selected from the group consisting of ammonia, ammonium hydroxide compounds, ammonium borohydride compounds, ammonium tetraarylborates, pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds, and piperadine compounds.

15. The process according to claim 12, wherein the basic compound is one member selected from the group consisting of pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

16. The process according to claim 12, wherein the basic compound is 4-dimethylaminopyridine or 4-pyrrolidinopyridine.

17. The process according to claim 12, wherein the alkaline metal compound is one member selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium hydrogencarbonate, potassium hydrogencarbonate, lithium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium carbonate, sodium acetate, potassium acetate, lithium acetate, sodium stearate, potassium stearate, lithium stearate, sodium borohydride, lithium borohydride, potassium borohydride, sodium tetraphenylborate, sodium benzoate, potassium benzoate, lithium benzoate, disodium hydrogenphosphate, dipotassium hydrogenphosphate, dilithium hydrogenphosphate, disodium, dipotassium or dilithium salt of bisphenol A, and sodium, potassium or lithium salt of phenol.

18. The process according to claim 12, wherein the alkaline earth metal compound is one member selected from the group consisting of calcium hydroxide, barium hydroxide, magnesium hydroxide. strontium hydroxide, calcium hydrogencarbonate, barium hydrogencarbonate, magnesium hydrogencarbonate, strontium hydrogencarbonate, calcium carbonate, barium carbonate, magnesium carbonate, strontium carbonate, calcium carbonate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate and strontium stearate.

19. A (co)polycarbonate or a (co)polyestercarbonate composition comprising one or more members selected from the group consisting of a (co)polycarbonate and a (co)polyestercarbonate, said (co)polycarbonate and said (co)polyestercarbonate being obtained by reacting an aromatic dihydroxy compound with one or more members selected from the group consisting of a diester of carbonic acid and a diester of dicarboxylic acid, and an organic phosphorus compound selected from the group consisting of compounds represented by the following general formulas (1) to (6), or, an organic phosphorus compound selected from the group consisting of compounds represented by the following general formulas (1) to (6) and hindered phenol compound:

##STR58## wherein R^a, R^b and R^c each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group which is unsubstituted or substituted;

##STR59## wherein R^d, R^e, R^f, R^g, R^h, Rⁱ, R^j and R^k each represents a hydrogen atom or a straight-chain or branched alkyl group having 1 to 12 carbon atoms, R^q and R^r each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms and R^s and R^t each represents a straight-chain or branched alkyl group having 1 to 12 carbon atoms;

##STR60## wherein R^u and R^v each represents a straight-chain or branched alkyl group having 1 to 20 carbon atoms and R^w represents a phenyl or aralkyl group which is unsubstituted or substituted.

20. The composition according to claim 19, wherein the organic phosphorus compound is one member selected from the group consisting of triethyl phosphite, triisopropyl phosphite, triisodecyl phosphite, tridodecyl phosphite, phenyl diisodecyl phosphite, diphenyl isodecyl phosphite, triphenyl phosphite, phenyl bis(4-nonylphenyl) phosphite, tris(4-octylphenyl) phosphite, tris(4-(1-phenylethyl)phenyl) phosphite, tris(2,4-di-tert-butylphenyl) phosphite, tris (4-nonylphenyl) phosphite, diethyl 3,5-di-tert-4-hydroxybenzyl phosphonate, tetrakis-(2,4-di-tert-butylphenyl)-4,4'"'"'-biphenylene diphosphite of the following formula:

##STR61## pentaerythritol di[(2,6-di-tert-butyl-4-methylphenyl) phosphite] of the following formula;

##STR62## pentaerythritol di[(2,4-di-tert-butylphenyl) phosphite] of the following formula;

##STR63## tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-(2,2diphenylpropane) phosphite of the following formula;

##STR64## dialkoxyphenylphosphoric acids of the following formula;

##STR65## wherein R^u and R^v each represent a straight-chain or branched alkyl group having 1 to 20 carbon atoms and Ph represents a phenyl group,

and the phosphonite compound of the following formula;

##STR66##

21. The composition according to claim 19, wherein the organic phosphorus compound is one member selected from the group consisting of tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-biphenylene diphosphite of the following formula:

##STR67## tetrakis(2,4-di-tert-butylphenyl)-4,4'"'"'-(2,2-diphenylpropane) phosphite of the following formula;

##STR68## and dialkoxyphenylphosphoric acids of the following formula;

##STR69## wherein R^u and R^v each represent a straight-chain or branched alkyl group having 1 to 20 carbon atoms and Ph represents a phenyl group.

22. The composition according to claim 19, wherein the hindered phenol compound is one member selected from the group consisting of octadecyl propionate-3-(3,5-di-t-butyl-4-hydroxyphenyl), N,N'"'"'-hexamethylene-bis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), triethylene glycol bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], pentaerythrityl tetrakis[3(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-t-butyl-4-hydroxybenzyl phosphonate-diethyl ester, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene and compounds of the following formulas:

##STR70##

23. The composition according to claim 19, wherein the hindered phenol compound is one member selected from the group consisting of N,N'"'"'-hexamethylene-bis(3,5-di-t-butyl-4-hydroxyhydrocinnamamide), triethylene glycol bis[3-(3-t-butyl-5methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis [3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-t-butyl-4-hydroxybenzyl phosphonate-diethyl ester and compounds of the following formulas:

##STR71##

24. The composition according to claim 19, wherein the (co)polycarbonate or the (co)polyestercarbonate is obtained by reacting a dihydroxyl compound with one or more members selected from the group consisting of a diester of carbonic acid and a diester of dicarbonic acid in the presence of a transesterification catalyst.

25. The composition according to claim 24, wherein the transesterification catalyst is a basic compound containing a nitrogen atom in the molecule.

26. The composition according to claim 25, wherein the basic compound is one member selected from the group consisting of aliphatic primary amines, aliphatic secondary amines, aliphatic tertiary amines, alicyclic primary amines, alicyclic secondary amines, alicyclic tertiary amines, aromatic primary amines, aromatic secondary amines, aromatic tertiary amines, quaternary ammonium salts and ammonia.

27. The composition according to claim 25, wherein the basic compound is one member selected from the group consisting of ammonia, ammonium hydroxide compounds, ammonium borohydride compounds, ammonium tetraarylborates, pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidines, quinolines, pyrazoles, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

28. The composition to claim 25, wherein the basic compound is one member selected from the group consisting of pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

29. The composition according to claim 25, wherein the basic compound is 4-dimethylaminopyridine or 4-pyrrolidinopyridine.

30. The composition according to claim 24, wherein the transesterification catalyst is a basic compound containing a nitrogen atom in the molecule, and one or more members selected from the group consisting of an alkaline metal compound and an alkaline earth metal compound.

31. The composition according to claim 30, wherein the basic compound is one member selected from the group consisting of aliphatic primary amines, aliphatic secondary amines, aliphatic tertiary amines, alicyclic primary amines, alicyclic secondary amines, alicyclic tertiary amines, aromatic primary amines, aromatic secondary amines, aromatic tertiary amines, quaternary ammonium salts and ammonia.

32. The composition according to claim 30, wherein the basic compound is one member selected from the group consisting of ammonia, ammonium hydroxide compounds, ammonium borohydride compounds, ammonium tetraarylborates, pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

33. The composition according to claim 30, wherein the basic compound is one member selected from the group consisting of pyridine compounds, imidazole compounds, diazo compounds, picoline compounds, pyrimidine compounds, quinoline compounds, pyrazole compounds, aniline, pyrrolidine compounds, morpholine compounds, piperidine compounds and piperadine compounds.

34. The composition according to claim 30, wherein the basic compound is 4-dimethylaminopyridine or 4-pyrrolidinopyridine.

35. The composition according to claim 30, wherein the alkaline metal compound is one member selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium hydrogencarbonate, potassium hydrogencarbonate, lithium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium carbonate, sodium acetate, potassium acetate, lithium acetate, sodium stearate, potassium stearate, lithium stearate, sodium borohydride, lithium borohydride, potassium borohydride, sodium tetraphenylborate, sodium benzoate, potassium benzoate, lithium benzoate, disodium hydrogenphosphate, dipotassium hydrogenphosphate, dilithium hydrogenphosphate, disodium, dipotassium or dilithium salt of bisphenol A, and sodium, potassium or lithium salt of phenol.

36. The composition according to claim 30, wherein the alkaline earth metal compound is one member selected from the group consisting of calcium hydroxide, barium hydroxide, magnesium hydroxide, strontium hydroxide, calcium hydrogencarbonate, barium hydrogencarbonate, magnesium hydrogencarbonate, strontium hydrogencarbonate, calcium carbonate, barium carbonate, magnesium carbonate, strontium carbonate, calcium carbonate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate and strontium stearate, an organic phosphorus compound or an organic phosphorus compound and a hindered phenol compound.

37. The composition according to claim 19, wherein the (co)polycarbonate is obtained by the phosgene method.

38. The composition according to claim 19, wherein the (co)polycarbonate has terminal hydroxyl group content of 3 to less than 50 molar

39. The composition according to claim 19, wherein the (co)polycarbonate has terminal hydroxyl group content of 50 to 80 molar % and the composition further contains a polymer other than (co)polycarbonates and (co)polyestercarbonates.