Linear triene compound and copolymer

Details Linear triene compound and copolymer Linear triene compound and copolymer

1999-05-26

2001-10-16

Lipman, Bernard (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C336S174000

Reexamination Certificate

active

06303727

ABSTRACT:

FIELD OF THE TECHNIQUE
The present invention relates to a novel and useful linear triene compound and to a process for producing the same.
The present invention also relates to a novel an d useful ethylene/&agr;-olefin/triene copolymer, to a composition containing such copolymer and to a formed article made of such composition.
BACKGROUND OF THE INVENTION
In general, hydrocarbo n compounds having in the molecule two or more carbon-carbon double bonds are called polyenes, a variety of which have been known, including, for example, 1,3-butadiene, 1,3-pentadiene, 1,4-hexadiene, ethylidene-2-norbornene (ENB), dicyclopentadiene and so on. By co-polymerizing such a diene with an &agr;-olefin, such as ethylene, propylene or so on, an unsaturated copolymer having unsaturation bonds permitting vulcanization can be obtained. Due to its superior properties, such as weatharability, heat resistance and ozone-proof stability, such ethylenically unsaturated copolymer finds a wide variety of applications for, for example, automobile parts, industrial rubber products, electric insulator, articles for constructional and architectural uses and rubber products, such as rubber-lined cloth etc., and also for a material for polymer blends with, such as for example, polypropylene, polystyrene and others. Among these ethylene/&agr;-olefin/diene copolymers, ethylene/propylene/5-ethylidene-2-norbornene copolymer exhibits, in particular, higher vulcanization velocity as compared with other ethylenically unsaturated copolymers and, hence, has especially widely been brought into practical uses.
Even this ethylene/propylene/5-ethylidene-2-norbornene copolymer, however, does exhibit inferior vulcanization velocity as compared with those commonly used diene-rubbers, such as natural rubber, styrene/butadiene rubber, isoprene rubber, butadiene rubber and nitrile rubber, and is inferior in the ability for co-vulcanizing with diene-rubbers.
Conventional ethylene/&agr;-olefin/diene copolymers exhibit lower vulcanization velocity and, thus, are difficult to achieve an efficient productivity in producing vulcanized rubber products when reducing the vulcanization time or lowering the vulcanization temperature for the purpose of attaining a reduced energy consumption.
Therefore, it should be of great value in the industry, when such a polyene compound would be realized, that can afford to obtain, by co-polymerizing with an &agr;-olefin, such as ethylene, an ethylenically unsaturated copolymer capable of being vulcanized at a high velocity and at the same time superior in the weatherability, heat resistance and fastness to ozone.
On the other hand, it has widely been recognized that, as a general property, a vulcanizable polymer exhibiting higher vulcanization velocity tends to have inferior scorch stability. This is believed due to that a polymer exhibiting higher vulcanization velocity may cause cross linking more easily during process steps other than the vulcanization, such as the compounded rubber storage step and rubber processing step before the vulcanization, as compared with polymers exhibiting lower vulcanization velocity, resulting in, thus, a premature vulcanization. Thus, a prompt vulcanizability is a reverse feature to the scorch stability, so that a polymer exhibiting both these properties may difficultly be obtainable. Thus, when it is attemped to increase the iodine value by increasing the proportion of ENB in the production of an ethylene/propylene/ENB copolymer, the vulcanization velocity may be increased, with a sacrifice in the scorch stability, resulting in a decrease in the workability on processing the rubber blend. Namely, troubles in the practical operation due to elevation in the rate of viscosity increase may apt to occur, by, for example, decrease in the extrusion output, increase in the motor load, stuffing of the cylinder or the die and so on. On the contrary, when a decrease in the iodine value is attempted, a decrease in the productivity of the vulcanized rubber due to retarded vulcanization may not be evaded, though an improvement in the scorch stability for the copolymer as a whole and, thus, in the workability thereof may be recognizable.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a novel and useful linear triene compound capable of forming an ethylenically unsaturated copolymer which can be vulcanized at high velocity and which is superior in the scorch stability together with superiorities in weatherability, heat resistance and fastness to ozone.
Another object of the present invention is to provide a process for producing such a compound as above in an efficient manner.
A further object of the present invention is to provide a novel and useful &agr;-olefin/triene copolymer exhibiting high vulcanization velocity and superior scorch stability.
A still furter object of the present invention is to provide a composition containg such copolymer.
A still further object of the present invention is to provide a formed article made of such composition.
The linear triene compound according to the present invention is represented by the following formula (1),
in which R
1
, R
2
, R
3
, R
4
, R
5
and R
6
stand each, independently of each other, for hydrogen atom or an alkyl having 1-3 carbon atoms, R
7
represents an alkyl having 1-3 carbon atoms and n is an integer of 0-5, with the proviso that each of R
4
s or of R 5s may be identical with or different from each other, respectively, when n is 2 or greater.
The process for producing the linear triene compound according to the present invention represented by the formula (1) comprises
reacting a triene compound having a conjugated diene structure represented by the following formula (3),
in which R
1
, R
2
, R
3
, R
4
, R
5
and R
6
stand each, independently of each other, for hydrogen atom or an alkyl having 1-3 carbon atoms, R
7
represents an alkyl having 1-3 carbon atoms and n is an integer of 0-5, with the proviso that each of R
4
s or of R
5
s may be identical with or different from each other, respectively, when n is 2 or greater, with ethylene.
The first copolymer {&agr;-olefin/triene random copolymer (I-1)} according to the present invention comprises
a structural unit (U
A
) derived from an &agr;-olefin (A) having 2-20 carbon atoms and
a structural unit (U
B−1
) derived from a linear triene compound (B-1) represented by the above formula (1), wherein the proportion of the structural unit (U
B−1
) in the total of the structural unit (U
A
) plus the structural unit (U
B−1
) is in the range of 0.1-30 mole % and
the intrinsic viscosity [&eegr;] determined in decalin at 135° C. is in the range of 0.1-10 dl/g.
The first composition according to the present invention (composition containing the &agr;-olefin/triene random copolymer) comprises the &agr;-olefin/triene random copolymer (I-1) as above, a vulcanizing agent (II) and/or a filler (III).
DETAILED DESCRIPTION OF THE INVENTION
The form ed article according to the present invention comprises an extrusion-molded article, injection-molded article or transfer-molded article or a foamed product made of the above first composition.
<<The Linear Triene Compound>>
Concrete examples of the alkyl groups having 1-3 carbon atoms denoted by R
1
to R
6
and R
7
in the above formula (1) include methyl, ethyl, n-propyl and isopropyl. The numeral n stands for an integer of 0 to 5, preferably 1 to 4.
For the linear triene compound represented by the formula (1) according to the present invention {referred to hereinafter as the linear triene compound (B-1)}, a compound in which n equals 1 and both the groups R
4
and R
5
stand for hydrogen atom is preferred, wherein a particular preference is given to a compound in which both R
4
and R
5
are hydrogen atom and R
6
and R
7
denote each, independently of each other, methyl or ethyl. When such a linear triene compound (B-1) is used as a comonomer for copolymerizing with an &agr;-olefin, in particular for synthesizing the second or the third copolymer as des

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