Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
  • D06M23/02—Processes in which the treating agent is releasably affixed or incorporated into a dispensing means
• • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
  • C10M105/32—Esters
  • C10M105/34—Esters of monocarboxylic acids
• • 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
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • 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

Definitions

• the present invention relates to a fiber treatment agent.
• it is related with the processing agent for fibers used for the manufacturing process and processing process of a fiber accompanying a heat process.
• fiber processing agents that impart lubricity, bundling properties, antistatic properties, etc. to the fibers are used in accordance with the purpose in order to facilitate fiber spinning and drawing.
• a lubricating component for fibers paraffinic hydrocarbons such as mineral oil, oleyl oleate, dioleyl adipate, dioleyl dipropionate and the like are conventionally known.
• Japanese Patent Publication No. 47-29474 discloses an ester of a bisphenol alkylene oxide adduct as a lubricating component having good heat resistance with little decomposition and no smoke generation. Further, as a fiber treating agent having good heat resistance, JP-A-6-228866 discloses a technique using an ester compound of 1,2,3,4-butenetetracarboxylic acid, and JP-A-10-245781 discloses a phenol skeleton. A technique of using both an ester having a thiodipropionic acid ester in combination is disclosed.
• Japanese Laid-Open Patent Publication No. 6-010264 discloses a sizing method in which carbon fibers are treated with an aqueous solution of an ester compound and a nonionic surfactant.
• Japanese Patent Application Laid-Open No. 10-251974 discloses a synthetic fiber treating agent containing two kinds of compounds. Summary of invention
• This invention provides the processing agent for fibers containing the ester compound represented by following General formula (1).
• R 1 represents a hydrocarbon group having 8 to 24 carbon atoms
• R 2 represents an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms
• EO represents an ethyleneoxy group
• PO represents a propyleneoxy group.
• l and n are the average number of moles of ethyleneoxy group added, l is a number from 0 to 15, and n is a number from 1 to 20.
• the present invention provides a fiber treatment agent use or a fiber treatment method of the ester compound used in a fiber production process, a processing process or a spinning process involving a heat process.
• the emulsion treatment stability of the fiber treatment agent is required to uniformly attach the lubricating component to the fiber.
• the emulsifier component surfactant, etc.
• the hydro-viscosity causes thread breakage, or due to the low heat resistance of the emulsifier component itself. Therefore, there is a need for a treatment agent that can form an emulsion having good emulsification stability with a small amount of an emulsifier component.
• the melting point of the lubricating component used in the fiber treatment agent is high, the lubrication performance deteriorates, and the stability and handleability of the treatment agent deteriorate, so the lubrication is low and the liquid is liquid at room temperature (20 ° C.).
• the lubrication is low and the liquid is liquid at room temperature (20 ° C.).
• the present invention provides a fiber treating agent having a low melting point of the lubricating component and excellent handleability, as well as excellent lubricity, heat resistance and emulsion stability in water.
• the present inventors added an alkylene oxide in a specific form to an alcohol having a specific chain length, and further using an ester compound obtained by converting it to an ester with a fatty acid as a lubricating component.
• the present inventors have found that the above problems can be solved and have completed the present invention.
• a fiber treating agent that has a low melting point of a lubricating component and is liquid at room temperature, exhibits good handleability, and is excellent in all of lubricity, heat resistance, and emulsion stability in an aqueous system. Can do.
• Such a fiber treating agent is excellent in handleability at low temperatures, can be uniformly attached to the fiber yarn, and can be easily washed and removed in the scouring washing performed before the dyeing process, etc.
• the fiber treating agent of the present invention contains an ester compound represented by the above general formula (1).
• R 1 is a hydrocarbon group having 8 to 24 carbon atoms, preferably a hydrocarbon group having 10 to 22 carbon atoms, more preferably 12 to 18 carbon atoms.
• the hydrocarbon group for R 1 include a linear or branched alkyl group, an alkenyl group, or an aromatic hydrocarbon group that may be substituted with a linear or branched alkyl group or alkenyl group. From the viewpoint of lubricity under conditions, a primary linear alkyl group or alkenyl group is preferable, and a primary linear alkyl group is more preferable.
• R 1 is preferably hydroxy from natural higher alcohols such as octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol, oleyl alcohol and the like. It is preferable that the residue is a group from which one group is removed.
• lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, behenyl alcohol and oleyl More preferred is a residue obtained by removing one hydroxy group from an alcohol selected from alcohols, such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol and oleyl alcohol. More preferably one a residue obtained by removing hydroxy group from an alcohol selected from Lumpur, lauryl alcohol, myristyl alcohol, cetyl alcohol and residues formed by removing one hydroxyl group from an alcohol selected from stearyl alcohol is more preferred.
• R 2 is an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms, preferably a linear alkyl group or alkenyl group having 7 to 23 carbon atoms, more preferably carbon.
• Preferable specific examples of R 2 include a residue obtained by removing one carboxy group from a linear or branched, saturated or unsaturated fatty acid.
• octanoic acid decanoic acid
• Lauric acid myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, petrothelic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, erucic acid, isopalmitic acid (2-hexyldecanoic acid), 2 -Residues obtained by removing one carboxy group from a fatty acid selected from heptylundecanoic acid, citronellic acid and isostearic acid are preferred.
• l is a number from 0 to 15, preferably 0 to 5, more preferably 0 to 3, and still more preferably 0 from the viewpoint of lubricity.
• n is a number of 1 to 20, preferably 2 to 15, more preferably 3 to 12, and still more preferably 4 to 10 from the viewpoint of emulsion stability.
• m is a number of 0.5 to 20, preferably 0.8 to 15, more preferably 1 to 10, and still more preferably 1.2 to 8 from the viewpoint of lubricity. is there.
• - additional type of ((EO) l (PO) m) in the (EO) l and (PO) m may be random binding in block binding. From the viewpoint of keeping the melting point low, it is more preferable to use a block bond addition type.
• the ester compound represented by the general formula (1) exhibits a low melting point and improves handling.
• the fiber treating agent containing the ester compound can exhibit good performance in all of lubricity, heat resistance, and emulsion stability in water.
• the ester compound represented by the general formula (1) can be obtained, for example, by the following production method. That is, the ester compound represented by the general formula (1) is preferably produced by the following steps (I) to (III). Step (I): Step of adding an EO / PO mixture to one or more alcohols represented by the general formula R 1 —OH (2) (wherein R 1 represents the above meaning) (II): Step of adding EO to the obtained alkoxylate and step (III): Step of esterifying the obtained alkoxylate.
• R 1 has the above-mentioned meaning.
• a catalyst such as a known acid or base is added to one or two or more alcohols represented by the formula, and dehydration under reduced pressure at 20 to 140 ° C. as necessary. Then, 1) propylene oxide is added alone, 2) propylene oxide is added after addition of ethylene oxide, or 3) random addition of ethylene oxide and propylene oxide, followed by further addition of ethylene oxide As a result, a corresponding alkylene oxide adduct is obtained.
• an addition condition of the alkylene oxide it is preferable to perform an operation (aging operation) for continuing the reaction at a temperature of 80 to 180 ° C.
• an alkylene oxide adduct and the following general formula (3) R 2 -COOM (3) (Wherein R 2 represents the same meaning as described above, and M represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.) 1 type or 2 types or more of fatty acids or fatty acid esters represented by the above, if necessary, using a known metal, acid, base, etc. catalyst according to a conventional method, esterification reaction or transesterification reaction, if necessary
• an ester compound represented by the general formula (1) can be obtained by performing a purification operation such as catalyst removal or steaming with an adsorbent or the like.
• the form of the fiber treating agent of the present invention may be a liquid oil containing the ester compound represented by the general formula (1) [hereinafter referred to as the ester compound (1)] or the ester compound (1).
• the ester compound (1) may be an aqueous emulsion obtained by emulsifying water in an aqueous medium selected from water and a mixture of water and a water-soluble organic solvent (for example, ethanol, isopropanol, etc.). Since the ester compound (1) tends to exhibit self-emulsifying properties in an aqueous medium, the amount of the emulsifier component used together can be reduced, and it can be uniformly attached to the fiber without separating other function-imparting agents. Further, from the viewpoint of easy control of the amount of treatment agent attached to the fiber, it is preferable to treat the fiber in the form of an aqueous emulsion.
• the content of the ester compound (1) in the fiber treating agent of the present invention is preferably 3 to 70% by mass, more preferably 4 to 50% by mass, and still more from the viewpoint of imparting sufficient lubricity to the fiber.
• the content is preferably 5 to 25% by mass.
• the fiber treating agent of the present invention can suitably contain one or more selected from emulsifier components and other function-imparting agents.
• emulsifier component known emulsifier components such as nonionic surfactants, anionic surfactants and nitrogen-containing compounds can be suitably used.
• the nonionic surfactant is not particularly limited and known ones can be used.
• the anionic surfactant is not particularly limited and known ones can be used.
• fatty acid salts such as stearic acid, oleic acid and erucic acid, alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.
• ester salts and alkyl phosphate ester salts examples include ester salts and alkyl phosphate ester salts.
• nitrogen-containing compounds include cationic surfactants such as alkyl quaternary ammonium salts, alkyl hydroxyethyl ammonium salts, and imidazolinium salts, and amphoteric interfaces such as aliphatic alkanolamides, aliphatic amine ethylene oxide adducts, and alkyl betaines.
• An activator is mentioned.
• the fiber treatment agent of the present invention containing the ester compound (1) obtains a stable emulsion using less emulsifier components than the usual use amount. be able to. That is, the content of the emulsifier component in the fiber treating agent of the present invention can be adjusted in the range of 0 to 50% by mass, preferably 0.1 to 20% by mass.
• the content of the emulsifier component Can be obtained even when it is lowered to the range of 0.1 to 5% by mass, and further, an emulsion exhibiting good emulsification stability can be obtained, and further, the range of 0.1 to 3% by mass, 0.1 to 2% by mass Even when it is lowered to this range, it is possible to obtain an emulsion exhibiting good emulsification stability.
• smooth oils such as ester oils such as isostearyl isostearate, isostearyl adipate, trimethylolpropane trilaurate, and mineral oils such as liquid paraffin.
• Agent unmodified or ether-modified, amino-modified, epoxy-modified or glycol-modified silicone resin, polyacrylic ester, polyvinyl alcohol, paste ester such as terminal esterified product or etherified product of ethylene oxide adduct of bisphenol A, carbon number
• components usually used for fiber treatment agents such as extreme pressure additives such as 8 to 22 alkylamines and ethylene oxide adducts thereof, rust preventives, preservatives, and antioxidants.
• the content of these function-imparting agents can be appropriately determined according to the purpose within a range not impairing the effects of the present invention.
• the method for adhering (oiling) the fiber treating agent of the present invention to the fiber is not particularly limited, and a known method such as a dipping method or a spray method can be used.
• a known method such as a dipping method or a spray method can be used.
• the dipping method it is preferable to treat the fiber in a solution in which the concentration of the fiber treating agent is 1 to 150 g / L in terms of the ester compound represented by the general formula (1).
• the amount of the fiber treating agent attached to the fiber is preferably 0.02 to 5 parts by mass with respect to 100 parts by mass of the fiber in terms of the ester compound (1).
• the range is preferably 0.1 to 3 parts by mass, and more preferably 0.3 to 2 parts by mass.
• Fibers to which the fiber treating agent of the present invention can be applied include synthetic fibers such as polyester, polyamide, polyacryl, polypropylene, polyvinyl alcohol, polyvinyl chloride, polyvinylidene chloride, polyurethane, semi-synthetic fibers such as acetate, and the like. And mixed fibers of cotton, hemp, rayon, wool, and other natural fibers, and fibers made by dispersing inorganic compounds such as titania, zirconia, alumina, silica, and zeolite in synthetic fibers. May be added with a matting agent, a fluorescent brightening agent, an antistatic agent and a flame retardant. Among these, the fiber treating agent of the present invention is effective for synthetic fibers that are generally heat-treated at high temperatures. The fiber treating agent of the present invention can also be applied to fields where conventional oil agents such as cotton, linen fabric and woolen fabric are used.
• the application time of the fiber treating agent of the present invention is not particularly limited as long as it is after the time when the spun yarn is solidified, but it is usually applied to the yarn before the take-up roller.
• the fiber treating agent of the present invention can uniformly adhere to the yarn when applied, and can be easily removed by scouring performed before the dyeing process.
• the obtained yarns are provided as woven fabrics for fabrics, adhesive tape reinforcing materials, wire covering materials, tent fabrics, fabrics for industrial materials such as tire cords, and non-woven fabrics.
• the fiber treating agent of the present invention can be suitably used as a high-speed spinning oil or tire cord oil for synthetic fibers, but it is used for producing a drawing oil, a spinning direct-drawing oil, a spinning oil for producing textiles, a conning oil, and a woven fabric. It can be applied as a base oil such as a fiber entanglement oil for use as a composition in which an appropriate additive is blended.
• the processing agent for fibers containing the ester compound represented by following General formula (1).
• R 1 represents a hydrocarbon group having 8 to 24 carbon atoms
• R 2 represents an alkyl group, alkenyl group or cycloalkyl group having 7 to 23 carbon atoms
• EO represents an ethyleneoxy group
• PO represents a propyleneoxy group.
• l and n are the average number of moles of ethyleneoxy group added, l is a number from 0 to 15, and n is a number from 1 to 20.
• R 1 in the general formula (1) is a primary linear alkyl group or alkenyl group having 8 to 24 carbon atoms, preferably 12 to 18 carbon atoms, more preferably octyl alcohol, decyl alcohol, lauryl alcohol.
• the fiber treatment agent according to Item 1 which is a residue obtained by removing one hydroxy group from a natural higher alcohol selected from the group consisting of: Item 3.
• R 2 in the general formula (1) is a straight chain having 7 to 23 carbon atoms, preferably an alkyl or alkenyl group having 11 to 17 carbon atoms, and more preferably octanoic acid, decanoic acid, lauric acid, myristic acid , Palmitic acid, stearic acid, arachidic acid, behenic acid, palmitoleic acid, petrothelic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, erucic acid, isopalmitic acid (2-hexyldecanoic acid), 2-heptylundecanoic acid, A residue obtained by removing one carboxy group from a fatty acid selected from the group consisting of citronellic acid and isostearic acid, and more preferably removing one carboxy group from a fatty acid selected from the group consisting of lauric acid, stearic acid and oleic acid Item 3.
• Item 4. Item 4. The fiber treatment agent according to any one of Items 1 to 3, wherein l in the general formula (1) is preferably 0 to 5, more preferably 0 to 3, more preferably 0. Item 5.
• Item 5. The fiber treatment according to any one of Items 1 to 4, wherein m in the general formula (1) is preferably 0.8 to 15, more preferably 1 to 10, and more preferably 1.2 to 8. Agent.
• Item 6. Item 6.
• Item 7. Item 6.
• any one of Items 1 to 6, wherein (EO) l and (PO) m in ((EO) l- (PO) m ) in the general formula (1) are block-bonded in this order.
• Item 8. The fiber treatment agent according to any one of Items 1 to 7, further comprising an emulsifier component.
• Any one of Items 8 wherein the content of the emulsifier component is 0 to 50% by mass, preferably 0.1 to 20% by mass, and more preferably 0.1 to 5% by mass in the fiber treatment agent.
• Item 11. The fiber treatment agent according to any one of Items 1 to 10, wherein the content of the ester compound represented by the general formula (1) is 3 to 70% by mass and further contains water.
• Item 12. The fiber treatment agent according to any one of Items 1 to 11, which is used for synthetic fibers.
• a fiber processing method in which after 1 to 3 parts by mass, more preferably 0.3 to 2 parts by mass is attached, stretching and winding are performed.
• Item 15. Item 16. The fiber treatment method according to Item 15, wherein the fiber is treated in a solution having a fiber treatment agent concentration of 1 to 150 g / L in terms of an ester compound represented by the general formula (1).
• Item 16. Item 14. The fiber treatment agent for an ester compound according to any one of Items 1 to 13, which is used in a fiber production process, a processing process or a spinning process involving a heat process.
• Production Example 1 Production of ester compound (A) In an autoclave equipped with a stirrer, a temperature control device, and an automatic introduction device, 1082 g (4.0 moles) of stearyl alcohol (calcol 8098, manufactured by Kao Corporation) as a raw material alcohol Then, 3.2 g (0.08 mol) of potassium hydroxide was charged, dehydrated at 110 ° C. and 1.3 kPa for 30 minutes, and then purged with nitrogen. Thereafter, as an addition reaction of propylene oxide, the temperature was raised to 125 ° C., and 580.8 g (10.0 mol) of propylene oxide was introduced for aging operation.
• stearyl alcohol calcol 8098, manufactured by Kao Corporation
• Production Examples 2 to 18 Production of ester compounds (B) to (K) and comparative ester compounds (a) to (g) For the raw material alcohol shown in Table 1, the same addition reaction conditions as in Production Example 1 were obtained. After an addition reaction in the order of ethylene oxide having an average addition mole number of 1, propylene oxide having an average addition mole number of m and ethylene oxide having an average addition mole number of n, an esterification reaction was performed using the raw fatty acids shown in Table 1. Except for the above, the corresponding ester compounds (B) to (K) and comparative ester compounds (a) to (g) were produced using the same reaction apparatus, reaction procedure and conditions as in Production Example 1. Table 1 shows the respective esterification reaction rates (based on raw fatty acids) and the structural characteristics of the obtained ester compounds.
• Examples 1 to 11 and Comparative Examples 1 to 8 About the ester compound shown in Table 1, the external appearance property and heat resistance were evaluated by the following method. Moreover, the processing agent for fibers was prepared with the following method using the ester compound shown in Table 1, and the lubricity and emulsion stability were evaluated according to the following procedure. The results are summarized in Table 2.
• each ester compound shown in Table 1 was heated at an initial temperature of 20 ° C. to 10 ° C./min in an air stream.
• the temperature (T5) when a weight loss corresponding to 5% by weight of the initial weight occurred was measured and judged according to the following criteria.
• the results are shown in Table 2. Evaluation criteria: ⁇ : T5 is 200 ° C. or higher X: T5 is lower than 200 ° C.
• Test fibers (polyester filament yarn: 83 dtex, 36 filaments) were immersed in the obtained fiber treatment agent, and 1.5 parts by mass of the fiber treatment agent was adhered to 100 parts by mass of the fiber in terms of the amount of the ester compound. Thereafter, it was dried to obtain a test yarn.
• a friction measuring machine ( ⁇ meter instrument TWD-4, manufactured by Eiko Sokki Co., Ltd.) was used to make a metal by the traveling yarn method with an initial tension of 20 gf, a yarn speed of 500 m / min, and a friction angle of 180 °.
• the fiber treating agent of the present invention using the ester compound having a specific structure represented by the general formula (1) is excellent in all of the appearance properties, heat resistance, lubricity, and emulsion stability in water. Furthermore, the fiber treatment agent of the present invention can be easily washed and removed in scouring washing, and greatly contributes to smoothing of the fiber production process.

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• 2010
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