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公开(公告)号:JPH045635A
公开(公告)日:1992-01-09
申请号:JP10712190
申请日:1990-04-23
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , OSUGI MINORU , HORAI SHIGERU
Abstract: PURPOSE:To obtain the above optical material having a high nonlinear optical characteristic by forming a supporting film consisting of a synthetic resin which can be dissolved in a common solvent for a diacetylene compd. and the diacetylene compd. which is subjected to solid phase polymn. therein to mixing ratios of a prescribed range. CONSTITUTION:This optical material consists of the supporting film consisting of the synthetic resin which can be dissolved in the common solvent for the diacetylene compd. and the diacetylene compd. which is subjected to the solid phase polymn. therein. The mixing ratios based on the volume of the supporting film and the diacetylene compd. are specified to a 5:1 to 1:20 range. Polystyrene, polyvinyl chloride, etc., which are soluble in the common solvent for the diacetylene compd. are used as the synthetic resin to be used in this embodiment. Hexadiindiol-P-toluene sulfonite, etc., are usable as the solid phase polymerizable acetylene compd. The material which is the material having the nonlinear optical characteristic, having optical uniformity, transparency and easy workability including the formation of thinner films, and is the excellent stability with lapse of time is obtd. in this way.
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公开(公告)号:JPH03273218A
公开(公告)日:1991-12-04
申请号:JP7211490
申请日:1990-03-23
Applicant: AGENCY IND SCIENCE TECHN , OMRON TATEISI ELECTRONICS CO
Inventor: OKADA SHUJI , MASAKI ATSUSHI , MATSUDA HIROO , NAKANISHI HACHIRO , SAKAI KOJI , OMI TOSHIHIKO , KOIKE TOMOYUKI , YOSHIKAWA NORIO
IPC: G02F1/35 , C07D213/57 , G02F1/355 , G02F1/361
Abstract: PURPOSE:To increase the transmissivity of blue light and a nonlinear optical constant by providing an org. material composed of specific p-toluene sulfonic acid 1-methyl-4-(2-(4-cyanophenyl)vinyl)pyridinium. CONSTITUTION:This org. material for nonlinear optics consists of the p-toluene sulfonic acid 1-methyl-4-(2-(4-cyanophenyl)vinyl)pyridinium expressed by formula I. The p-toluene sulfonic acid 1-methyl-4-(2-(4-cyanophenyl)vinyl)pyridinium is a single crystal without having a symmetrical center and exhibits the SHG activity of several times the SHG activity of urea. In addition, the light absorption end in the crystal is as shorter in wavelength as about
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公开(公告)号:JPH03249742A
公开(公告)日:1991-11-07
申请号:JP4879390
申请日:1990-02-28
Applicant: AGENCY IND SCIENCE TECHN , TOYO INK MFG CO , RIKAGAKU KENKYUSHO
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , SUDA YASUMASA , EHASHI SHIGEYUKI , SHIGEHARA JUNKO , YAMADA AKIRA
IPC: G02F1/35 , C07D487/22 , G02F1/355 , G02F1/361
Abstract: PURPOSE:To exhibit the nonlinear optical characteristic equiv. to or higher than the nonlinear optical characteristic of org. nonlinear optical materials and to solve the problems, such as difficulty in thin film formation and unstability to air, heat, etc., intrinsic to existing org. materials at the time of practical use by incorporating at least one kind of specific phthalocyanine derivatives as components into the above material. CONSTITUTION:This material contains at least one kind of the phthalocyanines expressed by formula I. In the formula I, R denotes 2 to 24C aliphat. hydrocarbon group; M denotes a metal atom which may contain a halogen atom or oxygen atom or a hydrogen atom. The org. nonlinear optical material having a cubic nonlinear sensitivity equiv. to or higher than the cubic nonlinear sensitivity of the org. nonlinear optical materials is obtd. and has extremely stable heat resistant stability in the air; in addition, the maintenance and handling are facilitated.
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公开(公告)号:JPH02245607A
公开(公告)日:1990-10-01
申请号:JP6692989
申请日:1989-03-17
Applicant: AGENCY IND SCIENCE TECHN
Inventor: OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO
IPC: G01B15/02
Abstract: PURPOSE:To enable measurement of the thickness of a thin film in a noncontact manner with a thin film sample and handily while the thin film is being made by irradiating an organic thin film with X-rays at an angle of incidence to determine a maximal value of an intensity of X-rays at a position of an angle of reflection. CONSTITUTION:An apparatus herein used is such that is used when a normal reflection X-ray diffraction is measured and it is provided with a goniometer mechanism in which an X-ray detector is positioned in a direction of reflection angle theta, namely, in a direction of angle 2theta to incidence of X-rays when an angle of a plane of a thin film is theta with respect to a direction of incidence of X-rays. In an apparatus of such a type, theta is swept continuously to perform a recording in a relationship between an angle 2theta of the detector and a detection intensity of X rays. At this point, as some peaks are noted continuously, values of 2theta of this series of peaks are read out. Then, a film thickness is calculated using an expression II derived from a Bragg's reflection formula (formula I). In this manner, values of film thicknesses obtained for the peaks are averaged or averaged being weighted statistically to determine a film thickness.
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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:JPH02297529A
公开(公告)日:1990-12-10
申请号:JP11213390
申请日:1990-04-27
Applicant: AGENCY IND SCIENCE TECHN
Inventor: OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , MURAMATSU RYOJI
IPC: G02F1/35 , C07D213/38 , G02F1/355 , G02F1/361
Abstract: PURPOSE:To increase SHG and to contrive the stability at room temp. by consisting the above material of specific p-toluene sulfonic acid.1-methyl-4-[2-(4- N, N-dimethylaminophenyl)vinyl] pyridinium. CONSTITUTION:This material consists of the p-toluene sulfonic acid.1- methyl-4-[2-(4-N, N-dimethylaminophenyl)vinyl] pyridinium expressed by formula I. The p-toluene sulfonic acid.1-methyl-4-[2-(4-N, N-dimethylaminophenyl)vinyl] pyridinium can be grown to a large single crystal by a slow evaporation method. The org. crystal which has the large second harmonic wave generation (SHG) activity, is stable at room temp., and can be easily grown to the large single crystal at need is obtd. in this way.
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公开(公告)号:JPH02215742A
公开(公告)日:1990-08-28
申请号:JP3702089
申请日:1989-02-16
Applicant: AGENCY IND SCIENCE TECHN , TODA KOGYO CORP
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , KATO MASAO , OSUGI MINORU , HORAI SHIGERU , HORIISHI NANAO
IPC: G02F1/35 , C07C43/225 , C07C211/29 , C07C211/52 , C08F38/00 , C08F138/00 , G02F1/355 , G02F1/361
Abstract: NEW MATERIAL:A diphenyldiacetylene derivative expressed by formula I (R1 is H or CH3O; R2 is H, CH3O or CH3NH; R3 and R4 are H or CF3) and having solid-phase polymerizability. EXAMPLE:1-(4-Methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-but adiyne. USE:A functional material, such as nonlinear optical material, photosensitive material or polymer semiconductor crystals. PREPARATION:An ethynylbenzene derivative formula formula II and 1-bromo-3- hydroxy-3-methyl-1-butyne expressed by formula III are subjected to asymmetric coupling and the resultant diacetylene derivative expressed by formula IV is subjected to removal of acetone in the presence of a basic catalyst to provide a phenylbutadiyne derivative expressed by formula V, which is then subjected to coupling reaction with bis(trifluoromethyl)iodobenzene expressed by formula VI in the presence of a palladium catalyst to afford the compound expressed by formula I.
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公开(公告)号:JPH0212133A
公开(公告)日:1990-01-17
申请号:JP16191588
申请日:1988-06-29
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO , KATO MASAO
Abstract: PURPOSE:To improve stability with age by mixing a high-polymer electrolyte soln. and an ionic dye soln. to form the composite of the high-polymer electrolyte and the ionic dye. CONSTITUTION:The composite of the high-polymer electrolyte and the ionic dye is formed by mixing the high-polymer electrolyte soln. and the ionic dye soln. The composite of the high-polymer electrolyte and the ionic dye is bonded by the electrostatic interaction between the residual ion groups possessed by the same and, therefore, the composite contains the ionic dye at the high concn. from several ten to hundred mol% per residual ionic group of the high-polymer electrolyte. The composite can be easily made into a cast film by dissolving the same into water, polar solvent such as alcohol, or a solvent contg. inorg. ions such as sodium chloride or acid and alkalis such as hydrochloric acid and sodium hydroxide therein. This cast film is optically uniform and transparent and the dye molecules therein are bonded to each other by the electrostatic interaction. Isotropy is obtd. in this way and the stability with age is improved.
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公开(公告)号:JPH01233274A
公开(公告)日:1989-09-19
申请号:JP5870788
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 , KINOSHITA MINORU , SUGANO TADASHI , NOZAWA KIYOKAZU
IPC: C07D211/94 , C08F38/00
Abstract: NEW MATERIAL:A diacetylene derivative expressed by formula I (X is NH or O; m is 8-20; n is 4-20). EXAMPLE:4-(10,12-Pentacosadiynylcarbonylamino)-2,2,6,6-tetramethylpipe ridine-1- oxy. USE:A diacetylene monomer, capable of forming paramagnetic polydiacitylene crystals in 100% radical concentration and utilized as a standard marker, antioxidant, radical scavenger, etc., since the monomer has stable radicals and exhibits solidphase polymerizability. PREPARATION:A diacetylenecarboxylic acid compound expressed by formula II and a stable radical compound expressed by formula III are subjected to dehydrating condensation reaction using dicylohexyldicarbodiimide to afford the aimed compound expressed by formula I.
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