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11. 发明专利

JPH04189805A PRODUCTION OF NEW CONJUGATED POLYMER MATERIAL BY SOLID-PHASE POLYMERIZATION 失效
公开(公告)号：JPH04189805A
公开(公告)日：1992-07-08
申请号：JP32034290
申请日：1990-11-22
申请人： AGENCY IND SCIENCE TECHN
发明人： OKADA SHUJI , MATSUDA HIROO , MASAKI ATSUSHI , NAKANISHI HACHIRO , HIRAIZUMI KIKUKO
IPC分类号： C08F2/46 , C08F2/36 , C08F2/54 , C08F38/02
摘要： PURPOSE:To easily obtain the subject material useful for electronic material, etc., by a solid-phase polymerization comprising the irradiation of a crystal of a specific tetraacetylene molecule with light or radiation or by a two-stage solid-phase polymerization comprising the thermal polymerization of the above crystal at a temperature below its melting point and the post-polymerization of the obtained polymer. CONSTITUTION:The objective conjugated polymer material consisting of a di(polydiacetylene) of formula IV can be produced either by irradiating a crystal of the molecule of a tetraacetylene of formula I [R and R' are CH3(CH2)x (x is 0-19) or group of formula II (y is 0-19; z is 1-9)] (e.g. 15,17,19,21- hexatriacontatetrayne) with light (e.g. ultraviolet light or visible light) or radiation (e.g. X-ray or gamma-ray) or by heating the crystal at a temperature below the melting point of the crystal to obtain a polymer of formula III (n is polymerization degree) and irradiating the polymer with light (e.g. ultraviolet light or visible light) or radiation (e.g. X-ray or gamma-ray) or heating the polymer.

12. 发明专利

JPH0291106A MANUFACTURE OF MULTI-DIMENSIONAL POLYMER CRYSTAL 失效
公开(公告)号：JPH0291106A
公开(公告)日：1990-03-30
申请号：JP24315088
申请日：1988-09-28
申请人： AGENCY IND SCIENCE TECHN
发明人： MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO
IPC分类号： C08F138/00
摘要： 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.

13. 发明专利

JPS6348265A ORGANIC MATERIAL FOR NON-LINEAR OPTICAL USE 失效
公开(公告)号：JPS6348265A
公开(公告)日：1988-02-29
申请号：JP19240486
申请日：1986-08-18
申请人： AGENCY IND SCIENCE TECHN
发明人： OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , MURAMATSU RYOJI
IPC分类号： C07D213/30 , C07D213/38 , G02F1/35 , G02F1/355 , G02F1/361
摘要： 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.

14. 发明专利

JPH1180275A ACRYLAMIDE COPOLYMER, ITS PRODUCTION AND SECONDARY NONLINEAR OPTICAL MATERIAL 失效
公开(公告)号：JPH1180275A
公开(公告)日：1999-03-26
申请号：JP25590997
申请日：1997-09-04
申请人： AGENCY IND SCIENCE TECHN , MATSUDA HIROO , FUKUDA TAKASHI
发明人： MATSUDA HIROO , FUKUDA TAKASHI , YAMADA SHINJI , KATO MASAO , NAKANISHI HACHIRO
IPC分类号： G02F1/35 , C08F8/30 , C08F220/60 , C08F222/40 , G02F1/355 , G02F1/361
摘要： 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.

15. 发明专利

JPH09227552A TETRATHIAFULVALENYL GROUP-CONTAINING DIACETYLENE DERIVATIVE AND ITS PRODUCTION 失效
公开(公告)号：JPH09227552A
公开(公告)日：1997-09-02
申请号：JP4274896
申请日：1996-02-29
申请人： AGENCY IND SCIENCE TECHN
发明人： SHIMADA SATORU , MATSUDA HIROO , OKADA SHUJI , NAKANISHI HACHIRO
IPC分类号： G03C1/73 , C07D339/06 , C08F38/02 , G02B1/04
摘要： 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.

16. 发明专利

JPH07233141A DIACETYLENE DERIVATIVE AND PRODUCTION THEREOF 失效
公开(公告)号：JPH07233141A
公开(公告)日：1995-09-05
申请号：JP5133894
申请日：1994-02-23
申请人： AGENCY IND SCIENCE TECHN
发明人： SHIMADA SATORU , MATSUDA HIROO , MINAMI SHINJI , OKADA SHUJI , NAKANISHI HACHIRO
IPC分类号： C07C319/18 , C07C319/14 , C07C323/19
摘要： 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.

17. 发明专利

JPH0192727A NONLINEAR OPTICAL ORGANIC MATERIAL 失效
公开(公告)号：JPH0192727A
公开(公告)日：1989-04-12
申请号：JP12285188
申请日：1988-05-19
申请人： AGENCY IND SCIENCE TECHN
发明人： OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , SAMURA HIDEO
IPC分类号： C09K3/00 , C07C67/00 , C07C209/00 , C07C211/52 , G02F1/35 , G02F1/355 , G02F1/361
摘要： 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.

18. 发明专利

JPS6259934A NONLINEAR OPTICAL ORGANIC MATERIAL 失效
公开(公告)号：JPS6259934A
公开(公告)日：1987-03-16
申请号：JP19970585
申请日：1985-09-10
申请人： AGENCY IND SCIENCE TECHN
发明人： OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , SAMURA HIDEO
IPC分类号： G02F1/35 , C07C211/42 , G02F1/313 , G02F1/355 , G02F1/361
摘要： 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.

19. 发明专利

JPH11322690A NEW DIVINYL COMPOUND AND ITS PRODUCTION 失效
公开(公告)号：JPH11322690A
公开(公告)日：1999-11-24
申请号：JP14213298
申请日：1998-05-08
申请人： AGENCY IND SCIENCE TECHN , FUKUDA TAKASHI , MATSUDA HIROO
发明人： FUKUDA TAKASHI , MATSUDA HIROO , MIYAJI YOJI , KATO MASAO , NAKANISHI HACHIRO
IPC分类号： G02F1/35 , C07C245/08 , G02F1/355 , G02F1/361
摘要： 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.

20. 发明专利

JPH02297529A ORGANIC MATERIAL FOR NONLINEAR OPTICAL USE 失效
公开(公告)号：JPH02297529A
公开(公告)日：1990-12-10
申请号：JP11213390
申请日：1990-04-27
申请人： AGENCY IND SCIENCE TECHN
发明人： OKADA SHUJI , MATSUDA HIROO , NAKANISHI HACHIRO , KATO MASAO , MURAMATSU RYOJI
IPC分类号： G02F1/35 , C07D213/38 , G02F1/355 , G02F1/361
摘要： 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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