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公开(公告)号:JPS63221115A
公开(公告)日:1988-09-14
申请号:JP5343287
申请日:1987-03-09
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , NAKANISHI HACHIRO , TANAKA YOSHIO , NAKAYAMA KAZUO , KATO MASAO
Abstract: PURPOSE:To produce a high-hardness plastic molding having a two-dimensional covalent bond-containing network structure, being highly crystalline and excellent in hardness and modulus, by polymerizing a diacetylenic nylon salt compound by heating in a mold under a high pressure. CONSTITUTION:A high-hardness plastic molding is produced by packing a diacetylenic nylon salt compound of formula I [wherein R1 and R2 are each a (substituted)alkylene, cycloalkylene or arylene] into a mold of any desired shape and polymerizing it by heating at 100-400 deg.C and 0.5X10 -15X10 atm. A highly crystalline plastic molding in the form of a two-dimensional covalent bond-containing network can be easily produced. This molding has excellent strength and modulus and such a high hardness as to be equivalent to that of a metal, so that it is very useful as a light high-hardness material. The compound of formula I can be quantitatively obtained as a crystalline form by mixing equimolar amounts of a diacetylenecarboxylic acid of formula II (wherein R1 is as defined above) and a diamine of formula III (wherein R2 is as defined above).
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公开(公告)号:JPS6363635A
公开(公告)日:1988-03-22
申请号:JP20871486
申请日:1986-09-04
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO
IPC: C07C57/18 , C07C57/42 , C07C57/48 , C07C57/52 , C07C63/66 , C07C67/00 , C07C201/00 , C07C205/43 , C07C211/62 , C07C217/90 , C07C233/78 , C08F38/00 , C08F290/00 , C08F299/00 , C08G69/26
Abstract: NEW MATERIAL:A diacetylene nylon salt compound of formula I (R1 and R2 are alkylene or arylene which may have one or more halogen, cyano, alkyl, aryl, nitro, ether, ester, amide, hydroxyl, carbonyl or sulfonyl groups). USE:Useful as a high-strength polymeric material. A crosslinked two-dimensional polymer crystal having completely oriented rigid polydiacetylene chain and completely oriented polyamide chain forming a hydrogen bond can be produced by solid-phase polymerization and solid-phase polycondensation. PREPARATION:The compound of formula I can be produced stoichiometrically as a precipitated crystal by mixing a diacetylenecarboxylic acid of formula II with equimolar amount of a diamine of formula III. When both compounds of formula II and formula III are liquid, the compounds are mixed with each other as it is and when the compounds are solid or liquid, an organic solvent such as methanol is used in the mixing operation.
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公开(公告)号:JPS62255460A
公开(公告)日:1987-11-07
申请号:JP9595686
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 [one of R1 and R2 is nitro and the other is H; either one of R1'-R3' is -NHCO-(CH2)n-CO2H (n is 6-18) and the others are H]. EXAMPLE:2-(4-(3-Nitrophenyl)-1,3-butadiynyl)phenylcarbamoylnonadecanoic acid. 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 can form a built-up film. It has an asymmetric structure and high electronic effect. PREPARATION:The compound of formula I can be produced by carrying out asymmetric coupling of bromoethynylnitrobenzene of formula II with an ethynylaniline of formula III and reacting the resultant compound of formula I (one of R1'-R3' is amino and the others are H) with an alkyldicarboxylic acid monochloride of formula IV in the presence of an amine.
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公开(公告)号:JPS61205241A
公开(公告)日:1986-09-11
申请号:JP4705185
申请日:1985-03-08
Applicant: AGENCY IND SCIENCE TECHN
Inventor: OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , SAMURA HIDEO
IPC: G03C1/72 , C07C67/00 , C07C209/00 , C07C211/52
Abstract: NEW MATERIAL:A compound shown by the formula I (R is H, or methyl; R is 10-20C straight-chain alkyl). EXAMPLE:N-Octadecyl-2-methyl-4-nitroaniline. USE:Useful for producing an optical element having highly active laser. PREPARATION:A 4-nitroaniline shown by the formula II or 2-methyl-4- nitroaniline is reacted with an alkylating agent shown by the formula X-R (X is strong acid residue) in the presence of an alkali (e.g., Na, K, NH3, pyridine, etc.), to give a compound shown by the formula I. An alkyl chloride, alkyl bromide, etc., may be cited as the alkylating agent. The compound shown by the formula I is useful for forming an accumulated film having a functional group showing specifically optical characteristics.
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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.).
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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.
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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.
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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.
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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.
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公开(公告)号:JPS6259934A
公开(公告)日:1987-03-16
申请号:JP19970585
申请日:1985-09-10
Applicant: AGENCY IND SCIENCE TECHN
Inventor: OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , SAMURA HIDEO
IPC: G02F1/35 , C07C211/42 , G02F1/313 , G02F1/355 , G02F1/361
Abstract: PURPOSE:To obtain the titled material having a large 2nd high frequency generating capacity (SHG) and a high stability at a room temp. and a large-sized monocrystal by incorporating a specific org. compd. to the titled material. CONSTITUTION:The titled material comprises a 2-amino fluorenone shown by formula I or a 4-amino-4'-nitrobiphenyl shown by formula II. The prescribed compds. may grow to the large monocrystal by a slow evaporation method. The prescribed compds. has a SHG larger than that of an urea by few times and has a good stability at the room temp. and may be easily grown to the large monocrystal. Thus, the titled material is used for materials of an optical wavelength conversion element, an optical shutter, a high switching element, a optical logical gate and an phototransistor.
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