Ring-opening polymer hydrogenation products

Details Ring-opening polymer hydrogenation products Ring-opening polymer hydrogenation products

1997-03-27

1999-05-18

Zitomer, Fred

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

5253321, 525338, 526280, 5263261, C08F8/04;32/08

Patent

active

059051299

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to ring-opening polymerization polymer hydrogenation products, and more particularly, to ring-opening polymerization polymer hydrogenation products excellent in low birefringence properties and resistance to deterioration with greases and oils.


BACKGROUND ART

Hitherto, polymethyl methacrylate (PMMA) and polycarbonate (PC) have been known as optical polymer materials. However, PMMA is excellent in transparency, but has problems in heat resistance and moisture resistance. PC is superior to PMMA in heat resistance and moisture resistance, but has the problem that it is apt to have a high birefringence due to its basic structure having a benzene ring and its high melt viscosity.
Recently, ring-opening polymerization polymer hydrogenation products of norbornene monomers are used as polymer materials improved in these defects. These resins are excellent in heat resistance and moisture resistance and, furthermore, have low birefringence. However, resins of further lower birefringence are required by the further advancing technical demand.
1,4-Methano-1,4,4a,9a-tetrahydrofluorene (hereinafter referred to as "MTF") is a monomer disclosed as an example of the norbornene monomers (e.g., JP-A-3-273043, etc.). However, no examples of ring-opening polymerizing the monomer and hydrogenating the polymer are disclosed in the prior art. Therefore, no characteristics have been known on the ring-opening polymerization polymer hydrogenation products of MTF. Furthermore, hydrogenation products of ring-opening polymerization copolymers of 1,4-methano-1,4,4a,4b,5,8,8a,9a-octahydro-9H-fluorene having the similar structure to MTF (differing from MTF in that the aromatic ring structure of MTF is replaced with a cyclohexene ring structure) and 5,8-methano-3a,4a,5,8,8a,9,9a-octahydro-1H-benzoindene at a molar ratio of 4:6-6:4 are known (JP-A-3-220230). The resins have a small birefringence and have a strength and a heat resistance. However, they do not have such level of low birefringence as newly required.
Moreover, the norbornene ring-opening polymerization polymer hydrogenation products suffer from the problem that they sometimes undergo reduction in mechanical strength when greases and oils stick thereto to cause breakage.


DISCLOSURE OF INVENTION

As a result of intensive research conducted by the inventors on norbornene ring-opening polymerization polymer hydrogenation products of lower birefringence, it has been found that ring-opening polymerization polymer hydrogenation products of specific monomers have lower birefirngence and, in addition, they are excellent in resistance to deterioration with greases and oils when they have a molecular weight higher than a certain level. Thus, the present invention has been accomplished.


BEST MODE FOR CARRYING OUT THE INVENTION

Thus, the present invention provides a ring-opening polymerization polymer hydrogenation product comprising 70-100% by weight, preferably 90-100% by weight of a norbornene monomer represented by the following formula I and 0-30% by weight, preferably 0-10% by weight of other monomer copolymerizable with the said norbornene monomer, the hydrogenation rate of the double bond in the main chain being 98% or higher, the hydrogenation rate of the 6-membered ring structure being 90% or higher, the number-average molecular weight (Mn) measured by gel permeation chromatography being 12,000 or more in terms of polyisoprene: ##STR2## (wherein the 6-membered ring structure positioned lower may have a double bond).
Examples of the monomer used in the present invention are 1,4-methano-l,4,4a,4b,5,8,8a,9a-octahydro-9H-fluorene, 1,4-methano-1,4,4a,4b,5,6,7,8,8a,9a-decahydro-9H-fluorene and MTF, and preferred is MTF which is easy in preparation and purification. For example, MTF can be obtained by subjecting indene and cyclopentadiene to Diels-Alder reaction.
In the present invention, monomers which are ring-opening copolymerizable with the monomers represented by the formula I may be used in combination. These monomers include n

REFERENCES:
patent: 4166083 (1979-08-01), Ueda
patent: 5106920 (1992-04-01), Murakami
patent: 5559199 (1996-09-01), Abe

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