WO2014156709A1 - Agent de traitement antistatique pour des fibres et procédé de production de fibres traitées de façon antistatique - Google Patents

Agent de traitement antistatique pour des fibres et procédé de production de fibres traitées de façon antistatique Download PDF

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WO2014156709A1
WO2014156709A1 PCT/JP2014/056835 JP2014056835W WO2014156709A1 WO 2014156709 A1 WO2014156709 A1 WO 2014156709A1 JP 2014056835 W JP2014056835 W JP 2014056835W WO 2014156709 A1 WO2014156709 A1 WO 2014156709A1
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antistatic
monomer
agent
fiber
fibers
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PCT/JP2014/056835
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English (en)
Japanese (ja)
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聖太郎 今尾
準 竹内
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松本油脂製薬株式会社
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Priority to JP2015508295A priority Critical patent/JP6271516B2/ja
Publication of WO2014156709A1 publication Critical patent/WO2014156709A1/fr

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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
    • 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
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • D06M15/27—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of alkylpolyalkylene glycol esters of unsaturated carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another

Definitions

  • the present invention relates to an antistatic processing agent for fibers used for imparting antistatic performance to a fiber material, and a method for producing an antistatic processed fiber using the processing agent.
  • Patent Document 1 discloses an antistatic agent using a quaternary ammonium salt having a long-chain alkyl ester group.
  • inorganic antistatic agents such as calcium chloride and guanidine hydrochloride may be used.
  • the antistatic agent and the inorganic antistatic agent using such a surfactant have a problem that the antistatic agent easily falls off by washing and the antistatic property is lowered.
  • the present invention has been made in order to solve the problem of washing durability in such conventional antistatic agents, and can impart excellent antistatic properties to the fiber material, and also has excellent washing durability. It aims at providing the manufacturing method of the antistatic processing fiber for fibers which has this, and the antistatic processing fiber using this processing agent.
  • the present inventors have found that the above problems can be solved if the antistatic processing agent for fibers contains a polymer obtained by polymerizing a specific polymerizable component and water. The inventors have found that this can be solved and have reached the present invention.
  • the antistatic processing agent for fibers of the present invention includes a polymer obtained by polymerizing a polymerizable component containing the monomer (A) represented by the following general formula (1) and water, and the polymerizable property.
  • the proportion of the monomer (A) in the component is 40 mol% or more.
  • R 1 is a hydrogen atom or a methyl group.
  • R 2 is an alkylene group having 1 to 3 carbon atoms.
  • R 3 , R 4 and R 5 are each independently a hydrogen atom or An alkyl group having 1 to 3 carbon atoms,
  • X ⁇ is a halide ion, a hydroxide ion, R a SO 3 ⁇ , R b OSO 3 — or R c COO —
  • R a , R b and R c is each independently an organic group.
  • the polymerizable component preferably further contains a monomer (B) represented by the following general formula (2).
  • R 6 is a hydrogen atom or a methyl group
  • AO is an oxyalkylene group having 2 to 3 carbon atoms
  • m is an integer of 1 to 100
  • R 7 is a hydrogen atom or carbon number. 1 to 3 alkoxy groups.
  • the proportion of the monomer (A) in the polymerizable component is preferably 40 to 99 mol%, and the proportion of the monomer (B) is preferably 1 to 60 mol%.
  • the molar ratio (A / B) between the monomer (A) and the monomer (B) is preferably 99/1 to 40/60.
  • M of the monomer (B) is preferably 4 to 90.
  • the manufacturing method of the antistatic processed fiber of this invention includes the process of providing said antistatic processing agent for fibers with respect to a fiber material. It is preferable that the manufacturing method of the antistatic processed fiber of this invention further includes the process of providing a crosslinking agent with respect to fiber material.
  • the cross-linking agent is preferably at least one selected from a diisocyanate cross-linking agent, a triisocyanate cross-linking agent, an aldehyde cross-linking agent, an oxazoline cross-linking agent, a carbodiimide cross-linking agent, and an ethyleneimine cross-linking agent.
  • the antistatic finishing agent for fibers of the present invention can impart excellent antistatic properties to the fiber material and has excellent washing durability. According to the method for producing an antistatic processed fiber of the present invention, an antistatic processed fiber having excellent antistatic properties and excellent washing durability can be obtained.
  • the antistatic finish for fibers of the present invention contains a polymer obtained by polymerizing a specific polymerizable component and water. Details will be described below.
  • the polymer used in the present invention (hereinafter sometimes simply referred to as a polymer) is obtained by polymerizing a polymerizable component containing a specific amount of the monomer (A) represented by the general formula (1). It is. By containing such a polymer as an essential component, excellent antistatic properties can be imparted to the fiber material, and the washing durability is excellent.
  • R 1 is a hydrogen atom or a methyl group.
  • R 2 is an alkylene group having 1 to 3 carbon atoms. The alkylene group preferably has 2 to 3 carbon atoms.
  • R 3 , R 4 and R 5 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group.
  • X ⁇ is a halide ion, hydroxide ion, R a SO 3 ⁇ , R b OSO 3 — or R c COO — .
  • Halide ions include Cl ⁇ , Br ⁇ , I ⁇ and the like, with Cl ⁇ and Br ⁇ being preferred, and Cl ⁇ being more preferred.
  • R a , R b and R c are each independently an organic group.
  • R a , R b and R c are preferably an alkyl group having 1 to 4 carbon atoms, an aryl group or an alkylaryl group, more preferably an alkyl group having 1 to 3 carbon atoms.
  • X ⁇ is particularly preferably a halide ion.
  • the proportion of the monomer (A) in the polymerizable component is 40 mol% or more, preferably 50 to 99 mol%, more preferably 60 to 98.5 mol%, and further preferably 70 to 98 mol%. When the proportion is less than 40 mol%, the washing durability becomes poor.
  • the polymerizable component preferably further contains the monomer (B) represented by the general formula (2). That is, the polymer is preferably a copolymer obtained by polymerizing a polymerizable component containing a specific amount of the monomer (A) and further containing the monomer (B).
  • the monomer (B) By using the monomer (B), excellent antistatic properties and washing durability can be imparted to the fiber material, and the temporal stability of the polymer in the processing agent is dramatically improved. .
  • R 6 is a hydrogen atom or a methyl group.
  • R 7 is a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms. The number of carbon atoms of the alkoxy group is preferably 1 to 2, and more preferably 1.
  • AO is an oxyalkylene group having 2 to 3 carbon atoms. 2 is preferable. 1 type (s) or 2 or more types may be sufficient as AO. In the case of two or more types, any of a block adduct, an alternating adduct, or a random adduct may be configured.
  • M is an integer of 1 to 100, preferably 4 to 90, more preferably 5 to 90, still more preferably 6 to 70, and particularly preferably 7 to 50.
  • m is less than 1, the antistatic performance may be poor.
  • m is more than 100, the temporal stability of the polymer becomes poor.
  • the proportion of the monomer (B) in the polymerizable component is 1 to 60 mol%, preferably 1 to 50 mol%, more preferably 1.5 to 40 mol%, still more preferably 2 to 30 mol%.
  • the proportion is more than 60 mol%, gelation may occur when preparing the polymer, and washing durability may be poor.
  • the total ratio of the monomer (A) and the monomer (B) in the polymerizable component is preferably 50 mol% or more, more preferably 60 mol% or more, and further preferably 70 mol% or more.
  • the molar ratio (A / B) of the monomer (A) to the monomer (B) is 99/1 to 40/60, preferably 99/1 to 60/40, and 99/1 to 70 / 30 is more preferable, and 99/1 to 80/20 is even more preferable. If the molar ratio is less than 40/60, washing durability may be poor. On the other hand, when the molar ratio exceeds 99/1, the temporal stability of the polymer may be poor.
  • the polymerizable component may contain other monomers other than the monomer (A) and monomer (B) as long as the effects of the present invention are not impaired. That is, the polymer contains a specific amount of the monomer (A), optionally contains the monomer (B), and further is a copolymer obtained by polymerizing a polymerizable component containing other monomers. It may be a polymer. Examples of other monomers include (meth) acrylic acid, (meth) acrylic acid ester monomers, and styrene monomers. In addition, in this application, (meth) acryl shall mean acryl and / or methacryl. Therefore, (meth) acrylic acid means acrylic acid and / or methacrylic acid, and (meth) acrylic acid ester monomer means an acrylic acid ester monomer and / or methacrylic acid ester single monomer. Means the body.
  • Examples of (meth) acrylate monomers include, for example, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, pentyl acrylate, hexyl acrylate, heptyl acrylate, octyl acrylate, and nonyl acrylate.
  • styrene monomer examples include styrene, vinyl toluene, ⁇ -methyl styrene, p-ethyl styrene, 2,4-dimethyl styrene, pn-butyl styrene, p-tert-butyl styrene, pn- Hexyl styrene, pn-octyl styrene, pn-nonyl styrene, pn-decyl styrene, pn-dodecyl styrene, ⁇ -methyl styrene, dimethyl styrene, n-methoxy styrene, p-phenyl styrene, p -Chlorstyrene, 3,4-dichlorostyrene and the like.
  • the proportion of the other monomers in the polymerizable component is preferably 1 to 50% by weight, more preferably 1.5 to 40% by weight, and even more preferably 2 to 30% by weight.
  • the polymer is obtained through a polymerization process for polymerizing the above polymerizable components.
  • water, a polymerization initiator, and the like are used in addition to the polymerizable component, but the polymerization method is not particularly limited as long as it is known. That is, methods such as emulsion polymerization, solution polymerization, suspension polymerization, and bulk polymerization can be used. Of these methods, solution polymerization using a radical polymerization initiator is preferred.
  • Examples of the solution used for the solution polymerization include alcohols such as methanol, ethanol and isopropanol, glycol ethers such as ethyl cellosolve and butyl cellosolve; propylene glycol ethers such as propylene glycol monomethyl ether; tetrahydrofuran, 1,4- Ethers such as dioxane; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; hydrocarbons such as toluene, xylene, hexane and heptane; esters such as ethyl acetate and butyl acetate; water and the like can be used.
  • alcohols such as methanol, ethanol and isopropanol
  • glycol ethers such as ethyl cellosolve and butyl cellosolve
  • propylene glycol ethers such as propylene glycol monomethyl ether
  • solvents may be used alone or in admixture of two or more depending on the type of monomer to be polymerized and the mixing ratio in the case of copolymerization.
  • the amount of the solvent used is 70 to 99 parts by weight, preferably 80 to 95 parts by weight, based on 100 parts by weight of the polymerizable component.
  • the radical polymerization initiator is not particularly limited, but azo compound catalysts such as azobisisobutyronitrile, azobisvaleronitrile, 2,2-azobis- (2-amidinopropane dihydrochloride), Peroxide catalysts such as oxide and hydrogen peroxide, and persulfate catalysts such as ammonium persulfate, sodium persulfate, and potassium persulfate can be used.
  • azo compound catalysts such as azobisisobutyronitrile, azobisvaleronitrile, 2,2-azobis- (2-amidinopropane dihydrochloride), Peroxide catalysts such as oxide and hydrogen peroxide, and persulfate catalysts such as ammonium persulfate, sodium persulfate, and potassium persulfate can be used.
  • the amount of the polymerization initiator used is 0.05 to 5 parts by weight, preferably 0.2 to 3 parts by weight, based on 100 parts by weight of the polymerizable component
  • the weight average molecular weight of the polymer is preferably 1000 to 80000, more preferably 3000 to 50000. When the weight average molecular weight is less than 1000, washing durability may be poor. On the other hand, when the weight average molecular weight exceeds 80,000, the solubility in water may decrease due to gelation or the like.
  • the weight average molecular weight was measured by gel permeation chromatography (GPC) using a calibration curve with a standard material polystyrene (Tosoh Corp.).
  • the polymerization step is not particularly limited, but can be performed at a polymerization temperature and a polymerization time adapted by a method such as emulsion polymerization, solution polymerization, suspension polymerization or bulk polymerization.
  • Examples of the polymerization step include solution polymerization using water as a solvent.
  • a polymer can be prepared by adding a polymerizable component and water to a four-necked flask and raising the temperature, and then dropping an aqueous solution containing an initiator.
  • the viscosity (20 ° C.) of the aqueous solution when the polymer concentration is 8% by weight is preferably 100 to 4000 mPa ⁇ s, more preferably 200 to 3000 mPa ⁇ s, and even more preferably 300 to 2000 mPa ⁇ s.
  • the antistatic processing agent for fibers of the present invention is used for imparting excellent antistatic properties to a fiber material.
  • the antistatic processing agent for fibers of the present invention contains the above polymer and water.
  • the antistatic processing agent of this invention contains the processing liquid which diluted this processing agent with water etc. when it provides to a fiber material not only the chemical
  • the proportion of the polymer in the antistatic processing agent of the present invention is preferably from 0.1 to 25% by weight, more preferably from 0.5 to 20% by weight, and even more preferably from 1 to 15% by weight.
  • the water used in the present invention may be pure water, distilled water, purified water, soft water, ion exchange water, or tap water.
  • the viscosity (20 ° C.) of the antistatic processing agent of the present invention is preferably 100 to 10000 mPa ⁇ s, more preferably 150 to 8000 mPa ⁇ s, and further preferably 200 to 5000 mPa ⁇ s.
  • the antistatic processing agent of the present invention may contain a cross-linking agent described later from the viewpoint of further exerting the effects of antistatic properties and washing durability.
  • the weight ratio of the polymer to the crosslinking agent is preferably 99/1 to 60/40, more preferably 95/5 to 65/35, and further preferably 90/10 to 70/30. preferable.
  • the antistatic processing agent of the present invention may contain other components other than those described above as long as the effects of the present invention are not impaired.
  • examples of other components include oil agents, nonionic surfactants, cationic surfactants, anionic surfactants, inorganic substances, preservatives, pH adjusters, antifoaming agents, solvents, fatty acids (salts), and the like.
  • the antistatic processing agent of the present invention may contain a processing agent that can be processed simultaneously with the antistatic processing as long as the effects of the present invention are not impaired.
  • Processing agents include discoloration inhibitors, discoloration inhibitors, insecticides, antifungal agents, acaricides, deodorants, antistatic agents, water and oil repellents, UV absorbers, flame retardants, antifouling agents, and deep colors. Examples thereof include an agent, a smoothing agent, a softening agent, and a water absorbing agent. A plurality of these drugs may be included. About each chemical
  • the method for preparing the antistatic processing agent of the present invention is not particularly limited, and known methods can be employed.
  • a polymer can be prepared as described above, and water and other components can be mixed and stirred as necessary.
  • the manufacturing method of the antistatic processing fiber of this invention includes the process (I) which provides the antistatic processing agent of this invention with respect to a fiber material. That is, the manufacturing method of this invention includes the process of providing an antistatic processing agent to a fiber material by post-processing. Post-processing means processing after the fiber material is manufactured. According to this production method, it is possible to obtain an antistatically processed fiber having excellent antistatic properties and excellent washing durability.
  • the fiber material may be either natural fiber or chemical fiber.
  • natural fibers include plant fibers such as cotton, cannabis, flax, palm, and rush; animal fibers such as wool, goat wool, mohair, cashmere, camel, and silk; and mineral fibers such as asbestos.
  • Examples of the chemical fiber include inorganic fibers such as rock fiber, metal fiber, graphite, silica, and titanate; regenerated cellulosic fibers such as rayon, cupra, viscose, polynosic, and purified cellulose fiber; melt-spun cellulose fiber; Protein fibers such as milk protein and soybean protein; Regenerated and semi-synthetic fibers such as regenerated silk and alginate fiber; Polyamide fiber, Polyester fiber, Cationic dyeable polyester fiber, Polyvinyl fiber, Polyacrylic alcohol fiber, Polyurethane fiber, Acrylic fiber, Examples thereof include synthetic fibers such as polyethylene fibers, polyvinylidene fibers, and polystyrene fibers. Two or more of these fibers may be combined (mixed spinning, mixed fiber, union, union, etc.).
  • Examples of the form of the fiber material include forms such as a woven fabric, a knitted fabric, a fabric, a thread shape, and a non-woven fabric.
  • Applications of the fiber material include objects that impart antistatic properties and washing resistance, such as underwear, work clothes, sports clothing, bedding, and covers.
  • the method for applying the antistatic finish to the fiber material is not particularly limited, and a known method can be employed. Among these, at least one method selected from the exhaust method, the pad dry method, the spray method, and the coating method is preferable from the viewpoint that the antistatic finish can be reliably fixed to the fiber material, and the pad dry method is preferable. Further preferred.
  • the exhaustion method is a method in which a diluted solution of a drug is used, conditions such as temperature, immersion time, number of times of liquid circulation, etc. are set, and the drug is selectively adsorbed on a fiber to be exhausted and adhered. Thereafter, washing is usually carried out, followed by centrifugal dehydration and drying.
  • the pad dry method is a method in which fibers are immersed in a drug solution for a short time and immediately attached by squeezing with a dehydrated mangle or the like. Then, drying is performed and curing is performed as necessary.
  • the spray method is a method in which fibers are placed on a conveyor at a constant speed and adhered by spraying a predetermined amount of a solution of the drug from the fiber. Then, drying is performed and curing is performed as necessary.
  • the coating method is a method in which a drug solution is usually applied by applying from one side with a mangle. Then, the excess drug is scraped off with a doctor, dried, and cured if necessary.
  • the temperature at which the antistatic finish of the present invention is applied to the fiber material is preferably 5 to 40 ° C.
  • the application temperature is lower than 5 ° C., it may be difficult to maintain the constant temperature, and thus it may not be possible to perform constant application to the fiber material.
  • the application temperature is higher than 40 ° C., the elution of dyes and the like contained in the fiber material may increase.
  • the weight ratio of the polymer in the antistatic processing agent (processing solution) when applied to the fiber material is preferably 0.01 to 25% by weight, more preferably 0.05 to 20% by weight, and more preferably 0.1 to 15% by weight is more preferred.
  • the predetermined weight ratio can be prepared by diluting with water or the like.
  • the amount of polymer applied to the fiber material is not particularly limited, but is preferably 0.01 to 20% by weight, more preferably 0.03 to 15% by weight, and 0.05 to 10% by weight based on the fiber material. Is more preferable. If it is less than 0.01% by weight, the fiber treated in the antistatic finish may not exhibit antistatic properties. If it exceeds 20% by weight, no further improvement in antistatic property and washing durability is observed, which may be economically disadvantageous.
  • the production method of the present invention preferably further includes a step (II) of imparting a crosslinking agent to the fiber material from the viewpoint of further exerting the effects of antistatic properties and washing durability.
  • the method for applying the crosslinking agent to the fiber material is the same as that for the antistatic processing agent.
  • Process (II) may be performed simultaneously with said process (I), and may be performed separately.
  • the antistatic processing agent (processing solution) further contains a crosslinking agent. From the viewpoint of productivity and economy, it is preferable to perform step (I) and step (II) simultaneously.
  • the weight ratio of the polymer to the crosslinking agent (polymer / crosslinking agent) in applying the crosslinking agent is preferably 99/1 to 60/40, more preferably 95/5 to 65/35, and 90/10. More preferred is ⁇ 70/30.
  • the crosslinking agent is not particularly limited as long as it crosslinks fibers, antistatic processing agents, or fibers and antistatic processing agents. What is marketed can be used as a crosslinking agent.
  • the crosslinking agent include at least one selected from diisocyanate crosslinking agents, triisocyanate crosslinking agents, aldehyde crosslinking agents, oxazoline crosslinking agents, carbodiimide crosslinking agents, and ethyleneimine crosslinking agents.
  • diisocyanate crosslinking agents such as 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4′-diphenylmethane isocyanate, isophorone diisocyanate, hexamethylene diisocyanate; Triisocyanate-based crosslinking agents obtained by reacting trimethylolpropane or glycerin with aldehyde-based crosslinking agents such as formaldehyde, acetaldehyde, glyoxal, malondialdehyde, succindialdehyde, glutardialdehyde, phthaldialdehyde; 2-iso Propenyl-oxazoline, 2-vinyl-oxazoline, 2-acryloyl-oxazoline, 2-styryl-oxazoline, 2,2'-o-phenylenebis (2-oxazoline), 2,2 ' m-phenylenebis (2-oxazoline), 2,2 ' m-
  • the crosslinking step may be performed simultaneously with the drying step after treating the antistatic processing agent on the fiber, or may be provided separately after the drying.
  • the crosslinking temperature is not particularly limited, but is preferably 100 ° C. or higher and more preferably 110 ° C. or higher in order to crosslink the antistatic processing agent on the fiber. If the crosslinking temperature is lower than 100 ° C., the crosslinking reaction may not proceed.
  • the manufacturing method of the present invention may include a process that can be processed simultaneously with the antistatic processing as long as the effects of the present invention are not impaired.
  • Processes that can be processed at the same time include discoloration inhibitors, discoloration inhibitors, insecticides, antifungal agents, acaricides, deodorants, antistatic agents, water and oil repellents, UV absorbers, flame retardants, and antifouling agents.
  • medical agent a well-known thing is employable.
  • Example 1 To a 1 liter four-necked flask equipped with a thermometer, stirrer, nitrogen flow, and dropping funnel, 79 g of polymerizable component dimethylaminopropylacrylamide methyl chloride quaternary salt and 246 g of soft water were added, and nitrogen flowed to 70 ° C. The temperature rose. While maintaining the liquid temperature at 70 ° C., 5.4 g of soft water containing 0.4 g of 2,2-azobis (2-methylpropionamidine) dihydrochloride as a polymerization initiator was dropped, and the mixture was heated and stirred for 1 hour to obtain a polymer. An aqueous solution containing was obtained.
  • the viscosity was measured by the following method. Thereafter, 669.6 g of soft water was added to obtain an antistatic processing agent a for fibers in which the proportion of the polymer in the processing agent was 8% by weight.
  • the stability of the obtained antistatic processing agent a for fibers was measured by the following method. The results are shown in Table 1.
  • Examples 2 to 13, Comparative Examples 1 to 4 Evaluation was performed in the same manner as in Example 1 except that the antistatic processing agents b to o were obtained by changing the polymerizable component, the polymerization initiator, water, and the ratio thereof shown in Tables 1 and 2. The results are shown in Tables 1 and 2.
  • Example 7 Evaluation was performed in the same manner as in Example 1 except that water was used instead of the processing solution as a blank (BL). The results are shown in Table 2.
  • Example 14 Crosslinking agent I and water were added to antistatic processing agent d obtained in Example 4 above, and the weight ratio of polymer to crosslinking agent (polymer / crosslinking agent) was 70/30.
  • a processing solution having a total weight ratio of the agent of 0.5% by weight was prepared.
  • Acrylic knit was immersed in this processing solution and squeezed with mangle. At this time, the adhesion amount of the processing solution to the fiber was 80% by weight. The adhesion amount was calculated in the same manner as described above.
  • the acrylic knit was dried with a pintender at 110 ° C. for 3 minutes and then cured at 180 ° C. for 2 minutes to obtain a test cloth (processed up) as an antistatic processed fiber.
  • the obtained test cloth was evaluated in the same manner as in Example 4 with respect to the friction withstand voltage, half-life and washing durability. The results are shown in Table 3.
  • crosslinking agents I to III in Tables 3 and 4 are as follows.
  • Crosslinking agent I Carbodilite V-02-L2 (Nisshinbo Chemical Co., Ltd.)
  • Crosslinking agent II Epocross WS-700 (manufactured by Nippon Shokubai Co., Ltd.)
  • Crosslinker III Carbodilite E-02 (Nisshinbo Chemical Co., Ltd.)
  • Example 15 to 25, comparison 8 to 10 Evaluation was performed in the same manner as in Example 14 except that the weight ratio of the antistatic processing agent, the crosslinking agent, and the polymer to the crosslinking agent shown in Tables 3 and 4 was changed. The results are shown in Tables 3 and 4.
  • Example 26 An antistatic processing agent for fibers was obtained in the same manner as in Example 1 except that the polymerizable component, polymerization initiator, water, and ratio thereof shown in Table 5 were changed. Next, the crosslinking agent I and water are added to the prepared processing agent, the weight ratio of the polymer and the crosslinking agent (polymer / crosslinking agent) is 80/20, and the total weight ratio of the polymer and the crosslinking agent is A processing solution of 0.5% by weight was prepared. Acrylic knit was immersed in this processing solution and squeezed with mangle. At this time, the adhesion amount of the processing solution to the fiber was 80% by weight. The adhesion amount was calculated in the same manner as described above.
  • the acrylic knit was dried with a pintender at 110 ° C. for 3 minutes and then cured at 180 ° C. for 2 minutes to obtain a test cloth (processed up) as an antistatic processed fiber.
  • the friction resistance voltage, half-life and washing durability of the obtained test cloth were evaluated in the same manner as in Example 1. The results are shown in Table 5.
  • Example 27 Evaluation was performed in the same manner as in Example 25 except that the polymerizable component, polymerization initiator, water, cross-linking agent, and ratio thereof shown in Table 5 were changed. The results are shown in Table 5.
  • the antistatic processing agent for fibers of the present invention can impart excellent antistatic properties to the fiber material as compared with the comparative example, and has excellent washing durability.
  • the monomer (B) is used in combination as the polymerizable component, so that it is understood that the stability of the processing agent is excellent.
  • Examples 14 to 28 are further excellent in antistatic property and washing durability because a crosslinking agent is used in combination.
  • the antistatic finish for fibers of the present invention can be suitably used for imparting antistatic properties to fiber materials.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention aborde le problème de durabilité de lavage d'agents antistatiques classiques, et le but de la présente invention est de proposer un agent de traitement antistatique pour des fibres, qui est apte à conférer une matière fibreuse d'excellentes propriétés antistatiques, tout en ayant une excellente durabilité de lavage. Un agent de traitement antistatique pour des fibres selon la présente invention contient de l'eau et un polymère qui est obtenu par polymérisation d'un constituant polymérisable qui contient un monomère (A) représenté par la formule générale (1). Le rapport du monomère (A) dans le constituant polymérisable est 40 % en mole ou plus. (Dans la formule (1), R1 représente un atome d'hydrogène ou un groupe méthyle ; R2 représente un groupe alkylène ayant 1-3 atomes de carbone ; chacun de R3, R4 et R5 représente indépendamment un atome d'hydrogène ou un groupe alkyle ayant 1-3 atomes de carbone ; X- représente un ion halogénure, un ion hydroxyde, RaSO3 -, RbOSO3 - ou RcCOO- ; et chacun parmi Ra, Rb et Rc représente indépendamment un groupe organique).
PCT/JP2014/056835 2013-03-28 2014-03-14 Agent de traitement antistatique pour des fibres et procédé de production de fibres traitées de façon antistatique WO2014156709A1 (fr)

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Cited By (2)

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JP2018100465A (ja) * 2016-12-21 2018-06-28 株式会社日本触媒 繊維処理剤
US11111340B2 (en) * 2018-06-26 2021-09-07 Kookmin University Industry Academy Cooperation Foundation Method for preparing biocompatible poly-γ-glutamic acid hydrogel by using ultraviolet rays

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JPS569474A (en) * 1979-07-03 1981-01-30 Teijin Ltd Antistatic process of polyamide synthetic fiber
JPS5870771A (ja) * 1981-10-23 1983-04-27 日本染化工業株式会社 合成繊維の耐久性帯電防止法
JPS63251409A (ja) * 1987-04-09 1988-10-18 Nippon Shokubai Kagaku Kogyo Co Ltd カチオン性オリゴマ−
JPH02269715A (ja) * 1989-04-11 1990-11-05 Sumitomo Chem Co Ltd カチオン性エマルジョン
JP2004501993A (ja) * 2000-06-27 2004-01-22 アトフィナ （ポリ）エトキシ化（メタ）アクリレートをべースにした感熱性水溶性コポリマーと、その製造方法
JP2013083023A (ja) * 2011-10-12 2013-05-09 Nicca Chemical Co Ltd 合成繊維用耐久吸水帯電防止剤及び機能性繊維製品

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JPS569474A (en) * 1979-07-03 1981-01-30 Teijin Ltd Antistatic process of polyamide synthetic fiber
JPS5870771A (ja) * 1981-10-23 1983-04-27 日本染化工業株式会社 合成繊維の耐久性帯電防止法
JPS63251409A (ja) * 1987-04-09 1988-10-18 Nippon Shokubai Kagaku Kogyo Co Ltd カチオン性オリゴマ−
JPH02269715A (ja) * 1989-04-11 1990-11-05 Sumitomo Chem Co Ltd カチオン性エマルジョン
JP2004501993A (ja) * 2000-06-27 2004-01-22 アトフィナ （ポリ）エトキシ化（メタ）アクリレートをべースにした感熱性水溶性コポリマーと、その製造方法
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018100465A (ja) * 2016-12-21 2018-06-28 株式会社日本触媒 繊維処理剤
JP7086451B2 (ja) 2016-12-21 2022-06-20 株式会社日本触媒 繊維処理剤
US11111340B2 (en) * 2018-06-26 2021-09-07 Kookmin University Industry Academy Cooperation Foundation Method for preparing biocompatible poly-γ-glutamic acid hydrogel by using ultraviolet rays

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