Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2000-02-01
2003-04-01
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S086000, C528S482000, C528S485000, C528S486000, C528S492000
Reexamination Certificate
active
06541596
ABSTRACT:
TECHNICAL FIELD
This invention relates to a novel crystallizable poly(2,5-di-substituted-1,4-phenylene oxide), and also to a method of preparing the same.
BACKGROUND OF THE INVENTION
As is well known in the art, poly(2,6-di-substituted-1,4-phenylene oxide)s are prepared by oxidative polymerization of 2,6-di-substituted phenols, and they exhibit high heat resistance. For instance, there are reported poly(2,6-dimethyl-1,4-phenylene oxide), in J. Am. Chem. Soc. 81, 6335-6336 (1959), and poly(2,6-diphenyl-1,4-phenylene oxide), in Macromolecules, 2, 107-108 (1969). The reason to use phenols having substituents at the 2 and 6 positions is that coupling at the two ortho positions is blocked, as is set out in J. Polym. Sci.: Part A: Polymer Chemistry, 36, 505-517 (1998).
On the other hand, with respect to the oxidative polymerization of 2,5-di-substituted phenols, which have no substituent at one of the ortho positions, there are reported a method using a copper/tetramethylethylene-diamine catalyst, in Ecletica Quim., 18 93-100 (1993); a method using a copper/dimethylpyridine catalyst, in Polymer, 20(8), 995-1002 (1979); a method using a copper/monoalkylamine catalyst, in Chem. Prum., 22(9), 451-454 (1972); a method using a copper/dialkylamine catalyst, in Polimery, 14(11), 535-538 (1969); a method using a manganese/alkoxide catalyst, in JP-B-47-619 (“JP-B” means examined Japanese Patent Publication); a method using a basic copper/pyridine catalyst, in JP-B-50-28999; and a method using a manganese/salicylaldehydeimine, in JP-B-48-20239.
However, the polymers obtained according to the methods using these catalysts are not crystallized after having once been melted. In general, it is known that, when a polymer is crystallized after melting, the heat resistance of the melt molding is kept to a level of its crystal melting point, and the solvent resistance is improved. Accordingly, since the polymers obtained by use of the known catalysts are not crystallized after melting, there arises the problem that the inherent heat resistance and solvent resistance cannot be fully developed. Presumably, this is because, with the prior art catalysts, side reactions, such as a coupling reaction at the ortho positions, an oxygenation reaction, and the like, cannot be suppressed to a satisfactory extent, so that the resultant polymer contains, in large amounts, various structures other than the 1,4-phenylene oxide structure.
SUMMARY OF THE INVENTION
Accordingly, an object of the invention is to provide a novel crystallizable poly(2,5-di-substituted-1,4-phenylene oxide).
Another object of the invention is to provide a method of preparing such a crystallizable poly(2,5-di-substituted-1,4-phenylene oxide).
Other and further objects, features, and advantages of the invention will appear more fully from the following description, taken in connection with the accompanying drawings.
REFERENCES:
patent: 5037897 (1991-08-01), Glans et al.
patent: 5334444 (1994-08-01), Bhoori et al.
patent: 1451695 (1976-10-01), None
patent: B-47-619 (1972-01-01), None
patent: 4820239 (1973-06-01), None
patent: 4838640 (1973-11-01), None
patent: 5028999 (1975-09-01), None
patent: 62172024 (1987-07-01), None
patent: 1045899 (1998-02-01), None
patent: 1045904 (1998-02-01), None
Preprint read on Oct. 8, 1999 at the 48thSymposium on Macromolecules (a symposium held by Society of Polymer Science, Japan), under the lecture No. IIIB12, entitled “Radical-Controlled” Oxidative Polymerization of Phenols.
Polymer Preprints2000, 41(1) XXXX, Radical-Controlled Oxidative Polymerization of Phenols.
Preprint read on Oct. 8, 1999 at the 48thSymposium on Macromolecules (a symposium held by Society of Polymer Science, Japan), under the lecture No. IIIB13, entitled Oxidative Polymerization of 2,5-Dimethylphenol Catalyzed by Tyrosinase-Model Complex.
Polymer Preprints2000, 41(1) XXXX, Oxidative Polymerization of 2,5-Dimethylphenol Catalyzed by Tyrosinase-Model Complex.
J. Am. Chem. Soc., 1998, 120, 8529-8530.
Polymer, 20(8), 995-1002 (1979).
Ecletica Quim., 18, 93-100 (1993).
Chem. Prum., 22(9), 451-454 (1972).
Polimery, 14(11), 535-538 (1969).
J. Am. Chem. Soc., 81, 6335-6336 (1959).
Macromolecules, 2, 107-108 (1969).
J. Polym. Sci.: Part A: Polymer Chemistry, 36, 505-517 (1998).
J. Jachowicz et al., Thermal degradation of poly(2-methylphenylene oxide), poly(2,5-dimethylphenylene oxide) and poly (1,4-phenylene oxide), Polymer, vol. 20, pp. 995-1001, XP-000949236, Aug., 1979.
Jan Kotas et al., “Kinetika oxidaeni polykondenzace krezolu a xylenolu”, CHEMICKY PRUMYSL, vol. 22, No. 9, pp. 451-454, XP-000949385, 1972.
Hideyuki Hiashimura et al., “Highly Regioselective Oxidative Polymerization of 4-Phenoxyphenol to Poly(1,4-phenylene oxide) Catalyzed by Tyrosinase Model Complexes”, J.Am.Chem.Soc., vol. 120, pp. 8529-8530, XP-000946155, 1998.
Hideyuki Higashimura et al.; Applied Catalysis A: General; “‘Radical—controlled’ oxidative polymerization of o-cresol catalyzed by &mgr;-&eegr;2:&eegr;2-peroxo dicopper (II) complex”; 194-195 (2000) 427-433.
Hideyuki Higashimura et al., Journal of Molecular Catalysts A: Chemical “‘Radical-controlled’ oxidative polymerization of m-cresol catalyzed by &mgr;&eegr;2:&eegr;2-peroxo dicopper (II) comples”; 155 (2000) 201-207.
Encycl. Polym. Sci. Technol., 10:92-111 (1969).
Fujisawa Kiyoshi
Higashimura Hideyuki
Kobayashi Shiro
Moro-oka Yoshihiko
Secretary of Agency of Industrial Science and Technology
Truong Duc
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