Silcon-containing polymers

Details Silcon-containing polymers Silcon-containing polymers

2002-08-06

2004-06-22

Davis, Brian (Department: 1621)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C528S029000, C528S031000, C556S443000, C556S470000

Reexamination Certificate

active

06753401

ABSTRACT:

TECHNICAL FIELD
This invention is directed to a silicon-containing polymer and to a process for the preparation thereof.
BACKGROUND ART
Various types of silicon-containing polymers are hitherto known. Among them, a silicon-containing polymer having recurring structural units represented by the following formula (a):
wherein Ar represents an arylene group and R
1
and R
2
each represent a substituent such as an aryl group, an alkoxy group or an alkyl group, is excellent in resistance to heat and is studied for use as an aerospace material (J. Appl. Polym. Sci., 9, 295(1965); J. Polym. Sci., A, Polym. Chem., 32, 131(1994)).
The silicon-containing polymer having the recurring structural units represented by the above formula (a) is produced by polycondensation of hydroquinone with a di-substituted silane or dehydrogenative polymerization of quinone with di-substituted silane.
It is an object of the present invention to provide a novel silicon-containing polymer having a main chain which comprises organic groups, oxygen atoms and silicon atoms.
Another object of the present invention is to provide an industrially advantageous process for the production of a silicon-containing polymer having a main chain which comprises organic groups, oxygen atoms and silicon atoms.
DISCLOSURE OF THE INVENTION
In accordance with the present invention there is provided a silicon-containing polymer represented by the following general formula (1);
wherein Ar represents an arylene group which may have a substituent, R represents a hydrocarbyl group which may have a substituent and n is a number average polymerization degree of 2-5,000.
The present invention also provides a process for the production of a silicon-containing polymer represented by the above general formula (1), characterized in that at least one compound selected from quinone and aromatic diols and at least one trihydrosilane represented by the following general formula (3):
wherein R represents a hydrocarbyl group which may have a substituent, are subjected to dehydrogenative polymerization in the presence of a palladium-containing catalyst.
The present invention further provides a process for the production of a silicon-containing polymer represented by the following general formula (2):
wherein A represents an aralkylene group which may have a substituent or an alkylene group which may have a substituent, R
1
and R
2
each represent a hydrocarbyl group which may have a substituent but one of R
1
and R
2
is an aryl group and n is a number average polymerization degree of 2-5,000, characterized in that at least one diol represented by the following general formula (4):
HO—A—OH  (4)
wherein A represents an aralkylene group which may have a substituent or an alkylene group which may have a substituent and at least one dihydrosilane represented by the following general formula (5):
wherein R
1
and R
2
each represent a hydrocarbyl group which may have a substituent but one of R
1
and R
2
is an aryl group, are subjected to dehydrogenative polymerization in the presence of a palladium-containing catalyst.
The present invention further provides a process for the production of a silicon-containing polymer represented by the following general formula (6):
wherein Y represents a divalent hydrocarbyl group which may have a substituent, R
3
and R
4
each represent a hydrocarbyl group which may have a substituent and n is a number average polymerization degree of 2-5,000, characterized in that at least one diol represented by the following general formula (7):
HO—Y—OH  (7)
wherein Y represents a hydrocarbyl group which may have a substituent and at least one dihydrosilane represented by the following general formula (8):
wherein R
3
and R
4
each represent a hydrocarbyl group which may have a substituent, are subjected to dehydrogenative polymerization in the presence of a palladium-containing catalyst.
BEST MODE FOR CARRYING OUT THE INVENTION
In the above general formula (1), Ar represents an arylene group which may have a substituent. The arylene group has 6-18 carbon atoms, preferably 6-12 carbon atoms. The arylene group may be phenylene or naphthylene. The substituent may be a halogen atom (chlorine, bromine, iodine or fluorine), a cyano group, an alkoxy group, an aryloxy group, etc. Specific examples of the arylene group include various 1,4-phenylenes and 1,4-naphthylenes such as 1,4-phenylene, 1,4-naphthylene, 2-t-butyl-1,4-phenylene, phenyl-1,4-phenylene, 2,5-dimethyl-1,4-phenylene, 2,3,5,6-tetramethyl-1,4-phenylene, 2,5-dichloro-1,4-phenylene, 2,3,5,6-tetrachloro-1,4-phenylene and 2,3-dichloro-5,6-dicyano-1,4-phenylene.
In the above general formula (1), R represents a hydrocarbyl group. The hydrocarbyl group has 1-18 carbon atoms, preferably 1-12 carbon atoms. The hydrocarbyl group may be an alkyl group having 1-18 carbon atoms, preferably 1-12 carbon atoms, a cycloalkyl group having 4-10 carbon atoms, preferably 6-8 carbon atoms, an aryl group having 6-18 carbon atoms, preferably 6-12 carbon atoms or an aralkyl group having 7-17 carbon atoms, preferably 7-11 carbon atoms. The hydrocarbyl group may have a substituent such as a halogen atom, a cyano group, an alkoxy group or an aryloxy group. Examples of the hydrocarbyl group include phenyl, p-tolyl, m-tolyl, p-anisyl, p-chlorophenyl, p-fluorophenyl, p-trifluoromethylphenyl, p-cyanophenyl, methyl, ethyl, isopropyl, sec-butyl, hexyl and benzyl.
In the above general formula (1), n represents a number-average polymerization degree and is 2-5,000, especially 5-1,000.
The silicon-containing polymer of the above general formula (1) may be produced by subjecting at least one compound selected from quinone and aromatic diols and at least one trihydrosilane represented by the above general formula (3) to dehydrogenative polymerization in the presence of a palladium-containing catalyst.
The quinone includes various benzoquinones and naphthoquinones. Examples of quinone include 1,4-quinones such as 1,4-benzoquinone, 1,4-naphthoquinone, 2-t-butyl-1,4-benzoquinone, phenyl-1,4-benzoquinone, 2,5-dimethyl-1,4-benzoquinone, 2,3,5,6-tetramethyl-1,4-benzoquinone, 2,5-dichloro-1,4-benzoquinone, 2,3,5,6-tetrachloro-1,4-benzoquinone and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
The aromatic diol is not specifically limited but is preferably hydroquinone or resorcinol. Examples of hydroquinone and resorcinol include hydroquinone, methylhydroquinone, t-butylhydroquinone, chlorohydroquinone, 2-methoxyhydroquinone, phenylhydroquinone, 2,3-dimethylhydroquinone, 2,3,5,6-tetramethylhydroquinone, 2,3,5,6-tetrachlorohydroquinone, resorcinol, 2-methylresorcinol, 4-hexylresorcinol, 5-phenylresorcinol and 1,4-dihydroxynaphthalene.
The above-mentioned trihydrosilane is not specifically limited. Examples of trihydrosilane include phenylsilane, p-tolylsilane, m-tolylsilane, p-anisylsilane, p-chlorophenylsilane, p-fluorophenylsilane, p-trifluoromethylphenylsilane, p-cyanophenylsilane, methylsilane, ethylsilane, isopropylsilane, sec-butylsilane, hexylsilane and benzylsilane.
The palladium-containing catalyst for use in the present invention may be various kinds of conventionally known catalysts. A palladium complex having a tri-substituted phosphine ligand is preferably used. The substituent may be an alkyl group having 1-12 carbon atoms, preferably 1-6 carbon atoms, a cycloalkyl group having 4-10 carbon atoms, preferably 6-8 carbon atoms, an aryl group having 6-12 carbon atoms, preferably 6-10 carbon atoms, an aralkyl group having 7-11 carbon atoms, preferably 7-9 carbon atoms. Examples of the palladium-containing catalyst include bis(triphenylphosphine)dichloropalladium, bis(triethylphosphine)dichloropalladium, bis(tricyclohexylphosphine)palladium, tetrakis(triphenylphosphine)palladium, tris(triethylphosphine)palladium, (tetramethylethylenediamine)dichloropalladium, allylpalladiumchloride dimer, bis(benzonitrile)dichloropalladium, (1,5-cyclooctadiene)dichloropalladium, tris(dibenzylideneacetone)dipalladium, bis(acetylacetonate)palladium, palladium acetate, palladium chloride and palladium

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