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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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公开(公告)号:JPH11322690A
公开(公告)日:1999-11-24
申请号:JP14213298
申请日:1998-05-08
Applicant: AGENCY IND SCIENCE TECHN , FUKUDA TAKASHI , MATSUDA HIROO
Inventor: FUKUDA TAKASHI , MATSUDA HIROO , MIYAJI YOJI , KATO MASAO , NAKANISHI HACHIRO
IPC: G02F1/35 , C07C245/08 , G02F1/355 , G02F1/361
Abstract: PROBLEM TO BE SOLVED: To produce a new divinyl compound capable of forming a three- dimensional network structure capable of manifesting high secondary nonlinear optical characteristics and useful as an organic secondary nonlinear optical material by carrying out a photopolymerization while applying an electrical field. SOLUTION: This compound is represented by formula I [R is H or methyl; R is a lower alkyl; (n) is 4-8], e.g. 4-biphenylphenyl 4'-[N-(6- methacryloyloxyhexyl)-N-methylamino]-azobenzene-4-carboxylate. The compound represented by formula I is produced by reacting a compound represented by formula II (e.g. N-methacryloyloxyhexyl-N-methylaniline) with 4-aminobenzoic acid and a nitrite such as sodium nitrite, forming an azo compound represented by formula III e.g. 4'-[N-(6-methacryloyloxyhexyl)-N-methylamino]-azobenzene-4- carboxylic acid}, then converting the resultant compound into an acid halide and subsequently reacting the prepared acid halide with p-vinylphenol.
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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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公开(公告)号:JPH0192230A
公开(公告)日:1989-04-11
申请号:JP5615087
申请日:1987-03-11
Applicant: AGENCY IND SCIENCE TECHN
Inventor: MATSUDA HIROO , NAKANISHI HACHIRO , TANAKA YOSHIO , NAKAYAMA KAZUO , KATO MASAO
Abstract: PURPOSE:To easily obtain the titled molded article composed of a highly crystalline polymer having a network structure containing two-dimensional covalent bond, by carrying out solid-phase polymerization of the diacetylene part of a diacetylene nylon chloride and subjecting the chloride to thermal polycondensation in a mold. CONSTITUTION:The diacetylene part of a diacetylene nylon chloride of formula I [R1 and R2 are (substituted) (cyclo)alkylene or arylene] is subjected to solid- phase polymerization. The objective molded article can be produced by the thermal polycondensation of the polymerized chloride in a mold under a pressure of 0.5X10 -15X10 atm. at 100-400 deg.C. The chloride of formula I is preferably produced usually by mixing diacetylenecarboxylic acid of formula II with equimolar amount of diamine of formula III. The solid-phase polymerization of the diacetylene part is carried out, e.g., by sealing the chloride of formula I in vacuum and irradiating with gamma-ray of cobalt 60.
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公开(公告)号:JPS63178851A
公开(公告)日:1988-07-22
申请号:JP31825787
申请日:1987-12-16
Applicant: AGENCY IND SCIENCE TECHN
Inventor: NAKAO YUKIMICHI , KAERIYAMA KYOJI , KATO MASAO
Abstract: PURPOSE:To efficiently produce the title catalyst having high activity with good reproducibility by bringing a noble metal hydrosol into contact with an anion-exchange resin having a quaternary ammonium group to deposit the noble metal colloidal particles on the resin surface. CONSTITUTION:The noble metal hydrosol is brought into contact with the anion-exchange resin having a quaternary ammonium group to deposit the noble metal colloidal particles on the resin surface, and the deposition type noble metal catalyst is produced. As a result, the solid catalyst carrying fine noble metal colloidal particles can be easily and efficiently produced. The obtained solid catalyst has a large catalytic surface area and can be widely used in the catalytic reactions ranging from the liq. phase reaction to the gas phase reaction, the recovery is also easy, and the reproducibility of the catalytic activity is excellent.
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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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