WO2022215571A1 - 合成繊維用処理剤及び合成繊維 - Google Patents
合成繊維用処理剤及び合成繊維 Download PDFInfo
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- WO2022215571A1 WO2022215571A1 PCT/JP2022/014890 JP2022014890W WO2022215571A1 WO 2022215571 A1 WO2022215571 A1 WO 2022215571A1 JP 2022014890 W JP2022014890 W JP 2022014890W WO 2022215571 A1 WO2022215571 A1 WO 2022215571A1
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- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- HSJXWMZKBLUOLQ-UHFFFAOYSA-M potassium;2-dodecylbenzenesulfonate Chemical compound [K+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HSJXWMZKBLUOLQ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- ZTUXEFFFLOVXQE-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCC(O)=O ZTUXEFFFLOVXQE-UHFFFAOYSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- WFIYFFUAOQKJJS-UHFFFAOYSA-N tetraoctylphosphanium Chemical compound CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC WFIYFFUAOQKJJS-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QCLVFLIIJODTJU-UHFFFAOYSA-N triethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](CC)(CC)CC QCLVFLIIJODTJU-UHFFFAOYSA-N 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
- D06M13/144—Alcohols; Metal alcoholates
-
- 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
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
-
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/30—Flame or heat resistance, fire retardancy properties
Definitions
- the present invention relates to a synthetic fiber treatment agent containing a predetermined phosphate ester compound, etc., and a synthetic fiber to which such a synthetic fiber treatment agent is attached.
- a treatment is sometimes performed to attach a synthetic fiber treatment agent to the surface of the synthetic fibers.
- Patent Document 1 discloses a treatment agent for synthetic fibers containing a predetermined phosphoric acid ester or its organic amine salt, a nonionic surfactant, etc. as a smoothing agent.
- Patent Document 2 discloses a treatment agent for synthetic fibers containing a predetermined organic sulfonic acid compound, an organic phosphoric acid ester compound, a nonionic surfactant, and the like.
- the inventors of the present invention conducted research to solve the above-mentioned problems, and found that a composition containing a smoothing agent, a nonionic surfactant, an alcohol compound, and a specific phosphate ester compound is suitable for a synthetic fiber treatment agent. I found out.
- the synthetic fiber treatment agent of one aspect of the present invention includes a smoothing agent (A), a nonionic surfactant (B), and an ionic surfactant containing the following phosphate ester compound (C1) (C), and containing an alcohol compound (D).
- the phosphate ester compound (C1) includes a phosphate ester P1 represented by the following chemical formula (1), a phosphate ester P2 represented by the following chemical formula (2), and a phosphate ester P3 represented by the following chemical formula (3). , and at least one selected from the phosphate ester P4 represented by the following chemical formula (4), belonging to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the P-nuclear NMR integral ratio attributed to the phosphoric acid ester P1 is 7% or less when the total P-nuclear NMR integral ratio is 100%.
- R 1 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms in total.
- m is an integer of 2 or 3;
- R 2 and R 3 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- R 4 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms in total.
- R 5 and R 6 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- the phosphate ester compound (C1) contains the phosphate ester P2, and the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the P-nuclear NMR integral ratio attributed to the phosphoric acid ester P2 may be 5% or more and 50% or less when the total of the P-nuclear NMR integral ratios attributed is 100%.
- the phosphate ester compound (C1) contains the phosphate ester P2, and the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the total P-nuclear NMR integral ratio attributed is 100%
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is 5% or less
- the P-nuclear NMR integral ratio attributed to the phosphate ester P2 The ratio may be 10% or more and 45% or less.
- the alcohol compound (D) may contain at least one selected from monohydric alcohols and diols. In the synthetic fiber treatment agent, even if the alcohol compound (D) contains a monohydric alcohol and the content of the monohydric alcohol in the synthetic fiber treatment agent is 0.0001% by mass or more and 3% by mass or less good.
- the alcohol compound (D) may contain a diol, and the content of the diol in the synthetic fiber treatment agent may be 0.001% by mass or more and 5% by mass or less.
- the smoothing agent (A) contains at least one selected from the following complete ester compound (A1), the sulfur-containing ester compound (A2), and the following partial ester compound (A3). can be anything.
- the complete ester compound (A1) is a complete ester compound of a polyhydric alcohol having a chain structure having 3 to 6 carbon atoms and a monovalent fatty acid having 8 to 24 carbon atoms and a monovalent monovalent having 8 to 24 carbon atoms. It is at least one selected from complete ester compounds of alcohols and polyvalent fatty acids having 3 to 10 carbon atoms.
- the partial ester compound (A3) is a partial ester compound of a polyhydric alcohol having a chain structure of 3 or more and 6 or less carbon atoms and a monovalent fatty acid of 8 or more and 24 or less carbon atoms.
- the smoothing agent (A) contains the full ester compound (A1), and the content of the full ester compound (A1) in the synthetic fiber treatment agent is 30% by mass or more and 70% by mass. % or less.
- the smoothing agent (A) may contain the sulfur-containing ester compound (A2).
- the smoothing agent (A) may contain the partial ester compound (A3).
- the concentration of phosphate ions detected from the synthetic fiber treatment agent by ion chromatography may be 200 ppm or less.
- the gist of a synthetic fiber according to another aspect of the present invention is that the synthetic fiber treatment agent is adhered thereto.
- the processing agent of the present embodiment contains a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) containing a phosphate ester compound (C1), and an alcohol compound (D).
- the treatment agent is preferably used for treating synthetic fibers other than acrylic fibers for carbon fiber production, unlike the acrylic fiber treatment agent for carbon fiber production disclosed in, for example, WO 2013/129115.
- smoothing agent (A) examples include silicone oil, mineral oil, polyolefin, ester oil and the like.
- the smoothing agent (A) imparts smoothness to the synthetic fibers.
- silicone oils are not particularly limited, but include dimethylsilicone, phenyl-modified silicone, amino-modified silicone, amide-modified silicone, polyether-modified silicone, aminopolyether-modified silicone, alkyl-modified silicone, alkylaralkyl-modified silicone, Alkylpolyether-modified silicone, ester-modified silicone, epoxy-modified silicone, carbinol-modified silicone, mercapto-modified silicone, polyoxyalkylene-modified silicone and the like can be mentioned. Commercially available products can be appropriately used as these silicone oils.
- mineral oils examples include aromatic hydrocarbons, paraffinic hydrocarbons, naphthenic hydrocarbons, and the like. More specific examples include spindle oil and liquid paraffin. Commercially available products can be appropriately used as these mineral oils. A mineral oil having a kinematic viscosity of 5 mm 2 /s or more at 40° C. is used.
- poly- ⁇ -olefin used as a smoothing component is applied.
- polyolefins include poly- ⁇ -olefins obtained by polymerizing 1-butene, 1-hexene, 1-decene, and the like. Commercially available poly- ⁇ -olefins can be used as appropriate.
- the ester oil is not particularly limited, but includes an ester oil produced from fatty acid and alcohol.
- ester oils include ester oils produced from fatty acids and alcohols having an odd or even number of hydrocarbon groups, which will be described later.
- Fatty acids which are raw materials for ester oils, are not particularly limited in terms of the number of carbon atoms, the presence or absence of branching, the valence, and the like.
- a fatty acid having a ring may also be used.
- There are no particular restrictions on the number of carbon atoms, the presence or absence of branching, the valence, etc. of the alcohol, which is the raw material of the ester oil. may be an alcohol having
- the ester oil preferably contains at least one selected from the complete ester compound (A1), the sulfur-containing ester compound (A2), and the partial ester compound (A3). Moreover, it is more preferable that the ester oil contains a sulfur-containing ester compound (A2). With such a configuration, it is possible to suppress tension fluctuations by improving heat resistance. Further, the ester oil more preferably contains the following partial ester compound (A3). With such a configuration, tar can be suppressed by improving compatibility.
- the complete ester compound (A1) is a complete ester compound of a polyhydric alcohol having a chain structure having 3 to 6 carbon atoms and a monovalent fatty acid having 8 to 24 carbon atoms and a monovalent monovalent having 8 to 24 carbon atoms. It is at least one selected from complete ester compounds of alcohols and polyvalent fatty acids having 3 to 10 carbon atoms. However, a dibasic acid containing a sulfur atom in the molecule such as thiodipropionic acid or dithiodipropionic acid is not included in the polyvalent fatty acid in the ester compound (A1).
- the partial ester compound (A3) is a partial ester compound of a polyhydric alcohol having a chain structure of 3 or more and 6 or less carbon atoms and a monovalent fatty acid of 8 or more and 24 or less carbon atoms.
- Polyhydric alcohols having a chain structure include polyhydric alcohols having no cyclic structure, and the chain structure may be linear or branched. .
- Specific examples of polyhydric alcohols having a chain structure with 3 to 6 carbon atoms include glycerin, diglycerin, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane, butanetriol, pentanetriol, and hexanetriol. mentioned.
- the monovalent fatty acid having 8 or more and 24 or less carbon atoms a known fatty acid can be appropriately adopted, and it may be a saturated fatty acid or an unsaturated fatty acid. Moreover, it may be linear or may have a branched chain structure. Specific examples of the above saturated fatty acids include octanoic acid (caprylic acid), nonanoic acid, decanoic acid (capric acid), dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecane.
- unsaturated fatty acids include myristoleic acid, palmitoleic acid, oleic acid, vaccenic acid, eicosenoic acid, linoleic acid, ⁇ -linolenic acid, ⁇ -linolenic acid, and arachidonic acid.
- the monohydric alcohol having 8 or more and 24 or less carbon atoms a known one can be appropriately adopted, and it may be a saturated aliphatic monohydric alcohol or an unsaturated aliphatic monohydric alcohol. Moreover, it may be linear or may have a branched chain structure. Specific examples of monohydric alcohols having 8 to 24 carbon atoms include octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, and nonadecanol.
- eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol and other linear alkyl alcohols isooctanol, isononanol, isodecanol, isododecanol, isotridecanol, isotetradecanol, isotriacontanol, isohexa Branched alkyl alcohols such as decanol, isoheptadecanol, isooctadecanol, isononadecanol, isoeicosanol, isoheneicosanol, isodocosanol, isotrichosanol, and isotetracosanol, tetradecenol, straight-chain alkenyl alcohols such as hexadecenol, heptadecenol, octade,
- polyvalent fatty acid having 3 or more and 10 or less carbon atoms a known one can be appropriately adopted, and it may be a saturated fatty acid, an unsaturated fatty acid, or an aromatic carboxylic acid.
- polyvalent fatty acids having 3 to 10 carbon atoms include aliphatic carboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid and aconitic acid, terephthalic acid, isophthalic acid, aromatic carboxylic acids such as trimellitic acid;
- complete ester compound (A1) examples include trimethylolpropane trioleate, diisostearyl adipate, coconut oil, rapeseed oil, sunflower oil, soybean oil, castor oil, sesame oil, palm oil, fish oil, beef tallow, and the like. and natural oils and fats.
- sulfur-containing ester compound (A2) examples include dioctylthiodipropionate, diisolaurylthiodipropionate, dilaurylthiodipropionate, diisocetylthiodipropionate, and diisostearylthiodipropionate.
- dioleyl thiodipropionate dioleyl thiodipropionate, octyl thiodipropionate, isolauryl thiodipropionate, lauryl thiodipropionate, isocetyl thiodipropionate, isostearyl thiodipropionate, oleyl thiodipropionate, octyl mercaptopropionate pionate, stearyl mercaptopropionate, trimethylolpropane tris (mercaptopropionate), dioctyldithiodipropionate and the like.
- partial ester compound (A3) examples include trimethylolpropane monooleate, glycerin monooleate, diglycerin dilaurate, trimethylolpropane dioleate, glycerin dioleate, and the like.
- the lower limit of the content of the complete ester compound (A1) in the treatment agent is appropriately selected, but is preferably 30% by mass or more, more preferably 35% by mass or more.
- the upper limit of the content is appropriately selected, but is preferably 70% by mass or less, more preferably 65% by mass or less. Ranges with any combination of the above upper and lower limits are also envisioned. The effect of the present invention can be further improved by being defined within such a range.
- ester oil other than the ester oil described above may be used.
- ester oils include (1) aliphatic monoalcohols and aliphatic monocarboxylic acids such as octyl palmitate, oleyl laurate, oleyl oleate, isotridecyl stearate, and isotetracosyl oleate; and (2) ester compounds of aromatic alcohols and aliphatic carboxylic acids such as benzyl oleate, benzyl laurate and bisphenol A dilaurate.
- Nonionic surfactants (B) include, for example, alcohols or carboxylic acids to which alkylene oxides are added, ether-ester compounds obtained by adding alkylene oxides to ester compounds of carboxylic acids and polyhydric alcohols, and amine compounds. Examples thereof include alkylamines to which alkylene oxide is added, partial ester compounds of carboxylic acids and polyhydric alcohols having a cyclic structure having 3 to 6 carbon atoms, and the like. As these nonionic surfactants (B), one type of nonionic surfactant may be used alone, or two or more types of nonionic surfactants may be used in appropriate combination.
- alcohols used as raw materials for the nonionic surfactant (B) include (1) methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, pentacosanol, hexacosanol, heptakosanol, octacosanol, nonacosanol , linear alkyl alcohols such as triacontanol, (2) isopropanol, isobutano
- carboxylic acids used as raw materials for the nonionic surfactant (B) include (1) octylic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, and hexadecane.
- linear alkyl carboxylic acids such as acids, heptadecanoic acid, octadecanoic acid, nonadecanic acid, eicosanoic acid, heneicosanoic acid, and docosanoic acid; (2) 2-ethylhexanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, Branched alkylcarboxylic acids such as isooctadecanic acid, (3) linear alkenylcarboxylic acids such as octadecenoic acid, octadecadienoic acid and octadecatrienoic acid, (4) aromatic carboxylic acids such as benzoic acid, and the like can be mentioned.
- alkylene oxides used as raw materials for nonionic surfactants (B) include ethylene oxide and propylene oxide.
- the number of moles of alkylene oxide to be added is appropriately set, but is preferably 0.1 to 60 mol, more preferably 1 to 40 mol, and still more preferably 2 to 30 mol. Ranges with any combination of the above upper and lower limits are also envisioned.
- the number of moles of alkylene oxide added indicates the number of moles of alkylene oxide per 1 mole of alcohol or carboxylic acid in the starting material. When multiple kinds of alkylene oxides are used, they may be block adducts or random adducts.
- polyhydric alcohols used as raw materials for the nonionic surfactant (B) include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1 ,4-butanediol, 2-methyl-1,2-propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2 ,3-dimethyl-2,3-butanediol, glycerin, 2-methyl-2-hydroxymethyl-1,3-propanediol, trimethylolpropane, sorbitan, pentaerythritol, sorbitol and the like.
- alkylamines used as raw materials for nonionic surfactants (B) include methylamine, ethylamine, butylamine, octylamine, laurylamine, octadecylamine, octadecenylamine, coconut amine, and the like.
- nonionic surfactant (B) examples include, for example, 1 mol of oleyl alcohol with 10 mol of ethylene oxide (hereinafter referred to as EO) added, 1 mol of isotridecanol with 10 mol of EO added, 10 mol of EO and 10 mol of propylene oxide (hereinafter referred to as PO) are randomly added to 1 mol of isotridecanol, 10 mol of EO is added to 1 mol of hydrogenated castor oil, and 20 mol of EO is added to 1 mol of hydrogenated castor oil.
- EO oleyl alcohol with 10 mol of ethylene oxide
- PO propylene oxide
- a compound obtained by adding and then esterifying with 3 mol of oleic acid a compound obtained by adding 25 mol of EO to 1 mol of hydrogenated castor oil, cross-linking with adipic acid, and terminally esterifying with stearic acid (average molecular weight: 5000), sorbitan monooleate Art, sorbitan trioleate, diester of polyethylene glycol (average molecular weight 600) and oleic acid, diester of polyethylene glycol (average molecular weight 400) and lauric acid, monoester of polyethylene glycol (average molecular weight 600) and oleic acid, 1 mol of laurylamine to which 3 mol of EO is added, and 1 mol of laurylamine to which 10 mol of EO is added.
- the content of the nonionic surfactant (B) in the treatment agent is appropriately set, but is preferably 5% by mass or more and 70% by mass or less, more preferably 10% by mass or more and 65% by mass or less, and still more preferably 20% by mass. % or more and 60 mass % or less. Ranges with any combination of the above upper and lower limits are also envisioned. The effect of the present invention can be further improved by being defined within such a numerical range.
- the phosphate ester compound (C1) includes a phosphate ester P1 represented by the following chemical formula (1), a phosphate ester P2 represented by the following chemical formula (2), and a phosphate ester P3 represented by the following chemical formula (3). , and phosphate P4 represented by the following chemical formula (4).
- R 1 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms in total.
- m is an integer of 2 or 3;
- phosphate esters P1 may contain one kind of phosphate ester P1 alone, or may contain two or more kinds of phosphate esters P1.
- the alkyl group constituting R 1 may be a linear alkyl group or an alkyl group having a branched chain structure.
- the alkenyl group constituting R 1 may be a straight-chain alkenyl group or an alkenyl group having a branched chain structure.
- linear alkyl groups constituting R 1 include octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, icosyl group, docosyl group, tricosyl group, tetracosyl group and the like.
- alkyl group having a branched chain structure constituting R 1 examples include isooctyl group, isononyl group, isodecyl group, isoundecyl group, isododecyl group, isotridecyl group, isotetradecyl group, isopentadecyl group, and isohexadecyl. group, isoheptadecyl group, isooctadecyl group, isoicosyl group, isodocosyl group, isotricosyl group, isotetracosyl group and the like.
- linear alkenyl groups constituting R 1 include octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, icosenyl group, docosenyl group, tricosenyl group, tetracosenyl group and the like.
- alkenyl group having a branched chain structure constituting R 1 examples include isooctenyl group, isononenyl group, isodecenyl group, isoundecenyl group, isododecenyl group, isotridecenyl group, isotetradecenyl group, and isopentadecenyl group. , isohexadecenyl group, isoheptadecenyl group, isooctadecenyl group, isoicocenyl group, isodococenyl group, isotricosenyl group, isotetracosenyl group and the like.
- 1 mol or more and 20 mol or less of an alkylene oxide having 2 or more and 3 or less carbon atoms is added to 1 mol of an aliphatic alcohol having 8 or more and 24 or less carbon atoms, and the residue obtained by removing the hydroxyl group has 8 or more and 24 carbon atoms.
- Specific examples of the following aliphatic alcohols include those of the aliphatic monohydric alcohols exemplified above as raw materials for the ester oils.
- alkylene oxides include ethylene oxide and propylene oxide.
- the number of moles of alkylene oxide added indicates the number of moles of alkylene oxide per 1 mole of aliphatic alcohol in the starting material.
- alkylene oxides may be block adducts or random adducts.
- Examples include 2-ethylhexanol with 2 mols of EO added, normal octanol with 2 mols of EO and 2 mols of PO added at random, lauryl alcohol with 3 mols of EO added, isolauryl alcohol with 3 mols of EO added.
- 3 mol of EO and 3 mol of PO are randomly added to isolauryl alcohol, 3 mol of EO is added to cetyl alcohol, 3 mol of EO is added to isocetyl alcohol, and 4 mol of EO is added to oleyl alcohol.
- a residue obtained by removing a hydroxyl group from a molar addition or the like can be mentioned.
- M 1 and M 2 each represent a hydrogen atom, alkali metal, alkaline earth metal (1/2), organic amine salt, ammonium, or phosphonium. Since an alkaline earth metal is divalent, "alkaline earth metal ( 1/2 )" means that 1/2 mol is added to M1 or M2. Specific examples of alkali metals include sodium, potassium, and lithium. Specific examples of alkaline earth metals include magnesium and calcium.
- organic amines include (1) methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, NN-diisopropylethylamine, butylamine, dibutylamine, 2-methylbutylamine, tributylamine, octylamine, (2) aromatic amines or heterocyclic amines such as aniline, N-methylbenzylamine, pyridine, morpholine, piperazine, derivatives thereof, (3) monoethanolamine, alkanolamines such as N-methylethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, dibutylethanolamine, butyldiethanolamine, octyldiethanolamine and lauryldiethanolamine; (4) aryls such as 3-aminopropene; (5) polyoxyalkylene alkyl amino ethers such as polyoxyethylene lau
- phosphonium examples include quaternary phosphonium such as tetramethylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetraoctylphosphonium, dibutyldihexylphosphonium, trihexyltetradecylphosphonium, triethyloctylphosphonium, and triphenylmethylphosphonium.
- the phosphate ester P2 is represented by the following chemical formula (2).
- R 2 and R 3 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- the alkyl group constituting R 2 or R 3 may be a straight-chain alkyl group or an alkyl group having a branched chain structure.
- the alkenyl group constituting R 2 or R 3 may be a straight-chain alkenyl group or an alkenyl group having a branched chain structure.
- alkyl group constituting R 2 or R 3 include those exemplified as the alkyl group constituting R 1 in chemical formula (1).
- alkenyl groups constituting R 2 or R 3 include those exemplified as alkenyl groups constituting R 1 in chemical formula (1).
- an alkylene oxide having 2 or more and 3 or less carbon atoms to 1 mol of an aliphatic alcohol having 8 or more and 24 or less carbon atoms, which constitutes R 2 or R 3 , and excluding the hydroxyl group.
- M 3 examples include those exemplified for M 1 or M 2 in chemical formula (1).
- Phosphate ester P3 is represented by the following chemical formula (3).
- R 4 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms. is a residue obtained by removing the hydroxyl group from the one added with 1 mol or more and 20 mol or less, M4 and M5 are each a hydrogen atom, alkali metal, alkaline earth metal (1/2), organic amine salt, ammonium, or phosphonium.
- the alkyl group constituting R 4 may be a linear alkyl group or an alkyl group having a branched chain structure.
- the alkenyl group constituting R 4 may be a straight-chain alkenyl group or an alkenyl group having a branched chain structure.
- alkyl group that constitutes R 4 examples include those exemplified as the alkyl group that constitutes R 1 in chemical formula (1).
- alkenyl groups constituting R 4 include those exemplified as alkenyl groups constituting R 1 in chemical formula (1).
- Specific examples listed for R 1 in the chemical formula (1) can be employed as the.
- M4 or M5 include those exemplified for M1 or M2 in chemical formula ( 1 ).
- Phosphate ester P4 is represented by the following chemical formula (4).
- R 5 and R 6 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- a residue obtained by adding a total of 1 mol or more and 20 mol or less of an alkylene oxide of and excluding a hydroxyl group, M6 is a hydrogen atom, alkali metal, alkaline earth metal (1/2), organic amine salt, ammonium, or phosphonium.
- phosphate esters P4 one kind of phosphate ester P4 may be used alone, or two or more kinds of phosphate esters P4 may be used in combination as appropriate.
- the alkyl group constituting R 5 or R 6 may be a linear alkyl group or an alkyl group having a branched chain structure.
- the alkenyl group constituting R 5 or R 6 may be a straight-chain alkenyl group or an alkenyl group having a branched chain structure.
- alkyl group constituting R 5 or R 6 include those exemplified as the alkyl group constituting R 1 in chemical formula (1).
- alkenyl groups constituting R 5 or R 6 include those exemplified as alkenyl groups constituting R 1 in chemical formula (1).
- an alkylene oxide having 2 to 3 carbon atoms to 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms that constitutes R 5 or R 6 and removing the hydroxyl group.
- M6 include those exemplified for M1 or M2 in chemical formula ( 1 ).
- the phosphate ester compound (C1) is attributed to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4 in the P-nuclear NMR measurement when pretreated with alkali overneutralization.
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is 7% or less.
- alkaline overneutralization pretreatment means a pretreatment in which an excess amount of alkali is added to the alkyl phosphate compound.
- alkali include, but are not limited to, organic amines, hydroxides of alkali metals and alkaline earth metals. Moreover, it may be the same as or different from the alkali used when synthesizing the phosphate ester salt.
- organic amine include those exemplified for the organic amine constituting the phosphoric acid ester salt described above.
- hydroxides of alkali metals or alkaline earth metals include sodium hydroxide, potassium hydroxide, magnesium hydroxide and the like.
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is given by the following formula (1).
- the P-nuclear NMR integral ratio attributed to the phosphate ester P2 is given by the following formula (2).
- the P-nuclear NMR integral ratio attributed to the phosphate ester P3 is given by the following formula (3).
- the P-nuclear NMR integral ratio attributed to the phosphate ester P4 is given by the following formula (4).
- P1_P% is the P nuclear NMR integral ratio attributed to the phosphate ester P1;
- P1_P is the P nuclear NMR integral value assigned to the phosphate ester P1;
- P2_P is the P nuclear NMR integral value assigned to the phosphate ester P2;
- P3_P is the P nuclear NMR integral value assigned to the phosphate ester P3;
- P4_P represents the P nuclear NMR integral value assigned to the phosphate ester P4.
- P2_P% is the P nuclear NMR integral ratio attributed to the phosphate ester P2;
- P1_P is the P nuclear NMR integral value assigned to the phosphate ester P1;
- P2_P is the P nuclear NMR integral value assigned to the phosphate ester P2;
- P3_P is the P nuclear NMR integral value assigned to the phosphate ester P3;
- P4_P represents the P nuclear NMR integral value assigned to the phosphate ester P4.
- P3_P% is the P nuclear NMR integral ratio attributed to the phosphate ester P3;
- P1_P is the P nuclear NMR integral value assigned to the phosphate ester P1;
- P2_P is the P nuclear NMR integral value assigned to the phosphate ester P2;
- P3_P is the P nuclear NMR integral value assigned to the phosphate ester P3;
- P4_P represents the P nuclear NMR integral value assigned to the phosphate ester P4.
- P4_P% is the P nuclear NMR integral ratio attributed to the phosphate ester P4;
- P1_P is the P nuclear NMR integral value assigned to the phosphate ester P1;
- P2_P is the P nuclear NMR integral value assigned to the phosphate ester P2;
- P3_P is the P nuclear NMR integral value assigned to the phosphate ester P3;
- P4_P represents the P nuclear NMR integral value assigned to the phosphate ester P4.
- the P-nuclear NMR integral ratio attributed to the phosphoric acid ester P2 is preferably 5% or more and 50% or less.
- the phosphate ester compound (C1) contains the phosphate ester P2, the P nuclear NMR integral attributed to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the total ratio is 100%
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is 5% or less
- the P-nuclear NMR integral ratio attributed to the phosphate ester P2 is 10% or more and 45%.
- the following are preferable. By defining such a range, the effects of the present invention can be further improved.
- the phosphate ester compound (C1) contains the phosphate ester P2, the P nuclear NMR integral attributed to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the total ratio is 100%
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is 5% or less
- the P-nuclear NMR integral ratio attributed to the phosphate ester P2 is 15% or more and 40%.
- the following are more preferable.
- the phosphate ester compound (C1) is obtained by reacting a saturated aliphatic alcohol or an unsaturated aliphatic alcohol having 8 to 24 carbon atoms as a raw material alcohol with, for example, diphosphorus pentoxide to obtain an alkyl phosphate ester, and then can be obtained by neutralizing or overneutralizing an alkyl phosphate with an alkali such as potassium hydroxide or an amine.
- the phosphate ester compound is usually a phosphate ester P1 represented by the chemical formula (1), a phosphate ester P2 represented by the chemical formula (2), a phosphate ester P3 represented by the chemical formula (3), and phosphate ester P4 represented by the chemical formula (4).
- phosphate ester P1 is particularly susceptible to decomposition during storage, and inorganic phosphoric acid and salts thereof are easily produced. In particular, it occurs remarkably when water is contained in the treating agent. Inorganic phosphoric acid and salts thereof precipitate out of the treatment agent and further reduce the heat resistance of the treatment agent, thus adversely affecting yarn production.
- the raw material is dehydrated before the phosphorylation step, or an inert gas atmosphere is used during the phosphorylation step.
- the content of the phosphate ester P1 may be reduced by adding water to the phosphate ester compound (C1) and heating it to about 100° C. to decompose it.
- inorganic phosphoric acid and its salt are generated by thermal decomposition of the phosphate ester P1.
- Inorganic phosphoric acid and salts thereof are preferably removed from the treatment agent from the viewpoint of improving heat resistance. For their removal, known purification techniques such as adsorption treatment can be applied.
- the phosphate ester compound (C1) includes the phosphate ester P1 represented by the chemical formula (1), the phosphate ester P2 represented by the chemical formula (2), the phosphate ester P3 represented by the chemical formula (3), and the chemical formula ( It may be prepared by mixing phosphate ester P4 shown in 4).
- the content of the phosphate ester compound (C1) in the treatment agent is appropriately set, but is preferably 0.1% by mass or more and 10% by mass or less in a state where a salt is not formed by the neutralizing agent, and 0.1% by mass or more and 10% by mass or less. 3% by mass or more and 5% by mass or less is more preferable. Ranges with any combination of the above upper and lower limits are also envisioned. The effect of the present invention can be further improved by being defined within such a numerical range. Moreover, by defining the amount within such a range, the function of the treatment agent such as antistatic properties can be efficiently exhibited.
- the treatment agent may contain an ionic surfactant (C) other than the phosphate ester compound (C1).
- an ionic surfactant (C) other than the phosphate ester compound (C1) a known one can be appropriately employed.
- Ionic surfactants include anionic surfactants, cationic surfactants, and amphoteric surfactants.
- anionic surfactants include (1) laurylsulfonate, myristylsulfonate, cetylsulfonate, oleylsulfonate, stearylsulfonate, tetradecanesulfonate, ⁇ -olefinsulfonate, Aliphatic sulfonates or aromatic sulfonates such as dodecylbenzene sulfonate and secondary alkyl sulfonate; (2) sulfuric acid of aliphatic alcohols such as lauryl sulfate, oleyl sulfate, and stearyl sulfate; EO and PO to aliphatic alcohols such as ester salts, (3) polyoxyethylene lauryl ether sulfate, polyoxyalkylene (polyoxyethylene, polyoxypropylene) lauryl ether sulfate, and polyoxyethylene oleyl ether sulfate (4) castor oil fatty acid
- the counter ion of the anionic surfactant include alkali metal salts such as potassium salts and sodium salts, ammonium salts, alkanolamine salts such as triethanolamine, and the like.
- cationic surfactants include lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, and didecyldimethylammonium chloride.
- amphoteric surfactants include, for example, betaine type amphoteric surfactants.
- ionic surfactants (C) one type of ionic surfactant may be used alone, or two or more types of ionic surfactants may be used in appropriate combination.
- Alcohol compound (D) The alcohol compound (D) has the effect of further improving the storage stability of the processing agent. It also has the effect of further improving the heat resistance of the treatment agent.
- the alcohol compound (D) include monohydric alcohols and polyhydric alcohols.
- the alcohol compound (D) preferably contains at least one selected from monohydric alcohols and diols. Such a compound suppresses the falling off of deposits of the processing agent on the heating roller, and suppresses the accumulation of tar and the like.
- monohydric alcohols include lower alcohols and higher alcohols.
- examples of higher alcohols include monohydric aliphatic alcohols having 8 to 24 carbon atoms.
- the monohydric alcohol is not particularly limited with respect to the presence or absence of an unsaturated bond, and may be an alcohol having a linear or branched hydrocarbon group, or an alcohol having a cyclo ring. In the case of alcohol having a branched hydrocarbon group, the branching position is not particularly limited. Moreover, it may be a primary alcohol, or a secondary or tertiary alcohol.
- monohydric alcohols include methanol, ethanol, propanol, octyl alcohol, nonanol, decanol, undecanol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetanol, stearyl alcohol, eicosanol, behenyl alcohol, tetracosa alcohol, oleyl alcohol, isopropanol, 2-ethylhexanol, isododecyl alcohol, isotridecyl alcohol, isomyristyl alcohol, isocetanol, isostearyl alcohol, isotetracosanol and the like.
- diols include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,2- propanediol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 2-methyl-2,4-pentanediol, 2,3-dimethyl-2,3-butanediol, diethylene glycol, Examples include polyethylene glycol, dipropylene glycol, polypropylene glycol, and copolymers of polyethylene glycol and polypropylene glycol. As these alcohol compounds (D), one type of alcohol compound may be used alone, or two or more types of alcohol compounds may be used in combination as appropriate. Among these, (poly)alkylene oxides are preferred from the viewpoint of improving stability.
- the content of the monohydric alcohol in the treatment agent is appropriately set, but is preferably 0.0001% by mass or more and 3% by mass or less, and is preferably 0.001% by mass or more and 2.5% by mass or less. More preferably, it is 0.01% by mass or more and 2% by mass or less. Ranges with any combination of the above upper and lower limits are also envisioned. By setting it within this range, the stability is further improved and the accumulation of tar is further suppressed.
- the content of the diol in the treatment agent is appropriately set, but is preferably 0.001% by mass or more and 5% by mass or less, and more preferably 0.01% by mass or more and 4% by mass or less. Ranges with any combination of the above upper and lower limits are also envisioned. By setting it within this range, the stability is further improved and the accumulation of tar is further suppressed.
- the treating agent preferably has a phosphate ion concentration of 200 ppm or less, more preferably 150 ppm or less, detected from the treating agent by ion chromatography. By defining such a range, the accumulation of the processing agent or tar on the heating roller is suppressed.
- the treatment agent of the first embodiment is attached to the synthetic fibers of the present embodiment.
- the treatment agent may be applied in the form of a dilute solution diluted with a diluent solvent, such as a low-viscosity mineral oil solution, an organic solvent solution, or an aqueous solution.
- a diluent solvent such as a low-viscosity mineral oil solution, an organic solvent solution, or an aqueous solution.
- a non-polar solvent such as low-viscosity mineral oil.
- Synthetic fibers are obtained through a step of attaching a dilute solution of a treatment agent such as an aqueous solution to the synthetic fibers in, for example, a spinning or drawing step.
- the diluent adhering to the synthetic fiber may evaporate the diluent solvent through a drawing process and a drying process.
- the effect of the invention can be more expected by using a production facility having a step of passing rollers at 150° C. or higher in the stretching or heat treatment step, or by using it in such a step.
- polyester fibers such as composite fibers containing lactic acid and these polyester resins, (2) polyamide fibers such as nylon 6 and nylon 66, (3) polyacrylic fibers such as polyacryl and modacrylic, (4 ) polyolefin fibers such as polyethylene and polypropylene.
- polyester fibers and polyamide fibers are preferred.
- synthetic fibers other than acrylic fibers for carbon fiber production are preferred.
- the ratio of the treatment agent to be applied to the synthetic fibers there is no particular limitation on the ratio of the treatment agent to be applied to the synthetic fibers, but the treatment agent should be applied at a ratio of 0.1% by mass or more and 3% by mass or less (excluding solvents such as water) to the synthetic fibers. is preferred. Such a configuration can further improve the effects of the present invention.
- the method of applying the treatment agent is not particularly limited, and known methods such as a roller oiling method, a guide oiling method using a metering pump, an immersion oiling method, and a spray oiling method can be employed.
- the processing agent of this embodiment contains a smoothing agent, a nonionic surfactant, an alcohol compound, and a specific phosphate ester compound.
- a smoothing agent e.g., a nonionic surfactant, an alcohol compound, and a specific phosphate ester compound.
- the heat resistance of the processing agent is improved, and the storage stability of the processing agent is improved.
- ordinary additives such as a stabilizer, an antistatic agent, a binder, an antioxidant, an ultraviolet absorber, etc. for maintaining the quality of the processing agent are included within the range that does not impede the effects of the present invention.
- Components used in the treatment agent may be further blended.
- the treatment agent of the above embodiment may further contain water within a range that does not impair the effects of the present invention.
- the content of water is preferably more than 0% by mass and 4% by mass or less from the viewpoint of improving the stability of the treatment agent.
- Test category 1 (synthesis of phosphate ester compound (C1)) Phosphate ester compounds used in the treatment agents of each example and each comparative example were synthesized by the method shown below.
- Phosphate Ester Compound (P-1) Isocetyl alcohol used as a raw material alcohol was dehydrated under reduced pressure at 105°C. A four-necked flask was charged with isocetyl alcohol, diphosphorus pentoxide was gradually added thereto under a nitrogen atmosphere, and the mixture was stirred at 70 ⁇ 5° C. for 3 hours to carry out a phosphorylation reaction. The phosphoric oxide was purified by column chromatography, mixed with dibutylethanolamine as a neutralizing agent, and stirred at 50° C. for 1 hour to synthesize a phosphoric ester compound (P-1).
- Phosphate ester compounds (P-2 to P-6, rP-1, rP-2) Phosphate ester compounds (P-2 to P-6) were synthesized in the same manner as P-1, using raw materials listed in Table 1 as starting alcohols.
- Neutralization of the phosphate ester compound (rP-1) was carried out by adding phosphoric oxide to an aqueous potassium hydroxide solution, stirring the resulting mixture, air-drying the mixture, and applying it to the treating agent.
- Neutralizing agent (alkali) for forming raw material alcohols and salts that constitute the alkyl groups of the phosphate ester compounds (P-1 to P-6, rP-1, rP-2) to be blended in the treatment agent are shown in the "raw material alcohol” column and the “neutralizing agent” column of Table 1, respectively.
- P-Nuclear NMR Measurement Method Pretreatment was performed by adding 0.15 g of laurylamine as an alkali to 0.10 g of each phosphoric acid ester compound (C1) synthesized as described above and stirring the mixture. Then, using 31 P-NMR, each P-nuclear NMR integral value attributed to the phosphate esters P1 to P4 was obtained.
- the measured value of 31 P-NMR (trade name: MERCURY plus NMR Spectrometer System, 300 MHz, manufactured by VALIAN) was used. Deuterated chloroform was used as the solvent.
- the respective P-nuclear NMR integral ratios (%) attributed to the phosphate esters P1 to P4 were obtained.
- the values calculated from the formulas (1) to (4) for each phosphate ester compound (C1) were equal to the P-nuclear NMR integral ratio of the treatment agent containing each phosphate ester compound (C1).
- the P-nuclear NMR integral ratios (%) of the phosphate esters P1 to P4 obtained by the P-nuclear NMR measurement of the phosphate ester compounds are shown in the "P-nuclear NMR integral ratio (%)" column of Table 1, respectively.
- Test category 2 preparation of treatment agent
- the processing agents used in each example and each comparative example were prepared by the following preparation method using each component shown in Tables 2 and 3.
- Example 2 to 18 and Comparative Examples 1 to 4 the smoothing agent (A), the nonionic surfactant (B), the ionic surfactant (C), and the alcohol compound (D) were used in the same manner as in Example 1.
- 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethyl) was used as an antioxidant in addition to the raw materials listed in Table 2.
- Benzyl)isocyanuric acid was added at a rate of 0.8 parts per 100 parts of the treating agent.
- Phosphate ions in the treatment agent were also measured by ion chromatography under the following conditions. The results are shown in the "phosphate ion concentration" column of Tables 2 and 3. 1 g of sample (including volatile matter) was accurately weighed, and a 10% 2-propanol aqueous solution was added little by little while stirring to prepare a constant volume solution in a 100 mL volumetric flask. 1 mL of the prepared aqueous solution was passed through an ODS (octadecyl group chemically bonded to silica gel) pretreatment cartridge and used for ion chromatographic analysis. Detection was performed under the following ion chromatographic conditions. The detected amount was measured by the peak area ratio with respect to a standard solution of known concentration, and the amount of phosphate ion (PO 4 3 ⁇ ) was converted.
- ODS octadecyl group chemically bonded to silica gel
- the amount of the phosphoric acid compound was adjusted so that the substance amount of phosphorus contained in the treatment agent was the same as when the phosphoric acid compound (P-1) was blended. 100 g of each of these was put into a vial bottle. To this was then added 1 g of distilled water. The vial was allowed to stand at 70° C. for 3 days, and whether inorganic phosphoric acid-derived particulate matter newly precipitated on the bottom of the vial was observed, and the stability was determined according to the following criteria. The results are shown in the "stability" column of Table 1.
- the test yarn was run in contact with a satin chrome pin with a surface temperature of 250°C at an initial tension of 1.5 kg and a yarn speed of 1.0 m/min, and the tension value of the yarn after contact with the satin chrome pin was measured.
- the running time was recorded when the tension value increased by 10% after 20 minutes of running, and was evaluated according to the following criteria. The results are shown in the "tension variation" column of Tables 2 and 3.
- the present invention also includes the following aspects.
- (Appendix 1) A synthetic fiber characterized by containing a smoothing agent (A), a nonionic surfactant (B), an ionic surfactant (C) containing the following phosphate ester compound (C1), and an alcohol compound (D)
- a treatment agent (excluding acrylic fiber treatment agents for carbon fiber production),
- the phosphate ester compound (C1) includes a phosphate ester P4 represented by the following chemical formula (4), optionally a phosphate ester P1 represented by the following chemical formula (1), and a phosphate ester P1 represented by the following chemical formula (2).
- a phosphate ester P3 represented by the following chemical formula (3), wherein the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the When the total P-nucleus NMR integral ratio attributed to the phosphate ester P4 is 100%, the P-nucleus NMR integral ratio attributed to the phosphate ester P1 is 7% or less,
- R 1 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms in total.
- R 2 and R 3 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- R 4 is an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an alkylene oxide having 2 to 3 carbon atoms per 1 mol of an aliphatic alcohol having 8 to 24 carbon atoms in total.
- R 5 and R 6 are each an alkyl group having 8 to 24 carbon atoms, an alkenyl group having 8 to 24 carbon atoms, or an aliphatic alcohol having 8 to 24 carbon atoms and 2 to 3 carbon atoms per 1 mol.
- the phosphate ester compound (C1) further includes the phosphate ester P2, and P-nuclear NMR integrals attributed to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the phosphate ester compound (C1) further includes the phosphate ester P2, and P-nuclear NMR integrals attributed to the phosphate ester P1, the phosphate ester P2, the phosphate ester P3, and the phosphate ester P4
- the P-nuclear NMR integral ratio attributed to the phosphate ester P1 is 5% or less
- the P-nuclear NMR integral ratio attributed to the phosphate ester P2 is 10% or more and 45%.
- the treatment agent for synthetic fibers according to Supplementary Note 1 or 2 below.
- the smoothing agent (A) contains at least one selected from the following complete ester compound (A1), the sulfur-containing ester compound (A2), and the following partial ester compound (A3),
- the complete ester compound (A1) is a complete ester compound of a polyhydric alcohol having a chain structure having 3 to 6 carbon atoms and a monovalent fatty acid having 8 to 24 carbon atoms and a monovalent monovalent having 8 to 24 carbon atoms.
- the partial ester compound (A3) is a partial ester compound of a polyhydric alcohol having a chain structure having 3 to 6 carbon atoms and a monovalent fatty acid having 8 to 24 carbon atoms.
- the synthetic fiber treatment agent according to 1.
- the content ratio of the complete ester compound (A1) and the sulfur-containing ester compound (A2) is such that the mass ratio of the complete ester compound (A1)/the sulfur-containing ester compound (A2) is 1/1 or more and 100/1 or less.
- Appendix 14 A synthetic fiber (excluding acrylic fiber for carbon fiber production) to which the synthetic fiber treatment agent according to any one of Appendices 1 to 13 is adhered.
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Abstract
Description
R1は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M1及びM2はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
mは2又は3の整数である。
R2及びR3はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M3は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
nは2又は3の整数である。
R4は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M4及びM5はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである。
R5及びR6はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M6は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである。
前記合成繊維用処理剤において、前記アルコール化合物(D)が1価アルコールを含み、前記合成繊維用処理剤中の1価アルコールの含有割合が0.0001質量%以上3質量%以下であってもよい。
前記合成繊維用処理剤において、前記平滑剤(A)が前記完全エステル化合物(A1)を含み、前記合成繊維用処理剤中における前記完全エステル化合物(A1)の含有割合が30質量%以上70質量%以下であってもよい。
前記合成繊維用処理剤において、前記完全エステル化合物(A1)及び前記含硫黄エステル化合物(A2)の含有比率が、質量比として前記完全エステル化合物(A1)/前記含硫黄エステル化合物(A2)=1/1以上100/1以下であってもよい。
前記合成繊維用処理剤において、前記完全エステル化合物(A1)及び前記部分エステル化合物(A3)の含有比率が、質量比として前記完全エステル化合物(A1)/前記部分エステル化合物(A3)=1/1以上10000/1以下であってもよい。
上記課題を解決するために、本発明の別の態様の合成繊維では、前記合成繊維用処理剤が付着していることを要旨とする。
以下、本発明の合成繊維用処理剤(以下、処理剤という)を具体化した第1実施形態を説明する。本実施形態の処理剤は、平滑剤(A)、ノニオン界面活性剤(B)、リン酸エステル化合物(C1)を含むイオン界面活性剤(C)、及びアルコール化合物(D)を含有する。処理剤は、例えば国際公開第2013/129115号に開示されているような炭素繊維製造用アクリル繊維処理剤とは異なり、炭素繊維製造用アクリル繊維以外の合成繊維の処理に用いられることが好ましい。
平滑剤(A)としては、例えばシリコーン油、鉱物油、ポリオレフィン、エステル油等が挙げられる。平滑剤(A)は、合成繊維に平滑性を付与する。
鎖状構造を有する多価アルコールとしては、環状構造を有しない多価アルコールが挙げられ、鎖状構造としては、直鎖状のものであっても、分岐鎖構造を有するものであってもよい。炭素数3以上6以下の鎖状構造を有する多価アルコールの具体例としては、例えばグリセリン、ジグリセリン、ペンタエリスリトール、ソルビトール、トリメチロールエタン、トリメチロールプロパン、ブタントリオール、ペンタントリオール、ヘキサントリオール等が挙げられる。
(ノニオン界面活性剤(B))
ノニオン界面活性剤(B)としては、例えば、アルコール類又はカルボン酸類にアルキレンオキサイドを付加させたもの、カルボン酸類と多価アルコールとのエステル化合物にアルキレンオキサイドを付加させたエーテル・エステル化合物、アミン化合物としてアルキルアミン類にアルキレンオキサイドを付加させたもの、カルボン酸類と炭素数3以上6以下の環状構造を有する多価アルコール等との部分エステル化合物等が挙げられる。これらのノニオン界面活性剤(B)は、一種類のノニオン界面活性剤を単独で使用してもよいし、又は二種以上のノニオン界面活性剤を適宜組み合わせて使用してもよい。
リン酸エステル化合物(C1)は、下記の化学式(1)で示されるリン酸エステルP1、下記の化学式(2)で示されるリン酸エステルP2、下記の化学式(3)で示されるリン酸エステルP3、及び下記の化学式(4)で示されるリン酸エステルP4から選ばれる少なくとも1つを含んでいる。
R1は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M1及びM2はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
mは2又は3の整数である。
R1を構成するアルキル基としては、直鎖のアルキル基であっても分岐鎖構造を有するアルキル基であってもよい。R1を構成するアルケニル基としては、直鎖のアルケニル基であっても分岐鎖構造を有するアルケニル基であってもよい。
R2及びR3はそれぞれ、炭素数8以上24以下のアルキル基、又は炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M3は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
nは2又は3の整数である。
R2又はR3を構成するアルキル基としては、直鎖のアルキル基であっても分岐鎖構造を有するアルキル基であってもよい。R2又はR3を構成するアルケニル基としては、直鎖のアルケニル基であっても分岐鎖構造を有するアルケニル基であってもよい。
リン酸エステルP3は、下記の化学式(3)で示される。
R4は炭素数8以上24以下のアルキル基、又は炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M4及びM5はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである。
R4を構成するアルキル基としては、直鎖のアルキル基であっても分岐鎖構造を有するアルキル基であってもよい。R4を構成するアルケニル基としては、直鎖のアルケニル基であっても分岐鎖構造を有するアルケニル基であってもよい。
リン酸エステルP4は、下記の化学式(4)で示される。
R5及びR6はそれぞれ、炭素数8以上24以下のアルキル基、又は炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M6は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである。
R5又はR6を構成するアルキル基としては、直鎖のアルキル基であっても分岐鎖構造を有するアルキル基であってもよい。R5又はR6を構成するアルケニル基としては、直鎖のアルケニル基であっても分岐鎖構造を有するアルケニル基であってもよい。
リン酸エステル化合物(C1)は、アルカリ過中和前処理した際のP核NMR測定において、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP1に帰属されるP核NMR積分比率が7%以下であるものが適用される。
P1_P%は、リン酸エステルP1に帰属されるP核NMR積分比率、
P1_Pは、リン酸エステルP1に帰属されるP核NMR積分値、
P2_Pは、リン酸エステルP2に帰属されるP核NMR積分値、
P3_Pは、リン酸エステルP3に帰属されるP核NMR積分値、
P4_Pは、リン酸エステルP4に帰属されるP核NMR積分値を表す。
P2_P%は、リン酸エステルP2に帰属されるP核NMR積分比率、
P1_Pは、リン酸エステルP1に帰属されるP核NMR積分値、
P2_Pは、リン酸エステルP2に帰属されるP核NMR積分値、
P3_Pは、リン酸エステルP3に帰属されるP核NMR積分値、
P4_Pは、リン酸エステルP4に帰属されるP核NMR積分値を表す。
P3_P%は、リン酸エステルP3に帰属されるP核NMR積分比率、
P1_Pは、リン酸エステルP1に帰属されるP核NMR積分値、
P2_Pは、リン酸エステルP2に帰属されるP核NMR積分値、
P3_Pは、リン酸エステルP3に帰属されるP核NMR積分値、
P4_Pは、リン酸エステルP4に帰属されるP核NMR積分値を表す。
P4_P%は、リン酸エステルP4に帰属されるP核NMR積分比率、
P1_Pは、リン酸エステルP1に帰属されるP核NMR積分値、
P2_Pは、リン酸エステルP2に帰属されるP核NMR積分値、
P3_Pは、リン酸エステルP3に帰属されるP核NMR積分値、
P4_Pは、リン酸エステルP4に帰属されるP核NMR積分値を表す。
処理剤は、リン酸エステル化合物(C1)以外のイオン界面活性剤(C)を含んでもよい。リン酸エステル化合物(C1)以外のイオン界面活性剤(C)としては、公知のものを適宜採用できる。イオン界面活性剤としては、アニオン界面活性剤、カチオン界面活性剤、両性界面活性剤が挙げられる。
これらのイオン界面活性剤(C)は、一種類のイオン界面活性剤を単独で使用してもよいし、又は二種以上のイオン界面活性剤を適宜組み合わせて使用してもよい。
アルコール化合物(D)は、処理剤の保存時の安定性をより向上させる作用を有する。また、処理剤の耐熱性をより向上させる作用も有する。アルコール化合物(D)としては、例えば1価アルコール、多価アルコール等が挙げられる。アルコール化合物(D)としては、1価アルコール及びジオールから選ばれる少なくとも1つを含むものであることが好ましい。かかる化合物により、加熱ローラー上への処理剤析出物の脱落を抑制し、タールの蓄積等を抑制する。1価アルコールとしては、例えば低級アルコール、高級アルコール等が挙げられる。さらに高級アルコールとしては、例えば炭素数8以上24以下の1価脂肪族アルコールが挙げられる。
処理剤は、イオンクロマトグラフ法により処理剤から検出されるリン酸イオンの濃度が200ppm以下であることが好ましく、150ppm以下であることがより好ましい。かかる範囲に規定されることにより、加熱ローラー上の処理剤又はタールの蓄積が抑制される。
次に、本発明による合成繊維を具体化した第2実施形態を説明する。本実施形態の合成繊維には、第1実施形態の処理剤が付着している。処理剤を合成繊維に付着させる際の処理剤の形態としては、希釈溶媒で希釈した希釈溶液、例えば低粘度鉱物油溶液、有機溶媒溶液、水性液等として付与してもよい。第1実施形態の処理剤によると、低粘度鉱物油等の非極性溶媒で希釈した処理剤の保存安定性を特に向上させることができる。合成繊維は、水性液等の処理剤の希釈溶液を、例えば紡糸又は延伸工程等において合成繊維に付着させる工程を経て得られる。合成繊維に付着した希釈液は、延伸工程、乾燥工程により希釈溶媒を蒸発させてもよい。合成繊維への処理剤の付着は、紡糸工程で行われる限りそのタイミングに特に制限はない。延伸もしくは熱処理工程において、150℃以上のローラーを通過させる工程を有する製造設備、又はそのような工程での使用により、発明の効果がより期待できる。
本実施形態の処理剤は、平滑剤、ノニオン界面活性剤、アルコール化合物、及び特定のリン酸エステル化合物を含有する。これにより、処理剤の耐熱性が向上するとともに、処理剤の保存安定性が向上する。そしてその結果、特にリン酸エステルP1の分解により生ずる無機リン酸又はその塩由来の析出物、その沈殿、製糸中のタール等の発生を抑制できる。
なお、上記実施形態は以下のように変更してもよい。上記実施形態及び以下の変更例は、技術的に矛盾しない範囲で互いに組み合わせて実施できる。
各実施例、各比較例の処理剤に用いられるリン酸エステル化合物を、以下に示される方法により合成した。
原料アルコールとしてイソセチルアルコールは、105℃で減圧脱水を行ったものを使用した。4つ口フラスコにイソセチルアルコールを仕込み、これに窒素雰囲気下で五酸化二燐を徐々に投入し、70±5℃で3時間撹拌することでリン酸化反応を行った。リン酸化物をカラムクロマトグラフィーで精製し、次いで中和剤としてジブチルエタノールアミンと混合し、50℃で1時間撹拌することによりリン酸エステル化合物(P-1)を合成した。ジブチルエタノールアミンの仕込み量は、リン酸化物の量とその酸価(1mol/LのKOH溶液で滴定して求められる約pH11の滴定点での酸価)とジブチルエタノールアミンの塩基価から計算して求めた(ジブチルエタノールアミンの仕込み量=リン酸化物の仕込み量×酸価/塩基価)。
リン酸エステル化合物(P-2~P-6)は、原料アルコールとして表1に記載の原料を使用し、P-1と同様の方法で合成した。尚、リン酸エステル化合物(rP-1、rP-2)のリン酸化反応は、大気下で行い、原料の五酸化二燐は試薬瓶開封後、全量投入まで大気下(室温:約27℃、相対湿度:約80%)に置いた(投入開始から投入終了まで30分程度要した)。リン酸エステル化合物(rP-1)の中和は、水酸化カリウム水溶液にリン酸化物を仕込み、撹拌することで行い、自然乾燥させてから処理剤に供した。
上記のように合成された各リン酸エステル化合物(C1)0.10gに対してアルカリとしてラウリルアミン0.15gを添加し撹拌することにより前処理した。そして、31P-NMRを用いてリン酸エステルP1~P4に帰属される各P核NMR積分値を求めた。
各実施例、各比較例に用いた処理剤は、表2,3に示される各成分を使用し、下記調製方法により調製した。
試料1g(揮発分も含む)を正確に量りとり、撹拌しながら10%の2-プロパノール水溶液を少しずつ加え、100mLメスフラスコで定容した溶液を作製した。作製した水溶液1mLを、ODS(シリカゲルにオクタデシル基を化学結合させた)前処理カートリッジに通し、イオンクロマトグラフ分析に使用した。以下のイオンクロマトグラフ条件により検出を行った。濃度既知の標準液に対するピーク面積比にて検出量を測定し、リン酸イオン(PO4 3-)の量を換算した。
装置:東ソー社製 IC2001 サプレッサ使用、
分析カラム:東ソー社製 TSKgel SuperIC-AZ 内径4.6mm×長さ75mm、
ガードカラム:東ソー社製 TSKgel guardcolumn SuperIC-AZ、内径4.0mm×長さ10mm、
溶離液:4.8mmolのNa2CO3、2.8mmolのNaHCO3の23容量%メタノール水溶液、
流量:0.6mL/min。
(平滑剤(A))
L-1:トリメチロールプロパントリオレアート
L-2:ジイソステアリルアジパート
L-3:ナタネ油
LS-1:ジイソステアリルチオジプロピオナート
LS-2:ジオレイルチオジプロピオナート
pL-1:トリメチロールプロパンジオレアート
pL-2:グリセリンジオレアート
eL-1:オクチルパルミタート
(ノニオン界面活性剤(B))
N-1:オレイルアルコール1モルに対しEO10モルを付加したもの
N-2:イソトリデカノール1モルに対しEO10モルを付加したもの
N-3:イソトリデカノール1モルに対してEO10モルとPO10モルをランダムに付加したもの
N-4:硬化ひまし油1モルに対しEO10モルを付加したもの
N-5:硬化ひまし油1モルにEO20モルを付加してからオレイン酸3モルでエステル化した化合物
N-6:硬化ひまし油1モルに対しEO25モルを付加してからアジピン酸で架橋し、ステアリン酸で末端エステル化した化合物(平均分子量5000)
N-7:ソルビタンモノオレアート
N-8:ソルビタントリオレアート
N-9:ポリエチレングリコール(平均分子量600)とオレイン酸のジエステル
N-10:ポリエチレングリコール(平均分子量400)とラウリン酸のジエステル
N-11:ポリエチレングリコール(平均分子量600)とオレイン酸のモノエステル
N-12:ラウリルアミン1モルに対しEO3モルを付加したもの
N-13:ラウリルアミン1モルに対しEO10モルを付加したもの
(イオン界面活性剤(C))
S-1:2級アルカンスルホン酸ナトリウム(C=14~17)
S-2:ジオクチルスルホコハク酸ナトリウム
S-3:ドデシルベンゼンスルホン酸カリウム塩
S-4:α-オレフィンスルホン酸ナトリウム
(アルコール化合物(D))
AL-1:イソセチルアルコール
AL-2:イソステアリルアルコール
AL-3:オレイルアルコール
AL-4:イソテトラコサノール
D-1:ポリエチレングリコール(平均分子量200)
D-2:ポリエチレングリコール(平均分子量400)
D-3:ポリプロピレングリコール(平均分子量400)
D-4:ポリオキシエチレンプロピレングリコール(PO1モル、EO4モル)
D-5:エチレングリコール
D-6:プロピレングリコール
D-7:ジエチレングリコール
試験区分3(処理剤及び合成繊維の評価)
・安定性の評価
実施例1の処理剤と、実施例1の処理剤におけるリン酸エステル化合物(P-1)を表1に記載の別のリン酸エステル化合物(P-2~6、rP-1、rP-2)に変更した処理剤とを調製した。なお、処理剤に含まれるリンの物質量がリン酸化合物(P-1)を配合した時と同じとなるようにリン酸化合物の配合量を調整した。これらをバイアル瓶に100gずつ入れた。次いで、これに1gの蒸留水を加えた。バイアル瓶を70℃で3日間静置し、無機リン酸由来の粒子状の物質がバイアル底部に新たに析出するかを観察し、安定性を下記の基準で判定した。結果を表1の「安定性」欄に示す。
×(不良):析出した場合
・張力変動の評価
各処理剤を必要に応じてイオン交換水又は有機溶剤の希釈剤にて均一に希釈し、15%溶液とした。1000デシテックス、192フィラメント、固有粘度0.93のポリエチレンテレフタラート繊維(無給油糸)に、前記の溶液を、オイリングローラー給油法にて不揮発分として付与量3.0質量%となるように付与し、希釈剤を乾燥させ試験糸とした。
○(可):3時間以上6時間未満
×(不良):3時間未満
・タールの評価
処理剤の耐熱性評価として、張力変動試験で6時間経過した後の梨地クロムピンに堆積したタールを観察し、次の基準で評価した。結果を表2,3の「タール」欄に示す。
○(可):うっすらと茶色のタールが観察される場合
×(不良):濃い茶色もしくは黒色のタールが観察される場合
表1~3の各実施例の評価結果からも明らかなように、本発明の処理剤によると、保存安定性に優れ、張力変動、タールが低減していることが確認された。
(付記1)
平滑剤(A)、ノニオン界面活性剤(B)、下記のリン酸エステル化合物(C1)を含むイオン界面活性剤(C)、及びアルコール化合物(D)を含有することを特徴とする合成繊維用処理剤(ただし、炭素繊維製造用アクリル繊維処理剤を除く)であって、
リン酸エステル化合物(C1)は、下記の化学式(4)で示されるリン酸エステルP4を含み、任意選択で下記の化学式(1)で示されるリン酸エステルP1、下記の化学式(2)で示されるリン酸エステルP2、及び下記の化学式(3)で示されるリン酸エステルP3から選ばれる少なくとも1つをさらに含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP1に帰属されるP核NMR積分比率が7%以下であり、
R1は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M1及びM2はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
mは2又は3の整数であり、
R2及びR3はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M3は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
nは2又は3の整数であり、
R4は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M4及びM5はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
R5及びR6はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M6は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである、合成繊維用処理剤。
前記リン酸エステル化合物(C1)が前記リン酸エステルP2をさらに含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP2に帰属されるP核NMR積分比率が5%以上50%以下である付記1に記載の合成繊維用処理剤。
前記リン酸エステル化合物(C1)が前記リン酸エステルP2をさらに含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP1に帰属されるP核NMR積分比率が5%以下、及び前記リン酸エステルP2に帰属されるP核NMR積分比率が10%以上45%以下である付記1又は2に記載の合成繊維用処理剤。
前記アルコール化合物(D)が、1価アルコール及びジオールから選ばれる少なくとも1つを含むものである付記1~3のいずれか一つに記載の合成繊維用処理剤。
前記アルコール化合物(D)が1価アルコールを含み、前記合成繊維用処理剤中の1価アルコールの含有割合が0.0001質量%以上3質量%以下である付記4に記載の合成繊維用処理剤。
前記アルコール化合物(D)がジオールを含み、前記合成繊維用処理剤中のジオールの含有割合が0.001質量%以上5質量%以下である付記4又は5に記載の合成繊維用処理剤。
前記平滑剤(A)が、下記の完全エステル化合物(A1)、含硫黄エステル化合物(A2)、及び下記の部分エステル化合物(A3)から選ばれる少なくとも1つを含み、
完全エステル化合物(A1)は、炭素数3以上6以下の鎖状構造を有する多価アルコールと炭素数8以上24以下の1価脂肪酸との完全エステル化合物、及び炭素数8以上24以下の1価アルコールと炭素数3以上10以下の多価脂肪酸との完全エステル化合物から選ばれる少なくとも1つであり、
部分エステル化合物(A3)は、炭素数3以上6以下の鎖状構造を有する多価アルコールと炭素数8以上24以下の1価脂肪酸との部分エステル化合物である、付記1~6のいずれか一つに記載の合成繊維用処理剤。
前記平滑剤(A)が前記完全エステル化合物(A1)を含み、前記合成繊維用処理剤中における前記完全エステル化合物(A1)の含有割合が30質量%以上70質量%以下である付記7に記載の合成繊維用処理剤。
前記平滑剤(A)が前記含硫黄エステル化合物(A2)を含むものである付記8に記載の合成繊維用処理剤。
前記完全エステル化合物(A1)及び前記含硫黄エステル化合物(A2)の含有比率が、質量比として前記完全エステル化合物(A1)/前記含硫黄エステル化合物(A2)=1/1以上100/1以下である付記9に記載の合成繊維用処理剤。
前記平滑剤(A)が前記部分エステル化合物(A3)を含むものである付記8~10のいずれか一つに記載の合成繊維用処理剤。
前記完全エステル化合物(A1)及び前記部分エステル化合物(A3)の含有比率が、質量比として前記完全エステル化合物(A1)/前記部分エステル化合物(A3)=1/1以上10000/1以下である付記11に記載の合成繊維用処理剤。
イオンクロマトグラフ法により合成繊維用処理剤から検出されるリン酸イオンの濃度が200ppm以下である付記1~12のいずれか一つに記載の合成繊維用処理剤。
付記1~13のいずれか一つに記載の合成繊維用処理剤が付着していることを特徴とする合成繊維(ただし、炭素繊維製造用アクリル繊維を除く)。
Claims (14)
- 平滑剤(A)、ノニオン界面活性剤(B)、下記のリン酸エステル化合物(C1)を含むイオン界面活性剤(C)、及びアルコール化合物(D)を含有することを特徴とする合成繊維用処理剤であって、
リン酸エステル化合物(C1)は、下記の化学式(1)で示されるリン酸エステルP1、下記の化学式(2)で示されるリン酸エステルP2、下記の化学式(3)で示されるリン酸エステルP3、及び下記の化学式(4)で示されるリン酸エステルP4から選ばれる少なくとも1つを含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP1に帰属されるP核NMR積分比率が7%以下であり、
化学式(1)において、
R1は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M1及びM2はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
mは2又は3の整数であり、
化学式(2)において、
R2及びR3はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M3は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
nは2又は3の整数であり、
化学式(3)において、
R4は炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M4及びM5はそれぞれ、水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムであり、
化学式(4)において、
R5及びR6はそれぞれ、炭素数8以上24以下のアルキル基、炭素数8以上24以下のアルケニル基、又は炭素数8以上24以下の脂肪族アルコール1モルに対し炭素数2以上3以下のアルキレンオキサイドを合計で1モル以上20モル以下付加したものから水酸基を除いた残基であり、
M6は水素原子、アルカリ金属、アルカリ土類金属(1/2)、有機アミン塩、アンモニウム、又はホスホニウムである、合成繊維用処理剤。 - 前記リン酸エステル化合物(C1)が前記リン酸エステルP2を含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP2に帰属されるP核NMR積分比率が5%以上50%以下である請求項1に記載の合成繊維用処理剤。
- 前記リン酸エステル化合物(C1)が前記リン酸エステルP2を含み、前記リン酸エステルP1、前記リン酸エステルP2、前記リン酸エステルP3、及び前記リン酸エステルP4に帰属されるP核NMR積分比率の合計を100%としたとき、前記リン酸エステルP1に帰属されるP核NMR積分比率が5%以下、及び前記リン酸エステルP2に帰属されるP核NMR積分比率が10%以上45%以下である請求項1又は2に記載の合成繊維用処理剤。
- 前記アルコール化合物(D)が、1価アルコール及びジオールから選ばれる少なくとも1つを含むものである請求項1~3のいずれか一項に記載の合成繊維用処理剤。
- 前記アルコール化合物(D)が1価アルコールを含み、前記合成繊維用処理剤中の1価アルコールの含有割合が0.0001質量%以上3質量%以下である請求項4に記載の合成繊維用処理剤。
- 前記アルコール化合物(D)がジオールを含み、前記合成繊維用処理剤中のジオールの含有割合が0.001質量%以上5質量%以下である請求項4又は5に記載の合成繊維用処理剤。
- 前記平滑剤(A)が、下記の完全エステル化合物(A1)、含硫黄エステル化合物(A2)、及び下記の部分エステル化合物(A3)から選ばれる少なくとも1つを含み、
完全エステル化合物(A1)は、炭素数3以上6以下の鎖状構造を有する多価アルコールと炭素数8以上24以下の1価脂肪酸との完全エステル化合物、及び炭素数8以上24以下の1価アルコールと炭素数3以上10以下の多価脂肪酸との完全エステル化合物から選ばれる少なくとも1つであり、
部分エステル化合物(A3)は、炭素数3以上6以下の鎖状構造を有する多価アルコールと炭素数8以上24以下の1価脂肪酸との部分エステル化合物である、請求項1~6のいずれか一項に記載の合成繊維用処理剤。 - 前記平滑剤(A)が前記完全エステル化合物(A1)を含み、前記合成繊維用処理剤中における前記完全エステル化合物(A1)の含有割合が30質量%以上70質量%以下である請求項7に記載の合成繊維用処理剤。
- 前記平滑剤(A)が前記含硫黄エステル化合物(A2)を含むものである請求項8に記載の合成繊維用処理剤。
- 前記完全エステル化合物(A1)及び前記含硫黄エステル化合物(A2)の含有比率が、質量比として前記完全エステル化合物(A1)/前記含硫黄エステル化合物(A2)=1/1以上100/1以下である請求項9に記載の合成繊維用処理剤。
- 前記平滑剤(A)が前記部分エステル化合物(A3)を含むものである請求項8~10のいずれか一項に記載の合成繊維用処理剤。
- 前記完全エステル化合物(A1)及び前記部分エステル化合物(A3)の含有比率が、質量比として前記完全エステル化合物(A1)/前記部分エステル化合物(A3)=1/1以上10000/1以下である請求項11に記載の合成繊維用処理剤。
- イオンクロマトグラフ法により合成繊維用処理剤から検出されるリン酸イオンの濃度が200ppm以下である請求項1~12のいずれか一項に記載の合成繊維用処理剤。
- 請求項1~13のいずれか一項に記載の合成繊維用処理剤が付着していることを特徴とする合成繊維。
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JP7365090B1 (ja) * | 2023-07-18 | 2023-10-19 | 竹本油脂株式会社 | アクリル系合成繊維用処理剤含有組成物、アクリル系合成繊維用処理剤含有組成物の希釈液の調製方法及びアクリル系合成繊維 |
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