KR20210152001A - Treatment agents for synthetic fibers and synthetic fibers - Google Patents

Abstract

The present invention relates to component A comprising at least one selected from dicarboxylic acids having 1 to 16 carbon atoms and ester-forming derivatives thereof, and 2 to 4 carbon atoms per mole of a monovalent hydroxy compound having an aromatic ring in the molecule. of an alkylene oxide of more than 10 moles and added in a ratio of 100 moles or less, and an amount of an alkylene oxide having 2 to 4 carbon atoms in excess of 10 moles and 100 moles per mole of the monovalent carboxylic acid having an aromatic ring in the molecule A processing agent for synthetic fibers (excluding carbon fibers) comprising a diester compound formed from component B containing at least one selected from the compounds added in the following proportions.

Description

Treatment agents for synthetic fibers and synthetic fibers

The present invention relates to a processing agent for synthetic fibers that imparts excellent initial hydrophilic durability to synthetic fibers and provides excellent emulsion stability when dispersed in an aqueous medium, and synthetic fibers to which such processing agent for synthetic fibers is adhered.

For example, as hygiene products, such as a paper diaper, the product which coat|covered the surface of the super absorbent polymer with the synthetic fiber in order to absorb body fluid is known. Synthetic fibers covering the surface of the superabsorbent polymer are required to have excellent absorption properties, such as initial hydrophilic durability for rapidly absorbing repeated body fluids. Therefore, especially about hydrophobic synthetic fiber, in order to provide the said characteristic, the processing agent for synthetic fibers may be used. Moreover, emulsion stability is also required for the processing agent for synthetic fibers, when used with the form of the emulsion disperse|distributed to the aqueous medium.

Conventionally, for example, the processing agent for synthetic fibers disclosed by patent documents 1-3 is known.

Patent Document 1 discloses a water permeability imparting agent containing an ester compound of an adduct of 1 to 100 moles of an alkylene oxide of a monohydric aliphatic alcohol and a dihydric carboxylic acid.

Patent document 2 discloses about the chemical|medical agent for fibers containing 10 mol or less of ethylene oxide adducts, such as a polycyclic phenol, and the ester compound of dicarboxylic acid.

Patent Document 3 contains a polyether ester compound composed of a structural unit A such as aromatic dicarboxylic acid in a predetermined ratio, a structural unit B such as ethylene glycol, and a structural unit C such as polyoxyethylene polycyclic aromatic ether Disclosed is a treatment agent for polyester fibers to be used.

International Publication No. 2011-004713 Japanese Patent Laid-Open No. 2003-155666 Japanese Patent Laid-Open No. 2016-75002

However, in the conventional treatment agent, it was not possible to sufficiently achieve both the emulsion stability when dispersed in an aqueous medium and the initial hydrophilic durability desired for the synthetic fiber treated to be hydrophilic using the treatment agent.

The problem to be solved by the present invention is to provide a processing agent for synthetic fibers that provides excellent initial hydrophilic durability to synthetic fibers and obtains excellent emulsion stability when dispersed in an aqueous medium. Another problem to be solved by the present invention is to provide a synthetic fiber having excellent initial hydrophilic durability.

In this way, the present inventors discovered that the processing agent for synthetic fibers containing the diester compound formed from the following A component and the following B component is immediately suitable as a result of research in order to solve the said subject.

In order to solve the above problems, in the treatment agent for synthetic fibers (excluding carbon fibers) according to one aspect of the present invention, component A containing at least one selected from dicarboxylic acids having 1 to 16 carbon atoms and ester-forming derivatives thereof And, to 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule, more than 10 moles of an alkylene oxide having 2 to 4 carbon atoms and added in a ratio of 100 moles or less, and monovalent carboxyl having an aromatic ring in the molecule It is characterized in that it contains a diester compound formed of component B comprising at least one selected from compounds obtained by adding an alkylene oxide having 2 to 4 carbon atoms in an amount of more than 10 moles and not more than 100 moles per mole of the acid.

In the processing agent for synthetic fibers, the component A preferably contains at least one selected from unsaturated aliphatic dicarboxylic acids having 1 to 16 carbon atoms, aromatic dicarboxylic acids, and ester-forming derivatives thereof.

In the processing agent for synthetic fibers, the component B is a compound obtained by adding an alkylene oxide having 2 to 4 carbon atoms in a ratio of more than 10 moles and not more than 50 moles with respect to 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule. And it is preferable to include at least one selected from the group consisting of more than 10 moles of an alkylene oxide having 2 to 4 carbon atoms and added in a ratio of 50 moles or less with respect to 1 mole of the monovalent carboxylic acid having an aromatic ring in the molecule.

In the processing agent for synthetic fibers, the component B is a compound obtained by adding an alkylene oxide having 2 to 4 carbon atoms in a ratio of 15 mol or more and 25 mol or less with respect to 1 mol of the monovalent hydroxy compound having an aromatic ring in the molecule. and at least one compound selected from the group consisting of 15 mol or more and 25 mol or less of an alkylene oxide having 2 to 4 carbon atoms with respect to 1 mol of the monovalent carboxylic acid having an aromatic ring in the molecule.

In the processing agent for synthetic fibers, the monovalent hydroxy compound having an aromatic ring in the molecule that forms the component B is preferably a monovalent hydroxy compound having two or more aromatic rings in the molecule.

It is preferable that the said processing agent for synthetic fibers further contains at least one selected from an anionic surfactant, a cationic surfactant, a nonionic surfactant, a smoothing agent, an aliphatic alcohol, and a polyether modified silicone.

The synthetic fiber of another aspect of this invention has the said processing agent for synthetic fibers adhered, It is characterized by the above-mentioned.

It is preferable that the said synthetic fiber is a hydrophobic thing.

It is preferable that the said synthetic fiber is polyester.

According to the present invention, excellent initial hydrophilic durability is imparted to synthetic fibers, and excellent emulsion stability is obtained when dispersed in an aqueous medium.

(First embodiment)

EMBODIMENT OF THE INVENTION Hereinafter, 1st Embodiment which actualized the processing agent for synthetic fibers of this invention (henceforth simply called a processing agent) is demonstrated. The processing agent of this embodiment contains the diester compound which the following component A and the following B component couple|bonded by the esterification reaction or transesterification reaction. A diester compound may be used individually by 1 type of diester compound, and may be used in combination of 2 or more types of diester compounds.

Component A provided in the diester compound is a component comprising at least one selected from dicarboxylic acids having 1 to 16 carbon atoms and ester-forming derivatives thereof. Specific examples of such dicarboxylic acids and ester-forming derivatives of dicarboxylic acids include aliphatic dicarboxylic acids such as citric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, and maleic acid. and their anhydrides, dimethyl oxalate, dimethyl malonate, dimethyl succinate, dimethyl glutarate, dimethyl adipate, dimethyl fumarate, dimethyl maleate, dioctyl maleate, bis(2-ethylhexyl maleate), etc. ester-forming derivatives of carboxylic acid, phthalic acid (o-phthalic acid), terephthalic acid (p-phthalic acid), isophthalic acid (m-phthalic acid), 2,6-naphthalenedicarboxylic acid, and aromatic dicarboxylic acids such as 5-sulfoisophthalic acid carboxylic acid and anhydrides thereof, dibutyl phthalate, dimethyl terephthalate, diethyl terephthalate, bis(2-ethylhexyl terephthalate), dimethyl isophthalate, diethyl isophthalate, dioctyl isophthalate, dipropyl terephthalate, 2,6- and ester-forming derivatives of aromatic dicarboxylic acids such as naphthalenedicarboxylic acid dimethyl and 5-sulfoisophthalic acid-1,3-dimethyl. Among these, unsaturated fatty acid dicarboxylic acids, such as fumaric acid and maleic acid, aromatic dicarboxylic acids, such as terephthalic acid, isophthalic acid, 5-sulfoisophthalic acid, and those ester-forming derivatives are preferable. By using the processing agent using these compounds, the durable hydrophilicity of a synthetic fiber, especially initial stage hydrophilic durability improves. In addition, durable hydrophilicity refers to a performance indicating how long the hydrophilicity required for a synthetic fiber used for a predetermined purpose can be maintained, and in particular, the performance indicating how long the initial hydrophilicity of the synthetic fiber can be maintained. This is called initial hydrophilic durability.

Component B provided to the diester compound is a compound and molecule in which an alkylene oxide having 2 to 4 carbon atoms is added in a ratio of more than 10 moles and not more than 100 moles with respect to 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule. At least one selected from compounds obtained by adding an alkylene oxide having 2 to 4 carbon atoms in an amount of more than 10 moles and not more than 100 moles per mole of the monovalent carboxylic acid having an aromatic ring in it is included.

The monovalent hydroxy compound having an aromatic ring in the molecule constituting component B may be a monovalent hydroxy compound having one aromatic ring in the molecule, or may be a monovalent hydroxy compound having two or more aromatic rings. Among these, a monovalent hydroxy compound having two or more aromatic rings is preferable from the viewpoint of being excellent in the effect of improving the durable hydrophilicity of the synthetic fiber, particularly the initial hydrophilic durability. Specific examples of the monovalent hydroxy compound having one aromatic ring include monovalent aromatic alcohols having one aromatic ring, such as phenol, propylphenol, butylphenol, octylphenol, and tridecylphenol.

Specific examples of the monovalent hydroxy compound having two or more aromatic rings include tristyrenated phenol, tri(α-ethylbenzyl)phenol, tri(α-propylbenzyl)phenol, and tri(α-butylbenzyl)phenol. , distyreneated phenol, di(α-ethylbenzyl)phenol, di(α-propylbenzyl)phenol, di(α-butylbenzyl)phenol, monostyrenated phenol, mono(α-ethylbenzyl)phenol, mono(α- and propylbenzyl)phenol, mono(α-butylbenzyl)phenol, tribenzylphenol, dibenzylphenol, and monobenzylphenol.

As monovalent carboxylic acid which has an aromatic ring in the molecule|numerator which comprises B component, the monovalent carboxylic acid which has one aromatic ring in a molecule|numerator may be sufficient, and the monovalent carboxylic acid which has two or more aromatic rings may be sufficient. As a specific example of monovalent carboxylic acid which has an aromatic ring, monovalent|monohydric aromatic carboxylic acid etc. which have one aromatic ring, such as benzoic acid, are mentioned, for example.

Ethylene oxide, propylene oxide, butylene oxide, etc. are mentioned as a C2-C4 alkylene oxide which comprises B component. Among these, ethylene oxide is preferable from a viewpoint of improving the effect of this invention more. In addition, the alkylene oxide may be comprised as a random adduct, or may be comprised as a block adduct.

The number of moles added of an alkylene oxide having 2 to 4 carbon atoms to 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule, or the number of moles added of an alkylene oxide to 1 mole of a monovalent carboxylic acid having an aromatic ring in the molecule The lower limit is more than 10 moles, preferably 15 moles or more. By specifying in a range exceeding 10 moles, the hydrophilic properties that can be imparted to the synthetic fiber, in particular, initial hydrophilic durability and initial hydrophilicity are improved. Moreover, the emulsion stability of a processing agent, especially the emulsion stability in high temperature improves. Moreover, as a result of improving the fluidity|liquidity of a diester compound, the handling property of a processing agent improves more.

The upper limit of the said added mole number is 100 mol or less, Preferably it is 50 mol or less, More preferably, it is 25 mol or less. By prescribing to 100 mol or less, as a result of improving the fluidity|liquidity of a diester compound, the handling property of a processing agent improves more. Moreover, the durable hydrophilicity which can be provided to a synthetic fiber also improves. In addition, the added mole number of an alkylene oxide shows the average added mole number.

Specific examples of the component B include, for example, polyoxyethylene (the number of added moles of alkylene oxide (hereinafter the same) is 10.5 to 50 moles), tristyrenated phenyl ether, polyoxyethylene (10.5 to 30 moles) polyoxypropylene (10.5 to 30 moles) 30 mol) tristyrenated phenyl ether, polyoxyethylene (10.5 to 30 mol) tri (α-ethylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 mol) tri (α-propylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 moles) tri(α-butylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 moles) distyreneated phenyl ether, polyoxyethylene (10.5 to 30 moles) di(α-ethylbenzyl) phenyl ether, poly Oxyethylene (10.5 to 30 moles) di(α-propylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 moles) di(α-butylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 moles) monostyrenated phenyl Ether, polyoxyethylene (10.5 to 30 mol) mono (α-ethylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 mol) mono (α-propylbenzyl) phenyl ether, polyoxyethylene (10.5 to 30 mol) mono (α-butylbenzyl)phenyl ether, polyoxyethylene (10.5 to 30 moles) tribenzylphenyl ether, polyoxyethylene (10.5 to 30 moles) dibenzylphenyl ether, polyoxyethylene (10.5 to 30 moles) monobenzylphenyl ether , polyoxyethylene (10.5 to 30 moles) polyoxypropylene (10.5 to 30 moles) phenyl ether, polyoxyethylene (10.5 to 30 moles) phenyl ether, polyoxyethylene (10.5 to 30 moles) t-butylphenyl ether, poly oxyethylene (10.5-30 mol) benzoic acid ester etc. are mentioned.

Synthetic fibers to which the processing agent of the present embodiment is applied are synthetic fibers other than carbon fibers. Although it will not specifically limit if it is a synthetic fiber other than carbon fiber, From a viewpoint of exhibiting the effect of providing hydrophilicity to the surface of a synthetic resin, it is preferable that it is a hydrophobic synthetic fiber.

Examples of the hydrophobic synthetic fibers include polyester fibers, polyolefin fibers, polyamide fibers, and polyacrylonitrile fibers. These fibers may be composite synthetic fibers composed of two or more types. Specific examples of the polyester fiber include, for example, polyethylene terephthalate (PET), polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polylactic acid, and a composite polyester containing these polyester resins. fiber etc. are mentioned. Further, as the polyester fibers, modified polyester fibers such as basic or acid dyeable polyester fibers, antistatic polyester fibers, and flame-retardant polyester fibers may be applied. Specific examples of polyolefin fibers include polyethylene fibers, polypropylene fibers, and polybutene fibers. Moreover, as a polypropylene fiber, the modified polypropylene fiber which copolymerized various monomers, the composite polypropylene fiber of polyethylene and polypropylene, etc. may be applied.

Although the processing agent of this embodiment can be applied to any of a short fiber and a long fiber, it is preferable to apply to a short fiber. Short fibers generally correspond to those referred to as staples, and generally do not contain long fibers referred to as filaments. In addition, the length of the single fiber in this embodiment is although it will not specifically limit if it corresponds to a single fiber in this technical field, For example, it is preferable that it is 100 mm or less.

Although the processing agent of this embodiment contains the diester compound as demonstrated above, At least one further selected from an anionic surfactant, a cationic surfactant, a nonionic surfactant, a smoothing agent, an aliphatic alcohol, and polyether modified silicone It is preferable to include These components may be used individually by 1 type, and may be used in combination of 2 or more type. These components do not impair the properties of the diester compound, and reduce friction in the properties according to each component, for example, in the spinning process, drawing process, or spinning process of synthetic fibers, thereby preventing damage to fibers such as yarn breakage. Prevents properties.

A well-known anionic surfactant can be suitably employ|adopted as an anionic surfactant provided as the processing agent of this embodiment. Specific examples of the anionic surfactant include (1) phosphate ester salts of aliphatic alcohols such as lauryl phosphate ester salt, cetyl phosphate ester salt, octyl phosphate ester salt, oleyl phosphate ester salt, and stearyl phosphate ester salt, ( 2) Ethylene oxide in aliphatic alcohols such as polyoxyethylene (5 mol) lauryl ether phosphate ester salt, polyoxyethylene (5 mol) oleyl ether phosphate ester salt, and polyoxyethylene (10 mol) stearyl ether phosphate ester salt and phosphoric acid ester salts obtained by adding at least one alkylene oxide selected from propylene oxide, (3) laurylsulfonic acid ester salts, myristylsulfonic acid ester salts, cetylsulfonic acid ester salts, oleylsulfonic acid ester salts, stearylsulfonic acid ester salts, tetradecanesulfonic acid salts, C14 to 16 alkylsulfonic acid salts, sulfonic acid ester salts of aliphatic alcohols or aromatic alcohols such as dodecylbenzenesulfonate salts, (4) lauryl sulfate ester salts, oleyl sulfate ester salts, stearyl sulfate Sulfuric acid ester salts of aliphatic alcohols, such as ester salts, (5) polyoxyethylene (3 mole) lauryl ether sulfate ester salt, polyoxyethylene (5 mole) lauryl ether sulfate ester salt, polyoxyalkylene (polyoxyethylene Ethylene oxide in aliphatic alcohols such as 3 moles, 3 moles of polyoxypropylene) lauryl ether sulfate, polyoxyethylene (3 moles) oleyl ether sulfate, and polyoxyethylene (5 moles) oleyl ether sulfate. and sulfuric acid ester salts obtained by adding at least one alkylene oxide selected from propylene oxide; Sulfuric acid ester salts of fatty acids such as rapeseed oil fatty acid sulfate ester salt, palm oil fatty acid sulfuric acid ester salt, pork oil fatty acid sulfate ester salt, tallow fatty acid sulfuric acid ester salt, light oil fatty acid sulfate ester salt, (7) sulfuric acid ester salt of castor oil, sulfate ester of sesame oil Salt, sulfate ester salt of tall oil, sulfate ester salt of soybean oil, sulfate ester salt of rapeseed oil, sulfate ester salt of palm oil, Sulfuric acid ester salts of pig milk, sulfuric acid ester salts of tallow, sulfuric acid ester salts of fats and oils, such as sulfuric acid ester salts of light oil, (8) fatty acid salts such as lauric acid salt, oleic acid salt, and stearate, (9) dioctylsulfosuccinic acid The sulfosuccinic acid ester salt of aliphatic alcohols, such as a salt, etc. are mentioned. Examples of the counter ion of the anionic surfactant include alkali metal salts such as potassium salt and sodium salt, ammonium salt, and alkanolamine salts such as triethanolamine.

As a cationic surfactant used as the processing agent of this embodiment, a well-known cationic surfactant can be employ|adopted suitably. Specific examples of the cationic surfactant include lauryl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, and didecyl dimethyl ammonium chloride.

As a nonionic surfactant provided as the processing agent of this embodiment, a well-known nonionic surfactant can be employ|adopted suitably. Specific examples of the nonionic surfactant include (1) a compound 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, for example, polyoxyethylene dilauric acid ester , polyoxyethylene oleic acid ester, polyoxyethylene lauric acid ester methyl ether, polyoxyethylene oleic acid diester, polyoxyethylene octyl ether, polyoxyethylene lauryl ether, polyoxyethylene lauryl ether methyl ether, polyoxyethylene poly Oxypropylene lauryl ether, polyoxypropylene lauryl ether methyl ether, polyoxybutylene oleyl ether, polyoxyethylene polyoxypropylene nonyl ether, polyoxypropylene nonyl ether, polyoxyethylene polyoxypropylene octyl ether, polyoxyethylene Ether type nonionic surfactants, such as dodecyl ether, polyoxyethylene tridecyl ether, polyoxyethylene lauryl amino ether, polyoxyethylene lauroamido ether, polyoxyethylene tristylenide phenyl ether, (2) sorbitan Polyhydric alcohol partial ester type nonionic surfactants such as trioleate, sorbitan monooleate, sorbitan monostearate, and glycerin monolaurate; (3) polyoxyalkylene sorbitan trioleate, polyoxyalkylene palm oil , polyoxyalkylene hydrogenated castor oil, polyoxyalkylene hydrogenated castor oil, polyoxyalkylene hydrogenated castor oil trioctanoate, polyoxyalkylene hydrogenated castor oil, maleic acid ester, stearic acid ester, or oleic acid ester Alkylene polyhydric alcohol fatty acid ester type nonionic surfactant, (4) alkylamide type nonionic surfactant such as diethanolamine monolauroamide, (5) polyoxyethylenediethanolamine monooleylamide, polyoxyethylene la Polyoxyalkylene fatty acid amide type nonionic surfactant, such as urylamine and polyoxyethylene tallow amine, etc. are mentioned.

As a leveling agent provided as the processing agent of this embodiment, well-known leveling agents other than the diester compound mentioned above can be employ|adopted suitably. As a specific example of a smoothing agent, For example, (1) butyl stearate, octyl stearate, oleyl laurate, oleyl oleate, isopentacosanyl isostearate, octyl palmitate, isotridecyl stearate, etc. , an ester compound of an aliphatic monoalcohol and an aliphatic monocarboxylic acid, an ester compound of an aliphatic monocarboxylic acid and a (poly)oxyalkylene adduct obtained by adding an alkylene oxide having 2 to 4 carbon atoms to the aliphatic monoalcohol, (2) Aliphatic polyhydric alcohols and aliphatic monolaurates, such as 1,6-hexanediol didecanoide trimethylolpropane monooleate monolaurate, sorbitan tritoleate, sorbitan monooleate, sorbitan monostearate, and glycerin monolaurate A complete ester compound with a carboxylic acid, a complete ester compound of a (poly)oxyalkylene adduct obtained by adding an alkylene oxide having 2 to 4 carbon atoms to an aliphatic polyhydric alcohol and an aliphatic monocarboxylic acid, (3) dilauryl adipate; Complete ester compounds of aliphatic monoalcohols and aliphatic polyhydric carboxylic acids, such as dioleyl azelate, diisocetylthiodipropionate, and bispolyoxyethylene lauryl adipate, and alkylene oxides having 2 to 4 carbon atoms in aliphatic monoalcohols A complete ester compound of a (poly) oxyalkylene adduct with added aliphatic polyhydric carboxylic acid; An ester compound with an acid, an ester compound of an aliphatic monocarboxylic acid with a (poly)oxyalkylene adduct obtained by adding an alkylene oxide having 2 to 4 carbon atoms to an aromatic monoalcohol, (5) bisphenol A dilaurate, polyoxyethylene A complete ester compound of an aromatic polyhydric alcohol and an aliphatic monocarboxylic acid, such as bisphenol A dilaurate, a (poly)oxyalkylene adduct obtained by adding an alkylene oxide having 2 to 4 carbon atoms to an aromatic polyhydric alcohol, and an aliphatic monocarboxyl Complete ester compounds with acids, (6) aliphatic monoalcohols, such as bis2-ethylhexyl phthalate, diisostearyl isophthalate, and trioctyl trimellitate, and aromatic polyhydric carboxylic acids; of a complete ester compound of, a complete ester compound of a (poly)oxyalkylene adduct obtained by adding an alkylene oxide having 2 to 4 carbon atoms to an aliphatic monoalcohol, and an aromatic polyhydric carboxylic acid, (7) palm oil, palm oil, rapeseed oil, sunflower oil and natural oils such as soybean oil, castor oil, sesame oil, fish oil, and beef tallow, (8) mineral oil, and the like, known smoothing agents employed as treatment agents.

As the aliphatic alcohol provided as the processing agent of the present embodiment, a known aliphatic alcohol can be appropriately employed. Specific examples of the aliphatic alcohol include: (1) methyl alcohol, butyl alcohol, octyl alcohol, nonanol, lauryl alcohol, stearyl alcohol, seryl alcohol, isobutyl alcohol, 2-ethylhexyl alcohol, isododecyl alcohol; Isohexadecyl alcohol, isostearyl alcohol, isotetorakosanyl alcohol, 2-propyl alcohol, 12-eicosyl alcohol, vinyl alcohol, butenyl alcohol, hexadecenyl alcohol, oleyl alcohol, eicosenyl alcohol, 2- Monovalent aliphatic alcohols having 1 to 40 carbon atoms, such as methyl-2-propylene-1-ol, 6-ethyl-2-undecen-1-ol, 2-octen-5-ol, and 15-hexadecene-2-ol , (2) monohydric aromatic alcohols such as phenol, propylphenol, octylphenol, and tridecylphenol; (3)ethylene glycol, propylene glycol, butanediol, hexanediol, neopentyl glycol, glycerin, trimethylolpropane, pentaerythrite, etc. and divalent to tetravalent aliphatic alcohols.

A well-known polyether-modified silicone can be suitably employ|adopted as a polyether-modified silicone provided as the processing agent of this embodiment, There is no restriction|limiting in particular as a structure, For example, ABn-type polyether-modified silicone, a side chain type polyether-modified silicone Silicone, double-terminated polyether-modified silicone, alkylpolyether-modified silicone in which both polyether groups and alkyl groups are introduced into side chains or terminals, and polyether-chain terminal portions of side-chained polyether-modified silicone are blocked with an aliphatic compound or a fatty acid compound and those in which the polyether chain terminal portion of both-terminal polyether-modified silicone is blocked with an aliphatic compound or a fatty acid compound. It is preferable that the polyether modified silicone provided as the processing agent of this embodiment has the following structures, for example.

In Formula 1,

X represents an organic group represented by the following formula (2),

Y represents an organic group represented by the following formula (3),

The repetition of X and Y may be repeated in either block or random method, respectively,

a and b each represent an integer of 1 or more.

In Formula 2,

R ¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms.

In Formula 3,

R ² represents an alkylene group having 3 to 6 carbon atoms,

R ³ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an acyl group having 2 to 8 carbon atoms;

c and d represent integers such that c + d = 1 to 200 (however, c≧0, d≧0.).

The processing agent of this embodiment may contain water as a dispersion medium as needed.

(Second embodiment)

A second embodiment of the synthetic fiber according to the present invention will be described. The synthetic fiber of this embodiment is a synthetic fiber to which the processing agent of 1st Embodiment adheres. As a kind of synthetic fiber, synthetic fibers other than the carbon fiber similar to those mentioned in the description of 1st Embodiment are applied.

Although there is no restriction|limiting in particular in the ratio in which the processing agent (solvent is not included) of 1st Embodiment is made to adhere to synthetic fiber, It is preferable to make it adhere so that it may become a ratio of 0.1-3 mass % with respect to synthetic fiber. In addition, as the method of making a processing agent adhere, well-known methods, such as the roller oil supply method, the guide oil supply method using the metering pump, the immersion oil supply method, and the spray oil supply method, are employable, for example. An aqueous liquid may be sufficient as the form of the processing agent at the time of making a processing agent adhere to a synthetic fiber, for example. Moreover, a small amount of an organic solvent may be contained in a processing agent within the range which does not impair the effect of this invention.

In addition, in which process the processing agent is made to adhere to the fiber, it is not specifically limited, For example, you may make it adhere in the papermaking process at the time of manufacturing a nonwoven fabric other than the spinning process, an extending process, and spinning process of synthetic fiber.

The action and effect of the processing agent and synthetic fiber of this embodiment are demonstrated.

(1) In the processing agent of this embodiment, the outstanding hydrophilic property can be provided with respect to a synthetic fiber. In particular, excellent durable hydrophilicity, in particular, initial hydrophilic durability and initial hydrophilicity can be imparted to hydrophobic synthetic fibers.

(2) Furthermore, when a processing agent is disperse|distributed to an aqueous medium, the outstanding emulsion stability is obtained. In particular, it has excellent emulsion stability at room temperature of 25°C and emulsion stability at high temperature such as 80°C. Therefore, manufacturing characteristics can be improved in the papermaking process at the time of manufacturing a nonwoven fabric other than the spinning process, an extending process, and a spinning process of a synthetic fiber, etc.

(3) Since the diester compound contained in the treatment agent of the present embodiment has fluidity at room temperature or fluidity by heating, it is not necessary to dilute it with a solvent at the time of handling, so that handling and transportability can be remarkably improved. have.

In addition, you may change the said embodiment as follows.

- To the processing agent of this embodiment, as a stabilizer and an antistatic agent for maintaining the quality of a processing agent within the range which does not impair the effect of this invention, components normally used for processing agents, such as a coupling agent, antioxidant, and a ultraviolet absorber, are added. may be combined with

- Although the processing agent of this embodiment has the said diester compound as an essential component, it is the range which does not impair the effect of this invention, A mono|mono which generate|occur|produces in the reaction process of the said A component and the said B component. It does not prevent inclusion of reaction by-products, such as ester.

Example

Hereinafter, in order to demonstrate the structure and effect of this invention more concretely, although an Example etc. are mentioned, this invention is not limited to these Examples. In addition, in the description of the following examples and comparative examples, a part means a mass part, and % means mass %.

<Test Category 1 (Preparation of diester compound and treatment agent)>

(Example 1)

Synthesis of diester compound (E-1)

Phthalic anhydride (1 mol) as a dicarboxylic acid, polyoxyethylene (15 mol), tristyrenated phenyl ether (2 mol), and p-toluenesulfonic acid (0.1%) as a catalyst were put into a reaction vessel, and under a nitrogen atmosphere, 150 Esterification was carried out at ~ 220 °C for 12 hours.

(Example 2)

Synthesis of diester compound (E-2)

Dimethyl maleate (2 mol), an ester-forming derivative of dicarboxylic acid, polyoxyethylene (18 mol), tristyrenated phenyl ether (2 mol), and titanium tetrabutoxide (0.1%) as a catalyst were added to a reaction vessel, , the transesterification reaction was carried out for 8 hours while distilling off methanol produced at 150 to 220°C under a reduced pressure of 10 hPa or less.

(Examples 3 to 33, Comparative Examples 1 to 8)

Synthesis of diester compounds (E-3 to E-33, e-1 to e-8)

Examples 9, 10, 13, 15 to 18, 20 to 22, 24, 26, 32, 33 and each diester compound of Comparative Examples 2, 3, 5 and 7 using dicarboxylic acid as a raw material (E- 9, 10, 13, 15 to 18, 20 to 22, 24, 26, 32, 33, e-2, 3, 5, 7) uses each component shown in Table 1, and is the same as in Example 1 prepared by this method.

Each of the ester compounds of Examples and Comparative Examples 1, 4, and 6 other than the above using an ester-forming derivative of dicarboxylic acid as a raw material was prepared in the same manner as in Example 2.

Comparative Example 8 is a compound described in Example 1 of Patent Document 3 (Japanese Patent Laid-Open No. 2016-75002), specifically, a structural unit A (42.8 mol%) formed of dimethyl terephthalate, a composition formed of ethylene glycol A polyether ester compound (e-8) comprising the unit B (28.6 mol%) and the structural unit C (28.6 mol%) formed of polyoxyethylene (18 mol) tristyrenated phenyl ether was used.

Examples 1-33 and Comparative Examples 1-8 were prepared as a processing agent which consists of 100 mass parts of said each compound.

in Table 1

A-1: phthalic anhydride

A-2: maleic anhydride

A-3: maleic acid

A-4: isophthalic acid (m-phthalic acid)

A-5: terephthalic acid (p-phthalic acid)

A-6: Dimethyl terephthalate

A-7: diethyl isophthalate

A-8: dipropyl terephthalate

A-9: dibutyl phthalate

A-10: dioctyl isophthalate

A-11: Bis terephthalate (2-ethylhexyl)

A-12: dimethyl maleate

A-13: dioctyl maleate

A-14: Maleic acid bis(2-ethylhexyl)

A-15: 2,6-naphthalenedicarboxylic acid dimethyl

A-16: phthalic acid (o-phthalic acid)

A-17: oxalic acid

A-18: citric acid

A-19: Dimethyl succinate

A-20: adipic acid

A-21: dimethyl adipic acid

a-1: methyl benzoate

a-2: oleic acid

B-1: polyoxyethylene (15 mol) tristyrenated phenyl ether

B-2: polyoxyethylene (18 mol) tristyrenated phenyl ether

B-3: polyoxyethylene (20 mol) tristyrenated phenyl ether

B-4: polyoxyethylene (25 mol) monostyrenated phenyl ether

B-5: polyoxyethylene (23 mol) tribenzyl phenyl ether

B-6: polyoxyethylene (15 mol) benzylphenyl ether

B-7: polyoxyethylene (8 mol) polyoxypropylene (8 mol) random addition type tristyrenated phenyl ether

B-8: polyoxyethylene (10.5 mol) tristyrenated phenyl ether

B-9: polyoxyethylene (30 mol) tristyrenated phenyl ether

B-10: polyoxyethylene (40 mol) tristyrenated phenyl ether

B-11: polyoxyethylene (50 mol) tristyrenated phenyl ether

B-12: polyoxyethylene (15 mol) phenyl ether

B-13: polyoxyethylene (10 moles) polyoxypropylene (5 moles) block addition type phenyl ether

B-14: polyoxyethylene (15 mol) benzoic acid ester

B-15: polyoxyethylene (18 mol) benzoic acid ester

B-16: polyoxyethylene (15 mol) t-butylphenyl ether

B-17: polyoxyethylene (25 mol) t-butylphenyl ether

b-1: polyoxyethylene (7 mol) tristyrenated phenyl ether

b-2: polyoxyethylene (5 mol) tristyrenated phenyl ether

b-3: polyoxyethylene (10 mol) stearyl ether

b-4: polyoxyethylene (7 mol) stearyl ether

b-5: polyoxyethylene (10 mol) C14 to C60 alkyl ether

※1: Evaluation not carried out because emulsification could not be performed by either method of 25°C emulsification test or 80°C emulsification test

※2: In the emulsification test at 25°C and the emulsification test at 80°C, the test was not carried out because it cannot be dripped with the dropper at 25°C and 80°C

indicates

(Examples 34 to 66)

Preparation of the treatment agent of Examples 34-66

In Examples 34 to 66, each diester compound (E-1 to E-33) of Examples 1 to 33 was used as the diester compound. In addition, as other components (surfactant, leveling agent, aliphatic alcohol, or polyether-modified silicone), C-1 to C-33 shown below were used, respectively. The processing agents of Examples 34-66 were prepared by mixing each component shown in Table 2 in a predetermined ratio.

in Table 2

C-1: polyoxyethylene (3 mol) lauryl ether sulfate ester triethanolamine salt

C-2: sodium lauryl sulfate

C-3: lauryl phosphate potassium salt

C-4: octyl phosphate potassium salt

C-5: stearyl phosphate potassium salt

C-6: sodium dioctylsulfosuccinate

C-7: sodium dodecylbenzenesulfonate

C-8: Tallow sulfuric acid ester sodium salt

C-9: sodium C14 to 16 alkylsulfonate

C-10: polyoxyethylene (6 mol) lauryl ether

C-11: methyl ether of polyoxyethylene (6 mol) lauryl ether

C-12: polyoxyethylene (2 mol) polyoxypropylene (6 mol) lauryl ether

C-13: polyoxyethylene (6 mol) tristyrenated phenyl ether

C-14: Polyoxyethylene (20 mol) hydrogenated castor oil ester

C-15: polyoxyethylene (30 mol) castor oil ester

C-16: Maleic and stearic acid esters of polyoxyethylene (20 mol) hydrogenated castor oil esters

C-17: oleic acid ester of polyoxyethylene (25 mol) hydrogenated castor oil ester

C-18: polyoxyethylene (10 mol) castor oil fatty acid

C-19: polyoxyethylene (10 mol) palm oil fatty acid

C-20: polyoxyethylene (10 mol) laurylamine

C-21: polyoxyethylene (15 mol) tallow amine

C-22: polyoxyethylene (20 mol) sorbitan monooleate

C-23: polyoxyethylene (20 mol) sorbitan monostearate

C-24: polyoxyethylene (20 mol) sorbitan trioleate

C-25: sorbitan monooleate

C-26: sorbitan monostearate

C-27: palm oil

C-28: potassium oleate

C-29: oleyl alcohol

C-30: octyl alcohol

C-31: 2-ethylhexanol

C-32: propylene glycol

C-33: polyether modified silicone

indicates

<Test Category 2 (Preparation of 5% aqueous solution)>

In a 200 mL beaker, 95 g of water at 25° C. was weighed. While stirring this at 450 rpm, after adding 5 g of the processing agent containing the ester compound of each Example and each comparative example at 25 degreeC, it stirred for 5 minutes, and prepared the 5% aqueous solution.

<Test category 3 (preparation of short fibers)>

For 5 g of raw material fibers (fineness 1.3 dtex, short polyethylene terephthalate fibers with a length of 38 mm), 5 g of 0.2% aqueous solution prepared by diluting 5% aqueous solution again with water in each example prepared in Test Category 2 was uniformly attached using a spray. , dried for 1 hour in a dryer at 80 °C.

About the obtained short fiber sample, as shown below, evaluation of durability hydrophilicity, initial stage hydrophilicity, and initial stage hydrophilic durability was performed.

<Test Category 4 (Evaluation)>

・Durable hydrophilicity

(1) 5 g of the monofilament sample obtained in Test Category 3 was subjected to a wire basket as described in clause 5.1 of STANDARD PROCEDURE: NWSP 010.1.R0(15) in "NONWOVENS STANDARD PROCEDURES 2015 EDITION" (published by EDANA (European Disposables And Nonwovens Association)) evenly fill in

(2) Weigh 1000g of 25℃±1℃ water in a 1L beaker.

(3) The wire basket containing the short fiber sample is dropped into the water from the height of 25mm of the liquid level.

(4) Measure the time until the entire wire basket sinks below the liquid level.

(5) A sample of short fibers is taken out from the wire basket, dehydrated until the moisture content becomes 50%, and then dried at 80° C. for 1 hour.

(6) Repeat steps (2) to (5) until the wire basket does not sink within 60 seconds.

Results based on the following evaluation criteria are shown in the "durable hydrophilicity" column of Tables 1 and 2.

・Evaluation criteria for durable hydrophilicity

◎ (Excellent): If the number of times that the entire wire basket is submerged in water within 60 seconds is more than 10 times

○ (Good): If the number of times that the entire wire basket sinks in water within 60 seconds is more than 5 times and less than 10 times

Х (Bad): If the number of times the entire wire basket is submerged in water within 60 seconds is less than 5 times

・Initial hydrophilicity

(1) 5 g of the single fiber sample obtained in Test Category 3 is uniformly filled in the wire basket described in Section 5.1 of the "STANDARD PROCEDURE: NWSP 010.1.R0(15)".

(2) Weigh 1000g of 25℃±1℃ water in a 1L beaker.

(3) The wire basket containing the short fiber sample is dropped into the water from the height of 25mm of the liquid level.

(4) Measure the time until the entire wire basket sinks below the liquid level.

Results based on the following evaluation criteria are shown in the "initial hydrophilicity" column of Tables 1 and 2.

・Evaluation criteria for initial hydrophilicity

◎ (Excellent): When the entire wire basket is submerged in water within 5 seconds

Х (Bad): When it takes more than 5 seconds for the entire wire basket to sink into the water.

・Initial hydrophilic durability

(1) 5 g of the single fiber sample obtained in Test Category 3 is uniformly filled in the wire basket described in Section 5.1 of the "STANDARD PROCEDURE: NWSP 010.1.R0(15)".

(2) Weigh 1000g of 25℃±1℃ water in a 1L beaker.

(3) The wire basket containing the short fiber sample is dropped into the water from the height of 25mm of the liquid level.

(4) Measure the time until the entire wire basket sinks below the liquid level.

(5) A sample of short fibers is taken out from the wire basket, dehydrated until the moisture content becomes 50%, and then dried at 80° C. for 1 hour.

(6) The steps (2) to (5) are repeated until the wire basket does not sink within 10 seconds.

Results based on the following evaluation criteria are shown in the "initial hydrophilic durability" column of Tables 1 and 2.

・Evaluation criteria for initial hydrophilic durability

◎ (Excellent): If the number of times that the entire wire basket is submerged in water within 10 seconds is more than 8 times

○ (Good): If the number of times that the entire wire basket sinks in water within 10 seconds is 4 or more and less than 8 times

Х (Bad): When the number of times the entire wire basket is submerged in water within 10 seconds is less than 4 times

·25℃ emulsification

(1) 95 g of 25 degreeC water is added to a 200 mL beaker, and it stirs at 450 rpm, keeping warm in a 25 degreeC water bath.

(2) 5 g of the processing agent as described in each example heated at 25 degreeC or 80 degreeC is dripped with a dropper.

(3) After dripping, stirring is performed for 5 minutes, and the emulsified state immediately after stirring is confirmed.

Results based on the following evaluation criteria were shown in the "25°C emulsification" column of Tables 1 and 2.

・Evaluation criteria for emulsification at 25°C

◎ (Excellent): When uniformly dispersed or emulsified, and there is no suspended matter or sediment

Х (poor): If it is not uniformly dispersed or emulsified, and suspended solids or sediments remain

・80℃ emulsification

(1) Add 95 g of water at 80° C. to a 200 mL beaker, and stir at 450 rpm while keeping warm in a water bath at 80° C.

(2) 5 g of the processing agent as described in each example heated at 25 degreeC or 80 degreeC is dripped with a dropper.

(3) After dripping, stirring is performed for 5 minutes, and the emulsified state immediately after stirring is confirmed.

Results based on the following evaluation criteria are shown in the "80°C emulsification property" column of Tables 1 and 2.

・Evaluation criteria for emulsification at 80°C

◎ (Excellent): When uniformly dispersed or emulsified, and there is no suspended matter or sediment

Х (poor): If it is not uniformly dispersed or emulsified, and suspended solids or sediments remain

・Handling properties

(1) 20 g of the processing agent as described in each example of 25 degreeC or 80 degreeC is added to a 100 mL beaker.

(2) Hold the beaker at a height of 10cm, and tilt the entrance of the beaker 90 degrees.

(3) It is confirmed whether the processing agent of each example flows out from a beaker from a beaker within 20 seconds, and when it flows out, it is judged that there exists fluidity|liquidity.

Results based on the following evaluation criteria are shown in the "handling property" column of Tables 1 and 2.

・Evaluation criteria for handling properties

◎ (Excellent): When there is fluidity under both conditions of 25°C and 80°C

○ (Good): When there is fluidity only under the condition of 80℃

Х (poor): When there is no fluidity under both conditions of 25°C and 80°C

As is clear from the results in Tables 1 and 2 above, according to the present invention, hydrophilic properties such as excellent initial hydrophilic durability can be imparted to synthetic fibers. Moreover, when it disperse|distributes to an aqueous medium, the outstanding emulsion stability is obtained. Moreover, it is excellent in the fluidity|liquidity at the time of handling, and handling property can be improved.

Claims (9)

It is a processing agent for synthetic fibers used for processing of synthetic fibers other than carbon fibers,
A component comprising at least one selected from dicarboxylic acids having 1 to 16 carbon atoms and ester-forming derivatives thereof;
A compound obtained by adding more than 10 moles of an alkylene oxide having 2 to 4 carbon atoms and not more than 100 moles per mole of the monovalent hydroxy compound having an aromatic ring in the molecule, and a monovalent carboxylic acid having an aromatic ring in the molecule Component B comprising at least one selected from compounds obtained by adding an alkylene oxide having 2 to 4 carbon atoms in a ratio of more than 10 moles and not more than 100 moles per 1 mole
A processing agent for synthetic fibers comprising a diester compound formed from The processing agent for synthetic fibers according to claim 1, wherein the component A contains at least one selected from unsaturated aliphatic dicarboxylic acids having 1 to 16 carbon atoms, aromatic dicarboxylic acids, and ester-forming derivatives thereof. The compound according to claim 1 or 2, wherein the component B contains more than 10 moles of an alkylene oxide having 2 to 4 carbon atoms with respect to 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule in a ratio of 50 moles or less. Synthesis comprising at least one selected from a compound obtained by adding an alkylene oxide having 2 to 4 carbon atoms in a ratio of more than 10 moles and not more than 50 moles to 1 mole of a monovalent carboxylic acid having an aromatic ring in the molecule. A treatment agent for textiles. The amount of the alkylene oxide having 2 to 4 carbon atoms per 1 mole of the monovalent hydroxy compound having an aromatic ring in the molecule, in the component B, is 15 moles or more and 25 moles or less. At least one selected from compounds added in a ratio of, and compounds added in a ratio of 15 moles or more and 25 moles or less of an alkylene oxide having 2 to 4 carbon atoms with respect to 1 mole of a monovalent carboxylic acid having an aromatic ring in the molecule A processing agent for synthetic fibers comprising a. The synthesis according to any one of claims 1 to 4, wherein the monovalent hydroxy compound having an aromatic ring in the molecule forming the component B is a monovalent hydroxy compound having two or more aromatic rings in the molecule. A treatment agent for textiles. The synthetic fiber according to any one of claims 1 to 5, further comprising at least one selected from anionic surfactants, cationic surfactants, nonionic surfactants, leveling agents, aliphatic alcohols, and polyether-modified silicones. solvent treatment. The synthetic fiber to which the processing agent for synthetic fibers in any one of Claims 1-6 is adhered, The synthetic fiber characterized by the above-mentioned. The synthetic fiber according to claim 7, wherein the synthetic fiber is hydrophobic. The synthetic fiber according to claim 8, wherein the synthetic fiber is polyester.