公开(公告)号：JPH11322678A

公开(公告)日：1999-11-24

申请号：JP14229198

申请日：1998-05-08

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

Inventor： FUKUDA TAKASHI ,  MATSUDA HIROO ,  KIMURA TATSUMI ,  MORIYA NORIHIKO ,  KATO MASAO ,  OKADA SHUJI ,  NAKANISHI HACHIRO

IPC: G02F1/35 ,  C07C67/08 ,  C07C69/92 ,  G02F1/355 ,  G02F1/361

Abstract: PROBLEM TO BE SOLVED: To obtain a new aromatic ester oligomer giving organic secondary nonlinear optical materials having good optical transparency and secondary nonlinear optical characteristics and not causing the deterioration of the characteristics with the passage of time. SOLUTION: A compound of formula I [R and R are each H or methyl; (n) and (n') are each 4-10; (m) is 2-5], for example, 4-[4'-(6-acryloyloxyhexyloxy) phenylcarbonyloxy]benzoic acid 6-acryloyloxyhexyl ester. The compound of formula I is preferably obtained by a method comprising converting an aromatic carboxylic acid of formula II [for example, 4-(6-acryloyloxyhexyloxy)benzoic acid] into the corresponding acid halide by the use of thionyl chloride, etc., and subsequently reacting the acid halide with a compound of formula III (for example, 4-hydroxybenzoic acid 6-acryloyloxyhexyl ester) in the presence of a hydrogen halide-capturing agent such as triethylamine in an organic solvent such as tetrahydrofuran.

公开(公告)号：JPH0291106A

公开(公告)日：1990-03-30

申请号：JP24315088

申请日：1988-09-28

Applicant: AGENCY IND SCIENCE TECHN

Inventor： MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO

IPC: C08F138/00

Abstract: PURPOSE:To produce the title crystal which has a high strength isotropically and a network structure having covalent bonds multi-dimensionally by subjecting crystals obtained from diacetylenedicarboxylic acid, a polyvalent metal carbonate and/or a polyvalent metal acetate to solid-state polymerization. CONSTITUTION:0.1-100mmol/l of a solution of a diacetylenedicarboxylic acid of the given formula (wherein n is 0-20) is added to a solution of a polyvalent metal carbonate and/or a polyvalent metal acetate (e.g., copper acetate) in a molar ratio of the acid to the metal salt of 1:(1-2) to form a homogeneous solution or suspension, which is stirred to react them at room temperature to 100 deg.C or below, thereby producing diacetylenedicarboxylic acid metal salt crystals. The crystals are irradiated with ultraviolet light for several to 100 hours, or with tens of MRad to hundreds of MRad or gamma ray (e.g., cobalt 60) in a vacuum, or are heated at tens of degrees to 200 deg.C for tens of hours to hundreds of hours, or are subjected to several thousands to ten thousands of atmospheres for tens of minutes, thereby effecting the solid-state polymerization.

公开(公告)号：JPS6348265A

公开(公告)日：1988-02-29

申请号：JP19240486

申请日：1986-08-18

Applicant: AGENCY IND SCIENCE TECHN

Inventor： OKADA SHUJI ,  MATSUDA HIROO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  MURAMATSU RYOJI

IPC: C07D213/30 ,  C07D213/38 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE:To obtain the titled material useful as material for a light wavelength converting element, etc., stable at room temperature, readily providing large single crystal, comprising p-toluenesulfonic acid 1-methyl-4-[2-(4-hydroxyphenyl) vinyl[pyridinium. CONSTITUTION:An organic material for non-linear optical use comprising p- toluenesulfonic acid 1-methyl-4-[2-(4-hydroxyphenyl)vinyl] pyridinium shown by formula I and one comprising p-toluenesulfonyl acid 1-methyl-4-[2-(4-(N,N- dimethylamino)phenyl)] vinyl pyridinium shown by formula II. The compounds shown by formula I and formula II are synthesized by condensing 1,4- dimethylbipyridinium obtained from gamma-picoline and methyl iodide with 4- hydroxybenzaldehyde and 4-(N,N-dimethylamino)benzaldehyde through dehydration and reacting the reaction products with p-toluenesulfonic acid. Large single crystal is obtained by slow evaporation method, etc.

公开(公告)号：JPS6256939A

公开(公告)日：1987-03-12

申请号：JP19718185

申请日：1985-09-05

Applicant: AGENCY IND SCIENCE TECHN ,  TODA KOGYO CORP

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

IPC: C07F7/10 ,  C07C67/00 ,  C07C201/00 ,  C07C205/06 ,  G02F1/35 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE:To obtain the titled material capable of enlarging a SHG and having a stability at room temp. and enabling to easily growing a large monocrystal by selecting the 8 kinds of the compds. defined by the specific table from a specific ethynyl nitrobenzene derivative shown by the formula. CONSTITUTION:The titled material is composed of the ethynyl nitrobenzene derivative shown by the formula and comprises the 8 kinds of the compds. defined by the table. The prescribed derivative is prepared by reacting the corresponding halonitroiodobenzene derivative with the ethynyl derivative in a solvent and in the presence of a bispalladium II chloride catalyst. Thus, the titled material having the larger SHG than that of an urea by a few times and a stable at the room temp. and making an ease to grow a large monocrystal is obtd.

公开(公告)号：JP2001051276A

公开(公告)日：2001-02-23

申请号：JP2000208722

申请日：2000-07-10

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

Inventor： FUKUDA TAKASHI ,  MATSUDA HIROO ,  NISHIKADO TADAMORI ,  KATO MASAO

IPC: G02F1/1337 ,  C08F2/48 ,  C08F20/34 ,  G02F1/1333

Abstract: PROBLEM TO BE SOLVED: To form a polymerized film, which controls interaction between a substrate and a liquid crystal, on a cell substrate by incorporating a divinyl compound into the liquid crystal and photopolymerizing the divinyl compound on a cell substrate by being irradiated with light from a transparent substrate side. SOLUTION: A polymerized film is formed on a liquid crystal cell substrate in which a liquid crystal is encapsulated between two substrates at least one of which is a transparent substrate. For this purpose, a divinyl compound is incorporated into the liquid crystal and photopolymerized on the substrate by being irradiated with light from the side of the transparent substrate. The used divinyl compound has two vinyl groups in its molecule and is a low molecular weight compound having a molecular weight of 1,000 or lower, preferably 400 or lower. The lower limit of the molecular weight is normally about 250. The divinyl compound expressed by the formula is preferably used. In the formula, A denotes a linear molecule backbone part and R3-R8 each denotes hydrogen or a substituent. The linear molecule backbone part A includes a linear bivalent aliphatic group and the like.

公开(公告)号：JPH11322685A

公开(公告)日：1999-11-24

申请号：JP14214298

申请日：1998-05-08

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

Inventor： MATSUDA HIROO ,  FUKUDA TAKASHI ,  KIMURA TATSUMI ,  KATO MASAO ,  OKADA SHUJI ,  NAKANISHI HACHIRO

IPC: G02F1/35 ,  C07C227/18 ,  C07C229/60 ,  C07C253/30 ,  C07C255/55 ,  C07C323/62 ,  G02F1/355 ,  G02F1/361

Abstract: PROBLEM TO BE SOLVED: To obtain a novel compound that has a good level of optical transparency and the secondary nonlinear optical property and is useful as an organic secondary nonlinear optical material. SOLUTION: This novel compound is represented by formula I (X is a dialkylamino, an alkylthio; Y is nitro or cyano; n is 1-3), typically the compound of formula II. The compound of formula I is prepared by reaction of an aromatic carboxylic halide of formula III (Hal is a halogen), for example, 4- dimethylaminobenzoyl chloride, with a p-substituted phenol, for example, 4- cyanophenol or the like in the presence of a hydrogen halide acceptor in an inert solvent such as acetone and 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：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：JPH02281047A

公开(公告)日：1990-11-16

申请号：JP10023689

申请日：1989-04-21

Applicant: AGENCY IND SCIENCE TECHN ,  MITSUI TOATSU CHEMICALS

Inventor： OKADA SHUJI ,  MATSUDA YASUO ,  NAKANISHI HACHIRO ,  KATO MASAO ,  ABE KOJI ,  ITO HIROSHI

IPC: G02F1/35 ,  B05D1/20 ,  B29K9/00 ,  B29L31/34 ,  B32B9/00 ,  B32B27/08 ,  C08J5/18 ,  C09K11/06 ,  G02F1/355 ,  G02F1/361

Abstract: PURPOSE:To obtain the subject high-quality thin film useful as a material for electronic optical element to be used under a strong electric field of laser, etc., having excellent optical properties by mutually laminating an organic low molecular or polymer thin film and an organic polymer amorphous thin film. CONSTITUTION:For example, a compound provided with polarity by introducing a hydrophobic and a hydrophilic groups to an organic compound such as diacetylene derivative by using L.B method is dissolved in a solvent such as benzene in 10 to 5X10 mol/l, dripped into clear water or clear water containing cadmium chloride or potassium hydrogencarbonate and the organic low-molecular or polymer thin film extended on water surface is formed on a silicon plate, etc. Then an organic polymer amorphous thin film is formed from an organic polymer compound such as (meth) acrylic acid alkyl ester polymer on the polymer thin film by the same method and the organic low molecular or polymer thin film and the organic polymer amorphous thin film are mutually laminated to give the aimed complex thin film having preferably

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.