Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2000-12-18
2002-06-11
Zitomer, Fred (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S308000, C526S309000, C526S336000, C526S339000, C526S348000
Reexamination Certificate
active
06403742
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an olefin copolymer having a functional group, a production process thereof and a rubber composition comprising the olefin copolymer having the functional group, and more particularly to an olefin copolymer having a functional group, which permits providing an elastomer excellent in adhesion to and compatibility with other materials, coating property, printability and durability, and suitable for use as a material for automotive parts, mechanical parts, electronic parts, civil engineering and construction materials, etc., a production process thereof, and a rubber composition comprising the olefin copolymer having the functional group.
2. Description of the Background Art
Olefin copolymer elastomers such as ethylene/&agr;-olefin copolymer elastomers and ethylene/&agr;-olefin
onconjugated diene copolymer elastomers have heretofore been widely used as materials for automotive parts, mechanical parts, civil engineering and construction materials, etc. because they are elastomeric materials excellent in heat resistance and weather resistance. The olefin copolymer elastomers are also widely used as modifiers for resins such as polypropylene and polyethylene.
However, such olefin copolymer elastomers involve problems that they have neither polar group nor functional group in their molecular structures, and so their adhesion to metals, and adhesion to and compatibility with other elastomers and resins than polyolefins are low, and the resulting molded or formed products are inferior in coating property and printability.
For such reasons, olefin copolymers with a functional group such as a carboxyl group or amino group introduced by using a cycloolefin having such a functional group as a monomer component have been proposed (see Japanese Patent Publication No. 43275/1974, Japanese Patent Application Laid-Open Nos. 259012/1989 and 54009/1989, Japanese Patent Application Laid-Open No. 503963/1992 (through PCT route), etc.).
However, such olefin copolymers with the functional group introduced thereinto have the following problems.
Namely, an active tertiary hydrogen atom (hydrogen atom bonded to a tertiary carbon atom) produced by substitution of a hydrogen atom with the functional group is present in a structural unit derived from the cycloolefin having the functional group, in other words, the tertiary hydrogen atom is bonded to a carbon atom to which the functional group has been bonded. When such a tertiary hydrogen atom is present in the copolymer, the tertiary hydrogen atom tends to separate from the carbon atom to produce a radical. Therefore, such a copolymer is apt to cause scission of a molecular chain, deterioration by oxidation and deterioration by the separation of a substituent group containing the functional group due to the formation of the radical. Accordingly, it is difficult to provide an elastomer excellent in durability by the olefin copolymer in which the functional group has been introduced.
In addition, a cycloolefin having, for example, a carboxyl group as a functional group gives off a strong odor. When such a cycloolefin is used as a monomer, the resulting copolymer also gives off a strong odor because the cycloolefin unavoidably remains in the copolymer. Therefore, such a copolymer involves an environmental or sanitary problem.
SUMMARY OF THE INVENTION
The present invention has been made on the basis of the foregoing circumstances, and it is the first object of the present invention to provide an olefin copolymer having a functional group, which permits providing an elastomer which is high in adhesion to and compatibility with other materials, coating property and printability and excellent in durability, and gives off no or little odor.
The second object of the present invention is to provide a process capable of exactly producing an olefin copolymer having a functional group, which permits providing an elastomer which is high in adhesion to and compatibility with other materials, coating property and printability and excellent in durability, and gives off no or little odor.
The third object of the present invention is to provide a rubber composition, which permits providing an elastomer which is high in adhesion to and compatibility with other materials, coating property and printability and excellent in durability, mechanical properties and abrasion resistance, and gives off no or little odor.
According to the present invention, there is thus provided an olefin copolymer having a functional group, which comprises:
a structural unit (a) derived from ethylene,
a structural unit (b) derived from an &agr;-olefin having 3 to 12 carbon atoms, and
a structural unit (c) represented by the following general formula (1),
and has an intrinsic viscosity [&eegr;] of 0.1 to 10 dl/g as measured in decalin at 135° C.;
wherein X
1
and X
2
mean, independently of each other, a hydrogen atom, a hydrocarbon group or the following specific functional group, at least one of X
1
and X
2
is the specific functional group, R
1
and R
2
denote, independently of each other, a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, one of R
1
and R
2
, which is bonded to a carbon atom to which the specific functional group is bonded, is the hydrocarbon group having 1 to 10 carbon atoms, and n stands for an integer of 0 to 2;
Specific Functional Group
a functional group selected from the group consisting of a hydroxyl group, a hydrocarbon group to which a hydroxyl group is bonded, a carboxyl group, a hydrocarbon group to which a carboxyl group is bonded, a primary or secondary amino group, a hydrocarbon group to which a primary or secondary amino group is bonded, a quaternary ammonium salt of a primary or secondary amino group and a hydrocarbon group to which a primary or secondary amino group is bonded, an amide group having at least one active hydrogen atom bonded to a nitrogen atom, a hydrocarbon group to which such a amide group is bonded, and an imide group composed of X
1
and X
2
and represented by —CO—NH—CO—.
According to the present invention, there is also provided an olefin copolymer having a functional group, which comprises:
a structural unit (a) derived from ethylene,
a structural unit (b) derived from an &agr;-olefin having 3 to 12 carbon atoms,
a structural unit (c) represented by the above-described general formula (1), and
a structural unit (d) derived from a nonconjugated diene,
and has an intrinsic viscosity [&eegr;] of 0.1 to 10 dl/g as measured in decalin at 135° C.
In the olefin copolymers having the functional group according to the present invention, it may be preferable that proportion of the structural unit (a) derived from ethylene be 5 to 90 mol %, the structural unit (b) derived from the &agr;-olefin having 3 to 12 carbon atoms be 5 to 60 mol %, the structural unit (c) represented by the general formula (1) be 0.01 to 30 mol %, and the structural unit (d) derived from a nonconjugated diene be 0 to 12 mol %.
In the olefin copolymers having the functional group according to the present invention, the structural unit (c) represented by the general formula (1) may preferably be such that only one of X
1
and X
2
in the general formula (1) is the specific functional group, and R
1
or R
2
, which is bonded to the carbon atom to which the specific functional group is bonded, is a hydrocarbon group having 1 or 2 carbon atoms, and particularly that the other of X
1
and X
2
is a hydrogen atom, and R
1
or R
2
, which is bonded to the carbon atom to which the hydrogen atom is bonded, is a hydrogen atom.
In the olefin copolymers having the functional group according to the present invention, the glass transition temperature may preferably be −90 to 50° C., more preferably −70 to 10° C.
According to the present invention, there is further provided a process for producing an olefin copolymer having a functional group, which comprises the steps of:
reacting a functional group-containing cycloolefin represented by the following gener
Maruyama Youichirou
Oshima Noboru
Sawada Katsutoshi
Tsuji Syouei
JSR Corporation
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Zitomer Fred
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