Antistatic Agent Contains Pentavalent Nitrogen Patents (Class 260/DIG20)
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Patent number: 6117922Abstract: 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: GrantFiled: March 16, 1998Date of Patent: September 12, 2000Assignee: Clariant GmbHInventor: Michael Breitwieser
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Patent number: 5153075Abstract: 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: GrantFiled: July 25, 1990Date of Patent: October 6, 1992Assignee: W. R. Grace & Co.-Conn.Inventors: Marvin R. Havens, William P. Roberts
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Patent number: 4999252Abstract: 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: GrantFiled: September 26, 1988Date of Patent: March 12, 1991Assignee: W. R. Grace & Co.-Conn.Inventors: Marvin R. Havens, William P. Roberts
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Patent number: 4448916Abstract: 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: GrantFiled: December 16, 1980Date of Patent: May 15, 1984Assignee: American Organics Corp.Inventor: Irvin W. Martenson
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Patent number: 4341884Abstract: 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: GrantFiled: April 1, 1981Date of Patent: July 27, 1982Assignee: Stamicarbon, B.V.Inventor: Herman A. J. Schepers
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Patent number: 4341885Abstract: 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: GrantFiled: April 1, 1981Date of Patent: July 27, 1982Assignee: Stamicarbon, B.V.Inventor: Herman A. J. Schepers
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Patent number: 4323634Abstract: 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: GrantFiled: November 10, 1977Date of Patent: April 6, 1982Assignee: Eastman Kodak CompanyInventor: Thomas A. Jadwin
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Patent number: 4313978Abstract: 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: GrantFiled: December 3, 1979Date of Patent: February 2, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventors: John Stevens, John S. Huizinga, Stephen Newman
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Patent number: 4299903Abstract: 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: GrantFiled: July 3, 1980Date of Patent: November 10, 1981Assignee: Xerox CorporationInventors: Christopher J. AuClair, Chin H. Lu
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Patent number: 4298710Abstract: 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: GrantFiled: August 30, 1979Date of Patent: November 3, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Masaki Ohya, Akio Kobayashi, Takeo Ogiwara, Yoshikatsu Satake
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Patent number: 4286037Abstract: 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: GrantFiled: September 5, 1978Date of Patent: August 25, 1981Assignee: Oce-van der Grinten N.V.Inventors: Adrianus M. P. Hectors, Gerardus J. Crommentuyn
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Patent number: 4276138Abstract: 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: GrantFiled: June 22, 1979Date of Patent: June 30, 1981Assignees: Agency of Industrial Science & Technology, Shin-Etsu Chemical Co., Ltd.Inventors: Michihiko Asai, Yoshio Suda, Kiyoshi Imada, Susumu Ueno, Hirokazu Nomura
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Patent number: 4221856Abstract: 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: GrantFiled: April 3, 1978Date of Patent: September 9, 1980Assignee: Xerox CorporationInventor: Chin H. Lu
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Patent number: 4165303Abstract: 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: GrantFiled: August 26, 1977Date of Patent: August 21, 1979Assignee: Emery Industries, Inc.Inventors: Irwin S. Schlossman, Robert E. Wiman
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Patent number: 4149999Abstract: 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: GrantFiled: October 11, 1977Date of Patent: April 17, 1979Assignee: Lockheed Aircraft CorporationInventor: John V. Butler
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Patent number: 4145327Abstract: 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: GrantFiled: January 5, 1978Date of Patent: March 20, 1979Assignee: The Firestone Tire & Rubber CompanyInventors: Ronald G. Dolch, Robert N. Kerr, Jr.
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Patent number: 4128484Abstract: 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: GrantFiled: July 14, 1975Date of Patent: December 5, 1978Assignee: The Procter & Gamble CompanyInventors: Brian D. Barford, Lawrence Benjamin
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Patent number: 4121026Abstract: 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: GrantFiled: March 23, 1973Date of Patent: October 17, 1978Assignee: Petrolite CorporationInventors: William J. Cheng, David B. Guthrie
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Patent number: 4104175Abstract: 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: GrantFiled: November 19, 1975Date of Patent: August 1, 1978Assignee: Modokemi AktiebolagInventors: Eva Margareta Martinsson, Karl Martin Edvin Hellsten
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Patent number: 4070531Abstract: 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: GrantFiled: January 30, 1976Date of Patent: January 24, 1978Assignees: Deutsche Gold- und Silber-Scheideanstalt Vormals Roessler, Henkel & Cie. GmbHInventors: Werner Schwarze, Wolfgang Merk, Volker Binder
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Patent number: 4045361Abstract: 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: GrantFiled: May 21, 1975Date of Patent: August 30, 1977Assignee: The Procter & Gamble CompanyInventors: David M. Watt, Jr., Joseph P. Nirschl
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Patent number: 3988158Abstract: Antistatic and antifoaming agents for use with light sensitive silver halide photographic materials comprised of polymerized pyridyl-type compounds are disclosed.Type: GrantFiled: October 6, 1975Date of Patent: October 26, 1976Assignee: Konishiroku Photo Industry Co., Inc.Inventors: Toshio Muramatsu, Koichi Nagayasu, Masayuki Kimura, Sadatugu Terada, Masayoshi Mayama
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Patent number: 3933779Abstract: 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: GrantFiled: February 21, 1974Date of Patent: January 20, 1976Assignee: Fine Organics Inc.Inventors: Seymour Baron, H. Harald Lutzmann
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Patent number: 3933697Abstract: 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: GrantFiled: July 30, 1974Date of Patent: January 20, 1976Assignee: Toyo Rubber Chemical Industrial CorporationInventors: Osamu Fujii, Toshio Kishimoto, Hisao Kosuge, Ryoji Nagamine, Sumio Shimada