Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1990-07-17
1992-03-03
Kight, III, John
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
528176, 528193, 528194, C08G 6538, C08G 6300, C08G 6302
Patent
active
050934619
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The invention concerns a process for polycondensing diphenols at least most of which comprise a central carbon atom, groups bound to this carbon atom being hampered in their free rotation, and halides, especially chlorides, of dicarboxylic acids, using the two-phase interface procedure, in fine dispersion of the aqueous phase, consisting of diphenol, alkali hydroxide to form the diphenolate in stoichiometric relation or in slight excess, further a phase transfer catalyst in a mixture of water and an organic solubilizer, with the organic phase, consisting of a solution of the acid halide in a halogenated hydrocarbon as the solvent, whereupon, on termination of the polycondensation, the polymer is dissolved in this solvent and is precipitated from it by the addition of a precipitating agent.
STATE OF THE ART
A process of the above species is known from the European patent document A1-41495 filed by applicant. According to this European A1 document, mono-valent aliphatic alcohols such as isopropanol are used in such polycondensations employing in particular 1,1-bis(4-hydroxyphenyl)-phenylethane or 9,9-bis(4-hydroxyphenyl)fluorene as diphenols. Compared to dioxane, which earlier was frequently used as a solubilizer inert relative to the acid chlorides in two-phase interface polycondensation to prepare aromatic polyesters, this isopropanol offers most of all the advantage of its essentially low toxicity. However it was found that in the manufacture of many polyesters, for instance such as are based on 9,9-bis-(4-hydroxyphenyl)fluorene and iso/tere-phthaloylchloride with use of monovalent aliphatic alcohols such as isopropanol, other conditions being the same, the molecular weights which can be achieved are lower than when dioxane is the solubilizer (see for instance Examples 4 and 5 of said European patent document A1 41496).
EXPOSITION OF THE INVENTION
Hence it is the object of the present invention to provide a polycondensation process of the initially cited kind which uses a solubilizer, for instance isopropanol, which is comparatively non-toxic and whereby higher mean molecular weights of the polyesters to be manufactured can be achieved.
This problem is solved by the process of the invention which is characterized in that at least in the largest part acetone or methylethylketone shall be used as the solubilizer for the diphenol.
Moreover acetone and methylethylketone offer the advantage that under normal conditions they are inert to the acid chlorides, this not being the case for monovalent aliphatic alcohols, as already disclosed in the European patent document A1 41496.
Such a solubilizer evinces the property of being soluble both in the aqueous and in the organic-liquid phases. The solubilizer concentration in the aqueous phase must be adequate to reliably keep the diphenolate dissolved whereas the resultant solubilizer concentration in the organic-liquid phase may not be so high that the polymer forming in it shall precipitate before the end of the polycondensation.
In an advantageous implementation of the invention, the process of the invention is characterized in that at least the largest part of the phenols used assumes the structure ##STR1## where R is a bifunctional hydrocarbon residue containing at least one aromatic or cycloaliphatic ring.
In a further advantageous implementation of the process of the invention, the diphenol used is 9,9-bis(4-hydroxyphenyl)fluorene.
In yet another advantageous implementation of the process of the invention acetone is used as the diphenol solubilizer and dichloromethane as the solvent.
In yet another advantageous implementation of the process of the invention, an organic liquid used as the diphenol solubilizer is the same liquid which is used to precipitate the polymer.
In a last, advantageous implementation of the invention, the process is characterized in that one or more liquids used in it, namely the water, the solvent, the solubilizer for the diphenol and/or precipitant for the polymer is or are recovered by rectification.
PARTICULAR
REFERENCES:
patent: 4401803 (1983-08-01), Rieder
patent: 4418122 (1983-11-01), Rieder et al.
patent: 4430493 (1984-02-01), Rieder
patent: 4446195 (1984-05-01), Rieder et al.
patent: 4786708 (1988-11-01), Serini et al.
Isonova Technische Innovationen Ges.m.b.H.
Kight III John
Mosley T.
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