IP Library Granted Patent US 9,777,086
Granted Patent B2
US 9,777,086 · App. 14/431,150 · Granted Oct 3, 2017

Polymerizable composition and method of production of resin shaped article

Inventors: Naoki Nishioka (Tokyo, JP); Nobuto Kamei (Tokyo, JP)
Assignee: RIMTEC CORPORATION
C08F132/08C08G61/08C08L65/00C09D165/00C08G2261/3324C08G2261/418C08G2261/59
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Quick Facts
Patent No.
US 9,777,086
App. No.
14/431,150
Granted
Oct 3, 2017
Kind
B2
Abstract

A polymerizable composition comprised of a mixture of a norbornene-based monomer and a metathesis polymerization catalyst which is solidified by cooling is provided. Preferably, the norbornene-based monomer has a freezing point of 20° C. or more, more preferably the metathesis polymerization catalyst is a ruthenium-carbene complex. According to the present invention, it is possible to provide a polymerizable composition which is excellent in storage stability and which enables industrial production of small resin shaped articles which are excellent in stability of quality.

Claims (22)

1. A polymerizable composition comprised of a mixture of a norbornene-based monomer and a metathesis polymerization catalyst which is solidified by cooling;

wherein the polymerizable composition is in the solid state, and

the metathesis polymerization catalyst is a compound represented by a following general formula (5) or a compound represented by a following general formula (6):

wherein, in the general formula (5), Z indicates an oxygen atom, sulfur atom, selenium atom, NR 12 PR 12 , or AsR 12 , R 12 indicates a hydrogen atom; halogen atom; or C 1 to C 20 organic group which may contain a halogen atom, oxygen atom, nitrogen atom, sulfur atom, phosphorus atom, or silicon atom,

R 1 and R 2 respectively independently indicate a hydrogen atom; halogen atom; or C 1 to C 20 organic group which may contain a halogen atom, oxygen atom, nitrogen atom, sulfur atom, phosphorus atom or silicon atom, where the organic groups which form R 1 and R 2 may be substituted, or may bond together to form a ring,

X 1 indicates an anionic ligand,

L 1 indicates a hetero atom-containing carbene compound or a neutral electron donor compound other than a hetero atom-containing carbene compound, and

R 7 and R 8 respectively independently indicate a hydrogen atom, C 1 to C 20 alkyl group, C 2 to C 20 alkenyl group, or C 6 to C 20 heteroaryl group, where the alkyl group, alkenyl group, and heteroaryl group which form R 7 and R 8 may be substituted, or may bond together to form a ring,

R 9 , R 10 , and R 11 respectively independently indicate a hydrogen atom; halogen atom; or C 1 to C 20 organic group which may contain a halogen atom, oxygen atom, nitrogen atom, sulfur atom, phosphorus atom, or silicon atom, where the organic groups which form R 9 , R 10 , and R 11 may be substituted, or may bond together to form a ring, and

R 1 , R 2 , X 1 , and L 1 may respectively bond together in any combination to form a multi-dendate chelate ligand,

wherein, in the general formula (6), m is 0 or 1,

Q is an oxygen atom, nitrogen atom, sulfur atom, methylene group, ethylene group, or carbonyl group,

is a single bond or double bond,

R 1 indicates a hydrogen atom; halogen atom; or C 1 to C 20 organic group which may contain a halogen atom, oxygen atom, nitrogen atom, sulfur atom, phosphorus atom or silicon atom, where the organic group which forms R 1 may be substituted,

X 1 and X 2 respectively independently indicate an anionic ligand,

L 1 indicates a hetero atom-containing carbene compound or a neutral electron donor compound other than a hetero atom-containing carbene compound, and

R 13 to R 21 are each a hydrogen atom; halogen atom; or C 1 to C 20 organic group which may contain a halogen atom, oxygen atom, nitrogen atom, sulfur atom, phosphorus atom, or silicon atom, where the organic groups which form R 13 to R 21 may be substituted, or may bond together to form a ring, and

R 1 , X 1 , X 2 , and L 1 may respectively bond together in any combination to form a multi-dendate chelate ligand.

2. The polymerizable composition as set forth in claim 1 wherein the norbornene-based monomer has a freezing point of 20° C. or more.

3. The polymerizable composition as set forth in claim 1 wherein a cooling temperature at the time of the solidification by cooling is made to be a temperature of 20° C. or more lower than a freezing point of the norbornene-based monomer.

4. The polymerizable composition as set forth in claim 2 wherein a cooling temperature at the time of the solidification by cooling is made to be a temperature of 20° C. or more lower than a freezing point of the norbornene-based monomer.

5. A method of production of a resin shaped article comprising a step of bulk polymerizing the polymerizable composition as set forth in claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2015
From: NISHIOKA, NAOKI; KAMEI, NOBUTO
To: RIMTEC CORPORATION
Reel/Frame 035254/0890 →
Priority Claims (1)
JP 2012-211745 · Sep 26, 2012 · national
Continuity (1)
Related Publication 20150240007A1 · Aug 27, 2015