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Catalyst for norbornene monomer polymerization and method for producing norbornene polymer

A norbornene and manufacturing method technology, applied in the field of new transition metal coordination compounds, can solve the problems of high activity and small activity reduction, low polymerization activity, unknown, etc., and achieve the effect of excellent transparency

Active Publication Date: 2015-06-10
RESONAC CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the polymerization activity is very low, and a polymer having a number average molecular weight exceeding 200,000 cannot be obtained
[0008] From the records of these prior art documents, it can be seen that in the addition homopolymerization or addition copolymerization of norbornene-based monomers having polar groups, high activity and activity of polymers with a number average molecular weight of 200,000 or more can be obtained. A small catalyst system for the reduction is unknown

Method used

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  • Catalyst for norbornene monomer polymerization and method for producing norbornene polymer
  • Catalyst for norbornene monomer polymerization and method for producing norbornene polymer
  • Catalyst for norbornene monomer polymerization and method for producing norbornene polymer

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Embodiment

[0157] Hereinafter, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not limited by these description at all.

[0158] In each embodiment and comparative example, catalytic activity is calculated by following formula:

[0159] [number 1]

[0160] Catalytic activity = (amount of polymer obtained [g]) / (moles of palladium [mmol])

[0161] The weight average molecular weight (Mw), number average molecular weight (Mn), and molecular weight distribution (Mw / Mn) of the obtained polymer were determined by gel permeation chromatography (GPC) using polystyrene as a standard substance. In addition, the composition ratio of norbornene to 5-acetoxymethyl-2-norbornene in the copolymer was determined by 1 The peak obtained by H-NMR [δ: 3.5-4.5ppm, 5-acetoxymethyl-2-norbornene (abbreviated as "ANB") "-COOCH 2 -" unit] and [δ: 0.5-3.0ppm, norbornene (abbreviated as "NB") and "CH of 5-acetoxymethyl-2-norbornene 3 CO...

Synthetic example 1

[0187] Synthesis Example 1: Synthesis of 2-Acetoxymethyl-5-Norbornene

[0188] Dicyclopentadiene (manufactured by Tokyo Chemical Industry Co., Ltd., 759.80 g, 5.747 mol), allyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd., 1457.86 g, 14.561 mol) and hydroquinone (Wako Pure Pharmaceutical Co., Ltd., 2.25 g, 0.0204 mol). After replacing the inside of the system with nitrogen, the autoclave was heated up to 190° C. while stirring at 500 rpm, and reacted for 5 hours. After the reaction, the autoclave was cooled to room temperature, the contents were transferred to a distillation apparatus, and distillation was performed under reduced pressure to obtain 1306.70 g of a colorless transparent liquid as a fraction at 0.07 kPa and 48°C.

[0189] Measure the resulting liquid 1 H-NMR confirmed the target 2-acetoxymethyl-5-norbornene. In addition, the molar ratio of the exo isomer to the endo isomer of the obtained 2-acetoxymethyl-5-norbornene was exo / endo=18 / 82.

Embodiment 1

[0190] Example 1: (π-allyl){4-(2,6-diisopropylphenylimino)-2-pentene-2-alcohol radical-κ 2 Synthesis of N, O} Palladium [Coordination Compound A-1]

[0191]

[0192] [Coordination compound A-1]

[0193] A two-necked flask equipped with a three-way valve was replaced with nitrogen, and 4-(2,6-diisopropylphenylimino)pentane-2-one (471.6mg, 1.818mmol) was added thereto, and dehydrated tetrahydrofuran ( Wako Pure Chemical Industries, Ltd., 10 ml) was dissolved. After immersing it in a dry ice-ethanol bath and cooling it to -78°C, add a 1.6mol / l hexane solution of n-butyllithium (manufactured by Wako Pure Chemical Industries, Ltd., 1.14ml, 1.82mmol) dropwise. After stirring at -78° C. for 1 hour, the temperature was gradually returned to room temperature.

[0194] A separately prepared two-necked flask equipped with a three-way valve was replaced with nitrogen, and allyl palladium chloride dimer (manufactured by Wako Pure Chemical Industries, Ltd., 329.1 mg, 0.900 mmol) was a...

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Abstract

The invention relates to a catalyst for the polymerization of norbornene monomers comprising transition metal complex (A) represented by formula (1); and a method for producing a norbornene (co)polymer, especially a norbornene copolymer containing a monomer unit represented by formulae (2) and (3), wherein a norbornen monomer is homopolyzed or copolymerized in the presence of the polymerization catalyst. Preferable examples of the transition metal complex (A) include (À-allyl){4-(2,6-diisopropylphenylimino)-2-penten-2-olato- º 2 N,O}palladium and (À-allyl){4-(1-naphthylimino)-2-penten-2-olato- º 2 N,O}palladium. In the formulae, the symbols are as defined in the description. A norbornene (co)polymer which has excellent transparency, excellent heat resistance, excellently low water absorption and excellent electrical insulation characteristics can be efficiently produced by the present invention.

Description

technical field [0001] The present invention relates to a catalyst for polymerization of a norbornene-based monomer, a method for producing a (co)polymer of a norbornene-based monomer having a polar group using the catalyst, and a novel transition compound used in the catalyst metal complexes. Background technique [0002] Conventionally, cyclic olefin-based addition polymers typified by norbornene-based polymers have been industrially used in the fields of optical films and the like as organic materials excellent in heat resistance and transparency. Various examples have been reported that such cyclic olefin-based addition polymers can be produced by polyaddition-polymerizing cyclic olefin-based monomers using catalysts containing transition metal compounds such as Ti, Zr, Cr, Co, Ni, and Pd. [0003] For example, European Patent Application Publication No. 0445755 (Patent Document 1) reports that by using a transition metal compound of Group 5-10 elements as a main cataly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F4/70C07C251/30C07F15/00C08F32/04
CPCC07C251/12C07F15/006C08F4/619C08F4/61908C08F4/7022C08F32/04C08F32/08C08F232/08C07C251/30C07F15/00C08F4/70
Inventor 藤部聪黍野信幸
Owner RESONAC CORPORATION
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