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US3898166A - Organic antistatic composition - Google Patents

Organic antistatic composition Download PDF

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US3898166A
US3898166A US324141A US32414173A US3898166A US 3898166 A US3898166 A US 3898166A US 324141 A US324141 A US 324141A US 32414173 A US32414173 A US 32414173A US 3898166 A US3898166 A US 3898166A
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composition
humectant
group
antistatic
vinyl
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US324141A
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William J Cooney
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ISP Investments LLC
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GAF Corp
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Priority to DE2401222A priority patent/DE2401222A1/de
Priority to FR7401152A priority patent/FR2324706A1/fr
Priority to JP49007467A priority patent/JPS5046581A/ja
Priority to CH41974D priority patent/CH41974A4/xx
Priority to CH41974A priority patent/CH576036B5/xx
Priority to BE139812A priority patent/BE809751A/fr
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Publication of US3898166A publication Critical patent/US3898166A/en
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Assigned to GAF CHEMICALS CORPORATION reassignment GAF CHEMICALS CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 04/11/1989 Assignors: DORSET INC.
Assigned to DORSET INC., A DE CORP. reassignment DORSET INC., A DE CORP. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 10, 1989 Assignors: GAF CORPORATION, A DE CORP.
Assigned to CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE reassignment CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GAF CHEMICALS CORPORATION, A CORP. OF DE
Assigned to ISP 3 CORP reassignment ISP 3 CORP ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GAF CHEMICALS CORPORATION
Assigned to ISP INVESTMENTS INC. reassignment ISP INVESTMENTS INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 06/06/1991 Assignors: ISP 3 CORP.
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Assigned to GAF CHEMICALS CORPORATION, GAF BUILDING MATERIALS CORPORATION, SUTTON LABORATORIES, INC. reassignment GAF CHEMICALS CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION)
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    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3562—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing nitrogen

Definitions

  • ABSTRACT An antistatic composition particularly adapted for use [211 32414l on textiles, floor coverings, and related materials, comprising an aqueous liquid fluid medium, having a 152] [1.5. CI. 252/8.75; 252/8.8; 252/545; p within the r ng of bo 7 o 13 and containing as 117/1395 CQ; 117/1395 F; l17/139.5 C active ingredient an organic antistatic textile agent [51] Int.
  • the humectant may be either a nonionic humec- 117/1395 (IQ 1395 F 1395 C tant (such as glycerine) or an ionic humectant (including strong electrolytes such as calcium chloride).
  • this invention relates to an antistatic composition particularly adapted for use on pile fabrics, especially carpeting and upholstery fabrics normally backed with polymeric coatings and on vinyl and asbestos sheet and tile flooring, polyurethane and polyolefin flooring and on linoleum petroleum composition flooring products and the like.
  • This invention is also concerned with a process for the preparation of an antistatic composition, and a process for treating the above with same in order to reduce electrostatic charge build-up in textiles.
  • antistatic pertains to reducing or eliminating the property or ability to generate, induce or accumulate electrostatic charges.
  • An object of this invention is the preparation of an improved antistatic composition.
  • Another object of this invention is the preparation of an antistatic composition which can be used in such a way that it does not attract dirt, is not worn off in normal use nor does same migrate to the surface of the textile structure when the latter is washed.
  • an object of this invention is the preparation of an antistatic composition which does not affect adversely the hand properties of the treated textile.
  • Still another object of the invention is the preparation of an antistatic composition which is compatible with the latex binders that are used as carpet backing and adhesives and is non-corrosive to the machinery from which same is applied to the textile structure.
  • Still other objects of this invention include the process for the preparation of the antistatic composition of this invention, the process for coating fabric therewith, a process for rendering textiles antistatic and a process for the reduction of static electricity charge build-up in humans in contact with flooring.
  • the antistatic material is effective without being in contact with the backing and the ends of the fibers of textiles or flooring wear layer.
  • the amount of material applied as such antistatic coating should be normally from .01 to 20 ounces per square yard and preferably from 2.0 to 10.0 ounces per square yard of the antistatic coating as applied.
  • the antistatic coating composition employed for the antistatic coating herein comprises a mixture of a textile antistatic agent and 10 to 50 parts by weight of humectant. There may also be employed from 0.1 to about 1 part by weight of a nonionic or cationic type wetting agent to assist in dispersing of the antistatic composition. It is also preferable to incorporate in the coating composition from about Olto about 1 part by weight of an electroltye particularly if the humectant employed is nonionic in character or is only wealky ionic, i.e., has a relatively low dissociation constant.
  • the antistatic coating is preferably applied in the form of an aqueous solution or dispersion, although other solvents or liquid dispersing mediums may be employed if desired and in the case of aqueous solutions or dispersions, volatile watersoluble solvents, such as lower aliphatic alcohols of one to four carbon atoms, acetone and the like, may be included to facilitate drying of the antistatic layer following its application.
  • compositions for the antistatic coating of the present invention are disclosed in U.S. Pat. No. 3,519,561 of Andrew J. Kelly and Robert C. Britt entitled Antistatic Cb mposition and Process. Particularly preferred are those antistatic compositions disclosed in said patent in which potassium formate is employed as humectant since it has been found that not only is potassium formate particularly effective as a humectant in such coating compositions, but compositions containing the same are compatible with the latex backing where employed, in carpets, for instance, and specifically overcomes premature coagulation or gelling of the backing based on natural compounded rubber, thus not interfering with good bonding of the latex coating with the carpet backing.
  • the antistatic coatings containing calcium chloride are incompatible with certain known latex coatings which have been used as carpet backings in that they cause premature coagulation or gelling ofthe latex with resultant poor adhesion of the latex to the carpet backing so that in the case of loosely woven or tufted carpets the latex does not function satisfactorily to hold the tufts in place.
  • antistatic layers based on the antistatic compositions of the above mentioned patent are particularly preferred, it will be understood that one may also employ many antistatic materials in conjunction with the specific parameters of the instant invention.
  • Such agents are normally nitrogen containing or carboxylic containing organic antistatic agents and as examples there may be mentioned the following compounds:
  • Bukester R1499 lauric acid polyethylene glycol ester Amine oxides or quaternary ammonium salts of N- vinyl lactams, such as vinyl pyrrolidonedimethylamino-ethylmethacrylate copolymers. N-vinyl lactam acrylamine copolymers such as a copolymer of 75% vinyl pyrrolidone and 25% acrylamide. Zelec DP lauryl alcohol phosphate. Catanac SN stearylamidopropyl dimethyl-B- wherein R represents the hydrocarbon residue of an alkanol (such as Alfol 1412) and n represents an integer of 8 to 30.
  • R represents the hydrocarbon residue of an alkanol (such as Alfol 1412) and n represents an integer of 8 to 30.
  • Esters of phosphoric acid and cthoxylated aliphatic alcohol such as the phosphate esters of lauryl alcohol condensed with 4 moles of ethylene oxide or of dodecyl alcohol condensed with about 2 moles of ethylene oxide
  • Polyglycol 4000 Sucrose octa-acetate
  • Polyethoxy amides of stearic and oleic acid Methyl diethanolamine ethoxylate Ethoxylated 2,3,7,9-tetramethyl-5-decyne-4,7-diol Polyoxyethylenemono-oleate Lauryl trimethyl ammonium chloride Undecylimidazolone Lauryl dimethylbenzyl ammonium chloride Polyoxyethyl stearyl ammonium chloride Oleic-monoisoproparol amide Vinyl acetate/styrene/acrylic acid polymers Ethoxylated diamines Long chain amine oxides CHg-CH o CH CH Hydroxybuty
  • the phosphate esters of the type referred to in said patents may be prepared by reacting 1 mole of P 0 with 2 to 4.5 moles of a nonionic surface active agent having the molecular configuration of a condensation product of at least 1 mole of ethylene oxide with 1 mole ofa compound containing at least six carbon atoms and a reactive hydrogen atom under substantially anhydrous conditions and at a temperature below about 1 10C.
  • the process does not require the use of an excess of the hydroxylic organic compound (in this instance the defined nonionic surface active agent), in order to bring the P 0 into solution.
  • Substantially no tertiary phosphate ester is formed and little or no P 0 remains in the composition.
  • the product may in some instances contain some unreacted nonionic surface active agent which for certain uses is actually advantageous.
  • Lighter colored or substantially colorless products are obtained when the phosphation reaction is carried out in the presence of a small or catalytic amount of a phosphorus-containing compound selected from the group consisting of hypophosphorous acid, salts of hypophosphorous acid, phosphorous acid, and salts and esters of phosphorous acid.
  • the process comprises reacting 1 mole of P 0 with 2 to 4.5 moles of a nonionic surface active agent having the molecular configuration ofa condensation product of at least 1 mole of ethylene oxide with 1 mole of a compound containing at least 6 carbon atoms and a reactive hydrogen atom, under substantially anhydrous conditions and at a temperature below about 1 10C. in the presence of a small amount of one or a mixture of the aforementioned hypophosphorous or phosphorous acid compounds.
  • Products resulting from the use thereof generally have VCS (varnish color scale, Gardner scale, standards of 1933) values of at least one less than products of the same process carried out in the absence of the hypophosphorous or phosphorous acid compound.
  • VCS variable color scale, Gardner scale, standards of 1933
  • Products having a VCS color of about I or less arethus made possible, as compared with VCS colors of from about 2 to 7 or more for products produced without the aid of the present invention.
  • the products have been found to resist discolorations or darkening even after storage for 3 to 6 months.
  • nonionic surface active agents employed as reactants are well known in the art and are disclosed along with suitable methods for their preparation in numerous patents and other publications. In general, they may be obtained by condensing a polyglycol ether containing the required number of alkenoxy groups or an alkylene oxide such as propylene oxide, butylene oxide, or preferably ethylene oxide, with an organic compound containing at least six carbon atoms and a reactive hydrogen atom.
  • a reactive hydrogen atom there may be mentioned alcohols, phenols, thiols, primary and secondary amines, and carboxylic and sulfonic acids, and their amides.
  • alkylene oxide or equivalent condensed with the reactive chain will depend primarily upon the particular compound with which it is condensed. As a convenient rule of thumb, an amount of alkylene oxide or equivalent should be employed which will result in a condensation product containing about 20 to 85% by weight of combined alkylene oxide. However, the optimum amount of alkylene oxide for attainmennt of the desired by hydrophobic hydrophilic balance may be readily determined in any particular case by preliminary test and routine experimentation.
  • the nonionic surface active agents having the molecular configuration of a condensation product of at least 1 mole of an alkylene oxide, preferably ethylene oxide, with 1 mole of a compound containing at least six carbon atoms and a reactive hydrogen atom are preferably polyoxyalkylene derivatives of alkylated and polyalkylated phenols, multi-branched chain primary aliphatic alcohols having the molecular configuration of an alcohol produced by the 0x0 process from a polyolefin of at least seven carbon atoms, and straight chain aliphatic alcohols of at least 10 carbon atoms.
  • these derivatives and other suitable nonionic surface active agents which may be phosphated in accordance with the present invention are included below.
  • E.O. means ethylene oxide and the number preceding same refers to the number of moles thereof reacted with 1 mole of the given reactive hydrogen-containing compound.
  • the latter agent is a solid at room temperature, it should be heated to above its melting point. Addition of the nonionic surface active agent to the P 0 is inadvisable since this has been found to result in the formation of tar and the like and to prevent the reaction from proceeding to completion. The reaction is exothermic and in some cases cooling is necessary to prevent the temperature from going above 110C. since this tends to produce discolored and darkened products. The reaction proceeds continuously during addition of the P 0 and solution thereof in the nonionic surface active agent, and is substantially complete or more by the time all of the P 0 has been added.
  • the few particles of solid P 0 remaining in the reaction medium may be removed at this point if time is of the essence, but it is preferred in the interests of economy to allow the reaction to proceed for an additional period of time which may range from one-half to 5 hours or more at ambient temperatures up to about C. until allof the P 0 has dissolved indicating complete reaction between the reactants involved. Vigorous agitation during the reaction is highly desirable to facilitate and expedite completion of the reaction.
  • the P 0 may be employed in dry, solid form as a granular powder or other finely divided or particulate form, for reaction with the above defined nonionic surface active agents.
  • the P 0 may first be dispersed in an inert organic diluent such as benzene, xylene, ether, pentane, or low and high boiling hydrocarbon fractions.
  • the reaction mixture may be cooled and discharged. If carried out under rigid anhydrous conditions the product should consist of a mixture of the primary and secondary phosphate esters of the nonionic surface active agent combined, depending upon the proportions of reactants, in some instances with a small proportion of unreacted nonionic surface active agent. Any small amount of water present in the reaction mixture will result protanto in the formation of some phosphoric acid in the product.
  • the degree of esterification in the product may be determined by potentiometric titration or by titration with alkali to methyl orange and then to phenolphthalein.
  • the products may be supplied in free unneutralized form, or in the form of the partially or completely neutralized salts containing as cations alkali metals, alkaline earth metals, metals, ammonium and organic amines. It is to be understood that such salts are to be regarded as the equivalent of the present products in their free form.
  • suitable cations there may be mentioned sodium, potassium, lithium, calcium, strontium, barium, magnesium, iron, tin, cad mium, aluminum, antimony, chromium, manganese, mercury, nickel, silver, zinc, ammonium and aliphatic, alicyclic, aromatic and heterocyclic organic amines such as the mono-, diand tri-methylamines, ethylamines, propylamines, laurylamines, stearylamines, ethanolamines, propanolamines, butanolamines, hexanolamines, cyclohexylamines, phenylamines, pyridylamines, morpholinylamines, and the like.
  • the above products may be modified by the addition to the reaction medium of a small amount of hypophosphorous or phosphorous acid compound.
  • a small amount of hypophosphorous or phosphorous acid compound Generally, about 0.0l to and preferably about 0.1 to 2% of such compound, based on the weight of the nonionic surface active agent being phosphated is sufficient to provide the desired improvements with respect to prevention of color degradation of the products and improvement in resistance of the products to color degradation in storage.
  • Hypophosphorous acid and its alkali metal salts e.g. sodium and potassium salts are generally preferred although any metal, alkaline earth metal, ammonium or amine salt of hypophosphorous acid or phosphorous acid may be employed, in addition to phosphorous .acid per se.
  • hypophosphorous acid when employed, it is preferred to use a 30 to 50% aqueous solution thereof although aqueous solutions of this acid and other of the water soluble hypophosphorous and phosphorous acid compounds may be employed in the form of aqueous solutions ranging in concentration from less than 5 up to 70% or more. It should be borne in mind that the reaction should be carried out under substantially anhydrous conditions and accordingly the water introduced in such solutions should be held to a minimum.
  • the salts of hypophosphorous acid and phosphorous acid employed herein may be in their hydrated or dehydrated form.
  • such salts there may mentioned aluminum, cadmium, sodium, potassium, lithium, calcium, strontium, barium, magnesium, ammonium, mono-, diand tri-methylamine, -ethylamine, -propylamine, -ethanolamine, and -propanolamine, pyridinyl, and morpholinyl phosphites and hypophosphites.
  • Esters of phosphorous acid may also be employed.
  • esters may be described as mono-. di-, and trialkyl, -aryl, and -cycloall 'yl phosphites. It will be understood that mixed esters are included.
  • the esterifying group generally contains from about one to 20 carbon atoms
  • hypophosphorous or phosphorous acid compound is preferably admixed with the non-ionic surface active agent prior to its addition to the nonionic surface active agent. It will accordingly be understood that the hypophosphorous or phosphorous acid compound or mixture thereof may be added at the start of the reaction or continuously or intermittently as the reaction proceeds.
  • the nonionic surface active agent is first charged to a reactor equipped with an agitator. If the charge is solid at room temperature, it is heated to melt the same. The additive referred to in the table is then added to and dissolved in the nonionic surface active agent with vigorous agitation. The solid granular P 0 is then charged to the reactor with vigorous agitation over a period ranging from about 5 minutes to about 1 hour and usually about 15 minutes. After the initial exothermic reaction subsides, the reaction mixture is heated to lO0c. and held at this temperature for about 5 hours after which the mixture'is cooled and discharged.
  • a sample of the reaction mixture is titrated with alkali to methyl orange and then to phenolphthalein as a control on the esterification.
  • the VCS color readings are measured in the prescribed manner. A reading of one is the lowest color reading measurable by this method, the highest being 18. Products prepared with the use of the additives referred to in the table sustained no change in color after 3 to 6 months storage.
  • Nonionic agent ionic parts Parts Additive VCS parts where employed Color I Nonylphenol+2 BOv 2,888 284 Control 2 CSIHXQCGH4(OC2H4)2OH 2 2,288 284 3.4 Hypophosphorous acid 1 3 Nonylphenol+4 15.0. 2,855 2l3 Control s HC6H4(OC2H4 )4 4 2,855 213 4.2 Hypophosphorous acid (50%) 5 Nonylphenol+6 E0.
  • a suitble quaternary ammonium compound may be represented by the following structural formula:
  • R (CHY),, CH and n 6 to 26; R" & R (CHY),,CH andn 0to 6.
  • the alkylmoiety may be branched or straight chain, y being hydrogen or an alkyl group as defined above. R and R need not be the same.
  • the quaternary ammonium compounds may be made in ways known in the art, such as for example by dissolving in isopropyl alcohol one mole of dimethyl stearyl amine; then from a separatory funnel add thereto one-half mole of diethyl sulfate keeping temperature below 50C; after the last of the diethyl sulfate is added and the exotherm is stopped, reflux for-l hour and cool. Evaporate the alcohol.
  • Preferred quaternary ammonium compounds include: compounds where R adn R" are lower alkyl, particularly preferred is wherein R or R" are methyl.
  • R may be C saturated or unsaturated, i.e., cocoa, stearic, oleic and the like.
  • the quaternized copolymers referred to may be those that are compounds which are first copolymerized and thereafter quaternized or those wherein the monomers are first quaternized and then copolymerized. Procedures known in the art for carrying out the above processes may be employed.
  • the quaternary copolymers employed are those which have unit I and either unit ll or Ill or all three units.
  • R I E t ⁇ CH CH2 C l m n c o CH CH-CH or C H where x 2-18; R is CH or C H ;R is CH 2 57 X is Cl, Br, 1, S0 H CH SO and M is a monomeric unit resulting from the heteropolymerization employing an optional mono vinyl monomer different from and copolymerizable with n. M may also be 5 to 40 where p is 0 to 50, the latter occurring where n, m and p are all employed.
  • such quaternary copolymers are prepared by the copolymerization of an N-vinyl lactam, such as N-vinyl pyrrolidone and di-loweralkylaminoalkyl (or hydroxy alkyl) acrylate or methacrylate, and optionally a further mono vinyl monomer different from and copolymerizable with n.
  • N-vinyl lactam such as N-vinyl pyrrolidone and di-loweralkylaminoalkyl (or hydroxy alkyl) acrylate or methacrylate
  • a further mono vinyl monomer different from and copolymerizable with n.
  • the monomers are copolymerized in accordance with the present invention so that based upon 100 mole percent, the vinyl pyrrolidone units are present in an amount of 40 mole percent, the units derived from the diloweralkylaminoalkyl (or hydroxy alkyl) acrylate or methacrylate constitute from 10 to 60 mole percent, and the units derived from said further copolymerizable vinyl monomer also constitute from 10 to 60 mole percent.
  • n 40 90 mole percent
  • m is l0 60 mole percent
  • p is from 10 60 mole percent
  • R represents an alkylene bridge group necessary to complete a five, six or seven-membered heterocyclic ring system
  • R represents either hydrogen or a methyl group
  • n represents a number indicative of the extent of polymerization and is usually at least 3 or 4.
  • polymeric N-vinyl lactams are commercially available and called polymeric N-vinyl lactams. They are obtained by polymerizing organic five, six or sevenmembered ring compounds containing in their rings the -NH-CO-group, such as, for example,
  • N-vinyl-Z-pyrrolidone is most preferred as it is readily available and provides products having excellent properties.
  • the optional mono vinyl or vinylidene monomer represented by M in the above structural formula can comprise any conventional vinyl monomer copolymerizable with N-vinyl pyrrolidone.
  • suitable conventional vinyl monomers include the alkyl vinyl ethers, e.g., methyl vinyl ether, ethyl vinyl ether, octyl vinyl ether, etc; acrylic and methacrylic acid and esters thereof, e.g., methacrylate, methyl methacrylate, etc.; vinyl aromatic'monomers, c.g., styrene, a-methyl styrene, etc.; vinyl acetate; vinyl alcohol; vinylidene chloride; acrylonitrile and substituted derivatives thereof; methacrylonitrile and substituted derivatives thereof; acrylamide and methacrylamide and N-substituted derivatives thereof; vinyl chloride, crotonic acid and esters thereof; etc.
  • copolymerizable vinyl monomers can comprise any conventional vinyl monomer copolymerizable with N-vinyl pyrrolidone and where a terpolymer is formed, copolymerizable with both units n and m, and being different from both.
  • the preferred quaternized copolymers employed in the present invention can be characterized as having a repeating structural unit derived from A. 40 90 mole of vinyl lactam;
  • copolymers are conveniently prepared by subjecting a solution of vinyl lactam and the amino acrylate or amino methacrylate monomer with or without an optional copolymerizable vinyl monomer to conditions conducive to vinyl polymerization through the double bond.
  • polymerization may suitably be initiated by the action of free radicals, the polymerization proceeding exothermically once initiated.
  • Suitable free radical catalysts conveniently employed and suitably-utilized in accordance with the production of the copolymers include organic and inorganic peroxides, e.g., hydrogen peroxide, t-butyl peroxide, etc., aliphatic azo compounds, e.g., azobisisobutyronitrile as well as other free radical forming catalysts well known in the polymerization art.
  • the polymerization is preferably carried out in solution at temperatures varying from about 50C to 100C or more; however, to avoid run away conditions and to obtain a copolymer of a desirable molecular weight it is sometimes preferred to carry out the copolymerization at a temperature of from about to about C.
  • the copolymerization reaction is preferably carried out in the absence of free-oxygen, conveniently under a blanket of an inert gas, such as, nitrogen, argon or the like, or at atmospheric pressure.
  • the copolymers are in the form of their quaternary salts. Accordingly, after completion of the polymerization reaction the polymer is submitted to a treatment conducive to quaternization of the tertiary amino group, utilizing a conventional quaternizing agent.
  • suitable quaternizing agents include, such as, dialkyl sulfates, e.g., dimethyl sulfate, diethyl sulfate, etc.; alkyl sulfonic acid, e.g., methyl sulfonic acid, ethyl sulfonic acid, ethyl sulfonic acid, etc.; benzyl halides, e.g., benzyl chloride, benzyl 2. Alkylbcnzine Sulfonates R bromide, benzyl iodide, etc.; alkyl halide, etc. Accordingly, any conventional quaternizing agent can be advantageously employed in the production of the quaternary N-vinyl pyrrolidone copolymers used in the compositions of the present invention.
  • the molecular weight of the quaternized copolymers should be between 800 and 5,000.
  • Operative group 1A, 11A and 11B metal sulfonates and sulfates include compounds of the following generic formulae:
  • Alkylaryl Sulfonatos i.e. Naccanol SO3H
  • R CH -(CH 3 2 n
  • Ethoxylaized Alcohol Sulfonates i.e. Alipols
  • Alkyl Napthalone Sulfonates i.e., Nekal 815-75) 7. Igepon A a 8.
  • Igepon T's R-C-N 'and R" are alkyl or aromatic groups) -caz -cn -so Na It is to be understood that any one of the above components may be used in place of the alkoxylated tertiary amine, however, the humectant (and where needed, the electrolyte) must still be employed in conjunction therewith.
  • antistatic layers are based on alkoxylated tertiary amines represented by the following general formula:
  • R represents an aliphatic hydrocarbon radical of from about eight to about 22 carbon atoms, each R; represents hydrogen or methyl and n represents an average integer of at least 1, preferably l to about 30, although higher alkoxylated derivatives, i.e., the products obtained by condensing 1 molar proportion of a primary aliphatic (saturated or unsaturated) amine with up to molar proportions of an alkylene oxide, usually ethylene oxide, may be employed if desired.
  • alkoxylated amines are well known in the art and are prepared by condensing the-primary saturated or unsaturated aliphatic amine of from eight to 22 carbon atoms, with an alkylene oxide, usually ethylene oxide, although propylene oxide and butylene oxide may be employed if desired, until glycol groups of desired chain length are obtained.
  • alkylene oxide usually ethylene oxide, although propylene oxide and butylene oxide may be employed if desired, until glycol groups of desired chain length are obtained.
  • Such products have been disclosed, for example in U.S. Pat. Nos. 1,970,578; 2,174,762; 2,510,284 and 2,593,466.
  • humectant in the composition of the present invention there may be used various deliquescent salts of metals of the Groups 1 and 11, Periodic Table, particu larly of the alkali metal and alkaline earth metals.
  • Specific deliquescent salts which are preferred as humectant include the alkali metal salts of lower aliphatic carboxylic acids, such as sodium formate, potassium formate, lithium formate, cesium formate, sodium and potassium acetate, potassium butyrate and mineral acid salts like calcium chloride.
  • organic humectants as glycerol, urea, ethylene glycol, sorbitol, ethoxylated sorbitol, lauric acid esters and mixtures of the same.
  • a deliquescent salt may also function as an alectroltye.
  • glycerine or other nonionic humectants are employed, they should be combined with an electrolyte.
  • deliquescent salts such as sodium and potassium formate which have a relatively low dissociation constant
  • Salts which are not particulary deliquescent, such as sodium chloride, sodium sulfate or potassium nitrate do not function wholly satisfactorily as both humectant and electrolyte and can be employed in combination with a nonionic humectant, such as glycerine or urea or in combination with a more highly deliquescent salt, such as potassium formate or calcium chloride.
  • a nonionic humectant such as glycerine or urea
  • a more highly deliquescent salt such as potassium formate or calcium chloride.
  • the humectant and electrolyte may be either a single compound or a mixture of compounds.
  • the antistatic composition of the present invention 5 preferably comprises a combination of (i) certain orgredients are preferably prepared in the form of an aqueous liquid fluid medium so that they can be applied to the material to be protected in the form of an aqueous solution, dispersion, gel, viscous mass or the like.
  • composition of the present invention comprises a mixture of the above components in the following relative proportions in which the parts are by weight.
  • the particular humectant employed is also a strong electrolyte the amount employed as a humectant is sufficient to function as an electrolyte.
  • the particular humectant is not a strong electrolyte then from 0.01 part to about 0.01 part ofa strong electrolyte is employed.
  • Both components are prepared in the form of a concentrated aqueous solution or dispersion.
  • wetting agents of the nonionic or cationic type.
  • Such wetting agents may be used in amounts of from 0.01 to 0.1 part by-weight and are preferably included in the composition when a heavy pile fabric, particularly carpeting is being treated, as they facilitate the penetration of the antistatic composition into the textile substrate where so desired.
  • the use of the wetting agent is not as impor tant.
  • Other materials which can be incorporated in the composition include coloring agents, including dyes and pigments, fillers and similar additives, antioxidants, additional antistatic agents, stabilizers and defoaming agents.
  • coloring agents including dyes and pigments, fillers and similar additives, antioxidants, additional antistatic agents, stabilizers and defoaming agents.
  • volatile water soluble solvents such as lower alcohols of one to four carbon atoms, acetone and the like in order to faciliate the removal, by vaporization, of excess water.
  • the antistatic coating composition of the present invention is prepared by dissolving the several components, alkoxylated amine, combined humectant and electrolyte or humectant and an electrolyte in water, the order of addition being immaterial and mixing at from room temperature to about 100C for a sufficient length of time until a uniform composition is obtained.
  • a salt of a lower carboxylic acid is employed as the humectant or combined humectant and electrolyte, it may be formed in situ by adding carboxylic acid having from about one to about five carbon atoms and an alkali metal or alkaline earth metal base, i.e., hydroxide or carbonate, such as sodium, potassium lithium or cesium hydroxide or carbonate.
  • the pH of the resulting mixture or solution is adjusted so as to be within the range of pH 7 to 13, more preferably to a pH within the range of from about 9 to about 1 l, with the most preferred pH being about 9.
  • This pH adjustment is preferably effected by adding an alkali or an organic amine to the mixture and if the alkali salt of a lower carboxylic acid is employed as humectant and/orelectrolyte, it is pref- :16 erable that the pH adjustment be effected using the same alkali base as the anion present in such salt. It will be appreciated that this pH adjustment by addition thereof also results in the formation of a salt of the alkoxylated amine.
  • neutralizing agents there'may be employed aikalis, such as, KOH, NaOH,Ca(O1-l) ,Na CO ammonia, diethanol amine, triethanol amine, morpholine and other organic amines and the like.
  • the latter may be thickened or made viscous by the addition thereto of .l to 20% by wt. of common thickness such as, sodium polyacrylates; acrylic acid; methyl cellulose, hydroxy ethyl cellulose; starch and the like.
  • the antistatic composition of the present invention is particuarly useful for the production of the antistatic textile products described and claimed in US. Pat. Nos. 3,510,386 and 3,519,561 both of which also more fully describes the preferred method of application.
  • the prefered method of application of the antis 'ic composition of the present invention to textiles is .ustrated diagrammatically in the annexed sheet of drawings; in which 2 designates a roll of textile material, such as carpeting or upholstery, preferably of pile construction, to be treated.
  • the web of textile 4 which may contain a polymeric latex pre-coat over the primary backing is removed from the roll by drive rollers 14 and passes over coating means 6, here illustrated as a spray head which applies the coating composition to the back of the textile, to the underside of the primary backing or that of the latex pre-coat.
  • coating means 6, here illustrated as a spray head which applies the coating composition to the back of the textile, to the underside of the primary backing or that of the latex pre-coat.
  • the web of textile then passes through drying unit 8 illustrated diagrammatically in the drawing as a drying oven, wherein it may be subjected to radiant heat and/or heated atmosphere to effect evaporation of most of the water.
  • the temperature of the surface of the textile will not exceed 212F., but a surrounding atmosphere having temperatures of from 300 to 400F may be employed subject to the practical limitation that the temperature must not be so high as to affect decomposition or degradation of the textile substrate (latex pre-coat) or the antistatic coating composition.
  • the web of textile passes through suitable apparatus illustrated in the drawings as coating roll 10 for applying a latex backing to the fabric. 1n the case of a loosely woven or tufted carpet structure the latex backing is applied in the manner customary in the art so as to as sure uniform coating and good adhesion of the latex to the backing and looped ends of the pile.
  • any conventional latex backing may be employed, particularly preferred is the compounded natural rubber latexes, such as Lotol GX-13 14.
  • compounded neoprene latexes such as Lotol GX-l076'and latexes of polystyrene, vinylidene chloride polyacrylates, butadiene-styrene or'others.
  • the antistatic composition can be applied in any coating weight which is capable effecting the desired antistatic properties.
  • the broad dry coating weight range is from .01 to 20 oz. per sq. yd. with a more preferred range being 2.0 to 10 oz. per sq. yd.
  • a more preferred dry coating weight for carpet is 4-6 oz. perzsq. yd.
  • the broad dry coating weight range is from above to about 4.0% based on fabric weight.
  • a more preferred dry coating range for textiles is from about 0.8% to about 3.0% based on fabric weight.
  • a most preferred dry coating weight for textiles is 2.0% based on fabric weight.
  • the antistatic composition was prepared by adding the base and organic acid to water to form the humectant in situ.
  • the alkoxylated amine employed was stearyl amine which had been ethoxylated with moles of ethylene oxide per mole of amine.
  • the wetting agent when employed was tridecyl alcohol which had been ethoxylated with 6 moles of ethylene oxide per mole of alcohol.
  • the thus prepared antistatic composition is then neutralized with 45% alkali (i.e., KOH) to a pH of 6.0-8.0. This neutralization is then continued to a pH of 9-13 by employing an amine (i.e., triethanol amine).
  • the antistatic composition may be carried out either to the exclusion of raising the pH thereof or in addition thereto by adding to the composition .1 to 10% by weight, preferably .2 to 2% of one of said thickening agents.
  • the amounts of materials employed in each example are given in the appropriate column of Table I.
  • the antistatic coating was applied to the back of a tufted carpet having a primary loosely woven jute backing rather than to the underside of a pre-coat latex; the type of fibers employed in the tufted pile are given in Table I as well as the amount of antistatic composition applied. After application of the antistatic coating the carpet was dried to remove excess moisture. A latex coating was then applied over the antistatic coating in such a manner that it did not encapsulatethe latter where no polymeric pre-coat latex had been employed.
  • the testing procedure used in these examples was the AATC-l 34-1969 Test.
  • EXAMPLE I The acidic antistatic composition (pH 4-7) was neutralized with 45% KOH to 6.0 6.5 pH. This neutralization was continued with triethanol amine to pH 9.0. The thus neutralized antistatic composition was applied to the back of a tufted carpet of plush style with nylon face yarn and a woven polypropylene primary backing by roller coating. Wet application weights of 5.2 oz. per sq. yd. were achieved (determined by a chloride ion determination). The treated carpet was dried and subsequently laminated to jute using an adhesive compound consisting of carboxylated styrene-butadiene latex loaded to 350 parts with whiting. Static test results by AATC-l 34-1969 at 20% relative humidity were taken. Untreated carpet under same AATC-134-l969 test procedure were also taken. The results appear in Table l. The threshold for human shock sensitiity is generally accepted as or 2,800 volts by this test procedure.
  • EXAMPLE II The acidic antistatic composition was neutralized to pH 9.0 with KOH and applied to a shag carpet with nylon face yarn and polypropylene backing. The composition was applied to back of the lock of the carpet at various wet application levels, dried and laminated to a jute secondary backing with a natural latex adhesive.
  • EXAMPLE VI EXAMPLE V Example IV was repeated except that a secondary jute backing was applied. Substantially the same results were obtained.
  • Example IV was repeated using a woven carpet consisting primarily of wool fibers. Substantially the same results were obtained.
  • EXAMPLE VI A thickened antistatic medium (400 cps LVF- Spindle No. 3, speed 10) was prepared and employed on a shag carpet that had exhibited migration problems. There was no evidence of migration on the carpet after treatment.
  • Example IV was repeated except that an unthickened antistatic composition was used. Substantial migration to the surface took place after shampooing and soaking in water.
  • EXAMPLE 1X Example IV was repeated but at 2,000 cps (Brookfield LVF No. 3 at 12 RPM). Substantially no antistatic composition migrated to the surface after shampooing and soaking in water.
  • EXAMPLE X Example IV was repeated but at 500 cps (Brookfield LVF No. 3 at 12 RPM). Migration of antistatic composition to the surface was substantially reduced as compared to the standard antistatic composition having a viscosity of 5 cps (Brookfield LVF No. 1 at 60 RPM).
  • EXAMPLES 24 to 41 In these examples the samples treated were nylon and wool tufted carpet structures. in most cases the antistatic coating was applied to the base of the carpet fibers and primary jute and dried. A latex coating was then applied over the antistatic coating.
  • the humectant was formed in situ by the reaction of a basic component with an acidic plied to the fabric and dried at a temperature of from about 200 to 325F for a period of time of from about 10 to 30 minutes.
  • the dired fabric was then conditioned for at least 6 hours at a temperature of 70:t5F
  • the test procethe test results and other pertinent information for dure consists essentially of a means of controlled rubthese examples are given in Table II and IV. bing of a strip of fabric across a pair of static-generating X P 42 (Teflon) bars and across a stainless steel bar which I S to 56 transfers the friction generated charge to an electro- In these examples the samples treated were nylon and static voltmeter for measurement. This testing was conwool tufted carpet structures.
  • the humectant was not formed in EXAMPLES 85-] I3 situ but instead was added directly to the antistatic I n these examples the samples treated were convencomposrtlon.
  • the antistatic The composition of the antlstatic coating as well as coating was applied to the back of the textile sample the test results and other pertment information for t se exam S are iven in Tables v & VI and dried to remove excess moisture.
  • a polymeric P g backing was then applied to the fabric and cured at a EXAMPLES 57 83 temperature of from 200-235 F for from 10-30 minutes.
  • the coated material was then tested on an Atlab In these examples the samples treated were conven- Tester 1n the manner described above in connection tional woven and nonwoven fabrics. In most cases the with Examples 57-83.
  • the humectant antistatic coatmg was applled to the textile and drled to was not formed in situ, but instead was added directly remove the excess morsture. The amme utilized was in to the antlstatrc composltion. accordance with the description glven 1n accordance The composition of the antistatic coatmg as well as with Examples 1 to 25.
  • R represents an aliphatic hydrocarbon radical of from about eight to 22 carbon atoms, R represents a member of the group consisting of hydrogen and methyl and n represents an average integer of from 1 to 51; a quaternary ammonium compound; a phosphate ester; alkali metal salts of C sulfated alcohols and sulfonated C esters of carboxylic acids; and
  • a humectant selected from the group consisting of anionic and nonionic humectants, and when said humectant is a nonionic humectant, a strong electrolyte, said electrolyte being neutral salt of a strong base and a strong acid.
  • said quaternary ammonium compound is a quaternized copolymer of N-vinyl lactam and a monovinyl monomer copolymerizable therewith.
  • N-vinyl lactam has the formula Hz -CH3 R N-R' wherein R (CHY), CH and n 6 to 26 and R" and R (CHY),, -(CH and n 0 to 6, Y hydrogen or alkyl.
  • composition as defined in claim 1 additionally containing .1 to by wt. of a thickening agent.
  • composition as defined in claim 5, wherein said thickening agent is selected from the group consisting of hydroxyethyl cellulose, methyl cellulose, acrylic acid and starch.
  • composition as defined in claim 1 said humectant being selected from the group consisting of deliquescent alkali metal salts of lower alkyl carboxylic acids, calcium carbonate, glycerol, urea, ethylene glycol, sorbitol, ethoxylated sorbitol lauric acid esters, and mixtures thereof.
  • composition as defined in claim 1- wherein the humectant is calcium chloride.
  • humectant is a deliquescent alkali metal salt of a lower alkyl carboxylic acid having from one to four carbon atoms and there is present as an electrolyte at least 0.01 parts by weight of a compound selected from the group consisting of sodium chloride and calcium chloride.
  • humectant is a nonionic humectant selected from the group consisting of sorbitol humectants, glycerol and urea, and there is present as an electrolyte at least 0.01 parts by weight of an electrolyte selected from the group consisting of sodium chloride and calcium chloride.
  • composition as defined in claim 1 wherein said humectant is an ethoxylated sorbitol lauric acid ester.
  • component (a) is N-octyl-N-ethyl morpholinium ethosulfate.
  • component (a) is a phosphate ester.
  • phosphate ester is a phosphate ester of a nonionic surface active condensation product of at least 1 mole of ethylene oxide with 1 mole of a compound containing at least six carbon atoms and a reactive hydrogen atom.
  • a process for the preparation of an antistatic coating composition comprising an aqueous liquid fluid medium having a pH in the range of from about 7 to 13 and containing as essential active material a member selected from the group consisting of a. one part by weight of an alkoxylated tertiary amine having the formula wherein R represents an aliphatic hydrocarbon radical of from about eight to 22 carbon atoms, R represents a member of the group consisting of hydrogen and methyl and n represents an average integer of from 1 to 51; a quaternary ammonium compound; a phosphate ester; alkali metal salts of C sulfated alcohols and sulfonated C esters of carboxylic acids; and
  • humectant selected from the group consisting of anionic and nonionic humectants, and when said humectant is a nonionic humectant, a strong electrolyte, said electrolyte being a neutral salt of a strong base and a strong acid, comprising adding substantially equimolar amounts of an alkali metal base and an aliphatic carboxylic acid having from one to four carbon atoms to water to thereby produce the humectant in situ, adding thereto the active material and thoroughly mixing the same to obtain a uniform composition, and adding to the mixture a neutralizing base in such amount as to adjust the pH of such mixture within the range of 7-13.
  • a humectant selected from the group consisting of anionic and nonionic humectants
  • a strong electrolyte said electrolyte being a neutral salt of a strong base and a strong acid

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
US324141A 1973-01-16 1973-01-16 Organic antistatic composition Expired - Lifetime US3898166A (en)

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US324141A US3898166A (en) 1973-01-16 1973-01-16 Organic antistatic composition
DE2401222A DE2401222A1 (de) 1973-01-16 1974-01-11 Antistatische beschichtungsmasse und verfahren zu ihrer herstellung
JP49007467A JPS5046581A (fr) 1973-01-16 1974-01-14
CH41974D CH41974A4 (fr) 1973-01-16 1974-01-14
CH41974A CH576036B5 (fr) 1973-01-16 1974-01-14
FR7401152A FR2324706A1 (fr) 1973-01-16 1974-01-14 Compositions antistatiques pour textiles et revetements de sol et procede pour leur preparation
BE139812A BE809751A (fr) 1973-01-16 1974-01-15 Compositions antistatiques pour textiles et revetements de sol et procede pour leur preparation

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4707414A (en) * 1984-04-09 1987-11-17 General Dynamics, Pomona Division Electrostatic-free package
KR20010109514A (ko) * 2001-11-19 2001-12-10 손진기 영구적인 대전방지성을 갖는 아크릴 패널의 제조방법
WO2002004738A2 (fr) * 2000-07-12 2002-01-17 Kimberly-Clark Worldwide, Inc. Composition antistatique
US6368384B1 (en) * 2000-07-12 2002-04-09 Clearwater, Inc. Desiccant tablets for gas drying
US6506233B2 (en) 2000-07-12 2003-01-14 Clearwater, Inc. Desiccant tablets for gas drying
US20060239900A1 (en) * 2005-04-20 2006-10-26 Cabot Corporation Methods of forming an alkali metal salt
US20090156079A1 (en) * 2007-12-14 2009-06-18 Kimberly-Clark Worldwide, Inc. Antistatic breathable nonwoven laminate having improved barrier properties
US20120196992A1 (en) * 2009-09-23 2012-08-02 Basf Se Synergistic antistatic compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165290A (en) * 1978-03-13 1979-08-21 The Procter & Gamble Company Fabric care composition containing starch and quaternary ammonium compound
JPS5721429A (en) * 1980-07-14 1982-02-04 Unitika Ltd Modification of polyamide film

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3652419A (en) * 1968-03-06 1972-03-28 Witco Chemical Corp Antistatic fiber lubricant
US3658573A (en) * 1969-04-08 1972-04-25 Eastman Kodak Co Support provided with antistatic layer

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3652419A (en) * 1968-03-06 1972-03-28 Witco Chemical Corp Antistatic fiber lubricant
US3658573A (en) * 1969-04-08 1972-04-25 Eastman Kodak Co Support provided with antistatic layer

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4707414A (en) * 1984-04-09 1987-11-17 General Dynamics, Pomona Division Electrostatic-free package
WO2002004738A2 (fr) * 2000-07-12 2002-01-17 Kimberly-Clark Worldwide, Inc. Composition antistatique
US6368384B1 (en) * 2000-07-12 2002-04-09 Clearwater, Inc. Desiccant tablets for gas drying
WO2002004738A3 (fr) * 2000-07-12 2002-08-29 Kimberly Clark Co Composition antistatique
US6506233B2 (en) 2000-07-12 2003-01-14 Clearwater, Inc. Desiccant tablets for gas drying
KR20010109514A (ko) * 2001-11-19 2001-12-10 손진기 영구적인 대전방지성을 갖는 아크릴 패널의 제조방법
US20060239900A1 (en) * 2005-04-20 2006-10-26 Cabot Corporation Methods of forming an alkali metal salt
US20090156079A1 (en) * 2007-12-14 2009-06-18 Kimberly-Clark Worldwide, Inc. Antistatic breathable nonwoven laminate having improved barrier properties
WO2009077889A1 (fr) 2007-12-14 2009-06-25 Kimberly-Clark Worldwide, Inc. Stratifié non-tissé respirant antistatique possédant des propriétés barrières améliorées
US20120196992A1 (en) * 2009-09-23 2012-08-02 Basf Se Synergistic antistatic compositions

Also Published As

Publication number Publication date
CH41974A4 (fr) 1975-11-28
BE809751A (fr) 1974-05-02
CH576036B5 (fr) 1976-05-31
DE2401222A1 (de) 1974-07-25
FR2324706B1 (fr) 1978-02-10
JPS5046581A (fr) 1975-04-25
FR2324706A1 (fr) 1977-04-15

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