Über die synthese und das redoxverhalten von molekulareinheitlichen hydrochinon‐phenol‐formaldehydkondensaten

Abstract

ZUSAMMENFASSUNG:Mit dem Ziel, Modellsubstanzen fur Redoxharze, aufgebaut aus Hydrochinon, Phenol und Formaldehyd, zu erhalten, wurden niedermolekulare molekulareinheitliche Kondensate dieser Stoffe dargestellt. Das Redoxverhalten der Verbindungen wurde durch potentiometrische Titration untersucht. Der Verlauf der Titrationskurven wurde theoretisch gedeutet. SUMMARY:Compounds of low and uniform molecular weight were prepared by condensation of hydrochinone, phenol and formaldehyde. They were used as models for redox resins. The redox properties of these compounds were investigated by potentiometric titration. The titration curves were analyzed theoretically.Die saurekatalysierte Kondensation von Hydrochinon, Phenol und Formaldehyd ergab die von uns untersuchten Polykondensations-Redoxharse, fiir die sich auf den verschiedensten Gebieten der Chemie interessante Moglichkeiten erschlossen haben l ) . Die Struktur der Harze zeigt das folgende idealisierte Formelbild ; sie enthalten Hydrochinon-und Phenol-Einheiten, die iiber Methylenbriicken verkniipft sind.

Electron‐transfer polymers (oxidation‐reduction polymers)

“…With the formal recognition of this class of chemically reactive polymers (31) there has been a revival of interest in substances derived from hydroquinone-formaldehyde condensates with or without added phenols. The most extensive and thorough work in this area has been done by Manecke and his coworkers (1,135,145,149,158,160). Others have also been active in this area (1,179,225,23 1,236).…”

“…In order to understand the behaviors of substances of this kind a number of investigators have prepared dimers, trimers, and other oligomers and have studied their properties (1,135,145,158,160). This work is reviewed in Section IIIc.…”

“…Several investigators have studied the properties of dimers, trimers, and very small polymers of the hydroquinone types with a view toward simplifying the problem of interpreting polymer behavior. This approach was taken by Lindsey and his group (1,65,119,120,124) in connection with their studies of hydroquinone-formaldehyde polymers ; by Cassidy and his colleagues (181)(182)(183)239) in studies of the behavior of poly(vinylhydroquinone), and by Manecke and colleagues (59,135,145,158,160,171) in a series of studies related to phenol-formaldehyde redox polymers.…”

Polyhydrochinonsulfone. I. Synthese einiger molekulareinheiticher Hydrochinon‐Zweikernverbindungen mit Sulfonbrücken

“…1,19 g 2.5-Dimethoxybenzolsulfochlorid (5 mMol) werden in 7 ml Aceton gelost und auf einmal zur Losung von 0,64 g Hydrochinonmonomethylather (5 mMol 2,76 C127,69 N 5,47 S 12,52 Gef. C 33,14 H 2,88 C127,50 N 5.56 S 12,65 Sulfonylid (XVIII)…”