Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2002-03-19
2003-12-30
Davis, Brian (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S083000
Reexamination Certificate
active
06670497
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an electron donor of an olefin polymerization catalyst, a novel phthalic acid diester derivative used as a plasticizer for resins such as vinyl chloride, a component for intermediates for the preparation of various compounds, and an electron donor used in the olefin polymerization catalyst containing the phthalic acid diester derivative.
BACKGROUND ART
Conventionally, phthalic acid diesters have been used as a common plasticizer for vinyl chloride. Diethyl phthalate, dibutyl phthalate, and di-iso-octyl phthalate are typical phthalic acid diesters. In the technology for polymerizing olefins, typically propylene, in the presence of a solid catalyst comprising magnesium and titanium as major components, an electron donor (an internal electron donor) is added to the solid catalyst to improve the stereoregularity of the formed polymer and the polymerization activity. A number of reports have proposed the use of specific phthalic acid esters as such an electron donor.
As a prior art using a phthalic acid diester as one of the components of the olefin polymerization catalyst, Japanese Unexamined Patent Publication No. (hereinafter referred to as JP-A) 63310/1982 and JP-A No. 63311/1982, for example, disclose a method of polymerizing olefins having three or more carbon atoms using a combined catalyst comprising a solid catalyst component containing a magnesium compound, titanium compound, and an electron donor such as a diester compound, e.g., phthalic acid ester, an organoaluminum compound, and an organosilicon compound having a Si—O—C linkage. JP-A 6006/1989 discloses a solid catalyst component for olefin polymerization containing an alkoxymagnesium, titanium tetrachloride, and dibutyl phthalate. The solid catalyst component was proven to be successful to some extent in producing a stereoregular propylene polymer at a high yield.
The polymers produced using these catalysts are used in a variety of applications including formed products such as parts of vehicles and household electric appliances, containers, and films. These products are manufactured by melting polymer powders produced by the polymerization and by forming the melted polymer using any one of various molds. In manufacturing formed products, particularly large products, by injection molding, melted polymers are sometimes required to have high fluidity (melt flow rate). Accordingly, a number of studies have been undertaken to increase the melt flow rate of polymers.
The melt flow rate greatly depends on the molecular weight of the polymers. In the polymer industry, hydrogen is generally used as a molecular weight regulator for polymers in the polymerization of olefins. In this instance, a large quantity of hydrogen is usually added to produce low molecular weight polymers which are the polymers having a high melt flow rate. However, the quantity of hydrogen which can be added is limited because of the pressure resistance of the reactor from the viewpoint of safety. In order to add a larger amount of hydrogen, the partial pressure of monomers to be polymerized has to be decreased. The decrease in the partial pressure, however, is accompanied by a decrease in the productivity. Additionally, use of a large amount of hydrogen may bring about a problem of cost. Development of a catalyst capable of producing polymers with a high melt flow rate by using a smaller amount of hydrogen, in other words, a catalyst which has a high activity to hydrogen or high response to hydrogen and which produces a highly stereoregular polymer at a high yield has therefore been desired. In the above-mentioned prior art, however, it is not sufficient to solve such a problem.
Accordingly, an object of the present invention is to provide a novel phthalic acid diester derivative useful as one of the components for an olefin polymerization catalyst, particularly a catalyst for the polymerization of propylene or ethylene, having a high response to hydrogen, which can produce polymers having high stereoregularity in an extremely high activity and high yield, and an electron donor used as an olefin polymerization catalyst containing the phthalic acid diester derivative as an effective component.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive studies to solve the problems in conventional technologies relating to the catalysts for the polymerization of olefins. As a result, the present inventors have discovered a novel phthalic acid diester derivative which is extremely effective as an electron donor used as one of the components of such a catalyst. Confirmation of such an effect has led to the completion of the present invention.
Specifically, the above object is achieved in the present invention by a phthalic acid diester derivative of the following formula (1),
wherein R
1
is an alkyl group having 1 to 8 carbon atoms or a halogen atom; R
2
and R
3
may be either identical or different, representing an alkyl group having 1 to 12 carbon atoms; and n, which indicates the number of R
1
, is 1 or 2, provided that when n is 2, the two R
1
groups may be either identical or different.
The above object is further achieved in the present invention by an electron donor used in a catalyst for the polymerization of olefins comprising a phthalic acid diester derivative of the above formula (1) as an effective component.
BEST MODE FOR CARRYING OUT THE INVENTION
In the phthalic acid diester derivative of the present invention, given as examples of the alkyl group having 1 to 8 carbon atoms represented by R
1
of the formula (1) are a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a t-butyl group, a n-pentyl group, an iso-pentyl group, a neopentyl group, a n-hexyl group, an iso-hexyl group, a 2,2-dimethylbutyl group, a 2,2-dimethyl pentyl group, a iso-octyl group, and a 2,2-dimethylhexyl group. As halogen atoms represented by R
1
, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom can be given. Of these groups represented by R
1
, preferable groups are a methyl group, an ethyl group, a t-butyl group, a chlorine atom, a fluorine atom, and a bromine atom, with the methyl group, t-butyl group, chlorine atom, fluorine atom, and bromine atom being particularly preferable.
The groups represented by R
2
or R
3
include a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a t-butyl group, a n-pentyl group, an iso-pentyl group, a neopentyl group, a n-hexyl group, an iso-hexyl group, a 2,2-dimethylbutyl group, a 2,2-dimethyl pentyl group, an iso-octyl group, a 2,2-dimethylhexyl group, a n-nonyl group, an iso-nonyl group, a n-decyl group, an iso-decyl group, and a n-dodecyl group. Of these, an ethyl group, a n-butyl group, an iso-butyl group, a t-butyl group, a neopentyl group, an iso-hexyl group, and an iso-octyl group are preferable, with an ethyl group, a n-butyl group, a neopentyl group, and an iso-hexyl group being particularly preferable.
The symbol n, which indicates the number of R
1
, is 1 or 2, provided that when n is 2, the two R
1
groups may be either identical or different. When n=1, the substituent R
1
replaces the hydrogen atom at the 3, 4, or 5 position of the phthalic acid diester derivative, and when n=2, R
1
replaces the hydrogen atoms at the 4 and 5 positions.
Preferable phthalic acid diester derivatives are compounds having the structure of the formula (1), wherein n=1 or 2, R
1
is an alkyl group with 1 to 5 carbon atoms or a halogen atom, and R
2
and R
3
are alkyl groups with 4 to 8 carbon atoms including a tertiary carbon atom.
Specific examples of the compounds of the above formula (1), wherein n=1 or 2, R
1
is an alkyl group with 1 to 5 carbon atoms or a halogen atom, and R
2
and R
3
are alkyl groups with 4 to 8 carbon atoms including a tertiary carbon atom, include dineopentyl 3-methylphthalate, dineopentyl 4-methylphthalate, dineopentyl 3-ethylphthalate, dineopentyl 4-ethylphthalate, t-butylneopentyl
Hosaka Motoki
Nishiyama Isa
Ogawa Hayashi
Sato Maki
Suzuki Yukihiro
Davis Brian
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Toho Titanium Co., Ltd.
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