Antistatic Agent Contains Pentavalent Nitrogen Patents (Class 260/DIG20)
  • Patent number: 6117922
    Abstract: The present invention relates to an antistatic mixture comprising compounds of the formulae (I) and (II)R'--N--[(C.sub.n H.sub.2n)--OH].sub.2 (I) ##STR1## where n is 2 or 3R.sup.1 is C.sub.8 -C.sub.22 -alkyl or -alkenyl or C.sub.8 -C.sub.22 -alkyl-CO-- andR.sup.2, R.sup.3 and R.sup.4 may be identical or different and are C.sub.8 -C.sub.22 -alkyl or -alkenyl and two of these radicals may be hydrogen,and where the mixing ratio of the compounds of formulae I and II is from 4:1 to 1:10 parts by weight,and to a process for preparing this mixture.This mixture is solid and is therefore easy to use in production, and is storage-stable and offers advantages in handling.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: September 12, 2000
    Assignee: Clariant GmbH
    Inventor: Michael Breitwieser
  • Patent number: 5153075
    Abstract: An acid copolymer/quaternary amine mixture is disclosed which is permanently antistatic. The acid copolymer is a copolymer of (i) a major amount by mol % of an alpha-olefin of the formula RCH.dbd.CH.sub.2 wherein R is H or C.sub.1 to C.sub.8 alkyl, and (ii) a minor amount by mol % of an alpha,beta-ethylenically unsaturated carboxylic acid. The quaternary amine is of the formula [(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4)N]+ [X]- wherein R.sup.1 is selected from H, aryl, or C.sub.1 to C.sub.50 alkyl optionally having one or more non-contiguous C.dbd.O or NHC.dbd.O or --S-- or --O-- in the carbon chain, or the same as R.sup.2 ; each of R.sup.2, R.sup.3, and R.sup.4 is the same or different and selected from H, C.sub.1 to C.sub.18 alkyl optionally substituted with one or more OH or from --(R.sup.5 --O).sub.a --H where a is an integer from 1 to 10 and R.sup.5 is ethylene or propylene; and X is an anion selected from chloride, bromide, iodide, fluoride, nitrate, fluoborate, phosphate, C.sub.1 to C.sub.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: October 6, 1992
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Marvin R. Havens, William P. Roberts
  • Patent number: 4999252
    Abstract: An acid copolymer/quaternary amine mixture is disclosed which is permanently antistatic. The acid copolymer is a copolymer of (i) a major amount by mol % of an alpha-olefin of the formula RCH.dbd.CH.sub.2 wherein R is H or C.sub.1 to C.sub.8 alkyl, and (ii) a minor amount by mol % of an alpha,beta-ethylenically unsaturated carboxylic acid. The quaternary amine is of the formula [(R.sup.1)(R.sup.2)(R.sup.3)(R.sup.4)N].sup.+ [X].sup.- wherein R.sup.1 is selected from H, aryl, or C.sub.1 to C.sub.50 alkyl optionally having one or more non-contiguous C.dbd.O or NHC.dbd.O or --S-- or --O-- in the carbon chain, or the same as R.sup.2 ; each of R.sup.2, R.sup.3, and R.sup.4 is the same or different and selected from H, C.sub.1 to C.sub.18 alkyl optionally substituted with one or more OH or from --(R.sup.5 --O).sub.a --H where a is an integer from 1 to 10 and R.sup.5 is ethylene or propylene; and X is an anion selected from chloride, bromide, iodide, fluoride, nitrate, fluoborate, phosphate, C.sub.1 to C.sub.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: March 12, 1991
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Marvin R. Havens, William P. Roberts
  • Patent number: 4448916
    Abstract: There is disclosed a liquid gel composition useful for incorporation in thermoplastic and thermosetting resins. The liquid gel comprises a liquid mixture of certain hydroxyalkyl fatty amines or fatty imidazolium quaternaries which is gelled by an organophilic, expanding lattice clay that is ion exchanged with alkyl ammonium ions. The clay is employed at a sufficient concentration to form a stable gel and is milled into the liquid vehicle to form a gel of a suitable viscosity to permit it to be added to the resin with metering injection equipment. The composition when used at low concentrations in resins enhances the physical properties of the resins by imparting a permanent anti-static characteristic to the resins and by significantly decreasing their brittleness, thereby increasing elongation, impact and tensile strengths of the resins.
    Type: Grant
    Filed: December 16, 1980
    Date of Patent: May 15, 1984
    Assignee: American Organics Corp.
    Inventor: Irvin W. Martenson
  • Patent number: 4341885
    Abstract: An improved polymer composition having a combination of good flow behavior, UV stability, and very good impact resistance is described, essentially composed ofa.50-95 parts by weight of one or more copolymers obtained by the polymerization of a mixture of10-90% by weight of styrene and/or derivatives of styrene, with90-10% by weight of acrylonitrile and/or methacrylonitrile; andb.5-50 parts by weight of1. a largely saturated rubber, and2. chlorinated polyethylene, wherein the chlorinated polyethylene has a chlorine content of at least 10% by weight, a DSC crystallinity of at least 10% and a glass transition temperature of at least equal to -15.degree. C.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: July 27, 1982
    Assignee: Stamicarbon, B.V.
    Inventor: Herman A. J. Schepers
  • Patent number: 4341884
    Abstract: An improved polymer composition having a combination of good flow behavior, UV stability, and very good impact resistance is described, essentially composed ofa. 50-95 parts by weight of one or more copolymers obtained by the polymerization of a mixture of10-90% by weight of acrylonitrile and/or methacrylonitrile; and,b. 5-50 parts by weight of1. a largely saturated rubber, and2. chlorinated polyethylene, wherein the chlorinated polyethylene has a chlorine content of 32-40% by weight, a DSC crystallinity of 0-7%, while the weight ratio of rubber to chlorinated polyethylene is between 2:1 and 1:10, i.e., from 0.1 to 2.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: July 27, 1982
    Assignee: Stamicarbon, B.V.
    Inventor: Herman A. J. Schepers
  • Patent number: 4323634
    Abstract: The present invention relates to the use of low levels of quaternary ammonium salt surfactants as charge control agents for an electrostatic toner contained in dry electrographic developer compositions. Particularly useful such charge control agents are those which contain at least one amido group having 10 or more carbon atoms attached to the ammonium cation and an anion selected from a halide ion or an organosulfur-containing anion.
    Type: Grant
    Filed: November 10, 1977
    Date of Patent: April 6, 1982
    Assignee: Eastman Kodak Company
    Inventor: Thomas A. Jadwin
  • Patent number: 4313978
    Abstract: A method of treating a surface, e.g. carpet, gramophone record, to reduce the static charging thereon which comprises applying a novel antistatic composition comprising a fluorinated anionic surfactant which is an amine salt of an acid containing a fluorinated organic radical and an antistatic agent which is an ionic salt of an amine, preferably in alcoholic solution.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: February 2, 1982
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John Stevens, John S. Huizinga, Stephen Newman
  • Patent number: 4299903
    Abstract: This invention relates to a process for the preparation of dry positively charged toner particles, and more spceifically a polymerization process for preparing dry positively charged toner resins, containing a charge control agent, or additive which has a dual function, as a wetting agent in the polymerization process, and as a charge control agent for the toner resin, whereby the charge control agent is firmly bonded (attached) to the toner resin and is uniformly dispersed in the resin, or emulsion polymerization of a monomer material, a pigment and a charge control additive. As a result of the polymerization there is formed a dry positively charged toner resin which has attached thereto the charge control agent.
    Type: Grant
    Filed: July 3, 1980
    Date of Patent: November 10, 1981
    Assignee: Xerox Corporation
    Inventors: Christopher J. AuClair, Chin H. Lu
  • Patent number: 4298710
    Abstract: An antistatic resin composition comprises 100 parts of a nitrile copolymer comprising 7 to 100% of a nitrile graft copolymer with a graft ratio of 4 to 50% obtained by graft-polymerizing a monomer mixture of a specific composition onto a rubber trunk polymer predominantly comprising a conjugated diolefin and/or an acrylate, and 0 to 93% of a nitrile random copolymer of a specific composition; and 0.05 to 10 parts of a surfactant added thereto. This antistatic resin composition, wherein the rubber trunk polymer forms a bridge structure, not only has, per se, an excellent antistatic property but also an antistatic property which undergoes substantially no change upon washing, for example, with water.
    Type: Grant
    Filed: August 30, 1979
    Date of Patent: November 3, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masaki Ohya, Akio Kobayashi, Takeo Ogiwara, Yoshikatsu Satake
  • Patent number: 4286037
    Abstract: Electrically conductive developer powder for developing electrostatic images by inductive attraction is provided, with avoidance of practical disadvantages of known "one-component" developer powders, by incorporating finely divided water-insoluble quaternary ammonium salt into thermoplastic resin particles forming the powder, with or without other finely divided additives such as coloring material and/or magnetically attractable material. The specific resistance of the resin particles is lowered to between 10.sup.7 and 10.sup.11 ohm. cm by from 8 to 35% by weight of the quaternary ammonium salt, and can be lowered further by additions of fine conductive material such as carbon black. The resin particles remain sufficiently fusible even when they also contain enough magnetically attractable material, e.g. about 50% by weight, to render them transportable by a magnetic powder-applicator.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: August 25, 1981
    Assignee: Oce-van der Grinten N.V.
    Inventors: Adrianus M. P. Hectors, Gerardus J. Crommentuyn
  • Patent number: 4276138
    Abstract: A method for reducing static electricity on the surface of a shaped article made of polyvinyl chloride resins, which method comprises the steps of (a) blending a surface active agent with the polyvinyl chloride resin prior to fabrication of the resin into a shaped article, (b) fabricating the resin admixed with the surface active agent into a shaped article, and (c) subjecting the shaped article to a treatment with low temperature plasma of a gas.
    Type: Grant
    Filed: June 22, 1979
    Date of Patent: June 30, 1981
    Assignees: Agency of Industrial Science & Technology, Shin-Etsu Chemical Co., Ltd.
    Inventors: Michihiko Asai, Yoshio Suda, Kiyoshi Imada, Susumu Ueno, Hirokazu Nomura
  • Patent number: 4221856
    Abstract: Toners comprised of a resin and a quaternary ammonium compound of the formula ##STR1## in which at least two R radicals are hydrocarbon radicals having from about 8 to about 22 carbon atoms and each other R is a hydrogen or hydrocarbon radical having from 1 to about 8 carbon atoms, and A is an anion for example, sulfate, sulfonate, nitrate, borate, chlorate, and the halogens such as iodide, chloride, and bromide. Methods of their formation and use in various electrophotographic imaging systems is disclosed. The quaternary ammonium compound is generally present as a coating on a pigment that is used in the toner, such pigment being for example carbon black. Toners containing the above described quaternary ammonium compounds generally result in a toner containing a positive charge thus allowing development of negative images that may be formed on photoreceptors, especially organic photoreceptors.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: September 9, 1980
    Assignee: Xerox Corporation
    Inventor: Chin H. Lu
  • Patent number: 4165303
    Abstract: Polyamides and polyesters having greatly improved resistance to static electricity buildup are obtained by the incorporation of about 0.1 to 20 weight percent poly(alkylene ether) esters of polybasic acid. The antistatic properties of these polymers is significantly improved when poly(ethylene oxide) esters of dimer and trimer acids are employed.
    Type: Grant
    Filed: August 26, 1977
    Date of Patent: August 21, 1979
    Assignee: Emery Industries, Inc.
    Inventors: Irwin S. Schlossman, Robert E. Wiman
  • Patent number: 4149999
    Abstract: An antistatic liquid, and method of use thereof, comprising an ionizable electroconductive polymer, an alcohol and a suitable solvent, for suppressing electrostatic charges which might otherwise develop in certain procedures relating to the manipulation and transport of microspheres, microbeads, or other microscopic particles, as well as the suppression of the reformation of polymers which might otherwise interfere with such procedures.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: April 17, 1979
    Assignee: Lockheed Aircraft Corporation
    Inventor: John V. Butler
  • Patent number: 4145327
    Abstract: Disclosed is a novel antistatic pressure-sensitive adhesive composition essentially comprising an aqueous latex copolymer of a vinyl ester and an alkyl acrylate to which an adhesive-compatible ammonium salt has been added. An antistatic pressure-sensitive adhesive is prepared by dispersing, as an antistatic promoter, a compatible ammonium salt, such as a quaternary ammonium salt, directly with the latex copolymer. By coating one side of a suitable release paper with the antistatic pressure-sensitive adhesive thus prepared and thereafter laminating the adhesive side of the coated release paper to a film material, the tendency for such materials to accumulate electrostatic charges upon the removal of the release paper is greatly reduced.
    Type: Grant
    Filed: January 5, 1978
    Date of Patent: March 20, 1979
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Ronald G. Dolch, Robert N. Kerr, Jr.
  • Patent number: 4128484
    Abstract: An aqueous emulsion comprising a fatty alkyl ester of a polyhydric alcohol and a cationic surfactant provides a fabric softening composition of unexpected efficacy. In particular, the use of a sorbitan ester with a cationic surfactant provides a softening agent which deposits effectively onto fabric from an aqueous bath.
    Type: Grant
    Filed: July 14, 1975
    Date of Patent: December 5, 1978
    Assignee: The Procter & Gamble Company
    Inventors: Brian D. Barford, Lawrence Benjamin
  • Patent number: 4121026
    Abstract: This invention relates to copolymers of alpha-olefins and maleic anhydride reacted with amines in the presence of Lewis acids, preferably BF.sub.3 or a complex thereof; and to the use of these products as anti-static agents in organic liquids, preferably in hydrocarbons. The use of Lewis acid produces a unique reaction product which is superior as to fluidity and/or anti-static properties as compared to the corresponding product produced without Lewis acid. In addition, the use of Lewis acid promotes the rate of reaction thus reducing reaction time.
    Type: Grant
    Filed: March 23, 1973
    Date of Patent: October 17, 1978
    Assignee: Petrolite Corporation
    Inventors: William J. Cheng, David B. Guthrie
  • Patent number: 4104175
    Abstract: Quaternary ammonium compounds are provided which are useful in the treatment of substrates such as plastic materials and textile materials, both woven and nonwoven, from natural and synthetic fibers and mixtures thereof, to impart antistatic properties.A process is also provided for the preparation of such compounds, and for the treatment of substrates with such compounds.
    Type: Grant
    Filed: November 19, 1975
    Date of Patent: August 1, 1978
    Assignee: Modokemi Aktiebolag
    Inventors: Eva Margareta Martinsson, Karl Martin Edvin Hellsten
  • Patent number: 4070531
    Abstract: There are used as antistatic agents for thermoplastic synthetic resins compounds of the formulae ##STR1## where R and R' are saturated alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms and wherein one of R and R' can be hydrogen,R.sup.2 is hydrogen, lower alkyl with one to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl o-,m- and/or p-methylbenzyl, o-,m- and/or p-chlorobenzyl, o-,m- and/or p-bromobenzyl, aminoalkyl (C.sub.2 to C.sub.6), preferably aminoalkyl (C.sub.2 and C.sub.3), alkyl (C.sub.1 to C.sub.6)-aminoalkyl (C.sub.2 to C.sub.6), 2-hydroxyethyl-aminoalkyl (C.sub.1 to C.sub.6), 2-hydroxypropyl-aminoalkyl (C.sub.2 to C.sub.6) or 2,3-dihydroxypropyl-aminoalkyl (C.sub.2 to C.sub.6),R.sup.3 in case the compound is present as the ammonium salt is hydrogen or a lower alkyl group with 1 to 5 carbon atoms,R.sup.4 is hydrogen or hydroxyl, andX.sup.
    Type: Grant
    Filed: January 30, 1976
    Date of Patent: January 24, 1978
    Assignees: Deutsche Gold- und Silber-Scheideanstalt Vormals Roessler, Henkel & Cie. GmbH
    Inventors: Werner Schwarze, Wolfgang Merk, Volker Binder
  • Patent number: 4045361
    Abstract: Aqueous liquid rinse-added fabric conditioning compositions comprising diamine static control agents, quaternary ammonium fabric softeners and, optionally, particulate sorbitan ester material provide fabric softening and exceptional fabric static control.
    Type: Grant
    Filed: May 21, 1975
    Date of Patent: August 30, 1977
    Assignee: The Procter & Gamble Company
    Inventors: David M. Watt, Jr., Joseph P. Nirschl
  • Patent number: 3988158
    Abstract: Antistatic and antifoaming agents for use with light sensitive silver halide photographic materials comprised of polymerized pyridyl-type compounds are disclosed.
    Type: Grant
    Filed: October 6, 1975
    Date of Patent: October 26, 1976
    Assignee: Konishiroku Photo Industry Co., Inc.
    Inventors: Toshio Muramatsu, Koichi Nagayasu, Masayuki Kimura, Sadatugu Terada, Masayoshi Mayama
  • Patent number: 3933779
    Abstract: An antistatic polymer blend comprising a synthetic polymer and an antistatically effective amount of a compound of the formula: ##EQU1## wherein R is alkyl of 4 to 18 carbon atoms unsubstituted or substituted by halo or aryl.
    Type: Grant
    Filed: February 21, 1974
    Date of Patent: January 20, 1976
    Assignee: Fine Organics Inc.
    Inventors: Seymour Baron, H. Harald Lutzmann
  • Patent number: 3933697
    Abstract: An antistatic polyurethane foam contains quaternary ammonium salt as an antistatic agent. The quaternary ammonium salt is added either to a raw material for polyurethane foam or to a prepared polyurethane foam by causing the foam to be impregnated with a solution containing the quaternary ammonium salt and drying it.
    Type: Grant
    Filed: July 30, 1974
    Date of Patent: January 20, 1976
    Assignee: Toyo Rubber Chemical Industrial Corporation
    Inventors: Osamu Fujii, Toshio Kishimoto, Hisao Kosuge, Ryoji Nagamine, Sumio Shimada