US3864317A - Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same - Google Patents

Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same Download PDF

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US3864317A
US3864317A US284863A US28486372A US3864317A US 3864317 A US3864317 A US 3864317A US 284863 A US284863 A US 284863A US 28486372 A US28486372 A US 28486372A US 3864317 A US3864317 A US 3864317A
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sodium
poly
antistatic agent
ether sulfate
trioxyethylene
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Yuzuro Ogata
Yukihisa Niimi
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Kao Corp
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Kao Corp
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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
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • 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
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • 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
    • Y10S260/18—High polymeric, resinous, antistatic agents containing pentavalent nitrogen
    • 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
    • Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S526/923—Ethylenic monomers containing at least one salt group

Definitions

  • ABSTRACT Hydrophobic fibers and fibrous structures having durable antistatic property and a process for producing such hydrophobic fibers and fibrous structures also are provided, by utilizing the above antistatic agent.
  • the present invention relates to a novel antistatic agent soluble in organic solvent which can afford durable antistatic property, highly resistant to washing and dry cleaning, to hydrophobic fibers made of such polymers as polyester, polyacrylic, polyamide, polyvinylchloride, polyethylene and polypropylene polymers as well as fibrous structures such as cloth and knit fabrics made of such fibers, if applied to those fibers of fibrous structures in an organic solvent system.
  • the present invention relates to hydrophobic fibers and fibrous structures having durable antistatic property and a method for producing such fibers and fibrous structures.
  • Hydrophobic fibers and fibrous structures made of such fibers as mentioned above have excellent properties such as toughness and chemical resistance, but, as they are hydrophobic, they have great volume specific resistance and, therefore. they tend to produce a remarkable static electrification phenomenon even by a slight friction, thus causing various electrostatic faults.
  • Such faults will not only hinder a normal operation of the process steps for producing textile goods from textile fibers, for example, drawing and twisting, winding, warping, knitting and weaving, sewing, etc., but also cause lowering of product qualities or various troubles such as stains on products due to dust absorption and unpleasant feelings to human bodies.
  • the former method has disadvantages such as the low dispersibility of the antistatic agent is liable to cause breaking of yarns and occurence of knotted yarns during melt spinning or lowering of qualities such as reduction of strength and elasticity. Further, due to thermal deterioration caused in melt spinning, dispersion into the coagulating bath in wet spinning, etc., only special kinds of antistatic agent can be used.
  • the latter method is a temporary antistatic treatment method, in which, since the antistatic agent is stripped off by washing, the antistatic effect is gradually lowered or completely lost, which has not only the disadvantage of hurting the feeling of fibrous structures, but also has a greater disadvantage of not having a durable antistatic effect.
  • fibrous structure means staple fibers, continuous filaments, woven fabrics, knitted fabrics, non-woven fabrics, battings and the like.
  • the primary object of the present invention is to provide an antistatic agent which is soluble in an organic solvent to form a stable solution and which has a high resistance against washing and dry cleaning when applied to hydrophobic fibers or fibrous structures.
  • Another object of the present invention is to provide fibers and fibrous structures having durable antistatic property and also having excellent hand.
  • Another object of the present invention is to provide a process for producing fibers and fibrous structures having durable antistatic property and also having excellent hand easily on an industrial scale and economically.
  • the above objects of the invention can be attained by using, as the durable antistatic agent to be used in an organic Solvent medium or system, a complex compound consisting of a polyvinyl derivative having a quaternary ammonium group in its side chain and having a counter anion derived from a particular anionic surfactant or an amphoteric surfactant as defined below.
  • a fibrous structure is treated with a cationic polymer as an antistatic agent, it is generally apt to be given a hard hand feeling.
  • the antistatic agents according to the present invention are used, a desirable soft hand can be imparted to the textile material. This is one of characteristic features of the invention.
  • the durable antistatic agent for solvent system of the present invention comprises a complex compound consisting of a polyvinyl derivative having a quaternary ammonium group in its side chain, the counter anion thereof being substituted with at least one surface active compound selected from the group consisting of anionic surfactants containing 2 8 ethylene oxide units, ester-bonded sulfonates, alkylamidocarboxylic acid salts amphoteric surfactants of the carboxylic acid type.
  • the present invention provides hydrophobic fibers and fibrous structures having durable antistatic property which contain 0.1 to l()% by weight ofa com- 3 plex compound consisting ofa polyvinyl derivative having a quaternary ammonium group in its side chain, the counter anion thereof being substituted with at least one surface active compound selected from the group 1 consisting of anionic surfactants containing 2 8 ethylene oxide units, esterbonded sulfonates. alkylamidocarboxylic acid salts and amphoteric surfactants of the carboxylic acid type.
  • the process of the present invention comprises treating a hydrophobic fibrous structure with an organic solvent solution consisting of 0.05 to 10% by weight of a complex compound consisting of a polyvinyl derivative having a quaternary ammonium group in its side chain, the counter anion thereof being substituted with at least one surface active compound selected from the group consisting of anionic surfactants containing 2 8 ethylene oxide units, esterbonded sulfonates, alkylamidocarboxylic acid salts and amphoteric surfactants of the carboxylic acid type, 0.05 to by weight of alcohols and more than 70% by weight of at least one organic solvent selected from the group consisting of hydrocarbons, halogenated hydrocarbons, ethers, ketones and esters, the weight ratio of said alcohols to said complex compound being more than 0.2/1.
  • an organic solvent solution consisting of 0.05 to 10% by weight of a complex compound consisting of a polyvinyl derivative having a quaternary ammonium group in its side chain, the counter anion thereof being
  • polyvinyl derivatives having quarternary ammonium groups in their side chains to be used in the present invention are those obtained by, for example, the following processes:
  • a process which comprises homopolymerizing a vinyl monomer having at least one tertiary amine residue in the molecule or copolymerizing the same with another copolymerizable vinyl monomer and then quaternizing the resulting polymer by a suitable quaternizing agent, or
  • the vinyl monomers having at least one tertiary amine residue in the molecule are those represented by the general formula:
  • the vinyl monomers having at least one quaternary ammonium group in the molecule are those represented by the general formula:
  • coocn ca n a x wherein R and R,-, are vinyl residues. and preferably R, represents hydrogen or methyl and R represents an alkoxycarbonyl group. alkoxy group. CONH- COOH, -CN or C H
  • Particularly preferred copolymerizable vinyl monomers are acrylic acid. acrylic esters, acrylonitrile. styrene and acrylamides.
  • the molar ratio of the vinyl monomer having a tertiary amine residue or vinyl monomer containing quaternary ammonium group to the other copolymerizable vinyl monomer is properly 1:0-1.
  • the complex compound of the present invention comprises the above polyvinyl derivative containing quaternary ammonium groups in its side chains, but the counter anion thereof being substituted with a particular anionic surfactant or amphoteric surfactant.
  • anionic surfactants there may be used at least one anionic surfactant selected from the group consisting of anionic surfactants containing 2 8 ethylene oxide units (preferably 3 5 ethylene oxide units), esterbonded sulfonates and alkylamidocarboxylic acid salts.
  • amphoteric surfactants are those of carboxylic acid type.
  • the antistatic agent of the present invention that is to say, the complex compound as mentioned above, is applied to the textile material (textiles or fabrics) in an amount of 0.1 to 10% by weight, preferably 0.2 to 3% by,weight, most preferably 0.3 to 1.0% by weight.
  • the attached amount is less than 0.1% by weight, the antistatic effect is still insufficient, while. when it exceeds 10% by weight, the hand or feeling of the finished textile material is remarkably lowered, though the antistatic effect is improved.
  • the hydrophobic fibers to be treated in the present invention include polyesters, polyacrylonitrile, polyamides, polyvinyl chloride, polyethylene and polypropyrene, but polyesters and polyacrylonitrile are preferable.
  • the fibrous structures (woven, knitted, etc.) to be treated in the present invention mean staple fibers. continuous filaments, clothes, woven goods, knitted goods, non-woven clothes, battings, etc. which should contain more than 50% by weight of said hydrophobic textiles.
  • the application of the antistatic agent (complex compound) to the fibers or fibrous structures to be treated should be carried out by utilizing an organic solvent as the medium.
  • the concentration of the complex compound in the organic solvent solution should be in the range of 0.05 to by weight, preferably 0.2 to 3.0% by weight. Particularly, 0.3 to 1.0% by weight is most preferable. 1n case the antistatic agent concentration is less than 0.05% by weight, it is impossible to put a required amount of the complex compound on the textile material uniformly and, further, the production efficiency is lowered. On the other hand, when it exceeds 10% by weight, the uniform application of the antistatic agent becomes impossible owing to the increase of the solution viscosity and adhesive substances (socalled gum) will be adhered to the machinery and the textile fabrics, and product qualities and workability will be remarkably lowered.
  • gum solution viscosity and adhesive substances
  • alcohols to be used in the present invention methyl alcohol, ethyl alcohol, isopropyl alcohol, nbutyl alcohol, isoamyl alcohol, n-octyl alcohol, benzyl alcohol, o-chlorophenol, m-cresol, n-hexyl alcohol are exemplified. Ethyl alcohol and isopropyl alcohol are particularly suitable.
  • the amount of alcohols in the organic solvent solution should be in the range of 0.05 to by weight, preferably 0.2 to 6% by weight, most preferably 0.3 to 2% by weight.
  • the amount of alcohols should be at least 0.2 part by weight based on 1 part by weight of the antistatic agent (complex compound), but alcohols should be preferably used in the amount of 0.5 to 30 parts by weight, particularly 1 to 20 parts by weight to 1 part by weight of the complex compound.
  • the alcohol concentration is less than 0.05% by weight, the preparation of the antistatic agent solution will be difficult, while, in case it exceeds 20% by weight, deterioration of the product qualities, particularly discoloring of the product, will be caused.
  • the ratio of the amount of alcohols to the amount of the complex compound is less than 0.2/1, it will be difficult to dissolve the antistatic agent into the solvent solution.
  • organic solvents there can be used hydrocarbons such as n-hexane, cyclohexane, benzene, and toluene; halogenated hydrocarbons such as methyl chloride, methylenechloride, chloroform, carbontetrachloride, methylchloroform, dichloroethane, trichloroethylene, tetrachloroethane, perchloroethylene, dichlorobenzene and trichlorobenzene; ethers such as diethyl ether, methylethylether and ethylpropylether; ketones such as acetone and methylethylketone; esters such as ethyl acetate, methyl acetate and butyl acetate.
  • hydrocarbons such as n-hexane, cyclohexane, benzene, and toluene
  • halogenated hydrocarbons such as methyl chloride, methylenech
  • Halogenated hydrocarbons particularly methylchloroform, trichloroethylene and perchloroethylene are preferable.
  • the organic solvent should be used in a concentration of at least 70% by weight. but the concentration is preferably in the range of 92 to 99.6% by weight and more preferably in the range of 97 to 99.4% by weight. In case, the concentration of the organic solvent is less than 70% by weight, the alcohol concentration is so much increased that deterioration of product qualities,
  • the organic solvent solution of the antistatic agent i.e., complex compound
  • the organic solvent solution of the antistatic agent can he usually prepared. by swelling and dissolving the complex compound in a predetermined weight ratio of alcohols and then dissolving the obtained solution in the organic solvent.
  • the organic solvent solution of the complex compound thus obtained can be applied to a fibrous structure by any conventional method such as dipping, padding, coating and spraying.
  • padding and coating are suitable to woven fabrics
  • dipping, spraying and padding are suitable to knitted fabrics.
  • dipping and spraying are suitable.
  • the amount of said organic solvent solution to be applied to a fibrous structure depends on the concentration of said solution, the kinds of the material to be treated and the amount of the complex compound to be attached, but, for example, in the case of treating a woven fabric by a dipping method, the liquid is squeezed so as to make the solution to be 30 to by weight based on the fabric prior to the treatment by said organic solvent solution, the material to be treated should be preferably washed by said organic solvent, because such pretreatment will assist a uniform adhesion of the antistatic agent and increase the durability of the antistatic property.
  • the fibrous structure treated by the antistatic agent of the present invention can be used as a final product as it is, but also it can be further subjected to a resin finishing. Further, if the fibrous structure should be treated by a melamine resin, the melamine resin can be simultaneously used with the organic solvent solution of the present invention and, therefore, the omission of a particular resin finishing step is possible. In the case of the simultaneous use of a melamine resin, the durability of the antistatic effect can be increased without lowering the antistatic property.
  • the process of the present invention can be carried out at room temperature to obtain excellent effects, but, generally, the durability can be further increased by treating a fibrous structure under heat, after the organic solvent solution is applied to the fibrous structure and the solvent is removed therefrom.
  • the temperature of such heat treatment depends on the kinds of the fibrous strusture, but it is generally in the range of 60 to 210C and the treatment is carried out for 10 seconds to 20 minutes. Particularly, the range of 1 10 to 190C is preferable.
  • the heat treatment is carried out, for example, in a temperature of 150 to 200C for polyesters and in a temperature of 1 10 to C for polyacrylonitriles.
  • the fibrous structures to be treated according to the process of the present invention include yarn dyed goods, piece dyed goods and scoured and bleached goods. Further, the process can be applied to such secondary goods such as sweaters and -jumpers.
  • wetting or penetrating agents, stabilizing agent, etc. such as dialkylsulfosuccinates and alkyl phosphates can be preferably used to increase the solution stability of the organic solvent solution.
  • stabilizing agent such as dialkylsulfosuccinates and alkyl phosphates
  • softening agents and other kinds of antistatic agents can be used together, if
  • the fibers or fibrous structures thus obtained have an excellent antistatic effect, particularly, a remarkably 7 improved durability compared to conventionally available products and, therefore, the antistatic effect of the obtained fibers or fibrous structure is not lowered by washing. Further, in case a melmaine resin is used together, the durability of the antistatic effect is further increased, in addition to the resin finishing effect. Also, the color fastness to rubbing is not lowered and the occurence of water spots can be prevented.
  • EXAMPLE 1 Preparation of poly(Z-methacryloyloxyethyldimethylethylammonium ethosulfate) (hereinafter will be referred to as homopolymer A) in a liter four-neck flask provided with a Dimroth condenser, a thermometer, a dropping funnel and a blowing pipe, 1088 g (7 moles) of 2- dimethylaminoethylmethacrylate are charged. Then, 1078 g (7 moles) of diethyl sulfate are added thereto dropwise over about l.5 hours under countrol of generation of heat while temperature should be kept at below 50C.
  • the mixture is stirred at 50C for 30 minutes in air to complete the quaternization reaction. Thereafter, 8 1 9l gof water were added thereto to obtain the aqueous solution. After thorough replacement of air in the system with nitrogen gas, a solution of 17.4 g of potassium persulfate in 500 g ofwater is added to the mixture and the whole is allowed to react at 50C for 7 hours under stirring. The conversion was 96.3% and the viscosity of the obtained solution was 368 cp. aqueous solution at 30C).
  • EXAMPLE 2 continued further at a room temperature for additional 7 30-60 minutes to complete the reaction.
  • the precipitate is collected by filtration under reduced pressure, washed thorougly with water of 2 to 3 times as much as the precipitate several times and dried at 60C under reduced pressure overnight to obtain 39 g of a white solid product (yield 98.3%).
  • EXAMPLE 3 Preparation of a complex compound from homopolymer A and sodium trioxyethylene-dodecyl ether sulfate To I00 g of 20% aqueous homopolymer A solution, 100 g of sodium trioxyethylene dodecyl ether sulfate aqueous solution) are added dropwise with vigorous stirring. A precipitate is formed as soon as the addition starts. By the same procedures as in Example 2, 36 g of a pale yellowish brown solid product are obtained (yielded 96%).
  • EXAMPLE 4 Preparation of a complex compound from homopolymer A and sodium pentaoxyethylene-n-nonylphenyl ether mo'nophosphonate To I00 g of 20% aqueous homopolymer A solution. 137 g of sodium pentaoxyethylene-n-nonylphenyl ether monophosphonate (25% aqueous solution) are added dropwise with vigorous stirring. By the same procedures as in Example 2. 40 g ofa white solid product are obtained (yield 89.571).
  • EXAMPLE 5 Preparation of a complex compound from homopolymer A and sodium dioctylsuccinate sulfonate To l00 g of 20% aqueous homopolymer A solution. 1 l5 g of sodium dioctylsuccinate sulfonate (25% aqueous solution) are added dropwise with vigorous stirring. By the same procedures as in Example 2, 37 g of a light brown resinous solid product are obtained (yield 96.7%).
  • dioxane is distilled off under reduced pressure and the residue is dissolved in water to obtain 2340 g of l7.7% viscous, milky aqueous solution.
  • EXAMPLE 7 Preparation of a complex compound from the copolymer B obtained in Example 6 and sodium dioctylsuccinate sulfonate To g of l7.7'/r aqueous copolymer B solution. 76 g of 25% aqueous sodium dioctylsuccinate sulfonate solution are added dropwise with vigorous stirring at a room temperature. After completion of the addition, stirring is continued at a room temperature for further l hour to complete the precipitation and the resulting precipitate is gathered by filtration. The filtered precipitate is washed thoroughly with water and dried at 60C under reduced pressure overnight to obtain 27 g of white solid (yield 89.0%).
  • EXAMPLE 8 Preparation of a complex compound from copolymer B and sodium pentaoxyethylene-nmonylphenyl ether phosphate 5 To I g of l7.7% aqueous copolymer B solution, 91.5 g of 25% aqueous sodium pentaoxyethylene-nnonylphenyl ether phosphate solution are added dropwise with vigorous stirring at room temperature. By the same procedures as in Example 7, 33 g ofa light yellow solid product are obtained (yield 96.5%
  • EXAMPLE 13 Preparation of a complex compound from copolymer D prepared and quaternized in Example 1 l and sodium trioxyethylene dodecyl ether sulfate The reaction is carried out in the same manner in Example l2 and a solid product is obtained (yield EXAMPLE l4 Preparationof a complex compound from homopolymer A, sodium dioctyl succinate sulfonate and sodium lauryl sulfate In the same manner as in Example l2. sodium dioctyl succinate sulfonate and sodium lauryl sulfate (molar ratio 1:1 are reacted with homopolymer A to obtain a solid product (yield 100%).
  • EXAMPLE l5 Preparation of a complex compound of homopolymer A and sodium lauryloyl sarcosinate By reacting the starting materials in the same manner as in Example 12. a solid product is obtained (yield EXAMPLE 16 Preparation of a complex compound from homopolymer A, dodecyldimethylaminocarboxymethylbetaine (C H 'N (CH;,) 'CH COO') and sodium lauryl sulfate Homopolymer A is reacted with dodecyldimethylaminocarboxymethylbetaine and sodium lauryl sulfate (molar ratio lzl in the same manner as in Example 12 to obtain a solid product (yield 90% EXAMPLE 17 Preparation of a complex compound from homopolymer A, sodium trioxyethylene dodecyl ether sulfate and potassium n-octylsesquiphosphate Homopolymer A is reacted with sodium tri
  • EXAMPLE 18 A complex compound is obtained from homopoly- EXAMPLE I) A complex compound is obtained from homopolymer A and a compound of the following formula in the same manner as in Example l2:
  • compositions prepared in the above Examples were dissolved in perchloroethylene, trichloroethylene or methylchloroform to obtain a solution of 03% solid content.
  • An aliquot of 100 ml from the solution was placed in a beaker as the treating solution.
  • sample cloth pieces (20 X 20 cm) of each of fabrics of polyester (tropical: dyed in a dark color), nylon (tricot: not dyed) and acrylic (knitted fabric: not dyed) were immersed at a room temperature for 10 seconds. They were squeezed with a mangle to 120 wt.% liquid, air-dried and subjected to heating at 160C for 2 minutes.
  • the following tests of properties were carried out:
  • test pieces in round shape were cut from the treated cloth and allowed to stand at C under 40% RH for 24 hours.
  • Insulating resistance (surface electrical resistivity) of the test pieces was mea- Table sured with a resistance meter (manufactured by Horikawa Denki Col). Average of the five values was taken as the-antistatic property.
  • test pieces same as in the above item 1 were placed in a container of a laundry tester. which were then added with ml of 02% aqueous solution of a detergent (New Wonderful of Kao Soap Co.. Ltd.). Washing was done at 40C for 20 minutes. The same washing procedure was repeated ten times. Finally, the test pieces were washed twice each with l liter of warm water, dehydrated and dried and the antistatic property was measured in the same manner as in item 1.
  • a detergent New Wonderful of Kao Soap Co.. Ltd.
  • test pieces Five round test pieces (the same as in item I) were placed in the laundry tester and washed with 100 ml of a perchloroethylene solution containing 1% of a blend of anionic and non-ionic surfactants (Charge Soap P of Kao Soap Co., Ltd.) and 0.1% of water at 30C for 30 minutes. The test pieces were rinsed finally twice each with 100 ml of perchloroethylene.
  • a perchloroethylene solution containing 1% of a blend of anionic and non-ionic surfactants (Charge Soap P of Kao Soap Co., Ltd.) and 0.1% of water at 30C for 30 minutes.
  • the test pieces were rinsed finally twice each with 100 ml of perchloroethylene.
  • a drop of water was applied on the test piece through a burette and the time (in second) required for penetration was measured.
  • T, P and M in the following tables indicate trichloroethylene, perchloroethylene and methylchloroform, respectively.
  • Compounds of the referential examples did not dissolve in a solvent such as perchloroethylene or trichloroethylene to make a stable solution. Further. the compound of Referential Example l was far inferior in the color fastness to rubbing.
  • Polyester cloth (made of textured yarn and dyed in a dark color)
  • Solvent Antistatic property (insulating resistance 0) Color Hygro- Example for Before fastness scopicity Feelin No. treatlaundry After laundry (5 times) After laundry (10 times) to rubbing (second) 9 went Wet Dry Wet Dry Wet Dry 'r 8.9xl0 5.5xl0 3.6xl0 6.5xl0 6.8xl0 3 45 16 A o 3 P 7.5xl0 4.2xl0 2.6xl0 8.2xl0 4.1xl0 3-4 4-5 81 A o 4 P 1.3xl0 6.1xl0 2.2x1o 7.9xl0 4.4x10 3 4 54 Table 1 Continued Polyester cloth (made of textured yarn and dyed in a dark color) Solvent Antistatic property (insulating resistance Q) Dolor Hygrobxdwle 50: Before v fa'st-ness scopicity Feeling No.
  • test pieces in round shape were cut from the sample cloth and allowed to stand at 20C under 50% RH. Insulating resistances of the test pieces were measured with an electrometer (manufactured by Takeda Riken Co.. Ltd.). Average of the five values was taken.
  • the electrification voltage of the unfinished polymer of 2-methacryloyloityethylditnethylethylammonium ethosulfate and acrylon itrile (3 2 l) and sodium pentaoxyethylenenonyl phenyl ether sulfate was test piece was 6200 V and its insulating resistance was used.
  • a dyed cloth of polyester cashmere (warp l d/32 f/l weft 100 d/48 f/l was dipped in an organic solvent solution shown in Table 7 at a room temperature, nipped to a squeezing ratio of 160% o.w.f. and dried at 30 l20C. Test results were shown in Table 7.
  • the dyeing was made by using Dianix violet SRSE (manufactured by Mitsubishi Kasei Co.. Ltd.) as dye- Dissolved O Dissolved (swollen, A stuff and employing a with temperature and pressure Insoluble X dyeing tester (Colorpet l2 manufactured by Japan Table 5 Upper column:
  • the color fading in Table 7 was determined by measuring the absorbance of each organic solvent solution after the treatment at the maximum absorption wavespectrophotometer EPR-Z .(manufactured by Hitachi Seisakusho) and using a cell of I cm size.
  • An antistatic agent soluble in organic solvents, for imparting a-durable antistatic property to hydrophobic fibers and structures made'therefrom when applied in The solubility was determined by the same method as 5 an organic solvent system; said agent consisting essenin Example 23.
  • the complex compound a complex compound from poly(2-methacryloyloxyethyldimethylethylammonium sulfate) and N-methyl-N- (sodiumcarboxymethyl)-lauroamide was used.
  • the electrification voltage of the unfinished test cloth was 6800 V and its insulating resistance was more than 2 X 10' Q.
  • the complex compound a complex compound from poly(2-methacryloyloxyethylenedimethylethylammonium sulfate) and sodium trioxyethylene dodecyl ether monophosphate was used.
  • R is H or methyl. and R,-, is alkoxycarbonyl.
  • B counter anion of at least one surfactant selected from from the group consisting of anionic surfactants containing 2 to '8 ethylene oxide units. esterbonded sulfonates. alkzylamidocarboxylic acid salts and amphoteric surfactants of the carboxylic acid type.
  • alkyls of said trialkylammonium group which alkyls can be the same or different, are selected from the group consisting of methyland ethyl.
  • the antistatic agent as claimed in claim Lin which said surfactant is selected from the group consisting of sodium dioxyethylene dodecyl ether sulfate, sodium trioxyethylene dodecyl ether sulfate, sodium trioxyethylene-nnonylphenyl ether sulfate, sodium pentaoxyethylene dodecyl ether sulfate, sodium octaoxyethylene-n-nonylphenyl ether sulfate, sodium trioxyethylenedodecyl ether monophosphate, sodium trioxyethylene-n-nonylphenyl ether monophosphate. sodium trioxyethylenedodecyl ether carboxymethylate. sodium trioxyethylene-n-nonylphenyl ether carboxymethylate and sodium trioxyethylene-n-nonylphenyl ether B-carboxy ethylate.
  • said surfactant is selected from the group consisting of N-methyl-N-(sodium carboxymethyl) lauroamide and sodium N-lauroylglutamate.
  • said surfactant is selected from the group consisting of sodium 2-carboxyethyldodecylamine, sodium carboxymethyldodecylamine. di(sodium carboxymethyl)- dodecylamine and di(sodium 2-carboxymethoxyethyl dodecylamine.
  • the antistatic agent as claimed in claim 3, consisting of a complex compound selected from the group consisting of poly( Z-methacryloyloxyethyldimethylethyl ammonium trioxyethylene-n-nonyl phenyl ether sulfate). poly(2-methacryloyloxyethyldimethylethyl ammonium trioxyethylenedodecyl ether sulfate).
  • the antistatic agent as claimed in claim 6, consisting of a complex compound selected from the group consisting of poly( Z-methacryloyloxyethyldimethylethyl ammonium dodecyldimethylaminocarboxymethylbetaine) and poly(2-methacryloyloxyethyldimethylethyl ammonium Z-carboxyethoxyethyl-ldodecylim idazoline

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US284863A 1971-09-01 1972-08-30 Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same Expired - Lifetime US3864317A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551506A (en) * 1982-12-23 1985-11-05 The Procter & Gamble Company Cationic polymers having clay soil removal/anti-redeposition properties useful in detergent compositions
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4659802A (en) * 1982-12-23 1987-04-21 The Procter & Gamble Company Cationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
US4661288A (en) * 1982-12-23 1987-04-28 The Procter & Gamble Company Zwitterionic compounds having clay soil removal/anti/redeposition properties useful in detergent compositions
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US4751190A (en) * 1985-07-22 1988-06-14 Abbott Laboratories Fluorescence polarization immunoassay and reagents for use therein
US4761249A (en) * 1985-12-23 1988-08-02 Henkel Kommanditgesellschaft Auf Aktien Soil-collecting cleaning enhancers in aqueous surfactant laundering and cleaning solutions
US4773939A (en) * 1986-02-22 1988-09-27 Henkel Kommanditgesellschaft Auf Aktien Use of insoluble soil collectors for at least partial regeneration of laundering and cleaning solutions
US4863523A (en) * 1986-04-05 1989-09-05 Henkel Kommanditgesellschaft Auf Aktien Process for cleaning soiled solid molded articles
US4877687A (en) * 1986-09-16 1989-10-31 Mitsubishi Rayon Company, Ltd. Synthetic resin molded article having antistatic property
US5086106A (en) * 1986-09-08 1992-02-04 Mitsubishi Rayon Company Ltd. Methacrylic resin cast plate having excellent antistatic property
US6111056A (en) * 1997-09-15 2000-08-29 Basf Aktiengesellschaft Cyclic amine based polymers and process for their production
US6147183A (en) * 1997-09-15 2000-11-14 Basf Aktiengesellschaft Amphoteric amine based polymers having a net cationic charge and process for their production
EP1018346A3 (en) * 1999-01-07 2002-11-20 Terumo Kabushiki Kaisha Leucocyte filter and method for manufacturing same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6131431A (ja) * 1984-07-25 1986-02-13 Toray Ind Inc 超高分子量ナイロン６の製造法

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US2729577A (en) * 1953-02-27 1956-01-03 Du Pont Method of imparting antistatic properties to textile materials
US2741568A (en) * 1951-12-05 1956-04-10 Du Pont Water insoluble polymeric quaternary ammonium carboxylate salts and the treatment of textiles therewith
US2824861A (en) * 1955-05-19 1958-02-25 Arnold Hoffman & Co Inc Quaternary compounds
US3099636A (en) * 1960-05-17 1963-07-30 Du Pont Polymeric acid salts of alkylaminoethyl methacrylate
US3178397A (en) * 1961-09-25 1965-04-13 Ciba Ltd Water-soluble acrylic copolymers containing quaternary ammonium groups and including n-vinyl pyrrolidone type comonomer
US3361718A (en) * 1963-09-23 1968-01-02 Sanyo Chemical Industry Compan Antistatic agents for textile materials
US3661880A (en) * 1968-06-07 1972-05-09 Roehm Gmbh Process for preparing solid watersoluble cationic polymers

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US2723246A (en) * 1953-02-27 1955-11-08 Du Pont Antistatic compositions
US2723256A (en) * 1953-02-27 1955-11-08 Du Pont Polymeric alkyl sulfate quaternary ammonium salts of the acrylyloxyethylamine type

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741568A (en) * 1951-12-05 1956-04-10 Du Pont Water insoluble polymeric quaternary ammonium carboxylate salts and the treatment of textiles therewith
US2729577A (en) * 1953-02-27 1956-01-03 Du Pont Method of imparting antistatic properties to textile materials
US2824861A (en) * 1955-05-19 1958-02-25 Arnold Hoffman & Co Inc Quaternary compounds
US3099636A (en) * 1960-05-17 1963-07-30 Du Pont Polymeric acid salts of alkylaminoethyl methacrylate
US3178397A (en) * 1961-09-25 1965-04-13 Ciba Ltd Water-soluble acrylic copolymers containing quaternary ammonium groups and including n-vinyl pyrrolidone type comonomer
US3361718A (en) * 1963-09-23 1968-01-02 Sanyo Chemical Industry Compan Antistatic agents for textile materials
US3661880A (en) * 1968-06-07 1972-05-09 Roehm Gmbh Process for preparing solid watersoluble cationic polymers

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4551506A (en) * 1982-12-23 1985-11-05 The Procter & Gamble Company Cationic polymers having clay soil removal/anti-redeposition properties useful in detergent compositions
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4659802A (en) * 1982-12-23 1987-04-21 The Procter & Gamble Company Cationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
US4661288A (en) * 1982-12-23 1987-04-28 The Procter & Gamble Company Zwitterionic compounds having clay soil removal/anti/redeposition properties useful in detergent compositions
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US4751190A (en) * 1985-07-22 1988-06-14 Abbott Laboratories Fluorescence polarization immunoassay and reagents for use therein
US4761249A (en) * 1985-12-23 1988-08-02 Henkel Kommanditgesellschaft Auf Aktien Soil-collecting cleaning enhancers in aqueous surfactant laundering and cleaning solutions
US4773939A (en) * 1986-02-22 1988-09-27 Henkel Kommanditgesellschaft Auf Aktien Use of insoluble soil collectors for at least partial regeneration of laundering and cleaning solutions
US4863523A (en) * 1986-04-05 1989-09-05 Henkel Kommanditgesellschaft Auf Aktien Process for cleaning soiled solid molded articles
US5086106A (en) * 1986-09-08 1992-02-04 Mitsubishi Rayon Company Ltd. Methacrylic resin cast plate having excellent antistatic property
US4877687A (en) * 1986-09-16 1989-10-31 Mitsubishi Rayon Company, Ltd. Synthetic resin molded article having antistatic property
US6111056A (en) * 1997-09-15 2000-08-29 Basf Aktiengesellschaft Cyclic amine based polymers and process for their production
US6147183A (en) * 1997-09-15 2000-11-14 Basf Aktiengesellschaft Amphoteric amine based polymers having a net cationic charge and process for their production
EP1018346A3 (en) * 1999-01-07 2002-11-20 Terumo Kabushiki Kaisha Leucocyte filter and method for manufacturing same

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JPS4832782A (en)) 1973-05-02

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