Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1989-08-04
1992-05-26
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560223, 560192, 560197, 568842, 526245, 385145, C07C 6962, C08F 1820
Patent
active
051165449
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a novel hexafluoroneopentyl alcohol, hexafluoroneopentyl acrylate or methacrylate obtained as its derivative, fluorine-containing polymer prepared from the derivative and the use of the polymer as an optical material.
PRIOR ART AND ITS PROBLEMS
Optical fibers are well known which comprise a transparent glass or plastics core and a cladding covering the core concentrically therewith to provide a composite fiber and having a lower refractive index than the core material, such that when light is applied at one end of the fiber, light travels through the fiber while being totally reflected in its interior.
Various polymers have been proposed for use as plastics materials for forming a cladding. Of these polymers, only a few are fully satisfactory in the properties of having a high softening temperature and a low refractive index which are required of cladding materials for optical fibers. Of the few, perfluoro-t-butyl methacrylate is disclosed in Japanese Unexamined Patent Publication No. 49-129,545 as optical materials capable of fulfilling said property requirements.
However, perfluoro-t-butyl methacrylate has the drawbacks of having a low flexibility and a poor adhesion to the core.
An object of the present invention is to provide a novel monomer compound and a starting material for the monomer compound, the monomer compound being capable of giving a polymer which is free of the foregoing drawbacks, namely fully satisfactory in the properties of having a high softening temperature and a low refractive index as required of cladding materials for optical fibers and excellent in the flexibility and good in the adhesion to the core.
MEANS FOR SOLVING THE PROBLEMS
The present inventors discovered that a polymer prepared from hexafluoroneopentyl acrylate or methacrylate which is a novel monomer compound has a specifically high glass transition temperature (hereinafter referred to as "Tg"), a low refractive index, a great flexibility and a good adhesion to the core and that the hexafluoroneopentyl acrylate or methacrylate can be easily synthesized from a novel hexafluoroneopentyl alcohol. The present invention has been accomplished based on these novel findings.
According to the present invention, there are provided a hexafluoroneopentyl alcohol represented by the formula ##STR1## and hexafluoroneopentyl acrylate or methacrylate represented by the formula ##STR2## wherein X represents hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom or methyl group.
According to the present invention, there are further provided a fluorine-containing polymer comprising a structural unit represented by the formula ##STR3## wherein X represents hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom or methyl group, and an optical material prepared from said fluorine-containing polymer.
The hexafluoroneopentyl alcohol of this invention can be prepared by the following process. First, as illustrated in the following reaction scheme, an adduct of octafluoroisobutene with methanol (a) is subjected to a reaction for removing HF, giving the olefin (b) shown below. The olefin (b) is subjected to rearrangement reaction, giving the acid fluoride (c) shown below which is then subjected to reduction. ##STR4##
The foregoing rearrangement reaction is conducted in the presence of a suitable solvent. Examples of preferred solvents are dimethylformamide, dimethylacetoamide, etc. The amount of the solvent used is 0.01 to 10 times, preferably 0.1 to 2 times, the amount of the olefin (b). A smaller amount of the solvent used reduces the rate of rearrangement reaction, whereas a larger amount thereof involves a cumbersome treatment of waste and leads to formation of reaction product in a small amount despite the large reaction scale. A preferred reaction temperature is in the range of room temperature to 100.degree. C.
The reduction from the acid fluoride (c) to the product (d) is carried out using a reducing agent in an organic solvent. Examples of usef
Inukai Hiroshi
Kitahara Takahiro
Yasuhara Takashi
Daikin Industries Ltd.
Killos Paul J.
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