Synthesis and application of new raw materials of resins for paint industry. II.

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  • 新規な塗料用樹脂原料の合成と応用 (第2報)
  • 新規な塗料用樹脂原料の合成と応用-2-長鎖α-オレフィンより誘導されるグリコール
  • シンキ ナ トリョウヨウ ジュシ ゲンリョウ ノ ゴウセイ ト オウヨウ 2 チョウサ アルファ-オレフィン ヨリ ユウドウ サレル グリコール
  • 長鎖α-オレフィンより誘導されるグリコール
  • Glycols derived from long chain α-olefins

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Abstract

The long chain 1, 2-glycols were prepared by the reaction of either performic or peracetic acid with various α-olefins covering C6-7, C7-9, C9-11, C11-15 and C15-20. The best yield was obtained by the reaction of C6-7 olefin with peracetic acid and this was 80%. The compatibility of olefins to the reaction system affected greatly upon the yield of 1,2-glycols, which tended to fall down according to increase of the carbon numbers.<BR>The alkyd resins for coating were synthesized from 1,2-glycols thus prepared and dibasic acids.<BR>The baking type enamels were prepared by blending these alkyd resins with the butylated melamine-formaldehyde resin and the film properties were evaluated after baking them at 120°C for 30min. Excellent films were obtained from 1,2-glycol alkyds. Among them, the alkyd resin from C6-7 glycol showed excellent hardness, adhesiveness and water resistance in comparison with the usual coconut oil modified alkyd resin. This was also superior in water resistance than the branched fatty acid modified alkyd resin which is said as generally good in the water resistance.<BR>From these facts, it is considered that such a water resistance of 1,2-glycol alkyd resin depends upon decrease of the ester bond concentration in the alkyd resin. Therefore, three model compounds of alkyd resin were prepared in order to compare their hydrolyzability. The hydrolysis were carried at 70°C in ethanol by using quadruple mols of tetramethylammonium hydroxide to the ester. The rate of reaction was determined by titration of alkali consumption periodically.<BR>The apparent second-order rate constants of hydrolysis of the model compouds corresponding to the long chain 1,2-glycol, to the coconut oil and to the branched fatty acid modified alkyds were 3.9, 3.7 and 3.5 10-41l/mol. sec., respectively. The hydrolysis of the model compound of the coconut oil modified type was about twice as fast as the others.<BR>From these results, the authors are considering that the difference in the water resistance between the film from 1,2-glycol alkyd and the branched fatty acid type is affected by the cured state of film, or the difference of crosslinking at 120°C, because the rate of hydrolysis of 1,2-glycol alkyd model in solution is nearly equal to that of the branched fatty acid type.

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