Reaction Of Cyanuric Chloride Research Articles

Some Reactions of Cyanuric Chloride with Negatively Substituted Alcohols1

Some Reactions of Cyanuric Chloride with Negatively Substituted Alcohols¹

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Preparation of Some Water-Repellent Agents of Reactive and the Velan Types

In an attempt to prepare the improved water-repellents for cellulosic fabrics that are structually similar to reactive dyes of the Procion group, 2-hexadecyloxy-4, 6-dichloro-s-triazine and 2-octadecylamino-4, 6-dichloro-s-triazine were synthesized by the reaction of cyanuric chloride with sodium cetylate and by the reaction of 2-amino-4, 6-dichloro-s-triazine with octadecyl chloride, respectively. Both products exhibited duarable water-repellency when applied to cellulosic fabrics.On the other hand, some water-repellents of the Velan type were prepared from various hydroxy compounds bearing a hydrophobic group, such as monoglyceride, diglyceride, higher dialkylcarbinol, Guerbet's alcohol and tartarate, by treating with formaldehyde and hydrogen chloride and subsequently quaternizing with pyridine, and their water-repellencies were examined.Among the hydroxy compounds studied, the following ones gave water-repellent finishes : synthesized and commercial monostearins (1), synthesized distearin (2), dipentadecylcarbinol (3), diheptadecylcarbinol (4), 2-tetradecyloctadecanol-1 (5), a monoglyceride mixture (6) obtained by glycerolizing hydrogenated rapeseed oil, a mixture of dialkyl tartarates (7) prepared by esterifying tartaric acid with a mixture of cetyl alcohol and stearyl alcohol.Particularly the product prepared from the monoglyceride mixture 6 showed stronger water-repellency than the others, probably owing to the presence of a longer-chain hydrophobic group (C22). Apparently the forked structure of the products derived from the distearin 2, the carbinol 3 or 4, the Guerbet's alcohol 5 and the tartarate mixture 7 showed no improved water-repellent effect. There was no definite relation between the water-repellent effect of the above mentioned products and the surface tension or the penetrating power of their aqueous solution.

Reaction of Cyanuric Chloride with alcohols.II

Cyanuric chloride and methanol react at low temperature without addition of alkali such as NaHCO3 and give (4)(See part (I);similarly in the case of (1), (2).and On.The reason is that the reaction of (2) or (3) with methanol is accelerated by the acid and this is explained by comparing the reaction velocity of (1), (2), and (3) with methanol in the presence or absence of HC1.On the other hand, the alkalis used in the reaction with methanol are divided into two of the following: i) Kinds of slowing the reaction such as NaHCO3 andCaCO3 than without the addittion of alkali, and ii) kind of giving mor vigorous acceleration such as NaOH.i) acts as an acid-removing agent and prevents rapid formation of B and C (See part (I)), it is a controlling agent for proceeding of stepwise reaction of A, B and C, and it is suitable for syntheses of (2) and (3).ii) has a tendency of accelerating the reaction of alcohol and it is suitable for synthesis of (4).

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Reaction of Cyanuric Chloride with alcohols. I

As the factors influecing on the process of reaction (1) of cyanuric chloride with alcohols, the reactivities of alcohols and the effect of-OR in (2) and (3) on the reactivity of residual chlorine atom have been investigated from estimation of reaction velocity constant and evolved CO2in the presence of CaCO2The reactivities of alcohols were found to be decreased in the order of CH3OH>C2H5OH>η-C4H9OH>η-C3H7OH>iso-C3H7OH, and the deactivation effect of the substituent groups were in order of -NH2 (-NHAr)>-OR>OAr, -0C2H5>-OCH3.The reactions (1) with various alcohols have been observed at various temperatures and reaction curves were obtained.The results indicated that the reactions were proceeded stepwise.Optimum temperatures for obtaining (2) and (3) were clarified.

Reactions of Cyanuric Chloride and its Derivatives

Reactions of Cyanuric Chloride and its Derivatives

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