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.

公开(公告)号：JPH11100386A

公开(公告)日：1999-04-13

申请号：JP26457397

申请日：1997-09-29

Applicant: AGENCY IND SCIENCE TECHN ,  SHIMADA SATORU ,  ONISHI SATOMI ,  MATSUDA HIROO ,  NAKANISHI FUSAE

Inventor： SHIMADA SATORU ,  ONISHI SATOMI ,  MATSUDA HIROO ,  NAKANISHI FUSAE ,  TAKEDA HIROYUKI

IPC: C07F7/08

Abstract: PROBLEM TO BE SOLVED: To obtain a sulfide compound useful as a nonlinear optical material or the like and usable as a stable thiol equivalent by reacting a specific compound with an organic metal compound. SOLUTION: This sulfide compound is a compound of formulas I to III [R , R , R and R are each an aryl or an (un)saturated aliphatic group; R is a lower alkyl; Ar is an aryl], e.g. (trimethylsilylethyl)phenylacetylene sulfide. The compound is obtained by reacting a tri(lower alkyl)silylethylsulfenyl compound of formula IV (X is a halogen or p-toluenesulfonyl) with an organic metal compound of formula V or VI [M is an alkali(alkaline earth) metal] or the formula R -M (R is the same as R or the like).

公开(公告)号：JPH1167591A

公开(公告)日：1999-03-09

申请号：JP23902097

申请日：1997-08-20

Applicant: AGENCY IND SCIENCE TECHN ,  FUKUDA TAKASHI ,  MATSUDA HIROO

Inventor： FUKUDA TAKASHI ,  MATSUDA HIROO ,  KATO MASAO ,  NAKANISHI HACHIRO

IPC: B32B17/10 ,  G02F1/061 ,  G02F1/361 ,  H01G7/02

Abstract: PROBLEM TO BE SOLVED: To provide an electret having high secondary non-linear optical characteristics by a method wherein the electret consists of a polar high- molecular thin film, which is formed on a glass substrate and is turned into an electret, and the electric resistance value between the surface and the rear of the glass substrate is set in a specified range. SOLUTION: A polar high-molecular thin film is formed on the surface of a glass substrate, the electric resistance value between the surface and the rear of which is in a range of satisfy 0.8Ω0

公开(公告)号：JPH1124027A

公开(公告)日：1999-01-29

申请号：JP14055198

申请日：1998-05-07

Applicant: AGENCY IND SCIENCE TECHN ,  TAMAOKI NOBUYUKI ,  MATSUDA HIROO

Inventor： TAMAOKI NOBUYUKI ,  ALEXANDER PARFENOV ,  MASAKI ATSUSHI ,  MATSUDA HIROO

IPC: G02F1/13 ,  B41M5/26 ,  B41M5/36 ,  C09K19/36

Abstract: PROBLEM TO BE SOLVED: To provide a thermosensitive recording medium which has full-color recording and rewritable characteristics made compatible with each other and an image forming method. SOLUTION: This rewritable color image recording medium provided with a thermosensitive layer containing a cholesteric liquid crystal compound which has =35 deg.C glass transition temperature is provided between two substrates, at least one of which is transparent. An image is formed by varying the temperature of the rewritable color image recording medium from 1st temperature to 2nd temperature (the cholesteric liquid crystal compound forms a cholesteric liquid phase at least one of the 1st temperature and 2nd temperature) according to the desired image, and then fixed by rapidly cooling the recording medium so that the thermosensitive layer is cooled to the glass transition temperature or below.

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.

公开(公告)号：JPH0869023A

公开(公告)日：1996-03-12

申请号：JP20653694

申请日：1994-08-31

Applicant: AGENCY IND SCIENCE TECHN

Inventor： TAMAOKI NOBUYUKI ,  MATSUDA HIROO ,  SEKI TAKAHIRO ,  YAMAOKA TSUGIO ,  HASEGAWA HIROSHI

IPC: G02F1/35 ,  C09K9/02 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE: To control nonlinear optical characteristics in a two-dimensional space at a fast rate by light by incorporating a compd. showing reversible or irreversible changes in absorption of light by irradiation of light or combination of irradiation of light and heat treatment into a polymer matrix in a specified proportion. CONSTITUTION: A compd. (photochromic compd.) showing reversible or irreversible changes in absorption of light by irradiation of light or combination of irradiation of light and heat treatment is incorporated by 30-90wt.%, preferably 40-70wt.% of the total nonlinear optical material into a polymer matrix. As for the photochromic compd. for example, spiropyran, fulgide, azobenzene, spirooxazine, diarylethene, deriv. of these, combination of biimidazole deriv. and leuco dye, or combination of org. halogen compd. and leuco dye can be used.

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

IPC: B01J19/00 ,  B01J19/12 ,  C07B63/00 ,  C08F2/18 ,  C08F2/48 ,  C08F6/00 ,  C08F38/00

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.

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.

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.

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.