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公开(公告)号:JPH05140083A
公开(公告)日:1993-06-08
申请号:JP30058591
申请日:1991-11-15
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , YAMAGUCHI KEISABURO , YAMAGUCHI TERUHIRO
IPC: B01J31/02 , B01J31/18 , C07B61/00 , C07C315/04 , C07C317/22
Abstract: PURPOSE:To obtain the subject compound useful as a flame-retardant or its raw material at a low cost by brominating bis(4-hydroxyphenyl)sulfone with bromine and reacting with an alkyl halide in the presence of a phase-transfer catalyst, etc., without separating and purifying the bromination product. CONSTITUTION:Bis(4-hydroxyphenyl)sulfone (BPS) is brominated with bromine (preferably 4-4.25mol based on 1mol of BPS) in a state suspended in a mixture of water and a water-immiscible organic solvent (preferably chlorobenzene, etc.) to obtain bis(4-hydroxy-3,5-dibromophenyl)sulfone. The objective bis(4- allyloxy-3,5-dibromophenyl)sulfone is produced by successively reacting the brominated compound with an allyl halide in the presence of a base (preferably sodium hydroxide) and a phase-transfer catalyst such as the compound of formula (R1 to R4 are benzyl or 1-4C alkyl; Y is N or P; X is Cl, Br, etc.) without separating or purifying the brominated compound.
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公开(公告)号:JPH0585990A
公开(公告)日:1993-04-06
申请号:JP24744891
申请日:1991-09-26
Applicant: MITSUI TOATSU CHEMICALS
Inventor: OE TADAYUKI , MATSUO MITSUKI , YAMAGUCHI TERUHIRO
IPC: B01J23/04 , B01J27/232 , C07B61/00 , C07C201/12 , C07C205/38
Abstract: PURPOSE:To obtain the subject new compound, having low dielectric properties, excellent in molding processability and useful as a raw material for aromatic diamines for polyimides. CONSTITUTION:3,3'-Dinitro-5,5'-bis(trifluoromethyl)diphenyl ether expressed by formula I. The above-mentioned compound is obtained by reacting 3- hydroxy-5-nitrilofluoromethylbenzene expressed formula II (used in a molar amount of preferably 1-1.2 times based on 3,5-dinitrotrifluoromethylbenzene expressed by formula III) with the compound expressed by formula III in the presence of a base such as potassium carbonate (used in an equiv. amount of preferably 1-2 times based on the raw material compound expressed by formula II) in an aprotic polar solvent such as formamide (used in an amount of 1-10 times based on the raw material compound expressed by formula II) at preferably 100-150 deg.C for 1-30hr.
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公开(公告)号:JPH04202181A
公开(公告)日:1992-07-22
申请号:JP33001890
申请日:1990-11-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , OE TADAYUKI , YAMAGUCHI TERUHIRO
IPC: C07D209/48 , B29C33/60 , C08K5/3412 , C08K5/3417
Abstract: NEW MATERIAL:The compound of formula I [R1 is 8-30C aliphatic hydrocarbon group; R2 is 1-15C bivalent hydrocarbon group having a molecular weight of 14-1,000 and optionally containing O or tert. N atom; X and Y are O or N-R3 (R3 is H or 1-15C univalent hydrocarbon group having a molecular weight of 15-1000 and optionally containing O or tert. N atom)]. USE:A mold release agent for thermosetting resin such as unsaturated polyester resin, epoxy resin, urethane resin, urethane/urea resin, urea resin or phenolic resin. PREPARATION:The objective compound can be produced by reacting trimellitic acid with an aliphatic primary amine of formula R1-NH2 (e.g. dodecylamine) in an organic polar solvent (e.g. N,N-dimethylacetamide or DMF) preferably at 20-25 deg.C for 0.5-15hr, and reacting the resultant imidocarboxylic acid of formula II with an active hydrogen compound of formula HX-R2-YH (e.g. ethylenediamine) preferably at 130-250 deg.C for 1-5hr.
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公开(公告)号:JPH04202156A
公开(公告)日:1992-07-22
申请号:JP33001990
申请日:1990-11-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , OE TADAYUKI , YAMAGUCHI TERUHIRO
IPC: B01J27/125 , B01J27/128 , B01J27/135 , C07B61/00 , C07C45/46 , C07C49/84 , C07C319/20 , C07C323/22 , C08K5/07 , C08K5/37
Abstract: NEW MATERIAL:A bis(alkylcarbonylphenyl) compound shown by formula I (R1 is 7-30C aliphatic hydrocarbon (X is O, S) which may contain 5X0 or 5XS and has mol.wt. of 14-500). USE:A modifier and a stabilizer for various reins and a mold release material for thermosetting resin. PREPARATION:A diphenyl compound shown by formula II is made to react with a carboxylic acid halide shown by formula III (Y is halogen) or a carboxylic acid anhydride shown by formula IV in the presence of a Friedel Crafts catalyst to give a bis(alkylcarbonyl) compound shown by formula I.
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公开(公告)号:JPH05320100A
公开(公告)日:1993-12-03
申请号:JP12705792
申请日:1992-05-20
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , YAMAGUCHI KEISABURO , YAMAGUCHI TERUHIRO
IPC: C07C201/12 , C07C205/38 , C07C213/00 , C07C213/02 , C07C217/90
Abstract: PURPOSE:To obtain an aromatic dinitro compound for liquid crystal polyimide raw material, etc., having good processability and solubility by condensing bis(4-hydroxycumyl)benzene with 2-chloro-5-nitrobenzotrifluoride in the presence of a base in a porous solvent. CONSTITUTION:Bis(4-hydroxycumyl)benzene expressed by formula I is made to react with 2-chloro-5-nitrobenzotrifluoride in N,N-dimethylformamide in N,N-dimethylformamide in the presence of potassium carbonate, etc., at 110 deg.C for 4hr and then cooled to 80 deg.C and filtered to remove an inorganic salt and the filtrate is cooled till room temperature by adding water thereto and the resultant deposited crystal is filtered to afford 1,3-bis[4-(4-nitro-2- trifluoromethylphenoxy)cumyl]benzene of formula II. Then this aromatic dinitro compound is reduced in a solvent such as Methyl Cellosolve in the presence of a catalyst consisting of Pb/C under hydrogen atmosphere to provide 1,3- bis[4-(4-amino-2-trifluoromethylphenoxy)cumyl]benzene of formula III.
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公开(公告)号:JPH05310649A
公开(公告)日:1993-11-22
申请号:JP12333792
申请日:1992-05-15
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , YAMAGUCHI KEISABURO , YAMAGUCHI TERUHIRO
IPC: C07C201/12 , C07C205/38 , C07C213/02 , C07C217/78 , C07C217/90 , C07C255/54
Abstract: PURPOSE:To obtain a new dinitro compound useful as a raw material for aromatic diamino compounds which are raw materials for polyimide resins. CONSTITUTION:The dinitro compound is expressed by formula T (R1 and R2 are H, halogen, 1-5C alkyl, alkoxy or cyano or at least one of R1 and R2 is a substituent group other than H), e.g. 1,3-bis[4-(4-nitro-1-methylphenoxy) cumyl]benzene. This compound expressed by formula I is obtained by condensing a bis(4-hydroxycumyl)benzene derivative expressed by formula II with a p- halogenonitro compound expressed by formula III (X is halogen) in the presence of a base (e.g. potassium carbonate) in an aprotic polar solvent (e.g. DMF) at 20-200 deg.C. This compound expressed by formula I can be reduced to provide aromatic diamino compounds, which are useful as a raw material for liquid crystalline polyimides excellent in molding processability and solubility in solvents.
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公开(公告)号:JPH05140081A
公开(公告)日:1993-06-08
申请号:JP29540591
申请日:1991-11-12
Applicant: MITSUI TOATSU CHEMICALS
Inventor: MATSUO MITSUKI , YAMAGUCHI KEISABURO , YAMAGUCHI TERUHIRO
IPC: B01J31/02 , C07B61/00 , C07C315/04 , C07C317/22
Abstract: PURPOSE:To obtain the subject compound useful as a raw material for flame- retardant, etc., in high purity at a low cost by reacting bis(4-hydroxy-3,5- dibromophenyl)sulfone with an allyl halide in the presence of a specific phase- transfer catalyst. CONSTITUTION:The objective bis(4-allyloxy-3,5-dibromophenyl)sulfone can be produced by etherifying bis(4-hydroxy-3,5-dibromophenyl) sulfone with an allyl halide in a mixture of water and an organic solvent such as benzene in the presence of an alkali (preferably sodium hydroxide) and a phase-transfer catalyst consisting of a polyethylene glycol of formula ((n) is 5-70; R1 and R2 are H or 1-4C alkyl) or its alkyl ether preferably at 60-120 deg.C for 1-15hr under stirring.
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公开(公告)号:JPH04202180A
公开(公告)日:1992-07-22
申请号:JP32997490
申请日:1990-11-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor: OE TADAYUKI , MATSUO MITSUKI , YAMAGUCHI TERUHIRO
IPC: C07D209/48 , C08K5/3412 , C08K5/3417
Abstract: NEW MATERIAL:The compound of formula I (R and R are 8-24C aliphatic hydrocarbon group). EXAMPLE:4-Stearoxycarbonyl-N-stearylphthalimide. USE:An internal mold release agent for thermosetting resin such as unsaturated polyester resin, epoxy resin, urethane/urea resin, urea resin and phenolic resin. PREPARATION:The objective compound can be produced by reacting trimellitic anhydride with an aliphatic primary amine of formula R-NH2 (e.g. dodecylamine) in an organic solvent (e.g. N,N-dimethylacetamide or DMF), and reacting the resultant imidocarboxylic acid of formula II with an aliphatic alcohol of formula R -OH (e.g. 1-dodecanol) preferably at 150-250 deg.C.
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公开(公告)号:JPH04202179A
公开(公告)日:1992-07-22
申请号:JP32997390
申请日:1990-11-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor: OE TADAYUKI , MATSUO MITSUKI , YAMAGUCHI TERUHIRO
IPC: C07D209/48 , C08K5/3412 , C08K5/3417
Abstract: NEW MATERIAL:The compound of formula I (R is 8-24C aliphatic hydrocarbon group; R and R are aliphatic hydrocarbon group having total carbon number of 8-48; one of R and R may be H). EXAMPLE:4-(N-stearylcarbamoyl)-N-stearylphthalimide. USE:An internal mold release agent for thermosetting resin such as unsaturated polyester resin, epoxy resin, urethane/urea resin, urea resin and phenolic resin. PREPARATION:The objective compound can be produced by reacting trimellitic anhydride with an aliphatic primary amine of formula R-NH2 (e.g. dodecylamine) in an organic solvent (e.g. N,N-dimethylacetamide or DMF), and reacting the resultant imidocarboxylic acid of formula II with an aliphatic amine of formula R R NH (e.g. dodecylamine) preferably at 150-250 deg.C.
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公开(公告)号:JPH0469376A
公开(公告)日:1992-03-04
申请号:JP18105590
申请日:1990-07-09
Applicant: MITSUI TOATSU CHEMICALS
Inventor: OE TADAYUKI , MATSUO MITSUKI , UCHIDA YUJI , YAMAGUCHI TERUHIRO
IPC: B41M5/337 , B41M5/26 , C07D205/10 , C07D209/48 , C07D403/06 , C07D403/08 , C07D403/10 , C08K5/3412 , C08K5/3415
Abstract: NEW MATERIAL:A compound expressed by formula I (R is 8-24C aliphatic hydrocarbon group; A is aliphatic, alicyclic or aromatic tetravalent group). USE:Useful as a release agent in resin molding or sensitizer for data recording paper, especially heat sensitive paper and various kinds of additives. The compound exhibits high thermal stability and readily soluble property to an organic solvent. PREPARATION:A tetracarboxylic acid dianhydride expressed by formula II is made to react with an aliphatic primary amine expressed by the formula R-NH2 in a solvent such as N,N-dimethylacetoamide at
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