JP6967815B1 - Synthetic fiber treatment agent, synthetic fiber and synthetic fiber treatment method - Google Patents
Synthetic fiber treatment agent, synthetic fiber and synthetic fiber treatment method Download PDFInfo
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- JP6967815B1 JP6967815B1 JP2021068748A JP2021068748A JP6967815B1 JP 6967815 B1 JP6967815 B1 JP 6967815B1 JP 2021068748 A JP2021068748 A JP 2021068748A JP 2021068748 A JP2021068748 A JP 2021068748A JP 6967815 B1 JP6967815 B1 JP 6967815B1
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- treatment agent
- ring
- synthetic fibers
- carbon atoms
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- 239000012209 synthetic fiber Substances 0.000 title claims abstract description 129
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 73
- -1 aliphatic monocarboxylic acid Chemical class 0.000 claims description 123
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 229910019142 PO4 Inorganic materials 0.000 claims description 39
- 239000010452 phosphate Substances 0.000 claims description 39
- 239000002563 ionic surfactant Substances 0.000 claims description 21
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002736 nonionic surfactant Substances 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- 238000009499 grossing Methods 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
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- 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 3
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- OZYPPHLDZUUCCI-UHFFFAOYSA-N n-(6-bromopyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(Br)=N1 OZYPPHLDZUUCCI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940033623 potassium lauryl phosphate Drugs 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical class [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- GBEYVKHMIPVAHD-UHFFFAOYSA-M potassium;hexadecyl sulfate Chemical compound [K+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GBEYVKHMIPVAHD-UHFFFAOYSA-M 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical group [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—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
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/08—Melt spinning methods
- D01D5/096—Humidity control, or oiling, of filaments, threads or the like, leaving the spinnerettes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—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
- D06M13/165—Ethers
- D06M13/17—Polyoxyalkyleneglycol ethers
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- 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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- 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
- D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
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Abstract
【課題】合成繊維に良好な制電性を付与し、かつ、エマルション安定性及び低温ハンドリング性に優れる合成繊維用処理剤、かかる処理剤が付着した合成繊維及び、かかる合成繊維用処理剤を合成繊維に付着させる処理方法の提供を課題としている。【解決手段】上記一般式（１）及び上記一般式（２）で示されるシクロアルキルアルカノール誘導体から選択される１種以上を含有することを特徴とする合成繊維用処理剤。【選択図】なしPROBLEM TO BE SOLVED: To synthesize a synthetic fiber treatment agent which imparts good antistatic property to synthetic fibers and is excellent in emulsion stability and low temperature handleability, a synthetic fiber to which such a treatment agent is attached, and a synthetic fiber treatment agent. The subject is to provide a treatment method for adhering to fibers. SOLUTION: The treatment agent for synthetic fibers is characterized by containing at least one selected from the cycloalkyl alkanol derivatives represented by the general formula (1) and the general formula (2). [Selection diagram] None
Description
本発明は、合成繊維用処理剤、合成繊維及び合成繊維の処理方法に関する。 The present invention relates to a processing agent for synthetic fibers, synthetic fibers, and a method for treating synthetic fibers.
近年、合成繊維の紡糸工程や仮撚工程、後加工工程においては、高速化が更に一段と進み、これに伴って静電気の発生や生産糸の毛羽がますます発生し易くなっている。かかる静電気や毛羽の発生を防止するため、合成繊維に付着させる合成繊維用処理剤としてこれらを防止するための機能性向上剤の含有割合を増加させたものを使用することや、合成繊維に対する合成繊維用処理剤の付着量を上げることが行われているが、依然として充分な対応ではなく、さらなる制電性の向上が要望されている。 In recent years, in the spinning process, false twisting process, and post-processing process of synthetic fibers, the speed has been further increased, and along with this, static electricity and fluffing of produced yarns are becoming more and more likely to occur. In order to prevent the generation of such static electricity and fluff, as a treatment agent for synthetic fibers to be attached to synthetic fibers, an agent having an increased content ratio of a functional improver for preventing these may be used, or synthetic to synthetic fibers may be used. Although the amount of the fiber treatment agent attached has been increased, it is still not sufficient and there is a demand for further improvement in antistatic property.
一方、合成繊維は様々な国や地域において生産が行われており、それに伴って合成繊維用処理剤の使用条件も多岐にわたり、例えば、温度条件において、非常に広い温度範囲での使用に耐えられる合成繊維用処理剤が望まれている。
しかしながら、ポリエーテル類（ＰＯ／ＥＯ共重合体）を含有する合成繊維用処理剤（例えば、特許文献１等）が多く知られている一方で、これらの合成繊維用処理剤はエマルションの安定性が不十分である場合があった。
合成繊維用処理剤のエマルション安定性が悪いと、例えば、エマルション調製タンク内で貯蔵している間に含有成分が分離してしまい、これを合成繊維に付着させると合成繊維用処理剤が均一に付着せず、その後の紡糸工程や仮撚工程、後加工工程において問題が多発する原因となる。
また、氷点下の環境下における低温ハンドリング性の低下は、例えば、合成繊維用処理剤の成分が凝固して含有成分が不均一な状態になり十分に機能を発揮できなかったり、エマルション調製のための仕込みに時間を要したりする原因となる。
すなわち、合成繊維用処理剤のエマルション安定性や低温ハンドリング性の向上は、合成繊維の品質を向上させる要因であるため重要な課題である。
On the other hand, synthetic fibers are produced in various countries and regions, and the conditions for using synthetic fiber treatment agents are also diverse. For example, they can withstand use in a very wide temperature range under temperature conditions. A treatment agent for synthetic fibers is desired.
However, while many synthetic fiber treatment agents containing polyethers (PO / EO copolymers) (for example, Patent Document 1 and the like) are known, these synthetic fiber treatment agents have emulsion stability. Was sometimes inadequate.
If the emulsion stability of the synthetic fiber treatment agent is poor, for example, the contained components are separated during storage in the emulsion preparation tank, and when this is attached to the synthetic fiber, the synthetic fiber treatment agent becomes uniform. It does not adhere and causes frequent problems in the subsequent spinning process, false twisting process, and post-processing process.
Further, the deterioration of the low temperature handling property in the environment below the freezing point is caused by, for example, the components of the synthetic fiber treatment agent coagulating and the contained components becoming non-uniform and unable to sufficiently exert their functions, or for preparing an emulsion. It may take time to prepare.
That is, improvement of emulsion stability and low temperature handleability of the synthetic fiber treatment agent is an important issue because it is a factor for improving the quality of the synthetic fiber.
本発明は、合成繊維に良好な制電性を付与し、かつ、エマルション安定性及び低温ハンドリング性に優れる合成繊維用処理剤、かかる処理剤が付着した合成繊維及び、かかる合成繊維用処理剤を合成繊維に付着させる処理方法の提供を課題としている。 The present invention provides a synthetic fiber treatment agent that imparts good antistatic properties to synthetic fibers and is excellent in emulsion stability and low temperature handleability, a synthetic fiber to which such a treatment agent is attached, and a synthetic fiber treatment agent. The subject is to provide a treatment method for adhering to synthetic fibers.
本発明者は上記課題を解決するために鋭意研究を重ねた結果、合成繊維に良好な制電性を付与し、かつ、エマルション安定性及び低温ハンドリング性に優れる合成繊維用処理剤とするためには、特定の化学構造を有するシクロアルキルアルカノール誘導体が大きく関与していることを見出し、上記課題を解決するに至ったものである。 As a result of diligent research to solve the above problems, the present inventor has made it a treatment agent for synthetic fibers, which imparts good antistatic properties to synthetic fibers and has excellent emulsion stability and low-temperature handling properties. Has found that cycloalkyl alkanol derivatives having a specific chemical structure are largely involved, and has solved the above-mentioned problems.
本発明は、具体的には次の事項を要旨とする。
１．下記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体から選択される１種以上を含有することを特徴とする合成繊維用処理剤。
環Ｑａ：炭素数３〜８のシクロアルキレン基
Ｒ１ａ：水素原子又は炭素数１〜１２のアルキル基
Ｒ２ａ：炭素数１〜１２の２価の炭化水素基
Ｒ３：水素原子又は炭素数６〜２２のモノカルボン酸から水酸基を除いた残基
Ａ１ａＯ：炭素数２〜４のアルキレンオキシ基（ただし、当該アルキレンオキシ基が２以上存在する場合は、１種単独又は２種以上でも良い。）
ｍａ：０〜１００の整数、
ただし、ｍ ａ が０でありＲ ３ が水素原子である場合を除く。）
Ｒ４：炭素数４〜１２のジカルボン酸から２つの水酸基を除いた残基、
ただし、ｍ ｂ が０である場合を除く。）
２．前記一般式（１）におけるＲ１ａは水素原子であるシクロアルキルアルカノール誘導体及び、前記一般式（２）におけるＲ１ｂは水素原子であるシクロアルキルアルカノール誘導体から選択される１種以上を含有する、１．に記載の合成繊維用処理剤。
３．前記一般式（１）におけるＲ２ａは炭素数２〜８の２価の炭化水素基であるシクロアルキルアルカノール誘導体及び、前記一般式（２）におけるＲ２ｂは炭素数２〜８の２価の炭化水素基であるシクロアルキルアルカノール誘導体から選択される１種以上を含有する、１．又は２．に記載の合成繊維用処理剤。
４．前記一般式（１）におけるＲ３は炭素数６〜２２の脂肪族モノカルボン酸から水酸基を除いた残基であるシクロアルキルアルカノール誘導体及び、前記一般式（２）で示されるシクロアルキルアルカノール誘導体から選択される１種以上を含有する、１．〜３．のいずれか一項に記載の合成繊維用処理剤。
５．前記合成繊維用処理剤の全質量に対して、前記シクロアルキルアルカノール誘導体を０．０１〜３０質量％含有する１．〜４．のいずれか一項に記載の合成繊維用処理剤。
６．更に、非イオン性界面活性剤（但し、前記シクロアルキルアルカノール誘導体を除く）及びイオン性界面活性剤を含有する１．〜５．のいずれか一項に記載の合成繊維用処理剤。
７．更に、平滑剤、非イオン性界面活性剤（但し、前記シクロアルキルアルカノール誘導体を除く）及びイオン性界面活性剤を含有する１．〜５．のいずれか一項に記載の合成繊維用処理剤。
８．前記イオン性界面活性剤が、下記の一般式（３）で示される有機リン酸エステルＰ１、下記の一般式（４）で示される有機リン酸エステルＰ２、及び下記の一般式（５）で示される有機リン酸エステルＰ３から選ばれる少なくとも１つの有機リン酸エステルを含有する６．又は７．に記載の合成繊維用処理剤。
ｎ：２〜４の整数
Ｒ５：「Ｒ１ｃ−環Ｑｃ−Ｒ２ｃ−Ｏ−（Ａ１ｃＯ）ｍｃ−」から末端の酸素原子を除いた残基（ただし、環Ｑｃ、Ｒ１ｃ、Ｒ２ｃ、Ａ１ｃＯ、ｍｃは、一般式（１）の環Ｑａ、Ｒ１ａ、Ｒ２ａ、Ａ１ａＯ、ｍａと各々独立して同じ意味である。）、アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子
Ｍ１：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ２：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ３、Ｍ４：各々独立してアルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
９．１．〜８．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。
１０．１．〜８．のいずれか一項に記載の合成繊維用処理剤を合成繊維に対し０．１〜５質量％となるように付着させることを特徴とする合成繊維の処理方法。
Specifically, the present invention has the following gist.
1. 1. A treatment agent for synthetic fibers, which comprises one or more selected from the cycloalkyl alkanol derivatives represented by the following general formulas (1) and (2).
Ring Q a: cycloalkylene group R 1a having 3 to 8 carbon atoms: alkyl groups R 2a hydrogen atom or 1 to 12 carbon atoms: a divalent hydrocarbon group having 1 to 12 carbon atoms R 3: a hydrogen atom or a carbon atoms Residues obtained by removing hydroxyl groups from 6 to 22 monocarboxylic acids A 1a O: alkyleneoxy groups having 2 to 4 carbon atoms (however, if two or more of the alkyleneoxy groups are present, one type alone or two or more types may be used. good.)
m a: 0~100 of integer,
However, this does not apply when ma is 0 and R 3 is a hydrogen atom. )
R 4 : A residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms .
However, this does not apply when mb is 0. )
2. 2. R 1a in the general formula (1) contains one or more selected from a cycloalkyl alkanol derivative which is a hydrogen atom, and R 1b in the general formula (2) contains one or more selected from a cycloalkyl alkanol derivative which is a hydrogen atom. .. The treatment agent for synthetic fibers described in 1.
3. 3. R 2a in the general formula (1) is a cycloalkyl alkanol derivative which is a divalent hydrocarbon group having 2 to 8 carbon atoms, and R 2b in the general formula (2) is a divalent hydrocarbon having 2 to 8 carbon atoms. 1. Containing one or more selected from cycloalkyl alkanol derivatives which are hydrogen groups. Or 2. The treatment agent for synthetic fibers described in 1.
4. R 3 in the general formula (1) is derived from a cycloalkyl alkanol derivative which is a residue obtained by removing a hydroxyl group from an aliphatic monocarboxylic acid having 6 to 22 carbon atoms and a cycloalkyl alkanol derivative represented by the general formula (2). 1. Contains one or more selected species. ~ 3. The treatment agent for synthetic fibers according to any one of the above.
5. 1. The cycloalkyl alkanol derivative is contained in an amount of 0.01 to 30% by mass based on the total mass of the synthetic fiber treatment agent. ~ 4. The treatment agent for synthetic fibers according to any one of the above.
6. Further, it contains a nonionic surfactant (excluding the cycloalkyl alkanol derivative) and an ionic surfactant. ~ 5. The treatment agent for synthetic fibers according to any one of the above.
7. Further, it contains a smoothing agent, a nonionic surfactant (excluding the cycloalkyl alkanol derivative) and an ionic surfactant. ~ 5. The treatment agent for synthetic fibers according to any one of the above.
8. The ionic surfactant is represented by the organic phosphate ester P1 represented by the following general formula (3), the organic phosphate ester P2 represented by the following general formula (4), and the following general formula (5). 6. Contains at least one organic phosphate ester selected from the organic phosphate esters P3. Or 7. The treatment agent for synthetic fibers described in 1.
n: Integer of 2 to 4 R 5 : Residue excluding the terminal oxygen atom from "R 1c -ring Q c- R 2c -O- (A 1c O) m c- " (however, ring Q c , R 1c, R 2c, a 1c O , m c is a ring Q a in the general formula (1), R 1a, R 2a, a 1a O, m a and each independently the same meaning.), alkali metal, Alkaline earth metal (1/2), organic amine salt, or hydrogen atom M 1 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 2 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 3 , M 4 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom, respectively)
9.1. ~ 8. A synthetic fiber to which the treatment agent for synthetic fiber according to any one of the above items is attached.
10.1. ~ 8. A method for treating synthetic fibers, which comprises attaching the treatment agent for synthetic fibers according to any one of the above items to the synthetic fibers in an amount of 0.1 to 5% by mass.
本発明の合成繊維用処理剤、合成繊維及び合成繊維の処理方法は、合成繊維の紡糸工程や仮撚工程、後加工工程における近年の高速化にも対応して、優れた制電性により静電気や毛羽を防止できるという効果を発揮するものである。
また、本発明の合成繊維用処理剤は、エマルション安定性に優れるため、エマルションを長時間貯蔵しても含有成分が分離することなく、合成繊維用処理剤を均一に付着させ得るため有用である。
さらに、本発明の合成繊維用処理剤は、氷点下の環境下における低温ハンドリング性に優れるため、合成繊維用処理剤の成分が凝固するなどの問題が生じることがなく、エマルション調製のための仕込みに時間を要することもない。
The treatment agent for synthetic fibers, the treatment method for synthetic fibers and synthetic fibers of the present invention can cope with the recent high speed in the spinning process, false twisting process and post-processing process of synthetic fibers, and is electrostatically charged due to its excellent antistatic property. It has the effect of preventing fluffing and fluffing.
Further, since the treatment agent for synthetic fibers of the present invention is excellent in emulsion stability, it is useful because the treatment agent for synthetic fibers can be uniformly adhered without separating the contained components even if the emulsion is stored for a long time. ..
Further, since the synthetic fiber treatment agent of the present invention has excellent low-temperature handleability in a sub-zero environment, problems such as coagulation of the components of the synthetic fiber treatment agent do not occur, and the preparation for emulsion preparation is carried out. It doesn't take long.
本発明は、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体から選択される１種以上を含有する合成繊維用処理剤や、かかる処理剤が付着した合成繊維及び、かかる合成繊維用処理剤を合成繊維に付着させる処理方法に関する。
以下、本発明について詳細に説明する。
The present invention comprises a synthetic fiber treatment agent containing at least one selected from the cycloalkyl alkanol derivatives represented by the general formulas (1) and (2), synthetic fibers to which such treatment agents are attached, and synthetic fibers. The present invention relates to a treatment method for adhering such a treatment agent for synthetic fibers to synthetic fibers.
Hereinafter, the present invention will be described in detail.
＜シクロアルキルアルカノール誘導体＞
本発明の合成繊維用処理剤は、下記一般式（１）及び下記一般式（２）で示されるシクロアルキルアルカノール誘導体から選択される１種以上を必須成分として含有するものである。
環Ｑａ：炭素数３〜８のシクロアルキレン基
Ｒ１ａ：水素原子又は炭素数１〜１２のアルキル基
Ｒ２ａ：炭素数１〜１２の２価の炭化水素基
Ｒ３：水素原子又は炭素数６〜２２のモノカルボン酸から水酸基を除いた残基
Ａ１ａＯ：炭素数２〜４のアルキレンオキシ基（ただし、当該アルキレンオキシ基が２以上存在する場合は、１種単独又は２種以上でも良い。）
ｍａ：０〜１００の整数、
ただし、ｍ ａ が０でありＲ ３ が水素原子である場合を除く。）
Ｒ４：炭素数４〜１２のジカルボン酸から水酸基を除いた残基、
ただし、ｍ ｂ が０である場合を除く。）
<Cycloalkyl alkanol derivative>
The treatment agent for synthetic fibers of the present invention contains at least one selected from the cycloalkyl alkanol derivatives represented by the following general formula (1) and the following general formula (2) as an essential component.
Ring Q a: cycloalkylene group R 1a having 3 to 8 carbon atoms: alkyl groups R 2a hydrogen atom or 1 to 12 carbon atoms: a divalent hydrocarbon group having 1 to 12 carbon atoms R 3: a hydrogen atom or a carbon atoms Residues obtained by removing hydroxyl groups from 6 to 22 monocarboxylic acids A 1a O: alkyleneoxy groups having 2 to 4 carbon atoms (however, if two or more of the alkyleneoxy groups are present, one type alone or two or more types may be used. good.)
m a: 0~100 of integer,
However, this does not apply when ma is 0 and R 3 is a hydrogen atom. )
R 4 : A residue obtained by removing a hydroxyl group from a dicarboxylic acid having 4 to 12 carbon atoms .
However, this does not apply when mb is 0. )
本発明における上記の一般式（１）に示されるシクロアルキルアルカノール誘導体は、炭素数６〜２２のモノカルボン酸シクロアルキルアルカノールエステル、シクロアルキルアルカノールのアルキレンオキサイド付加重合体又は炭素数６〜２２のモノカルボン酸とシクロアルキルアルカノールのアルキレンオキサイド付加重合体とのエステルであり、本発明における上記の一般式（２）に示されるシクロアルキルアルカノール誘導体は、炭素数４〜１２のジカルボン酸シクロアルキルアルカノールジエステル又は炭素数４〜１２のジカルボン酸とシクロアルキルアルカノールのアルキレンオキサイド付加重合体とのジエステルである。
上記一般式（１）中の環Ｑａ、一般式（２）中の環Ｑｂは、各々独立して炭素数５〜８のシクロアルキル基であることが好ましく、炭素数５又は６のシクロアルキル基であることがより好ましい。
上記一般式（１）のＲ１ａ、一般式（２）中のＲ１ｂは、各々独立して水素原子又は炭素数６〜１０のアルキル基であることが好ましく、水素原子又は炭素数６〜８のアルキル基であることがより好ましく、水素原子であることが特に好ましい。
上記一般式（１）中のＲ２ａ、一般式（２）中のＲ２ｂの炭素数１〜１２の２価の炭化水素基は、各々独立して、直鎖状又は分岐鎖状の何れでも良く、飽和又は不飽和の何れで
も良い。中でも、各々独立して直鎖状又は分岐鎖状の炭素数１〜１２のアルキレン基が好ましく、直鎖状又は分岐鎖状の炭素数２〜８のアルキレン基がより好ましく、直鎖状の炭素数２〜８のアルキレン基が特に好ましい。
上記一般式（１）中のＲ３の水素原子又は炭素数６〜２２のモノカルボン酸から水酸基を除いた残基におけるモノカルボン酸は、飽和モノカルボン酸又は不飽和モノカルボン酸の何れでも良い。中でも、水素原子又は飽和／不飽和炭素数８〜２０のモノカルボン酸から水酸基を除いた残基であることが好ましく、飽和／不飽和炭素数８〜２０のモノカルボン酸から水酸基を除いた残基であることがより好ましい。
上記一般式（２）中のＲ４の炭素数４〜１２のジカルボン酸から２つの水酸基を除いた残基におけるジカルボン酸は、飽和又は不飽和の脂肪族ジカルボン酸、芳香族ジカルボン酸の何れでも良い。中でも、炭素数４〜１２の飽和又は不飽和の脂肪族ジカルボン酸から２つの水酸基を除いた残基が好ましく、炭素数４〜１２の飽和脂肪族ジカルボン酸から２つの水酸基を除いた残基がより好ましい。
上記一般式（１）中のＡ１ａＯ、一般式（２）中のＡ１ｂＯが、炭素数２〜４のアルキレンオキシ基が２種以上である場合は、各々独立して、ランダムに分散されていても、ブロックであっても、それらの混合であってもよい。中でも、各々独立して、炭素数２又は３のアルキレンオキシ基が１種単独又は２種であることが好ましい。
上記一般式（１）中のｍａ、一般式（２）中のｍｂは炭素数２〜４のアルキレンオキシ基の平均モル数を表し、各々独立して、０〜２０の整数が好ましく、０〜１５の整数がより好ましい（ただし、ｍ ａ が０でありＲ ３ が水素原子である場合、ｍ ｂ が０である場合を除く。）。
The cycloalkyl alkanol derivative represented by the above general formula (1) in the present invention is a monocarboxylic acid cycloalkyl alkanol ester having 6 to 22 carbon atoms, an alkylene oxide addition polymer of cycloalkyl alkanol, or a mono having 6 to 22 carbon atoms. An ester of a carboxylic acid and an alkylene oxide addition polymer of a cycloalkyl alkanol, the cycloalkyl alkanol derivative represented by the above general formula (2) in the present invention is a dicarboxylic acid cycloalkyl alkanol diester having 4 to 12 carbon atoms. It is a diester of a dicarboxylic acid having 4 to 12 carbon atoms and an alkylene oxide addition polymer of cycloalkyl alkanol.
Ring Q a in the general formula (1), the general formula (2) Ring Q b in is preferably an cycloalkyl group having 5 to 8 carbon atoms each independently, cycloalkyl of 5 or 6 carbon atoms It is more preferably an alkyl group.
R 1a in the general formula (1), R 1b in formula (2) in is preferably independently a hydrogen atom or an alkyl group having 6 to 10 carbon atoms, the number of hydrogen atoms or carbon 6-8 The alkyl group is more preferable, and the hydrogen atom is particularly preferable.
R 2a in formula (1), the general divalent hydrocarbon group having 1 to 12 carbon atoms in formula (2) in R 2b are each independently either a linear or branched It may be saturated or unsaturated. Among them, linear or branched alkylene groups having 1 to 12 carbon atoms are preferable, linear or branched alkylene groups having 2 to 8 carbon atoms are more preferable, and linear carbons are more preferable. An alkylene group having a number of 2 to 8 is particularly preferable.
Monocarboxylic acids at residue obtained by removing hydroxyl groups from monocarboxylic acids of the above general formula (1) a hydrogen atom or a carbon atoms of R 3 in 6 to 22 may be either a saturated monocarboxylic acid or unsaturated monocarboxylic acid .. Of these, it is preferable that the residue is a hydrogen atom or a monocarboxylic acid having 8 to 20 saturated / unsaturated carbon atoms minus a hydroxyl group, and a residue obtained by removing a hydroxyl group from a monocarboxylic acid having 8 to 20 saturated / unsaturated carbon atoms. It is more preferable that it is a group.
Dicarboxylic acids at residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms R 4 in the general formula (2) in the aliphatic dicarboxylic acids, saturated or unsaturated, either aromatic dicarboxylic acid good. Of these, a residue obtained by removing two hydroxyl groups from a saturated or unsaturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms is preferable, and a residue obtained by removing two hydroxyl groups from a saturated aliphatic dicarboxylic acid having 4 to 12 carbon atoms is preferable. More preferred.
A 1a O in general formula (1), A 1b O in the general formula (2) it is, if there is an alkyleneoxy group having 2 to 4 carbon atoms is 2 or more, each independently, randomly distributed It may be, block, or a mixture of them. Above all, it is preferable that the alkyleneoxy group having 2 or 3 carbon atoms is 1 type alone or 2 types independently.
M a in general formula (1), the m b in the general formula (2) represents the average number of moles of the alkyleneoxy group having 2 to 4 carbon atoms, each independently preferably an integer of 0 to 20, more preferably 0 to 15 integers (where, m a is 0 when R 3 is hydrogen atom, unless m b is 0.).
本発明における、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体は、例えば、シクロアルキルアルカノールとモノカルボン酸又はジカルボン酸とのエステル化反応、シクロアルキルアルカノールに炭素数２〜４のアルキレンオキサイドをランダム、ブロック又はそれらを混合した方法での付加重合、または上記のシクロアルカノールのアルキレンオキサイド付加重合体とモノカルボン酸又はジカルボン酸とのエステル化反応によって製造されるものである。 The cycloalkyl alkanol derivative represented by the general formula (1) and the general formula (2) in the present invention is, for example, an esterification reaction between a cycloalkyl alkanol and a monocarboxylic acid or a dicarboxylic acid, and the cycloalkyl alkanol has 2 carbon atoms. It is produced by random, blocking, or addition polymerization of alkylene oxides of 4 to 4 by a method of mixing them, or by an esterification reaction of the above-mentioned alkylene oxide addition polymer of cycloalkanol with a monocarboxylic acid or a dicarboxylic acid. ..
本発明の合成繊維用処理剤は、その全質量に対して、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体を０．０１〜３０質量％含有することが好ましく、０．１〜２５質量％含有することがより好ましく、０．２〜２０質量％含有することがさらに好ましく、０．２〜１０質量％含有することが特に好ましい。
また、本発明の合成繊維用処理剤は、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体以外の非イオン性界面活性剤及びイオン性界面活性剤を含有することが好ましい。
さらに、本発明の合成繊維用処理剤は、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体以外の非イオン性界面活性剤、平滑剤及びイオン性界面活性剤を含有することが好ましい。
本発明の合成繊維用処理剤に併用できる、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体以外の非イオン性界面活性剤、平滑剤及びイオン性界面活性剤について、説明する。
The treatment agent for synthetic fibers of the present invention preferably contains 0.01 to 30% by mass of the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2) with respect to the total mass thereof. It is more preferably 0.1 to 25% by mass, further preferably 0.2 to 20% by mass, and particularly preferably 0.2 to 10% by mass.
Further, the treatment agent for synthetic fibers of the present invention may contain a nonionic surfactant and an ionic surfactant other than the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2). preferable.
Further, the treatment agent for synthetic fibers of the present invention contains a nonionic surfactant, a smoothing agent and an ionic surfactant other than the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2). It is preferable to do so.
Regarding nonionic surfactants, smoothing agents and ionic surfactants other than the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2), which can be used in combination with the treatment agent for synthetic fibers of the present invention. explain.
＜シクロアルキルアルカノール誘導体以外の非イオン性界面活性剤＞
本発明における合成繊維用処理剤に併用できる、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体以外の非イオン性界面活性剤としては、特に制限はなく、例えば（１）ポリオキシエチレンオレアート、ポリオキシエチレンメチルエーテルラウラート、ポリオキシエチレンオクチルエーテルラウラート、ポリオキシエチレンポリオキシプロピレントリデシルエーテルパルミタート、ポリオキシエチレンジオレアート、ポリオキシエチレンラウリルエーテル、ポリオキシプロピレンラウリルエーテルメチルエーテル、ポリオキシブチレンオレイルエーテル、ポリオキシエチレンポリオキシプロピレンブチルエーテル、ポリオキシエチレンポリオキシプロピレンオクチルエーテル、ポリオキシエチレンポリオキシプロピレントリメチロールプロピルエーテル、ポリオキシエチレンポリオキシプロピレンノニルエーテル、ポリオキシエチレンポリオキシプロピレンプロピレングリコールエーテル、ポリオキシエチレンポリオキシプロピレンラウリルエーテル、ポリオキシエチレンポリオキシプロピレンイソトリデシルエーテル、ポリオキシエチレンテトラデシルエーテル、ポリオキシエチレングリセリルエーテル、ポリオキシエチレンラウリルアミノエーテル、ポリオキシエチレンラウロアミドエーテル等の、有機酸、有機アルコール、有機アミン及び／又は有機アミド分子に炭素数２〜４のアルキレンオキサイドを付加した化合物、（２）ポリオキシアルキレンソルビタントリオレアート、ポリオキシアルキレンヒマシ油エーテル、ポリオキシアルキレン硬化ヒマシ油エーテル、ポリオキシアルキレン硬化ヒマシ油エーテルトリオレアート等のポリオキシアルキレン多価アルコール脂肪酸エステル、（３）ジエタノールアミンモノラウロアミド等のアルキルアミド、（４）ポリオキシエチレンジエタノールアミンモノオレイルアミド等のポリオキシアルキレン脂肪酸アミド等が挙げられる。これらの非イオン性界面活性剤は、１種を単独で使用してもよく、２種以上を組み合わせて使用してもよい。本発明では、化合物名の末端にＥＯおよびＰＯと記載したものは、それぞれエチレンオキサイドおよびプロピレンオキサイドの付加物を意味し、後に続く数字はその付加モル数を示す。ＥＯおよびＰＯの後に記載された数値はそれぞれの平均付加モル数を意味する。
<Nonionic surfactants other than cycloalkyl alkanol derivatives>
The nonionic surfactant other than the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2), which can be used in combination with the treatment agent for synthetic fibers in the present invention, is not particularly limited, and is not particularly limited, for example, (1). ) Polyoxyethylene oleate, polyoxyethylene methyl ether laurate, polyoxyethylene octyl ether laurate, polyoxyethylene polyoxypropylene tridecyl ether palmitate, polyoxyethylene dioreato, polyoxyethylene lauryl ether, polyoxy Polyoxyethylene polyoxypropylene oleyl ether, polyoxybutylene oleyl ether, polyoxyethylene polyoxypropylene butyl ether, polyoxyethylene polyoxypropylene octyl ether, polyoxyethylene polyoxypropylene trimethylolpropyl ether, polyoxyethylene polyoxypropylene nonyl ether, poly Oxyethylene polyoxypropylene propylene glycol ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene isotridecyl ether, polyoxyethylene tetradecyl ether, polyoxyethylene glyceryl ether, polyoxyethylene laurylamino ether, poly Compounds such as oxyethylene lauroamide ether obtained by adding an alkylene oxide having 2 to 4 carbon atoms to an organic acid, an organic alcohol, an organic amine and / or an organic amide molecule, (2) polyoxyalkylene sorbitan trioleate, polyoxyalkylene himeshi. Polyoxyalkylene polyhydric alcohol fatty acid ester such as oil ether, polyoxyalkylene cured castor oil ether, polyoxyalkylene cured castor oil ether trioleate, (3) diethanolamine alkylamide such as monolauroamide, (4) polyoxyethylene diethanolamine Examples thereof include polyoxyalkylene fatty acid amides such as monooleyl amides. These nonionic surfactants may be used alone or in combination of two or more. In the present invention, EO and PO at the end of the compound name mean an adduct of ethylene oxide and propylene oxide, respectively, and the number following the compound indicates the number of adducts thereof. The numbers after EO and PO mean the average number of moles added respectively.
＜シクロアルキルアルカノール誘導体以外の平滑剤＞
本発明の合成繊維用処理剤に併用できる、上記一般式（１）及び一般式（２）で示されるシクロアルキルアルカノール誘導体以外の平滑剤としては、（１）ブチルステアラート、オクチルステアラート、オレイルラウラート、オレイルオレアート、イソペンタコサニルイソステアラート、オクチルパルミタート、イソトリデシルステアラート、ラウリルオクタート等の、脂肪族モノアルコールと脂肪族モノカルボン酸とのエステル化合物、（２）１，６−ヘキサンジオールジデカノアート、トリメチロールプロパンモノオレアートモノラウラート、ソルビタントリオレアート、ソルビタンモノオレアート、ソルビタントリステアラート、ソルビタンジステアラート、ソルビタンモノステアラート、グリセリンモノラウラート等の、脂肪族多価アルコールと脂肪族モノカルボン酸とのエステル化合物、（３）ジラウリルアジパート、ジオレイルアゼラート、ジイソセチルチオジプロピオナート、ビスポリオキシエチレンラウリルアジパート等の、脂肪族モノアルコールと脂肪族多価カルボン酸とのエステル化合物、（４）ベンジルオレアート、ベンジルラウラート及びポリオキシプロピレンベンジルステアラート等の、芳香族モノアルコールと脂肪族モノカルボン酸とのエステル化合物、（５）ビスフェノールＡジラウラート、ポリオキシエチレンビスフェノールＡジラウラート等の、芳香族多価アルコールと脂肪族モノカルボン酸とのエステル化合物、（６）ビス２−エチルヘキシルフタラート、ジイソステアリルイソフタラート、トリオクチルトリメリタート等の、脂肪族モノアルコールと芳香族多価カルボン酸とのエステル化合物、（７）ヤシ油、ナタネ油、ヒマワリ油、大豆油、ヒマシ油、ゴマ油、魚油及び牛脂等の天然油脂、（８）鉱物油等、合成繊維用処理剤に採用されている公知の平滑剤が挙げられる。これらの平滑剤成分は、１種を単独で使用してもよく、２種以上を組み合わせて使用してもよい。
<Smoothing agents other than cycloalkyl alkanol derivatives>
Examples of smoothing agents other than the cycloalkylalkanol derivatives represented by the above general formulas (1) and (2) that can be used in combination with the treatment agent for synthetic fibers of the present invention include (1) butyl stealert, octyl stealant, and oleyl. Ester compounds of aliphatic monoalcohols and aliphatic monocarboxylic acids such as laurat, oleyloleate, isopentacosanyl isosteert, octyl palmitate, isotridecylstealto, lauryl octato, etc., (2) 1 , 6-Hexanediol Gidecanoart, Trimethylol Propanemonooleart Monolaurate, Solbitan Trioleart, Solbitan Monooleart, Solbitan Triste Alert, Solbitan Disteaert, Solbitan Monosteertert, Glycerin Monolaurate, etc. Ester compounds of group polyhydric alcohols and aliphatic monocarboxylic acids, (3) aliphatic monoalcohols such as dilauryl adipate, diolayl azelate, diisocetylthiodipropionate, bispolyoxyethylene lauryl adipate, etc. And an ester compound of an aliphatic polyhydric carboxylic acid, (4) an ester compound of an aromatic monoalcohol and an aliphatic monocarboxylic acid such as benzyloleate, benzyllaurat and polyoxypropylene benzyl steerant, (5). Ester compounds of aromatic polyhydric alcohols and aliphatic monocarboxylic acids such as bisphenol A dilaurate and polyoxyethylene bisphenol A dilaurate, (6) bis2-ethylhexylphthalate, diisostearylisophthalate, trioctyl remeritate. , Etc., ester compounds of aliphatic monoalcohols and aromatic polyhydric carboxylic acids, (7) natural fats and oils such as palm oil, rapeseed oil, sunflower oil, soybean oil, sunflower oil, sesame oil, fish oil and beef fat, (8). Examples thereof include known smoothing agents used as treatment agents for synthetic fibers such as mineral oils. These smoothing agent components may be used alone or in combination of two or more.
＜イオン性界面活性剤＞
本発明の合成繊維用処理剤は、下記の一般式（３）で示される有機リン酸エステルＰ１、下記の一般式（４）で示される有機リン酸エステルＰ２、及び下記の一般式（５）で示される有機リン酸エステルＰ３から選ばれる少なくとも１つの有機リン酸エステルをイオン性界面活性剤として併用することが好ましい。
ｎ：２〜４の整数
Ｒ５：「Ｒ１ｃ−環Ｑｃ−Ｒ２ｃ−Ｏ−（Ａ１ｃＯ）ｍｃ−」から末端の酸素原子を除いた残基（ただし、環Ｑｃ、Ｒ１ｃ、Ｒ２ｃ、Ａ１ｃＯ、ｍｃは、一般式（１）の環Ｑａ、Ｒ１ａ、Ｒ２ａ、Ａ１ａＯ、ｍａと各々独立して同じ意味である。）、アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子
Ｍ１：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ２：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ３、Ｍ４：各々独立してアルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
<Ionic surfactant>
The treatment agent for synthetic fibers of the present invention has the organic phosphate ester P1 represented by the following general formula (3), the organic phosphate ester P2 represented by the following general formula (4), and the following general formula (5). It is preferable to use at least one organic phosphoric acid ester selected from the organic phosphoric acid ester P3 shown in (1) in combination as an ionic surfactant.
n: Integer of 2 to 4 R 5 : Residue excluding the terminal oxygen atom from "R 1c -ring Q c- R 2c -O- (A 1c O) m c- " (however, ring Q c , R 1c, R 2c, a 1c O , m c is a ring Q a in the general formula (1), R 1a, R 2a, a 1a O, m a and each independently the same meaning.), alkali metal, Alkaline earth metal (1/2), organic amine salt, or hydrogen atom M 1 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 2 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 3 , M 4 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom, respectively)
上記一般式（３）中の環Ｑｃ、Ｒ１ｃ、Ｒ２ｃ、Ａ１ｃＯ、ｍｃ、上記一般式（４）中の環Ｑｄ、Ｒ１ｄ、Ｒ２ｄ、Ａ１ｄＯ（ＯＡ１ｄ）、ｍｄ、上記一般式（５）中の環Ｑｅ、Ｒ１ｅ、Ｒ２ｅ、Ａ１ｅＯ、ｍｅの好適例は、各々独立して、一般式（１）の環Ｑａ、Ｒ１ａ、Ｒ２ａ、Ａ１ａＯ、ｍａと同じである。
上記一般式（３）中のＲ５は、「Ｒ１ｃ−環Ｑｃ−Ｒ２ｃ−Ｏ−（Ａ１ｃＯ）ｍｃ−」から末端の酸素原子を除いた残基（ただし、環Ｑｃ、Ｒ１ｃ、Ｒ２ｃ、Ａ１ｃＯ、ｍｃは、一般式（１）の環Ｑａ、Ｒ１ａ、Ｒ２ａ、Ａ１ａＯ、ｍａと各々独立して同じ意味である。）であることが好ましい。
上記一般式（３）中のＭ１、上記一般式（４）中のＭ２、上記一般式（５）中のＭ３、Ｍ４は、各々独立してアルカリ金属又は有機アミン塩であることが好ましい。
Ring Q c in the general formula (3), R 1c, R 2c, A 1c O, m c, ring Q d in the general formula (4), R 1d, R 2d, A 1d O (OA 1d) , preferred examples of m d, ring Q e in the general formula (5), R 1e, R 2e, a 1e O, m e are each independently formula (1) ring Q a, R 1a is the same as R 2a, a 1a O, m a.
R 5 in the above general formula (3) is a residue obtained by removing the terminal oxygen atom from "R 1c -ring Q c- R 2c- O- (A 1c O) m c- " (however, ring Q c). , R 1c, R 2c, a 1c O, m c is a ring Q a in the general formula (1), R 1a, R 2a, an a 1a O, m a and each independently the same meaning.) Is preferable.
M 1 in the general formula (3), M 2 in the general formula (4), and M 3 and M 4 in the general formula (5) are independently alkali metals or organic amine salts. Is preferable.
上記一般式（３）で示される有機リン酸エステルＰ１、上記一般式（４）で示される有機リン酸エステルＰ２、及び、上記一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率の合計を１００％とする。このとき、一般式（５）で示され
る有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率は、３０〜８０％であり、３５〜７５％であることが更によく、４０〜７０％であることが特によい。
It belongs to the organic phosphoric acid ester P1 represented by the general formula (3), the organic phosphoric acid ester P2 represented by the general formula (4), and the organic phosphoric acid ester P3 represented by the general formula (5). The total of P-nuclear NMR integration ratios is 100%. At this time, the P-nuclear NMR integral ratio attributable to the organic phosphate ester P3 represented by the general formula (5) is 30 to 80%, more preferably 35 to 75%, and 40 to 70%. It is especially good to have.
Ｐ核ＮＭＲ積分比率（有機リン酸エステルＰ１、Ｐ２、Ｐ３から帰属されるＰ核ＮＭＲの積分比率（％））は、有機リン酸エステルのアルカリ金属塩等に過剰のＫＯＨを加えてｐＨを１２以上にした条件下で、３１Ｐ−ＮＭＲ（ＶＡＬＩＡＮ社製の商品名ＭＥＲＣＵＲＹ ｐｌｕｓ ＮＭＲ Ｓｐｅｃｔｒｏｍｅｔｏｒ Ｓｙｓｔｅｍ、３００ＭＨｚ）に供したときの測定値を用いて、下記の式（ａ）〜式（ｃ）に基づいて算出することができる値を意味する。なお、溶媒は重水／テトラヒドロフラン＝８／２（体積比）の混合溶媒を用いることができる。
なお、式（ａ）〜式（ｃ）中、「Ｐ化１」は、一般式（３）で示される有機リン酸エステルＰ１に帰属されるＰ核ＮＭＲ積分値を、「Ｐ化２」は、一般式（４）で示される有機リン酸エステルＰ２に帰属されるＰ核ＮＭＲ積分値を、「Ｐ化３」は、一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分値を示す。
The P-nuclear NMR integration ratio (integration ratio (%) of P-nuclear NMR attributed from organic phosphate esters P1, P2, P3) is such that the pH is adjusted to 12 by adding excess KOH to the alkali metal salt of the organic phosphate ester. Based on the following formulas (a) to (c), using the measured values when subjected to 31 P-NMR (trade name MERCURY plus NMR Spectrometer System, 300 MHz manufactured by VALUE) under the above conditions. Means a value that can be calculated. As the solvent, a mixed solvent of heavy water / tetrahydrofuran = 8/2 (volume ratio) can be used.
In the formulas (a) to (c), "P-formation 1" is the P-nuclear NMR integrated value attributed to the organic phosphate ester P1 represented by the general formula (3), and "P-formation 2" is. , P-nuclear NMR integrated value attributed to the organic phosphate ester P2 represented by the general formula (4), and "P-formation 3" is P assigned to the organic phosphate ester P3 represented by the general formula (5). The nuclear NMR integrated value is shown.
［数１］
有機リン酸エステルＰ１のＰ核ＮＭＲ積分比率（％）＝（Ｐ化１）÷（Ｐ化１＋Ｐ化２＋Ｐ化３）×１００・・・（ａ）
［数２］
有機リン酸エステルＰ２のＰ核ＮＭＲ積分比率（％）＝（Ｐ化２）÷（Ｐ化１＋Ｐ化２＋Ｐ化３）×１００・・・（ｂ）
［数３］
有機リン酸エステルＰ３のＰ核ＮＭＲ積分比率（％）＝（Ｐ化３）÷（Ｐ化１＋Ｐ化２＋Ｐ化３）×１００・・・（ｃ）
本発明における、上記一般式（３）〜（５）で示される有機リン酸エステルの製造方法は特に制限されないが、例えば、シクロアルキルアルカノール、又はシクロアルキルアルカノールに炭素数２〜４のアルキレンオキサイドをランダム、ブロック又はそれらを混合した方法で付加重合させたものと、無水リン酸に代表されるリン酸化剤とを混合しエステル化して製造されるもの、またはさらにそれを塩基で中和することによって製造されるものである。
[Number 1]
P-nuclear NMR integral ratio (%) of organic phosphate ester P1 = (P-formation 1) ÷ (P-formation 1 + P-formation 2 + P-formation 3) × 100 ... (a)
[Number 2]
P-nuclear NMR integral ratio (%) of organic phosphate ester P2 = (P-formation 2) ÷ (P-formation 1 + P-formation 2 + P-formation 3) × 100 ... (b)
[Number 3]
P-nuclear NMR integral ratio (%) of organic phosphate ester P3 = (P-formation 3) ÷ (P-formation 1 + P-formation 2 + P-formation 3) × 100 ... (c)
The method for producing the organic phosphoric acid ester represented by the above general formulas (3) to (5) in the present invention is not particularly limited, and for example, cycloalkyl alkanol or alkylene oxide having 2 to 4 carbon atoms is added to cycloalkyl alkanol. It is produced by mixing and esterifying a phosphoric acid typified by anhydrous phosphoric acid with a random, block or a mixture thereof, or by neutralizing it with a base. It is manufactured.
＜その他のイオン性界面活性剤＞
本発明の合成繊維用処理剤は、さらにその他のイオン性界面活性剤を含んでいてもよく、繊維用処理剤として使用される公知のアニオン性界面活性剤、カチオン性界面活性剤、両性界面活性剤等が挙げられる。具体的には、例えば、アニオン性界面活性剤としては、（１）酢酸カリウム塩、オクタン酸カリウム塩、オレイン酸カリウム塩、オレイン酸ナトリウム塩、アルケニルコハク酸カリウム塩等のカルボン酸石鹸型イオン性界面活性剤、（２）２級アルカンスルホン酸ナトリウム塩、ドデシルベンゼンスルホン酸ナトリウム塩、ジオクチルスルホコハク酸ナトリウム塩等のスルホン酸エステル型イオン性界面活性剤、（３）ポリオキシエチレンラウリル硫酸エステルナトリウム塩、ヘキサデシル硫酸カリウム塩、牛脂硫化油、ヒマシ油硫化油等の硫酸エステル型イオン性界面活性剤、（４）ドデシルリン酸エステルナトリウム塩、オレイルリン酸エステルカリウム塩、ヘキサデシルリン酸エステルカリウム塩、オクタデシルリン酸エステルカリウム塩、オレイルリン酸エステルトリエタノールアミン塩、ポリオキシエチレンオレイルエーテルリン酸エステルとポリオキシエチレンラウリルアミノエーテルとの塩等の有機リン酸エステル塩等が挙げられる。またカチオン性界面活性剤としては、テトラブチルアンモニウム塩等の第４級アンモニウム塩等が挙げられ、両性界面活性剤としては、ジメチルステアリルアミンオキサイド等の有機アミンオキサイド、オクチルジメチルアンモニオアセタート等のベタイン型両性界面活性剤、Ｎ，Ｎ−ビス（２−カルボキシエチル）−オクチルアミンナトリウム等のアラニン型両性界面活性剤等が挙げられる。これらの成分は、１種を単独で使用してもよく
、２種以上を組み合わせて使用してもよい。
<Other ionic surfactants>
The treatment agent for synthetic fibers of the present invention may further contain other ionic surfactants, and is known as an anionic surfactant, a cationic surfactant, or an amphoteric surfactant used as a treatment agent for fibers. Agents and the like can be mentioned. Specifically, for example, examples of the anionic surfactant include (1) carboxylic acid soap-type ionic salts such as potassium acetate salt, potassium octanoate salt, potassium oleate salt, sodium oleate salt, and potassium alkenyl succinate salt. Surfactant, (2) sulfonic acid ester type ionic surfactant such as secondary alkane sulfonic acid sodium salt, dodecylbenzene sulfonic acid sodium salt, dioctyl sulfosuccinate sodium salt, (3) polyoxyethylene lauryl sulfate sodium salt , Hexadecyl sulfate potassium salt, beef fat sulfide oil, castor oil sulfide oil and other sulfate ester type ionic surfactants, (4) dodecyl phosphate sodium salt, oleyl phosphate potassium salt, hexadecyl phosphate potassium salt, octadecyllin Examples thereof include acid ester potassium salt, oleyl phosphate ester triethanolamine salt, and organic phosphate ester salt such as a salt of polyoxyethylene oleyl ether phosphate and polyoxyethylene lauryl amino ether. Examples of the cationic surfactant include quaternary ammonium salts such as tetrabutylammonium salt, and examples of the amphoteric surfactant include organic amine oxides such as dimethylstearylamine oxide and octyldimethylammonioacetate. Examples thereof include betaine-type amphoteric surfactants and alanine-type amphoteric surfactants such as N, N-bis (2-carboxyethyl) -octylamine sodium. These components may be used alone or in combination of two or more.
本発明の合成繊維用処理剤において、上記一般式（１）及び上記一般式（２）で示されるシクロアルキルアルカノール誘導体と、それ以外の非イオン性界面活性剤及びイオン性界面活性剤を含有する場合、合成繊維用処理剤の全質量に対して、それ以外の非イオン性界面活性剤は５０〜９９質量％含有することが好ましく、６０〜９９質量％含有することがより好ましく、６５〜９９質量％含有することがさらに好ましく、それ以外のイオン性界面活性剤は０．０１〜１０質量％含有することが好ましく、０．１〜１０質量％含有することがより好ましく、０．５〜５質量％含有することがさらに好ましい。
上記イオン性界面活性剤として、上記一般式（３）で示される有機リン酸エステルＰ１、上記一般式（４）で示される有機リン酸エステルＰ２、及び、上記一般式（５）で示される有機リン酸エステルＰ３から選ばれる少なくとも１つの有機リン酸エステルを含有する場合、上記一般式（３）〜（５）示される有機リン酸エステルの総量は、合成繊維用処理剤の全質量に対して０．０１〜１０質量％含有することが好ましく、０．０５〜５質量％含有することがより好ましく、０．１〜３質量％含有することがさらに好ましい。
The treatment agent for synthetic fibers of the present invention contains the cycloalkyl alkanol derivatives represented by the above general formulas (1) and (2), and other nonionic surfactants and ionic surfactants. In this case, the other nonionic surfactant is preferably contained in an amount of 50 to 99% by mass, more preferably 60 to 99% by mass, and 65 to 99% by mass, based on the total mass of the treatment agent for synthetic fibers. It is more preferably contained in an amount of 0.1% by mass, and the other ionic surfactant is preferably contained in an amount of 0.01 to 10% by mass, more preferably 0.1 to 10% by mass, and 0.5 to 5%. It is more preferably contained in% by mass.
As the ionic surfactant, the organic phosphate ester P1 represented by the general formula (3), the organic phosphate ester P2 represented by the general formula (4), and the organic represented by the general formula (5). When at least one organic phosphoric acid ester selected from the phosphoric acid ester P3 is contained, the total amount of the organic phosphoric acid esters represented by the above general formulas (3) to (5) is based on the total mass of the synthetic fiber treatment agent. It is preferably contained in an amount of 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and even more preferably 0.1 to 3% by mass.
本発明の合成繊維用処理剤において、上記一般式（１）及び上記一般式（２）で示されるシクロアルキルアルカノール誘導体と、前記シクロアルキルアルカノール誘導体以外の非イオン性界面活性剤、平滑剤、及びイオン性界面活性剤を含有する場合、それ以外の非イオン性界面活性剤は５〜６０質量％含有することが好ましく、１０〜６０質量％含有することがより好ましく、１０〜５０質量％含有することがさらに好ましく、それ以外の平滑剤は、３０〜８０質量％含有することが好ましく、３０〜７０質量％含有することがより好ましく、４０〜７０質量％含有することがさらに好ましく、それ以外のイオン性界面活性剤は０．１〜２５質量％含有することが好ましく、０．５〜２０質量％含有することがより好ましく、１．０〜１５質量％含有することがさらに好ましい。
上記イオン性界面活性剤として、上記一般式（３）で示される有機リン酸エステルＰ１、上記一般式（４）で示される有機リン酸エステルＰ２、及び、上記一般式（５）で示される有機リン酸エステルＰ３から選ばれる少なくとも１つの有機リン酸エステルを含有する場合、上記一般式（３）〜（５）示される有機リン酸エステルの総量は、合成繊維用処理剤の全質量に対して０．０１〜１０質量％含有することが好ましく、０．０５〜５質量％含有することがより好ましく、０．１〜３質量％含有することがさらに好ましい。
この組成の合成繊維用処理剤は、紡糸−延伸工程に用いる合成繊維用処理剤として好適である。
In the treatment agent for synthetic fibers of the present invention, the cycloalkyl alkanol derivative represented by the above general formula (1) and the above general formula (2), a nonionic surfactant other than the cycloalkyl alkanol derivative, a smoothing agent, and a smoothing agent, and When the ionic surfactant is contained, the other nonionic surfactant is preferably contained in an amount of 5 to 60% by mass, more preferably 10 to 60% by mass, and more preferably 10 to 50% by mass. It is more preferable, and the other smoothing agent is preferably contained in an amount of 30 to 80% by mass, more preferably 30 to 70% by mass, further preferably 40 to 70% by mass, and other than that. The ionic surfactant is preferably contained in an amount of 0.1 to 25% by mass, more preferably 0.5 to 20% by mass, and even more preferably 1.0 to 15% by mass.
As the ionic surfactant, the organic phosphate ester P1 represented by the general formula (3), the organic phosphate ester P2 represented by the general formula (4), and the organic represented by the general formula (5). When at least one organic phosphoric acid ester selected from the phosphoric acid ester P3 is contained, the total amount of the organic phosphoric acid esters represented by the above general formulas (3) to (5) is based on the total mass of the synthetic fiber treatment agent. It is preferably contained in an amount of 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and even more preferably 0.1 to 3% by mass.
The synthetic fiber treatment agent having this composition is suitable as a synthetic fiber treatment agent used in the spinning-drawing step.
＜その他の成分＞
本発明の合成繊維用処理剤は、本発明の効果を阻害しない範囲内において、処理剤の品質保持のための安定化剤や制電剤、消泡剤（シリコーン系化合物、鉱物油等）、つなぎ剤、酸化防止剤、紫外線吸収剤等の通常合成繊維の処理剤に用いられる成分をさらに配合してもよい。
<Other ingredients>
The treatment agent for synthetic fibers of the present invention is a stabilizer, an antistatic agent, an antifoaming agent (silicone compound, mineral oil, etc.) for maintaining the quality of the treatment agent, as long as the effect of the present invention is not impaired. Ingredients usually used in synthetic fiber treatment agents such as binders, antioxidants, and UV absorbers may be further added.
＜合成繊維＞
本発明の合成繊維は、本発明の合成繊維用処理剤が付着している合成繊維である。本発明の合成繊維用処理剤を付着させる合成繊維としては、特に制限はないが、例えば（１）ポリエチレンテレフタラート、ポリプロピレンテレフタラート、ポリ乳酸エステル等のポリエステル系繊維、（２）ナイロン６、ナイロン６６等のポリアミド系繊維、（３）ポリアクリル、モダアクリル等のポリアクリル系繊維、（４）ポリエチレン、ポリプロピレン等のポリオレフィン系繊維、ポリウレタン系繊維等が挙げられる。なかでもポリエステル系繊維、ポリアミド系繊維に付着させる場合に効果の発現が高い。
本発明の合成繊維用処理剤を合成繊維に付着させる割合は、特に制限はないが、本発明の合成繊維用処理剤を合成繊維に対し０．１〜３質量％の割合となるよう付着させること
が好ましく、０．３〜１．２質量％の割合となるよう付着させることがより好ましい。かかる構成により、本発明の効果をより向上させる。
また、本発明の合成繊維用処理剤を付着させる工程としては、特に制限はなく、例えば、紡糸工程、紡糸と延伸とを同時に行なう工程等が挙げられる。また、本発明の処理剤を合成繊維に付着させる方法としては、ローラー給油法、計量ポンプを用いたガイド給油法、浸漬給油法、スプレー給油法等が挙げられる。さらに、本発明の処理剤を合成繊維に付着させる際の形態としては、ニート、有機溶剤溶液、水性液等が挙げられるが、水性液が好ましい。本発明の処理剤の水性液を付着させる場合も、合成繊維に対し本発明の処理剤として０．１〜３質量％、好ましくは０．３〜１．２質量％となるよう付着させると良い。
<Synthetic fiber>
The synthetic fiber of the present invention is a synthetic fiber to which the processing agent for synthetic fiber of the present invention is attached. The synthetic fiber to which the treatment agent for synthetic fibers of the present invention is attached is not particularly limited, and is, for example, (1) polyester fibers such as polyethylene terephthalate, polypropylene terephthalate, and polylactic acid ester, (2) nylon 6, nylon. Examples thereof include polyamide fibers such as 66, (3) polyacrylic fibers such as polyacrylic and modal acrylic, (4) polyolefin fibers such as polyethylene and polypropylene, and polyurethane fibers. In particular, the effect is highly exhibited when it is attached to polyester fibers and polyamide fibers.
The ratio of the synthetic fiber treatment agent of the present invention to the synthetic fiber is not particularly limited, but the synthetic fiber treatment agent of the present invention is attached to the synthetic fiber at a ratio of 0.1 to 3% by mass. It is preferable, and it is more preferable to attach the fibers so that the ratio is 0.3 to 1.2% by mass. With such a configuration, the effect of the present invention is further improved.
Further, the step of adhering the processing agent for synthetic fibers of the present invention is not particularly limited, and examples thereof include a spinning step, a step of performing spinning and drawing at the same time, and the like. Moreover, as a method of adhering the treatment agent of this invention to a synthetic fiber, a roller refueling method, a guide refueling method using a measuring pump, a dip refueling method, a spray refueling method and the like can be mentioned. Further, examples of the form for adhering the treatment agent of the present invention to the synthetic fiber include neat, an organic solvent solution, an aqueous solution, and the like, but an aqueous solution is preferable. Even when the aqueous solution of the treatment agent of the present invention is attached, it is preferable to attach the treatment agent of the present invention to the synthetic fiber in an amount of 0.1 to 3% by mass, preferably 0.3 to 1.2% by mass. ..
本発明の合成繊維用処理剤は、上記一般式（１）及び上記一般式（２）で示されるシクロアルキルアルカノール誘導体を必須成分として含有することにより、合成繊維の紡糸工程や仮撚工程、後加工工程における近年の高速化にも対応して、静電気や毛羽の発生を充分に防止することができる。
また、本発明の合成繊維用処理剤は、エマルション安定性に優れるため、長時間貯蔵しても含有成分が分離することなく、さらに、氷点下の環境下における低温ハンドリング性に優れるため、合成繊維用処理剤の成分が凝固するなどの問題が生じることがないため、合成繊維用処理剤が均一に付着させ、十分に機能を発揮させ得るために有用であり、エマルション調製のための仕込みに時間を要することもない。
The treatment agent for synthetic fibers of the present invention contains the cycloalkyl alkanol derivatives represented by the above general formulas (1) and the above general formula (2) as essential components, whereby the synthetic fiber spinning step, false twisting step, and post. It is possible to sufficiently prevent the generation of static electricity and fluff in response to the recent increase in speed in the processing process.
In addition, the treatment agent for synthetic fibers of the present invention has excellent emulsion stability, so that the contained components do not separate even when stored for a long time, and further, it has excellent low-temperature handleability in a sub-zero environment, so that it is used for synthetic fibers. Since there is no problem such as coagulation of the components of the treatment agent, it is useful for the treatment agent for synthetic fibers to be uniformly adhered and to fully exert its function, and it takes time to prepare the emulsion. It doesn't need to be.
以下、実施例を挙げて本発明を説明するが、本発明の技術範囲はこれらにより限定されるものではない。なお、以下の実施例及び比較例において、部は質量部を、また％は質量％を意味する。 Hereinafter, the present invention will be described with reference to examples, but the technical scope of the present invention is not limited thereto. In the following Examples and Comparative Examples, "parts" means "parts by mass" and "%" means "% by mass".
＜シクロアルキルアルカノール誘導体の合成＞
（Ａ−１）
反応容器に、６−シクロヘキシルヘキシルアルコール１８４ｇ及びオレイン酸２８２ｇを仕込み、窒素ガス下に７５℃で溶融した後、触媒としてパラトルエンスルホン酸０．６ｇを加え、１２０℃で２ｍｍＨｇの減圧下で生成する水を反応系外に排出させながら４時間反応させた。次いで、窒素ガス存在下において１０５℃で常圧に戻し、吸着剤を添加して触媒を処理し、９０℃で濾過することでＡ−１を得た。
この「Ａ−１」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘキシレン基、Ｒ３はオレオイル基、ｍａは０であるシクロアルキルアルカノール化合物である。また「Ａ−１」の純度は、本発明のシクロアルキルアルカノール誘導体として、ガスクロマトグラフィー質量分析法（以下、「ＧＣ−ＭＳ」という。）の測定により９９％であることを確認した。
<Synthesis of cycloalkyl alkanol derivative>
(A-1)
184 g of 6-cyclohexylhexyl alcohol and 282 g of oleic acid are charged in a reaction vessel, melted under nitrogen gas at 75 ° C., and then 0.6 g of p-toluenesulfonic acid is added as a catalyst to produce the product at 120 ° C. under reduced pressure of 2 mmHg. The reaction was carried out for 4 hours while draining water out of the reaction system. Then, the pressure was returned to normal pressure at 105 ° C. in the presence of nitrogen gas, an adsorbent was added to treat the catalyst, and filtration was performed at 90 ° C. to obtain A-1.
Cycloalkyl This "A-1" is ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is hexylene, R 3 is oleoyl group, is m a is 0 It is an alkylalkanol compound. Further, it was confirmed that the purity of "A-1" was 99% as the cycloalkyl alkanol derivative of the present invention by measurement by gas chromatography-mass spectrometry (hereinafter referred to as "GC-MS").
（Ａ−２）
上記「Ａ−１」の製造方法において、６−シクロヘキシルヘキシルアルコールに代えて、７−シクロヘキシルへプチルアルコールを１９８ｇ使用した以外は同じようにして、Ａ−２を得た。
この「Ａ−２」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘプチレン基、Ｒ３はオレオイル基、ｍａは０であるシクロアルキルアルカノール化合物である。また「Ａ−２」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により９８％であることを確認した。
(A-2)
A-2 was obtained in the same manner as in the above-mentioned production method of "A-1" except that 198 g of 7-cyclohexylheptyl alcohol was used instead of 6-cyclohexylhexyl alcohol.
Cycloalkyl This "A-2" is the ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is a heptylene group, R 3 is oleoyl group, is m a is 0 It is an alkylalkanol compound. Further, it was confirmed that the purity of "A-2" was 98% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−３）
７−シクロヘキシルヘプチルアルコール１９８ｇをオートクレーブに仕込み、触媒とし
て水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してエチレンオキサイド１３２ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成したリン酸カリウムを濾別して、７−シクロヘキシルヘプチルアルコールのエチレンオキサイド付加重合物を得た。
得られた付加重合物のうち１６５ｇと、オレイン酸１４１ｇを窒素ガス存在下において７５℃で溶融した後、触媒としてパラトルエンスルホン酸０．３ｇを加え、１２０℃で２ｍｍＨｇの減圧下で生成する水を反応系外に排出させながら４時間反応させた。次いで窒素ガス存在下において１０５℃で常圧に戻し、吸着剤を添加して触媒を処理し、９０℃で濾過することでＡ−３を得た。
この「Ａ−３」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘプチレン基、Ｒ３はオレオイル基、Ａ１ａＯはＥＯ（エチレンオキシ基）、ｍａは３であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−３」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により９７％であることを確認した。
(A-3)
198 g of 7-cyclohexylheptyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 132 g of ethylene oxide was press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain an ethylene oxide addition polymer of 7-cyclohexylheptyl alcohol.
After melting 165 g of the obtained addition polymer and 141 g of oleic acid at 75 ° C. in the presence of nitrogen gas, 0.3 g of p-toluenesulfonic acid is added as a catalyst, and water produced at 120 ° C. under a reduced pressure of 2 mmHg. Was reacted for 4 hours while being discharged from the reaction system. Then, the pressure was returned to normal pressure at 105 ° C. in the presence of nitrogen gas, an adsorbent was added to treat the catalyst, and filtration was performed at 90 ° C. to obtain A-3.
In this "A-3", the ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is a heptylene group, R 3 is an oleoil group, and A 1 a O is EO (ethylene). oxy group), m a is cycloalkyl alkanol derivative compound is 3. Further, it was confirmed that the purity of "A-3" was 97% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−４）
上記「Ａ−３」の製造方法において、７−シクロヘキシルヘプチルアルコールに代えて、６−シクロヘキシルへキシルアルコールを１８４ｇ使用し、エチレンオキサイド１３２ｇに代えて、エチレンオキサイド２６４ｇ、プロピレンオキサイド１１６ｇを使用し、オレイン酸１４１ｇに代えて、オクタン酸８２ｇを使用した以外は同じようにして、Ａ−４を得た。
この「Ａ−４」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘキシレン基、Ｒ３はオクタノイル基、Ａ１ａＯはＥＯ（エチレンオキシ基）６モル、ＰＯ（プロピレンオキシ基）２モル、ｍａは８であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−４」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により９５％であることを確認した。
(A-4)
In the above-mentioned production method of "A-3", 184 g of 6-cyclohexylhexyl alcohol is used instead of 7-cyclohexylheptyl alcohol, and 264 g of ethylene oxide and 116 g of propylene oxide are used instead of 132 g of ethylene oxide, and olein is used. A-4 was obtained in the same manner except that 82 g of octanoic acid was used instead of 141 g of acid.
In this "A-4", the ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is a hexylene group, R 3 is an octanoyl group, and A 1 a O is EO (ethyleneoxy). group) 6 moles, PO (propylene oxy group) 2 moles, m a is cycloalkyl alkanol derivative compound is 8. Further, it was confirmed that the purity of "A-4" was 95% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−５）
６−シクロヘキシルへキシルアルコール１８４ｇをオートクレーブに仕込み、触媒として水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してエチレンオキサイド８８ｇ、プロピレンオキサイド１１６ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成したリン酸カリウムを濾別して、７−シクロヘキシルヘプチルアルコールのエチレンオキサイドとプロピレンオキサイドの付加重合物を得た。
得られた付加重合物のうち１９４ｇと、アジピン酸３７ｇを窒素ガス存在下において７５℃で溶融した後、触媒としてパラトルエンスルホン酸０．３ｇを加え、１２０℃で２ｍｍＨｇの減圧下で生成する水を反応系外に排出させながら４時間反応させた。次いで窒素ガス存在下において１０５℃で常圧に戻し、吸着剤を添加して触媒を処理し、９０℃で濾過することでＡ−５を得た。
この「Ａ−５」は、一般式（２）中の環Ｑｂはシクロへキシレン基、Ｒ１ｂは水素原子、Ｒ２ｂはヘキシレン基、Ｒ４はアジポイル基、Ａ１ｂＯはＥＯ（エチレンオキシ基）２モル、ＰＯ（プロピレンオキシ基）２モル、ｍｂは４であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−５」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により９６％であることを確認した。
(A-5)
184 g of 6-cyclohexylhexyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 88 g of ethylene oxide and 116 g of propylene oxide were press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptyl alcohol.
194 g of the obtained addition polymer and 37 g of adipic acid are melted at 75 ° C. in the presence of nitrogen gas, 0.3 g of p-toluenesulfonic acid is added as a catalyst, and water produced at 120 ° C. under a reduced pressure of 2 mmHg. Was reacted for 4 hours while being discharged from the reaction system. Then, the pressure was returned to normal pressure at 105 ° C. in the presence of nitrogen gas, an adsorbent was added to treat the catalyst, and filtration was performed at 90 ° C. to obtain A-5.
In this "A-5", the ring Q b in the general formula (2) is a cyclohexylene group, R 1 b is a hydrogen atom, R 2 b is a hexylene group, R 4 is an adipoil group, and A 1 b O is EO (ethyleneoxy). Group) 2 mol, PO (propyleneoxy group) 2 mol, mb is 4 is a cycloalkyl alkanol derivative compound. Further, it was confirmed that the purity of "A-5" was 96% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−６）
上記「Ａ−３」の製造方法において、７−シクロヘキシルヘプチルアルコールに代えて
、２−シクロヘキシルエチルアルコールを１２８ｇ使用し、オレイン酸１４１ｇに代えてステアリン酸１４２ｇを使用した以外は同じようにして、Ａ−６を得た。
この「Ａ−６」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはエチレン基、Ｒ３はステアロイル基、Ａ１ａＯはＥＯ（エチレンオキシ基）、ｍａは３であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−６」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により９７％であることを確認した。
(A-6)
In the above-mentioned production method of "A-3", 128 g of 2-cyclohexylethyl alcohol was used instead of 7-cyclohexylheptyl alcohol, and 142 g of stearic acid was used instead of 141 g of oleic acid. I got -6.
The "A-6", the ring Q a in the general formula (1) cyclohexylene group, R 1a is a hydrogen atom, R 2a is an ethylene group, R 3 is a stearoyl group, A 1a O is EO (ethyleneoxy group), m a is cycloalkyl alkanol derivative compound is 3. Further, it was confirmed that the purity of "A-6" was 97% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−７）
２−シクロヘキシルエチルアルコール１２８ｇをオートクレーブに仕込み、触媒として水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してエチレンオキサイド３５２ｇ、プロピレンオキサイド１１６ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成したリン酸カリウムを濾別して、２−シクロヘキシルエチルアルコールのエチレンオキサイドとプロピレンオキサイドの付加重合物Ａ−７を得た。
この「Ａ−７」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはエチレン基、Ｒ３は水素原子、Ａ１ａＯはＥＯ（エチレンオキシ基）８モル、ＰＯ（プロピレンオキシ基）２モル、ｍａは１０であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−７」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-7)
128 g of 2-cyclohexylethyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 352 g of ethylene oxide and 116 g of propylene oxide were press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain an addition polymer A-7 of 2-cyclohexylethyl alcohol, ethylene oxide and propylene oxide.
The "A-7", the ring Q a in the general formula (1) cyclohexylene group, R 1a is a hydrogen atom, R 2a is an ethylene group, R 3 is a hydrogen atom, A 1a O is EO (ethyleneoxy group) 8 moles, PO (propylene oxy group) 2 moles, m a cycloalkyl alkanol derivative compounds 10. Further, it was confirmed that the purity of "A-7" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−８）
上記「Ａ−７」の製造方法において、２−シクロヘキシルエチルアルコールに代えて、７−シクロヘキシルヘプチルアルコールを１９８ｇ使用し、エチレンオキサイド３５２ｇ、プロピレンオキサイド１１６ｇに代えて、エチレンオキサイド２６４ｇ、プロピレンオキサイド１１６ｇを使用した以外は同じようにして、Ａ−８を得た。
この「Ａ−８」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘプチレン基、Ｒ３は水素原子、Ａ１ａＯはＥＯ（エチレンオキシ基）６モル、ＰＯ（プロピレンオキシ基）２モル、ｍａは８であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−８」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-8)
In the above-mentioned production method of "A-7", 198 g of 7-cyclohexylheptyl alcohol is used instead of 2-cyclohexylethyl alcohol, and 264 g of ethylene oxide and 116 g of propylene oxide are used instead of 352 g of ethylene oxide and 116 g of propylene oxide. A-8 was obtained in the same manner except for the above.
The "A-8", the ring Q a in the general formula (1) cyclohexylene group, R 1a is a hydrogen atom, R 2a is a heptylene group, R 3 is a hydrogen atom, A 1a O is EO (ethyleneoxy group) 6 moles, PO (propylene oxy group) 2 moles, m a is cycloalkyl alkanol derivative compound is 8. Further, it was confirmed that the purity of "A-8" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−９）
上記「Ａ−７」の製造方法において、２−シクロヘキシルエチルアルコールに代えて、６−シクロヘキシルヘキシルアルコールを１８４ｇ使用し、プロピレンオキサイド１１６ｇに代えて、プロピレンオキサイド６３８ｇを使用した以外は同じようにして、Ａ−９を得た。
この「Ａ−９」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原子、Ｒ２ａはヘキシレン基、Ｒ３は水素原子、Ａ１ａＯはＥＯ（エチレンオキシ基）８モル、ＰＯ（プロピレンオキシ基）１１モル、ｍａは１９であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−９」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-9)
In the above-mentioned production method of "A-7", 184 g of 6-cyclohexylhexyl alcohol was used instead of 2-cyclohexylethyl alcohol, and 638 g of propylene oxide was used instead of 116 g of propylene oxide. A-9 was obtained.
In this "A-9", the ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is a hexylene group, R 3 is a hydrogen atom, and A 1 a O is EO (ethyleneoxy). group) 8 moles, PO (propylene oxy group) 11 mol m a cycloalkyl alkanol derivative compound is 19. Further, it was confirmed that the purity of "A-9" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−１０）
上記「Ａ−７」の製造方法において、２−シクロヘキシルエチルアルコールに代えて、６−シクロヘキシルヘキシルアルコールを１８４ｇ使用し、エチレンオキサイド３５２ｇ、プロピレンオキサイド１１６ｇに代えて、プロピレンオキサイド３４８ｇを使用した以外は同じようにして、Ａ−１０を得た。
この「Ａ−１０」は、一般式（１）中の環Ｑａはシクロへキシレン基、Ｒ１ａは水素原
子、Ｒ２ａはヘキシレン基、Ｒ３は水素原子、Ａ１ａＯはＰＯ（プロピレンオキシ基）６モル、ｍａは６であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−１０」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-10)
Same as above, except that 184 g of 6-cyclohexylhexyl alcohol was used instead of 2-cyclohexylethyl alcohol and 348 g of propylene oxide was used instead of 352 g of ethylene oxide and 116 g of propylene oxide in the above-mentioned production method of "A-7". Thus, A-10 was obtained.
In this "A-10", the ring Q a in the general formula (1) is a cyclohexylene group, R 1a is a hydrogen atom, R 2a is a hexylene group, R 3 is a hydrogen atom, and A 1 a O is PO (propyleneoxy). group) 6 mol, m a cycloalkyl alkanol derivative compound 6. Further, it was confirmed that the purity of "A-10" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−１１）
上記「Ａ−７」の製造方法において、２−シクロヘキシルエチルアルコールに代えて、８−（２−オクチルシクロプロピル）オクチルアルコールを２８２ｇ使用し、エチレンオキサイド３５２ｇ、プロピレンオキサイド１１６ｇに代えて、エチレンオキサイド１３２ｇ、プロピレンオキサイド１７４ｇを使用した以外は同じようにして、Ａ−１１を得た。
この「Ａ−１１」は、一般式（１）中の環Ｑａは１，２−シクロプロピレン基、Ｒ１ａはオクチル基、Ｒ２ａはオクチレン基、Ｒ３は水素原子、Ａ１ａＯはＥＯ（エチレンオキシ基）３モル、ＰＯ（プロピレンオキシ基）３モル、ｍａは６であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−１１」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-11)
In the production method of "A-7", 282 g of 8- (2-octylcyclopropyl) octyl alcohol was used instead of 2-cyclohexylethyl alcohol, and 132 g of ethylene oxide was used instead of 352 g of ethylene oxide and 116 g of propylene oxide. , A-11 was obtained in the same manner except that 174 g of propylene oxide was used.
The "A-11" has the general formula (1) ring Q a in 1,2-cyclopropylene group, R 1a is an octyl group, R 2a is an octylene group, R 3 is a hydrogen atom, A 1a O is EO (ethyleneoxy group) 3 moles, PO (propylene oxy group) 3 moles, m a cycloalkyl alkanol derivative compound 6. Further, it was confirmed that the purity of "A-11" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
（Ａ−１２）
上記「Ａ−７」の製造方法において、２−シクロヘキシルエチルアルコールに代えて、シクロプロピルメチルアルコールを７２ｇ使用し、エチレンオキサイド３５２ｇ、プロピレンオキサイド１１６ｇに代えて、エチレンオキサイド４４０ｇを使用した以外は同じようにして、Ａ−１２を得た。 この「Ａ−１２」は、一般式（１）中の環Ｑａはシクロプロピレン基、Ｒ１ａは水素原子、Ｒ２ａはメチレン基、Ｒ３は水素原子、Ａ１ａＯはＥＯ（エチレンオキシ基）１０モル、ｍａは１０であるシクロアルキルアルカノール誘導体化合物である。また「Ａ−１２」の純度は、本発明のシクロアルキルアルカノール誘導体として、ＧＣ−ＭＳの測定により１００％であることを確認した。
(A-12)
The same applies except that 72 g of cyclopropylmethyl alcohol was used instead of 2-cyclohexylethyl alcohol and 440 g of ethylene oxide was used instead of 352 g of ethylene oxide and 116 g of propylene oxide in the above-mentioned production method of "A-7". Then, A-12 was obtained. The "A-12" has the general formula (1) ring Q a is cyclopropylene group in, R 1a is a hydrogen atom, R 2a is a methylene group, R 3 is a hydrogen atom, A 1a O is EO (ethyleneoxy group ) 10 mol, m a is cycloalkyl alkanol derivative compounds 10. Further, it was confirmed that the purity of "A-12" was 100% by the measurement of GC-MS as the cycloalkyl alkanol derivative of the present invention.
＜有機リン酸エステルの合成＞
（Ｂ−１）
６−シクロヘキシルヘキシルアルコール１８４ｇをオートクレーブに仕込み、触媒として水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してエチレンオキサイド２２０ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成したリン酸カリウムを濾別して６−シクロヘキシルヘキシルアルコールのエチレンオキサイド付加重合物を得た。
得られた重合物のうち、２０２ｇをフラスコに仕込み、６５〜７０℃に保持して、撹拌しながら無水リン酸２４ｇを少量ずつ１時間かけて加えた後、６５〜７０℃で３時間熟成反応させた。室温に冷却後、水酸化カリウム２８ｇを徐々に加えて中和することで、有機リン酸エステルＢ−１を得た。
この「Ｂ−１」は、本願の一般式（３）で示される有機リン酸エステルＰ１、本願の一般式（４）で示される有機リン酸エステルＰ２、及び本願の一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率の合計を１００％としたときの、Ｐ１〜Ｐ３のＰ核ＮＭＲ積分比率は、それぞれ０％、４８％、５２％であった。
<Synthesis of organic phosphate ester>
(B-1)
184 g of 6-cyclohexylhexyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 220 g of ethylene oxide was press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain an ethylene oxide addition polymer of 6-cyclohexylhexyl alcohol.
Of the obtained polymer, 202 g was placed in a flask, kept at 65 to 70 ° C., 24 g of anhydrous phosphoric acid was added little by little over 1 hour with stirring, and then the aging reaction was carried out at 65 to 70 ° C. for 3 hours. I let you. After cooling to room temperature, 28 g of potassium hydroxide was gradually added to neutralize the mixture to obtain an organic phosphate ester B-1.
This "B-1" is represented by the organic phosphate ester P1 represented by the general formula (3) of the present application, the organic phosphate ester P2 represented by the general formula (4) of the present application, and the general formula (5) of the present application. When the total P-nuclear NMR integration ratio attributable to the organic phosphate ester P3 was 100%, the P-nuclear NMR integration ratios of P1 to P3 were 0%, 48%, and 52%, respectively.
（Ｂ−２）
２−シクロヘキシルエチルアルコール１２８ｇをオートクレーブに仕込み、触媒として水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してプロピレンオキサイド１７４ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成した
リン酸カリウムを濾別して２−シクロヘキシルエチルアルコールのプロピレンオキサイド付加重合物を得た。
得られた重合物のうち、１５１ｇをフラスコに仕込み、６５〜７０℃に保持して、撹拌しながら無水リン酸２２ｇを少量ずつ１時間かけて加えた後、６５〜７０℃で３時間熟成反応させた。室温に冷却後、ジブチルエタノールアミン８７ｇを徐々に加えて中和することで、有機リン酸エステルＢ−２を得た。
この「Ｂ−２」は、本願の一般式（３）で示される有機リン酸エステルＰ１、本願の一般式（４）で示される有機リン酸エステルＰ２、及び本願の一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率の合計を１００％としたときの、Ｐ１〜Ｐ３のＰ核ＮＭＲ積分比率は、それぞれ１２％、４３％、４５％であった。
(B-2)
128 g of 2-cyclohexylethyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 174 g of propylene oxide was press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain a propylene oxide addition polymer of 2-cyclohexylethyl alcohol.
Of the obtained polymer, 151 g was charged in a flask, kept at 65 to 70 ° C., 22 g of anhydrous phosphoric acid was added little by little over 1 hour with stirring, and then the aging reaction was carried out at 65 to 70 ° C. for 3 hours. I let you. After cooling to room temperature, 87 g of dibutylethanolamine was gradually added to neutralize the mixture to obtain an organic phosphate ester B-2.
This "B-2" is represented by the organic phosphate ester P1 represented by the general formula (3) of the present application, the organic phosphate ester P2 represented by the general formula (4) of the present application, and the general formula (5) of the present application. When the total P-nuclear NMR integration ratio attributable to the organic phosphate ester P3 was 100%, the P-nuclear NMR integration ratios of P1 to P3 were 12%, 43%, and 45%, respectively.
（Ｂ−３）
７−シクロヘキシルヘプチルアルコール１９８ｇをオートクレーブに仕込み、触媒として水酸化カリウム０．３ｇを加えた後、オートクレーブ内を窒素で十分に置換した。撹拌しながら、ゲージ圧力０．０〜０．４ＭＰａ、反応温度１１０〜１２０℃に維持してエチレンオキサイド２６４ｇ及びプロピレンオキサイド１１６ｇを圧入して、約５時間付加重合反応を行った。その後得られた反応物をフラスコに移し、触媒の水酸化カリウムをリン酸で中和した。中和により生成したリン酸カリウムを濾別して７−シクロヘキシルヘプチルアルコールのエチレンオキサイドとプロピレンオキサイドの付加重合物を得た。
得られた重合物のうち、２８９ｇをフラスコに仕込み、６５〜７０℃に保持して、撹拌しながら無水リン酸２３ｇを少量ずつ１時間かけて加えた後、６５〜７０℃で３時間熟成反応させた。室温に冷却後、水酸化カリウム２８ｇを徐々に加えて中和することで、有機リン酸エステルＢ−３を得た。
この「Ｂ−３」は、本願の一般式（３）で示される有機リン酸エステルＰ１、本願の一般式（４）で示される有機リン酸エステルＰ２、及び本願の一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率の合計を１００％としたときの、Ｐ１〜Ｐ３のＰ核ＮＭＲ積分比率は、それぞれ５％、４７％、４８％であった。
(B-3)
198 g of 7-cyclohexylheptyl alcohol was charged into the autoclave, 0.3 g of potassium hydroxide was added as a catalyst, and then the inside of the autoclave was sufficiently replaced with nitrogen. While stirring, the gauge pressure was maintained at 0.0 to 0.4 MPa and the reaction temperature was maintained at 110 to 120 ° C., and 264 g of ethylene oxide and 116 g of propylene oxide were press-fitted to carry out an addition polymerization reaction for about 5 hours. The resulting reaction was then transferred to a flask and the catalyst potassium hydroxide was neutralized with phosphoric acid. Potassium phosphate produced by neutralization was filtered off to obtain an addition polymer of ethylene oxide and propylene oxide of 7-cyclohexylheptyl alcohol.
Of the obtained polymer, 289 g was charged in a flask, kept at 65 to 70 ° C., and 23 g of anhydrous phosphoric acid was added little by little over 1 hour with stirring, and then the aging reaction was carried out at 65 to 70 ° C. for 3 hours. I let you. After cooling to room temperature, 28 g of potassium hydroxide was gradually added to neutralize the mixture to obtain an organic phosphate ester B-3.
This "B-3" is represented by the organic phosphate ester P1 represented by the general formula (3) of the present application, the organic phosphate ester P2 represented by the general formula (4) of the present application, and the general formula (5) of the present application. When the total P-nuclear NMR integration ratio attributable to the organic phosphate ester P3 was 100%, the P-nuclear NMR integration ratios of P1 to P3 were 5%, 47%, and 48%, respectively.
（Ｂ−４）
６−シクロヘキシルヘキシルアルコール１８４ｇをフラスコに仕込み、６５〜７０℃に保持して、撹拌しながら無水リン酸４５ｇを少量ずつ１時間かけて加えた後、６５〜７０℃で３時間熟成反応させた。室温に冷却後、水酸化ナトリウム４０ｇを徐々に加えて中和することで、有機リン酸エステルＢ−４を得た。
この「Ｂ−４」は、本願の一般式（３）で示される有機リン酸エステルＰ１、本願の一般式（４）で示される有機リン酸エステルＰ２、及び本願の一般式（５）で示される有機リン酸エステルＰ３に帰属されるＰ核ＮＭＲ積分比率の合計を１００％としたときの、Ｐ１〜Ｐ３のＰ核ＮＭＲ積分比率は、それぞれ１６％、４２％、４２％であった。
(B-4)
184 g of 6-cyclohexylhexyl alcohol was placed in a flask, kept at 65 to 70 ° C., 45 g of anhydrous phosphoric acid was added little by little over 1 hour with stirring, and then the aging reaction was carried out at 65 to 70 ° C. for 3 hours. After cooling to room temperature, 40 g of sodium hydroxide was gradually added to neutralize the mixture to obtain an organic phosphate ester B-4.
This "B-4" is represented by the organic phosphate ester P1 represented by the general formula (3) of the present application, the organic phosphate ester P2 represented by the general formula (4) of the present application, and the general formula (5) of the present application. When the total P-nuclear NMR integration ratio attributable to the organic phosphate ester P3 was 100%, the P-nuclear NMR integration ratios of P1 to P3 were 16%, 42%, and 42%, respectively.
本発明の合成繊維用処理剤（実施例１〜１６）の組成を表１に、その比較例（比較例１〜４）の組成を表２に示した。 The composition of the synthetic fiber treatment agent of the present invention (Examples 1 to 16) is shown in Table 1, and the composition of the comparative example (Comparative Examples 1 to 4) is shown in Table 2.
表１、２において、
Ｅ−１：２級アルキル（炭素数１２〜１５）スルホン酸ナトリウム
Ｅ−２：オレイン酸カリウム
Ｅ−３：オレイルアルコールＥＯ２リン酸エステルとラウリルアミンＥＯ２の塩
Ｅ−４：ラウリルリン酸エステルカリウム
Ｎ−１：硬化ひまし油ＥＯ１２トリオレアート
Ｎ−２：トリデカノールＥＯ３・ＰＯ２パルミタート
Ｎ−３：オレイン酸ＥＯ５
Ｎ−４：ノナノールＥＯ６・ＰＯ２
Ｎ−５：ラウリルアルコールＥＯ６・ＰＯ２
Ｎ−６：イソトリデカノールＥＯ１０・ＰＯ１５
Ｎ−７：ラウリルアルコールＥＯ５５・ＰＯ４０
Ｎ−８：テトラデカノールＥＯ１５・ＰＯ１５
Ｎ−９：ブタノールＥＯ６・ＰＯ１０
Ｎ−１０：グリセリンＥＯ１２
Ｌ−１：鉱物油（４７ｍｍ２／ｓ）
Ｌ−２：オクチルパルミタート
Ｌ−３：ラウリルオレアート
Ｌ−４：イソトリデシルステアラート
Ｌ−５：トリメチロールプロパントリラウラート
Ｌ−６：ソルビタンモノオレアート
Ｌ−７：なたね油
In Tables 1 and 2,
E-1: Secondary alkyl (12 to 15 carbon atoms) Sodium sulfonate E-2: Potassium oleate E-3: Salt of oleyl alcohol EO2 phosphate and laurylamine EO2 E-4: Potassium lauryl phosphate N -1: Hardened castor oil EO12 Trioleate N-2: Tridecanol EO3 / PO2 Palmitate N-3: Oleic acid EO5
N-4: Nonanol EO6 / PO2
N-5: Lauryl alcohol EO6 / PO2
N-6: Isotridecanol EO10 / PO15
N-7: Lauryl alcohol EO55 / PO40
N-8: Tetradecanol EO15 / PO15
N-9: Butanol EO6 / PO10
N-10: Glycerin EO12
L-1: Mineral oil (47 mm 2 / s)
L-2: Octylpalmitate L-3: Lauryl oleart L-4: Isotridecyl steerert L-5: Trimethylolpropane trilaurate L-6: Sorbitan monooleart L-7: Canola oil
・エマルション安定性評価
合成繊維用処理剤とイオン交換水を均一混合して、濃度１５％の合成繊維用処理剤エマルションを調製してふた付きポリビンに入れ密閉し、合成繊維用処理剤エマルションを４０℃で７日間静置した後、外観を目視で観察すると共に、透過率の変化を下記基準により評価した。透過率は分光光度計（島津製作所製の紫外可視分光光度計Ｕ−１８００）を用いて測定し、以下の基準で評価した。結果を表３にまとめて示した。
［エマルション安定性評価基準］
◎◎：エマルション調製直後からの透過率の低下が５％未満
◎：エマルション調製直後からの透過率の低下が５％以上、１０％未満
○：エマルション調製直後からの透過率の低下が１０％以上、２０％未満
×：エマルション調製直後からの透過率の低下が２０％以上、又は粒子発生や分離が確認される
-Emulsion stability evaluation A synthetic fiber treatment agent and ion-exchanged water are uniformly mixed to prepare a synthetic fiber treatment agent emulsion having a concentration of 15%, placed in a polybin with a lid and sealed to form a synthetic fiber treatment agent emulsion of 40. After allowing to stand at ° C. for 7 days, the appearance was visually observed and the change in permeability was evaluated according to the following criteria. The transmittance was measured using a spectrophotometer (ultraviolet-visible spectrophotometer U-1800 manufactured by Shimadzu Corporation) and evaluated according to the following criteria. The results are summarized in Table 3.
[Emulsion stability evaluation criteria]
◎ ◎: Decrease in transmittance immediately after emulsion preparation is less than 5% ◎: Decrease in transmittance immediately after emulsion preparation is 5% or more and less than 10% ○: Decrease in transmittance immediately after emulsion preparation is 10% or more , Less than 20% ×: Decrease in transmittance of 20% or more immediately after emulsion preparation, or particle generation or separation is confirmed.
・低温ハンドリング性評価
３０℃まで加温し、撹拌均一化させた合成繊維用処理剤を容量１００ｍＬのふた付きポリビン（内径４５ｍｍ）に６０ｍＬ入れ、容器を密閉した。設定温度を−５℃にしたインキュベーターに合成繊維用処理剤を入れたポリビンを３日間静置した。静置後、水性液の外観を目視判定し、以下の基準により評価した。下記基準に示される「流動性」とは合成繊維用処理剤を入れたポリビンを横（９０°）に傾け、３０秒以内に水性液の一部が容器外へ流れ出た場合、流動性ありと判断した。結果を表３にまとめて示した。
［低温ハンドリング性評価基準］
◎◎：外観に曇り、濁りはなく、流動性がある
◎：流動性はあるが外観に曇り、濁りがあり、一部凝固している
○：流動性はあるが外観に曇り、濁りがあり、大半が凝固している
×：完全に凝固しており、流動性がない
-Evaluation of low temperature handling property 60 mL of a synthetic fiber treatment agent heated to 30 ° C. and stirred and homogenized was placed in a polybin with a lid (inner diameter 45 mm) having a capacity of 100 mL, and the container was sealed. A polybin containing a synthetic fiber treatment agent was allowed to stand in an incubator at a set temperature of −5 ° C. for 3 days. After standing, the appearance of the aqueous solution was visually judged and evaluated according to the following criteria. The "fluidity" shown in the following criteria means that the polybin containing the synthetic fiber treatment agent is tilted sideways (90 °), and if a part of the aqueous liquid flows out of the container within 30 seconds, it is considered to be fluid. It was judged. The results are summarized in Table 3.
[Low temperature handling evaluation criteria]
◎ ◎: The appearance is cloudy, not turbid, and has fluidity. ◎: There is fluidity, but the appearance is cloudy, turbid, and partly solidified. , Mostly solidified ×: Completely solidified and non-fluid
・延伸糸の製造
固有粘度０．６４、酸化チタン含有量０．２％のポリエチレンテレフタラートを常法により乾燥した後、エクストルーダーを用いて２９５℃で紡糸し、口金から吐出して冷却固化した後の走行糸条に、濃度１０％に調製した合成繊維用処理剤の水性液を、計量ポンプを用いたガイド給油法により、合成繊維用処理剤としての付着量が１．０％となるように付着させた後、ガイドで集束させ、表面速度１４００ｍ／分で表面温度９０℃の第１ゴデットローラーと、表面速度４８００ｍ／分で表面温度１５０℃の第２ゴデットローラーとで延伸後、４８００ｍ／分の速度で巻き取り、８３デシテックス３６フィラメントの延伸糸を得た。
-Manufacture of drawn yarn After drying polyethylene terephthalate with an intrinsic viscosity of 0.64 and a titanium oxide content of 0.2% by a conventional method, it was spun at 295 ° C. using an extruder and discharged from a mouthpiece to be cooled and solidified. An aqueous solution of the synthetic fiber treatment agent prepared to have a concentration of 10% is applied to the subsequent running yarn by a guide lubrication method using a measuring pump so that the adhesion amount as the synthetic fiber treatment agent is 1.0%. After being adhered to the yarn, the fibers were focused with a guide and stretched with a first Godet roller having a surface speed of 1400 m / min and a surface temperature of 90 ° C. and a second Godet roller having a surface speed of 4800 m / min and a surface temperature of 150 ° C. The yarn was wound at a speed of 4800 m / min to obtain a drawn yarn of 83 decitex 36 filaments.
・発生電気の評価
前記の延伸糸の製造で得た延伸糸を巻き返し、糸量２００ｇのチーズを得た。このチーズを２０℃、相対湿度４０％の雰囲気下に３日間調湿し、下記の条件で発生電気の測定と評価を行った。
（条件）
２０℃、相対湿度４０％の雰囲気下、チーズ２０本をクリールスタンドに設置して糸を解舒し、ワッシャーテンサーを通した後、入角度及び出角度ともに１０度になるように調整した直径２ｃｍで長さ５ｃｍの３本のアルミナピンに接触走行させ、２００ｍ／分の速度で巻き取った。この時、走行する２０本のフィラメントから成るシートの静電気（発生電気）を、３番目のアルミナピンを出て２０ｃｍの位置にて、集電式電位測定器により測定した。
測定値を下記の基準により評価した。結果を表３にまとめて示した。
［発生電気の評価基準］
◎：発生電気が０．５ｋＶ未満であって、制電性が優れている
○：発生電気が０．５ｋＶ以上２ｋＶ未満であって、制電性は良である
×：発生電気が２ｋＶ以上であって、制電性は不良である
-Evaluation of generated electricity The drawn yarn obtained in the production of the drawn yarn was rewound to obtain cheese having a yarn amount of 200 g. This cheese was conditioned for 3 days in an atmosphere of 20 ° C. and a relative humidity of 40%, and the generated electricity was measured and evaluated under the following conditions.
(conditions)
In an atmosphere of 20 ° C and 40% relative humidity, 20 cheeses were placed on a creel stand, the threads were unwound, and after passing through a washer tensor, the diameter was adjusted to 10 degrees for both the entry angle and the exit angle. It was run in contact with three alumina pins having a length of 5 cm and wound at a speed of 200 m / min. At this time, the static electricity (generated electricity) of the sheet composed of 20 traveling filaments was measured by a current collector type potential measuring device at a position 20 cm out of the third alumina pin.
The measured values were evaluated according to the following criteria. The results are summarized in Table 3.
[Evaluation criteria for generated electricity]
⊚: Generated electricity is less than 0.5 kV and excellent antistatic property ○: Generated electricity is 0.5 kV or more and less than 2 kV and antistatic property is good ×: Generated electricity is 2 kV or more There is a poor antistatic property
表３の結果からも明らかなように、本発明の具体例である実施例１〜１６の合成繊維用処理剤は、エマルション安定性や低温ハンドリング性に優れ、延伸糸の制電性にも優れることが明らかとなった。 As is clear from the results in Table 3, the synthetic fiber treatment agents of Examples 1 to 16 which are specific examples of the present invention are excellent in emulsion stability and low temperature handling property, and are also excellent in antistatic property of drawn yarn. It became clear.
本発明の合成繊維用処理剤、この合成繊維用処理剤が付着した合成繊維及び合成繊維の処理方法は、合成繊維の紡糸工程や仮撚工程、後加工工程における近年の高速化にも対応して、優れた制電性より静電気や毛羽を防止できるという効果を発揮するものである。
また、本発明の合成繊維用処理剤は、エマルション安定性や氷点下の環境下における低温ハンドリング性に優れるため、低温環境下での貯蔵でも含有成分が分離することなく、合成繊維用処理剤が均一に付着させ得るため有用である。
The treatment agent for synthetic fibers of the present invention, and the treatment method for synthetic fibers and synthetic fibers to which the treatment agent for synthetic fibers is attached can cope with the recent high speed in the spinning process, false twisting process, and post-processing process of synthetic fibers. Therefore, it exerts the effect of preventing static electricity and fluff rather than having excellent antistatic properties.
Further, since the synthetic fiber treatment agent of the present invention is excellent in emulsion stability and low temperature handling in a sub-zero environment, the synthetic fiber treatment agent is uniform without separating the contained components even when stored in a low temperature environment. It is useful because it can be attached to.
Claims (10)
環Ｑａ：炭素数３〜８のシクロアルキレン基
Ｒ１ａ：水素原子又は炭素数１〜１２のアルキル基
Ｒ２ａ：炭素数１〜１２の２価の炭化水素基
Ｒ３：水素原子又は炭素数６〜２２のモノカルボン酸から水酸基を除いた残基
Ａ１ａＯ：炭素数２〜４のアルキレンオキシ基（ただし、当該アルキレンオキシ基が２以上存在する場合は、１種単独又は２種以上でも良い。）
ｍａ：０〜１００の整数、
ただし、ｍ ａ が０でありＲ ３ が水素原子である場合を除く。）
Ｒ４：炭素数４〜１２のジカルボン酸から２つの水酸基を除いた残基、
ただし、ｍ ｂ が０である場合を除く。） A treatment agent for synthetic fibers, which comprises one or more selected from the cycloalkyl alkanol derivatives represented by the following general formulas (1) and (2).
Ring Q a: cycloalkylene group R 1a having 3 to 8 carbon atoms: alkyl groups R 2a hydrogen atom or 1 to 12 carbon atoms: a divalent hydrocarbon group having 1 to 12 carbon atoms R 3: a hydrogen atom or a carbon atoms Residues obtained by removing hydroxyl groups from 6 to 22 monocarboxylic acids A 1a O: alkyleneoxy groups having 2 to 4 carbon atoms (however, if two or more of the alkyleneoxy groups are present, one type alone or two or more types may be used. good.)
m a: 0~100 of integer,
However, this does not apply when ma is 0 and R 3 is a hydrogen atom. )
R 4 : A residue obtained by removing two hydroxyl groups from a dicarboxylic acid having 4 to 12 carbon atoms .
However, this does not apply when mb is 0. )
を除く）及びイオン性界面活性剤を含有する請求項１〜５のいずれか一項に記載の合成繊維用処理剤。 The treatment agent for synthetic fibers according to any one of claims 1 to 5, further comprising a smoothing agent, a nonionic surfactant (excluding the cycloalkyl alkanol derivative) and an ionic surfactant.
ｎ：２〜４の整数
Ｒ５：「Ｒ１ｃ−環Ｑｃ−Ｒ２ｃ−Ｏ−（Ａ１ｃＯ）ｍｃ−」から末端の酸素原子を除いた残基（ただし、環Ｑｃ、Ｒ１ｃ、Ｒ２ｃ、Ａ１ｃＯ、ｍｃは、一般式（１）の環Ｑａ、Ｒ１ａ、Ｒ２ａ、Ａ１ａＯ、ｍａと各々独立して同じ意味である。）、アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子
Ｍ１：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ２：アルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子）
Ｍ３、Ｍ４：各々独立してアルカリ金属、アルカリ土類金属（１／２）、有機アミン塩、又は水素原子） The ionic surfactant is represented by the organic phosphate ester P1 represented by the following general formula (3), the organic phosphate ester P2 represented by the following general formula (4), and the following general formula (5). The treatment agent for synthetic fibers according to claim 6 or 7, which contains at least one organic phosphoric acid ester selected from the organic phosphoric acid ester P3.
n: Integer of 2 to 4 R 5 : Residue excluding the terminal oxygen atom from "R 1c -ring Q c- R 2c -O- (A 1c O) m c- " (however, ring Q c , R 1c, R 2c, a 1c O , m c is a ring Q a in the general formula (1), R 1a, R 2a, a 1a O, m a and each independently the same meaning.), alkali metal, Alkaline earth metal (1/2), organic amine salt, or hydrogen atom M 1 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 2 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom)
M 3 , M 4 : Alkaline metal, alkaline earth metal (1/2), organic amine salt, or hydrogen atom, respectively)
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| JPH10265789A (en) * | 1997-03-26 | 1998-10-06 | New Japan Chem Co Ltd | Lubricant base oil |
| JP2002069435A (en) * | 2000-08-31 | 2002-03-08 | Sanyo Chem Ind Ltd | Oil for dust adsorption |
| JP2012251267A (en) * | 2011-06-06 | 2012-12-20 | Mitsubishi Rayon Co Ltd | Carbon fiber precursor acrylic fiber bundle |
| JP2013060680A (en) * | 2011-09-13 | 2013-04-04 | Mitsubishi Rayon Co Ltd | Method for producing carbon fiber |
| JP2017110319A (en) * | 2015-12-18 | 2017-06-22 | 松本油脂製薬株式会社 | Treatment agent for elastic fiber and use of the same |
| JP2021031788A (en) * | 2019-08-21 | 2021-03-01 | 松本油脂製薬株式会社 | Treating agent for elastic fibers and elastic fibers |
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| JPH10245729A (en) | 1997-02-25 | 1998-09-14 | Teijin Ltd | Draw-false twist texturing of synthetic fiber |
| WO2012169551A1 (en) * | 2011-06-06 | 2012-12-13 | 三菱レイヨン株式会社 | Oil solution for carbon fiber precursor acrylic fibers, oil solution composition for carbon fiber precursor acrylic fibers, oil solution processed liquid for carbon fiber precursor acrylic fibers, carbon fiber precursor acrylic fiber bundle, and method for producing carbon fiber bundle using carbon fiber precursor acrylic fiber bundle |
| WO2017150229A1 (en) * | 2016-03-04 | 2017-09-08 | 松本油脂製薬株式会社 | Synthetic fiber treatment agent and use thereof |
| JP6738698B2 (en) * | 2016-09-09 | 2020-08-12 | ライオン株式会社 | Textile product treating agent composition |
| JP6600835B1 (en) * | 2019-07-24 | 2019-11-06 | 竹本油脂株式会社 | Synthetic fiber treatment agent and synthetic fiber |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10265789A (en) * | 1997-03-26 | 1998-10-06 | New Japan Chem Co Ltd | Lubricant base oil |
| JP2002069435A (en) * | 2000-08-31 | 2002-03-08 | Sanyo Chem Ind Ltd | Oil for dust adsorption |
| JP2012251267A (en) * | 2011-06-06 | 2012-12-20 | Mitsubishi Rayon Co Ltd | Carbon fiber precursor acrylic fiber bundle |
| JP2013060680A (en) * | 2011-09-13 | 2013-04-04 | Mitsubishi Rayon Co Ltd | Method for producing carbon fiber |
| JP2017110319A (en) * | 2015-12-18 | 2017-06-22 | 松本油脂製薬株式会社 | Treatment agent for elastic fiber and use of the same |
| JP2021031788A (en) * | 2019-08-21 | 2021-03-01 | 松本油脂製薬株式会社 | Treating agent for elastic fibers and elastic fibers |
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| KR20230153490A (en) | 2023-11-06 |
| JP2022163740A (en) | 2022-10-27 |
| TWI830199B (en) | 2024-01-21 |
| DE112022002152T5 (en) | 2024-02-22 |
| WO2022219889A1 (en) | 2022-10-20 |
| TW202302957A (en) | 2023-01-16 |
| CN117441047A (en) | 2024-01-23 |
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