CN111247288A - Treating agent for synthetic fiber and synthetic fiber - Google Patents
Treating agent for synthetic fiber and synthetic fiber Download PDFInfo
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- CN111247288A CN111247288A CN201980005225.7A CN201980005225A CN111247288A CN 111247288 A CN111247288 A CN 111247288A CN 201980005225 A CN201980005225 A CN 201980005225A CN 111247288 A CN111247288 A CN 111247288A
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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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
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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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
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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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
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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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/01—Stain or soil resistance
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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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/35—Abrasion, pilling or fibrillation resistance
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2401/00—Physical properties
- D10B2401/14—Dyeability
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- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The agent for treating synthetic fibers of the present invention contains a smoothing agent, a nonionic surfactant, and an anionic surfactant. The anionic surfactant contains at least 1 phosphoric acid compound selected from the amine salts of phosphoric acid compounds A to C having a specific structural formula. The nonionic surfactant contains an ether ester compound having a mass average molecular weight of 3,000 to 30,000, and the ether ester compound is obtained by condensing at least one compound selected from the group consisting of an alkylene oxide adduct of castor oil and an alkylene oxide adduct of hardened castor oil with a monocarboxylic acid and a dicarboxylic acid.
Description
Technical Field
The present invention relates to a treatment agent for synthetic fibers which is effective in reducing tar stains and fuzz of synthetic fiber threads generated around a guide roll in a step of spinning synthetic fibers and has excellent dyeing uniformity even in water with high hardness, and to synthetic fibers to which the treatment agent is attached.
Background
In general, in the step of producing a synthetic fiber yarn, a treatment agent for a synthetic fiber containing a smoothing agent or the like is sometimes applied to the surface of a filamentous strand of a synthetic fiber in order to reduce friction and prevent fiber damage such as yarn breakage.
Conventionally, there have been known treatment agents for synthetic fibers disclosed in patent documents 1 to 4. Patent document 1 discloses a fiber-treating agent containing a potassium salt of a phosphate ester, ethylene oxide-added alkyl ether, ester, or the like, which is a starting material of a branched alcohol. Patent document 2 discloses a treatment agent for synthetic fibers, which contains a condensed phosphoric acid ester or an amine salt thereof, a nonionic surfactant, a smoothing component, and the like. Patent document 3 discloses a treatment agent for synthetic fibers containing a nonionic activator such as a specific hardened castor oil derivative, a dibasic ester compound, and the like. Patent document 4 discloses a treatment agent for synthetic fibers, which contains a sulfur-containing ester compound, a nonionic surfactant such as a specific hardened castor oil derivative, a specific ester, and the like.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. H01-298281
Patent document 2: japanese patent laid-open publication No. 2016-084566
Patent document 3: japanese laid-open patent publication No. 7-173768
Patent document 4: international publication No. 2015/186545
Disclosure of Invention
Problems to be solved by the invention
These conventional synthetic fiber treating agents are poor in the effect of effectively reducing tar stains and fuzz of synthetic fiber threads generated around a guide roll in a yarn-making step, and particularly have a problem of generation of dyeing stains in a hot melt adhesive dyeing step under water quality with high hardness.
The problems to be solved by the present invention are: a treating agent for synthetic fibers and synthetic fibers are provided which reduce tar stains and fuzz around a guide roll in a yarn-making step of synthetic fibers and have good dyeing uniformity even under high-hardness water.
Means for solving the problems
The present inventors have conducted studies to solve the above problems and found that a treating agent for synthetic fibers containing an amine salt of a phosphoric acid ester obtained from an aliphatic alcohol having a branched structure at a specific position as a raw material, a specific nonionic surfactant, and the like is particularly effective.
In order to achieve the above object, one aspect of the present invention provides a treatment agent for synthetic fibers, comprising: contains a smoothing agent, a nonionic surfactant, and an anionic surfactant; the anionic surfactant contains at least 1 kind of phosphoric acid compound selected from amine salt of phosphoric acid compound A shown in chemical formula 1, amine salt of phosphoric acid compound B shown in chemical formula 3, and amine salt of phosphoric acid compound C shown in chemical formula 4; the nonionic surfactant contains an ether ester compound having a mass average molecular weight of 3,000 to 30,000, and the ether ester compound is obtained by condensing at least one compound selected from the group consisting of an alkylene oxide adduct of castor oil and an alkylene oxide adduct of hardened castor oil with a monocarboxylic acid and a dicarboxylic acid.
[ chemical formula 1]
(in the chemical formula 1,
n: an integer of 2 to 4, or a combination thereof,
R1、R2: each being a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms,
R3: a hydrogen atom or a hydrocarbon group represented by the following chemical formula 2. )
[ chemical formula 2]
(in the chemical formula 2,
R4、R5: each of which is a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms. )
[ chemical formula 3]
[ chemical formula 4]
(in chemical formula 3 and chemical formula 4,
R6～R11: each of which is a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms. )
Preferably, the method comprises the following steps: the anionic surfactant further contains an organic sulfonic acid compound, and the mass ratio of the total content of the phosphoric acid compounds to the total content of the organic sulfonic acid compounds, i.e., the total mass of the phosphoric acid compounds/the total mass of the organic sulfonic acid compounds, is 70/30-10/90.
Preferably, the method comprises the following steps: the smoothing agent, the nonionic surfactant and the anionic surfactant are contained in an amount of 35 to 90 mass%, 1 to 60 mass% and 0.1 to 10 mass% based on the total of the contents of the smoothing agent, the nonionic surfactant and the anionic surfactant being 100 mass%.
In another aspect of the present invention, there is provided a synthetic fiber, wherein the synthetic fiber treatment agent is attached.
Effects of the invention
According to the present invention, tar stains and fuzz can be reduced, and further, excellent dyeing uniformity can be obtained even in high-hardness water.
Detailed Description
(embodiment 1)
First, embodiment 1 of a synthetic fiber treating agent (hereinafter referred to as treating agent) according to an embodiment of the present invention will be described. The treating agent of the present embodiment contains a smoothing agent, a specific nonionic surfactant, and a specific anionic surfactant. The anionic surfactant contains at least 1 phosphoric acid compound selected from the group consisting of an amine salt of a phosphoric acid compound A represented by the following chemical formula 5, an amine salt of a phosphoric acid compound B represented by the following chemical formula 7, and an amine salt of a phosphoric acid compound C represented by the chemical formula 8. These phosphoric acid compounds can be used alone in 1, also can be combined with more than 2.
[ chemical formula 5]
(in the chemical formula 5,
n: an integer of 2 to 4, or a combination thereof,
R1、R2: each being a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms,
R3: a hydrogen atom or a hydrocarbon group represented by the following chemical formula 6. )
[ chemical formula 6]
(in the chemical formula 6,
R4、R5: each of which is a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms. )
[ chemical formula 7]
[ chemical formula 8]
(in chemical formulas 7 and 8,
R6～R11: each of which is a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms. )
The smoothing agent used in the treatment agent of the present embodiment is not particularly limited, and examples thereof include (1) ester compounds formed from a monocarboxylic acid and a polyhydric alcohol such as 1, 4-butanediol dioleate, trimethylolpropane trilaurate, trimethylolpropane trioleate, glycerol trioleate, neopentyl tetraol tetranitrate, (2) ester compounds formed from a monocarboxylic acid and a polyhydric carboxylic acid such as diisocetyl mercaptan dipropionate, diisostearyl mercaptan dipropionate, dioleoyl mercaptan dipropionate, and polyoxyethylene lauryl adipate, (3) ester compounds formed from a monocarboxylic acid and a monohydric alcohol such as oleyl laurate, and oleyl oleate, and (4) natural oils and fats such as castor oil, palm oil, and rape seed white skein oil. These smoothing agents may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The nonionic surfactant used as the synthetic fiber-treating agent is not particularly limited, and examples thereof include (1) compounds obtained by adding an alkylene oxide having 2 to 4 carbon atoms to at least one member selected from the group consisting of organic acids, organic alcohols and organic amines, e.g., ether-type nonionic surfactants such as polyoxyethylene laurate, polyoxyethylene monooleate, polyoxyethylene laurate methyl ether, polyoxyethylene octyl ether, polyoxypropylene lauryl ether methyl ether, polyoxybutylene oleyl ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene nonylphenyl ether and polyoxyethylene lauryl amine ether, (2) polyol partial ester-type nonionic surfactants such as sorbitan monooleate, sorbitan trioleate and glycerol monolaurate, (3) polyethylene glycol dioleate, polyoxyethylene sorbitan monooleate, polyoxybutylene sorbitan trioleate, Polyoxypropylened castor oil, polyoxyethylenated hardened castor oil trioleate, polyoxyethylenated hardened castor oil trilaurate, ether ester compounds obtained by condensing an ethylene oxide adduct of hardened castor oil with fumaric acid, polyoxyalkylene polyol fatty acid ester type nonionic surfactants such as ether ester compounds obtained by condensing at least one member selected from the group consisting of an ethylene oxide adduct of castor oil and an ethylene oxide adduct of hardened castor oil with monocarboxylic acids and dicarboxylic acids, (4) alkylamide type nonionic surfactants such as diethanolamine monolaurate, and (5) polyoxyalkylene fatty acid amide type nonionic surfactants such as polyoxyethylene diethanolamine monooleamide. These nonionic surfactants may be used alone in 1 kind, or in combination with 2 or more kinds.
The nonionic surfactant used in the treatment agent of the present embodiment is an ether ester compound obtained by condensing at least one member selected from the group consisting of an alkylene oxide adduct of castor oil and an alkylene oxide adduct of hardened castor oil with a monocarboxylic acid and a dicarboxylic acid, and the ether ester compound has a mass average Molecular Weight (MW) of 3,000 to 30,000. Examples of the alkylene oxide used in the ether ester compound include ethylene oxide, propylene oxide, and butylene oxide. Examples of the monocarboxylic acid include dodecanoic acid, tetradecanoic acid, hexadecanoic acid, hexadecenoic acid, octadecanoic acid, isostearic acid, oleic acid, elaidic acid, octadecadienoic acid, octadecatrienoic acid, eicosanoic acid, eicosenoic acid, docosanoic acid, and docosadienoic acid. Examples of the dicarboxylic acid include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, fumaric acid, and maleic acid. Preferred ether ester compounds are listed as follows: a hardened castor oil 1 mol added with 20 mol of ethylene oxide (hereinafter, referred to as EO) crosslinked with adipic acid and end-esterified with oleic acid (MW10,000); castor oil 1 mole addition EO 25 mole is cross-linked with maleic acid, and the end is esterified with octadecanoic acid (MW5,000), etc.
As the mass average molecular weight, HLC-8320GPC, a high-speed gel permeation chromatography device manufactured by Tosoh corporation of Japan, can be used. The peak value can be calculated by injecting a sample concentration of 5mg/cc into each of separation columns TSK gelSuper H-2000, H-3000 and H-4000 manufactured by Tosoh corporation, Japan and measuring the peak value with a differential refractive index detector.
The anionic surfactant used in the treatment agent of the present embodiment contains at least 1 kind of phosphoric acid compound selected from the amine salt of the phosphoric acid compound a represented by the above chemical formula 5, the amine salt of the phosphoric acid compound B represented by the chemical formula 7, and the amine salt of the phosphoric acid compound C represented by the chemical formula 8, as described above.
In chemical formula 5, R1、R2Each of which is a saturated hydrocarbon group having 5 to 15 carbon atoms such as a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group and the like. Furthermore, R3Is a hydrogen atom or a hydrocarbon group represented by chemical formula 6. In addition, R in chemical formula 6, chemical formula 7, chemical formula 84、R5、R6、R7、R8、R9、R10、R11Are respectively the same as R illustrated in chemical formula 51、R2The same is true. The saturated hydrocarbon groups may be the same or different from each other.
Examples of the amine salt to be used as the counter ion of the phosphoric acid compound A, B, C include polyoxyalkylene alkylamine, monoalkanolamine, dialkanolamine, trialkanolamine and the like. Among these, preferable phosphoric acid compounds and amine salts include polyoxyethylene dodecylamine 2-decyl-1-decanol (having an alkoxy group constituting a starting material or a branched structure of each phosphoric acid compound, the same applies hereinafter), polyoxyethylene dodecylamine 2-hexyl-1-decanol phosphate (a counter ion, the same applies hereinafter), polyoxyethylene dodecylamine 2-octyl-1-dodecanol phosphate, polyoxyethylene octadecylamine, dibutyl ethanolamine 2-hexyl-1-decanol phosphate, octadecylamine 2-decyl-1-tetradecanol phosphate, and polyoxyethylene octadecylamine 2-octyl-1-dodecanol phosphate.
The phosphoric acid compound is a mixture of inorganic phosphoric acids, which is a multi-body phosphoric acid compound, a two-body phosphoric acid compound and a single phosphoric acid compound, synthesized by reacting an aliphatic alcohol with phosphorus pentoxide. The multimeric phosphoric acid compound contains an amine salt of the phosphoric acid compound A represented by the above chemical formula 5 of a condensed phosphoric acid ester. The dimeric phosphoric acid compound contains an amine salt of phosphoric acid compound B represented by the above chemical formula 7 in which 2 alkoxy groups having a branched structure are bonded to a phosphoric acid ester bond. The monomeric phosphoric acid compound comprises an amine salt of phosphoric acid compound C represented by the above chemical formula 8. The P-nucleus integration ratio of the multimeric phosphate compound represented by the following mathematical formula 1 is calculated from a P-nucleus NMR integrated value (pdoit) attributed to the multimeric phosphate compound, a P-nucleus NMR integrated value (P disome) attributed to the dimeric phosphate compound, and a P-nucleus NMR integrated value (P monomer) attributed to the monomeric phosphate compound, which are obtained by measuring the P-nucleus NMR of the treatment agent. The ratio of P nucleus integration of the polyphosphoric acid compound in the treatment agent of the present embodiment is not limited, and is preferably 10 to 50%.
[ mathematical formula 1]
The ratio (%) of P nuclear integral of the multimeric phosphate compound (pdomomer/(pdomomer + P dimer + P monomer)) X100
(in the mathematical formula 1, in the formula,
p multimer: p-nuclear NMR integral values assigned to multimeric phosphate compounds,
p two body: p-nuclear NMR integral values ascribed to the dimeric phosphoric acid compound,
p monomer: p-nuclear NMR integral values assigned to monomeric phosphate compounds. )
The anionic surfactant used in the treatment agent of the present embodiment contains at least 1 compound selected from the amine salt of the phosphoric acid compound a represented by chemical formula 5, the amine salt of the phosphoric acid compound B represented by chemical formula 7, and the amine salt of the phosphoric acid compound C represented by chemical formula 8, as described above. Further, it is preferable to contain an organic sulfonic acid compound as the anionic surfactant. The effect of the present invention, particularly the effect of inhibiting fluff and tar stains, can be further improved by blending the organic sulfonic acid compound. The mass ratio of the total content of each phosphate compound of the amine salt of the phosphate compound A, the amine salt of the phosphate compound B, and the amine salt of the phosphate compound C to the total content of the organic sulfonic acid compound, i.e., the total mass of the phosphate compound/the total mass of the organic sulfonic acid compound, is preferably 70/30 to 10/90. By limiting the content to this range, the effect of the present invention, particularly the tar stain-inhibiting effect, can be further improved.
The organic sulfonic acid compound is not particularly limited, and examples thereof include sodium 1-octylsulfonate, potassium 1-decylsulfonate, potassium 1-undecylsulfonate, sodium 1-dodecylsulfonate, sodium 1-tridecylsulfonate, sodium 1-tetradecylsulfonate, sodium 1-pentadecylsulfonate, potassium 1-hexadecylsulfonate, sodium 1-heptadecylsulfonate, sodium 1-octadecylsulfonate, sodium isooctylsulfonate, sodium isodecylsulfonate, potassium isoundecylsulfonate, sodium isododecylsulfonate, sodium isotridecylsulfonate, sodium isotetradecylsulfonate, sodium isotentadecylsulfonate, sodium isohexadecylsulfonate, sodium isoheptadecylsulfonate, sodium isooctadecylsulfonate, sodium alkyl (mixture of 13 to 17 carbon atoms) sulfonate, potassium diisobutylsulfonate, sodium dioctyl sulfosuccinate, potassium dodecylsulfonate, sodium dodecylbenzenesulfonate, potassium dodecyl, Sodium dinonyl succinate and the like. These compounds can be used alone in 1, also can be combined with more than 2.
In the treatment agent of the present embodiment, the content ratio of the smoothing agent, the nonionic surfactant, and the anionic surfactant is not particularly limited. When the total content of the smoothing agent, the nonionic surfactant and the anionic surfactant is 100% by mass, the content is preferably 35 to 90% by mass of the smoothing agent, 10 to 60% by mass of the nonionic surfactant and 0.1 to 10% by mass of the anionic surfactant. By setting in this range, the effect of the present invention can be further improved.
(embodiment 2)
Embodiment 2 of the synthetic fiber according to the present invention will be described. The synthetic fiber of the present embodiment is a synthetic fiber to which the treating agent of embodiment 1 is attached. The synthetic fibers are not particularly limited, and examples thereof include (1) polyester fibers such as polyethylene terephthalate, polypropylene terephthalate, and polylactic acid ester, (2) polyamide fibers such as nylon 6 and nylon 66, (3) polyacrylic fibers such as polyacrylic acid and modified acrylonitrile, and (4) polyolefin fibers such as polyethylene and polypropylene.
The ratio of the treating agent (without solvent) of embodiment 1 to be attached to the synthetic fibers is not particularly limited, and the treating agent of embodiment 1 is preferably attached to the synthetic fibers in a ratio of 0.1 to 3% by mass. The method of applying the treating agent of embodiment 1 can be a known method such as a drum-type oil feeding method, a guide-type oil feeding method using a metering pump, an immersion oil feeding method, or a spray oil feeding method. The form of the treatment agent of embodiment 1 when it adheres to the synthetic fibers can be provided in the form of, for example, an organic solvent solution, an aqueous solution, or the like.
According to the treatment agent for synthetic fibers and the synthetic fibers of the present embodiment, the following effects can be obtained.
(1) The present embodiment is a treatment agent for synthetic fibers, which contains a smoothing agent, a specific nonionic surfactant, and a specific anionic surfactant; the anionic surfactant is composed of an amine salt containing a phosphoric acid compound A, B, C represented by chemical formulas 5, 7, and 8, respectively. Therefore, particularly, tar stains generated around the guide roll in the step of producing a synthetic fiber can be suppressed. In addition, the fluff of the synthetic fiber yarn can be effectively reduced, and excellent process throughput can be exhibited. In addition, when the hardness of water used in the post-processing step, for example, the dyeing step is high, the occurrence of dyeing defects such as dyeing spots can be suppressed by making the separation of the dyeing liquid less likely to occur.
However, the above embodiment can be modified as follows.
The treatment agent of the present embodiment may further contain a component that is generally used in a treatment agent, such as an adhesive, an antioxidant, and an ultraviolet absorber, as a stabilizer or an antistatic agent for maintaining the quality of the treatment agent, within a range that does not impair the effects of the present invention.
Examples
The following examples and the like are given to more specifically explain the constitution and effects of the present invention, but the present invention is not limited to these examples. In the following description of examples and comparative examples, parts represent parts by mass, and% represents% by mass.
Test group 1 (Synthesis of alkyl phosphate Compound)
Synthesis of phosphoric acid Compound (P-1)
Placing 2-decyl-1-tetradecanol into a reaction vessel, dehydrating at 120 deg.C and under 0.05MPa for 2 hr, returning to normal pressure, adding phosphorus pentoxide at 60 + -5 deg.C for 1 hr, and stirring. After aging at 80 ℃ for 3 hours, polyoxyethylene (4 mol) dodecylamine was added dropwise at 50 ℃ to neutralize the reaction solution, thereby preparing a phosphoric acid compound (P-1).
Calculation of P Nuclear integration ratio of phosphoric acid Compound (P-1)
For phosphoric acid compound (P-1)31As a result of P-NMR calculation of the P nucleus integration ratio, the multimeric phosphoric acid compound represented by chemical formula 5 was 36.2%, the dimeric phosphoric acid compound represented by chemical formula 7 was 32.3%, and the monomeric phosphoric acid compound represented by chemical formula 8 was 31.5%.
P kernel integration ratio is used31The measurement value of P-NMR (product name of MERCURY plusNMRSpectrometer System, 300MHz, manufactured by VALIAN) was calculated from the above equation 1.
Preparation of phosphoric acid Compounds (P-2 to P-4 and rP-1 to rP-6)
Other phosphoric acid compounds (P-2 to P-4 and rP-1 to rP-6) were prepared in the same manner as the phosphoric acid compound (P-1).
Preparation of phosphoric acid Compound (P-5)
2-decyl-1-tetradecanol and ion-exchanged water are placed in a reaction vessel, and phosphorus pentoxide is added and stirred at 60 + -5 ℃ over 1 hour. After aging at 80 ℃ for 3 hours, ion-exchanged water was added, hydrolysis was carried out at 100 ℃ for 2 hours, and octadecylamine was added dropwise at 50 ℃ to neutralize the mixture, thereby preparing a phosphoric acid compound (P-5). For phosphoric acid compound (P-5)31As a result of P-NMR calculation of the P nucleus integration ratio, the multimeric phosphoric acid compound represented by chemical formula 5 was 0%, the dimeric phosphoric acid compound represented by chemical formula 7 was 37.9%, and the monomeric phosphoric acid compound represented by chemical formula 8 was 62.1%. The contents of the phosphoric acid compounds prepared above are shown in table 1.
Preparation of phosphoric acid Compound (P-6)
The phosphoric acid compound (P-6) having each substituent shown in Table 1 was prepared in the same manner as the phosphoric acid compound (P-5).
[ Table 1]
The symbols in table 1 indicate:
x-1: polyoxyethylene (4 mol) dodecylamine
X-2: polyoxyethylene (10 mol) dodecylamine
X-3: polyoxyethylene (10 mol) octadecylamine
X-4: dibutylethanolamine
X-5: octadecamine
X-6: polyoxyethylene (2 mol) octadecylamine
X-7: polyoxyethylene (4 mol) octadecylamine
X-8: polyoxyethylene (2 mol) dodecylamine
X-9: triethanolamine
X-10: dodecyl amine
X-11: sodium salt
X-12: potassium salt
P-1: 2-decyl-1-tetradecanol phosphate polyoxyethylene (4 mol) dodecylamine salt
P-2: 2-hexyl-1-decanol phosphate polyoxyethylene (10 mol) dodecylamine salt
P-3: polyoxyethylene (10 mol) octadecylamine salt of 2-octyl-1-dodecanol phosphate
P-4: 2-hexyl-1-decanol phosphate dibutyl ethanolamine salt
P-5: octadecyl 2-decyl-1-tetradecanol phosphate
P-6: 2-octyl-1-dodecanol phosphate polyoxyethylene (2 mol) octadecylamine salt
rP-1: polyoxyethylene (4 mol) octadecylamine salt of 2-ethyl-1-hexanol phosphate
rP-2: oleyl alcohol phosphate polyoxyethylene (2 mol) dodecylamine salt
rP-3: 14-methyl-1-pentadecanol phosphate triethanolamine salt
rP-4: 5-Hexadecanol phosphate dodecaamine salt
rP-5: 2-decyl-1-tetradecanol phosphate sodium salt
rP-6: 2-hexyl-1-decanol phosphate potassium salt
＊ 1 Hydrocarbon group of chemical formula 6
Test group 2 (Synthesis of Ether ester Compound as nonionic surfactant)
Synthesis of Ether ester Compound (N-1)
An ether ester compound (N-1) is obtained by esterifying a hardened castor oil compound having EO added thereto in an amount of 1 mol with adipic acid under normal conditions, and then further esterifying the resultant product with oleic acid.
Synthesis of Ether ester Compounds (N-2 and rN-1 to rN-5)
Ether ester compounds (N-2 and rN-1 to rN-5) were synthesized in the same manner as in the synthesis of ether ester compound (N-1). The compounds used in the examples and comparative examples are shown in tables 2 and 3.
Test group 3 (preparation of treating agent for synthetic fiber)
Preparation of treating agent for synthetic fiber (example 1)
Trimethylolpropane trilaurate (L-1)40 parts, glycerol trioleate (L-2)12 parts, hardened castor oil (EO-1) 1 mol added as a non-ionic surfactant, which is crosslinked with adipic acid and esterified with oleic acid at the end, compound (rN-1)10 parts, hardened castor oil (EO-20 mol added) esterified with dodecanoic acid 3 mol (rN-1)10 parts, hardened castor oil (EO-3) 10 parts, hardened castor oil (EO-15 mol added 1 mol), polyoxyethylene (EO15 mol) monooleate (rN-4)16 parts, polyoxyethylene (EO15 mol) (4 mol) dodecylamine salt (P-1)0.5 part of 2-decyl-1-tetradecanol phosphate (4 mol), sodium alkylsulfonate (a mixture of 13-17 carbon atoms) (S-1)1.5 parts, are uniformly mixed in proportions, the treating agent for synthetic fiber of example 1 was prepared.
Preparation of a treating agent for synthetic fibers (example 2)
Prepared in the same manner as the synthetic fiber treating agent of example 1. In addition to the raw materials shown in table 2, 1,3, 5-tris (4-t-butyl-3-hydroxy-2, 6-dimethylbenzyl) isocyanurate was added as an antioxidant in an amount of 0.5 part per 100 parts of a treating agent composed of a smoothing agent, a nonionic surfactant and an anionic surfactant.
Preparation of treating agents for synthetic fibers (examples 3 to 9 and 13, reference examples 10 to 12, and comparative examples 1 to 7)
The treating agents for synthetic fibers of examples 3 to 9 and 13, reference examples 10 to 12, and comparative examples 1 to 7 were prepared in the same manner as the preparation of the treating agent for synthetic fibers of example 1. The kinds and amounts of the compounds used are shown in tables 2 and 3.
[ Table 2]
[ Table 3]
The symbols in tables 2 and 3 represent:
l-1: trimethylol propane trilaurate
L-2: glycerol trioleate
L-3: oleyl oleate
N-1: hardened castor oil 1 mol EO 20 mol crosslinked by adipic acid and end-esterified by oleic acid (MW10,000)
N-2: castor oil compound with 1 mol addition EO 25 mol cross-linked by maleic acid and end esterified by octadecanoic acid (MW5,000)
rN-1: hardened castor oil 1 mol addition EO 20 mol compound esterified with dodecanoic acid 3 mol
rN-2: hardened castor oil 1 mol EO 30 mol crosslinked with fumaric acid (MW5000)
rN-3: hardened castor oil compound with 1 mol of EO15 mol
rN-4: polyoxyethylene (EO15 mol) monooleate
rN-5: polyethylene glycol (EO15 mol) dioleate
S-1: sodium alkylsulfonate (mixture of C13-17)
S-2: sodium dodecyl sulfate
＊ 2 Total mass of phosphoric acid compounds represented by chemical formulas 5, 7 and 8/Total mass of sulfonic acid compounds
Test group 4 (evaluation of synthetic fiber treatment agent)
Evaluation of pile
Each treatment agent prepared in test group 3 was uniformly diluted with ion-exchanged water or an organic solvent as appropriate to be a 15% solution. After drying pellets of polyethylene terephthalate by a conventional method, melt spinning was performed using an extruder, and the 15% solution was deposited on a line diameter strand discharged from a nozzle and cooled to solidify, with the amount of the 15% solution added being set to 0.6 mass% as a nonvolatile component by a drum-type oil feeding method. Then, the yarn was collected by a guide, stretched by a stretching roll at 245 ℃ and a relax roll so that the total draw ratio was 5.8 times, and 1100dtex 96 film drawn yarn was wound into 10kg flat package yarn.
In this spinning step, the number of naps per 1 hour was measured by a nap counting device (manufactured by Toshiki engineering Co., Ltd.) before the yarn was wound into a flat package, and evaluated by the following criteria.
Evaluation criteria of pile
◎ determination of the number of piles to be 0
○ that the number of measured piles is 2 or less (0 is not included in the list)
X: the number of measured fluff is more than 3
Evaluation of Heat-resistant Tar
Regarding the heat resistance of the treatment agent, in the above spinning step, the stain (tar) on the guide roller after 48 hours of spinning was evaluated in the following manner.
Evaluation criteria for Heat resistant Tar
◎ little stain (tar)
○ confirmation of a little spot of stain (tar)
X: confirmation of stain (Tar)
Evaluation of staining solution stability
1G of a dye for polyester (a mixture of Dianix Red S-4G 0.34G, Dianix Yellow S-6G 0.33G, and Dianix S-2G 0.33G) was put into 100mL of hard water (hardness 400mg/L) and stirred until uniform, thereby preparing a dye dispersion. 1.5g of nonvolatile matter of the treating agent was added to the dye dispersion, and the mixture was stirred until homogeneous, and then left at 50 ℃ for 3 days to observe the formation of aggregates.
Evaluation criteria for stability of staining solution
◎ No agglomerates were observed
○ A little bit of aggregate was observed
X: agglomerates were observed
As is clear from the results in tables 2 and 3, the effect of the present invention can reduce tar stains and fuzz around the guide roll in the step of spinning synthetic fibers, and can solve the problem of poor dyeing caused by high-hardness water in the subsequent processing step.
Claims (4)
1. A synthetic fiber treatment agent comprising a smoothing agent, a nonionic surfactant, and an anionic surfactant, characterized in that:
the anionic surfactant comprises at least 1 kind of phosphate compound selected from amine salt of phosphate compound A shown in chemical formula 1, amine salt of phosphate compound B shown in chemical formula 3, and amine salt of phosphate compound C shown in chemical formula 4,
the nonionic surfactant contains an ether ester compound having a mass average molecular weight of 3,000 to 30,000, the ether ester compound is obtained by condensing at least one compound selected from the group consisting of an alkylene oxide adduct of castor oil and an alkylene oxide adduct of hardened castor oil with a monocarboxylic acid and a dicarboxylic acid,
[ chemical formula 1]
In the chemical formula 1, the metal oxide is represented by,
n: an integer of 2 to 4, or a combination thereof,
R1、R2: each being a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms,
R3: a hydrogen atom or a hydrocarbon group represented by the following chemical formula 2,
[ chemical formula 2]
In the chemical formula 2, the first and second,
R4、R5: each being a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms,
[ chemical formula 3]
[ chemical formula 4]
In chemical formula 3 and chemical formula 4,
R6～R11: each of which is a saturated aliphatic hydrocarbon group having 5 to 15 carbon atoms.
2. The agent for treating synthetic fibers according to claim 1, wherein,
the anionic surfactant further contains an organic sulfonic acid compound, and the mass ratio of the total content of the phosphoric acid compounds to the total content of the organic sulfonic acid compounds, i.e., the total mass of the phosphoric acid compounds/the total mass of the organic sulfonic acid compounds, is 70/30 to 10/90.
3. The agent for treating synthetic fibers according to claim 1 or 2, wherein,
the smoothing agent, the nonionic surfactant and the anionic surfactant are contained in an amount of 35 to 90 mass%, 1 to 60 mass% and 0.1 to 10 mass% based on the total of the contents of the smoothing agent, the nonionic surfactant and the anionic surfactant being 100 mass%.
4. A synthetic fiber to which the synthetic fiber treatment agent according to any one of claims 1 to 3 is attached.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| JP2018078238A JP6405068B1 (en) | 2018-04-16 | 2018-04-16 | Synthetic fiber treatment agent and synthetic fiber |
| JP2018-078238 | 2018-04-16 | ||
| JP2018-142433 | 2018-07-30 | ||
| JP2018142433A JP6405072B1 (en) | 2018-07-30 | 2018-07-30 | Synthetic fiber treatment agent and synthetic fiber |
| PCT/JP2019/006534 WO2019202844A1 (en) | 2018-04-16 | 2019-02-21 | Treatment agent for synthetic fibers, and synthetic fibers |
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| KR (1) | KR102355502B1 (en) |
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| CN113950549A (en) * | 2020-06-11 | 2022-01-18 | 竹本油脂株式会社 | Aqueous liquid of treating agent for synthetic fiber and synthetic fiber |
| CN115584630A (en) * | 2021-07-06 | 2023-01-10 | 竹本油脂株式会社 | Treating agent for synthetic fiber and synthetic fiber |
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| KR102460481B1 (en) * | 2020-06-11 | 2022-10-28 | 다케모토 유시 가부시키 가이샤 | Treatment agents for synthetic fibers and synthetic fibers |
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- 2019-02-21 WO PCT/JP2019/006534 patent/WO2019202844A1/en active Application Filing
- 2019-02-21 CN CN201980005225.7A patent/CN111247288B/en active Active
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| JPH06346368A (en) * | 1993-06-03 | 1994-12-20 | Toray Ind Inc | Treating agent for synthetic fiber |
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| TWI679325B (en) | 2019-12-11 |
| KR20200058522A (en) | 2020-05-27 |
| TW201943922A (en) | 2019-11-16 |
| CN111247288B (en) | 2021-01-22 |
| KR102355502B1 (en) | 2022-02-08 |
| WO2019202844A1 (en) | 2019-10-24 |
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