Yoshitomi Pharmaceutical Industries, Ltd.

Tetsuji Ike

Takeshi Inoue

Yasuhiro Hidaka

Ryoichi Kinishi

Hiroyuki Akashi

Shoichi Horie

Koreyoshi Suenobu

Yoshihiro Ozaki

Hidaka Yasuhiro

Shuichi Wakamatsu

Phosphonite and phosphonate compounds ##STR1## wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each independently a group of the formula ##STR2## wherein R is a hydrogen atom or a methyl group, p is 0 or 1, q is independently 0 or 1 with regard to each repeat unit, and m is an integer of 2 to 10, a stabilizer for organic materials comprising said compound and a stabilized organic material comprising said compound. The compound of the present invention is less volatile at high temperatures. The use of the compound of the present invention as a stabilizer for organic materials affords an extremely useful organic material which is superior in heat stability and free of degradation caused by oxidation. The compound of the present invention has excellent compatibility with the above-mentioned organic materials and hardly migrate from the organic materials. Thus, the compound of the present invention can reside in the organic material for a prolonged period of time, which in turn stabilizes the organic materials in a sustained manner.

Phosphonite or phosphonate compounds and use thereof

Tetrakis(2,4-di-tert-butyl-5-methylphenyl)-4,4'-biphenylenediphosphonite, stabilizers for organic materials, which contain said compound, and stabilized organic materials containing said compound as a stabilizer. The tetrakis(2,4-di-tert-butyl-5-methylphenyl)-4,4'-biphenylenediphosphonite has particularly superior hydrolysis resistance, and is characterized in that it has superior storage stability due to its scarce hygroscopicity. It can be purified and handled easily since it is in a powder form, and it shows less volatility at high temperatures. By using the compound of the present invention as a stabilizer for organic materials, extremely useful organic materials imparted with superior processing stability, heat resistance and resistance to oxidative degradation can be provided.

4,4'-biphenylenediphosphonite compound and use thereof

A selective process for preparing a 2,4- or 3,6-di-substituted phenol compound which comprises reacting an olefin compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, alkyl, halogen substituted alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl; with a phenol compound of the formula: ##STR2## wherein R.sup.5 is hydrogen, hydroxy, halogen, alkyl, halogen substituted-alkyl, alkoxy or --C(R.sup.6)(R.sup.7)CH(R.sup.8)(R.sup.9) (wherein R.sup.6 is hydrogen, halogen, alkyl, halogen substituted-alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.7, R.sup.8 and R.sup.9 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl), in the presence of a phosphorus compound and a carboxylic acid compound as catalysts. The methods of the present invention, which is used a phosphorus compound and a carboxylic acid compound as catalysts, are enable to make the separation procedures easy, make the reaction process and time short, not to produce any colored resultant product, and reduce that cost in manufacturing procedures.

Selective process for preparting 2,4- or 3,6-di-substituted phenol

Stabilized antifouling paint composition

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Fukuoka, Japan

Tetsuji Ike