Nitto Denko Co. Ltd.

Nitto-denko Corporation

Nitto Electric Industrial Co., Ltd.

Fuji Yakuhin Kogyo Kabushiki Kaisha

Tetsuo Omata

Shuji Senda

Yutaka Nakazono

Eiichiro Fukusaki

Makoto Kojima

Masayuki Satake

Kenji Mori

Susumu Satoh

Takeshi Sugai

Yasuo Ninomiya

Tadashi Takeuchi

Ken Hibino

Katsuhide Kojima

Miklos Toth

Masakazu Aburatani

Kaichi Tanida

Eiichiro Fukuzaki

Yoko Tsuda

Tamaki Tanaka

Chikara Kajimoto

Eriko Kumagai

Hiromichi Ota

Hiroshi Takahama

Yasuyuki Kimura

Hans-Rudolf Buser

Hiroyuki Yuasa

Heinrich Arn

Minako Hada

Polyelectrolyte comprising a (METH) acrylic polymer and an ionic salt

A process for preparing the sex pheromone of Lymantria dispar L. effectively which comprises the steps of reacting 1-bromodecane and propargyl alcohol tetrahydropyranylether in the presence of sodium hydroxide to give 1-tetrahydropyranyloxy-2-tridecyne, treating the tetrahydropyranyloxy-2-tridecyne with p-toluenesulfonic acid to give 2-tridecyn-1-ol, catalystic-hydrogenating the 2-tridecyn-1-ol in the presence of Lindlar catalyst to give (Z)-2-tridecen-1-ol, oxidizing the (Z)-2-tridecen-1-ol with peroxide to give (.+-.)-cis-2,3-epoxy-1-tridecanol, reacting the (.+-.)-cis-2,3-epoxy-1-tridecanol with acid anhydride in the presence of hydrolase in an organic solvent for a stereoselective acylation and recovering unreacted optically active (2R, 3S)-cis-2,3-epoxy-1-tridecanol after the acylation, reacting the optically active (2R, 3S)-cis-2,3-epoxy-1-tridecanol with toluenesulfonylchloride to give (2R, 3S)-cis-1-p-toluenesulfoxy-2,3-epoxytridecane, and reacting the (2R, 3S)-cis-1-p-toluenesulfoxy-2,3-epoxytridecane with di(4-methylpentyl) lithium copper reagent to yield (7R, 8S)-cis-2-methyl-7,8-epoxyoctadecane which is the sex pheromone of Lymantria dispar L.

Process for preparing the sex pheromone of Lymantria dispar L

A pressure-sensitive adhesive composition showing the adhesive force and the cohesive force with a good stability is disclosed. The composition comprises a copolymer of a (meth)acrylic acid alkyl ester (a) having an alkyl group having from 2 to 14 carbon atoms and a (meth)acrylic acid alkyl ester (b) having a carboxyl group or a hydroxyl group at the terminal end and having an alkyl group having from 3 to 14 total carbon atoms as the ester side chain. In particular, when the carbon atom number of the alkyl group of the monomer (b) is less by one than or not less than the same number as the carbon atom number of the alkyl group of the monomer (a), the effect of the functional group can be most effectively exhibited. A pressure-sensitive adhesive tape or sheet is also disclosed, comprising a support having formed at least one surface thereof the pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition.

Pressure-sensitive adhesive composition and pressure-sensitive adhesive

A synthesis method of physiologically active .delta.-lactone, which comprises addition-reacting diethyl methylmalonate and methacrolein in the presence of a base.

Synthesis method of physiologically active delta-lactone

This invention relates to a novel ester which presents as (CF 1) and a method for the production of the same as well as a process for hydrolysis and a method for the determination of an optical purity using this ester, and the object thereof is to provide an intermediate for the synthesis or various natural products, which has high stability, and the optical purity of which can readily be determined, according to the esterification of 1-oxo-5-hydroxymethyl-2-cyclohexene which is unstable to acids and alkalis. ##STR1##

Ester and method for production thereof as well as hydrolysis process

This invention relates to methods for producing optically active hydroxyesters and also to methods for producing and purifying optically active five-membered ring lactones. More specifically, the invention provides methods for efficiently, safely, and selectively producing and purifying optically active (R)-hydroxyester (shown by formula 1) and optically active (S)-hydroxyester (shown by formula 2) in high state of purity at ordinary temperature. The invention also relates to application of the interconvertible optically active (R)-five-membered ring lacton (shown by formula 5). They are intermediates for synthesizing various medicines, agricultural chemicals, and biologically active substances, however especially useful for synthesizing pheromone of a noxious insect, Popillia japonica Newman. ##STR1## (Here, R.sub.1 denotes --C.tbd.C--R.sub.3 or --C.dbd.C--R.sub.3 ; R.sub.2 and R.sub.3 denote straight chain or branched alkyl groups containing 1 to 10 carbon atoms; R.sub.4 denotes alkyl groups, aralkyl groups, or haloalkyl groups containing 1 to 12 carbon atoms and the end group of R.sub.4 may be carboxyl groups; * denotes asymmetricrbon atoms.)

Method of producing optically active hydroxyesters

This invention relates to the methods of preparing optically active epoxy alcohol which is caracterized by the steps of adding carboxylic anhydride to racemic epoxy alcohol (formula 1) in the presence of a hydrolase in an organic solvent, esterifying (-)-form of the epoxy alcohol preferentially to be epoxy ester (formula 2), separating optically active epoxy ester (formula 2) from optically active epoxy alcohol (formula 3) to yield optically active epoxy alcohol (formula 4), so that epoxy alcohol (formula 1) in high purity can be obtained easily and safely at ordinary temperature. ##STR1##

Methods of preparing optically active epoxy alcohol

The present invention provides mainly (3Z,6Z)-cis-9,10-epoxy-1,3,6-heneicosatriene (formula 1) and (3Z, 6Z)-cis-9,10-epoxy-1,3,6-elcosatriene (formula 2) which are Hyphantria cunea sex pheromones. The invention provides attractant components having high attraction effect for Hyphantria cunea, that is, Hyphantria cumea sex pheromones having high attraction activity and the intermediates which can selectively synthesize such pheromones with great ease. Furthermore, the invention provides attractant compositions with high attraction effect for Hyphantria cunea including such above noted pheromones. Consequently, this invention is completed. ##STR1##

Hyphantria cunea sex pheromones and attractant compositions including

A medical composition for external use comprising a proline ester represented by formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are as defined in the specification, or a prolinol ester represented by formula (II): ##STR2## wherein R.sub.3 and R.sub.4 are as defined in the specification. The composition enhances percutaneous penetration absorption of an active ingredient to be combined therewith.

Medical composition for percutaneous administration

A termites trail-marking pheromone which is (3Z,6Z,8E)-dodecatrienol, and a composition which comprises (3Z,6Z,8E)-dodecatrienol as an essential component and another component which is a trail-marking pheromone-like substance, and a method of detecting termites by using this composition or (3Z,6Z,8E)-dodecatrienol.

Termites trail-following pheromone and a same composition and method of

A process for preparing methyl 4-oxo-5-tetradecynoate useful as an intermediate for synthesizing (R,Z)-5-dec-1-enyl-oxacyclopentan-2-one, which comprises reacting monomethyl succinate with an alkyl chlorocarbonate in the presence of a base to form an acid anhydride and reacting the acid anhydride with a Grignard reagent of 1-decyne. Methyl 4-oxo-5-tetradecynoate can be prepared in high yields at high purities by this process.

Process for preparing methyl 4-oxo-5-tetradecynoate

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Osaka, Japan

Tetsuo Omata