Novel organometallic compound having high metathesis activity and method for preparation thereof, metathesis reaction catalyst

An organometallic and metathesis polymerization technology, applied in the direction of ruthenium organic compounds, osmium organic compounds, platinum group organic compounds, etc., can solve the problems of catalyst dispersion affecting reaction rate, uneven polymer physical properties, and product safety problems

Inactive Publication Date: 2003-10-15
SEKISUI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this catalyst, metal alkyls, etc., are not activated in the system, but show activity as a single complex, so if the catalyst is added to a metathesis reactive monomer, the reaction starts immediately, and there is a gap in the catalyst. Issues affecting reaction rate control such as dispersion
This sometimes becomes a fatal problem when polymerizing cross-linking monomers such as dicyclopentadiene. For example, there are great restrictions on the process, and there are problems such as uneven physical properties of the obtained polymer.
In this regard, it is generally known to add triphenylphosphine to the system to delay polymerization, but at this time, since impurities such as phosphorus are mixed in the system, there is a problem with the safety of the product.

Method used

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  • Novel organometallic compound having high metathesis activity and method for preparation thereof, metathesis reaction catalyst
  • Novel organometallic compound having high metathesis activity and method for preparation thereof, metathesis reaction catalyst
  • Novel organometallic compound having high metathesis activity and method for preparation thereof, metathesis reaction catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～15

[0085] In Examples 1 to 15, organometallic compounds having structures represented by formulas (3) to (17) described later were synthesized according to any of the methods described in the above reaction formula (B) or (C). Table 1 shows the structural formulas of the organometallic compounds obtained in each example and the types of metal elements, ligands, substituents, etc. in the above-mentioned general formula (2).

[0086] In addition, in Example 1, as described in the following (A) to (B), the organometallic compound of formula (3) was synthesized according to the two methods of (B) and (C) above, but any method Both yield the same organometallic compound.

[0087] In addition, in Examples 2 to 13 and Example 15, except for changing the starting materials, the same steps as in Example 1 were used to experiment with any method of (B) or (C) to obtain each desired organometallic compound. In addition, in the method of (c), it has the disadvantage of being difficult to i...

Embodiment 16

[0116] In this example, an organometallic compound having a structure represented by the following formula (19) was synthesized according to the method described in the above-mentioned reaction formula (A).

[0117] 0.006 mol of RuCl 2 (PPh 3 ) 3 and 0.006 mol of trimethylsilyl diazomethane in 20 ml of dichloromethane, reacted at -78°C for 5 minutes. Next, the reaction solution was raised to room temperature, and 0.0132 mol of tricyclohexylphosphine was added to react for 30 minutes. After the reaction was completed, the solvent was removed under reduced pressure, and the complex was isolated by recrystallization in a dichloromethane / methanol system (yield 75%). As a result of analysis, it was judged to have the structure of formula (19) described later.

[0118] 1H-NMR (CDCl 3 )δ=0.20(s, 9H, -SiMe 3 ), 1.18, 1.49~1.72, 2.64 (multiple peaks, 66H, PCy 3 ), 19.8 (s, Ru=CH, 1H, Ph): 31P{1H} NMR (CDCl 3 )δ=19.60(s). Elemental analysis: C40H76Cl2P2SiRu: calculated value C...

Embodiment 17～19

[0122] In Examples 17 to 19, polymers obtained by performing metathesis polymerization of DCPD using the organometallic compound of the present invention were evaluated as follows.

[0123] Weigh 0.1m mol (DCPD1 / 10000 mol) of the organometallic compound of the present invention represented by the above formulas (3), (4), and (13), dissolve it in 0.5g of toluene, and add it to 132g of DCPD , set a 4mm-thick spacer to flow into the liquid, keep it at 80°C for 1 hour, then leave it at 120°C for 1 hour to obtain a polymer, and prepare a sample for physical property evaluation. The temperature of the tan δ peak of the obtained sample was measured by the dynamic viscoelasticity measurement method (measurement by the tensile method (n=1) of the viscoelastic spectrum data according to JIS K7198), and this was made into the glass transition temperature of the resin.

[0124] Next, a 0.5-g test piece was taken out from the obtained polymer, weighed in a 10-ml graduated flask, and toluen...

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Abstract

An organometallic compound represented by the general formula (1) or (2); a method for preparing the organometallic compound; a metathesis reaction catalyst comprising the organometallic compound; a method of polymerization using the metathesis reaction catalyst; and a polymer produced by the method of polymerization.

Description

technical field [0001] The present invention relates to a new organometallic compound with high metathesis activity and its production method, a metathesis reaction catalyst containing it, a polymerization method using the catalyst, and a polymer obtained by the polymerization method. Novel organometallic compound excellent in stability and metathesis reactivity and excellent in reaction controllability, method for producing same, metathesis reaction catalyst containing the novel organometallic compound, polymerization method using the catalyst, and polymerization method using the same obtained polymer. technical background [0002] The metathesis reaction is used in the synthesis of various monomers such as pharmaceuticals, and the norbornene-based monomer mainly composed of dicyclopentadiene (hereinafter referred to as DCPD) which is a representative monomer that can be used in metathesis polymerization The reaction injection molding (hereinafter referred to as RIM) metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00C07F15/00C08G61/08
CPCC07F15/0046C08G61/08C07F15/002C07F19/00
Inventor 森田健晴平池宏至后藤信弘中谷政史小泽文幸片山博之
Owner SEKISUI CHEM CO LTD
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