US3190763A - Process for the anti-static finishing of high molecular weight compounds - Google Patents

Process for the anti-static finishing of high molecular weight compounds Download PDF

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Publication number
US3190763A
US3190763A US158585A US15858561A US3190763A US 3190763 A US3190763 A US 3190763A US 158585 A US158585 A US 158585A US 15858561 A US15858561 A US 15858561A US 3190763 A US3190763 A US 3190763A
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United States
Prior art keywords
static
molecular weight
high molecular
compounds
plastic
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Expired - Lifetime
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US158585A
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English (en)
Inventor
Schleede Dietrich
Schulde Felix
Rochlitz Fritz
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Hoechst AG
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Hoechst AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
    • C08K5/40—Thiurams, i.e. compounds containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
    • C08K5/405—Thioureas; Derivatives thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/09—Addition of substances to the spinning solution or to the melt for making electroconductive or anti-static filaments
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/16—Antistatic agents containing a metal, silicon, boron or phosphorus
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/17—High polymeric, resinous, antistatic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/19—Non-high polymeric antistatic agents/n
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/21—Polymer chemically or physically modified to impart antistatic properties and methods of antistatic agent addition

Definitions

  • Shaped articles of any kind of high molecular weight materials for example synthetic plastics, have a tendency towards electrostatic charging particularly when the material used possesses very good electric properties. Owingto this electrostatic charging these shaped articles, when used in practice, already exhibit dust deposits at the surface after a short time which deposits, in the case of .a strong electrostatic charging, show the wellknown zigzag design or crows feet. Owing to this strong electrostatic charging, moreover, sparking may occur on account of the great potential difference.
  • this method also has the disadvantage that water content of the plastic articles is reversible, i.e. the anti-static effect is lost when storing the articles treated in this manner in a dry atmosphere.
  • Nitrogen-containing compounds such as amines, amides, and quaternary ammonium salts
  • the anti-static agents can be applied to the shaped articles made of plastics materials by treating them with a solution of said agents. They may, however, also be incorporated by admixing the respective agents to the plastics powder prior to its processing.
  • An anti-static treatment by incorporating the anti-static agents has the advantage that it is possible at any time to finish high molecular weight materials on demand with anti-static agents also after their polymerization;
  • the al-. ready known organic compounds that arecapable of being incorporated 'must in order to attain a suificient anti-static effect the al-. ready known organic compounds that arecapable of being incorporated 'must, however, be added in amounts which entail a modification of the characteristic properties of the plastics material such, for example, as a decrease of the temperature ranges suitable for the processing, a reduction of the hardness, the rigidity, the thermostability under load, a deterioration of the color, etc'.
  • the compounds concerned are agents by whose incorporation the high molecular weight material finished therewith loses its physiological harmlessness.
  • Another possibilty of rendering high molecular weight materials resistant to electrostatic charge consists in incorporating additives during the polymerization.
  • This method has the disadvantages that the high molecular weight material is rendered resistant to electrostatic charge already in the manufacturing process, while the fabricator can in many cases decide only shortly before the final shaping whether an anti-static finishing is required for the desired purpose, or whether the slight deterioration of the electrical properties connected therewith is unwelcome.
  • the hitherto known additives during the polymerization the characteristic properties of the materials, for example the absorption of water, the chemical resistance, toughness, and hardness are modified in many cases.
  • hydrocarbon radicals may also be substituted, for example by halogens, amino groups, substituted amino groups, oxy groups, alk-oxy groups, thio ether, mercaptane groups, sulfonamide groups, carboxy alkyl groups, for ex ample the carboxylauryl groups, carboxycetal groups, etc., aryl groups or alkylaryl groups.
  • the compounds described may be added to the plastics materials both as such and also as ammonium salts together with inorganic or, preferably, organic acids.
  • Ureas or thio ureas in which R and R represent aliphatic radicals or H, generally have the best anti-static effect, above all in the case when R represents a methyl group and at least one of the radicals R rep-resents a longer alkyl radical such, for example, as the stearylor dodecyl radical.
  • anti-static agents there may be used, for example, the following compounds without limiting the process to these compounds:
  • urea and thio-urea for the subsequent anti-static finishing of finished fibers and filaments by spraying a solution or an aqueous dispersion on to the fibers and filaments has already been described.
  • phosphoric acid-Nmethylstearylamide-diamide be used as an anti-static agent.
  • this compound is an extremely effective agent it cannot be used in all fields of application with the same good success.
  • phosphoric-acid N-methylstearylamide-diamide is water-soluble to a certain extent so that it is'less suited for the anti-static finishing of fabrics or shaped articles which, after :being processed, are often subjected to a Washing process.
  • the working conditions and the temperature range in which the synthetic plastics can be shaped by a thermoplastic process remain the same. Moreover, the products are Well compatible with all polymers.
  • the anti static effect that can be attained is independenet of the moisture of the surroundings and practically of an unlimited duration. Exudation was not observed.
  • the surface does not become hydroscopic but remains unchanged.
  • the electric properties of the polymers are, of course, influenced by the addition of antistatic agents for this constitutes their anti-static efiicacy.
  • the deterioration of the specific transmissionand surface resistivity as well as of the dielectric properties is so trifling, however, that in most cases it is of no consequence even for the application of the polymers in the field of electrical engineering.
  • the substituted ureas or thio-ureas can be added prior to or during the polymerization, and also later on to the pulverulent high molecular weight polymer as well as to the granular product.
  • the ureas can be admixed in the melt, in solution and by application to the pulverulent or granular high molecular weight polymer.
  • the admixture is most advantageously effected prior to or during the processing. It was found that the technique of incorporation is of little importance. It is important, however, that the anti-static agents are distributed in the synthetic plastic as evenly as possible.
  • the high molecular weight polymers provided with an anti-static finishing can be processed by all customary processing methods, for example on molding presses, injection molding machines or extruders. From these high molecular weight polymer-s, therefore, there can be made compressionand injection-molded articles, semifinished goods, sheets, inflated hollow articles, tubes, fibers, filaments, monofilaments, etc.
  • the resin admixed with the compounds mentioned above can be processed in the usual manner as resin varnish or casting resin or in combination with glass fibers and/or fillers.
  • the high molecular weight polymers finished in this manner are especially interesting for packaging purposes (packing-material, canisters, bottles, beakers), as accessories for vacuum cleaners, band-conveyors, showroom patterns, and masters, parts for casings (for example for radioand television sets, vacuum cleaners), electric installations such as lighting fixtures, cable insulations, plugs, switches or armatures, air conditioning and ventilating equipments, plastics table ware, kitchen machinery, filaments, fibers, fabrics, sheets, lacquers, that is to say in all those cases in which an anti-static finishing is required.
  • the anti-static effect of inorganic or organic compounds in high molecular weight materials can be determined most easily by means of cigarette ash.
  • injectionor compression-molding are vigorously rubbed with a.- woollenclothfor .about .15 secondsandheld. about 2 mm. above a layer of cigarette ash.
  • the extruded or molded plates have good anti-static properties, they do 6 homogenizing, the material was worked up into granules which were. processed.intominjection-molded plates.
  • Examples 2, 4, 5, and 6 not attract cigarette ash.
  • the anti- P Q hlgh liloleculal Welght p y static effect attainable is not restricted to the aforemen- Theiantl-stflilc agents P' amounts 'added'thereofi tioned compounds or to the combinations with plastics 3ndthe-te$ tre$1 11t$alellsted 111 Table I materials as described in Table 1; As anti-static agents The anti-Smile agents Incorporated 111 the follow there may be used with the same success also other comlng manner: pounds corresponding to the summation formula in the Example 1 description.
  • polycarbonate polyacrylonitrile, a polyacrylic acid ester, a polymethacrylic acid ester, a polyamide, a polyurethane, a polyvinyl ester, a polyacetal, a polymer of a fluoroolcfin, a cellulosic polymer, an unsaturated polyester, and an epoxy resin, said plastic having incorporated therein and distributed therethrough, (b) 0.l-7% by weight, based on the plastic, of a compound of the formula:
  • X is a radical selected from the group consisting of oxygen and sulfur
  • R is a radical selected from the group consisting of H
  • CH R is an alkyl polymer which has a tendency to get dirty by attracting dust owing to electrostatic charging, which process consists essentially of incorporating an anti-static agent into said plastic in the course of its processing and distributing it substantially uniformly therethrough, said antistatic agent being present in said plastic in an amount of 0.1-7% by weight, based on the weight of the plastic, and having a chemical structure of the formula:
  • R and R are r wherein X is a radical selected from the group consisting of oxygen and sulfur, R is a radical selected from the group consisting of -H and CH R is an alkyl group containing 1 20 carbon atoms, and R and R are each selected from the group consisting of H, phenyl, and alkyl, the alkyl groups containing 1-20 carbon atoms each, and R and R may be substituted by a radical selected from the group consisting of an amino group, a hydroxy group, and a carbonyl group.
  • said high molecular weight polymer isselected from the group consisting of polystyrene, a copolymer of styrene with butadiene, a copolymer of styrene with acrylonitrile, a copolymer of styrene with vinyl carbazole, polyvinyl chloride, a polyterephthalate, a polyolefin, a polycarbonate, polyacrylonitrile, a polyacrylic acid ester, a polymethacrylic acid ester, a polyamide, a polyurethane, a polyvinyl ester, a polyacetal, a polymer of a fluoroolefin, a cellulosic polymer, an unsaturated polyester, and an epoxy resin.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US158585A 1960-12-17 1961-12-11 Process for the anti-static finishing of high molecular weight compounds Expired - Lifetime US3190763A (en)

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US (1) US3190763A (d)
BE (1) BE611662A (d)
CH (1) CH409382A (d)
DE (1) DE1494008A1 (d)
GB (1) GB1014303A (d)
NL (1) NL272600A (d)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282728A (en) * 1961-05-09 1966-11-01 Aquitaine Petrole Process for suppressing electrostatic charges on sulphur
US3297652A (en) * 1963-12-02 1967-01-10 Tomiyama Shinichi Method of suppressing electrostatc charges in synthetic resins and fibers
US3297653A (en) * 1963-12-02 1967-01-10 Tomiyama Shinichi Method of suppressing electrostatic charges in synthetic resins and fibers
US3449142A (en) * 1966-07-20 1969-06-10 Eastman Kodak Co Powder coated with an anti-static agent
US3514498A (en) * 1966-11-01 1970-05-26 Toray Industries Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist
US3523932A (en) * 1965-12-30 1970-08-11 Chem Y Thermoplastic composition
US3547863A (en) * 1966-01-28 1970-12-15 Hercules Inc Antistatic agents for high-polymeric compounds
US3548036A (en) * 1962-11-02 1970-12-15 Basf Ag Polymonoolefins containing an amine antistatic additive dispersed therein
US3549589A (en) * 1968-10-25 1970-12-22 Gen Tire & Rubber Co Color stabilized interpolymers of ethylene and vinyl acetate
US3630740A (en) * 1969-10-24 1971-12-28 Eastman Kodak Co Antistatic layers for polymeric photographic supports
US3867338A (en) * 1972-06-09 1975-02-18 Celanese Corp Thermal stabilization of polymers
US3902484A (en) * 1972-02-07 1975-09-02 Kimberly Clark Co Disposable surgical drape
US3925321A (en) * 1973-03-07 1975-12-09 Bayer Ag Polyamide compositions which have been rendered antistatic by the addition of sulfocarboxylic acid amides
US3974308A (en) * 1974-04-05 1976-08-10 Kimberly-Clark Corporation Method for treating a disposable surgical drape
US4061834A (en) * 1976-06-03 1977-12-06 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Durable antistatic coating for polymethylmethacrylate
US4083893A (en) * 1975-01-22 1978-04-11 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene
US4097546A (en) * 1976-03-30 1978-06-27 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene copolymers
DE3043570A1 (de) * 1979-11-26 1981-05-27 Colgate-Palmolive Co., 10022 New York, N.Y. Dialkylharnstoffe, ihre verwendung als weichmachendeund antistatisch wirkende mittel fuer textilien sowie diese mittel enthaltende wschmittelzusammensetzungen
US4346203A (en) * 1979-08-04 1982-08-24 Bayer Aktiengesellschaft Emulsifier for the preparation of polymers
US4694039A (en) * 1986-03-26 1987-09-15 Dsm Rim Nylon V.O.F. Stabilized lactam polymerization solutions
US5677357A (en) * 1995-07-05 1997-10-14 Cellular Technology International, Inc. Antistatic additive for organic polymer compositions
US20130323996A1 (en) * 2011-02-14 2013-12-05 Jnc Fibers Corporation Polyolefin-based antistatic fiber, being a single component or a conjugate type fiber, and nonwoven fabric including the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2050582A (en) * 1933-04-15 1936-08-11 Ig Farbenindustrie Ag Process of mercerizing cellulose material
US2165265A (en) * 1935-05-12 1939-07-11 Ig Farbenindustrie Ag Process of imparting hydrophobic properties to cellulose fibers
US2657984A (en) * 1950-10-20 1953-11-03 Shell Dev Fuel oils
US2730464A (en) * 1951-05-17 1956-01-10 Shell Dev Antistatic treatment of textile yarns
CA521958A (en) * 1956-02-21 A. Winsor Philip Antistatic treatment of textile yarns

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA521958A (en) * 1956-02-21 A. Winsor Philip Antistatic treatment of textile yarns
US2050582A (en) * 1933-04-15 1936-08-11 Ig Farbenindustrie Ag Process of mercerizing cellulose material
US2165265A (en) * 1935-05-12 1939-07-11 Ig Farbenindustrie Ag Process of imparting hydrophobic properties to cellulose fibers
US2657984A (en) * 1950-10-20 1953-11-03 Shell Dev Fuel oils
US2730464A (en) * 1951-05-17 1956-01-10 Shell Dev Antistatic treatment of textile yarns

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282728A (en) * 1961-05-09 1966-11-01 Aquitaine Petrole Process for suppressing electrostatic charges on sulphur
US3548036A (en) * 1962-11-02 1970-12-15 Basf Ag Polymonoolefins containing an amine antistatic additive dispersed therein
US3297652A (en) * 1963-12-02 1967-01-10 Tomiyama Shinichi Method of suppressing electrostatc charges in synthetic resins and fibers
US3297653A (en) * 1963-12-02 1967-01-10 Tomiyama Shinichi Method of suppressing electrostatic charges in synthetic resins and fibers
US3523932A (en) * 1965-12-30 1970-08-11 Chem Y Thermoplastic composition
US3547863A (en) * 1966-01-28 1970-12-15 Hercules Inc Antistatic agents for high-polymeric compounds
US3449142A (en) * 1966-07-20 1969-06-10 Eastman Kodak Co Powder coated with an anti-static agent
US3514498A (en) * 1966-11-01 1970-05-26 Toray Industries Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist
US3549589A (en) * 1968-10-25 1970-12-22 Gen Tire & Rubber Co Color stabilized interpolymers of ethylene and vinyl acetate
US3630740A (en) * 1969-10-24 1971-12-28 Eastman Kodak Co Antistatic layers for polymeric photographic supports
US3902484A (en) * 1972-02-07 1975-09-02 Kimberly Clark Co Disposable surgical drape
US3867338A (en) * 1972-06-09 1975-02-18 Celanese Corp Thermal stabilization of polymers
US3925321A (en) * 1973-03-07 1975-12-09 Bayer Ag Polyamide compositions which have been rendered antistatic by the addition of sulfocarboxylic acid amides
US3974308A (en) * 1974-04-05 1976-08-10 Kimberly-Clark Corporation Method for treating a disposable surgical drape
US4083893A (en) * 1975-01-22 1978-04-11 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene
US4097546A (en) * 1976-03-30 1978-06-27 Allied Chemical Corporation Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene copolymers
US4061834A (en) * 1976-06-03 1977-12-06 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Durable antistatic coating for polymethylmethacrylate
US4346203A (en) * 1979-08-04 1982-08-24 Bayer Aktiengesellschaft Emulsifier for the preparation of polymers
US4272413A (en) * 1979-11-26 1981-06-09 Colgate-Palmolive Company Dialkylurea textile softening and antistatic agents
FR2470118A1 (fr) * 1979-11-26 1981-05-29 Colgate Palmolive Co Urees disubstituees ayant des proprietes assouplissantes et antistatiques, composition les contenant et leurs applications au traitement des tissus
DE3043570A1 (de) * 1979-11-26 1981-05-27 Colgate-Palmolive Co., 10022 New York, N.Y. Dialkylharnstoffe, ihre verwendung als weichmachendeund antistatisch wirkende mittel fuer textilien sowie diese mittel enthaltende wschmittelzusammensetzungen
US4694039A (en) * 1986-03-26 1987-09-15 Dsm Rim Nylon V.O.F. Stabilized lactam polymerization solutions
US5677357A (en) * 1995-07-05 1997-10-14 Cellular Technology International, Inc. Antistatic additive for organic polymer compositions
US5955526A (en) * 1995-07-05 1999-09-21 Cellular Technology International, Inc. Antistatic additive for organic polymer compositions
US20130323996A1 (en) * 2011-02-14 2013-12-05 Jnc Fibers Corporation Polyolefin-based antistatic fiber, being a single component or a conjugate type fiber, and nonwoven fabric including the same
KR20140010065A (ko) * 2011-02-14 2014-01-23 제이엔씨 주식회사 단일 성분 또는 복합형 섬유인 폴리올레핀계 제전섬유 및 이를 포함하는 부직포
US10174446B2 (en) * 2011-02-14 2019-01-08 Jnc Corporation Polyolefin-based antistatic fiber, being a single component or a conjugate type fiber, and nonwoven fabric including the same

Also Published As

Publication number Publication date
GB1014303A (en) 1965-12-22
DE1494008A1 (de) 1969-06-04
NL272600A (d)
CH409382A (de) 1966-03-15
BE611662A (fr) 1962-06-18

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