Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-07-11
2004-11-09
Mulcahy, Peter D. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S360000, C524S370000, C524S371000
Reexamination Certificate
active
06815481
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a polybutadiene composition. More particularly, it relates to a polybutadiene composition in which the thermal degradation under an air free environment is prevented.
Polybutadiene type polymers having butadiene units as their polymerization unit have been widely used as various molded articles, since they exhibit same strength and elastic property as vulcanized elastomers and same thermo plastic property as thermoplastic resins. However, polybutadiene type polymers are apt to deteriorate by heat and to generate cross-linked products (gelled product) under heating. Such cross-linked products cause bad appearance of the molded article obtained by molding the polybutadiene type polymer. Particularly, when the molded article is a film, the cross-linked products lower the strength of the article.
For preventing such thermal degradation, a polybutadiene composition comprising a polybutadiene type polymer and an antioxidant is proposed. (JP-A-1-182308, etc.)
However, thermal degradation of such a conventional polybutadiene composition is not sufficiently prevented when the composition is heated under an air-free environment such as the inner part of an extruder.
The present inventors have conducted extensive studies to develop a polybutadiene composition which does not deteriorate by heating even under an air-free environment. As a results they have found that a polybutadiene composition comprising a specific compound does not deteriorate by heating even under an air-free environment. Thus, the present invention was completed.
The present invention provides a polybutadiene composition comprising a polybutadiene type polymer and a compound represented by the following formula (I):
wherein Ar
1
and Ar
2
each independently represent an aromatic ring, X and Y each independently represent an alkylene group having one or two carbon atoms, an oxygen atom or a carbonyl group. (Hereinafter, this compound is referred to as “Compound (I)”.)
The polybutadiene type polymer comprised in a polybutadiene composition of the present invention is a polymer having a polymerization unit derived from butadiene. Examples of the polybutadiene type polymers include polybutadiene, styrene-butadiene copolymers, acrylonitrile-butadiene copolymers, acrylonitrile-butadiene-styrene copolymers, styrene-butadiene block copolymers, and impact resistant polystyrenes. The polybutadiene type polymer may be either a rubber or a resin. Polybutadiene may be either a polybutadiene rubber produced by a solution polymerization or a polybutadiene rubber produced by a emulsion polymerization, The impact resistant polystyrene is a polystyrene modified with a polybutadiene rubber, a styrene-butadiene copolymer rubber or the like to suppress occurrence of cracks caused by an impact. Such polybutadiene type polymers can be produced, for example, by a solution polymerization method, emulsion polymerization method, decomposition of polymer, or the like. The polybutadiene type polymer may be used alone or as a mixture of two or more.
Examples of the aromatic ring represented by Ar
1
or Ar
2
in the formula (I) include a benzene ring and naphthalene ring.
X and Y in the formula (I) are divalent residues. X and Y, which are same to or different from each other, represent an alkylene group having one or two carbon atoms, an oxygen atom or a carbonyl group. The alkylene group having one or two carbon atoms may be, for example, a methylene group, dimethylene group. The alkylene group may also be a substituted alkylene group, where the hydrogen atom is substituted with another atom or a group. It is preferred that at least one of X and Y is an alkylene group having one or two carbon atoms, and it is more preferred that both of X and Y are alkylene groups having one or two carbon atoms.
Each of X or Y bonds to a carbon atom in Ar
1
in the formula (I), and a carbon atom in Ar
2
in the formula (I). The two carbon atoms in Ar
1
or Ar
2
bonding to X or Y are usually adjacent to each other.
The aromatic ring represented by Ar
1
or Ar
2
may be substituted with one or more substituents. Examples of the substituents include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxyl group, an acyloxy, a hydroxyl group, a halogen atom, a sulfo group (which is SO
3
H) and carboxyl group.
Examples of the alkyl group as the substituent on Ar
1
or Ar
2
include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl. 1-methylhexyl, n-heptyl, 1-methylheptyl, 3-methylheptyl, n-octyl, t-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methyundecyl, dodecyl, 1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl and docosyl.
Preferably, the alkyl group is an alkyl group having one to 6 carbon atoms. The hydrogen atom(s) therein may be optionally substituted with another atom or a group.
As the cycloalkyl group as the substituent on Ar
1
or Ar
2
, a cycloalkyl group having 5 to 8 carbon atoms can be exemplified. Specific examples thereof include cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cycloheptyl and cyclooctyl. The hydrogen atom in such a cycloalkyl group may be optionally substituted with another atom or a group.
As the aryl group as the substituent on Ar
1
or Ar
2
, an aryl group having 6 to 20 carbon atoms can be exemplified. Specific examples thereof include phenyl, o-tolyl, p-tolyl, 2,3-xylyl, 2,4-xylyl, 2,5-xylyl, mesityl, naphthyl and anthryl. The hydrogen atom in such an aryl group may be optionally substituted with another atom or a group.
As the aralkyl group as the substituent on Ar
1
or Ar
2
, an aralkyl group having 7 to 20 carbon atoms can be exemplified. Specific examples thereof include benzyl, phenylmethyl, methylbenzyl and naphthyl methyl. The hydrogen atom in such an aralkyl group may be optionally substituted with another atom or a group.
As the alkoxyl group as the substituent on Ar
1
or Ar
2
, an alkoxyl group having 1 to 18 carbon atoms can be exemplified. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, pentyloxy and octadecyloxy. The hydrogen atom in such an alkoxyl group may be optionally substituted with another atom or a group.
As the acyloxyl group as the substituent on Ar
1
or Ar
2
, an acyloxyl group having 1 to 18 carbon atoms can be exemplified, Specific examples thereof include acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy and stearyloxy. The hydrogen atom in such an acyloxyl group may be optionally substituted with another atom or a group.
As the halogen atom as the substituent on Ar
1
or Ar
2
, a fluorine atom, a chlorine atom and a bromine atom can be exemplified.
When Ar
1
and Ar
2
are benzene rings, the compound represented by the formula (I) is a compound represented by the following formula (I-1):
wherein m and n each independently represent an integer of 0-4, R represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxyl group, an acyloxy group, a hydroxyl group, a halogen atom, a sulfo group and a carboxyl group, provided that, when sum of m and n is two or more, the groups of R may be same to or different from each other.
Examples of the compounds represented by the formula (I) include:
xanthene,
2,7-dimethylxanthene,
3,6-dimethylxanthene,
4,5-dimethylxanthene,
1,8-dimethyl-4,5-diisopropylxanthene,
9-phenylxanthene,
2-benzylxanthene,
9-benzylxanthene,
9-p-torylxanthene,
2,7-dimethyl-9-phenylxanthene,
9-hydroxylxanthene,
9-carboxylxanthene,
9-methoxylcarbonylxanthene,
9-methyl-9H-xanthene-2,7-diol,
9-ethyl-9H-xanthene-2,7-diol,
9-isopropyl-9H-xanthene-2,7-diol,
9-phenyl-9H-xanthene-2,7-diol,
3,4,5,6-tetramethyl-9H-xanthene-2,7-diol,
3,4,5,6,9-pentamethyl-9H-xanthene-2,7-diol,
3,4,5,6-tetramethyl-9-ethyl-9H-xanth
Higo Mutsuko
Iyama Hironobu
Miyake Kunihito
Mulcahy Peter D.
Sumitomo Chemical Company Limited
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