CN109863270B - Fiber treatment agent - Google Patents
Fiber treatment agent Download PDFInfo
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- CN109863270B CN109863270B CN201780065354.6A CN201780065354A CN109863270B CN 109863270 B CN109863270 B CN 109863270B CN 201780065354 A CN201780065354 A CN 201780065354A CN 109863270 B CN109863270 B CN 109863270B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
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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
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/262—Sulfated compounds thiosulfates
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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
- 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
- D06M15/507—Polyesters
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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
- 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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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
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- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The purpose of the present invention is to provide a fiber treatment agent that can achieve both washing durability and dispersibility in water. In order to achieve the above object, the fiber treatment agent of the present invention is characterized by comprising the following components (a) to (C), and the following component (a) is a copolymer obtained by polymerizing at least the monomers of the following (i) to (iii). (A) A branched polyester resin (B) water (C) a nonionic surfactant having an aromatic ring (i) at least one of a divalent aromatic carboxylic acid and a derivative thereof (ii) a diol (iii) a polyhydric alcohol having 3 or more hydroxyl groups.
Description
Technical Field
The present invention relates to a fiber treatment agent.
Background
For example, fiber treatment agents are used for the purpose of imparting various functions to fibers.
As the fiber treatment agent, for example, a durable antistatic agent using a polyester resin is known (patent document 1). Further, for example, there is a fiber treatment agent containing a linear polyester resin, a solvent, and a nonionic surfactant (patent document 2).
Documents of the prior art
Patent document
[ patent document 1 ] Japanese examined patent publication No. 38-11298
[ patent document 2 ] Japanese examined patent publication No. 44-3967
Disclosure of Invention
Problems to be solved by the invention
In the fiber treatment agent, it is important that the washing durability which imparts the function to the fiber can be maintained even after washing.
However, when the washing durability of the fiber treatment agent is improved, the dispersibility in water is lowered, and it is difficult to obtain a liquid capable of processing fibers. On the other hand, when the dispersibility of the fiber treatment agent in water is attempted to be improved, the washing durability is lowered. This makes it difficult to achieve both washing durability in the fiber treatment agent and dispersibility in water.
Accordingly, an object of the present invention is to provide a fiber treatment agent capable of achieving both washing durability and dispersibility in water.
Means for solving the problems
In order to achieve the above object, the fiber treatment agent of the present invention comprises the following components (A) to (C),
the component (A) is a copolymer obtained by polymerizing at least the monomers (i) to (iii) below.
(A) Branched polyester resins
(B) Water (W)
(C) Nonionic surfactant having aromatic ring
(i) At least one of divalent aromatic carboxylic acid and derivative thereof
(ii) Diols
(iii) Polyols having more than 3 hydroxyl groups
Effects of the invention
The fiber treatment agent of the present invention can have both washing durability and dispersibility in water.
Detailed Description
The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following description.
In the monomer (i) of the fiber-treating agent of the present invention, the divalent aromatic carboxylic acid may be at least one of terephthalic acid and isophthalic acid, for example.
In the monomer (ii) of the fiber treatment agent of the present invention, the diol may be at least one of ethylene glycol and polyethylene glycol, for example.
The fiber treatment agent of the present invention may further contain, for example, an aromatic sulfonate.
The fiber treatment agent of the present invention may be, for example, a durable antistatic agent for fibers.
[1. fiber-treating agent ]
The fiber-treating agent of the present invention is characterized by comprising the following components (A) to (C),
the component (A) is a copolymer obtained by polymerizing at least the monomers (i) to (iii) below.
(A) Branched polyester resins
(B) Water (W)
(C) Nonionic surfactant having aromatic ring
(i) At least one of divalent aromatic carboxylic acid and derivative thereof
(ii) Diols
(iii) Polyols having more than 3 hydroxyl groups
The present inventors have found that a branched polyester resin can be obtained by copolymerizing (co-condensing) a polyhydric alcohol having 3 or more hydroxyl groups with a diol and at least one of a divalent aromatic carboxylic acid and a derivative thereof, thereby obtaining high washing durability. Further, it has been found that the branched polyester resin has good dispersibility in water when a nonionic surfactant having an aromatic ring is used as a dispersant. Thus, the present inventors have obtained a fiber treatment agent of the present invention that can achieve both washing durability and dispersibility in water.
(1) Component (A): branched polyester resins
In the fiber-treating agent of the present invention, the branched polyester resin (component (a)) is a copolymer obtained by polymerizing at least the monomers of the following (i) to (iii) as described above.
In the monomer (i), the divalent aromatic carboxylic acid (aromatic dicarboxylic acid) is not particularly limited, and examples thereof include aromatic dicarboxylic acids having 8 to 20 carbon atoms. Specific examples of the divalent aromatic carboxylic acid include phthalic acid, isophthalic acid, terephthalic acid, and 2, 6-naphthalenedicarboxylic acid. Examples of the derivative of the aromatic dicarboxylic acid include acid anhydrides, lower alcohol esters, and acid halides of the aromatic dicarboxylic acid. Examples of the lower alcohol ester include esters of lower alkanols, and more specifically, esters of linear or branched alkanols having 1 to 3 carbon atoms. Examples of the lower alkyl ester of the aromatic dicarboxylic acid include monomethyl ester, dimethyl ester, monoethyl ester, and diethyl ester, and more specifically, dimethyl isophthalate and dimethyl terephthalate. Examples of the acid halide of the aromatic dicarboxylic acid include monochloride, dichloride, monobromide, dibromide, and the like. Among the aromatic dicarboxylic acids and derivatives thereof, aromatic dicarboxylic acids and methyl esters thereof are preferable, and aromatic dicarboxylic acids having 8 to 12 carbon atoms and methyl esters thereof are more preferable from the viewpoint of washing durability. Specific examples thereof include terephthalic acid, dimethyl terephthalate, isophthalic acid, dimethyl isophthalate, phthalic acid, and dimethyl phthalate. In the present invention, the divalent aromatic carboxylic acid and the derivative thereof may be used alone or in combination of two or more.
In the monomer (ii), examples of the diol include aliphatic diols, alicyclic diols, aromatic diols, and alkylene oxide adducts thereof. In the present invention, the diol of the monomer (ii) may be a compound having 2 hydroxyl groups in the molecule, and the hydroxyl group may be an alcoholic hydroxyl group or a phenolic hydroxyl group. Examples of the aliphatic diol include alkylene diols and polyalkylene glycols derived from straight-chain or branched alkylene groups. Specific examples of the aliphatic diol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 3-methyl-1, 5-pentanediol, 1, 6-hexanediol, neopentyl glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, polypropylene glycol, and a polyoxyethylene-polyoxypropylene block copolymer. The molecular weight of the polyalkylene glycol (e.g., polyethylene glycol) is not particularly limited, and may be, for example, 300 or more, 600 or more, or 1000 or more, and may be, for example, 10,000 or less, 8000 or less, or 6000 or less. Examples of the alicyclic diol include 1, 4-cyclohexanedimethanol and hydrogenated bisphenol A. Examples of the aromatic diol include bisphenol a, bisphenol S, and hydroquinone. Among these diols, from the viewpoint of affinity with water and stability of the fiber treatment agent over time, a diol having an oxyethylene group such as polyethylene glycol is preferable. The diol may be used alone or in combination of two or more.
In the above monomer (iii), the polyol having 3 or more hydroxyl groups may be, for example, a triol, a tetraol or a polyol having 5 or more hydroxyl groups. Examples of the polyol having 3 or more hydroxyl groups include aliphatic polyols, alicyclic polyols, aromatic polyols, and alkylene oxide adducts thereof. In the polyol having 3 or more hydroxyl groups, the hydroxyl group may be an alcoholic hydroxyl group or a phenolic hydroxyl group. Examples of the triol include glycerol, trimethylolpropane and alkylene oxide adducts thereof. Examples of the tetrols include pentaerythritol and alkylene oxide adducts thereof. Examples of the polyhydric alcohol having 5 or more hydroxyl groups include sorbitol and alkylene oxide adducts thereof. Further, the above-mentioned polyhydric alcohol having 3 or more hydroxyl groups may be used in only 1 kind or in combination of plural kinds.
The branched polyester resin (component (a)) may or may not contain any component other than the monomers (i) to (iii) as a copolymerization component. The optional component is not particularly limited, and examples thereof include aliphatic dicarboxylic acids or lower alkyl esters thereof (e.g., linear dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, and pimelic acid or methyl esters thereof; dicarboxylic acids having a side chain such as methylmalonic acid, methylsuccinic acid, and methylglutaric acid, and alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid).
In the fiber treatment agent of the present invention, the content of the branched polyester resin (component (a)) is not particularly limited, and may be, for example, 10 mass% or more, 20 mass% or more, or 30 mass% or more, or 70 mass% or less, 60 mass% or less, or 50 mass% or less with respect to the mass of all components other than the water (component (B)). From the viewpoint of stability of the dispersion, it is preferable that the content of the branched polyester resin (component (a)) is not excessive. From the viewpoint of durable antistatic performance, the content of the branched polyester resin (component (a)) is preferably not too small.
The weight average molecular weight of the branched polyester resin (component (a)) is not particularly limited, but is preferably 8000 or more, 10000 or more, 15000 or more, or 20000 or more, for example, preferably 50000 or less, 40000 or less, 35000 or less, or 30000 or less.
(2) Process for producing branched polyester resin (component (A))
The method for producing the branched polyester resin (component (a)) is not particularly limited, and for example, the branched polyester resin can be produced by copolymerizing the monomers (i) to (iii). Further, as described above, any component other than the above-mentioned monomers (i) to (iii) may be copolymerized, or any component may not be copolymerized. The amount of the monomer (i) used is not particularly limited, but is, for example, preferably 5% by mass or more, 10% by mass or more, or 12% by mass or more, preferably 50% by mass or less, 30% by mass or less, or 20% by mass or less, of the whole copolymerization component. The amount of the monomer (ii) used is not particularly limited, and is, for example, preferably 50 mass% or more, 60 mass% or more, or 70 mass% or more, preferably 94 mass% or less, 90 mass% or less, or 86 mass% or less, of the whole copolymerization component. The amount of the monomer (iii) used is also not particularly limited, and is, for example, preferably 0.05% by mass or more, 0.1% by mass or more, or 0.12% by mass or more, preferably 1% by mass or less, 0.5% by mass or less, or 0.3% by mass or less, of the whole copolymerization component. The above-mentioned optional components may be used or may not be used, and when they are used, they may be, for example, 0.1 mass% or more or 1 mass% or more, or 10 mass% or less or 3 mass% or less of the whole copolymerization component.
The copolymerization method is also not particularly limited, and for example, a known method or a method referred to a known method may be used. Specifically, for example, a method in which the monomer (i) and a diol (e.g., ethylene glycol) are subjected to esterification reaction or transesterification reaction in the presence of an appropriate catalyst, and then the monomer (ii) and the monomer (iii) are added to conduct polycondensation reaction under reduced pressure is exemplified. In the esterification reaction or transesterification reaction between the monomer (i) and the diol, for example, the diol may also serve as a solvent. The amount of the diol used is also not particularly limited, and is, for example, preferably 80% by mass or more, 100% by mass or more, or 120% by mass or more, preferably 300% by mass or less, 250% by mass or less, or 200% by mass or less of the monomer (i). The catalyst is also not particularly limited, and examples thereof include zinc oxide, zinc acetate, manganese acetate, and antimony trioxide. The reaction time of the esterification reaction or the transesterification reaction is not particularly limited, and is, for example, preferably 0.3 hours or more, 0.5 hours or more, or 0.7 hours or more, and preferably 3 hours or less, 2 hours or less, or 1.5 hours or less. The reaction temperature is also not particularly limited, and is, for example, preferably 140 ℃ or more, 160 ℃ or more, or 170 ℃ or more, preferably 220 ℃ or less, 200 ℃ or less, or 190 ℃ or less. In the polycondensation reaction under reduced pressure, the reaction time is not particularly limited, and is, for example, preferably 1 hour or more, 1.5 hours or more, or 2 hours or more, and preferably 8 hours or less, 5 hours or less, or 4 hours or less. The reaction temperature is also not particularly limited, and is, for example, preferably 200 ℃ or higher or 220 ℃ or higher, and preferably 280 ℃ or lower or 260 ℃ or lower. In this production method, the monomer (i) may be, for example, an ester of an aromatic dicarboxylic acid, and the monomer (ii) may be, for example, a polyalkylene glycol such as polyethylene glycol. Further, a polycarboxylic acid may be mixed with the branched polyester resin (component (a)) produced by copolymerization. Examples of the polycarboxylic acid include dicarboxylic acids. By containing the dicarboxylic acid, for example, an effect of improving antistatic performance can be obtained. The dicarboxylic acid is not particularly limited, and examples thereof include oxalic acid, citric acid, tartaric acid, maleic acid, adipic acid, and salicylic acid. Examples of the polycarboxylic acid include エ ethylenediaminetetraacetic acid and sodium nitrilotriacetate which are compounds containing 3 or more carboxyl groups. When the polycarboxylic acid is mixed with a branched polyester resin (component (a)), the mass of the polycarboxylic acid is contained in the content of the branched polyester resin (component (a)) in the fiber treatment agent of the present invention.
(3) Component (B): water (W)
The water (component (B)) is not particularly limited, and may be, for example, tap water, distilled water, ion-exchanged water, or the like. From the viewpoint of cost, tap water or the like is preferable.
In the fiber treatment agent of the present invention, the content of the water (component (B)) is not particularly limited, and may be, for example, 200 mass% or more, 400 mass% or more, or 1000 mass% or more, or 2500 mass% or less, 2000 mass% or less, or 1700 mass% or less with respect to the mass of all components other than the water (component (B)). From the viewpoint of durable antistatic performance, it is preferable that the content of water (component (B)) is not excessive. From the viewpoint of stability of the dispersion, it is preferable that the content of the water (component (B)) is not too small.
(4) Component (C): nonionic surfactant having aromatic ring
The nonionic surfactant having an aromatic ring (component (C)) is not particularly limited, and examples thereof include alkylene oxide adducts of aromatic compounds. More specifically, for example, alkylene oxide adducts of bisphenol A, alkylene oxide adducts of styrenated phenols, alkylene oxide adducts of β -naphthol, alkylene oxide adducts of benzyl ether, and the like can be cited. As the alkylene oxide, for example, EO (ethylene oxide) is cited. The styrenated phenol may be, for example, a tristyrenated phenol. Further, the above-mentioned component (C) may be used in only one kind or in combination of two or more kinds.
In the fiber-treating agent of the present invention, the content of the nonionic surfactant having an aromatic ring (component (C)) is not particularly limited, and may be, for example, 15 mass% or more, 20 mass% or more, or 25 mass% or more, or 80 mass% or less, 70 mass% or less, or 60 mass% or less with respect to the mass of all components other than the water (component (B)). The content of the nonionic surfactant having an aromatic ring (component (C)) may be, for example, 30 to 300 mass%, 50 to 200 mass%, or 70 to 150 mass% with respect to the mass of the branched polyester resin (component (A)). From the viewpoint of durable antistatic performance, it is preferable that the content of the component (C) is not too large. From the viewpoint of dispersibility in water, the content of the component (C) is preferably not too small.
(5) Optional ingredients
The fiber-treating agent of the present invention may contain any components other than the above components (a) to (C), or may not contain any of the above components. Examples of the optional component include aromatic sulfonates and the like. By containing the aromatic sulfonate, for example, an effect of improving the antistatic performance immediately after the fiber is processed (in an unwashed state) can be obtained. The aromatic sulfonic acid salt is not particularly limited, and examples thereof include salts of sulfonic acids such as p-toluenesulfonic acid, m-xylenesulfonic acid, and cumenesulfonic acid. The aromatic sulfonate may be, for example, a salt of any metal, and may be, for example, a salt of an alkali metal (sodium, potassium, etc.), an alkaline earth metal (calcium, magnesium, etc.), or the like. The aromatic sulfonic acid salt is particularly preferably a sodium salt from the viewpoint of antistatic performance, and examples thereof include sodium p-toluenesulfonate, sodium m-xylenesulfonate, and sodium cumenesulfonate. Examples of the other optional components include cationic surfactants. From the viewpoint of dispersibility in water, it is preferable to contain a cationic surfactant. The cationic active agent is not particularly limited, and examples thereof include quaternary ammonium salts such as monoalkylammonium chloride and dialkylammonium chloride. The quaternary ammonium salt is particularly preferably dicocoalkyl dimethyl ammonium chloride or dihydrogenated tallow alkyl dimethyl ammonium chloride.
In the fiber treatment agent of the present invention, the content of the optional component is not particularly limited. For example, when the aromatic sulfonate is added, the mass of the aromatic sulfonate may be, for example, 10 mass% or more, 15 mass% or more, or 20 mass% or more, or 50 mass% or less, 45 mass% or less, or 40 mass% or less, with respect to the mass of all components other than the water (component (B)). The mass of the aromatic sulfonate may be, for example, 0.1 to 10 mass%, 1 to 5 mass%, or 1.5 to 4.5 mass% with respect to the total mass of the fiber treatment agent of the present invention including the water (component (B)). From the viewpoint of stability of the dispersion, it is preferable that the content of the aromatic sulfonate is not excessive. In addition, from the viewpoint of improving the antistatic performance of the fiber immediately after processing (in an unwashed state), it is preferable that the content of the aromatic sulfonate is not too small.
The mass of the aromatic sulfonate may be, for example, 50 mass% or more, 60 mass% or more, or 70 mass% or more, or 200 mass% or less, 160 mass% or less, or 140 mass% or less, with respect to the mass of the nonionic surfactant having an aromatic ring (component (C)). From the viewpoint of stability of the dispersion, it is preferable that the content of the aromatic sulfonate is not excessive. In addition, from the viewpoint of improving the antistatic performance of the fiber immediately after processing (in an unwashed state), the content of the aromatic sulfonate is preferably not too small.
[2. method for producing fiber-treating agent ]
The method for producing the fiber-treating agent of the present invention is not particularly limited, and for example, all components may be mixed and dispersed in the water (component (B)) except for the water (component (B)). Specifically, for example, the following method can be performed.
First, the branched polyester resin (component (a)) and the nonionic surfactant having an aromatic ring (component (C)) are mixed and dissolved while heating. The heating temperature is not particularly limited, and may be, for example, 80 ℃ or more or 100 ℃ or more, or 180 ℃ or less or 160 ℃ or less. The heating time is also not particularly limited, and may be, for example, 10 minutes or more, or 20 minutes or more, or 2 hours or less, or 1.5 hours or less.
On the other hand, the water (component (B)) is heated to adjust hot water. The temperature of the hot water is not particularly limited, and may be, for example, 40 ℃ or more or 80 ℃ or more, or 100 ℃ or less or 95 ℃ or less. Then, the dissolved product of the branched polyester resin (component (a)) and the nonionic surfactant having an aromatic ring (component (C)) is added to the hot water, and dispersed by stirring or the like as necessary. In this case, the above-mentioned optional components (for example, aromatic sulfonate) may be added as necessary. The water dispersion thus obtained is directly cooled to room temperature, for example, by leaving it cold, whereby the fiber treatment agent of the present invention can be produced.
[3. method of Using fiber-treating agent ]
The method of using the fiber treatment agent of the present invention is not particularly limited, and for example, a fiber product may be immersed in the fiber treatment agent of the present invention or its aqueous dilution and then dried. After impregnation, the fiber product may be pressed if necessary before drying, or may be heated during impregnation. The fiber product is processed in this way, and functions (for example, antistatic performance) can be appropriately imparted to the fiber product. The fiber product is not particularly limited, and examples thereof include woven fabrics, clothes, carpets, nonwoven fabrics, and the like. The type of the fibers is not particularly limited, and natural fibers or artificial fibers may be used, and examples thereof include polyester fibers and blended products of polyester fibers and other fibers. As described above, the fiber-treating agent of the present invention can be used as it is or as a water-dilutable liquid. In the case of a water-diluted solution, the fiber-treating agent of the present invention may be contained in an amount of, for example, 1 mass% or more, 2 mass% or more, or 3 mass% or more, or 20 mass% or less, 15 mass% or less, or 10 mass% or less, based on the water-diluted solution.
The use of the fiber treatment agent of the present invention is not particularly limited, and for example, the agent can be used as a durable antistatic agent for fibers, a water absorbing agent, and the like.
Examples
Next, an embodiment of the present invention will be described. However, the present invention is not limited to the following examples.
[ Synthesis examples 1 to 5]
As shown below, a polyester resin was synthesized (produced). The polyester resins of the following synthetic examples 2, 3, 4 and 5 are branched polyester resins obtained by copolymerizing the above-mentioned monomers (i) to (iii), and correspond to the component (a) of the fiber-treating agent of the present invention. On the other hand, the following synthetic example 1 is a linear polyester resin in which a polyol having 3 or more hydroxyl groups (monomer (iii)) is not copolymerized.
(Synthesis example 1)
60g of dimethyl terephthalate, 90g of ethylene glycol and 0.3g of zinc acetate as a catalyst were charged in a reaction vessel and subjected to transesterification reaction at 180 ℃ for 1 hour. In this case, methanol produced by the transesterification reaction was distilled off at around 140 ℃. After the transesterification, 240g of polyethylene glycol (Mw3,000) and 2.7g of ADK STAB AO-330 (trade name of ADEKA, Inc.) as an antioxidant were further added to the reaction vessel, and the temperature was again raised to 180 ℃ and then the pressure was reduced. Then, the temperature and pressure are increased and reduced to 240 to 250 ℃ at 10torr (about 1.3X 10)3Pa) or less for 3 hours, thereby obtaining the objective polyester resin. The weight average molecular weight (Mw) of the polyester resin was 25000.
(Synthesis example 2)
The same operation as in Synthesis example 1 was carried out, except that 238.4g of polyethylene glycol (Mw3,000) and 0.6g of pentaerythritol were used in place of 240g of polyethylene glycol (Mw3,000), to obtain the objective branched polyester resin. The weight average molecular weight (Mw) of the polyester resin was 25000.
(Synthesis example 3)
The same operation as in Synthesis example 1 was carried out, except that 238.7g of polyethylene glycol (Mw3,000) and 0.3g of glycerol were used in place of 240g of polyethylene glycol (Mw3,000), to obtain the objective branched polyester resin. The weight average molecular weight (Mw) of the polyester resin was 25000.
(Synthesis example 4)
The same operation as in Synthesis example 2 was carried out except that 50g of dimethyl terephthalate and 10g of dimethyl isophthalate were used in place of 60g of dimethyl terephthalate to obtain the objective branched polyester resin. The weight average molecular weight (Mw) of the polyester resin was 25000.
(Synthesis example 5)
The same operation as in Synthesis example 2 was carried out, and 0.6g of tartaric acid was added after the reaction to obtain the objective branched polyester resin. The weight average molecular weight (Mw) of the polyester resin was 25000.
[ examples and comparative examples ]
The fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3 were produced as follows.
(example 1)
3g of the polyester resin (component (A)) obtained in Synthesis example 2 and 3g of a 10 mol adduct of bisphenol A with EO (ethylene oxide) (component (C)) were mixed and dissolved at 100 to 120 ℃. This dissolved matter was added to 94g of hot water (component (B)) at 90 ℃ and then slowly cooled to room temperature, thereby obtaining a water dispersion (fiber treatment agent) of a polyester resin.
(example 2)
A water dispersion of a polyester resin (fiber treatment agent) was obtained in the same manner as in example 1, except that 3g of m-xylene sulfonic acid Na (aromatic sulfonate) was further added to the hot water.
(example 3)
A water dispersion of a polyester resin (fiber treatment agent) was obtained in the same manner as in example 1, except that an EO16 mol adduct of tristyrenated phenol was used as the component (C) instead of the EO10 mol adduct of bisphenol a.
(example 4)
A water dispersion (fiber treatment agent) of a polyester resin was obtained in the same manner as in example 2, except that the polyester resin obtained in synthesis example 3 was used as the component (a).
(example 5)
A water dispersion (fiber treatment agent) of a polyester resin was obtained in the same manner as in example 2, except that the polyester resin obtained in synthesis example 4 was used as the component (a).
(example 6)
A water dispersion (fiber treatment agent) of a polyester resin was obtained in the same manner as in example 2, except that the polyester resin obtained in Synthesis example 5 was used as the component (A), and that 0.5g of di-long alkyl (C12-C18) dimethylammonium chloride was used in place of Na metaxylene sulfonate (aromatic sulfonate).
Comparative example 1
A water dispersion (fiber treatment agent) of the polyester resin was obtained in the same manner as in example 1, except that 3g of the polyester resin obtained in synthesis example 1 was used instead of the polyester resin obtained in synthesis example 2.
Comparative example 2
A water dispersion of a polyester resin (fiber treatment agent) was obtained in the same manner as in example 1, except that the EO10 molar adduct of bisphenol a (component (C)) was not added.
Comparative example 3
A water dispersion of a polyester resin (fiber-treating agent) was obtained in the same manner as in example 1, except that 3g of a 10-mole adduct of lauryl alcohol EO was used in place of the 10-mole adduct of bisphenol A (component (C)).
[ Performance evaluation ]
The performance of the fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3 was evaluated (tested) by the following method.
[ dispersibility in Water ]
Aqueous dispersions (5 mass% aqueous dispersions) obtained by diluting the fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3 by 20 times (mass ratio) with water were filtered through 80-mesh filter cloth, and dispersibility was visually evaluated according to the presence or absence of residue. The evaluation criteria are as follows, and evaluation is performed with a circle, a triangle, or an x.
O: residue-free Δ: less residue x: much residue
[ method of processing fiber ]
Polyester spotted knitted fabric was used as a sample (fiber product). The fabric was immersed in an aqueous dispersion (5 mass% aqueous dispersion) prepared by diluting the fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3 by 20 times (mass ratio) with water. Thereafter, the above fabric was rolled at a rolling reduction of 70% using a rolling mill, and further, dried at 130 ℃ for 2 minutes using a tenter. As described above, the fabric (textile product) is processed by the fiber treatment agent.
[ washing test ]
The fabrics (fiber products) processed with the fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3 were subjected to a washing test using a washing machine and a detergent described below in accordance with JIS L0217103.
Washing machine: full-automatic washing machine
A detergent: non-phosphate TOP (trade name of lion king Co., Ltd.)
[ antistatic Property ]
Before (without) washing and after 5 times washing of the above-mentioned fabrics (fiber products) processed with each of the fiber treatment agents of examples 1 to 6 and comparative examples 1 to 3, antistatic properties were measured by a triboelectrification voltage test method and a half-life test method according to JIS L1094 electrification test method, respectively.
The performance of each of the fiber-treating agents of examples 1 to 6 and comparative examples 1 to 3 evaluated as above and the composition of each fiber-treating agent are shown in table 1 below.
[ TABLE 1 ]
As shown in Table 1, the fiber-treating agents of examples 1 to 6 all exhibited good dispersibility in water. Further, when the fabrics (textile products) were processed with the fiber treatment agents of examples 1 to 6, antistatic properties were imparted. Further, the fabrics treated with the fiber treatment agents of examples 1 to 6 did not lose their antistatic properties even after 5 washes. That is, it was confirmed that the fiber treatment agents of examples 1 to 6 function as durable antistatic agents having excellent washing durability.
On the other hand, the fiber treatment agents of comparative examples 1 to 3 were not good in dispersibility in water. Specifically, in comparative example 1 using the linear polyester resin of synthesis example 1, even when an adduct of bisphenol a with EO10 mol (a nonionic surfactant having an aromatic ring, component (C)) was used, dispersibility in water was not good. On the other hand, comparative examples 2 and 3 used the branched polyester resin of synthesis example 2, and no nonionic surfactant was added (comparative example 2), or instead of the EO10 mol adduct of bisphenol a, a EO10 mol adduct of lauryl alcohol (nonionic surfactant having no aromatic ring) was used (comparative example 3), and as a result, dispersibility in water was not good. Therefore, the fiber treatment agents of comparative examples 1 to 3 did not adhere to the fabric, and the antistatic performance and the washing durability could not be evaluated. In comparative examples 2 and 3, the same results were obtained even when the branched polyester resin of synthesis example 2 was replaced with the branched polyester resin of synthesis example 3.
Claims (11)
1. A fiber treatment agent characterized by comprising the following components (A) to (C),
the component (A) is a copolymer obtained by polymerizing at least the following monomers (i) to (iii);
(A) a branched polyester resin,
(B) Water,
(C) A nonionic surfactant having an aromatic ring,
(i) at least one of a divalent aromatic carboxylic acid and a derivative thereof,
(ii) the amount of the diol is such that,
(iii) a polyol having more than 3 hydroxyl groups,
the component (C) is selected from 1 or more than 2 of alkylene oxide addition products of bisphenol A, styrenated phenol, beta-naphthol and benzyl ether.
2. The fiber-treating agent according to claim 1, wherein the fiber-treating agent further comprises an aromatic sulfonate.
3. The fiber-treating agent according to claim 2, wherein the mass of the aromatic sulfonate is 50 mass% or more and 200 mass% or less with respect to the mass of the component (C).
4. The fiber-treating agent according to claim 1, wherein the fiber-treating agent further comprises a cationic surfactant.
5. The fiber-treating agent according to claim 1 or 2, wherein in the monomer (i), the divalent aromatic carboxylic acid is at least one of terephthalic acid and isophthalic acid.
6. The fiber treatment agent according to claim 1 or 2, wherein in the monomer (ii), the glycol is at least one of ethylene glycol and polyethylene glycol.
7. The fiber treatment agent according to claim 1 or 2, wherein the amount of the monomer (i) of the branched polyester resin (A) used is 5% by mass or more and 50% by mass or less of the entire copolymerization component,
the amount of the monomer (ii) used is 50 to 94 mass% based on the whole copolymerization component,
the amount of the monomer (iii) used is 0.05 to 1 mass% based on the whole copolymerization component.
8. The fiber treatment agent according to claim 1 or 2, wherein the content of water as the component (B) is 200 mass% or more and 2500 mass% or less with respect to the mass of all components other than water as the component (B).
9. The fiber treatment agent according to claim 1 or 2, wherein the content of the component (C) is 15% by mass or more and 80% by mass or less with respect to the mass of all components other than water as the component (B).
10. The fiber treatment agent according to claim 1 or 2, wherein the content of the component (C) is 30 to 300% by mass relative to the mass of the branched polyester resin as the component (A).
11. The fiber treatment agent according to claim 1 or 2, wherein the mass of the aromatic sulfonate is 10% by mass or more and 50% by mass or less with respect to the mass of all components other than water as the component (B).
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| JP2016207306 | 2016-10-21 | ||
| JP2016-207306 | 2016-10-21 | ||
| PCT/JP2017/037562 WO2018074477A1 (en) | 2016-10-21 | 2017-10-17 | Processing agent for fibers |
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| CN109863270B true CN109863270B (en) | 2021-11-19 |
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| JP (1) | JP7129910B2 (en) |
| CN (1) | CN109863270B (en) |
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| KR20210146958A (en) * | 2019-03-29 | 2021-12-06 | 가부시키가이샤 아데카 | Antistatic agent, antistatic agent composition comprising same, antistatic resin composition comprising them, and molded article thereof |
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| JP5675230B2 (en) * | 2010-09-03 | 2015-02-25 | 株式会社ダイセル | Thermosetting epoxy resin composition and use thereof |
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2017
- 2017-10-17 CN CN201780065354.6A patent/CN109863270B/en active Active
- 2017-10-17 WO PCT/JP2017/037562 patent/WO2018074477A1/en active Application Filing
- 2017-10-17 JP JP2018546360A patent/JP7129910B2/en active Active
- 2017-10-19 TW TW106135884A patent/TWI747971B/en active
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| US4027346A (en) * | 1974-08-21 | 1977-06-07 | Toyo Boseki Kabushiki Kaisha | Polyester fiber treated with anionic polyalkylene oxide emulsified polyester polyether finish |
| JPS62289674A (en) * | 1986-06-02 | 1987-12-16 | 帝人株式会社 | Hydrophilic treatment agent |
| WO1997000351A2 (en) * | 1995-06-19 | 1997-01-03 | E.I. Du Pont De Nemours And Company | Durable hydrophilic polymer coatings |
| CN102653589A (en) * | 2011-03-02 | 2012-09-05 | 上海诺科生物科技有限公司 | Water soluble or water dispersible polyester synthesized by utilizing waste polyester and application thereof in textile processing |
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| CN105440292A (en) * | 2014-09-15 | 2016-03-30 | 海洋化工研究院有限公司 | Design and preparation of branched type hydrophilic auxiliary agent |
| KR101611191B1 (en) * | 2015-03-18 | 2016-04-11 | 주식회사 한국발보린 | Composition of hydrophilic coating agent |
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| TW201823299A (en) | 2018-07-01 |
| TWI747971B (en) | 2021-12-01 |
| JPWO2018074477A1 (en) | 2019-08-08 |
| WO2018074477A1 (en) | 2018-04-26 |
| JP7129910B2 (en) | 2022-09-02 |
| CN109863270A (en) | 2019-06-07 |
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