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公开(公告)号:JPS6393375A
公开(公告)日:1988-04-23
申请号:JP24025286
申请日:1986-10-09
Applicant: AGENCY IND SCIENCE TECHN , SANESU KEISOKU KK
Inventor: NAKANISHI HACHIRO , OKADA SHUJI , MATSUDA HIROO , KATO MASAO , HARA KATSUHEI , ONO NOBUAKI
Abstract: PURPOSE:To easily achieve the mass production of a precise composite built-up film, by partitioning the surface of the water in a water tank into a plurality of sections by providing a fixed plate to the water surface part of the water tank and using a lifter capable of independently supporting a film forming solid substrate in a gaseous phase and a liquid phase. CONSTITUTION:A lifter for preparing a composite built-up film is equipped with an upper arm 5 for supporting a solid substrate 10 in a gaseous phase to move left and right as well as up and down and a lower arm 6 for supporting the solid substrate 10 in a liquid phase to move left and right as well as up and down. At first, in such a state that the solid substrate 10 is mounted to the gripper 4 of the upper arm 5, A-molecules are developed on the left water surface 9-1 partitioned of a fixed plate barrier 2 of a water tank 1 and B-molecules are developed on the right water surface 9-2 and monomolecules are arranged by a movable plate barrier 3. Thereafter, the solid substrate 10 is transferred from the upper arm 5 to the lower arm 6 on the side of the left water surface 9-1 and both arms 5, 6 are rotated by 180 deg. around a support jig 7 and, now, the solid substrate 10 is transferred from the lower arm 6 to the upper arm 5 to successively build up monomolecular films A, B when passes the respective water surfaces.
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公开(公告)号:JPS62255475A
公开(公告)日:1987-11-07
申请号:JP9595286
申请日:1986-04-25
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , KATO MASAO , HORAI SHIGERU
Abstract: NEW MATERIAL:A diacetylene compound of formula I (R is hydroxymethyl, 4-hydroxybutyl or their toluenesulfonic acid ester or phenyl-carbamic acid ester). EXAMPLE:1-(N-carbazoline)-5-hydroxy-1,3-pentadiyne. USE:Useful as a monomer for forming a polymeric semiconductor crystal or a polymer crystal exhibiting singular optical characteristics. Polydiacetylene crystal has excellent electrical and optical properties. The solid-phase polymerization of the monomer can be carried out by the heating, gamma-ray irradiation, etc., of a crystal sealed in a glass tube in vacuum or in an inert gas atmosphere. PREPARATION:The compound of formula I can be produced e.g. by asymmetric coupling of N-ethynylcarbazole of formula II with a 1-bromopropyn-3-ol of formula III (n is 1 or 4).
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公开(公告)号:JPH11322685A
公开(公告)日:1999-11-24
申请号:JP14214298
申请日:1998-05-08
Applicant: AGENCY IND SCIENCE TECHN , MATSUDA HIROO , FUKUDA TAKASHI
Inventor: MATSUDA HIROO , FUKUDA TAKASHI , KIMURA TATSUMI , KATO MASAO , OKADA SHUJI , NAKANISHI HACHIRO
IPC: G02F1/35 , C07C227/18 , C07C229/60 , C07C253/30 , C07C255/55 , C07C323/62 , G02F1/355 , G02F1/361
Abstract: PROBLEM TO BE SOLVED: To obtain a novel compound that has a good level of optical transparency and the secondary nonlinear optical property and is useful as an organic secondary nonlinear optical material. SOLUTION: This novel compound is represented by formula I (X is a dialkylamino, an alkylthio; Y is nitro or cyano; n is 1-3), typically the compound of formula II. The compound of formula I is prepared by reaction of an aromatic carboxylic halide of formula III (Hal is a halogen), for example, 4- dimethylaminobenzoyl chloride, with a p-substituted phenol, for example, 4- cyanophenol or the like in the presence of a hydrogen halide acceptor in an inert solvent such as acetone and the like.
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公开(公告)号:JPH11255757A
公开(公告)日:1999-09-21
申请号:JP5536598
申请日:1998-03-06
Applicant: AGENCY IND SCIENCE TECHN , SHIMADA SATORU , MATSUDA HIROO
Inventor: SHIMADA SATORU , MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO
IPC: C07D273/01 , G02F1/35 , G02F1/355 , G02F1/361
Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound having crown ether structure, high in ion transfer ability, capable of solid phase polymerization, and useful as a raw material for functional materials such as electroconductive materials, electrode materials, nonlinear optical materials, photosensitive materials and semiconductor crystals. SOLUTION: This new compound is shown by the formula CH3 -(CH2 )k -C≡C- C≡C-(CH2 )m -CO- E [(k) and (m) are each 1-12; E is a structure of the formula ((n) is 1-4)], e.g. CH3 -(CH2 )11 -C≡C-C≡C-(CH2 )8 -COOH. This new compound of the above formula is obtained by reaction of a 1,3-alkadiynecarboxylic acid compound of the formula CH3 -(CH2 )k -C≡C-C≡C-(CH2 )m -COX (X is hydroxyl or a halogen) with an azacrown compound of the formula H-E pref. at 1.1-1.2 mol per mol of the 1,3-alkadiynecarboxylic acid compound in an aprotic solvent (e.g. methylene chloride, an ether compound) in an inert gas atmosphere such as argon or nitrogen under normal pressures pref. at 25-40 deg.C under agitation.
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公开(公告)号:JPH1121272A
公开(公告)日:1999-01-26
申请号:JP13437198
申请日:1998-04-28
Applicant: AGENCY IND SCIENCE TECHN , MATSUDA HIROO , FUKUDA TAKASHI
Inventor: MATSUDA HIROO , FUKUDA TAKASHI , YAMADA SHINJI , KIMURA TATSUMI , KATO MASAO , DAN NOBUAKI , OKADA SHUJI , NAKANISHI HACHIRO
IPC: G02F1/35 , C07C67/14 , C07C69/92 , C07C69/94 , C07C201/12 , C07C205/43 , C07C255/01 , C07C255/38 , C07C255/55 , C07C317/22 , G02F1/355 , G02F1/361
Abstract: PROBLEM TO BE SOLVED: To obtain the subject new compound excellent in secondary nonlinear optical characteristics, having excellent optical transparency. SOLUTION: This compound is that one expressed by formula I [R is a lower alkyl; R is perfluoroalkyl, cyano, nitro, 2,2-dicyanoethenyl or methylsulfonyl; (n) is 1-3], e.g. 4-anisic acid 4-cyanophenyl-ester. The compound of formula I is obtained by adding p-substituted phenol expressed by formula III little by little into a solvent contg. an aromatic carboxylic halide expressed by formula II (X is a halide) at room temperature or under iced conditions, reacting with each other in the presence of a hydrogen halide catcher (e.g. a tertiary amine, such as trimethylamine, triethylamine, pyridine), preferably, in an inert solvent (e.g. acetone, methylethylketone, diethylether) for 1-30 hrs., washing the resulting product with water and separating the organic layer to remove the solvent.
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公开(公告)号:JPH0679168A
公开(公告)日:1994-03-22
申请号:JP23816092
申请日:1992-09-07
Applicant: KASAI HITOSHI , OIKAWA HIDETOSHI , ONO KATSUMICHI , NAKANISHI HACHIRO , HITACHI LTD , AGENCY IND SCIENCE TECHN
Inventor: KASAI HITOSHI , OIKAWA HIDETOSHI , ONO KATSUMICHI , NAKANISHI HACHIRO , OKADA SHUJI , MATSUDA HIROO , MINAMI SHINJI , HARI SHINGU NARUWA , TSUNODA ATSUSHI , KOBI AKIO
Abstract: PURPOSE:To prepare a superfine particle wherein mol.wt., degree of crystalinity, etc., are controlled in accordance with the use by mixing a soln. of an org. material dissolved in a good solvent in a poor solvent for the org. material being compatible with this solvent and preparing an org. superfine particle consisting of a crystal or an associated body with a specified particle diameter or smaller. CONSTITUTION:A functional org. material such as a conjugated molecule with a pi atom conjugated system and a color element molecule is dissolved in a good solvent such as ethanol. Then, the soln. is mixed in a poor solvent which is compatible with this solvent and is a poor solvent for the org. material, such as water to prepare an org. superfine particle with a particle diameter of at most 1mum consisting of a crystal or an associated body. By treating like this, the good solvent dissolving the sample is dispersed as a droplet after it is mixed in the poor solvent and with evaporation gradually, the droplet loses the solvent to make a supersaturated condition and a fine crystal is finally deposited.
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公开(公告)号:JPH02281047A
公开(公告)日:1990-11-16
申请号:JP10023689
申请日:1989-04-21
Applicant: AGENCY IND SCIENCE TECHN , MITSUI TOATSU CHEMICALS
Inventor: OKADA SHUJI , MATSUDA YASUO , NAKANISHI HACHIRO , KATO MASAO , ABE KOJI , ITO HIROSHI
IPC: G02F1/35 , B05D1/20 , B29K9/00 , B29L31/34 , B32B9/00 , B32B27/08 , C08J5/18 , C09K11/06 , G02F1/355 , G02F1/361
Abstract: PURPOSE:To obtain the subject high-quality thin film useful as a material for electronic optical element to be used under a strong electric field of laser, etc., having excellent optical properties by mutually laminating an organic low molecular or polymer thin film and an organic polymer amorphous thin film. CONSTITUTION:For example, a compound provided with polarity by introducing a hydrophobic and a hydrophilic groups to an organic compound such as diacetylene derivative by using L.B method is dissolved in a solvent such as benzene in 10 to 5X10 mol/l, dripped into clear water or clear water containing cadmium chloride or potassium hydrogencarbonate and the organic low-molecular or polymer thin film extended on water surface is formed on a silicon plate, etc. Then an organic polymer amorphous thin film is formed from an organic polymer compound such as (meth) acrylic acid alkyl ester polymer on the polymer thin film by the same method and the organic low molecular or polymer thin film and the organic polymer amorphous thin film are mutually laminated to give the aimed complex thin film having preferably
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公开(公告)号:JPH01249830A
公开(公告)日:1989-10-05
申请号:JP7967388
申请日:1988-03-31
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , KATO MASAO , MICHIHASHI TAKAHISA , INOUE TAKAHITO , YATSUSE KIYOSHI , OKADA MASAKAZU
IPC: C08G69/28 , C08F290/00 , C08F299/00 , C08G69/48
Abstract: PURPOSE:To obtain the subject crystal having isotropically high strength, by orienting a specific alkyldiamine perpendicularly on a surface of a substrate, depositing a diamine and a diacetylenedicarboxylic acid by vacuum evaporation and irradiating with ultraviolet ray, etc., to effect the solid-phase polymerization. CONSTITUTION:(A) An alkyldimine of formula I (n is 8-18) (e.g., diaminodecane) is deposited on (B) a substrate such as polished glass plate by vacuum evaporation at a heating temperature of the component A of 30-110 deg.C, a substrate temperature of -30-10 deg.C and a vacuum degree of 10 -10 Torr. Thereafter, (C) a diamine of formula II (R is alkyl, aryl, etc.) and (D) a diacetylenedicarboxylic acid of formula III (R is alkyl, aralkyl, etc.) are deposited on the surface by vacuum evaporation, polymerized and then irradiated with ultraviolet ray or ionizing radiation (e.g., gamma-ray of cobalt 60) to effect the solid-phase polymerization and obtain the objective crystal.
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公开(公告)号:JPH01233247A
公开(公告)日:1989-09-19
申请号:JP5917388
申请日:1988-03-12
Applicant: AGENCY IND SCIENCE TECHN
Inventor: OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , OTSUKA MASAAKI
IPC: C07C205/19 , C07B61/00 , C07C27/00 , C07C29/44 , C07C33/28 , C07C33/30 , C07C33/48 , C07C51/00 , C07C57/42 , C07C57/60 , C07C67/00 , C07C201/00 , C07C205/20 , C07C205/56 , C07C213/00 , C07C215/68 , C07C227/00 , C07C229/44 , C08F38/02 , C07C79/22 , C07C79/46 , C07C91/40 , C07C99/00 , C07C101/28
Abstract: NEW MATERIAL:A compound shown by formula I-II [R1 is phenyl which may contain one substituent group (CH3, CF3, NO2 or N,N-dimethylamino) at 2-4 position, 9-anthryl, pentafluorophenyl, 2,5- or 3,5-bis(trifluoromethyl) phenyl or 2-amino-5-nitrophenyl; R2 is each group in R1 except phenyl and 4-tolyl; m is 15-20; n is 14-24]. EXAMPLE:27-Phenylheptacosa-24,26-diin-1-ol. USE:Since the compound shown by the formula I-II has polymerizing properties in a solid state and can be made into a accumulated film, the compound can be processed into a high-performance nonlinear optical material, sensitized material and polymer semiconductor crystal. The compound is structurally a nonlinear type and an aromatic compound whose substituent group is conjugated with triple bond of diacetylene so that the compound is useful as a diacetylene monomer having large nonlinear optical effects because of high electronic effects. PREPARATION:A compound shown by formula R1-I is reacted with a compound shown by formula III to give a compound shown by formula I.
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公开(公告)号:JPS62255459A
公开(公告)日:1987-11-07
申请号:JP9595586
申请日:1986-04-25
Applicant: AGENCY IND SCIENCE TECHN , TODA KOGYO CORP
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , KATO MASAO , HORAI SHIGERU , HORIISHI NANAO
IPC: C08F38/00 , C07C67/00 , C07C231/00 , C07C233/15
Abstract: NEW MATERIAL:A compound of formula I [either one of R1-R3 is -NHCO-(CH2)n-CH3 (n is 12-18) and the others are H]. EXAMPLE:1-(3-Nitrophenyl)-4-(2-heptadecylcarbamoylphenyl)-1,3-butadiyne. USE:Useful as a monomer of diacetylene compound for forming a nonlinear optical material, a photo-sensitive material or a polymeric semiconductor material. It is polymerizable in solid phase and is an aromatic compound having asymmetric structure and having substituent group conjugating with the triple bond of diacetylene. It has high electronic effect. PREPARATION:The compound of formula I can be produced by carrying out asymmetric coupling of 3-(bromoethynyl)nitrobenzene of formula II with an ethynylaniline of formula III (one of R1-R3 is amino and the others are H) and reacting the resultant compound of formula I (one of R1-R3 is amino and the others are H) with carboxylic acid chloride of formula IV in the presence of an amine.
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