Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1990-06-29
1992-09-08
Kight, III, John
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
528126, 528128, 528219, 528220, C08G 802, C08G 1400
Patent
active
051459388
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel poly(arylene ketones) and to a process for preparing such polymers.
Poly(arylene ether ketones), in particular all para-linked poly(arylene ether ketones), possess many desirable properties, for example, high temperature stability, mechanical strength, and resistance towards common solvents. The preparation of poly(arylene ether ketones) by two different approaches has been described in the literature. The first approach is an electrophilic synthesis in which an aryl ketone linkage is formed. The second is a nucleophilic synthesis in which an aryl ether linkage is formed. The electrophilic synthesis is preferred for preparing the novel poly(arylene ether ketones) of this invention, and the following remarks may aid understanding of the description of the novel polymers.
In such an electrophilic synthesis, the polymerization step involves the formation of an aryl ketone group from a carboxylic acid halide, acid, or other acid derivative group (hereinafter all referred to as acid derivatives) and an aromatic compound containing an aromatic carbon bearing an activated hydrogen atom, i.e., a hydrogen atom displaceable under the electrophilic reaction conditions. The monomer system employed in the polymerisation can be, for example, (a) a single aromatic compound containing both the acid derivative group and an activated hydrogen atom on an aromatic carbon for example, p-phenoxybenzoyl chloride; or (b) a two-component system of a dicarboxylic acid or acid derivative and an aromatic compound containing two activated hydrogen atoms, for example, 1,4-diphenoxybenzene and terephthaloyl chloride.
Electrophilic polymerisation of this type is often referred to as Friedel-Crafts polymerisation. Typically, such polymerisations are carried out in a reaction medium comprising the reactant(s), a Lewis acid catalyst, such as anhydrous aluminum trichloride, and solvent such as methylene chloride, carbon disulfide, nitromethane, nitrobenzene, or orthodichlorobenzene. Because the carbonyl groups of the reactant(s) and products complex with aluminum trichloride and thereby deactivate it, the aluminium trichloride catalyst is generally employed in an amount greater than one equivalent for each equivalent of carbonyl groups in the reaction medium. Other inorganic halides such as ferric chloride, may be employed as the catalyst.
Such Friedel-Crafts polymerisations generally have produced an intractable reaction product difficult to remove from the reaction vessel and purify. Further, such processes have tended to produce polymer of undesirably low molecular weight and/or of poor thermal stability. The all para-linked poly(arylene ether ketones) have been particularly difficult to prepare under such Friedel-Crafts conditions. One factor that appears to contribute to the unsatisfactory results reported in the literature is that the para-linked polymers are more highly crystalline than the ortho, meta or mixed isomeric members of this polymer family and are therefore generally more insoluble in the reaction media typically used in such Friedel-Crafts reactions. This tends to result in the premature precipitation of the polymer in low molecular weight form. Another factor that may lead to these poor results is alkylation of the terminal group which prevents further growth of the polymer chain. Also, side reactions, particularly at the ortho position of activated aromatic rings can result in a polymer that is branched and/or is more likely to cross-link at elevated temperatures such as those required for melt processing the polymer. It is generally recognized that in Friedel-Crafts reactions, ortho substitution of the polymer is more likely to occur if the reaction is conducted at elevated temperatures and/or for a relatively long reaction time. U.S. Pat. No. 3,065,205 to Bonner, U.S. Pat. Nos. 3,767,620 to Angelo et al, 3,516,966 to Berr, 3,791,890 to Gander et al, 4,008,203 to Jones and U.K. Patents No. 971,227 and 1,086,021 both to Imperial Chemical Industries, Limited, disclose the preparation of pol
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Burkard Herb
Chao Yuan
Hampton-Hightower P.
Kight III John
Raychem Limited
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