Benzidines Patents (Class 564/309)
  • Patent number: 5648539
    Abstract: A process for the preparation of arylamines which comprises the reaction of methyldiphenylamine and diiodobiphenyl in the presence of a ligated copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: February 29, 1996
    Date of Patent: July 15, 1997
    Assignee: Xerox Corporation
    Inventor: H. Bruce Goodbrand
  • Patent number: 5639914
    Abstract: The present invention provides novel amine compounds useful as electron-transporting materials to be incorporated in organic electro-luminescence devices. More particularly, the present invention provides an organic electro-luminescence device (organic EL device) which can find wide application in various display units, requires a low applied voltage and exhibits a high luminance and an excellent stability.
    Type: Grant
    Filed: November 1, 1994
    Date of Patent: June 17, 1997
    Assignees: Hodogaya Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Hiromitsu Tomiyama, Masahiko Oshino, Ikuko Ihara, Naoko Nakanishi
  • Patent number: 5610183
    Abstract: Compounds of Formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein Q is optionally substituted phenyl or naphthyl;X and Y are each H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or X and Y are together .dbd.O;Z is O or S;R.sup.1 is H, optionally substituted C.sub.1-6 alkyl, optionally substituted phenyl (C.sub.1-4 alkyl), C.sub.2-6 alkenyl, COC.sub.1-6 alkylhalo, COR.sup.a, COOR.sup.a, CONHR.sup.a, COC.sub.1-6 alkylNR.sup.a R.sup.b or CONR.sup.a C.sub.1-6 alkylCONR.sup.a R.sup.b ;R.sup.2 is substituted C.sub.1-6 alkyl, optionally substituted phenyl(C.sub.1-4 alkyl), C.sub.2-6 alkenyl, C.sub.1-6 alkylhalo, COR.sup.a, COOR.sup.a, CONHR.sup.a, COC.sub.1-6 alkylNR.sup.a R.sup.b or CONR.sup.a C.sub.1-6 alkylCONR.sup.a R.sup.b ;or R.sup.1 and R.sup.2 together form a chain (CH.sub.2).sub.p optionally substituted by oxo;R.sup.3 is H [or C.sub.1-6 alkyl];R.sup.4 is H, C.sub.1-6 alkyl or phenyl; andR.sup.5 is optionally substituted (CH.sub.2).sub.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: March 11, 1997
    Assignee: Merck, Sharp & Dohme Ltd.
    Inventors: Andrew P. Owens, Brian J. Williams
  • Patent number: 5550290
    Abstract: The present invention relates to a benzidine derivative represented by the general formula (1): ##STR1## wherein R.sup.1 to R.sup.6, m and n are as defined in the present specification. The benzidine derivative improves durability and heat resistance of a membrane containing the same while maintaining high hole transferring capability. Therefore, an electrophotosensitive material, which comprises a photosensitive layer containing the benzidine derivative, has high sensitivity and is superior in durability and heat resistance.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: August 27, 1996
    Assignee: Mita Industrial Co. Ltd.
    Inventors: Yasufumi Mizuta, Masashi Tanaka, Nariaki Muto, Toshiyuki Fukami, Hideo Nakamori, Mikio Kakui, Sakae Saito, Hiroshi Shiomi, Keisuke Sumida, Maki Uchida
  • Patent number: 5489711
    Abstract: An oligomer from diarylamines is disclosed which has desirable antioxidant properties in lubricating oils which contain synthetic ester lubricants. The oligomer is desirable for use at higher temperatures where it has less volatility than simple diarylamines. The oligomer has substantial portions of monosubstituted diphenylamine repeat units which result in linear oligomers. Di and polysubstituted diphenylamines may optionally be present as repeat units. These di and polysubstituted diphenylamines generally react as monofunctional reactants in oligomerization and tend to reduce the number of repeat units in the average oligomer.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: February 6, 1996
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5482822
    Abstract: An infrared-absorptive compound is disclosed which has the structure represented by the following formula (I) or (II) ##STR1## Also, an optical recording medium having a recording layer containing the infrared-absorptive compound is disclosed.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: January 9, 1996
    Assignee: Canon Kabushiki Kaisha
    Inventors: Chieko Mihara, Hiroyuki Sugata, Tsuyoshi Santo, Miki Tamura
  • Patent number: 5476968
    Abstract: A N,N'-bis(p-hydroxymethylphenyl)benzidine compound having the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group or a methoxy group; R.sub.2 represents an alkyl group having one to four carbon atoms, a methoxy group or an ethoxy group; and R.sub.3 represents a hydrogen atom or a methyl group, is intended to be used as a charge transporting material of an electrophotographic photoreceptor. A method for preparing the compound includes formylating a N,N'-diphenylbenzidine derivative having the following formula (II): ##STR2## by the conventional Viismeier reaction to obtain a N,N'-bis(p-formylphenyl) benzidine derivative of the following formula (III): ##STR3## and reducing the derivative with a boron hydride salt or an aluminum hydride salt.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: December 19, 1995
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Akira Imai, Katsumi Nukada
  • Patent number: 5457108
    Abstract: The invention relates to substituted 5-oxo-di-benzo[a,d]cyclohepta-1,4-dienes of the formula (I) ##STR1## processes for their preparation and their use as retroviral agents.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: October 10, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hanno Wild, Jutta Hansen, Jorg Lautz, Arnold Paessens
  • Patent number: 5453478
    Abstract: This invention relates to o-tolidines which have a tert-butyl substituent ortho to an amine group. These compositions are represented by the formula: ##STR1## where R.sub.1 =i-propyl, or t-butyl, and where R.sub.2 =hydrogen, i-propyl, or t-butyl.The compositions are useful in the preparation of polyepoxide resins as well as polyurethanes, polyamides and polyimides.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: September 26, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Kevin R. Lassila, Michael E. Ford, Kenneth M. Kem, Susan M. Clift
  • Patent number: 5403958
    Abstract: Disclosed is an electrophotographic member containing as a charge transport material a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative which is remarkably excellent in solubility in an organic solvent and/or a binder such as polycarbonate resin, etc., can show very excellent electrophotographic properties such as high sensitivity, low residual potential and high durability. Further, a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative usable as a charge transport material, and a process for producing the same are disclosed. Furthermore, a fluorine-containing diarylamine usable for producing the fluorine-containing N,N,N',N'-tetraarylbenzidine derivative, and a process for producing the same are disclosed.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: April 4, 1995
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yoshii Morishita, Yasushi Sugimoto, Shigeru Hayashida, Hiroko Ishikawa, Yoshiaki Noda, Shigeru Murakami, Munehiro Sato, Yoshinori Saito, Naoji Kurata, Yoshio Sugita
  • Patent number: 5362822
    Abstract: An adduct is prepared by reacting (A) a compound containing at least one epoxy group per molecule, with (B) a compound containing at least one epoxide reactive group per molecule selected from the group consisting of phenolic, thiol, secondary amine and carboxyl; wherein (i) when compound (A) is a polyepoxide, compound (B) contains a single epoxide reactive group per molecule; (ii) when compound (A) is a monoepoxide it is a monoglycidyl ether and compound (B) contains at least two epoxide reactive groups per molecule; and (iii) at least one of components (A) and (B) contains a rodlike mesogenic moiety. These adducts are useful in the preparation of polyurethanes.
    Type: Grant
    Filed: January 3, 1994
    Date of Patent: November 8, 1994
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5352834
    Abstract: Disclosed is an electrophotographic member containing as a charge transport material a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative which is remarkably excellent in solubility in an organic solvent and/or a binder such as polycarbonate resin, etc., can show very excellent electrophotographic properties such as high sensitivity, low residual potential and high durability. Further, a fluorine-containing N,N,N',N'-tetraarylbenzidine derivative usable as a charge transport material, and a process for producing the same are disclosed. Furthermore, a fluorine-containing diarylamine usable for producing the fluorine-containing N,N,N',N'-tetraarylbenzidine derivative, and a process for producing the same are disclosed.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: October 4, 1994
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Yoshii Morishita, Yasushi Sugimoto, Shigeru Hayashida, Hiroko Ishikawa, Yoshiaki Noda, Shigeru Murakami, Munehiro Sato, Yoshinori Saito, Naoji Kurata, Yoshio Sugita
  • Patent number: 5349104
    Abstract: Without added stabilizers, aminobenzotrifluorides have low thermal and storage stability.The present invention relates to preparations of a stabilized amionbenzotrifluoride, composed essentially ofa) an aminobenzotrifluoride of the formula (I), ##STR1## in which R.sup.1 and R.sup.2, independently of each other, are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, substituted or unsubstituted aryl, halogen, CF.sub.3, nitro, amino, methoxy, hydroxyl or NR.sup.3 R.sup.4, where R.sup.3 and R.sup.4, independently of each other, are hydrogen or C.sub.1 -C.sub.5 -alkyl radicals, and the NH.sub.2 group can be located in the 2-, 3- or 4-position in relation to the CF.sub.3 group, andb) at least one base.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: September 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gilbert Billeb, Gunther Semler
  • Patent number: 5298661
    Abstract: Charge transporting materials having general formula (I): ##STR1## R.sup.1 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; an aralkyl group; a nitro group; an unsubstituted or substituted aryl group; a halogen; an amino group; an unsubstituted or substituted dialkylamino group; R.sup.2 represents hydrogen; an unsubstituted or substituted alkyl group; an alkoxyl group having 1 to 4 carbon atoms; or a halogen; R.sup.3 represents hydrogen; an alkyl group having 1 to 4 carbon atoms; an alkoxyl group having 1 to 4 carbon atoms; a halogen; a dialkylamino group; an amino group; a thioalkoxyl group having 1 to 4 carbon atoms; an aryloxy group; a methylenedioxy group; an aralkyl group; or an unsubstituted or substituted aryl group; R.sup.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 29, 1994
    Assignee: Ricoh Company, Ltd.
    Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
  • Patent number: 5245030
    Abstract: An IR-ray absorptive compound represented by the formula (1) or (2): ##STR1## and an optical recording medium having a substrate and an organic dye thin film, comprising the formulae (1) and/or (2).
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: September 14, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tetsuro Fukui, Yoshihiro Oguchi, Hiroyuki Sugata, Kyo Miura
  • Patent number: 5235105
    Abstract: The present invention relates to a process for the preparation of pure 3,3',4,4'-tetraaminobiphenyl in high yield by ammonolysis of 3,3,-dichlorobenzidine in the presence of copper powder and CuCl. After the crude product has been washed with ammonia water and water, the 3,3',4,4'-tetraaminobiphenyl, thus pretreated, is crystallized in water in the presence of 0 to 5% by weight of activated carbon and of about 1 to 2% by weight of a water-soluble reducing agent at temperatures of about 100.degree. to about 140.degree. C., under a protective gas atmosphere (redissolution). The water-soluble reducing agent is an alkali metal dithionite or alkali metal sulfite. The protective gas used can be nitrogen. The water used in the recrystallization (redissolution water) can be reused in whole or in part in the recrystallization.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: August 10, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Edgar Vorwerk
  • Patent number: 5225595
    Abstract: Sulfonyl compounds of the formula ##STR1## where Ar is the radical of a benzene or naphthalene ring,R.sup.1 and R.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,R.sup.3 is nitro, amino, C.sub.1 -C.sub.4 -alkanoylamino or benzoylamino, andR.sup.4 is a radical of the formula ##STR2## where X.sup.1, X.sup.2 and X.sup.3 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl, andX.sup.4 is a group which is detachable under alkaline conditions,either in the free form or in the form of their salts, are useful for synthesizing reactive dyes.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Claus Marschner, Manfred Patsch
  • Patent number: 5208376
    Abstract: A process for the continuous preparation of 3,3'-dichlorobenzidine dihydrochloride from 2,2'-dichlorohydrazobenzene by treatment with aqueous sulfuric acid, which comprises treating the 2,2'-dichlorohydrazobenzene, dissolved in a water-immiscible aromatic solvent, continuously at temperatures of from about 20.degree. to about 50.degree. C. in the presence of an alkali metal salt of an alkyl (C.sub.8 -C.sub.23)polyglycol ether sulfate, with such an amount of from about 50 to about 80 % strength aqueous sulfuric acid that the suspension formed remains conveyable, subsequently diluting the suspension emerging from the reaction zone with water, again continuously, and subsequently heating the suspension to a temperature of from about 90.degree. to about 95.degree. C.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: May 4, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Kurt Habig, Konrad Baessler, Klaus Warning
  • Patent number: 5196583
    Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: March 23, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki
  • Patent number: 5175367
    Abstract: This invention concerns novel fluorine-containing diamines, polyamides and polyimides. The compounds are useful in the formation of moisture resistant films, fibers and shaped articles.
    Type: Grant
    Filed: August 27, 1991
    Date of Patent: December 29, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 5116708
    Abstract: A hole transporting material is constituted by a compound represented by the following general formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, are each independently hydrogen or a hydrocarbon residue having 1 to 20 carbon atoms; Ar.sup.1 and Ar.sup.2 are each independently a divalent hydrocarbon residue; l is an integer of 0 or more; m is an integer of 1 or more; and n is an integer of 2 or more.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 26, 1992
    Assignee: Nippon Oil Company, Limited
    Inventors: Yutaka Shikatani, Naoki Kataoka, Nobuyuki Kuroda, Kazuo Matsuura
  • Patent number: 5068435
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using gamma alumina as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.The catalyst is also effective for producing unsymmetrical disubstituted alkyl aromatic amines, e.g., ethyl or propyl toluidine where one ortho position is substituted with a methyl group and the other substituted with an ethyl or propyl group.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: November 26, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William F. Burgoyne, Jr., Dale D. Dixon
  • Patent number: 5047590
    Abstract: Compounds having formula (I), which are useful as starting or intermediate materials for preparing organic photoconductive materials, or as organic photoconductive materials: ##STR1## wherein R.sup.1 is a nitro group, an amino group or a diphenylamino group which may have a substituent; and R.sup.2 is hydrogen or an alkyl group having 1 to 6 carbon atoms, and methods of preparing the above compounds are disclosed.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: September 10, 1991
    Assignee: Ricoh Company, Ltd.
    Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga
  • Patent number: 5041666
    Abstract: A method is provided for the production of 3,3', 4,4'-tetraaminobiphenyl (TAB) from biphenyl comprising the following steps:1) acetylating the biphenyl in the presence of an appropriate Friedel-Crafts catalyst to obtain 4,4'-diacetylbiphenyl (DAcB);2) oximating the DAcB to form DAcB dioxime;3) subjecting the dioxime to a double Beckmann rearrangement to obtain N,N-diacetylbenzidine (DiAcBz);4) nitrating the DiAcBz to obtain 3,3'-dinitro-N,N-diacetylbenzidine (DNAcBz)5) removing the acetyl groups of the DNAcBz by basic hydrolysis to form 3,3'-dinitrobenzidine (DNB); and6) reducing the nitrate groups of the DNB to form TAB.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: August 20, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Bennett C. Ward, Wilson B. Ray, Charles B. Hilton, Anthony J. East, Kenneth G. Davenport
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4992350
    Abstract: An electrophotographic photoconductor is disclosed, which comprises an electroconductive support and a photoconductive layer formed thereon comprising as an effective component at least one biphenyl compound represented by the following formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryl group which may have a substituent, provided that at least one of R.sup.1 and R.sup.2 represents an unsubstituted or substituted aryl group. Furthermore, charge transporting materials comprising the above biphenyl compound and novel biphenyl compounds having formula (II) for use in the electrophotographic photoconductor are disclosed.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: February 12, 1991
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
  • Patent number: 4987258
    Abstract: The invention relates to 4,4'-diaminodiphenyl compounds of the formula I ##STR1## in which X denotes the n-propyl, isopropyl, n-butyl, isobutyl, 1-methylpropyl, n-propoxy, isopropoxy, isobutoxy, 1-methylpropoxy or 2-methoxyethoxy radical and A is 0 or the equivalent of an inorganic acid.The preparation is effected by reducing ortho-X-substituted nitrobenzene and benzidine rearrangement of the resulting hydrazobenzene derivative. The compounds of the formula (I) are suitable for use as components in the preparation of dyes and pigments.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: January 22, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Hunger, Heinrich Frolich, Kurt C. Habig
  • Patent number: 4935544
    Abstract: This invention illustrates a new compound, octanitrobenzidine. It is utild as a new high energy explosive compound. Octanitrobenzidine is formed by dissolving a tetrqanitrobenzidine with sulfuric acid in the presence of a metal sulfate catalyst. This reaction mixture is further reacted with nitric and sulfuric acid at a temperature sufficient to complete the reaction, then rapidly cooled, and octanitrobenzidine is recovered.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: June 19, 1990
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Arnold T. Nielsen, Ronald L. Atkins, William P. Norris
  • Patent number: 4933245
    Abstract: An electrophotographic photoreceptor is disclosed, which comprises an electrically conductive support having provided thereon a photoconductive layer containing, as a charge transport material, a compound represented by formula (I) ##STR1## wherein R.sub.1 represents an alkyl group, and R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, an alkoxycarbonyl group, or a substituted amino group. The photoreceptor satisfies both electrical and mechanical requirements without undergoing adverse influences from binder resins used therein.
    Type: Grant
    Filed: September 18, 1987
    Date of Patent: June 12, 1990
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Yutaka Akasaki, Katsuhiro Sato, Naoya Yabuuchi, Kiroyuki Tanaka, Katsumi Nukada
  • Patent number: 4920022
    Abstract: An electrophotographic photosensitive member comprises a conductive support and provided thereon a photosensitive layer, wherein said photosensitive layer contains an amine compound represented by the Formula (I) or Formula (II).
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: April 24, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Teigo Sakakibara, Kiyoshi Sakai, Harumi Sakoh, Shoji Amamiya
  • Patent number: 4876377
    Abstract: This invention pertains to an improved process for the alkylation of aromatic amines. The improvement resides in the use with particular aromatic amines and olefins a catalyst which is a highly acidic partially dealuminated zeolite having an increased silica to alumina molar ratio over the original zeolite and an acidity factor of at least 0.3. The partially dealuminated zeolites are preferably exchanged with hydrogen or rare earth metal and are particularly effective for producing an alkylated aromatic amine where the alkyl group is ortho to the amine. The highly acidic partially dealuminated H-mordenite and partially dealuminated HY faujasite are very effective for the alkylation of aniline with propylene.
    Type: Grant
    Filed: March 22, 1988
    Date of Patent: October 24, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Rakesh Agrawal, Steven R. Auvil, Michel Deeba
  • Patent number: 4764625
    Abstract: The process of preparing a tertiary amine by the condensation of a mono- or di-tertiary amine and a mono- or di-iodoaryl compound. Conducting the condensation reaction in the presence of potassium hydroxide, and a copper catalyst, either in the absence of a solvent or with an inert saturated hydrocarbon solvent, in an inert atmosphere, at a temperature between from about 120.degree. C. to about 190.degree. C. for a period of time sufficient to at least substantially complete the reaction.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: August 16, 1988
    Assignee: Xerox Corporation
    Inventors: S. Richard Turner, John F. Yanus, Dale S. Renfer
  • Patent number: 4740620
    Abstract: This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using an acidic crystalline molecular sieve as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: April 26, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dale D. Dixon, William F. Burgoyne, Jr.
  • Patent number: 4588666
    Abstract: Disclosed is a hole transporting molecule comprised of alkoxy derivatives of tetra phenyl biphenyl diamine of the following formula: ##STR1## wherein R.sub.1 is independently selected from the group consisting of hydrogen, ortho alkoxy, meta alkoxy, para alkoxy, ortho alkyl, meta alkyl, para alkyl, 3,5-dialkoxy, 2,4-dialkoxy, and 2,5-dialkoxy; and R.sub.2 is selected from the group consisting of ortho alkoxy, meta alkoxy, para alkoxy, 3,5-dialkoxy, 2,4-dialkoxy, and 2,5-dialkoxy; and layered imaging member containing therein the aforementioned alkoxydiamine derivatives and a photoconductive layer.
    Type: Grant
    Filed: June 24, 1985
    Date of Patent: May 13, 1986
    Assignee: Xerox Corporation
    Inventors: Milan Stolka, Kathleen M. McGrane, John S. Facci
  • Patent number: 4532350
    Abstract: Process for the selective preparation of metachloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase and in an acid medium, under the action of heat and under pressure, in the presence of a noble metal used in association with a heavy metal.These meta-chloroanilines are intermediates especially for active plant-protection substances.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: July 30, 1985
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Georges Cordier, Pierre Fouilloux
  • Patent number: 4433168
    Abstract: Crude 3,4,3',4'-tetraaminodiphenyl (TAD) prepared by ammonolysis of 3,3'-dichlorobenzidine in the presence of mainly Cu catalysts is purified by a process in which(a) after its isolation from the preparation process crude TAD is treated with an aqueous NH.sub.3 solution and, if desired, TAD thus treated is then(b) dissolved and reprecipitated in water in the presence of adsorbents and also of a water-soluble reducing agent.Compared with relevant processes of the state of the art, the process produces a higher yield of pure TAD and it is also simpler to carry out.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: February 21, 1984
    Assignee: Hoechst AG
    Inventors: Hans Schubert, Konrad Baessler
  • Patent number: 4418213
    Abstract: Process for the selective preparation of meta-chloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase, under the action of heat, at atmospheric pressure or under pressure, in the presence of a noble metal, in an anhydrous organic medium and in the presence of a Lewis acid.These meta-chloroanilines are intermediates especially for active plant-protection substances.
    Type: Grant
    Filed: July 14, 1981
    Date of Patent: November 29, 1983
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Georges Cordier, Pierre Fouilloux
  • Patent number: 4351959
    Abstract: A process for the dechlorination of aromatic nitro or amino compounds consists in reacting anilines or nitrobenzenes which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of iodide or bromide ions, in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: September 28, 1982
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Cordier
  • Patent number: 4340759
    Abstract: A process for the dechlorination of aromatic nitro or amino compounds consists in reacting anilines or nitrobenzenes which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of cations (Bi, Pb, Sn, Tl, Hg and Ag), in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.
    Type: Grant
    Filed: January 24, 1980
    Date of Patent: July 20, 1982
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Cordier
  • Patent number: 4326078
    Abstract: In a process for the hydrogenation of nitrobenzene with hydrogen to hydrazobenzene at temperatures ranging from 40.degree. to 110.degree. C. in the presence of a precious metal catalyst, an aqueous alkaline solution and an organic solvent, the reaction mixture being maintained in turbulent motion, the improvement wherein said nitrobenzene is o-, m- or p-chloronitrobenzene, the reaction is carried out in an organic solvent in which the dichlorohydrazobenzene being formed is readily soluble when warm and difficultly soluble when cold, and that the precious metal catalyst is used in such amount that the weight ratio of chloronitrobenzene used to precious metal catalyst is in the range 1:0.00005-less than 0.0002.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: April 20, 1982
    Assignee: Dynamit Noble Aktiengesellschaft
    Inventor: Hans-Joachim Herrmann
  • Patent number: 4324914
    Abstract: A process for the dechlorination of aromatic nitro or amino compounds comprising reacting anilines or nitrobenzenes, which are polysubstituted by chlorine, with hydrogen, under the action of heat, in the presence of an excess of chloride ions, in the liquid phase and at low pressure.The process makes it possible selectively to obtain anilines which are chlorine-substituted in the meta-position.
    Type: Grant
    Filed: January 23, 1980
    Date of Patent: April 13, 1982
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Cordier
  • Patent number: 4322530
    Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4317932
    Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4299897
    Abstract: A photosensitive member having at least two electrically operative layers is disclosed. The first layer comprises a photoconductive layer which is capable of photogenerating holes and injecting photogenerated holes into a contiguous charge transport layer. The charge transport layer comprises an electrically inactive organic resinous material containing from about 10 to about 75 percent by weight of: ##STR1## R.sub.1 is selected from the group consisting of hydrogen (ortho) CH.sub.3, (meta) CH.sub.3, (para) CH.sub.3, and R.sub.2 is selected from the group consisting of hydrogen, (ortho) CH.sub.3, (meta) CH.sub.3, and (para) CH.sub.3. The charge transport layer while substantially non-absorbing in the spectral region of intended use is "active" in that it allows injection of photogenerated holes from the photoconductive layer, and allows these holes to be transported through the charge transport layer.
    Type: Grant
    Filed: February 15, 1980
    Date of Patent: November 10, 1981
    Assignee: Xerox Corporation
    Inventors: Milan Stolka, John F. Yanus, Damodar M. Pai, Dale S. Renfer, James M. Pearson
  • Patent number: H728
    Abstract: There are provided substituted p-benzidines of the formula ##STR1## wherein Ar is phenyl or phenoxyphenyl.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: February 6, 1990
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: J. Shield Wallace, Fred E. Arnold