WO2023224002A1 - Agent de traitement de fibres - Google Patents

Agent de traitement de fibres Download PDF

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Publication number
WO2023224002A1
WO2023224002A1 PCT/JP2023/018109 JP2023018109W WO2023224002A1 WO 2023224002 A1 WO2023224002 A1 WO 2023224002A1 JP 2023018109 W JP2023018109 W JP 2023018109W WO 2023224002 A1 WO2023224002 A1 WO 2023224002A1
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mass
group
treatment agent
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fiber treatment
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PCT/JP2023/018109
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English (en)
Japanese (ja)
Inventor
淳一 古川
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花王株式会社
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Publication of WO2023224002A1 publication Critical patent/WO2023224002A1/fr

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    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F4/00—Monocomponent artificial filaments or the like of proteins; Manufacture thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof

Definitions

  • the present invention relates to a fiber treatment agent for imparting water resistance, heat resistance, and thermal shape memory ability to naturally derived fibers, and preferably to naturally derived fibers used in textile products such as headdress products such as wigs and extensions. It relates to a fiber treatment agent.
  • naturally derived fibers generally have a natural texture and appearance that come from natural materials.
  • regenerated protein fibers such as regenerated collagen fibers, are obtained by solubilizing acid-soluble collagen or insoluble collagen with alkali or enzymes to make a spinning stock solution, and discharging it into a coagulation bath through a spinning nozzle to form fibers. It will be done.
  • Naturally derived fibers are generally more hydrophilic than synthetic fibers, so they have a high water absorption rate, and when they contain a lot of water, they generally have low mechanical strength.Regenerated protein fibers in particular have a high mechanical strength. is extremely low. Therefore, during washing, the mechanical strength is significantly reduced due to the high water absorption rate, and the material breaks during subsequent drying, leading to a decline in its suitability as a textile product.
  • regenerated protein fibers have the problem of low heat resistance.For example, when heat-setting using a hair iron etc. This causes shrinkage and curling, which impairs the appearance.
  • Patent Document 1 Japanese Patent Application Publication No. 2019-143281
  • the present invention provides a fiber treatment agent containing the following components (A) and (B).
  • the present invention improves the water resistance and heat resistance, which are problems with naturally derived fibers, and imparts thermal shape memory ability, as well as improves elasticity (tenacity) and surface feel.
  • This invention relates to a fiber treatment agent that does not cause coloring.
  • the present inventors have discovered that by treating naturally-derived fibers with a composition containing a compound that has a carboxy group and has a hydrogen bond term of Hansen's solubility parameter below a certain value, The carboxyl groups of the compounds that have penetrated into the fibers strongly coordinate with the metals (mainly polyvalent metals) in the naturally-derived fibers, thereby making the interior of the fibers hydrophobic and preventing the compounds from leaking out of the fibers. I found it.
  • naturally-derived fibers have improved water resistance and heat resistance in both dry and wet conditions, and are not only able to be shaped by heat-setting, but also surprisingly have improved elasticity (tenacity) of naturally-derived fibers.
  • the present invention has been completed based on the discovery that the hair's hair color is improved compared to before treatment and can be raised to a level close to that of human hair, and that no coloring occurs.
  • water resistance and heat resistance which are problems of naturally derived fibers, can be improved, thermal shape memory ability can be imparted, and elasticity (tenacity) and surface feel can be improved. It is possible to provide a fiber treatment agent that does not color naturally derived fibers.
  • the fibers to be treated with the fiber treatment agent of the present invention are preferably metal-containing fibers, preferably metal-containing naturally-derived fibers or metal-containing synthetic fibers, and in particular, naturally-derived fibers containing metals. preferable.
  • Naturally derived fibers are fibers collected from natural animals and plants, or polymers and oligomers such as proteins and polysaccharides derived from keratin, collagen, casein, soybeans, peanuts, corn, silk waste, silk proteins (such as silk fibroin), etc. Fibers that are artificially produced as raw materials.
  • fibers artificially produced using polymers and oligomers such as proteins and polysaccharides derived from keratin, collagen, casein, soybeans, peanuts, corn, silk waste, silk proteins (for example, silk fibroin), etc. are preferred.
  • Regenerated protein fibers made from proteins derived from , keratin, collagen, casein, soybean protein, peanut protein, corn protein, silk protein (for example, silk fibroin) are more preferable, and regenerated collagen fibers made from collagen and silk fibroin are more preferable.
  • Regenerated protein fibers such as regenerated silk fibers used as raw materials are more preferable, and regenerated collagen fibers are even more preferable.
  • Regenerated collagen fibers can be produced using known techniques, and the composition does not need to be 100% collagen, and may contain natural or synthetic polymers and additives for quality improvement. Furthermore, the regenerated collagen fibers may be post-processed. The preferred form of the regenerated collagen fibers is filaments. Filament is generally taken out from a bobbin wound or boxed state. Furthermore, the filaments that come out of the drying process can also be used directly in the process of producing regenerated collagen fibers.
  • the metal-containing synthetic fiber may be a metal-treated synthetic fiber.
  • Naturally derived fibers containing metals include those that originally contain metals, such as fibers collected from natural animals and plants.In this case, there is no need to add metals, but for example, if Fibers treated with metal salts may also be used, such as the fibers treated with aluminum salts for water resistance as described in Japanese Patent Publication No. 2003-027318.
  • Component (A) A compound having at least one carboxy group or a salt thereof and having no fused ring, the hydrogen bond term ⁇ H of Hansen's solubility parameter is 18.3 MPa 1/2 or less]
  • Component (A) is a compound having at least one carboxy group or a salt thereof and having no fused ring, the hydrogen bond term ⁇ H of Hansen's solubility parameter being 18.3 MPa 1/2 or less.
  • the hydrogen bond term of the Hansen solubility parameters is defined as ⁇ H (MPa 1/2 ) (energy term due to intermolecular hydrogen bonds) calculated in °C.
  • examples of the case where component (A) is a salt include alkali metal salts such as sodium salt and potassium salt.
  • Examples of the compound of component (A) include the following (A1) and (A2).
  • (A1) An aromatic compound having at least one carboxy group or a salt thereof and having no fused ring, the hydrogen bond term ⁇ H of Hansen's solubility parameter being 18.3 MPa 1/2 or less
  • (A2) A compound having at least one carboxy group or a salt thereof and having no fused ring (aromatic compound except for)
  • aromatic compound of component (A1) examples include compounds represented by the following general formula (1) or general formula (2), or salts thereof.
  • R 1 represents a hydrogen atom, a hydroxyl group, or an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an aralkyloxy group that may have a substituent.
  • R 2 represents an o-phenylene group, m-phenylene group, p-phenylene group, benzylidene group, or an alkylene group which may have a substituent.
  • R 1 is an aryl group, an aryloxy group or an aralkyloxy group.
  • a 1 to A 5 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a straight or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group. show. ]
  • examples of the aromatic compound represented by general formula (1) include compounds represented by general formula (1A), (1B), or (1C) shown below.
  • B 1 to B 4 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group.
  • R 3 represents a hydroxy group or a group represented by the following general formula (1A)-a or (1A)-b.
  • B 5 to B 9 have the same meanings as B 1 to B 4 above, R 4 represents a hydrogen atom or a methyl group, and n represents an integer of 0 to 2. ]
  • D 1 to D 4 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a straight or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group.
  • E 1 to E 5 each independently represent a group similar to D 1 to D 4 or a group represented by general formula (1B)-a.
  • m represents an integer of 0 to 4.
  • R 6 represents a hydrogen atom or a group represented by the general formula (1C)-a
  • G 1 and G 2 each independently have a hydrogen atom, an acetyl group, a halogen atom, or a substituent.
  • R 6 is a hydrogen atom
  • at least one of G 1 and G 2 is an aryl group which may have a substituent, an aralkyl group having 7 to 12 carbon atoms, an arylalkenyl group or an aroyloxy group.
  • J 1 to J 5 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group. show. ]
  • compounds in which R 3 is a hydroxy group include 2-carboxybenzoic acid (phthalic acid) (Hansen's solubility parameter hydrogen bond term ⁇ H: 13.4 MPa 1/2 ) (Hereinafter, the numerical value in parentheses after each compound name indicates the hydrogen bond term ⁇ H calculated by the above-mentioned method).
  • compounds in which R 3 is a group represented by the general formula (1A)-a include 2-(((4-vinylbenzyl)oxy)carbonyl)benzoic acid (7.0MPa 1/2 ).
  • compounds in which R 3 is a group represented by the general formula (1A)-b include 2-((2-(acryloyloxy)ethoxy)carbonyl)benzoic acid (9.1 MPa 1/2 ), 2-((2-(methacryloyloxy)ethoxy)carbonyl)benzoic acid (8.4 MPa 1/2 ).
  • Compounds represented by general formula (1B) include 2-benzoylbenzoic acid (7.5 MPa 1/2 ), 2-(2-methylbenzoyl)benzoic acid (6.9 MPa 1/2 ), 2-(3-methyl Benzoyl)benzoic acid (6.6MPa 1/2 ), 2-(4-methylbenzoyl)benzoic acid (7.2MPa 1/2 ), 2-(2-chlorobenzoyl)benzoic acid (7.1MPa 1/2 ), 2- (3-chlorobenzoyl)benzoic acid (6.9MPa 1/2 ), 2-(4-chlorobenzoyl)benzoic acid (7.5MPa 1/2 ), 2-(4-(2-(2-(acryloyloxy)ethoxy) )ethoxy)benzoyl)benzoic acid (8.7MPa 1/2 ).
  • examples of compounds where R 6 is a hydrogen atom include phenylsuccinic acid (15.8MPa 1/2 ), 2,3-diphenylsuccinic acid (11.9MPa 1/2 ), (+)-Di-p-toluoyl-D-tartaric acid (10.2 MPa 1/2 ) is mentioned.
  • compounds in which R 6 is a group represented by general formula (1C)-a include 4-oxo-4-((4-vinylbenzyl)oxy)butane Examples include acids (10.1MPa 1/2 ).
  • aromatic compounds represented by general formula (2) include benzoic acid (9.5MPa 1/2 ), 2-methylbenzoic acid (8.4MPa 1/2 ), and 3- Methylbenzoic acid (8.0MPa 1/2 ), 4-methylbenzoic acid (8.8MPa 1/2 ), 2-ethylbenzoic acid (7.7MPa 1/2 ), 3-ethylbenzoic acid (7.4MPa 1/2 ), 4-Ethylbenzoic acid (8.1MPa 1/2 ), 2-propylbenzoic acid (7.0MPa 1/2 ), 3-propylbenzoic acid (6.7MPa 1/2 ), 4-propylbenzoic acid (7.4MPa 1/2) ), 2-isopropylbenzoic acid (6.7MPa 1/2 ), 3-isopropylbenzoic acid (6.5MPa 1/2 ), 4-isopropylbenzoic acid (7.1MPa 1/2 ), 2-n-butylbenzoic acid (6.8 MPa 1/2 ), 3-n-butylbenzoic acid (6.5MPa 1/2 ), 4-isopropylbenz
  • Examples of the compound of component (A2) include potassium 2,4-hexadienoate (12.5 MPa 1/2 ).
  • the hydrogen bond term ⁇ H of the aromatic compound of component (A1) is preferably 16.0 MPa 1/2 or less, more preferably 13.5 MPa 1/2 or less, and even more preferably 12.0 from the viewpoint of appropriately hydrophobicizing the inside of the fiber.
  • MPa 1/2 or less more preferably 10.0MPa 1/2 or less, preferably 3.0MPa 1/2 or more, more preferably 4.0MPa 1/2 or more, still more preferably 5.0MPa 1/2 or more .
  • the hydrogen bond term ⁇ H of the compound of component (A2) is preferably 16.0 MPa 1/2 or less, more preferably 15.0 MPa 1/2 or less, still more preferably 14.0 MPa 1 from the viewpoint of making the inside of the fiber appropriately hydrophobic. /2 or less, more preferably 13.0 MPa 1/2 or less, preferably 11.0 MPa 1/2 or more, more preferably 11.5 MPa 1/2 or more, still more preferably 12.0 MPa 1/2 or more.
  • component (A) refers to the content of the corresponding acid form when component (A) is a salt.
  • the content of component (A) varies depending on the pH range of the fiber treatment agent, but is preferably in the range shown below.
  • component (A) especially component (A1), benzoic acid or its salt (hereinafter sometimes referred to as “component (A1-1)"
  • the pH of the fiber treatment agent is 2.0 or more and less than 6.5.
  • the components in the fiber treatment agent ( The content of A1-1) is preferably 0.8% by mass or more, more preferably 3.0% by mass or more, even more preferably 5.0% by mass or more, even more preferably 10% by mass or more, and even more preferably 10% by mass or more, as benzoic acid (acid form).
  • it is 15% by mass or more, even more preferably 20% by mass or more, and from the viewpoint of improving the feel of the fiber surface, it is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass. It is not more than 50% by weight, even more preferably not more than 40% by weight, even more preferably not more than 35% by weight.
  • component (A) is (A1-1) benzoic acid or its salt, and the pH of the fiber treatment agent is 2.0 or more and less than 6.5
  • the component (A1-1) in the fiber treatment agent of the present invention is From the above viewpoint, the content is preferably 0.8 to 90% by mass, more preferably 3.0 to 80% by mass, even more preferably 5.0 to 70% by mass, and even more preferably 10 to 50% by mass, as benzoic acid (acid form). %, even more preferably 15 to 40% by weight, even more preferably 20 to 35% by weight.
  • component (A) is (A1-1) benzoic acid or its salt
  • the pH of the fiber treatment agent is 6.5 or more and 11.0 or less
  • the naturally derived fibers after treatment will have higher shape retention and water resistance.
  • the content of component (A1-1) in the fiber treatment agent is as benzoic acid (acid form).
  • the component (A1-1) in the fiber treatment agent of the present invention is from the above viewpoint, the content is preferably 0.8 to 90% by mass, more preferably 3.0 to 80% by mass, even more preferably 5.0 to 70% by mass, and even more preferably 10 to 70% by mass as benzoic acid (acid form). %, even more preferably 15-50% by weight, even more preferably 20-50% by weight, even more preferably 25-45% by weight, even more preferably 26-45% by weight, even more preferably 28-40% by weight. %, even more preferably 30 to 40% by weight.
  • components (A1) other than benzoic acid or its salts are those whose pH of the fiber treatment agent is 2.0 or more and less than 6.5.
  • the components in the fiber treatment agent (A1-2) is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, even more preferably 1.0% by mass or more, and it also improves the feel of the fiber surface. From the viewpoint of improvement, the content is preferably 70% by mass or less, more preferably 60% by mass or less, still more preferably 50% by mass or less, and even more preferably 45% by mass or less.
  • component (A) is a component (A1) other than (A1-2) benzoic acid or its salt, and the pH of the fiber treatment agent is 2.0 or more and less than 6.5, it is a component in the fiber treatment agent of the present invention.
  • the content of (A1-2) is preferably 0.1 to 70% by mass, more preferably 0.2 to 60% by mass, even more preferably 0.5 to 50% by mass, and even more preferably 1.0 to 45% by mass. be.
  • component (A) is a component (A1) other than (A1-2) benzoic acid or its salt, and the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, the natural fiber after treatment will have a higher shape.
  • the content of component (A1-2) in the fiber treatment agent is preferably The content is 1.0% by mass or more, more preferably 2.0% by mass or more, even more preferably 5.0% by mass or more, even more preferably 10% by mass or more, and from the viewpoint of improving the feel of the fiber surface, preferably 70% by mass or less. , more preferably 60% by mass or less, still more preferably 50% by mass or less, even more preferably 40% by mass or less.
  • component (A) is a component (A1) other than (A1-2) benzoic acid or its salt, and the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, it is a component in the fiber treatment agent of the present invention.
  • the content of (A1-2) is preferably 1.0 to 70% by mass, more preferably 2.0 to 60% by mass, even more preferably 5.0 to 50% by mass, and even more preferably 10 to 40% by mass. be.
  • component (A) is component (A2) and the pH of the fiber treatment agent is 2.0 or more and less than 6.5, the naturally-derived fibers after treatment will have higher shape retention, water resistance, elasticity (tenacity, i.e. From the viewpoint of imparting high elongation at break (when the fiber is stretched) and heat resistance, the content of component (A2) in the fiber treatment agent is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and even more preferably It is 0.5% by mass or more, even more preferably 1.0% by mass or more, and from the viewpoint of improving the feel of the fiber surface, preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less. , and even more preferably 30% by mass or less.
  • component (A) is component (A2) and the pH of the fiber treatment agent is 2.0 or more and less than 6.5
  • the content of component (A2) in the fiber treatment agent of the present invention is, from the above point of view, Preferably 0.1 to 60% by weight, more preferably 0.2 to 50% by weight, even more preferably 0.5 to 40% by weight, and even more preferably 1.0 to 30% by weight.
  • component (A) is component (A2) and the pH of the fiber treatment agent is 6.5 or higher and 11.0 or lower, the naturally derived fibers after treatment will have higher shape retention, water resistance, elasticity (tenacity, i.e. From the viewpoint of imparting high elongation at break (when the fiber is stretched) and heat resistance, the content of component (A2) in the fiber treatment agent is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, even more preferably The content is 5.0% by mass or more, even more preferably 10% by mass or more, and from the viewpoint of improving the feel of the fiber surface, preferably 70% by mass or less, more preferably 60% by mass or less, and still more preferably 50% by mass or less. , and even more preferably 40% by mass or less.
  • component (A) is component (A2) and the pH of the fiber treatment agent is 6.5 or more and 11.0 or less
  • the content of component (A2) in the fiber treatment agent of the present invention is, from the above point of view, Preferably 1.0 to 70% by weight, more preferably 2.0 to 60% by weight, even more preferably 5.0 to 50% by weight, and even more preferably 10 to 40% by weight.
  • the agent contains two or more kinds of compounds as component (A).
  • the fiber treatment agent contains two or more compounds as component (A)
  • at least one of them is preferably an aromatic compound represented by general formula (2), more preferably benzoic acid or a salt thereof. .
  • component (A) contains an aromatic compound represented by general formula (2)
  • the content of the compound is the highest among component (A), and benzoic acid or a salt thereof is included. In this case, it is more preferable that the content of the compound in component (A) is the highest.
  • the fiber treatment agent contains two or more compounds as component (A)
  • the content in the fiber treatment agent improves the overall solubility of component (A), lowers the turbidity of the fiber treatment agent, and enables uniform treatment of fibers, thereby improving the texture of the fiber surface after treatment. From the viewpoint of improving the is 5.0% by mass or less.
  • the content of A) in the fiber treatment agent improves the overall solubility of component (A), lowers the turbidity of the fiber treatment agent, and enables uniform treatment of the fibers, thereby improving the fiber surface after treatment.
  • the content is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, even more preferably 2.0% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, More preferably, it is 10% by mass or less.
  • the mass ratio of the remaining component (A) after removal is calculated as follows:
  • A) Preferably 0.01 or more, more preferably 0.01 or more, from the viewpoint of improving the overall solubility and lowering the turbidity of the fiber treatment agent, making it possible to treat the fibers uniformly, and thereby improving the feel of the fiber surface after treatment. is 0.05 or more, more preferably 0.10 or more, and is preferably 1.0 or less, more preferably 0.5 or less, and still more preferably 0.25 or less.
  • the fiber treatment agent of the present invention uses water as a medium.
  • the content of component (B) in the fiber treatment agent of the present invention is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, and even more preferably 40% by mass or more. , and preferably 99% by mass or less, more preferably 95% by mass or less, still more preferably 90% by mass or less, even more preferably 85% by mass or less. That is, the content of component (B) in the fiber treatment agent of the present invention is preferably 10 to 99% by mass, more preferably 20 to 95% by mass, even more preferably 30 to 90% by mass, even more preferably 40% by mass. ⁇ 85% by mass.
  • the fiber treatment agent of the present invention may contain a cationic surfactant within a range that does not impair the effects of the present invention.
  • the cationic surfactant is preferably a mono-long chain alkyl quaternary ammonium salt having one alkyl group having 8 to 24 carbon atoms and three alkyl groups having 1 to 4 carbon atoms.
  • the at least one mono-long chain alkyl quaternary ammonium surfactant is selected from compounds represented by the following general formula (3).
  • R 7 is a saturated or unsaturated linear or branched alkyl group having 8 to 22 carbon atoms, R 11 -CO-NH-(CH 2 ) m - or R 11 -CO-O-(CH 2 ) m - (R 11 represents a saturated or unsaturated linear or branched alkyl chain having 7 to 21 carbon atoms, p represents an integer of 1 to 4), R 8 , R 9 and R 10 independently represents an alkyl group having 1 to 4 carbon atoms or a hydroxylalkyl group having 1 to 4 carbon atoms, and An - represents a chloride ion, bromide ion, methosulfate ion or ethosulfate ion. ]
  • Suitable cationic surfactants include, for example, long chain quaternary ammonium compounds such as cetyltrimethylammonium chloride, myristyltrimethylammonium chloride, behentrimonium chloride, cetyltrimethylammonium bromide, stearamidopropyltrimonium chloride, These can be used alone or as a mixture.
  • the content of the cationic surfactant in the fiber treatment agent of the present invention is preferably 0.05% by mass or more, from the viewpoint of improving the surface feel of the naturally-derived fibers after treatment and further improving the effects of the present invention. It is more preferably 0.10% by mass or more, more preferably 10% by mass or less, and more preferably 5.0% by mass or less.
  • the fiber treatment agent of the present invention can contain silicone from the viewpoint of improving the surface feel of the naturally-derived fibers after treatment and improving the cohesion.
  • the silicone is preferably one or more selected from dimethylpolysiloxane and amino-modified silicone.
  • any cyclic or acyclic dimethylpolysiloxane polymer can be used, examples of which include the SH200 series, BY22-019, BY22-020, BY11-026, B22-029, BY22-034, BY22. -050A, BY22-055, BY22-060, BY22-083, FZ-4188 (all from Toray Dow Corning Co., Ltd.), KF-9088, KM-900 series, MK-15H, MK-88 (all from Shin-Etsu Chemical) Kogyo Co., Ltd.).
  • any silicone having an amino group or an ammonium group can be used.
  • examples include amino-modified silicone oil in which all or some of the terminal hydroxyl groups are end-capped with a methyl group, etc. Amodimethicone, which has not been stopped, is mentioned. From the viewpoint of improving the surface feel of the treated naturally-derived fibers and improving their cohesion, examples of preferred amino-modified silicones include compounds represented by the following formula.
  • R' represents a hydrogen atom, a hydroxyl group, or R x
  • R x represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms
  • J represents R x
  • R"-(NHCH 2 CH 2 ) a represents NH 2
  • OR represents a number of 10 or more and less than 20,000, preferably 20 or more and less than 3,000, more preferably 30 or more and less than 1,000, and even more preferably 40 or more and less than 800.
  • suitable commercially available amino-modified silicones include SF8452C, SS3551 (all from Dow Corning Toray Co., Ltd.), KF-8004, KF-867S, and KF-8015 (all from Shin-Etsu Chemical Co., Ltd.).
  • Examples include amino-modified silicone oil, and amodimethicone emulsions such as SM8704C, SM8904, BY22-079, FZ-4671, and FZ4672 (all manufactured by Dow Corning Toray Co., Ltd.).
  • the content of silicone in the fiber treatment agent of the present invention is preferably 0.1% by mass or more, more preferably 0.2% by mass, from the viewpoint of improving the surface feel of the naturally-derived fibers after treatment and further improving the effects of the present invention.
  • the content is at least 0.5% by mass, more preferably at least 0.5% by mass, and is preferably at most 20% by mass, more preferably at most 10% by mass, even more preferably at most 5.0% by mass.
  • the fiber treatment agent of the present invention may contain a cationic polymer from the viewpoint of improving the surface feel of the naturally-derived fibers after treatment.
  • a cationic polymer refers to a polymer having a cationic group or a group that can be ionized into a cationic group, and also includes an amphoteric polymer that is cationic as a whole. That is, aqueous solutions containing an amino group or an ammonium group in the side chain of the polymer chain, or a diallyl quaternary ammonium salt as a constituent unit, such as cationized cellulose derivatives, cationic starches, cationized guar gum derivatives, diallyl quaternary Examples include polymers or copolymers of ammonium salts, quaternized polyvinylpyrrolidone derivatives, and the like.
  • diallyl quaternary ammonium One or more selected from polymers containing salts as constitutional units, quaternized polyvinylpyrrolidone derivatives, and cationized cellulose derivatives are preferred, and selected from polymers or copolymers of diallyl quaternary ammonium salts and cationized cellulose derivatives. More preferably, one or more of these are used.
  • Suitable polymers or copolymers of diallyl quaternary ammonium salts include dimethyldiallyl ammonium chloride polymers (polyquaternium-6, e.g. Marquat 100; Lubrizol Advanced Materials), dimethyl diallyl ammonium chloride/ Acrylic acid copolymers (Polyquaternium-22, e.g. Marquat 280, 295; Lubrizol Advanced Materials), dimethyldiallylammonium chloride/acrylamide copolymers (Polyquaternium-7, e.g. Marquat 550; Lubrizol Advanced Materials) Materials Co., Ltd.) etc.
  • polyquaternium-6 e.g. Marquat 100; Lubrizol Advanced Materials
  • dimethyl diallyl ammonium chloride/ Acrylic acid copolymers Polyquaternium-22, e.g. Marquat 280, 295; Lubrizol Advanced Materials
  • dimethyldiallylammonium chloride/acrylamide copolymers Polyquaternium-7, e.g. Marquat
  • suitable quaternized polyvinylpyrrolidone derivatives include polymers obtained by polymerizing vinylpyrrolidone copolymers and dimethylaminoethyl methacrylate (polyquaternium 11, such as Gaffcut 734, Gaffcut 755, and Gaffcut 755N (all manufactured by Ashland)). ).
  • suitable cationized cellulose include polymers in which hydroxycellulose is loaded with glycidyltrimethylammonium chloride (polyquaternium 10, such as Leogard G, Polyquaternium GP (Lion Corporation), Polymer JR-125, Polymer JR-400, Polyquaternium 10) JR-30M, LR-400, LR-30M (Amarkol), hydroxyethyl cellulose dimethyl diallylammonium chloride (polyquaternium-4, e.g. Cellcoat H-100, L-200 (Amarkol)) ) etc.
  • polyquaternium 10 such as Leogard G, Polyquaternium GP (Lion Corporation), Polymer JR-125, Polymer JR-400, Polyquaternium 10) JR-30M, LR-400, LR-30M (Amarkol), hydroxyethyl cellulose dimethyl diallylammonium chloride (polyquaternium-4, e.g. Cellcoat H-100, L-200 (Amar
  • the content of the cationic polymer in the fiber treatment agent of the present invention is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, still more preferably The content is 0.05% by mass or more, preferably 20% by mass or less, and more preferably 10% by mass or less.
  • the fiber treatment agent of the present invention can contain an antioxidant such as ascorbic acid; a pH adjuster such as sodium hydroxide, potassium hydroxide, phosphoric acid, or hydrochloric acid.
  • an antioxidant such as ascorbic acid
  • a pH adjuster such as sodium hydroxide, potassium hydroxide, phosphoric acid, or hydrochloric acid.
  • the pH of the fiber treatment agent of the present invention is preferably 2.0 or more, more preferably 3.0 or more, still more preferably 3.5 or more, and even more preferably 4.0 or more, from the viewpoint of suppressing damage to naturally-derived fibers and improving durability. Further, it is preferably 11.0 or less, more preferably 10.0 or less, and even more preferably 9.0 or less.
  • the pH in the present invention is a value at 25°C. That is, the pH of the fiber treatment agent of the present invention is preferably 2.0 to 11.0, more preferably 3.0 to 10.0, still more preferably 3.5 to 9.0, and even more preferably It is between 4.0 and 9.0.
  • the storage temperature may be set to a cold or high temperature, or the voids in the storage container may be filled with nitrogen.
  • the storage temperature of the fiber treatment agent is preferably 1°C or higher, more preferably 2°C or higher, and even more preferably 5°C or higher, from the viewpoint of preventing freezing or recrystallization. From the viewpoint of preventing undesirable reaction progress, the temperature is preferably 25°C or lower, more preferably 20°C or lower, and even more preferably 15°C or lower.
  • the storage temperature of the fiber treatment agent is preferably 20°C or higher, more preferably 30°C or higher, and even more preferably 40°C or higher, from the viewpoint of preventing recrystallization of a highly concentrated solution, and prevents oxidative coloring and unintended reactions. From the viewpoint of preventing progression, the temperature is preferably 80°C or lower, more preferably 70°C or lower, and still more preferably 60°C or lower.
  • the naturally-derived fibers immersed in the fiber treatment agent may be dry or wet.
  • the amount of the fiber treatment agent in which the naturally-derived fibers are soaked is the bath ratio (mass of the fiber treatment agent/mass of the naturally-derived fibers) to the mass of the naturally-derived fibers, preferably 2 or more, more preferably 3 or more, and even more preferably is 5 or more, even more preferably 10 or more, even more preferably 20 or more, and is preferably 500 or less, more preferably 250 or less, and even more preferably 100 or less. That is, the bath ratio is preferably 2 to 500, more preferably 3 to 250, even more preferably 5 to 100, even more preferably 10 to 100, and even more preferably 20 to 100.
  • the naturally-derived fibers may be fixed in advance with a curler or the like, and then immersed in the fiber treatment agent of the present invention under heating. By doing so, it is possible to simultaneously impart a desired shape to the naturally-derived fiber in addition to thermal shape memory ability and high durability.
  • the immersion of the naturally-derived fibers in the fiber treatment agent in step (i) is preferably performed under heating, and this heating is performed by heating the fiber treatment agent. Note that this heating may be performed by immersing the naturally-derived fibers in a heated fiber treatment agent, but it may also be performed by immersing the naturally-derived fibers in a low-temperature fiber treatment agent and then heating.
  • the temperature of the fiber treatment agent is preferably 20°C or higher, more preferably 20°C or higher, in order to obtain the effects of the present invention by increasing the interaction between component (A) and fiber constituent molecules in naturally derived fibers, such as protein molecules.
  • the temperature is 35°C or higher, more preferably 45°C or higher, and preferably lower than 100°C, more preferably 80°C or lower, and even more preferably 70°C or lower in order to prevent natural fibers from being denatured and deteriorated by heat. , more preferably 60°C or lower.
  • the immersion time in step (i) is appropriately adjusted depending on the heating temperature, but for example, from the viewpoint of exerting the effect of improving elasticity on naturally-derived fibers, it is preferably 15 minutes or more, more preferably 30 minutes or more, and even more preferably
  • the heating time is 1 hour or more, and in order to prevent damage to the naturally-derived fibers, the heating time is preferably 48 hours or less, more preferably 24 hours or less, and even more preferably 12 hours or less.
  • step (i) is performed in an environment where evaporation of water is suppressed.
  • a specific method for suppressing moisture evaporation includes a method of covering the container of the fiber treatment agent in which the naturally-derived fibers are immersed with a film-like substance, cap, lid, etc. made of a material that does not permeate water vapor.
  • the naturally-derived fibers may or may not be rinsed, but rinsing is preferred from the viewpoint of preventing deterioration of the surface feel of the naturally-derived fibers due to excess component (A).
  • component (A) causes component (A) to penetrate into the naturally-derived fibers and strongly coordinate with metals, such as polyvalent metals, within the fibers, thereby producing various effects.
  • step (i) In addition to the above-mentioned step (i), one or more steps selected from decolorization, dyeing, surface finishing to impart hydrophobicity/lower friction, and heat treatment to further improve fiber elasticity (tenacity) You may perform each process in addition.
  • the decolorization and dyeing treatments may be performed before or after the above-mentioned step (i).
  • step (i) surface finishing to impart hydrophobicity and lower friction, and heat treatment to further improve fiber elasticity (tenacity), need to be carried out after the above-mentioned step (i).
  • the processing order is not particularly limited. Furthermore, either the surface finishing for imparting hydrophobicity and low friction or the heat treatment for further improving fiber elasticity (tenacity) may be performed first.
  • Decolorization is performed by immersing the naturally-derived fibers in a decolorizing agent composition containing an alkaline agent, an oxidizing agent, and water.
  • the decolorizing agent composition is usually of a two-part type, the first part containing an alkaline agent and water, and the second part containing an oxidizing agent and water.
  • the two agents are usually stored separately and mixed before soaking the natural fibers.
  • Suitable alkaline agents include, for example, ammonia and its salts; alkanolamines (monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol, etc.) and their salts; alkanediamines (1,3 -propanediamine, etc.) and salts thereof; and carbonates (guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc.); and mixtures thereof.
  • alkanolamines monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol, etc.
  • alkanediamines (1,3 -propanediamine, etc.
  • carbonates guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc.
  • the content of the alkaline agent in the decolorizing agent composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass. % or more, and preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 7.5% by mass or less.
  • Suitable oxidizing agents include, but are not limited to, for example, hydrogen peroxide, urea peroxide, melamine peroxide, and sodium bromate. Among these oxidizing agents, hydrogen peroxide is preferred.
  • the content of the oxidizing agent in the decolorizing agent composition is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 15% by mass or less, more preferably 12% by mass or less, and even more preferably It is 9% by mass or less.
  • the pH of the second agent at 25°C is preferably 2.0 or higher, more preferably 2.5 or higher, and preferably 6.0 or lower, more preferably 4.0 or lower. be. This pH can be adjusted with suitable buffers.
  • the pH of the decolorizer composition at 25°C is preferably 6 or higher, more preferably 6.5 or higher, even more preferably 6.8 or higher, and preferably 11.0 or lower, more preferably 10.5 or lower, and still more preferably 10.0 or lower. .
  • Dyeing is performed by immersing the naturally-derived fibers in a dye composition.
  • the dye composition contains a dye and may optionally contain an alkaline agent, an acid, an oxidizing agent, and the like.
  • Dyes include direct dyes, oxidative dyes, and combinations thereof.
  • direct dye is not particularly limited, and any direct dye suitable for dyeing can be used.
  • direct dyes include anionic dyes, nitro dyes, disperse dyes, cationic dyes, and dyes with an azophenol structure selected from the group consisting of HC Red 18, HC Blue 18 and HC Yellow 16 below; Mention may be made of salts, as well as mixtures thereof.
  • cationic dyes include Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 41, Basic Blue 99, Basic Brown 4, Basic Brown 16, Basic Brown 17, Natural Brown 7, and Basic Green 1.
  • Basic Orange 31, Basic Red 2, Basic Red 12, Basic Red 22, Basic Red 51, Basic Red 76, Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 10, Basic Violet 14, Basic Yellow 57 and Basic Examples include, but are not limited to, Yellow 87 and mixtures thereof. Particularly preferred are Basic Red 51, Basic Orange 31, Basic Yellow 87 and mixtures thereof.
  • anionic dyes include Acid Black 1, Acid Blue 1, Acid Blue 3, Food Blue 5, Acid Blue 7, Acid Blue 9, Acid Blue 74, Acid Orange 3, Acid Orange 4, Acid Orange 6, Acid Orange 7. , Acid Orange 10, Acid Red 1, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 33, Acid Red 50, Acid Red 52, Acid Red 73, Acid Red 87, Acid Red 88, Acid Red 92, Acid Red 155, Acid Red 180, Acid Violet 2, Acid Violet 9, Acid Violet 43, Acid Violet 49, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 3, Food Yellow No. 8, D&C Brown No.
  • Hood Black 1 D&C Green No.5, D&C Green No.8, D&C Orange No.4, D&C Orange No.10, D&C Orange No.11, D&C Red No.21, D&C Red No.27, D&C Red No.33, D&C Violet 2, D&C Yellow No.7, D&C Yellow No.8, D&C Yellow No.10, FD&C Red 2, FD&C Red 40, FD&C Red No.4, FD&C Yellow No.6, FD&C Blue 1, Hood Black 1, Hood Examples include, but are not limited to, Black 2, and their alkali metal salts (sodium salts, potassium salts, etc.) and mixtures thereof.
  • preferred anionic dyes are Acid Black 1, Acid Red 52, Acid Violet 2, Acid Violet 43, Acid Red 33, Acid Orange 4, Acid Orange 7, Acid Red 27, Acid Yellow 3, Acid Yellow 10, and these. It's salt. More preferred anionic dyes are Acid Red 52, Acid Violet 2, Acid Red 33, Acid Orange 4 and Acid Yellow 10 and salts and mixtures thereof.
  • nitro dyes examples include HC Blue No.2, HC Blue No.4, HC Blue No.5, HC Blue No.6, HC Blue No.7, HC Blue No.8, HC Blue No.9, HC Blue No.10, HC Blue No.11, HC Blue No.12, HC Blue No.13, HC Brown No.1, HC Brown No.2, HC Green No.1, HC Orange No.1, HC Orange No.
  • disperse dyes include, but are not limited to, Disperse Blue 1, Disperse Black 9, Disperse Violet 1, and mixtures thereof.
  • direct dyes can be used alone or in combination of two or more, and direct dyes with different ionic properties can also be used in combination.
  • the content of the direct dye in the dye composition is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and even more preferably 0.05% by mass or more, from the viewpoint of obtaining sufficient dyeability. From the viewpoint of performance, the content is preferably 10% by mass or less, more preferably 7.5% by mass or less, even more preferably 5.0% by mass or less, and still more preferably 3.0% by mass or less.
  • the dye composition contains only a direct dye as a dye, an oxidizing agent is not required to dye naturally derived fibers, but if you want to brighten the color of naturally derived fibers, an oxidizing agent may be included in the composition. You can also do it.
  • the dye composition contains an oxidation dye
  • it is usually of a two-part type, with the first part containing an oxidation dye intermediate (precursor and coupler) and an alkaline agent, and the second part containing an oxidizing agent such as hydrogen peroxide.
  • the two agents are usually stored separately and mixed before soaking the natural fibers.
  • the oxidation dye intermediate is not particularly limited, and any known precursors and couplers commonly used in dyed products can be suitably used.
  • precursors include paraphenylenediamine, toluene-2,5-diamine, 2-chloro-paraphenylenediamine, N-methoxyethyl-paraphenylenediamine, N-phenylparaphenylenediamine, N,N-bis(2- hydroxyethyl)-paraphenylenediamine, 2-(2-hydroxyethyl)-paraphenylenediamine, 2,6-dimethyl-paraphenylenediamine, 4,4'-diaminodiphenylamine, 1,3-bis(N-(2- Hydroxyethyl)-N-(4-aminophenyl)amino)-2-propanol, PEG-3,3,2'-paraphenylenediamine, paraaminophenol, paramethylaminophenol, 3-methyl-4-aminophenol, 2 -aminomethyl-4-aminophenol, 2-(2-hydroxyethylaminomethyl)-4-aminophenol, orthoamin
  • couplers include metaphenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4-(2-hydroxyethylamino)anisole, 2,4-diamino-5-methylphenetol, 2,4-diamino- 5-(2-hydroxyethoxy)toluene, 2,4-dimethoxy-1,3-diaminobenzene, 2,6-bis(2-hydroxyethylamino)toluene, 2,4-diamino-5-fluorotoluene, 1, 3-bis(2,4-diaminophenoxy)propane, meta-aminophenol, 2-methyl-5-aminophenol, 2-methyl-5-(2-hydroxyethylamino)phenol, 2,4-dichloro-3-amino Phenol, 2-chloro-3-amino-6-methylphenol, 2-methyl-4-chloro-5-aminophenol, N-cyclopentyl-meta-aminophenol,
  • the content of precursor and coupler in the dye composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and preferably 10% by mass or less, more preferably 7.5% by mass or less, More preferably, it is 5.0% by mass or less.
  • the dye composition contains an oxidative dye, it further contains an alkaline agent.
  • alkaline agents include, for example, ammonia and its salts; alkanolamines (monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol, etc.) and their salts; alkanediamines (1,3 -propanediamine, etc.) and salts thereof; and carbonates (guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc.); and mixtures thereof.
  • the content of the alkaline agent in the dye composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1.0% by mass or more, and preferably 15% by mass or less, more preferably It is 10% by mass or less, more preferably 7.5% by mass or less.
  • the composition containing the oxidizing agent (second part) is stored separately from the composition containing the oxidation dye (first part), and mixed before dipping the natural fibers.
  • Suitable oxidizing agents include, but are not limited to, for example, hydrogen peroxide, urea peroxide, melamine peroxide, and sodium bromate. Among these oxidizing agents, hydrogen peroxide is preferred.
  • the content of the oxidizing agent in the dye composition is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 15% by mass or less, more preferably 12% by mass or less, and even more preferably It is 9% by mass or less.
  • the pH of the second agent at 25°C is preferably 2 or more, more preferably 2.5 or more, and preferably 6 or less, more preferably 4 or less. It is. This pH can be adjusted with suitable buffers.
  • the pH at 25°C of the stain composition formed by mixing the first agent and the second agent is preferably 6 or more, more preferably 6.5 or more, even more preferably 6.8 or more, and preferably 11 or less, more preferably It is preferably 10.5 or less, more preferably 10 or less.
  • the dye composition contains an oxidative dye, it may further contain the direct dyes exemplified above.
  • the dye composition can preferably further contain a surfactant, a conditioning component, etc. shown below, and can suitably take the form of a solution, emulsion, cream, paste, and mousse.
  • the temperature of the dye composition is preferably 0°C or higher, more preferably 10°C or higher, and even more preferably The temperature is 20°C or higher, preferably 90°C or lower, and more preferably 80°C or lower.
  • the fiber stretching rate during heating is preferably 0.1% or more, more preferably 0.2% or more, and even more preferably 0.5% or more, from the viewpoint of more effectively improving the elasticity of the fibers, and also preventing damage to the fibers. From the viewpoint of suppression, it is preferably 10% or less, more preferably 5.0% or less, even more preferably 2.0% or less.
  • the heating temperature is preferably 120°C or higher, more preferably 140°C or higher, and even more preferably 160°C or higher, from the viewpoint of more effectively improving the elasticity of the fibers, and from the viewpoint of suppressing damage to the fibers. , preferably 240°C or lower, more preferably 220°C or lower, even more preferably 200°C or lower.
  • the heating time is preferably 1 second or more, more preferably 3 seconds or more, even more preferably 5 seconds or more, from the viewpoint of more effectively improving the elasticity of the fibers, and from the viewpoint of suppressing damage to the fibers. , preferably 60 seconds or less, more preferably 30 seconds or less, even more preferably 20 seconds or less.
  • the naturally-derived fibers can be left standing in water while being stretched under tension.
  • the stretching ratio at this time is preferably 0.1% or more, more preferably 0.2% or more, and still more preferably 0.5% or more, from the viewpoint of more effectively improving the elasticity of the fibers, and also suppressing damage to the fibers. From this viewpoint, it is preferably 10% or less, more preferably 5.0% or less, and even more preferably 2.0% or less.
  • the water temperature is preferably 5°C or higher, more preferably 20°C or higher, and even more preferably 30°C or higher, from the viewpoint of more effectively improving the elasticity of the fibers, and from the viewpoint of suppressing damage to the fibers.
  • the temperature is preferably 80°C or lower, more preferably 60°C or lower, even more preferably 50°C or lower.
  • the standing time in water is preferably 1 minute or more, more preferably 5 minutes or more, and even more preferably 30 minutes or more, from the viewpoint of more effectively improving the elasticity of the fibers, and from the viewpoint of improving the elasticity of the fibers.
  • the time period is preferably 48 hours or less, more preferably 24 hours or less, and still more preferably 3 hours or less.
  • step (i) it is possible to reach a level of stretchability comparable to that of human hair when drying the fiber.
  • the texture of the fibers that have undergone the various treatments described above can be improved by subsequent post-treatment of the fibers, such as treatment with a fiber treatment agent such as a fabric softener, or treatment with a hair care agent such as a conditioner or hair treatment. .
  • a fiber treatment agent such as a fabric softener
  • a hair care agent such as a conditioner or hair treatment.
  • the fiber processing method By treating naturally derived fibers with the above fiber processing method, it is possible to add shape by heat setting by containing component (A) in the fibers, and improve water resistance, heat resistance, and tensile modulus. It is possible to produce fibers with highly improved elasticity (tenacity) of naturally derived fibers, preferably fibers for headdress products, etc., and the fibers can also be used to produce various textile products, preferably headdresses. Products, etc. can be manufactured.
  • suitable headdress products in the present invention include, for example, hair wigs, wigs, weaving, hair extensions, braided hair, hair accessories, doll hair, and the like.
  • a fiber treatment agent containing the following components (A) and (B).
  • component (A) is one or more compounds selected from the group consisting of components (A1) and (A2) below.
  • A1 An aromatic compound having at least one carboxy group or a salt thereof and having no fused ring, the hydrogen bond term ⁇ H of Hansen's solubility parameter being 18.3 MPa 1/2 or less
  • A2 A compound having at least one carboxy group or a salt thereof and having no fused ring (aromatic compound except for)
  • component (A1) is a compound represented by the following general formula (1) or general formula (2) or a salt thereof, or phenylbutanoic acid.
  • R 1 represents a hydrogen atom, a hydroxyl group, or an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an aralkyloxy group that may have a substituent.
  • R 2 represents an o-phenylene group, m-phenylene group, p-phenylene group, benzylidene group, or an alkylene group which may have a substituent.
  • R 1 is an aryl group, an aryloxy group or an aralkyloxy group.
  • a 1 to A 5 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a straight or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group. show. ]
  • the compound represented by general formula (1) is a compound represented by general formula (1A), (1B) or (1C) shown below, 3-carboxybenzoic acid (isophthalic acid), 4-carboxybenzoic acid ( The fiber treatment agent according to ⁇ 3>, which is terephthalic acid), 3-benzoylbenzoic acid, or 4-benzoylbenzoic acid.
  • B 1 to B 4 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group.
  • R 3 represents a hydroxy group or a group represented by the following general formula (1A)-a or (1A)-b.
  • B 5 to B 9 have the same meanings as B 1 to B 4 above, R 4 represents a hydrogen atom or a methyl group, and n represents an integer of 0 to 2. ]
  • D 1 to D 4 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a straight or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group.
  • E 1 to E 5 each independently represent a group similar to D 1 to D 4 or a group represented by general formula (1B)-a.
  • m represents an integer of 0 to 4.
  • R 6 represents a hydrogen atom or a group represented by the general formula (1C)-a
  • G 1 and G 2 each independently have a hydrogen atom, an acetyl group, a halogen atom, or a substituent.
  • R 6 is a hydrogen atom
  • at least one of G 1 and G 2 is an aryl group which may have a substituent, an aralkyl group having 7 to 12 carbon atoms, an arylalkenyl group or an aroyloxy group.
  • J 1 to J 5 each independently represent a hydrogen atom, an acetyl group, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms, an alkenyl group, an alkoxy group, or an alkenyloxy group. show. ]
  • the compound represented by general formula (1A) is preferably 2-carboxybenzoic acid (phthalic acid), 2-(((4-vinylbenzyl)oxy)carbonyl)benzoic acid, 2-((2-(acryloyloxy) ) ethoxy)carbonyl)benzoic acid or 2-((2-(methacryloyloxy)ethoxy)carbonyl)benzoic acid, the fiber treatment agent according to ⁇ 4>.
  • the compound represented by general formula (1B) is preferably 2-benzoylbenzoic acid, 2-(2-methylbenzoyl)benzoic acid, 2-(3-methylbenzoyl)benzoic acid, 2-(4-methylbenzoyl) Benzoic acid, 2-(2-chlorobenzoyl)benzoic acid, 2-(3-chlorobenzoyl)benzoic acid, 2-(4-chlorobenzoyl)benzoic acid, or 2-(4-(2-(2-(acryloyl)
  • the fiber treatment agent according to ⁇ 4> which is oxy)ethoxy)ethoxy)benzoyl)benzoic acid.
  • the compound represented by general formula (1C) is preferably phenylsuccinic acid, 2,3-diphenylsuccinic acid, (+)-di-p-toluoyl-D-tartaric acid, or 4-oxo-4-((4 -
  • the compound represented by general formula (2) is benzoic acid, 2-methylbenzoic acid, 3-methylbenzoic acid, 4-methylbenzoic acid, 2-ethylbenzoic acid, 3-ethylbenzoic acid, 4-ethylbenzoic acid.
  • the hydrogen bond term ⁇ H of the aromatic compound of component (A1) is preferably 16.0 MPa 1/2 or less, more preferably 13.5 MPa 1/2 or less, even more preferably 12.0 MPa 1/2 or less, even more preferably 10.0 MPa 1 /2 or less, and preferably 3.0MPa 1/2 or more, more preferably 4.0MPa 1/2 or more, even more preferably 5.0MPa 1/2 or more, any one of ⁇ 2> to ⁇ 8> Fiber treatment agent as described in section.
  • component (A2) is potassium 2,4-hexadienoate.
  • the hydrogen bond term ⁇ H of the compound of component (A2) is preferably 16.0 MPa 1/2 or less, more preferably 15.0 MPa 1/2 or less, even more preferably 14.0 MPa 1/2 or less, even more preferably 13.0 MPa 1/2
  • the fiber treatment agent according to ⁇ 2> or ⁇ 10> which is the following, and preferably 11.0 MPa 1/2 or more, more preferably 11.5 MPa 1/2 or more, even more preferably 12.0 MPa 1/2 or more .
  • component (B) is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, and preferably 99% by mass or less. , more preferably 95% by mass or less, still more preferably 90% by mass or less, even more preferably 85% by mass or less, the fiber treatment agent according to any one of ⁇ 1> to ⁇ 11>.
  • the pH at 25°C is preferably 2.0 or higher, more preferably 3.0 or higher, even more preferably 3.5 or higher, even more preferably 4.0 or higher, and preferably 11.0 or lower, more preferably 10.0 or lower, and even more preferably 9.0 or lower.
  • component (A) contains (A1-1) benzoic acid or a salt thereof.
  • the pH of the fiber treatment agent is 2.0 or more and less than 6.5, and the content of component (A1-1) in the fiber treatment agent is preferably 0.8% by mass or more, more preferably 3.0% as benzoic acid (acid type). % by mass or more, more preferably 5.0% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, and preferably 90% by mass or less,
  • the content according to ⁇ 14> is more preferably 80% by mass or less, still more preferably 70% by mass or less, even more preferably 50% by mass or less, still more preferably 40% by mass or less, and even more preferably 35% by mass or less. Fiber treatment agent.
  • the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, and the content of component (A1-1) in the fiber treatment agent is preferably 0.8% by mass or more, more preferably 3.0% as benzoic acid (acid type). mass% or more, more preferably 5.0 mass% or more, even more preferably 10 mass% or more, even more preferably 15 mass% or more, even more preferably 20 mass% or more, even more preferably 25 mass% or more, and even more Preferably 26% by mass or more, even more preferably 28% by mass or more, even more preferably 30% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass.
  • the fiber treatment agent according to ⁇ 14> which is still more preferably 50% by mass or less, even more preferably 45% by mass or less, even more preferably 40% by mass or less.
  • component (A) contains a component (A1) other than (A1-2) benzoic acid or a salt thereof.
  • the pH of the fiber treatment agent is 2.0 or more and less than 6.5, and the content of component (A1-2) in the fiber treatment agent is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and even more preferably 0.5%. It is at least 70% by mass, more preferably at most 60% by mass, even more preferably at most 50% by mass, and even more preferably at most 45% by mass. , the fiber treatment agent according to ⁇ 17>.
  • the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, and the content of component (A1-2) in the fiber treatment agent is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, and even more preferably 5.0% by mass. It is at least 70% by mass, more preferably at most 60% by mass, even more preferably at most 50% by mass, and even more preferably at most 40% by mass. , the fiber treatment agent according to ⁇ 17>.
  • component (A) contains component (A2).
  • the pH of the fiber treatment agent is 2.0 or more and less than 6.5, and the content of component (A2) in the fiber treatment agent is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and even more preferably 0.5% by mass. Above, still more preferably 1.0% by mass or more, preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less, even more preferably 30% by mass or less, ⁇
  • the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, and the content of component (A2) in the fiber treatment agent is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, and even more preferably 5.0% by mass. Above, still more preferably 10% by mass or more, preferably 70% by mass or less, more preferably 60% by mass or less, still more preferably 50% by mass or less, even more preferably 40% by mass or less, ⁇
  • the content of the aromatic compound represented by general formula (2) is the highest among component (A), and more preferably, the content of benzoic acid or its salt is the highest among component (A).
  • the pH of the fiber treatment agent is 2.0 or more and less than 6.5, and the content of the component (A) remaining after excluding the compound with the highest concentration among all components (A) in the fiber treatment agent is preferably 0.1% by mass or more. , more preferably 0.5% by mass or more, still more preferably 1.0% by mass or more, and preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5.0% by mass or less, ⁇ 23> ⁇
  • the pH of the fiber treatment agent is 6.5 or more and 11.0 or less, and the content of the component (A) remaining after removing the compound with the highest concentration among all the components (A) in the fiber treatment agent is preferably 0.5% by mass or more. , more preferably 1.0% by mass or more, still more preferably 2.0% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 10% by mass or less, ⁇ 23> ⁇
  • the mass ratio of the remaining component (A) excluding the compound in question to the compound having the highest concentration among all components (A) in the fiber treatment agent is preferably 0.01 or more, more preferably 0.05 or more, even more preferably 0.10 or more, and preferably 1.0 or less, more preferably 0.5 or less,
  • a fiber processing method comprising the following step (i). Step (i) Step (A) of immersing the naturally-derived fiber in a composition containing the following components (A) and (B): the hydrogen bond term ⁇ H of Hansen's solubility parameter is 18.3 MPa 1/2 or less, Compound having at least one carboxyl group or a salt thereof and no fused ring (B): Water
  • a fiber processing method comprising the following step (i). Step (i) Step of immersing naturally derived fibers in a composition containing the following components (A1-2) and (B) (A1-2): Hydrogen bond term ⁇ H of Hansen's solubility parameter is 18.3 MPa 1/2 Compounds having at least one carboxy group or a salt thereof and having no fused ring (excluding benzoic acid and its salts), which are the following: (B):Water
  • composition containing the following components (A) and (B) as a fiber treatment agent.
  • A) A compound having at least one carboxy group or its salt and having no fused ring, with a hydrogen bond term ⁇ H of Hansen's solubility parameter of 18.3 MPa 1/2 or less
  • composition containing the following components (A1-2) and (B) as a fiber treatment agent.
  • A1-2 Compounds with at least one carboxy group or its salt and no condensed rings (with the exception of benzoic acid and (excluding salt)
  • B Water
  • Regenerated collagen fibers (*) 0.50g of hair strands with a length of 22cm are soaked in a container containing a fiber treatment agent in an amount that corresponds to the bath ratio shown in the table. It was immersed in a water bath (manufacturer: Toyo Seisakusho Co., Ltd./model number: TBS221FA) at the temperature shown and heated for the time shown in the table.
  • * Regenerated collagen fibers manufactured by Kaneka were purchased in the form of commercially available extension products, and the fibers were cut and divided into hair bundles for evaluation. For this evaluation, we used extension products that are labeled as using 100% Ultima as the fiber type, are white with a color count of 30, and are straight in shape. 2.
  • the container containing the hair tresses was removed from the water bath and allowed to come to room temperature. 3. Remove the hair strands from the container, rinse with running tap water at 30°C for 30 seconds, lather with evaluation shampoo for 60 seconds, rinse with running tap water at 30°C for 30 seconds, lightly dry with a towel, and remove the hair strands. was dried while combing with a hot air dryer (Tescom, Nobby White NB3000).
  • the fiber piece was set in "MTT690 Automatic Fiber Tensile Testing Machine" manufactured by DIA-STRON limited. Automatic measurement was started after the fibers were left immersed in water for 30 minutes, and the average elongation at break was determined while the fibers were immersed in water. The higher the numerical value, the higher the elasticity, the higher the tenacity, and the higher the durability.
  • the average breaking elongation (A%) of the hair bundle after the treatment is based on the average breaking elongation (A%) when the fiber is pulled as it is (untreated; Comparative Example 1) cut from a commercially available product (untreated; Comparative Example 1), and the average breaking elongation (B %) increased from the untreated state (C%) is described in the table as "increase rate [%] of average elongation at break during fiber tension.”
  • C (%) B (%) - A (%)
  • the average breaking load during fiber tension was used as an index of water resistance.
  • the evaluation was performed using hair bundles immediately after being treated by the above ⁇ treatment method>. Further, as the numerical value, the average value when evaluating multiple fibers (10 fibers) was used. The evaluation was performed according to the following procedure. 1. Ten fibers were cut from the root of the hair bundle. A 3 cm piece of fiber was collected from around the middle between the root and tip of each fiber, yielding a total of 10 pieces of 3 cm hair. 2. The fiber piece was set in "MTT690 Automatic Fiber Tensile Testing Machine" manufactured by DIA-STRON limited. Automatic measurement was started after leaving the fiber immersed in water for 30 minutes, and the breaking load when the fiber was stretched while immersed in water was determined.
  • the average breaking load (W 0 (gf)) of the hair bundle after the treatment is based on the average breaking load (W 0 (gf)) when the fiber is pulled in the as-is state (untreated; Comparative Example 1) cut from the commercially available product (untreated; Comparative Example 1).
  • the extent to which W 1 (gf)) increased from the untreated state (Y (gf)) is shown in the table as "increase in average breaking load during fiber tension [gf]".
  • Y (gf) W 1 (gf) - W 0 (gf)
  • ⁇ Shrinkage rate when setting with high temperature iron> The shrinkage rate when set with a high temperature iron was used as an index of heat resistance.
  • the evaluation was performed using hair bundles immediately after being treated by the above ⁇ treatment method>. Further, as the numerical value, the average value when evaluating a plurality of fibers (5 fibers) was used. The evaluation was performed according to the following procedure. 1. ⁇ Treatment method> Five fibers were cut from the root of the hair bundle immediately after treatment and marked. After these treatments, the lengths of the five fibers were measured, and the average value was recorded (defining the length L1 ).
  • the five treated fibers with these markings are bundled together between two separately prepared untreated regenerated collagen fiber bundles of 0.5 g (1 g in total) to form a new hair bundle (hereinafter referred to as a large hair bundle).
  • a flat iron manufactured by Miki Electric Industrial Co., Ltd./model number: AHI-938, set at 180°C was applied three times at a speed of 5 cm/sec to the entire large hair bundle. 2. After the ironing operation, take out the 5 marked treated fibers from the large hair bundle, measure the length of each of the 5 marked treated fibers, and record the average value (take the length L 2 ). did. 3.
  • the shrinkage rate when heated with hot water was used as an index of water resistance and heat resistance.
  • the evaluation was performed using hair bundles immediately after being treated by the above ⁇ treatment method>. Further, as the numerical value, the average value when evaluating a plurality of fibers (5 fibers) was used. The evaluation was performed according to the following procedure. 1. Cut 5 fibers from the root of the hair bundle, record the average length of each fiber (length L 1 ), and then soak in a 90°C water bath (manufacturer: Toyo Seisakusho Co., Ltd. / model number: TBS221FA) ) and heated for 1 minute. 2.
  • Thermal shape memory ability was evaluated using hair bundles immediately after being treated by the above ⁇ treatment method>.
  • Value of the result of "I: Shape imparting (curl)" was 5% or less, it was considered that there was no effect, and subsequent processing and evaluation were not performed.
  • a 22 cm long hair bundle containing 0.5 g of regenerated collagen fibers was wetted with tap water at 30°C for 30 seconds, and then the wet hair bundle was wrapped around a plastic rod with a diameter of 14 mm and fixed with a clip. 2.
  • the hair bundle wrapped around the rod was immersed in a 60°C water bath (manufacturer: Toyo Seisakusho Co., Ltd./model number: TBS221FA) and heated for 1 minute. 3.
  • the hair tresses were taken out of the water bath, immersed in water at 25°C for 1 minute, taken out of the water, and allowed to return to room temperature. 4.
  • the hair bundle was removed from the rod, passed through the comb three times, and 3 minutes after being removed from the water, a photo was taken from the side while it was hanging.
  • ⁇ II Reshaping (straight) 1.
  • the hair bundle evaluated in I was passed through a comb to remove tangles, and then slid 6 times at a speed of 5 cm/sec with a flat iron (manufactured by Miki Electric Industrial Co., Ltd./model number: AHI-938) set at 180°C. 2.
  • a flat iron manufactured by Miki Electric Industrial Co., Ltd./model number: AHI-938
  • ⁇ III Reshaping (curl) 1.
  • the hair bundle evaluated in II was wetted with tap water at 30°C for 30 seconds, and then the wet hair bundle was wrapped around a plastic rod with a diameter of 14 mm and fixed with a clip.
  • the hair bundle wrapped around the rod was immersed in a 60°C water bath (manufacturer: Toyo Seisakusho Co., Ltd./model number: TBS221FA) and heated for 1 minute.
  • the hair tresses were taken out of the water bath, immersed in water at 25°C for 1 minute, taken out of the water, and allowed to return to room temperature. 4.
  • the hair bundle was removed from the rod, passed through the comb three times, and 3 minutes after being removed from the water, a photo was taken from the side while it was hanging.
  • the color was measured near the root, near the middle, and near the tip using a colorimeter (Konica Minolta Colorimeter CR-400), and the average value of a total of 6 points was taken as the colorimetric value ( L, a, b). 2.
  • the degree of coloring was evaluated by ⁇ E*ab using an untreated hair bundle of color count 30 white (*) (Comparative Example 1) as a standard.
  • the color was measured on the same day that the treatment was performed.
  • ⁇ E*ab is when the measured values of the untreated hair bundle with color count 30 white are (L 0 , a 0 , b 0 ) and the measured values of the treated hair bundle are (L 1 , a 1 , b 1 ) , [(L 1 -L 0 ) 2 + (a 1 -a 0 ) 2 +(b 1 -b 0 ) 2 ] 1/2 , and the coloring suppressing effect was judged according to the following criteria. 5: ⁇ E*ab ⁇ 5.0 4:5.0 ⁇ ⁇ E*ab ⁇ 10.0 3: 10.0 ⁇ ⁇ E*ab ⁇ 15.0 2: 15.0 ⁇ ⁇ E*ab ⁇ 20.0 1:20.0 ⁇ E*ab

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne un agent de traitement de fibres qui améliore la résistance à l'eau et la résistance à la chaleur, qui constituent des points problématiques dans des fibres d'origine naturelle, confère une mémoire de forme thermique, améliore l'élasticité (ténacité) et la sensation de surface, et colore des fibres d'origine naturelle.　Cet agent de traitement de fibres contient les composants (A) et (B) suivants.　(A) : Un composé ayant au moins un groupe carboxyle ou un sel de celui-ci et aucun cycle condensé, dans lequel la valeur de liaison hydrogène δH du paramètre de solubilité de Hansen est inférieure ou égale à 18,3 MPa1/2 (B) : de l'eau.
PCT/JP2023/018109 2022-05-18 2023-05-15 Agent de traitement de fibres WO2023224002A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2525035B2 (ja) * 1988-05-13 1996-08-14 株式会社クラレ 合成繊維布帛の処理方法
JP2009526897A (ja) * 2006-02-16 2009-07-23 ジョン グリエム、 難燃性化学組成物
WO2016158702A1 (fr) * 2015-03-30 2016-10-06 株式会社カネカ Fibres de protéines artificielles pour cheveux, leur procédé de fabrication, ainsi qu'articles d'ornement pour la tête les contenant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2525035B2 (ja) * 1988-05-13 1996-08-14 株式会社クラレ 合成繊維布帛の処理方法
JP2009526897A (ja) * 2006-02-16 2009-07-23 ジョン グリエム、 難燃性化学組成物
WO2016158702A1 (fr) * 2015-03-30 2016-10-06 株式会社カネカ Fibres de protéines artificielles pour cheveux, leur procédé de fabrication, ainsi qu'articles d'ornement pour la tête les contenant

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