公开(公告)号：JPS61200996A

公开(公告)日：1986-09-05

申请号：JP4249185

申请日：1985-03-04

Applicant: AGENCY IND SCIENCE TECHN

Inventor： MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  ORIHASHI YUJI ,  KOBAYASHI NORIHISA ,  TSUCHIDA HIDETOSHI

IPC: C07F13/00 ,  C07F15/02 ,  C07F15/06 ,  C30B7/00 ,  C30B7/12 ,  C30B31/04 ,  C30B31/06 ,  G01N27/12 ,  H01B1/12 ,  H01L51/00 ,  H01L51/05 ,  H01L51/30 ,  H01L51/40

Abstract: PURPOSE:To obtain cyanometal phthalocyanine crystal having improved stability, molding properties and mechanical handleability and high electrical conductivity, by subjecting a solution containing a dicyanometal phthalocyanine alkali salt to electrolytic treatment. CONSTITUTION:A solution containing a dicyanometal phthalocyanine alkali salt [e.g., dicyanocobalt (III) phthalocyanine sodium salt, etc.] is subjected to electrolytic treatment, to precipitate dicyanometal phthalocyanine crystal. Preferably the prepared crystal is doped with at least one substance selected from an electron acceptive compound (e.g., I, Br, arsenic pentafluoride, etc.) and an electron donative compound (e.g., Li, Na, K, etc.).

公开(公告)号：JP2000298255A

公开(公告)日：2000-10-24

申请号：JP32025699

申请日：1999-11-10

Applicant: AGENCY IND SCIENCE TECHN ,  TAMAOKI NOBUYUKI ,  MATSUDA HIROO ,  RICOH KK ,  OKAMURA OIL MILL

Inventor： FUTAMURA YOSHIROU ,  SUGIMOTO HIROYUKI ,  TAMAOKI NOBUYUKI ,  MATSUDA HIROO ,  KIDA YOSHIE

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

Abstract: PROBLEM TO BE SOLVED: To provide a thermosensitive reversible recording medium, in which uniform reflected light or white display can be easily obtd. over the whole visible wavelength region without complicated operation, and to provide a method of reversible recording using the thermosensitive reversible recording medium. SOLUTION: This medium is produced by holding a recording layer composed of a thermosensitive recording material, consisting of a cholesteric liquid crystal compd. or a mixture of this compd. between two substrates at least one of which is transparent. This thermosensitive reversible recording medium enables thermosensitive reversible recording. In this method, interfaces which cause changes in the refractive index for light are formed randomly in a large number in the recording layer in a white display state, and uniform reflected light can be obtd. over the whole visible wavelength region.

公开(公告)号：JPH1180275A

公开(公告)日：1999-03-26

申请号：JP25590997

申请日：1997-09-04

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

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

IPC: G02F1/35 ,  C08F8/30 ,  C08F220/60 ,  C08F222/40 ,  G02F1/355 ,  G02F1/361

Abstract: PROBLEM TO BE SOLVED: To obtain a novel polymeric substance suppressed in the relaxation of an aligned structure at high temperatures and having good heat stability and secondary nonlinear optical properties by using an acrylamide copolymer comprising three types of repeating units having specified structures and having a specified weight-average molecular weight. SOLUTION: The acrylamide copolymer comprises repeating units represented by formula I, repeating units represented by formula II (wherein R is H or methyl; and R is H or methyl bonded in an o- or m-position) and repeating units represented by formula III (wherein R and R are as defined in formula II) and has a weight-average molecular weight of 50,000-300,000. This copolymer can be produced by radical-copolymerizing N-phenylmaleimide with N-(N-phenyl- N-methyl)aminoethylacrylamide and effecting the diazo coupling of the obtained copolymer with nitroaniline. The ratio of the compound of formula I to the compound of formula II is 2: 1 to 1:2 by mole.

公开(公告)号：JPH09227552A

公开(公告)日：1997-09-02

申请号：JP4274896

申请日：1996-02-29

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIMADA SATORU ,  MATSUDA HIROO ,  OKADA SHUJI ,  NAKANISHI HACHIRO

IPC: G03C1/73 ,  C07D339/06 ,  C08F38/02 ,  G02B1/04

Abstract: PROBLEM TO BE SOLVED: To obtain a new compound useful as a raw material for a functional material such as nonlinear optical material, photosensitive material, polymer semiconductor crystal, etc., having solid-phase polymerizability. SOLUTION: This diacetylene derivative is shown by formula I (Ar is a bifunctional aromatic group; (m) and (n) are each 2-12). The compound of formula I is obtained by reacting a 1,3-alkadiynecarboxylic acid amide compound of the formula, CH3 -(CH2 )m-C≡C-C≡C-(CH2 )n -CONH-Ar-COOH or its acid halide with hydroxymethyltetrathiafulvalene of formula II in an inert gas atmosphere (e.g. nitrogen gas) in a solvent (e.g. methylene chloride) at 0-50 deg.C. The 1,3-alkadiynecarboxylic acid amide compound is obtained by reacting an 1,3- alkadiynecarboxylic acid compound of the formula, CH3 -(CH2 )m - C≡C-C≡C-(CH2 )n -COOR (R is H or a halogen) with an aromatic aminocarboxylic acid ester of the formula, H2 N-Ar-COOR (R is a hydrocarbon) and hydrolyzing the ester bond.

公开(公告)号：JPH0822040A

公开(公告)日：1996-01-23

申请号：JP13183793

申请日：1993-06-02

Applicant: AGENCY IND SCIENCE TECHN ,  HODOGAYA CHEMICAL CO LTD

Inventor： MATSUDA HIROO ,  TOMIYAMA HIROMITSU

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

Abstract: PURPOSE:To obtain a new org. nonlinear optical material having high nonlinear optical characteristics and absorption of light in a visible region in a short wavelength region by using a specified pyrazine deriv. as a nonlinear optical material. CONSTITUTION:This optical material consists of a compd. expressed by formula I or II. In formula I, A, B may be same or different and are hydrogen atoms, substd. or unsubstd. alkyl groups or alkoxy groups, subtd. or unsubstd. aryl groups or aryloxy groups, substd. or unsubstd. alkylthio groups or arylthio groups, or halogen atoms. In formula II, R1, R2 may be same or different and are hydrogen atoms, substd. or unsubstd. alkyl groups or alkoxy groups, or subtd. or unsubstd. aryl groups or acetyl groups, and R1 and R2 may form a ring with each other. Further, C is a hydrogen atom, substd. or unsubstd. alkyl groups or alkoxy groups, or subtd. or unsubstd. aryl group or aryloxy groups.

公开(公告)号：JPH07233141A

公开(公告)日：1995-09-05

申请号：JP5133894

申请日：1994-02-23

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIMADA SATORU ,  MATSUDA HIROO ,  MINAMI SHINJI ,  OKADA SHUJI ,  NAKANISHI HACHIRO

IPC: C07C319/18 ,  C07C319/14 ,  C07C323/19

Abstract: PURPOSE:To obtain a diacetylene derivative which has an S atom directly bonded to a C atom in the triple bond and shows a large electronic effect and solid-phase polymerizability, thus is useful as a functional material such as a nonlinear optical material, a photosensitive material and a polymer semiconductor crystal. CONSTITUTION:The compound of formula I [Ar , Ar are (substituted) phenyl; n is 1-8], for example, 8-(4-bromophenyl)thio-5,7-octadiynyl phenylcarbamate. The compound of formula I is prepared by protecting the terminal hydroxy group in omega-hydroxy-1,3-alkadiyne of formula II, introducing an arylthio group into the 1-position of the protected omega-hydroxy-1,3-alkadiyne, deprotecting the product of the diacetylene derivative of formula III and allowing the deprotected hydroxyl to react with an aryl isocyanate to effect introduction of a urethane group on the chain terminal.

公开(公告)号：JPH03251566A

公开(公告)日：1991-11-11

申请号：JP4667390

申请日：1990-02-26

Applicant: TODA KOGYO CORP ,  AGENCY IND SCIENCE TECHN

Inventor： MATSUDA HIROO ,  OKADA SHUJI ,  MASAKI ATSUSHI ,  NAKANISHI HACHIRO ,  OSUGI MINORU ,  HORAI SHIGERU ,  HORIISHI NANAO

IPC: C07D209/86 ,  C07B61/00 ,  C07C15/48 ,  C07D401/06

Abstract: NEW MATERIAL:A compound of formula I [R is 2,5-or 3,5-bis(trifluoromethyl) phenyl, 4-aminophenyl or 2-pyridyl]. EXAMPLE:1-[2,5-bis(trifluoromethyl)phenyl]-5-(N-carbazolyl-1,3-pentadi yne. USE:Useful for functional materials such as nonlinear optical materials, photosensitive materials and polymeric semiconductor crystals. PREPARATION:An asymmetrical coupling is made between (A) an ethynylbenzene derivative of formula II and (B) N-(3-bromo-2-propynyl)carbazole of formula III into the objective compound of the formula I. The reaction is carried out in such a manner that an amine and copper chloride are added to a solution of the compound of the formula II followed by gradual addition of the compound of the formula III while stirring.

公开(公告)号：JPH01233263A

公开(公告)日：1989-09-19

申请号：JP5870688

申请日：1988-03-11

Applicant: AGENCY IND SCIENCE TECHN ,  TODA KOGYO CORP

Inventor： MATSUDA HIROO ,  OKADA SHUJI ,  NAKANISHI HACHIRO ,  KATO MASAO ,  HORAI SHIGERU ,  HORIISHI NANAO

IPC: C07C205/06 ,  C07C67/00 ,  C07C201/00 ,  C07C209/00 ,  C07C211/45 ,  C07C211/52 ,  C07C211/65 ,  C08G61/00 ,  C08G61/02 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

Abstract: NEW MATERIAL:A compound expressed by formula I (R1 is NO2 or NH2 and R2-R5 are H; R2 is NO2 or NH2 and R1, R3-R5 are H or R1 is NR2, R2 and R3 are H and R4 is NO2). EXAMPLE:1-(2-Nitrophenyl)butadiyne. USE:A nonlinear optical material, photosensitive material or high polymer semiconductor crystals, having great molecular polarization due to nitro group which is an electron attractive group or amino group which is an electron donative group, resulting in expectable great nonlinear optical effects. PREPARATION:A phenylicetylene derivative expressed by formula II and a 4-bromo-2-methyl-3-butyn-2-ol expressed by formula III are subjected to asymmetric coupling reaction to provide a phenyldiacetylene derivative expressed by formula IV, which is then subjected to acetone removing reaction in the presence of potassium hydroxide catalyst to afford the aimed compound expressed by formula I.

公开(公告)号：JPH0192727A

公开(公告)日：1989-04-12

申请号：JP12285188

申请日：1988-05-19

Applicant: AGENCY IND SCIENCE TECHN

Inventor： OKADA SHUJI ,  MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  SAMURA HIDEO

IPC: C09K3/00 ,  C07C67/00 ,  C07C209/00 ,  C07C211/52 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE:To obtain a nonlinear optical org. material which has the second harmonic waves generation as large as several times that of urea, is stable at room temp. and is easily growable to a large single crystal by using specific 4-amino-4'-nitrobiphenyl as said org. material. CONSTITUTION:The 4-amino-4'-nitrobiphenyl expressed by the formula I is the single crystal without having a symmetrical center and, therefore, exhibits the second harmonic wave generation (SGH) activity of several times that of urea and is stable at room temp. Said material generates the second harmonic waves (SHG) and generates green light of the wavelength (532mum) of half the wavelength of incident light when measurement is made by projection of Nd: YAG laser (wavelength = 1064mum, output 3mJ/pulse) in the powder state. This material is growable to a single crystal of mm order. The org. crystal which has the large SHG activity, is stable at room temp. and is easily growable to the large single crystal at need is thereby obtd. This crystal is adequate as a material for light wavelength conversion elements, optical shutters, high- speed optical switching elements and optical logical gates as well as the stock for optical transistors, etc.

公开(公告)号：JPS6368549A

公开(公告)日：1988-03-28

申请号：JP21333886

申请日：1986-09-10

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 ,  C07C233/07 ,  C07C233/13 ,  C07C233/15 ,  C07C233/43 ,  C07C233/54 ,  C07C233/56 ,  C07C235/72 ,  C07C235/74 ,  C07C239/00 ,  C07C269/00 ,  C07C271/20

Abstract: NEW MATERIAL:A compound expressed by formula I (n is 0-20; R is alkyl, alkenyl, alkynyl, aryl, alkaryl or aralkyl, provided that those groups contain at least one substituent selected from halogen, amide, urethane, ester and nitro). EXAMPLE:Eicosane di{3-[4-(3-nitrophenyl)butadienyl]anilide}. USE:A monomer having solid phase polymerizability and large electronic effect, and usable and large electronic effect and usable and a functional material such as non-linear optical material, photosensitive material, high polymer semi conductor crystal, etc., as well as cast film. PREPARATION:A diphenyl diacetylene derivative expressed by formula III obtained by subjecting a bromoethynyl derivative expressed by formula II to asynmetric coupling reaction with 3-ethyl aniline in a solvent in the presence of a copper salt catalyst such as copper (I) chloride, etc., is reacted with a dicarboxylic acid dichloride expressed by formula IV in the presence of an amine to provide a compound expressed by formula I.