Mononuclear methylol resorcinols, mono-, di-and trimethylol resorcinols, are detected in low molecular weight resorcinolformaldehyde condensates (RFR) by gel permeation chromatography (GPC).
Further, silylated derivatives of 2- and 4-methylol resorcinols, 2, 6- and 4, 6-dimethylol resorcinols and 2, 4, 6-trimethylol resorcinol in silylated RFR can be separated by the temperature programmed capillary gas chromatography (GC), respectively.
The sample RFR were prepared by reacting resorcinol and formaldehyde (37% formalin) in the molar ratios (0. 3, 0.4 and 0. 7) at various temperature (0°C, 25°C and 80°C).
Some RFR were silylated with N, O-his (trimethylsilyl) trifluoracetamide (BSTFA).
In such cases 100 mg of RFR solution were dissolved in 2 ml of dimethylformamide. After addition of 2 ml of BSTFA the mixture was allowed to react at 40°C for 1 hour.
Analytical condition of GPC are as follows : Apparatus; HLC-801 (Toyo Soda Mfg. Co., Ltd.), Column; TSK GEL, G-3000H
8, G-2000H
8, G-2000H
8, G-1000H
8, Precolumn; GH8P, Eluent; tetrahydrofuran, Flow rate; 1ml/min, detector; RI.
Analytical condition of temperature programmed capillary GC are as follows : Apparatus; GC-4CMPFE (Shimadzu Seisakusho Co., Ltd.), Column; Stainless capillary column, 0.5 mm∅×45m, Liquid phase; SE-30, Temperature programming temperature range; from 100°C to 300°C, Temperature programming rate; 8°C/min, Detector; FID.
H NMR spectra were taken of room temperature-dried RFR on a JNM-MH-100 (Japan Electron Optics Laboratory Co., Ltd.) at 100 MHz in DMSO-
d6. Infrared spectra were obtained by the KBr method.
It was found that mononuclear methylol resorcinols exist in alkali-catalyzed RFR and non-catalyzed RFR. Furthermore, they are also detected in weak acid (such as zinc acetate, acetic acid and oxalic acid) -catalyzed RFR.
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