CN112779773A - Treating agent for synthetic fiber and use thereof - Google Patents

Treating agent for synthetic fiber and use thereof Download PDF

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Publication number
CN112779773A
CN112779773A CN202110042703.0A CN202110042703A CN112779773A CN 112779773 A CN112779773 A CN 112779773A CN 202110042703 A CN202110042703 A CN 202110042703A CN 112779773 A CN112779773 A CN 112779773A
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treating agent
acid
group
compound
organic
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CN112779773B (en
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氏野郁也
奥泽政巨
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Matsumoto Yushi Seiyaku Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • 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
    • 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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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The invention aims to provide a treating agent for synthetic fibers, which is used in the production of synthetic fibers, can reduce roll contamination and has excellent thermal endurance. The agent for treating synthetic fibers of the present invention comprises a smoothing component (A), an organic sulfonic acid compound (B1) represented by the general formula (1), an organic sulfonic acid compound (B2) represented by the general formula (2), and an organic phosphate compound (C),and the organic phosphate compound (C) accounts for 0.05-10 wt% of the nonvolatile components of the treating agent, and phosphate ions (PO 4) detected from the nonvolatile components of the treating agent by ion chromatography3‑) The weight ratio of (B) is 300ppm or less.

Description

Treating agent for synthetic fiber and use thereof
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application is a divisional application entitled "synthetic fiber treating agent and use thereof" filed in 2017, 05, month 02 and entered the chinese country, national application No. 201580059616.9.
Technical Field
The present invention relates to a treatment agent for synthetic fibers and use thereof. More specifically, the present invention relates to a treatment agent for synthetic fibers used in the production of synthetic fibers, a method for producing synthetic fiber filament yarns using the treatment agent, and a fiber structure containing the synthetic fiber filament yarns.
Background
Conventionally, fibers treated with a fiber finish are temporarily crimped and used in a drawing process, but recently, a method of shortening the process and using an oiling (oiling) yarn directly in the drawing process has been adopted.
In this method, a large amount of fiber loss is caused when a problem such as yarn breakage occurs in the drawing step, and therefore, it is necessary to avoid the problem in the drawing step as much as possible. The main cause of the problem is fiber damage such as yarn breakage, and in order to prevent this problem, a synthetic fiber treatment agent having excellent lubricity and heat resistance is required.
Further, improvements in physical properties such as high strength and low shrinkage of the fiber, and improvements in productivity such as multi-end and high speed in production have been achieved, but problems such as increased fuzz and yarn breakage due to roll contamination, which have not been a problem until now, have been raised. Therefore, in order to keep the roller in a clean state, the cleaning interval of the roller is shortened, the number of times of cleaning is increased, and it is pointed out that productivity is lowered.
In order to solve this problem, patent document 1 proposes a treatment agent for synthetic fibers, which uses a phosphate anionic surfactant and a sulfonate anionic surfactant in combination. However, the use of the treatment agent in a roll form has the following disadvantages: heat resistance and lubricity are insufficient, oil components and the like after thermal degradation accumulate in the drawing roll, friction increases with time, yarn breakage occurs in the drawing step, and fiber quality is degraded.
Further, patent document 1 proposes a treatment agent in which a specific ester and an antioxidant are used in combination in the above anionic surfactant. However, even with such a treating agent, heat resistance satisfying strict yarn-making conditions cannot be obtained.
Further, patent document 1 proposes a treatment agent in which a specific ester and an antioxidant are used in combination in the above anionic surfactant. However, even with such a treating agent, heat resistance satisfying strict yarn-making conditions cannot be obtained.
In order to solve the above problems, patent document 2 proposes a treating agent obtained by using a polyol ester, a thioether group-containing carboxylic acid ester with an alcohol, a secondary sulfonate, an alkyl phosphate, and a hindered phenol antioxidant in combination. However, even when the treating agent is used, fluff and yarn breakage due to roll contamination, which have not been a problem until now, due to improvement in productivity such as high strength, low shrinkage and high speed, cannot be improved. Further, when the antioxidant described in patent document 2 is used, there is a disadvantage that the fibers gradually change color during storage.
Therefore, a treatment agent having excellent heat resistance is desired which can suppress the decrease in productivity due to the reduction in the cleaning interval of the roller and the increase in the number of times of cleaning.
Prior art documents
Patent document
Patent document 1: japanese laid-open patent publication No. 59-211680
Patent document 2: japanese laid-open patent publication No. 8-120563
Disclosure of Invention
Technical problem to be solved by the invention
The invention aims to provide a synthetic fiber treating agent which is used in the production of synthetic fibers, can reduce roll contamination and has excellent heat resistance, a method for producing synthetic fiber filament yarns using the treating agent, and a fiber structure comprising the synthetic fiber filament yarns obtained by the production method.
Means for solving the problems
The present inventors have conducted intensive studies and, as a result, have found that the problems of the present invention can be solved by using a combination of a smoothing component and specific 2 kinds of organic sulfonic acid compounds, and have completed the present invention.
That is, the synthetic fiber-treating agent of the present invention contains a smoothing component (a), an organic sulfonic acid compound (B1) represented by the following general formula (1), and an organic sulfonic acid compound (B2) represented by the following general formula (2).
[ solution 1]
Figure BDA0002896528430000031
(in the formula (1), a and b are integers of 0 or more and satisfy a + b ═ 5-17. M is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.)
[ solution 2]
Figure BDA0002896528430000032
(in the formula (2), c, d, and e are integers of 0 or more and satisfy the requirement that c + d + e is an integer of 4 to 16. M is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.)
Preferably, the treatment agent of the present invention further comprises an organic phosphate compound (C), wherein the organic phosphate compound (C) is contained in an amount of 0.05 to 10% by weight based on the nonvolatile component of the treatment agent, and phosphate ions (PO) detected from the nonvolatile component of the treatment agent by ion chromatography4 3-) The weight ratio of (B) is 300ppm or less.
Preferably, the smoothing component (a) accounts for 20 to 70 wt% of the nonvolatile component of the treating agent.
Preferably, the weight ratio (B1/B2) of the organic sulfonic acid compound (B1) to the organic sulfonic acid compound (B2) is 50/50 to 99/1.
Preferably, the total weight ratio of the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2) in the nonvolatile component of the treating agent is 0.1 to 12 wt%.
Preferably, the organic phosphate compound (C) is at least 1 selected from a compound represented by the following general formula (4) and a compound represented by the following general formula (5).
[ solution 3]
Figure BDA0002896528430000041
(in the formula (4), R3Is a hydrocarbon group having 6 to 24 carbon atoms. A. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15. n is an integer of 1 to 2. M1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. )
[ solution 4]
Figure BDA0002896528430000051
(in the formula (5), R3Is a hydrocarbon group having 6 to 24 carbon atoms. A. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15. M1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. Q1Is M1Or R3O(A1O)m. Y is 1 or 2. )
Preferably, the treating agent of the present invention further contains a nonionic surfactant (D).
The synthetic filament yarn of the present invention is obtained by applying the above-mentioned treating agent to a raw synthetic filament yarn.
The method for producing a synthetic fiber filament yarn of the present invention comprises the step of applying the above-described treating agent to a raw synthetic fiber filament yarn.
The fiber structure of the present invention is a fiber structure comprising the synthetic fiber filament yarn and/or the synthetic fiber filament yarn obtained by the above production method.
Effects of the invention
When the treatment agent for synthetic fibers of the present invention is used, roll contamination during the production of synthetic fibers can be reduced, and the treatment agent for synthetic fibers is excellent in heat resistance. As a result, the cleaning interval of the roll becomes longer, the number of times of cleaning can be reduced, and productivity of the synthetic fiber can be improved.
According to the production method of the present invention, the occurrence of scum or yarn breakage can be reduced, and a synthetic filament yarn having excellent yarn quality can be obtained. The fiber structure of the present invention is excellent in quality.
Detailed Description
The agent for treating synthetic fibers of the present invention comprises a smoothing component (A), an organic sulfonic acid compound (B1) represented by the above general formula (1) and an organic sulfonic acid compound (B2) represented by the above general formula (2). The following description will be made in detail.
[ smoothing component (A) ]
The smoothing component (a) is an essential component of the treatment agent of the present invention. As the smoothing component (a), there can be mentioned: 1) known smoothing components generally used as synthetic fiber treating agents include ester compounds (a1) having a structure in which an aliphatic monohydric alcohol forms an ester bond with a fatty acid, 2) ester compounds (a2) having a structure in which an aliphatic polyhydric alcohol forms an ester bond with a fatty acid, 3) ester compounds (A3) having a structure in which an aliphatic monohydric alcohol forms an ester bond with an aliphatic polycarboxylic acid, 4) aromatic ester compounds (a4) having an aromatic ring in the molecule, 5) sulfur-containing ester compounds (a5), and 6) mineral oils (a 6). The smoothing component (A) may be used in 1 type or 2 or more types.
1) Ester compound (A1)
The ester compound (a1) has a structure in which an aliphatic monohydric alcohol and a fatty acid (aliphatic monocarboxylic acid) form an ester bond, and does not have a polyoxyalkylene group in the molecule. The ester compound (a1) may be used in 1 or 2 kinds.
The ester compound (a1) is preferably a compound represented by the following general formula (3).
[ solution 5]
R1-COO-R2 (3)
(in the formula, R1Represents an alkyl group or alkenyl group having 4 to 24 carbon atoms, R2Represents an alkyl group or alkenyl group having 6 to 24 carbon atoms)
R1Preferably has a carbon number of6 to 22, more preferably 8 to 20, and still more preferably 10 to 18. If the number of carbon atoms is less than 4, the oil film is weakened, and the number of piles may increase. On the other hand, if the number of carbon atoms exceeds 24, friction between the fibers increases, which may increase fuzz. R1The alkyl group may be either an alkyl group or an alkenyl group, but is preferably an alkyl group from the viewpoint of excellent heat resistance.
R2The number of carbon atoms of (A) is preferably 6 to 22, more preferably 8 to 20, and further preferably 10 to 18. If the number of carbon atoms is less than 6, the oil film is weakened, and therefore, the amount of fuzz may increase. On the other hand, if the number of carbon atoms exceeds 24, friction between the fibers increases, which may increase fuzz. R2The alkenyl group may be an alkyl group or an alkenyl group, but is preferably an alkenyl group from the viewpoint of high oil film strength and less generation of fluff.
The ester compound (a1) is not particularly limited, and examples thereof include: 2-decyltetradecyltetradecylcarbonyl erucic acid ester, 2-decyltetradecyltetradecylcarbonyl oleate, 2-octyldodecyl stearate, isooctyl palmitate, isooctyl stearate, butyl palmitate, butyl stearate, butyl oleate, isooctyl oleate, lauryl oleate, isotridecyl stearate, cetyl stearate, isostearyl oleate, oleyl octanoate, oleyl laurate, oleyl palmitate, oleyl stearate, oleyl oleate, and the like. Among them, 2-decyltetradecyltetradecanoate oleate, 2-octyldodecyl stearate, isooctyl palmitate, isooctyl stearate, lauryl oleate, isotridecyl stearate, cetyl stearate, isostearyl oleate, oleyl oleate are preferable.
The ester compound (a1) can be synthesized by a known method using a generally commercially available fatty acid and aliphatic monohydric alcohol.
2) Ester compound (A2)
The ester compound (a2) has a structure in which an aliphatic polyhydric alcohol and a fatty acid (aliphatic monocarboxylic acid) form an ester bond, and does not have a polyoxyalkylene group in the molecule. The ester compound (a2) may be used in 1 type or 2 or more types.
The aliphatic polyol constituting the ester compound (a2) is not particularly limited as long as it is a dibasic or higher aliphatic polyol, and 1 or 2 or more aliphatic polyols can be used. From the viewpoint of oil film strength, the polyol is preferably a ternary or higher polyol, more preferably a ternary to quaternary polyol, and still more preferably a ternary polyol.
Examples of the aliphatic polyol include: ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1, 2-butanediol, 1, 3-butanediol, 1, 4-butanediol, 2-methyl-1, 3-propanediol, 1, 5-pentanediol, 1, 6-hexanediol, neopentyl glycol, cyclohexanediol, cyclohexanedimethanol, glycerol, trimethylolpropane, pentaerythritol, erythritol, diglycerol, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, triglycerol, tetraglycerol, sucrose, and the like. Among these, glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, and sucrose are preferable, glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, and sorbitan are more preferable, and glycerin and trimethylolpropane are further more preferable.
The fatty acid constituting the ester compound (a2) may be saturated or unsaturated. The number of unsaturated bonds is not particularly limited, but when the number is 3 or more, the oxidation causes further deterioration, the thickening of the treating agent, and the lubricity deteriorates, and therefore 1 or 2 is preferable. The number of carbon atoms of the fatty acid is preferably 8 to 24, more preferably 10 to 20, and still more preferably 12 to 18 from the viewpoint of compatibility between oil film strength and lubricity. The fatty acid may be used in 1 kind or 2 or more kinds, and a saturated fatty acid and an unsaturated fatty acid may be used in combination.
Examples of the fatty acid include: butyric acid, crotonic acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetylic acid, heptadecanoic acid, stearic acid, isostearic acid, oleic acid, trans-oleic acid, isooleic acid, linoleic acid, linolenic acid, tuberculosic acid, arachidic acid, isoarachidic acid, gadoleic acid (gadolenic acid), eicosenoic acid (eicosenoic acid), behenic acid, isobehenic acid, erucic acid, lignoceric acid, isolignoceric acid, nervonic acid, cerotic acid, montanic acid, melissic acid, and the like.
Among them, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetylic acid, heptadecanoic acid, stearic acid, isostearic acid, oleic acid, trans-oleic acid, vaccenic acid, linoleic acid, linolenic acid, tuberculostearic acid, arachidic acid, isoarachidic acid, gadoleic acid, eicosenoic acid, docosanoic acid, isodocosanoic acid, erucic acid, lignoceric acid, isotetracosanoic acid, nervonic acid, more preferably capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetylic acid, heptadecanoic acid, stearic acid, isostearic acid, oleic acid, trans-oleic acid, isooleic acid, linoleic acid, linolenic acid, tuberculosic acid, arachidic acid, isoarachidic acid, gadoleic acid, eicosenoic acid, further, Pentadecanoic acid, palmitic acid, palmitoleic acid, isocetylic acid, heptadecanoic acid, stearic acid, isostearic acid, oleic acid, trans-oleic acid, isooleic acid, linoleic acid, linolenic acid.
The ester compound (a2) is a compound having 2 or more ester bonds in the molecule, but from the viewpoint of yarn-making properties, a compound having 3 or more ester bonds in the molecule is preferable, and a compound having 3 ester bonds in the molecule is more preferable.
The iodine number of the ester compound (a2) is not particularly limited.
The weight average molecular weight of the ester compound (A2) is preferably 300 to 1200, more preferably 300 to 1000, and further preferably 500 to 1000. When the weight average molecular weight is less than 300, the oil film strength may be insufficient, and the number of piles may increase, or fuming may increase during heat treatment. On the other hand, when the weight average molecular weight exceeds 1200, not only smoothness is insufficient and fluff is frequently generated, but also a high-quality fiber cannot be obtained and the quality in the weaving or knitting step may be deteriorated. The weight average molecular weight of the present invention was calculated from the peak measured by a differential refractive index detector by injecting a sample concentration of 3mg/cc into separation columns KF-402HQ and KF-403HQ manufactured by Showa Denko K.K., using a high-speed gel permeation chromatography apparatus HLC-8220GPC manufactured by Tosoh K.K.
Examples of the ester compound (a2) include: trimethylolpropane tricaprylate, trimethylolpropane tricaprate, trimethylolpropane trilaurate, trimethylolpropane trioleate, trimethylolpropane (laurate, myristate, palmitate), trimethylolpropane (laurate, myristate, oleate), trimethylolpropane (tripalmitin fatty acid ester), trimethylolpropane (tricocoleite), trimethylolpropane dicaprylate, trimethylolpropane dicaprate, trimethylolpropane dilaurate, trimethylolpropane dioleate, trimethylolpropane (laurate, myristate), trimethylolpropane (laurate, oleate), trimethylolpropane (myristate, oleate), trimethylolpropane (dipalmitin fatty acid ester), trimethylolpropane (dicocoleite), trimethylolpropane trioleate, or, Coconut oil, rapeseed oil, palm oil, glycerol trilaurate, glycerol trioleate, glycerol triisostearate, glycerol dioleate, glycerol monolaurate, diglycerol dioleate, sorbitan trioleate, sorbitan (laurate, myristate, oleate), sorbitan dilaurate, sorbitan monooleate, pentaerythritol tetraoctanoate, pentaerythritol tetradecanoate, pentaerythritol tetralaurate, erythritol tetralaurate, pentaerythritol (tetrapalmitin fatty acid ester), pentaerythritol (tetrapalmitin coconut fatty acid ester), erythritol trioleate, erythritol dipalmitate, 1, 6-hexanediol dioleate, and the like.
The ester compound (a2) can be synthesized by a known method using a generally commercially available fatty acid and aliphatic polyol. Alternatively, a natural ester obtained naturally from fruits, seeds, flowers, or the like may be used as it is and the natural ester satisfies the structure of the ester compound (a2), or the natural ester may be purified by a known method as needed, or an ester obtained by separating and purifying an ester further purified by a known method using a difference in melting point may be used. Further, esters obtained by transesterification of 2 or more natural esters (oils and fats) may also be used.
3) Ester compound (A3)
The ester compound (a3) has a structure in which an aliphatic monohydric alcohol and an aliphatic polycarboxylic acid form an ester bond, and does not have a polyoxyalkylene group in the molecule. The ester compound (a3) may be used in 1 type or 2 or more types.
The aliphatic monohydric alcohol constituting the ester compound (a3) is not particularly limited, and 1 type or 2 or more types can be used. The aliphatic monohydric alcohols may be saturated or unsaturated. The number of unsaturated bonds is not particularly limited, but when the number is 2 or more, the oxidation causes further deterioration, the treating agent thickens, and the lubricity is impaired, and therefore one unsaturated bond is preferable. The aliphatic monohydric alcohol has a carbon number of preferably 8 to 24, more preferably 14 to 24, and still more preferably 18 to 22 from the viewpoint of smoothness and oil film strength. The aliphatic monohydric alcohol may be used in 1 type or 2 or more types, and a saturated fatty acid monohydric alcohol and an unsaturated aliphatic monohydric alcohol may be used in combination.
Examples of the aliphatic monohydric alcohol include: octanol, isooctanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, isocetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, trans-oleyl alcohol, isooleyl alcohol, gadoleyl alcohol, arachidyl alcohol, isoeicosenyl alcohol, eicosenyl alcohol, behenyl alcohol, isodocosenyl alcohol, cis-erucyl alcohol, tetracosenyl alcohol, isotetracosenyl alcohol, neryl alcohol, ceryl alcohol, montanyl alcohol, melissinyl alcohol, etc. Among them, octanol, isooctanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, isocetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, trans-oleyl alcohol, isooleyl alcohol, gadoleyl alcohol, arachidyl alcohol, isoeicosenyl alcohol, eicosenyl alcohol, behenyl alcohol, isodocosenyl alcohol, cis-sinenyl alcohol, tetracosenyl alcohol, isotetracosenyl alcohol, and neurol are preferable, myristyl alcohol, palmityl alcohol, oleyl alcohol, trans-oleyl alcohol, isooleyl alcohol, gadoleyl alcohol, eicosenyl alcohol, cis-sinenyl alcohol, and neurol are more preferable, and oleyl alcohol, trans-oleyl alcohol, isooleyl alcohol, gadoleyl alcohol, eicosenyl alcohol, and cis-sinapyl alcohol are further preferable.
The aliphatic polycarboxylic acid constituting the ester (a3) is not particularly limited as long as it is a dibasic acid or more, and 1 or 2 or more species may be used. The aliphatic polycarboxylic acid used in the present invention does not include sulfur-containing polycarboxylic acids such as thiodipropionic acid. The valency of the aliphatic polycarboxylic acid is preferably two. Also, it is preferable that no hydroxyl group is contained in the molecule.
Examples of the aliphatic polycarboxylic acid include: citric acid, isocitric acid, malic acid, aconitic acid, oxaloacetic acid, oxalosuccinic acid, succinic acid, fumaric acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and the like. Among them, aconitic acid, oxaloacetic acid, oxalosuccinic acid, succinic acid, fumaric acid, maleic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid are preferable, and fumaric acid, maleic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid are more preferable.
Examples of the ester compound (a3) include: dioctyl adipate, dilauryl adipate, dioleyl adipate, diisocetyl adipate, dioctyl sebacate, dilauryl sebacate, dioleyl sebacate, diisocetyl sebacate, and the like.
The ester compound (a3) is a compound having 2 or more ester bonds in the molecule. The iodine number of the ester compound (a3) is not particularly limited.
The weight average molecular weight of the ester compound (A3) is preferably 500 to 1000, more preferably 500 to 800, and still more preferably 500 to 700. When the weight average molecular weight is less than 500, the oil film strength may be insufficient, the fluff may increase, and the fuming may increase during the heat treatment. On the other hand, when the weight average molecular weight exceeds 1000, the melting point becomes high, which may cause scum in the weaving or knitting step, thereby deteriorating the quality.
The ester compound (a3) can be synthesized by a known method using a commercially available aliphatic monohydric alcohol and an aliphatic polycarboxylic acid.
4) Aromatic ester Compound (A4)
The aromatic ester compound (a4) is an ester compound having at least 1 aromatic ring in the molecule. In detail, there may be mentioned: an ester compound (A4-1) having a structure in which an aromatic carboxylic acid forms an ester bond with an alcohol, and an ester compound (A4-2) having a structure in which an aromatic alcohol forms an ester bond with a carboxylic acid. The aromatic ester compound (a4) is a compound having no polyoxyalkylene group in the molecule. The aromatic ester compound (a4) may be used in 1 type or 2 or more types.
The aromatic carboxylic acid constituting the ester compound (A4-1) may be a monocarboxylic acid or a polycarboxylic acid. 1 or 2 or more species may be used.
Examples of the aromatic carboxylic acid include: benzoic acid, toluic acid, naphthoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, gallic acid, mellitic acid, cinnamic acid, trimellitic acid, pyromellitic acid, and the like. Among them, trimellitic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferable, and trimellitic acid is more preferable.
The alcohol constituting the ester compound (A4-1) may be a monohydric alcohol or a polyhydric alcohol. Further, any of aliphatic alcohol, alicyclic alcohol, and aromatic alcohol may be used. The monohydric alcohol may be used in 1 or 2 or more species. Among them, monohydric alcohols are preferable, and aliphatic monohydric alcohols are more preferable.
Examples of the monohydric alcohol include: alkylphenols, dialkylphenylalcohols, octanol, isooctanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, isocetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, isooleyl alcohol, gadol alcohol, arachidyl alcohol, isoeicosenyl alcohol, eicosenyl alcohol, behenyl alcohol, isodocosynyl alcohol, cis-erucyl alcohol, tetracosynyl alcohol, isoeicosenyl alcohol, neuronyl alcohol, ceryl alcohol, montanyl alcohol, melissin alcohol and the like.
As the polyhydric alcohol, there may be mentioned: aliphatic polyols described for the ester compound (A2), aromatic polyols described for the ester compound (A4-2), and the like.
The aromatic alcohol constituting the ester compound (A4-2) may be used in 1 type or 2 or more types. The aromatic alcohol is preferably an aromatic polyhydric alcohol, and more preferably an aromatic trihydric alcohol.
Examples of the aromatic alcohol include: aromatic monohydric alcohols such as alkylphenols, and aromatic polyhydric alcohols such as dialkylbenzeneols, bisphenol A, bisphenol Z, and 1,3, 5-trihydroxymethylbenzene. Among them, bisphenol A, bisphenol Z and 1,3, 5-trihydroxymethylbenzene are preferable, and 1,3, 5-trihydroxymethylbenzene is more preferable.
The carboxylic acid constituting the ester compound (a4-2) may be any of an aliphatic carboxylic acid and an aromatic carboxylic acid. Further, any of monocarboxylic acids and polycarboxylic acids may be used. 1 or 2 or more species may be used. Among them, monocarboxylic acids are preferable, and fatty acids are more preferable. From the viewpoint of residue, the fatty acid is preferably saturated. The fatty acid may be linear or branched.
Examples of monocarboxylic acids include: alkylbenzene carboxylic acids, dialkylbenzene carboxylic acids, butyric acid, crotonic acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, myristoleic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, isocetyl acid, heptadecanoic acid, stearic acid, isostearic acid, oleic acid, trans-oleic acid, vaccenic acid, linoleic acid, linolenic acid, tuberculostearic acid, arachidic acid, isoeicosanoic acid, gadoleic acid (gadoleic acid), eicosenoic acid (eicosenoic acid), behenic acid, isoeicosanoic acid, erucic acid, lignoceric acid, isotetracosanoic acid, nervonic acid, cerotic acid, montanic acid, melissic acid, and the like.
Examples of the polycarboxylic acid include: aliphatic polycarboxylic acids described in the ester compound (A3), aromatic polycarboxylic acids described in the ester compound (A4-1), and the like.
5) Sulfur-containing ester Compound (A5)
The sulfur-containing ester compound is at least one selected from a diester compound of thiodipropionic acid and an aliphatic alcohol and a monoester compound of thiodipropionic acid and an aliphatic alcohol.
The sulfur-containing ester compound is a component having an antioxidant ability. By using the sulfur-containing ester compound, the heat resistance of the treating agent can be improved. The sulfur-containing ester compounds may be used in 1 kind or 2 or more kinds. The thiodipropionic acid constituting the sulfur-containing ester compound preferably has a molecular weight of 400 to 1000, more preferably 500 to 900, and further preferably 600 to 800. The aliphatic alcohol constituting the sulfur-containing ester compound may be saturated or unsaturated. The aliphatic alcohol may be linear or branched, but preferably has a branched structure. The aliphatic alcohol preferably has 8 to 24 carbon atoms, more preferably 12 to 24 carbon atoms, and still more preferably 16 to 24 carbon atoms. Examples of the aliphatic alcohol include: octanol, 2-ethylhexyl alcohol, decanol, lauryl alcohol, myristyl alcohol, isocetyl alcohol, oleyl alcohol, isostearyl alcohol, etc., among them, oleyl alcohol and isostearyl alcohol are preferable.
The sulfur-containing ester compound may be a mixture of a diester compound of thiodipropionic acid and an aliphatic alcohol (in this paragraph, simply referred to as a diester) and a monoester compound of thiodipropionic acid and an aliphatic alcohol (in this paragraph, simply referred to as a monoester). In this case, the molar ratio of the diester to the monoester is preferably 100/0 to 70/30, more preferably 100/0 to 75/25, and still more preferably 100/0 to 80/20.
6) Mineral oil (A6)
The synthetic fiber treatment agent of the present invention may contain a mineral oil as a smoothing component other than the above. The mineral oil referred to herein is not a low viscosity diluent used for diluting the treating agent, but is contained in a nonvolatile component. The mineral oil is not particularly limited, and examples thereof include: machine oil, spindle oil, liquid paraffin, etc. The mineral oil can be 1 or more than 2. The viscosity of the mineral oil at 30 ℃ is preferably 100 to 500 seconds.
The smoothing component (a) is preferably purified by removing the catalyst and the like from the viewpoint of improving heat resistance.
[ organic sulfonic acid Compound ]
In the treating agent of the present invention, 2 kinds of organic sulfonic acid compounds, i.e., the organic sulfonic acid compound (B1) represented by the above general formula (1) and the organic sulfonic acid compound (B2) represented by the above general formula (2), are essential components. The respective components will be described in detail.
The organic sulfonic acid compound (B1) is a monosulfonic acid compound having one sulfonic acid group in the molecule, and is an essential component of the treating agent of the present invention. The organic sulfonic acid compound (B1) may be used in 1 kind, or 2 or more kinds may be used in combination.
In the general formula (1), a and b are integers of 0 or more and satisfy a + b of 5 to 17. When a + b is less than 5, the effect of reducing the contamination of the roller becomes small. On the other hand, if a + b exceeds 17, the melting point is high, and the compatibility with the treating agent is poor, and thus the composition cannot be used. The a + b is preferably 7 to 17, and more preferably 10 to 15.
M is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. Examples of the alkali metal include: lithium, sodium, potassium, and the like. As ammonium groups and organic amine groups, there may be mentioned: from NRaRbRcRdThe group shown. Ra、Rb、RcAnd RdEach independently represents a hydrogen atom, an alkyl group, an alkenyl group, or a polyoxyalkylene group. The number of carbon atoms of the alkyl group and the alkenyl group is preferably 1 to 24, more preferably 1 to 20, and further preferably 1 to 18. [ - (A) for polyoxyalkylene1O)mH]Is represented by (A)1O)mThe same as the case represented by the general formula (2).
As a result of NRaRbRcRdExamples of the group represented include: ammonium group, methylammonium group, ethylammonium group, propylammonium group, butylammonium group, hexylammonium group, octylammonium group, dimethylammonium group, diethylammonium group, dipropylammonium group, dibutylammonium group, dihexylammonium group, dioctylammonium group, trimethylammonium group, triethylammonium group, tripropylammonium group, tributylammonium group, trihexylammonium group, trioctylammonium group, tetramethylammonium group, tetraethylammonium group, tetrapropylammonium group, tetrabutylammonium group, tetrahexylammonium group, tetraoctylammonium group, ethyltrimethylammonium group, propyltrimethylammonium group, butyltrimethylammonium group, hexyltrimethylammonium group, octyltrimethylammonium group, methanolammonium group, ethanolammonium group, propanolammonium group, butanolammonium group, hexanolammonium group, octanolammonium group, dimethalammonium group, diethanolammonium group, dipropanolammonium group, dibutanolammonium group, dihexylammonium group, dioctanolammonium group, trimethylammonio group, triethanolammonium group, dimethyl ammonium group, diethylammonium group, dibutyl ammonium group, tert-butylammonium group, tert-trimethylammonium group, tert-butylammonium group, octyltrimethylammonium group, tripropylammonium, tributylammonium, trihexylammoniumTri-octanol ammonium group, (EO6) butyl amino ether group, (EO6) hexyl amino ether group, (EO6) octyl amino ether group, (EO6) decyl amino ether group, (EO6) lauryl amino ether group, (EO6) tetradecyl amino ether group, (EO6) cetyl amino ether group, (EO6) oleyl amino ether group, (EO6) stearyl amino ether group, (EO6) cod oleyl amino ether group, (EO6) tetracosan amino ether group, (EO10) oleyl amino ether group, (EO10) oleyl amino ether group/erucic acid salt, (EO3) lauryl ether group, (EO3) lauryl amino ether group, (EO7) lauryl amino ether group, (EO15) oleyl amino group, (PO3, EO5) stearyl amino ether group, (PO5, EO3) stearyl amino ether group.
The organic sulfonic acid compound (B2) is a disulfonic acid compound having 2 sulfonic acid groups in the molecule. By using the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2) in combination in addition to the smoothing component (A), fluff, yarn breakage, and roll contamination can be greatly reduced. The organic sulfonic acid compound (B2) may be used in 1 kind, or 2 or more kinds may be used in combination.
In the formula (2), c, d, and e are integers not less than 0, and c + d + e is an integer of 4 to 16. When c + d + e is less than 4, the effect of reducing the roll contamination may be small. On the other hand, if c + d + e exceeds 17, the compatibility with the treating agent is poor, and it may not be used. c + d + e is preferably 6 to 16, and more preferably 9 to 14.
M is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. The details of M are the same as those of M described in the general formula (1).
From the viewpoint of compatibility of the synthetic fiber-treating agent, the weight ratio (B1/B2) of the organic sulfonic acid compound (B1) to the organic sulfonic acid compound (B2) is preferably 50/50 to 99/1, more preferably 70/30 to 99/1, and still more preferably 80/20 to 98/2.
In the raw material containing the organic sulfonic acid compound (B1) and/or the organic sulfonic acid compound (B2), sodium sulfate and/or sodium chloride are contained in many cases due to the production method thereof. The ratio of sodium sulfate and sodium chloride contained in these raw materials can be calculated by ion chromatography from the weight ratio of sulfate ions and chloride ions detected from the raw materials.
From the viewpoint of exhibiting the effects of the present invention, it is preferable to use a raw material containing an organic sulfonic acid compound (B1) and/or an organic sulfonic acid compound (B2) in which sodium sulfate and sodium chloride are reduced. Specifically, it is preferable to use a raw material in which the weight ratio of sulfate ions detected by ion chromatography is 5000ppm or less and the weight ratio of chloride ions is 5000ppm or less, based on the total amount of the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2).
From the viewpoint of further exhibiting the effect of the present invention, the weight ratio of the sulfate ion is more preferably 4000ppm or less, still more preferably 3000ppm or less, and particularly preferably 2000ppm or less. Similarly, the weight ratio of the chlorine ions is preferably 4000ppm or less, more preferably 3000ppm or less, and particularly preferably 2000ppm or less.
The method for analyzing sulfate ions and chloride ions by ion chromatography in the present invention was performed according to the method described in examples.
The method for reducing sodium sulfate or sodium chloride from the raw material X containing the organic sulfonic acid compound (B1) and/or the organic sulfonic acid compound (B2) is not particularly limited, and a known method can be employed. For example, there may be mentioned: when the raw material contains sodium sulfate, a solvent such as methanol or water is added to the raw material, and an inorganic substance such as sodium sulfate is precipitated and separated. When the raw material X contains sodium chloride, examples thereof include: a method of removing sodium chloride contained in the raw material by an ion exchange membrane, a method of adsorbing by an ion exchange resin, and the like.
[ organic phosphate ester Compound (C) ]
In the treatment agent of the present invention, it is preferable that the smoothing component (a), the organic sulfonic acid compound (B1), and the organic sulfonic acid compound (B2) further contain an organic phosphate compound (C) in addition to the above smoothing component (a), the organic sulfonic acid compound (B1), and the organic sulfonic acid compound (B2), from the viewpoint of reducing fuzz. The organic phosphate compound (C) is preferably at least one selected from the compounds represented by the above general formula (4) and the compounds represented by the above general formula (5).
In the general formulae (4) and (5), R3Is a hydrocarbon group having 6 to 24 carbon atoms. A. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15. n is an integer of 1 to 2. M1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. Q1Is M1Or R3O(A1O)m. Y is 1 or 2.
As R3Examples of the hydrocarbon group of (1) include: alkyl, alkenyl, and the like. R3The number of carbon atoms of (A) is preferably 8 to 24, more preferably 12 to 24. R3May also have a distribution of carbon atoms, R3The polymer may be linear or branched, and may be saturated or unsaturated.
A1O is an oxyalkylene group having 2 to 4 carbon atoms. The repeating number m of oxyalkylene units is an integer of 0 to 15, preferably 0 to 10, more preferably 0 to 3, and particularly preferably m is 0, that is, m is not polyoxyalkylene. (A)1O)mPreferably, the oxyalkylene unit is a polyoxyalkylene group containing 50 mol% or more of oxyethylene units.
n is an integer of 1 to 2. When n is 2, 2 organic groups "R" constituting the compound represented by the above general formula (4)3O(A1O)mThe "may be the same or different.
In addition, when Q ═ R3O(A1O)mIn the case (2) of the organic groups "R" constituting the compound represented by the general formula (5)3O(A1O)mThe "may be the same or different.
M1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group. Examples of the alkali metal include: lithium, sodium, potassium, and the like. Examples of the ammonium group and the organic amine group include: from NRaRbRcRdThe group shown. From NRaRbRcRdThe group represented is the same as M illustrated at the organic sulfonic acid compound (B).
The organic phosphate compound (C) is preferably a mixture containing an organic phosphate compound (C1) represented by the general formula (4) wherein n is 1 and an organic phosphate compound (C2) represented by the general formula (4) wherein n is 2, or an organic phosphate compound(C1) (C2) and general formula (5) wherein Y is 1 and Q is R3O(A1O)mA mixture of the organic phosphate compounds (C3). These mixtures may contain an organic phosphate compound (C4) represented by general formula (5) wherein Y is 1 and Q is a hydrogen atom.
The P nucleus integration ratio (%) of the organic phosphate ester compounds (C1), (C2), (C3) and (C4) and the inorganic phosphoric acid can be determined according to31The integral value of the peak derived from each phosphorus atom in P-NMR was calculated. The P-nucleus integration ratio (%) is a value calculated by setting the total of the integrated values of the organic phosphate compound (C1), (C2), (C3), and (C4) and the inorganic phosphoric acid to 100%. The inorganic phosphoric acid will be described later.
The P-nucleus integral ratio (%) of the organic phosphate compound (C1) is preferably 25 to 85%, more preferably 35 to 80%, and still more preferably 40 to 70%. The P-nucleus integral ratio (%) of the organic phosphate compound (C2) is preferably 15 to 65%, more preferably 20 to 60%, and still more preferably 25 to 55%. The P-nucleus integral ratio (%) of the organic phosphate ester compound (C3) is preferably 0 to 50%, more preferably 0 to 45%, and still more preferably 0 to 40%. The P-nucleus integral ratio (%) of the organic phosphate ester compound (C4) is preferably 0 to 7%, more preferably 0 to 6%, and still more preferably 0 to 5%. The inorganic phosphoric acid preferably has a P nucleus integral ratio (%) of 0 to 10%, more preferably 0 to 9%, and further preferably 0 to 8%.
The method for producing the organic phosphate compound (C) is not particularly limited, and a known method can be used. For example, the process for producing the organic phosphoric acid ester compound (C) comprises reacting R3O(A1O)mOrganic hydroxy compound represented by H and phosphoric anhydride P2O5And (I) reacting the resulting product to obtain a reaction product. In the step (I), inorganic phosphoric acid and water may be added to carry out the reaction. The method for producing the organic phosphate compound (C) may include the step (II) of adding water to the reaction product after the step (I) to hydrolyze the reaction product. By including the step (II), the ratio of the organic phosphate compound (C3) to the organic phosphate compound (C4) can be adjusted. Relative to the organophosphate esterificationThe amount of water added to the reaction product of the compound (C) is preferably 0.01 to 5 wt%, more preferably 0.05 to 4 wt%, and still more preferably 0.1 to 3 wt%. If the amount of water added is less than 0.01% by weight or exceeds 5% by weight, it may be difficult to adjust the amounts of the organic phosphate compounds (C3) and (C4). The process for producing the organic phosphate compound (C) may include the step (I) or the step (II) followed by the step (I) or the step (II) with a compound having M1Step (III) of neutralizing the alkali compound.
The organic phosphate compound (C) contains a heavy metal compound such as arsenic as an impurity source in phosphoric anhydride or inorganic phosphorus. The treating agent of the present invention may contain a heavy metal compound such as arsenic. From the viewpoint of the effect on the human body or the safety to the environment, the weight ratio of the heavy metal compound to the nonvolatile component of the treating agent is preferably 0.01 wt% or less, more preferably 0.005 wt% or less, and still more preferably 0.001 wt% or less.
In the production of the organic phosphate compound (C), inorganic phosphoric acid and/or a salt thereof is produced. Therefore, the raw material containing the organic phosphate compound (C) (hereinafter referred to as raw material Z) contains inorganic phosphoric acid and/or a salt thereof. The ratio of the inorganic phosphoric acid and/or salt thereof can be determined by the ratio of the organic hydroxy compound to the phosphoric anhydride P2O5The ratio of (A) to (B) and the reaction conditions are adjusted.
[ nonionic surfactant (D) ]
The treating agent of the present invention preferably contains a nonionic surfactant (D) in addition to the smoothing component (a), the organic sulfonic acid compound (B1), and the organic sulfonic acid compound (B2) from the viewpoint of imparting oil film strength to the strands, bundling properties, and improving yarn-making properties. The nonionic surfactant (D) is a substance other than the smoothing component (a). The nonionic surfactant (D) may be used in 1 kind or 2 or more kinds.
Examples of the nonionic surfactant (D) include: polyoxyalkylene group-containing hydroxy fatty acid polyol esters (hereinafter, sometimes referred to as "polyhydroxy esters" (ポリヒドロキシエステル)), esters in which at least one of the hydroxyl groups of a polyhydroxy ester is capped with a fatty acid, polyalkylene oxide polyol ethers, polyalkylene oxide polyol fatty acid esters, polyalkylene oxide fatty alcohol ethers, polyalkylene glycol fatty acid esters, and polyol fatty acid esters.
(polyhydroxy ester, ester wherein at least one hydroxyl group of polyhydroxy ester is capped with fatty acid)
The polyhydroxy ester is preferably an ester of a polyoxyalkylene group-containing hydroxy fatty acid and a polyhydric alcohol in structure, and 2 or more of the hydroxyl groups of the polyhydric alcohol are esterified. Thus, a polyoxyalkylene group-containing polyol ester of a hydroxy fatty acid is an ester having a plurality of hydroxyl groups.
The polyoxyalkylene group-containing hydroxy fatty acid has a structure in which a polyoxyalkylene group is bonded to a hydrocarbon group of a fatty acid through an oxygen atom, and one end of the polyoxyalkylene group which is not bonded to the hydrocarbon group of the fatty acid is a hydroxyl group.
Examples of the polyhydroxy ester include: alkylene oxide adducts of esters of hydroxy fatty acids having 6 to 22 carbon atoms (preferably 16 to 20 carbon atoms) and polyhydric alcohols.
Examples of the hydroxy fatty acid having 6 to 22 carbon atoms include: hydroxyoctanoic acid, hydroxydecanoic acid, hydroxylauric acid, hydroxystearic acid, ricinoleic acid, preferably hydroxyoctadecanoic acid, ricinoleic acid. Examples of the polyhydric alcohol include: ethylene glycol, glycerin, sorbitol, sorbitan, trimethylolpropane, pentaerythritol, etc., with glycerin being preferred. Examples of the alkylene oxide include: alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide, propylene oxide, and butylene oxide.
The number of moles of alkylene oxide added is preferably 3 to 60, more preferably 8 to 50. The proportion of ethylene oxide in the alkylene oxide is preferably 50 mol% or more, and more preferably 80 mol% or more.
When 2 or more alkylene oxides are added, the order of addition is not particularly limited, and the addition form may be any of a block form and a random form. The addition of alkylene oxide can be carried out by known methods, but is usually carried out in the presence of a basic catalyst.
Polyhydroxy esters can be produced, for example, as follows: the alkylene oxide-based resin composition is produced by esterifying a polyhydric alcohol and a hydroxy fatty acid (hydroxymonocarboxylic acid) under ordinary conditions to obtain an esterified product, and then subjecting the esterified product to an addition reaction with an alkylene oxide. Polyhydroxy esters can also be suitably made by: the oil-and-fat composition is obtained by using a naturally-obtained oil-and-fat such as castor oil or hydrogenated castor oil obtained by adding hydrogen thereto, and further performing an addition reaction with an alkylene oxide.
The nonionic surfactant (D) also contains the above-mentioned ester obtained by capping at least one hydroxyl group of the polyhydroxy ester with a fatty acid. The number of carbon atoms of the blocked fatty acid is preferably 6 to 24, more preferably 12 to 18. The number of carbon atoms of the hydrocarbon group in the fatty acid may have a distribution, and the hydrocarbon group may be linear, branched, saturated, unsaturated, or polycyclic. Examples of such fatty acids include: lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, eicosanoic acid, behenic acid, lignoceric acid, and the like. The method of esterification, reaction conditions, and the like are not particularly limited, and a known method and ordinary conditions can be employed.
Examples of the polyhydroxy ester and the ester obtained by capping at least one hydroxyl group of the polyhydroxy ester with a fatty acid include hydrogenated castor oil ethylene oxide adduct, hydrogenated castor oil ethylene oxide adduct monooleate, hydrogenated castor oil ethylene oxide adduct dioleate, hydrogenated castor oil ethylene oxide adduct trioleate, hydrogenated castor oil ethylene oxide adduct tristearate, and among them, from the viewpoint of compatibility of the treating agent, oil film strength, and reduction of fuzz, hydrogenated castor oil ethylene oxide adduct trioleate, and hydrogenated castor oil ethylene oxide adduct tristearate are preferable.
(polyoxyalkylene polyol ether)
The polyoxyalkylene polyol ether is a compound having a structure obtained by adding an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide to a polyol.
Examples of the polyol include: ethylene glycol, glycerol, trimethylolpropane, pentaerythritol, diglycerol, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, sucrose, and the like. Among them, glycerin, trimethylolpropane, and sucrose are preferable.
The number of moles of alkylene oxide added is preferably 3 to 100, more preferably 4 to 70, and still more preferably 5 to 50. The proportion of ethylene oxide in the alkylene oxide is preferably 50 mol% or more, and more preferably 80 mol% or more.
The polyoxyalkylene polyol ether preferably has a weight average molecular weight of 300 to 10000, more preferably 400 to 8000, and further preferably 500 to 5000. When the molecular weight is less than 300, the generation of fuzz and yarn breakage cannot be reduced. On the other hand, if the molecular weight exceeds 10000, the friction of the treating agent increases, and the occurrence of fuzz and yarn breakage cannot be reduced, but rather worsens.
Examples of polyoxyalkylene polyol ethers include: polyethylene glycol, glycerin ethylene oxide adduct, trimethylolpropane ethylene oxide adduct, pentaerythritol ethylene oxide adduct, diglycerin ethylene oxide adduct, sorbitan ethylene oxide propylene oxide adduct, sorbitol ethylene oxide propylene oxide adduct, ditrimethylol propylene oxide adduct, dipentaerythritol ethylene oxide adduct, sucrose ethylene oxide adduct, and the like, but are not limited thereto.
(polyoxyalkylene polyol fatty acid ester)
The polyoxyalkylene polyol fatty acid ester is a compound having a structure in which an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide is added to a polyol to form an ester bond with a fatty acid.
Examples of the polyol include: glycerin, trimethylolpropane, pentaerythritol, erythritol, diglycerin, sorbitan, sorbitol, ditrimethylolpropane, dipentaerythritol, sucrose, and the like. Among them, glycerin, diglycerin, sorbitan, and sorbitol are preferable.
Examples of the fatty acid include: lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, isocetylic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidic acid, eicosenoic acid, behenic acid, isodocosanoic acid, erucic acid, lignoceric acid, isolignoceric acid, and the like.
The number of moles of alkylene oxide added is preferably 3 to 100, more preferably 5 to 70, and still more preferably 10 to 50. The proportion of ethylene oxide in the alkylene oxide is preferably 50 mol% or more, and more preferably 80 mol% or more.
The polyoxyalkylene polyol fatty acid ester preferably has a weight average molecular weight of 300 to 7000, more preferably 500 to 5000, and further preferably 700 to 3000. When the molecular weight is less than 300, smoke may be generated in the heat treatment step, and the environment may be deteriorated. Further, the occurrence of yarn breakage cannot be reduced. On the other hand, if the molecular weight exceeds 7000, the friction of the treating agent increases, and the generation of fuzz and yarn breakage cannot be reduced, but rather, is deteriorated.
Examples of the polyoxyalkylene polyol fatty acid ester include: glycerol ethylene oxide adduct monolaurate, glycerol ethylene oxide adduct dilaurate, glycerol ethylene oxide adduct trilaurate, trimethylolpropane ethylene oxide adduct trilaurate, sorbitan ethylene oxide adduct monooleate, sorbitan ethylene oxide adduct dioleate, sorbitan ethylene oxide adduct trioleate, sucrose ethylene oxide adduct trilaurate, and the like, but are not limited thereto.
(polyoxyalkylene aliphatic alcohol ethers)
The polyoxyalkylene aliphatic alcohol ether is a compound having a structure obtained by adding an alkylene oxide such as ethylene oxide, propylene oxide, or butylene oxide to an aliphatic monohydric alcohol.
Examples of the polyoxyalkylene aliphatic alcohol ether include: alkylene oxide adducts of aliphatic alcohols such as octanol, 2-ethylhexanol, decanol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, stearyl alcohol, isostearyl alcohol, and oleyl alcohol.
The number of moles of alkylene oxide added is preferably 1 to 100 moles, more preferably 2 to 70 moles, and still more preferably 3 to 50 moles. The proportion of ethylene oxide to the whole alkylene oxide is preferably 20 mol% or more, more preferably 30 mol% or more, and still more preferably 40 mol% or more.
(fatty acid ester of polyalkylene glycol)
The fatty acid ester of a polyalkylene glycol is a compound having a structure in which polyoxyethylene glycol or polyoxyethylene polyoxypropylene glycol forms an ester bond with a fatty acid. The weight average molecular weight of the polyalkylene glycol is preferably 100 to 1000, more preferably 150 to 800, and further preferably 200 to 700.
Examples of the polyalkylene glycol fatty acid ester include: polyethylene glycol monolaurate, polyethylene glycol dilaurate, polyethylene glycol monooleate, polyethylene glycol dioleate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene polypropylene glycol monolaurate, polyethylene polypropylene glycol dilaurate, polyethylene polypropylene glycol monooleate, polyethylene polypropylene glycol dioleate, and the like, but is not limited thereto.
(polyol fatty acid ester)
The polyol fatty acid ester is a compound having a structure in which an ester bond is formed between a polyol and a fatty acid, and is a compound other than the smoothing component (a).
Examples of the polyol include: ethylene glycol, trimethylolpropane, pentaerythritol, erythritol, diethylene glycol, diglycerol, sorbitan, sorbitol, ditrimethylolpropane, sucrose, and the like. Among them, ethylene glycol, glycerin, diglycerin, sorbitan, and sorbitol are preferable.
Examples of the fatty acid include: lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, isocetylic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, tuberculostearic acid, isoeicosanoic acid, gadoleic acid (gadoleic acid), eicosenoic acid (eicosenoic acid), behenic acid, isoeicosanoic acid, erucic acid, lignoceric acid, and the like.
The polyol fatty acid ester has at least 1 or 2 or more hydroxyl groups.
The weight average molecular weight of the polyol fatty acid ester is preferably 100 to 1000, more preferably 200 to 800, and further preferably 300 to 600.
Examples of the fatty acid ester include: glycerol monolaurate, glycerol dilaurate, glycerol monooleate, glycerol dioleate, sorbitan monooleate, sorbitan dioleate, sucrose monolaurate, sucrose dilaurate, and the like, but are not limited thereto.
The nonionic surfactant (D) is preferably purified by removing the catalyst and the like from the viewpoint of improving heat resistance.
[ treating agent for synthetic fiber ]
The weight ratio of the smoothing component (A) to the nonvolatile component of the treating agent is preferably 20 to 70 wt%, more preferably 30 to 65 wt%, further preferably 40 to 65 wt%, and particularly preferably 40 to 60 wt%. When the weight ratio is less than 20% by weight, smoothness may be insufficient, resulting in increased fuzz. On the other hand, if the weight ratio exceeds 70 wt%, the bundling property is insufficient, and in the case of using in emulsion, the emulsion stability may be deteriorated and it may not be possible to use.
The total weight ratio of the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2) in the nonvolatile component of the treating agent is preferably 0.5 to 7% by weight, more preferably 1.0 to 7% by weight, still more preferably 1.25 to 6% by weight, and particularly preferably 1.5 to 6% by weight. When the weight ratio is less than 0.5 wt%, the roll contamination may not be reduced. On the other hand, when the weight ratio exceeds 7% by weight, friction increases and fluff increases.
The organic sulfonic acid compound (B1) is preferably contained in an amount of 0.25 to 6.93 wt%, more preferably 0.5 to 5.94 wt%, even more preferably 0.63 to 5.94 wt%, and particularly preferably 0.75 to 5.94 wt%, based on the nonvolatile content of the treating agent.
The organic sulfonic acid compound (B2) is contained in an amount of preferably 0.005 to 3.5% by weight, more preferably 0.01 to 3.5% by weight, still more preferably 0.13 to 3.0% by weight, and particularly preferably 0.015 to 2.0% by weight, based on the nonvolatile components of the treating agent.
Preferably, the treating agent of the present invention is a sulfate ion (SO) detected by ion chromatography from nonvolatile components of the treating agent4 2-) Is 300ppm or less, and chloride ion (Cl)-) The weight ratio of (B) is 300ppm or less. Fluff, yarn breakage, and roll contamination can be further reduced by setting the sulfate ion and the chloride ion detected from the nonvolatile component of the treating agent to a predetermined weight ratio or less.
The method for analyzing sulfate ions and chloride ions by ion chromatography according to the present invention is as described in examples. The nonvolatile component in the present invention means an absolute dry component when a constant amount is reached by removing a solvent or the like by heat-treating a treating agent at 105 ℃.
From the viewpoint of further exhibiting the effects of the present invention, the weight ratio of the sulfate ion is preferably 250ppm or less, more preferably 200ppm or less, and still more preferably 100ppm or less. Similarly, the weight ratio of the chlorine ions is preferably 250ppm or less, more preferably 200ppm or less, and still more preferably 100ppm or less.
As described above, the method of adjusting the weight ratio of sulfate ions to chloride ions can be achieved by reducing sodium sulfate and sodium chloride contained in the raw material containing the organic sulfonic acid compound (B1) and/or the organic sulfonic acid compound (B2).
When the treating agent of the present invention contains the organic phosphate compound (C), the organic phosphate compound (C) is contained in an amount of preferably 0.05 to 10% by weight, more preferably 0.08 to 8% by weight, and still more preferably 0.1 to 7% by weight, based on the nonvolatile components of the treating agent.
When the treating agent of the present invention contains the organic phosphate compound (C), it is preferable that phosphate ion (PO) detected from nonvolatile components of the treating agent by ion chromatography4 3-) The weight ratio of (B) is 500ppm or less. When the weight ratio of the phosphate ions exceeds 500ppm, the phosphate ions may be dropped on the drawing roll to increase yarn breakage. The weight ratio of the phosphate ion is more preferably 400ppm or less, still more preferably 300ppm or less, and particularly preferably 200ppm or less. In some cases, phosphate ion (PO) is used4 3-) Referred to as phosphate ions for short.
The method of adjusting the weight ratio of the phosphate ions can be achieved by reducing the inorganic phosphoric acid and/or a salt thereof contained in the raw material Z containing the organic phosphate compound (C), adjusting the amount of the raw material Z to be blended, or filtering the treating agent with a filter aid such as diatomaceous earth, as described above.
From the viewpoint of further exhibiting the effects of the present invention, sulfate ions (SO) detected from nonvolatile components of the treating agent by ion chromatography4 2-) Chloride ion (Cl)-) And phosphate ion (PO)4 3-) The total weight ratio of (A) is preferably 500ppm or less, more preferably 300ppm or less, further preferably 200ppm or less, particularly preferably 150ppm or less, and most preferably 100ppm or less.
When the treating agent of the present invention contains the nonionic surfactant (D), the weight ratio of the nonionic surfactant (D) to the nonvolatile component of the treating agent is preferably 20 to 70% by weight, more preferably 25 to 65% by weight, still more preferably 30 to 65% by weight, and particularly preferably 30 to 60% by weight.
(other Components)
The synthetic fiber-treating agent of the present invention may contain a surfactant other than the organic sulfonic acid compound (B1), the organic sulfonic acid compound (B2), the organic phosphate compound (C), and the nonionic surfactant (D) described above in order to emulsify the treating agent, assist adhesion to fibers, water washing of the treating agent from fibers, impart electroconductivity, lubricity, bundling properties to fibers, and the like. Examples of such surfactants include anionic surfactants such as fatty acid soaps; cationic surfactants such as alkylamine salts, alkylimidazolium salts and quaternary ammonium salts; amphoteric surfactants such as lauryl dimethyl betaine and stearyl dimethyl betaine; dimethyl lauryl amine oxide and the like. These surfactants may be used in 1 kind or 2 or more kinds. When these surfactants are contained, the weight ratio of the surfactant to the nonvolatile component of the treating agent is not particularly limited, but is preferably 0.01 to 15% by weight, and more preferably 0.1 to 10% by weight. The surfactant referred to herein means a surfactant having a weight average molecular weight of less than 1000.
The synthetic fiber treatment agent of the present invention may further contain an antioxidant for imparting heat resistance. Examples of the antioxidant include: known antioxidants such as phenol type, sulfur type, phosphite type and the like. The antioxidant may be used in 1 or 2 or more. When the antioxidant is contained, the weight ratio of the antioxidant to the nonvolatile components of the treating agent is not particularly limited, but is preferably 0.1 to 5% by weight, and more preferably 0.1 to 3% by weight.
The synthetic fiber treatment agent of the present invention may further contain a stock solution stabilizer (e.g., water, ethylene glycol, propylene glycol). The weight ratio of the stock solution stabilizer in the treating agent is preferably 0.1 to 30 wt%, and more preferably 1 to 20 wt%.
The synthetic fiber-treating agent of the present invention may be composed of the above components containing only nonvolatile components, may be composed of nonvolatile components and a base solution stabilizer, may be a treating agent obtained by diluting nonvolatile components with a low-viscosity mineral oil, or may be an aqueous emulsion obtained by emulsifying nonvolatile components in water. The treatment agent for synthetic fibers of the present invention is an aqueous emulsion obtained by emulsifying a nonvolatile component in waterIn this case, the concentration of the nonvolatile component is preferably 5 to 35% by weight, more preferably 6 to 30% by weight. The viscosity (30 ℃) of the treating agent after the nonvolatile component is diluted with a low-viscosity mineral oil is preferably 3 to 120mm from the viewpoint of uniform application to the fiber material2And/s, more preferably 5 to 100mm2/s。
The method for producing the synthetic fiber treating agent of the present invention is not particularly limited, and a known method can be used. The synthetic fiber treating agent can be produced by adding and mixing the above components in an arbitrary or specific order. From the viewpoint of improving heat resistance, each component may be purified by removing a catalyst or the like. In particular, in the case where the smoothing component (a) and the nonionic surfactant (D) used in the present invention contain an inorganic substance, it is preferable to remove the inorganic substance and purify the same when the inorganic substance significantly reduces the effect of the present invention. The method of removing inorganic substances and purifying them can be carried out by a known method, for example, in the case of the smoothing component (A), they can be removed by filtration using diatomaceous earth, and in the case of the nonionic surfactant (D), they can be purified by adsorption removal using an inorganic synthetic adsorbent.
[ Process for producing synthetic fiber filament yarn and fiber Structure ]
The method for producing a synthetic fiber filament yarn of the present invention includes a step of applying the synthetic fiber treatment agent of the present invention to a raw synthetic fiber filament yarn. According to the production method of the present invention, the occurrence of scum or yarn breakage can be reduced, and a synthetic fiber filament yarn having excellent yarn quality can be obtained. The raw synthetic fiber filament yarn in the present invention is a synthetic fiber filament yarn to which no treatment agent is added.
The step of applying the treatment agent for synthetic fibers is not particularly limited, and a known method can be used. In general, a treatment agent for synthetic fibers is applied to a raw material synthetic fiber filament yarn in a spinning process. After the treatment agent is applied, the sheet is stretched by a heat roll, thermally cured (thermal curing), and wound up. As described above, when a step of performing hot drawing without winding up is provided after the treatment agent is applied, the treatment agent for synthetic fibers of the present invention can be suitably used. The temperature at the time of hot drawing is, for example, 210 to 260 ℃ for polyester and nylon, if they are industrial materials, and 110 to 220 ℃ for clothing.
The synthetic fiber treating agent to be applied to the raw synthetic fiber filament yarn includes, as described above: a treating agent composed only of nonvolatile components, a treating agent in which nonvolatile components are diluted with a low-viscosity mineral oil, or an aqueous emulsion treating agent in which nonvolatile components are emulsified in water. The method of applying the coating is not particularly limited, and examples thereof include: induction oil feed, roll oil feed, immersion oil feed, spray oil feed, and the like. Among them, guide oil feeding and roll oil feeding are preferable from the viewpoint of easy management of the amount of application.
The amount of the nonvolatile component of the synthetic fiber treating agent applied to the raw synthetic fiber filament yarn is preferably 0.05 to 5 wt%, more preferably 0.1 to 3 wt%, and still more preferably 0.1 to 2 wt%. If the content is less than 0.05% by weight, the effects of the present invention may not be exhibited. On the other hand, when the amount exceeds 5% by weight, nonvolatile components of the treating agent tend to fall off in the yarn path, and tar on the heat roll increases significantly, which may cause fuzzing or yarn breakage.
Examples of the (raw material) synthetic fiber filament yarn include: filament yarns of synthetic fibers such as polyester fibers, polyamide fibers, and polyolefin fibers. The agent for treating synthetic fibers of the present invention is suitable for use in synthetic fibers such as polyester fibers, polyamide fibers, and polyolefin fibers. Examples of the polyester fiber include: examples of the polyamide fibers include Polyester (PET) mainly composed of ethylene terephthalate, Polyester (PTT) mainly composed of trimethylene terephthalate (トリメチレンエチレンテレフタレート), Polyester (PBT) mainly composed of butylene terephthalate (ブチレンエチレンテレフタレート), and Polyester (PLA) mainly composed of lactic acid: nylon 6, nylon 66, and the like, and examples of the polyolefin fiber include: polypropylene, polyethylene, and the like. The method for producing the synthetic fiber filament yarn is not particularly limited, and a known method can be used.
(fiber Structure)
The fiber structure of the present invention contains the synthetic fiber filament yarn obtained by the above-described production method of the present invention. Specifically, the synthetic fiber filament yarn to which the synthetic fiber treatment agent of the present invention is applied is used for woven fabrics woven by a water jet loom, an air jet loom, or a rapier loom, knitted articles woven by a circular knitting machine, a longitudinal knitting machine, or a transverse knitting machine, and strings or ropes obtained by twisting. Further, as applications of the fiber structure, there are: industrial materials such as tire cords, safety belts, airbags, fishing nets and ropes, and clothing. The method for producing the woven fabric or the knit fabric is not particularly limited, and a known method can be employed.
Examples
The present invention is illustrated by the following examples. The present invention is not limited to the embodiments described herein. In the text and in the tables, "%" means "% by weight". Examples 5, 10, 11, and 12 are referred to as reference examples 5, 10, 11, and 12.
Examples 1 to 12 and comparative examples 1 to 5
The components described in tables 1 and 2 were mixed and stirred until uniform to prepare a treating agent. Using each of the prepared treatment agents, the accumulation of stain in the strut (pin), the wiping properties of stain on the strut, and the tension fluctuation were evaluated by the following methods. Further, sulfate ion (SO) was measured by the following method using nonvolatile components of the treating agent4 2-) Chloride ion (Cl)-) Phosphate radical ion (PO)4 3-). The results are shown in tables 1 and 2.
(evaluation of fouling accumulation of struts, wiping of fouling of struts, and tension fluctuation)
The oil-free polyester filaments having 1000 denier and 96 filaments were quantitatively given to the above-prepared treating agent in an amount of 20 wt%, passed through a roller heated to 150 ℃ in a running method friction measuring machine to remove volatile components, and then contacted with a satin chromium strut heated to 250 ℃ to be run for 4 hours at an initial tension of 500g and a running speed of 2 m/min, and the degree of accumulation of stain on the strut, the wiping property of stain on the strut, and the tension fluctuation were evaluated. For more rigorous evaluation, 20 wt% of the treating agent was added.
The degree of accumulation of contamination of the struts was evaluated by the following criteria
Very good: almost no pollution can be seen
O: slight contamination can be seen
X: apparent accumulation of pollution
The tension fluctuation value was calculated by the following equation.
Tension fluctuation value (g) after 4 hours of yarn running-initial tension (g)
Further, from the tension fluctuation value, the tension fluctuation was evaluated by the following criteria.
Very good: 0g to less than 30g
O: more than 30g and less than 50g
X: 50g or more
The soiled wiping properties of the struts were evaluated by the following methods.
The solution of sodium hydroxide dissolved in water and glycerol was dipped into gauze and the stain produced on the satin chromium support was wiped off. The wiping properties were evaluated based on the number of times required until wiping off.
Very good: can be wiped off less than 5 times
O: wiping for 5 times or more and less than 20 times can remove contamination
X: wiping for more than 20 times without wiping
(sulfate ion (SO)4 2-) Chloride ion (Cl)-) Phosphate radical ion (PO)4 3-) Method of measuring (1)
5g of a sample (nonvolatile component of a treating agent) was accurately weighed, 95g of ultrapure water was added thereto in small amounts while stirring to prepare an aqueous solution, and the volume was determined with a 100ml volumetric flask. 2ml of the prepared aqueous solution was passed through an ODS (octadecylsilyl) pretreatment column to removeThe liquid without lipophilic substances is used for ion chromatographic analysis. Detection was performed under the following ion chromatography conditions. The detected amount was measured by the peak area ratio to a standard solution of known concentration, and the sulfate ion (SO) was converted4 2-) Phosphate radical ion (PO)4 3-) Chloride ion (Cl)-) The amount of (c). The detection limit (determination limit) is sulfate ion (SO)4 2-) Less than 0.6ppm, chloride ion (Cl)-) Less than 1.0ppm, phosphate radical ion (PO)4 3-) Is 0.3ppm or less. In tables 1 and 2,. indicates detection limits or less.
< ion chromatography conditions >
The device comprises the following steps: dionex manufacture ICS-1500 use inhibitor
And (3) analyzing the column: dionex IonPac AS14 inner diameter 4.0mm x length 50mm
Protection of the column: dionex IonPac AG14 inner diameter 4.0mm X length 250mm
Eluent: 3.5mmol Na2CO3、1.0mmol NaHCO3
Flow rate: 1.5ml/min
The numbers of the nonvolatile compositions of the treating agents in tables 1 and 2 indicate the weight ratio of each component (raw material Z is the nonvolatile component) to the nonvolatile component of the treating agent. The details of the treating agent components in tables 1 and 2 are shown below.
< smoothing component (A) >)
A-1: palm oil (ester of glycerol with C12-18 straight chain fatty acid)
A-2: trimethylolpropane tripalmitin fatty acid (C12-18 straight chain fatty acid) ester
A-3: glycerol trioleate
A-4: 2-Ethyl hexyl alcohol stearate
A-5: di-isocetyl thiodipropionate
A-6: dioleyl thiodipropionate
< organic sulfonic acid Compound (B1), (B2) >)
B1-1: a compound (mixture) in which a + b has a value of 10 to 14 and M is Na in the general formula (1)
B1-2: a compound (mixture) in which a + b has a value of 9 to 13 and M is Na in the general formula (1)
B2-1: a compound (mixture) in which c + d + e has a value of 8 to 12 and M is Na in the general formula (2)
B2-2: a compound (mixture) of the general formula (2) wherein c + d + e is 7 to 11 and M is Na
< nonionic surfactant (D) >)
D-1: nonionic surfactant having EO 20 mol added to 1 mol of hydrogenated castor oil
D-2: esterified product of ether-type nonionic surfactant having EO 25 mol added to 1 mol of hydrogenated castor oil and 3 mol of stearic acid
D-3: esterified product of ether-type nonionic surfactant having EO 20 mol added to 1 mol of hydrogenated castor oil and 3 mol of oleic acid
D-4: esterified product of polyethylene glycol (molecular weight 600) and oleic acid 2 mol
D-5: esterified product of polyethylene glycol (molecular weight 200) and oleic acid 2 mol
D-6: ether type nonionic surfactant obtained by adding EO7 mol to 1 mol of lauryl alcohol
D-7: sorbitan monooleate
D-8: oleate of condensate of hydrogenated castor oil ether and maleic acid
< other surfactants >
E-1: POE (10) stearyl amino ether
E-2: POE (3) lauryl amino ether
E-3: dioctyl sulfosuccinate Na salt
E-4: oleic acid K salt
[ production of raw materials Z-1 to Z-6 containing organic phosphate Compound (C) ]
(preparation of raw Material Z-1)
820 parts of isocetyl alcohol were put into a reaction vessel, and 180 parts of phosphorus pentoxide were put into the reaction vessel in small amounts while keeping the reaction temperature at 60. + -. 5 ℃ with stirring. Thereafter, the mixture was aged at 75. + -. 5 ℃ for 3 hours to prepare a raw material Z-1 containing an organic phosphate compound (C) having a nonvolatile content of 100%.
The P-nuclear integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 33.05%, 29.81%, 33.82%, 2.76%, 0.56%, respectively.
(preparation of raw Material Z-2)
800 parts of a C11-15 alcohol is charged into a reactor, and 200 parts of phosphorus pentoxide are added in small amounts at 60. + -. 5 ℃ while taking care of the reaction temperature. Thereafter, the reaction mixture was aged at 75. + -. 5 ℃ for 3 hours to prepare a raw material Z-2 containing the organic phosphate compound (C).
The P-core integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 44.23%, 40.31%, 13.79%, 1.09%, and 0.58%, respectively.
(preparation of raw Material Z-3)
997 parts of the raw material Z-2 thus prepared was charged with 3 parts of ion-exchanged water, and the mixture was treated with water at 90 ℃ for 3 hours. Thereafter, dehydration treatment was carried out at 115 ℃ for 3 hours to prepare a raw material Z-3 containing an organic phosphate compound (C).
The P-nuclear integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 56.72%, 40.49%, 0.00%, 2.78%, respectively.
(preparation of raw Material Z-4)
600 parts of oleyl alcohol was charged into the reaction vessel, and 110 parts of phosphorus pentoxide were added in small amounts at 70. + -. 5 ℃ while keeping the reaction temperature. Thereafter, the reaction mixture was aged at 75. + -. 5 ℃ for 3 hours to prepare a raw material Z-4 containing the organic phosphate compound (C).
The P-core integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 57.65%, 35.26%, 4.57%, 0.44%, and 2.07%, respectively.
(preparation of raw Material Z-5)
600 parts of oleyl alcohol was charged into a reaction vessel, and 110 parts of phosphorus pentoxide were added in small amounts at 70. + -. 5 ℃ while keeping the reaction temperature. Thereafter, the mixture was aged at 70. + -. 5 ℃ for 3 hours. Then, 15 parts of ion-exchanged water was added, water treatment was performed at 90 ℃ for 3 hours, and then 200 parts of dibutylethanolamine was gradually added to neutralize the water, thereby preparing a raw material Z-5 containing an organophosphate compound (C).
The P-core integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 55.18%, 35.38%, 2.43%, 0.00%, and 7.01%, respectively.
(preparation of raw Material Z-6)
970 parts of the raw material Z-1 prepared above was charged with 30 parts of ion-exchanged water, and water treatment was performed at 90 ℃ for 3 hours. Thereafter, dehydration treatment was carried out at 115 ℃ for 3 hours to prepare a raw material Z-3 containing an organic phosphate compound (C).
The P-nuclear integral ratios of the organic phosphate compound (C1), (C2), (C3), (C4), and the inorganic phosphoric acid were 65.43%, 31.74%, 0.00%, 2.83%, respectively.
The organic phosphate compound (C1), (C2), (C3) and (C4) were used in a ratio of nuclear integration to inorganic phosphoric acid P31P-NMR was calculated by the following method.
The nonvolatile content of the measurement sample was weighed at about 30mg in a test tube for NMR having a diameter of 5mm, and about 0.5ml of heavy water (D) was added as a deuterated solvent2O), dissolving it, and using31The measurement was carried out by a P-NMR measuring apparatus (AVANCE 400, 162MHz, manufactured by BRUKER Co.).
[ Table 1]
Figure BDA0002896528430000371
[ Table 2]
Figure BDA0002896528430000381
As is clear from tables 1 and 2, in the examples, the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2) were used, and therefore, the stain accumulation property of the strut was hardly observed, and the wiping property was excellent. That is, the roll contamination during the production of synthetic fibers can be reduced, the roll cleaning interval can be made longer, and the number of times of cleaning can be reduced. Further, the tension fluctuation is extremely small, and fluff and yarn breakage can be greatly reduced.
On the other hand, in the comparative example, the organic sulfonic acid compound (B1) and the organic sulfonic acid compound (B2) were not used in the treatment agent, and therefore, the amount of the stain accumulated on the struts was large, and the wiping property was not good. Further, the tension fluctuation value was extremely large, and the number of fuzz and yarn breakage was large.
Industrial applicability
The synthetic fiber treating agent of the present invention is suitable for use in synthetic fiber filament yarns used for industrial materials such as tarpaulins, tire cords, safety belts, airbags, fishing nets, ropes, slings, and the like, clothing such as fabrics or knits, and the like.

Claims (23)

1. A synthetic fiber treatment agent comprising a smoothing component A, an organic sulfonic acid compound B1 represented by the following general formula (1), and an organic sulfonic acid compound B2 represented by the following general formula (2),
the synthetic fiber treating agent also contains an organic phosphate compound C,
the organic phosphate ester compound C is contained in an amount of 0.05 to 10% by weight based on the nonvolatile component of the treating agent,
phosphate ion (PO) detected from nonvolatile components of treating agent by ion chromatography4 3-) The weight ratio of (A) is 300ppm or less,
the weight ratio of the organic sulfonic acid compound B1 to the organic sulfonic acid compound B2, B1/B2, is 50/50-99/1, wherein the weight ratio of B1/B2 is not 50/50, 70/30, 80/20, 98/2 or 99/1,
[ solution 1]
Figure FDA0002896528420000011
In the formula (1), a and b are integers of 0 or more and satisfy a + b being 5 to 17; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 2]
Figure FDA0002896528420000012
In the formula (2), c, d and e are integers not less than 0 and satisfying c + d + e as 4 to 16; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.
2. The treating agent according to claim 1,
the smoothing component A accounts for 20-70 wt% of the nonvolatile components of the treating agent.
3. The treating agent according to claim 1 or 2, wherein,
the organic phosphate ester compound C is at least 1 selected from the group consisting of a compound represented by the following general formula (4) and a compound represented by the following general formula (5),
[ solution 3]
Figure FDA0002896528420000021
In the formula (4), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; n is an integer of 1-2; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 4]
Figure FDA0002896528420000022
In the formula (5), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group; q1Is M1Or R3O(A1O)m(ii) a Y is 1 or 2.
4. The treating agent according to claim 1 or 2, wherein,
the synthetic fiber treating agent also contains a nonionic surfactant D.
5. A synthetic fiber treatment agent comprising a smoothing component A, an organic sulfonic acid compound B1 represented by the following general formula (1), and an organic sulfonic acid compound B2 represented by the following general formula (2),
the synthetic fiber treating agent also contains an organic phosphate compound C,
the organic phosphate ester compound C is contained in an amount of 0.05 to 10% by weight based on the nonvolatile component of the treating agent,
phosphate ion (PO) detected from nonvolatile components of treating agent by ion chromatography4 3-) The weight ratio of (A) is 300ppm or less,
the total weight ratio of the organic sulfonic acid compound B1 and the organic sulfonic acid compound B2 not included in the nonvolatile components of the treating agent is in the range of 1.26% by weight or more,
[ solution 1]
Figure FDA0002896528420000031
In the formula (1), a and b are integers of 0 or more and satisfy a + b being 5 to 17; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 2]
Figure FDA0002896528420000032
In the formula (2), c, d and e are integers not less than 0 and satisfying c + d + e as 4 to 16; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.
6. The treating agent according to claim 5,
the total weight ratio of the organic sulfonic acid compound B1 and the organic sulfonic acid compound B2 in the nonvolatile components of the treating agent is 0.5 to 7 wt%,
the organic sulfonic acid compound B2 is contained in an amount of 0.015 to 3.5 wt% based on the nonvolatile content of the treating agent.
7. The treating agent according to claim 5 or 6,
the smoothing component A accounts for 20-70 wt% of the nonvolatile components of the treating agent.
8. The treating agent according to claim 5 or 6,
the weight ratio B1/B2 of the organic sulfonic acid compound B1 to the organic sulfonic acid compound B2 is 50/50-99/1.
9. The treating agent according to claim 5 or 6,
the organic phosphate ester compound C is at least 1 selected from the group consisting of a compound represented by the following general formula (4) and a compound represented by the following general formula (5),
[ solution 3]
Figure FDA0002896528420000041
In the formula (4), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; n is an integer of 1-2; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 4]
Figure FDA0002896528420000042
In the formula (5), R3Is the number of carbon atoms6-24 alkyl; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group; q1Is M1Or R3O(A1O)m(ii) a Y is 1 or 2.
10. The treating agent according to claim 5 or 6,
the synthetic fiber treating agent also contains a nonionic surfactant D.
11. A synthetic fiber treatment agent comprising a smoothing component A, an organic sulfonic acid compound B1 represented by the following general formula (1), and an organic sulfonic acid compound B2 represented by the following general formula (2),
the synthetic fiber treating agent also contains an organic phosphate compound C,
the organic phosphate ester compound C is contained in an amount of 0.05 to 10% by weight based on the nonvolatile component of the treating agent,
phosphate ion (PO) detected from nonvolatile components of treating agent by ion chromatography4 3-) The weight ratio of (A) is 300ppm or less,
chloride ion (Cl) detected from nonvolatile components of the treating agent by ion chromatography-) Is 300ppm or less, wherein chlorine ions (Cl) are not contained-) When the weight ratio of (B) is 200ppm or less,
[ solution 1]
Figure FDA0002896528420000051
In the formula (1), a and b are integers of 0 or more and satisfy a + b being 5 to 17; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 2]
Figure FDA0002896528420000052
In the formula (2), c, d and e are integers not less than 0 and satisfying c + d + e as 4 to 16; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.
12. The treating agent according to claim 11,
the total weight ratio of the organic sulfonic acid compound B1 and the organic sulfonic acid compound B2 in the nonvolatile components of the treating agent is 0.5 to 7 wt%,
the organic sulfonic acid compound B2 is contained in an amount of 0.015 to 3.5 wt% based on the nonvolatile content of the treating agent.
13. The treating agent according to claim 11 or 12, wherein,
the smoothing component A accounts for 20-70 wt% of the nonvolatile components of the treating agent.
14. The treating agent according to claim 11 or 12, wherein,
the weight ratio B1/B2 of the organic sulfonic acid compound B1 to the organic sulfonic acid compound B2 is 50/50-99/1.
15. The treating agent according to claim 11 or 12, wherein,
the organic phosphate ester compound C is at least 1 selected from the group consisting of a compound represented by the following general formula (4) and a compound represented by the following general formula (5),
[ solution 3]
Figure FDA0002896528420000061
In the formula (4), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; n is an integer of 1-2; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 4]
Figure FDA0002896528420000062
In the formula (5), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group; q1Is M1Or R3O(A1O)m(ii) a Y is 1 or 2.
16. The treating agent according to claim 11 or 12, wherein,
the synthetic fiber treating agent also contains a nonionic surfactant D.
17. A synthetic fiber treatment agent comprising a smoothing component A, an organic sulfonic acid compound B1 represented by the following general formula (1), and an organic sulfonic acid compound B2 represented by the following general formula (2),
the synthetic fiber treating agent also contains an organic phosphate compound C,
the organic phosphate ester compound C is contained in an amount of 0.05 to 10% by weight based on the nonvolatile component of the treating agent,
phosphate ion (PO) detected from nonvolatile components of treating agent by ion chromatography4 3-) The weight ratio of (A) is 300ppm or less,
the weight ratio B1/B2 of the organic sulfonic acid compound B1 to the organic sulfonic acid compound B2 is 80/20-98/2,
the total weight ratio of the organic sulfonic acid compound B1 and the organic sulfonic acid compound B2 in the nonvolatile components of the treating agent is 2.5-6 wt%,
[ solution 1]
Figure FDA0002896528420000071
In the formula (1), a and b are integers of 0 or more and satisfy a + b being 5 to 17; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 2]
Figure FDA0002896528420000072
In the formula (2), c, d and e are integers not less than 0 and satisfying c + d + e as 4 to 16; m is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group.
18. The treating agent according to claim 17,
the smoothing component A accounts for 20-70 wt% of the nonvolatile components of the treating agent.
19. The treating agent according to claim 17 or 18,
the organic phosphate ester compound C is at least 1 selected from the group consisting of a compound represented by the following general formula (4) and a compound represented by the following general formula (5),
[ solution 3]
Figure FDA0002896528420000081
In the formula (4), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; n is an integer of 1-2; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group,
[ solution 4]
Figure FDA0002896528420000082
In the formula (5), R3Is a hydrocarbon group having 6 to 24 carbon atoms; a. the1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an integer of 0 to 15; m1Is a hydrogen atom, an alkali metal, an ammonium group, or an organic amine group; q1Is M1Or R3O(A1O)m(ii) a Y is 1 or 2.
20. The treating agent according to claim 17 or 18,
the synthetic fiber treating agent also contains a nonionic surfactant D.
21. A synthetic fiber filament yarn obtained by applying the treating agent according to any one of claims 1 to 20 to a raw material synthetic fiber filament yarn.
22. A process for producing a synthetic fiber filament yarn, comprising the step of applying the treating agent according to any one of claims 1 to 20 to a raw synthetic fiber filament yarn.
23. A fibrous structure comprising the synthetic fiber filament yarn of claim 21 and/or obtained by the manufacturing method of claim 22.
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