Stock material or miscellaneous articles – Coated or structually defined flake – particle – cell – strand,... – Particulate matter
Reexamination Certificate
2001-03-28
2002-05-07
Acquah, Samuel A. (Department: 1711)
Stock material or miscellaneous articles
Coated or structually defined flake, particle, cell, strand,...
Particulate matter
C528S176000, C528S191000, C528S206000, C528S212000, C528S219000, C528S308000, C528S308600
Reexamination Certificate
active
06383636
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to (2,5-disubstituted-1,4-phenylene oxide) copolymers.
BACKGROUND OF THE INVENTION
Poly (2,6-disubstituted-1,4-phenylene oxide) is synthesized by oxidative polymerization of 2,6-disubstituted phenols, and it is widely known to show high heat resistance. For example, poly (2,6-dimethyl-1,4-phenylene oxide) is reported in J. Am. Chem. Soc., 81, 6335-6336 (1959), and poly (2,6-diphenyl-1,4-phenylene oxide) is reported in Macromolecules, 2, 107-108 (1969). Phenols with substituents at positions 2 and 6 are used in order to block coupling of the two ortho positions, as described in J. Polym. Sci.: Part A: Polymer Chemistry, 36, 505-517 (1998).
The inventors succeeded in synthesizing crystalline poly (2,5-dimethyl-1,4-phenylene oxide) from 2,5-dimethylphenol, which does not have a substituent at one ortho position (see Japanese Patent Application No. 2000-25621). The polymer shows a high crystalline melting point, even after melting and cooling, and it is expected to be a crystalline polymer having high heat resistance and solvent resistance. However, the mechanical properties and impact strength of molded articles made from this polymer have not been satisfactory enough, therefore further improvement is needed.
SUMMARY OF THE INVENTION
The present invention is a (2,5-disubstituted-1,4-phenylene oxide) block copolymer which comprises one or more block structural units represented by the following formula (I) and at least one structural unit represented by the following formula (II) or the following formula (III) in a molecule,
wherein R
1
represents an unsubstituted hydrocarbon group or a substituted hydrocarbon group, and the two R
1
s may be the same or different; R
2
represents an unsubstituted arylene group or a substituted arylene group; R
3
represents an unsubstituted alkylene group, a substituted alkylene group, an unsubstituted alkylene group, a substituted aralkylene group, an unsubstituted alkenylene group, a substituted alkenylene group, an unsubstituted aralkenylene group, a substituted aralkenylene group, an unsubstituted alkynylene group, a substituted alkynylene group, an unsubstituted aralkynylene group, or a substituted aralkynylene group; T represents —CO—, —CONH— or —SO
2
—; Q represents —O—, —CO—, —SO
2
—, —OCO—, —NHCO—, or —OSi(CH
3
)
2
—; a represents a number average degree of polymerization and is the number of 5 or more; and b, c, d, and e are each 1 or 0, and at least one of c, d, or e is 1.
Further the present invention is a (2,5-disubstituted-1,4-phenylene oxide) graft polymer which comprises one or more structural units represented by the following formula (IV), or three or more of structural unit of the following formula (IV) and structural unit of the following formula (V), in a molecule,
wherein R
1
represents an unsubstituted hydrocarbon group or a substituted hydrocarbon group, and the two R
1
s may be the same or different; R
4
and R
5
each represents a trifunctional unsubstituted hydrocarbon group or a trifunctional substituted hydrocarbon group; R
6
represents a hydrogen atom, a halogen atom, an unsubstituted hydrocarbon group, or a substituted hydrocarbon group; U represents —CO—, —OCO—, or —NHCO—; W represents —O—, —CO—, —CO
2
— —OCO—, or —CONH—; a represents a number average degree of polymerization and is the number of 5 or more; and f and g are each 1 or 0.
Other and further features, and advantages of the invention will appear more fully from the following description.
DETAILED DESCRIPTION OF THE INVENTION
According to the present invention, there is provided:
(1) A (2,5-disubstituted-1,4-phenylene oxide) block copolymer which comprises one or more block structural units represented by the following formula (I) and at least one structural unit represented by the following formula (II) or the following formula (III) in a molecule,
wherein R
1
represents an unsubstituted hydrocarbon group or a substituted hydrocarbon group, and the two R
1
s may be the same or different; R
2
represents an unsubstituted arylene group or a substituted arylene group; R
3
represents an unsubstituted alkylene group, a substituted alkylene group, an unsubstituted aralkylene group, a substituted aralkylene group, an unsubstituted alkenylene group, a substituted alkenylene group, an unsubstituted aralkenylene group, a substituted aralkenylene group, an unsubstituted alkynylene group, a substituted alkynylene group, an unsubstituted aralkynylene group, or a substituted aralkynylene group; T represents —CO—, —CONH— or —SO
2
—; Q represents —O—, —CO—, —SO
2
—, —OCO—, —NHCO—, or —OSi(CH
3
)
2
—; a represents a number average degree of polymerization and is the number of 5 or more; and b, c, d, and e are each 1 or 0, and at least one of c, d, or e is 1;
(2) The (2,5-disubstituted-1,4-phenylene oxide) block copolymer according to (1), wherein a in the formula (I) is 5 to 5,000, and, in a molecule, the number of the block structural units represented by the formula (I) is 1 to 1,000 and the number of the structural units represented by the formula (II) and/or the formula (III) is 1 to 1,000,000;
(3) A (2,5-disubstituted-1,4-phenylene oxide) graft polymer (homopolymer or copolymer) which comprises one or more structural units represented by the following formula (IV), or three or more of structural unit of the following formula (IV) and structural unit of the following formula (V), in a molecule,
wherein R
1
represents an unsubstituted hydrocarbon group or a substituted hydrocarbon group, and the two R
1
s may be the same or different; R
4
and R
5
each represents a trifunctional unsubstituted hydrocarbon group or a trifunctional substituted hydrocarbon group; R
6
represents a hydrogen atom, a halogen atom, an unsubstituted hydrocarbon group, or a substituted hydrocarbon group; U represents —CO—, —OCO—, or —NHCO—; W represents —O—, —CO—, —CO
2
— —OCO—, or —CONH—; a represents a number average degree of polymerization and is the number of 5 or more; and f and g are each 1 or 0;
(4) The (2,5-disubstituted-1,4-phenylene oxide) graft polymer according to (3), wherein a in the formula (IV) is 5 to 5,000, and, in a molecule, the number of the structural units represented by the formula (IV) is 1 to 100,000 and the number of the structural units represented by the formula (IV) and/or the formula (V) is 3 to 1,000,000;
(5) The (2,5-disubstituted-1,4-phenylene oxide) graft polymer according to (3) or (4), wherein f in the formula (IV) is 1;
(6) The (2,5-disubstituted-1,4-phenylene oxide) block or graft polymer according to any one of (1) to (5), wherein the polymer is a powder having an average particle diameter of 5 mm or less;
(7) The (2,5-disubstituted-1,4-phenylene oxide) block or graft polymer according to any one of (1) to (6), wherein the polymer shows an exothermic peak of crystallization of 5 J/g or more at 150° C. or more when cooled after being melted, and/or the polymer shows an endothermic peak of crystal melting of 5 J/g or more at 150° C. or more when re-heated after the melted polymer is cooled; and
(8) The (2,5-disubstituted-1,4-phenylene oxide) block or graft polymer according to any one of (1) to (7), wherein the polymer is substantially free from gel substance.
Herein, the term “a group” on a compound means to include both the group unsubstituted and the group having a further substituent thereon, unless otherwise specified.
The present invention will be described in detail hereinafter.
(1) Block Copolymer
The (2,5-disubstituted-1,4-phenylene oxide) block copolymer in the present invention means a polymer which comprises one or more block structural units represented by the above-mentioned formula (I) and one or more structural units represented by the above-mentioned formula (II) and/or the above-mentioned formula (III) in a molecule.
The unsubstituted hydrocarbon group as R
1
in the above-mentioned formula (I) is preferably an alkyl group with 1 to 30 (more preferably 1 to 20) carbon atoms, an aralkyl group with 7 to 30 (more preferably 7 to 20) carbon atoms, or an aryl group with 6 to 30 (m
Higashimura Hideyuki
Kobayashi Shiro
Namekawa Shuhei
Acquah Samuel A.
Birch & Stewart Kolasch & Birch, LLP
Director-General of National Institute of Advanced Industrial Sc
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