WO2022138678A1 - 繊維処理剤 - Google Patents

繊維処理剤 Download PDF

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Publication number
WO2022138678A1
WO2022138678A1 PCT/JP2021/047435 JP2021047435W WO2022138678A1 WO 2022138678 A1 WO2022138678 A1 WO 2022138678A1 JP 2021047435 W JP2021047435 W JP 2021047435W WO 2022138678 A1 WO2022138678 A1 WO 2022138678A1
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Prior art keywords
fiber
less
mass
group
component
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English (en)
French (fr)
Japanese (ja)
Inventor
淳一 古川
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Kao Corp
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Kao Corp
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Priority to EP21910818.0A priority Critical patent/EP4268651A4/en
Priority to US18/259,113 priority patent/US20240068156A1/en
Priority to CN202180087270.9A priority patent/CN116648538A/zh
Publication of WO2022138678A1 publication Critical patent/WO2022138678A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • D06M13/322—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 nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41G—ARTIFICIAL FLOWERS; WIGS; MASKS; FEATHERS
    • A41G3/00—Wigs
    • A41G3/0083—Filaments for making wigs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
    • C07K1/1136—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure by reversible modification of the secondary, tertiary or quarternary structure, e.g. using denaturating or stabilising agents
    • D—TEXTILES; PAPER
    • D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
    • D02J—FINISHING OR DRESSING OF FILAMENTS, YARNS, THREADS, CORDS, ROPES OR THE LIKE
    • D02J13/00—Heating or cooling the yarn, thread, cord, rope, or the like, not specific to any one of the processes provided for in this subclass
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B3/00—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating
    • D06B3/02—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fibres, slivers or rovings
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/01—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof
    • D06M11/05—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof with water, e.g. steam; with heavy water
    • 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
    • D06M13/12—Aldehydes; Ketones
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups
    • D06M15/652—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups comprising amino groups
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/10—Animal fibres
    • D06M2101/14—Collagen fibres
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2211/00—Protein-based fibres, e.g. animal fibres
    • D10B2211/20—Protein-derived artificial fibres
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2401/00—Physical properties
    • D10B2401/06—Load-responsive characteristics
    • D10B2401/063—Load-responsive characteristics high strength
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2503/00—Domestic or personal
    • D10B2503/08—Wigs

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 used in headdress products such as wigs and extensions.
  • Naturally-derived fibers include wigs, extensions, and other headdress products as an example of their use, and unlike synthetic fibers, they have a natural texture and appearance that come from natural materials.
  • regenerated protein fibers for example, regenerated collagen fibers, are obtained by solubilizing acid-soluble collagen or insoluble collagen with an alkali or an enzyme to obtain a spinning stock solution, which is then discharged into a coagulation bath through a spinning nozzle to be fiberized. Is done.
  • regenerated collagen fibers generally have a higher water absorption rate because they are more hydrophilic than synthetic fibers, and their mechanical strength is extremely low when they contain a large amount of water. For this reason, the mechanical strength is significantly reduced due to the high water absorption rate during shampooing, and the product is broken when dried by a hair dryer thereafter, leading to a decrease in suitability as a hair ornament product.
  • the regenerated collagen fiber also has a problem of low heat resistance, and when set at a high temperature similar to human hair in a set using a curling iron, shrinkage and crimping occur and the appearance is impaired. It ends up.
  • the shape at the time of heat setting with a hair iron or the like continues to be memorized even after the subsequent hair washing (has thermal shape memorization ability), whereas with regenerated collagen fiber, at the time of heat setting with a hair iron or the like. Since the shape is lost in the subsequent hair washing (there is no thermal shape memory ability), there is a part that is inferior in terms of styling freedom as compared with the conventional plastic synthetic fiber.
  • Patent Document 3 a method of allowing a compound having a methylol group to act on human hair fibers that originally do not have thermal shape memory ability in order to newly impart thermal shape memory ability.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 40-9062
  • Patent Document 2 Japanese Patent Application Laid-Open No. 41-15258
  • Patent Document 3 Japanese Patent Application Laid-Open No. 2019-143282
  • the present invention contains a condensate produced from the following components (A) and (B), and a component (C) derived from the component (A) and a component derived from the component (B).
  • the present invention provides a fiber treatment agent having a total amount of more than 1% by mass and a turbidity of 1000 NTU or less.
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • the present invention contains the above-mentioned components (A) to (C), and the total content of the components derived from the component (A) and the components derived from the component (B) is 1% by mass or more. It provides a method for producing a fiber treatment agent, which heats an object until the turbidity becomes 1000 NTU or less.
  • the present invention provides a fiber treatment method including the following step (i). (i) A step of immersing the fiber in the fiber treatment agent and treating the fiber while maintaining the turbidity of the treatment agent at 1000 NTU or less.
  • the present invention provides a method for producing a fiber for a headdress product, which comprises a step of treating the fiber by the above-mentioned fiber treatment method.
  • the present invention provides a method for manufacturing a headdress product, which comprises a step of treating the fiber by the fiber treatment method.
  • the present invention provides a fiber for a headdress product containing a condensate produced from the above components (A) and (B).
  • the present invention provides a headdress product whose constituent element is a fiber containing a condensate produced from the above components (A) and (B).
  • the fibers may be strongly stretched, and the techniques described in Patent Documents 1 to 3 may not have sufficient elasticity (toughness) of the treated fibers. Therefore, in order to prevent breakage during elongation, there has been a demand for increasing the elasticity of the fiber after treatment.
  • the present invention produces a fiber for headdress products, which has improved water resistance and heat resistance of naturally-derived fibers typified by regenerated collagen fiber, is imparted with thermal shape memory ability, and is also excellent in elasticity (tenacity).
  • the present inventor changes the composition in which the fiber is immersed through three stages. That is, in Phase 1, formaldehyde and the melamine derivative are present in a free reaction with each other, and the composition is in a state of high turbidity. In Phase 2, the composition becomes transparent by reacting formaldehyde with the melamine derivative to form a water-soluble condensate. In Phase 3, the water-soluble condensates are further linked to form a water-insoluble condensate, and the turbidity of the composition increases again.
  • the present inventors used a composition containing a condensate of formaldehyde and a specific triazine derivative as a treatment agent with a turbidity of 1000 or less.
  • a composition containing a condensate of formaldehyde and a specific triazine derivative as a treatment agent with a turbidity of 1000 or less.
  • Cited Documents 1 to 3 crosslink the structure, so that the treated structure becomes brittle.
  • naturally-derived fibers are treated under the above conditions. It is surprising that the results showed that the elasticity (tenacity) of the target was improved compared to that before the treatment.
  • a fiber treatment agent for producing fibers for headdress products having improved water resistance and heat resistance of naturally derived fibers, imparted thermal shape memory ability, and improved elasticity (tenacity). Can be provided.
  • the fiber to be treated by the fiber treatment agent of the present invention may be either a synthetic fiber or a naturally derived fiber, but a naturally derived fiber is preferable.
  • Naturally-derived fibers are fibers collected from natural animals and plants, or artificially manufactured from keratin, collagen, casein, soybeans, peanuts, corn, silk chips, silk fibroin, etc., and are used to manufacture headdress products. Refers to the fiber used for. Of these, fibers collected from natural animals and plants other than human hair fibers, or fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk scraps, silk fibroin, etc. are preferable. Regenerated protein fibers such as regenerated collagen fibers made from the above and regenerated silk fibers made from silk fibroin are more preferable, and regenerated collagen fibers are even more preferable.
  • the regenerated collagen fiber can be produced by a known technique, and the composition does not have to be 100% collagen, and may contain natural or synthetic polymers or additives for quality improvement. Further, it may be a post-processed regenerated collagen fiber. Filaments are preferred as the morphology of the regenerated collagen fibers. Filaments are generally removed from bobbin-wound or boxed conditions. Further, the filament produced from the drying step in the manufacturing process of the regenerated collagen fiber can be directly used.
  • the fiber treatment agent of the present invention contains formaldehyde of the component (A) or a hydrate thereof and a condensate of the triazine derivative represented by the general formula (1) of the component (B).
  • this condensate also contains a water-insoluble condensate formed by further linking the water-soluble condensates to each other as long as the turbidity of the fiber treatment agent is 1000 NTU or less.
  • the term "condensate" includes both water-soluble and water-insoluble substances.
  • unreacted components (A) and components (B) may remain in addition to these condensates as long as the turbidity is 1000 NTU or less.
  • formaldehyde hydrate examples include formaldehyde monohydrate (methanediol). Of these, formaldehyde is preferable from the viewpoint of imparting high shape durability and durability to the naturally derived fiber after treatment.
  • the content of the component derived from the component (A) in the fiber treatment agent of the present invention is preferably 0.1% by mass or more, more preferably from the viewpoint of imparting high shape durability and strength to the naturally-derived fiber after treatment.
  • the content of the component derived from the component (A) in the fiber treatment agent of the present invention is preferable from the viewpoint of imparting high shape durability and strength to the naturally-derived fiber after treatment and from the viewpoint of formulation compatibility.
  • the "component derived from the component (A)” means the total content of the component derived from the component (A) and the remaining component (A) in the condensate. do.
  • the triazine derivative used in the present invention is represented by the following general formula (1).
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • Examples of the triazine derivative represented by the general formula (1) include melamine, monomethylol melamine, dimethylol melamine, trimethylol melamine, benzoguanamine, acetoguanamine, 2,4-diamino-1,3,5-triazine, ammerin, 2 -Chloro-4,6-diamino-1,3,5-triazine, etc., melamine, monomethylol melamine, dimethylol melamine from the viewpoint of imparting high shape durability and durability to naturally derived fibers after treatment. And at least one selected from trimethylol melamine, more preferably melamine.
  • the component (B) can be used alone or in combination of two or more.
  • the content of the component derived from the component (B) in the fiber treatment agent of the present invention is preferably 0.1% by mass or more, more preferably from the viewpoint of imparting high shape durability and strength to the naturally-derived fiber after treatment. Is 1% by mass or more, more preferably 2.5% by mass or more, still more preferably 5% by mass or more, and in addition to the above viewpoints, from the viewpoint of improving the feel of the fiber surface, preferably 60% by mass or less. It is more preferably 50% by mass or less, further preferably 40% by mass or less, still more preferably 35% by mass or less, and even more preferably 30% by mass or less.
  • the content of the component derived from the component (B) in the fiber treatment agent of the present invention is from the viewpoint of imparting high shape durability and strength to the treated fiber and improving the feel of the fiber surface. It is preferably 0.1 to 60% by mass, more preferably 1 to 50% by mass, still more preferably 2.5 to 40% by mass, still more preferably 5 to 35% by mass, and even more preferably 5 to 30% by mass.
  • the "component derived from the component (B)” means the total content of the component derived from the component (B) and the remaining component (B) in the condensate. do.
  • the total content of the component derived from the component (A) and the component derived from the component (B) in the fiber treatment agent of the present invention imparts higher shape durability and strength to the naturally-derived fiber after the treatment. From the viewpoint, it is more than 1% by mass, preferably 2.5% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and preferably from the viewpoint of improving the feel of the fiber surface. It is 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, still more preferably 50% by mass or less, still more preferably 40% by mass or less.
  • the molar ratio (A) / (B) of the component derived from the component (A) to the component derived from the component (B) in the fiber treatment agent of the present invention is such that the water-soluble condensates are contained in the naturally derived fiber. From the viewpoint of further improving the shape sustainability and strength of the naturally-derived fiber after treatment by the condensate having a larger molecular weight formed by condensation, it is preferably 0.005 or more, more preferably 0.01 or more, still more preferable. Is 0.05 or more, more preferably 0.1 or more, and from the viewpoint of good feel, it is preferably less than 5, more preferably 4 or less, still more preferably 3 or less, and even more preferably 2 or less.
  • the molar ratio (A) / (B) of the component derived from the component (A) to the component derived from the component (B) is the condensation formed by the condensation of the water-soluble condensates in the naturally derived fiber.
  • the material is preferably 0.005 or more and less than 5, more preferably 0.01 to 4, still more preferably 0.05. It is ⁇ 3, and even more preferably 0.1 ⁇ 2.
  • the condensate of the component (A) and the component (B) can be produced in the composition by heating the composition containing the components (A) to (C).
  • the component (A) and the component (B) are present in a free reaction with each other at the beginning of preparation, but by heating this composition, the composition is present. Both react to form a water-soluble condensate.
  • the content of the condensate produced from the components (A) and (B) in the fiber treatment agent of the present invention is preferably 1% by mass from the viewpoint of imparting high shape durability and strength to the naturally-derived fiber after treatment. Ultra, more preferably 1.5% by mass or more, still more preferably 2.5% by mass or more, still more preferably 5% by mass or more, still more preferably 10% by mass or more, and in addition to the above viewpoint, the surface of naturally derived fibers. From the viewpoint of improving the feel of the material, it is preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, still more preferably 50% by mass or less, still more preferably 40% by mass or less. ..
  • the fiber treatment agent of the present invention uses water as a medium.
  • the content of the component (C) 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, still more preferably 40% by mass or more. Further, it is preferably 99% by mass or less, more preferably 97% by mass or less, still more preferably 95% by mass or less, still more preferably 90% by mass or less. That is, the content of the component (C) in the fiber treatment agent of the present invention is preferably 10 to 99% by mass, more preferably 20 to 97% by mass, still more preferably 30 to 95% by mass, and even more preferably 40. ⁇ 90% by mass.
  • Component (D) Organic compound having a Hansen solubility parameter SP value of 16-40 MPa 1/2
  • a hard resin layer is formed on the surface of the naturally derived fiber, whereby the naturally derived fiber is formed. Movements such as bending and stretching of the fiber are restricted, which not only hinders the elasticity (tenacity) of the fiber, but also may deteriorate the feel of the fiber surface.
  • the treatment of naturally derived fibers has the solubility of Hansen from the viewpoint of preventing the aggregation of the condensate oligomer composed of the components (A) and (B) generated in the reaction process and causing the increase in turbidity and facilitating the dissolution. It is preferable to contain an organic compound having an SP value of 16 MPa 1/2 or more and 40 MPa 1/2 or less (excluding organic salts and compounds having a molecular weight of 150 or less having an aldehyde group).
  • the SP value of the solubility parameter of Hansen is 25 in the DIY program using the software package HSPiP 4th Edition 4.1.07 based on Hansen Solubility Parameters: A User's Handbook, CRC Press, Boca Raton FL, 2007. It means ⁇ Tot (MPa 1/2 ) calculated at °C.
  • Organic compounds having a SP value of Hansen's solubility parameter of component (D) of 16.0 MPa 1/2 or more and 40.0 MPa 1/2 or less include monohydric alcohols, dihydric alcohols, dihydric alcohol derivatives, and many trivalents or more.
  • Valuable alcohols, lactams, imidazolidinones, pyrimidinones, lactones, alkylene carbonates, and other general-purpose organic solvents having an SP value within the above range can be mentioned.
  • Examples of monohydric alcohols ethanol (25.4), 1-propanol (22.9), isopropyl alcohol (22.3), 1-butanol (22.9)
  • Examples of dihydric alcohols ethylene glycol (31.6), diethylene glycol (29.2), triethylene glycol (26.1), tetraethylene glycol (24.3), pentaethylene glycol (23.1), hexaethylene glycol (22.2), propylene glycol (31.7) ), 1-Dipropylene glycol (26.0), Tripropylene glycol (23.4)
  • Examples of dihydric alcohol derivatives dipropylene glycol monomethyl ether (21.1), dipropylene glycol dimethyl ether (17.8), dipropylene glycol diacetate (19.0), dipropylene glycol monomethyl ether acetate (18.5) ⁇
  • Examples of trihydric alcohols dipropylene glycol monomethyl ether (21.1), dipropylene glycol dimethyl ether (17.8), dipropylene glycol diacetate (19.0), dipropylene glycol monomethyl
  • the SP value of the Hansen solubility parameter is 35.8 from the viewpoint of preventing aggregation of the condensate oligomer composed of the components (A) and (B) generated in the reaction process and causing an increase in turbidity and facilitating dissolution.
  • Those having a MPa of 1/2 or less are preferable, those having a MPa of 34.7 MPa 1/2 or less are more preferable, and those having a MPa of 29.2 MPa 1/2 or less are further preferable.
  • those having 17.8 MPa 1/2 or more are preferable, those having 21.1 MPa 1/2 or more are more preferable, and those having 22.0 MPa 1/2 or more are further preferable.
  • dihydric alcohol lactam and imidazolidinone are preferred, with diethylene glycol (29.2), triethylene glycol (26.1), N-methylpyrrolidone (22.0), 1,3-dimethyl-2-imidazolidinone (22.3) and At least one selected from DMDM hydantoin (28.1) is more preferred.
  • Ingredient (D) can be used alone or in combination of two or more.
  • the content of the component (D) in the fiber treatment agent of the present invention is preferably 10% by mass or more, more preferably 15% by mass, from the viewpoint of maintaining the turbidity of the fiber treatment agent at 1000 NTU or less for a longer period of time.
  • the concentration is more preferably 25% by mass or more, and the condensation reaction is efficiently promoted, and the water-soluble condensates are bonded to each other in the naturally-derived fibers to form a condensate having a larger molecular weight.
  • it is preferably 80% by mass or less, more preferably 60% by mass or less, and further preferably 45% by mass or less.
  • the fiber treatment agent of the present invention may contain a cationic surfactant as long as the effects of the present invention are not impaired.
  • the cationic surfactant is preferably a monolong-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.
  • At least one monolong-chain alkyl quaternary ammonium surfactant is selected from the compounds represented by the following general formula.
  • R 4 is a saturated or unsaturated linear or branched alkyl group having 8 to 22 carbon atoms, R 8 -CO-NH- (CH 2 ) m- or R 8 -CO-O- (CH). 2 ) m- (R 8 indicates a saturated or unsaturated linear or branched alkyl chain having 7 to 21 carbon atoms, and m indicates an integer of 1 to 4), R 5 , R 6 and R.
  • X- indicates a chloride ion, a bromide ion, a metosulfate ion or an etosulfate 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 thereof.
  • the content of the cationic surfactant in the fiber treatment agent of the present invention is preferably 0.05% by mass or more, more preferably from the viewpoint of improving the feel of the naturally-derived fiber after treatment and further improving the effect of the present invention. Is 0.10% by mass or more, preferably 10% by mass or less, and more preferably 5% by mass or less.
  • the fiber treatment agent of the present invention may contain silicone from the viewpoint of improving the feel of naturally derived fibers after treatment and improving the cohesiveness.
  • silicone one or more selected from dimethylpolysiloxane and amino-modified silicone are preferable.
  • any cyclic or acyclic dimethylpolysiloxane polymer can be used, and examples thereof include 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) Industrial Co., Ltd.).
  • any silicone having an amino group or an ammonium group can be used, and examples thereof include an amino-modified silicone oil in which all or part of the terminal hydroxyl groups are end-sealed with a methyl group or the like, and a terminal seal. Amodimethicone that has not been stopped can be mentioned. From the viewpoint of improving the feel of naturally-derived fibers after treatment and improving the cohesiveness, preferable amino-modified silicones include compounds represented by the following formulas.
  • R' represents a hydrogen atom, a hydroxyl group or RX
  • 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 Indicates NH 2 , OR X or hydroxyl group
  • a indicates a number of 0 to 3
  • b and c indicate the sum of the numbers.
  • the number is 10 or more and less than 20000, preferably 20 or more and less than 3000, more preferably 30 or more and less than 1000, and further preferably 40 or more and less than 800.
  • suitable commercially available amino-modified silicone products include SF8452C, SS3551 (all from Toray Dow Corning Co., Ltd.), KF-8004, KF-867S, KF-8015 (all from Shin-Etsu Chemical Co., Ltd.), etc.
  • Examples include amodimethicone emulsions such as amino-modified silicone oil, SM8704C, SM8904, BY22-079, FZ-4671, and FZ4672 (all from Toray Dow Corning 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 feel of naturally derived fibers after treatment and further improving the effect of the present invention. As mentioned above, it is more preferably 0.5% by mass or more, preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably 5% by mass or less.
  • the fiber treatment agent of the present invention can contain a cationic polymer from the viewpoint of improving the feel of naturally derived fibers after treatment.
  • the cationic polymer means a polymer having a cationic group or a group that can be ionized by the cationic group, and also includes an amphoteric polymer that becomes cationic as a whole. That is, an aqueous solution containing an amino group or an ammonium group in the side chain of the polymer chain or containing a diallyl quaternary ammonium salt as a constituent unit, for example, a cationized cellulose derivative, a cationic starch, a cationized guar gum derivative, or a diallyl quaternary ammonium salt. Examples thereof include a polymer or copolymer of an ammonium salt and a quaternary polyvinylpyrrolidone derivative.
  • diallyl quaternary ammonium is used from the viewpoint of improving the softness, smoothness and finger passage during rinsing and shampooing, the cohesiveness and moisturizing properties during drying, and the stability of the agent.
  • One or more selected from polymers containing salts as constituent units, quaternary polyvinylpyrrolidone derivatives, and cationized cellulose derivatives are preferable, and polymers or copolymers of diallyl quaternary ammonium salts and cationized cellulose derivatives are selected.
  • One kind or two or more kinds are more preferable.
  • polymer or copolymer of a suitable diallyl quaternary ammonium salt examples include dimethyldiallyl ammonium chloride polymer (polyquaternium-6, for example, Marcourt 100; Lubrizol Advanced Materials), dimethyldiallyl ammonium chloride /.
  • Acrylic acid copolymer Polyquaternium-22, eg, Marcourt 280, 295; Lubrisol Advanced Materials
  • Dimethyldiallyl ammonium chloride / acrylamide polymer Polyquaternium-7, eg, Marcourt 550; Lubrisol Advanced Materials. Materials Co., Ltd.) and the like.
  • polyquaternium 11 a polymer obtained by polymerizing a vinylpyrrolidone copolymer and dimethylaminoethyl methacrylate (polyquaternium 11, for example, Gaffcut 734, Gaffcut 755, Gaffcut 755N (above, Ashland)).
  • suitable cationized cellulose include polymers in which hydroxycellulose is loaded with glycidyltrimethylammonium chloride (polyquaternium 10, for example, Leoguard G, GP (above, Lion), polymers JR-125, JR-400, and the same. JR-30M, LR-400, LR-30M (above, Amercol), hydroxyethyl cellulose dimethyldiallylammonium chloride (polyquaternium-4, for example, Cellcoat H-100, L-200 (above, Axonobel)) ) Etc. can be mentioned.
  • 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 0.05% by mass from the viewpoint of improving the feel of naturally derived fibers after treatment. % 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, hydrochloric acid and tartrate acid.
  • an antioxidant such as ascorbic acid
  • a pH adjuster such as sodium hydroxide, potassium hydroxide, phosphoric acid, hydrochloric acid and tartrate acid.
  • the fiber treatment agent of the present invention is preferably as low as possible in turbidity from the viewpoint of improving the elasticity (toughness) of naturally derived fibers and improving the feel of the fiber surface, and the turbidity of the fiber treatment agent is It is 1000 NTU or less, preferably 500 NTU or less, more preferably 100 NTU or less, and further preferably 20 NTU or less.
  • the turbidity of the above-mentioned fiber treatment agent refers to turbidity derived from the water-insoluble condensate formed by binding the component (B) and the water-soluble condensates to each other, and other causes of turbidity.
  • the quantification of the water-insoluble condensate can be performed by, for example, a derivatized pyrolysis GC / MS method after filtering with a membrane filter having a hole diameter of 0.1 ⁇ m.
  • NTU Nephelometric Turbidity Unit
  • the turbidity of the fiber treatment agent can be measured at room temperature (25 ° C.) by putting the fiber treatment agent in the measuring cell of a digital turbidity meter (manufactured by AS ONE, model number: TB700) as it is.
  • the pH of the fiber treatment agent of the present invention is preferably 3.0 or more, more preferably 3.5 or more, still more preferably 4.0 or more, still more preferably 4.5 or more, and preferably 12.0 or more, from the viewpoint of suppressing damage to naturally derived fibers. Below, it is more preferably 11.0 or less, still more preferably 10.0 or less, still 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 3.0 to 12.0, more preferably 3.5 to 11.0, still more preferably 4.0 to 10.0, still more preferably 4.5 to 9.0, from the viewpoint of suppressing damage to naturally derived fibers. be.
  • the fiber treatment agent of the present invention contains components (A) to (C), and the total of the components derived from the component (A) and the components derived from the component (B) is more than 1% by mass. Can be produced by heating until the turbidity is 1000 NTU or less.
  • the component (A) and the component (B) are present in a free reaction with each other at the beginning of preparation, and the turbidity is high. By heating the composition, the two react to form a water-soluble condensate, which reduces the turbidity of the composition.
  • the fiber treatment agent of the present invention is a composition in this state having a turbidity of 1000 NTU or less.
  • the heating temperature for setting the turbidity of the composition containing the components (A) to (C) to 1000 NTU or less is a water-soluble condensate in which the component (A) and the component (B) in the fiber treatment agent react with each other. From the viewpoint of efficiently advancing the reaction to generate It is preferably 120 ° C. or lower, more preferably 115 ° C. or lower, still more preferably 110 ° C. or lower.
  • the heating time is preferably 1 minute or longer, more preferably 5 minutes or longer, preferably 20 minutes or shorter, and more preferably 15 minutes or shorter. It is desirable to raise the temperature to the above temperature in a short time, and after confirming the transparency by heating and stirring, cool the temperature in a short time to lower the temperature to the fiber application temperature or the storage temperature of the fiber treatment agent described later. When it is difficult to raise the temperature rapidly due to scale-up, it is advantageous to raise the temperature in a state where the composition other than the component (B) is mixed and add the component (B) in the state where the temperature reaches the above temperature.
  • the pH of the composition containing the components (A) to (C) at the time of heating is preferably 7.0 or more, more preferably 8.0 or more, and further, from the viewpoint of preventing the reaction from becoming too fast and entering Phase 3. It is preferably 9.0 or more, and is preferably 13.0 or less, more preferably 12.0 or less, still more preferably 11.0 or less, from the viewpoint of workability that facilitates pH adjustment at the time of application to fibers. After the turbidity of the composition becomes 1000 NTU or less, the pH range of the above-mentioned fiber treatment agent can be adjusted as necessary.
  • the storage temperature is set to a cold temperature in order to prevent unintended reaction progress during transport. You can also do it.
  • the storage temperature is preferably 1 ° C. or higher, more preferably 2 ° C. or higher, still more preferably 5 ° C. or higher from the viewpoint of preventing freezing or recrystallization, and from the viewpoint of preventing unintended reaction progress. It is preferably 25 ° C. or lower, more preferably 20 ° C. or lower, still more preferably 15 ° C. or lower.
  • the pH of the fiber treatment agent during storage is preferably adjusted to the range of 9 to 11 where the condensation rate is slow.
  • the naturally-derived fiber is shaped into a naturally-derived fiber while maintaining a high degree of elasticity (toughness) of the naturally-derived fiber. It can impart durability and high durability.
  • step (i) A step of immersing naturally-derived fibers in the fiber treatment agent of the present invention and treating the treatment agent while maintaining the turbidity of 1000 NTU or less.
  • the fiber treatment agent having a turbidity of 1000 NTU or less of the present invention manufactured as described above may be applied to the fiber as it is, but the turbidity does not increase due to the treatment agent being in Phase 3.
  • the elasticity of the fiber can be further enhanced by applying it to the fiber after heating it for a certain period of time. Therefore, it is preferable to include the following step (0) before the step (i). (0) Step of heating the fiber treatment agent
  • the heating temperature in the step (0) is preferably 40 ° C. or higher, more preferably 60 ° C. or higher, still more preferably 70 ° C. or higher, and the heating can be stopped at an appropriate point. From the viewpoint, it is preferably 120 ° C. or lower, more preferably 105 ° C. or lower, and further preferably 99 ° C. or lower.
  • the heating time in step (0) is defined as T when the treatment agent having a turbidity of 1000 NTU or less immediately after preparation is heated and the treatment agent enters Phase 3 until the turbidity exceeds 1000 NTU again.
  • the turbidity is preferably 0.2 T or more, more preferably 0.3 T or more, further preferably 0.4 T or more, and the turbidity exceeds 1000 NTU in Phase 3.
  • it is preferably 0.8 T or less, more preferably 0.7 T or less, and further preferably 0.6 T or less.
  • the naturally occurring fibers immersed in the fiber treatment agent may be dry or wet.
  • the amount of the fiber treatment agent for immersing the naturally-derived fiber is a bath ratio (mass of the fiber treatment agent / mass of the naturally-derived fiber) with respect to the mass of the naturally-derived fiber, and is preferably 2 or more, more preferably 3 or more, still more preferably. Is 5 or more, more preferably 10 or more, still more preferably 20 or more, still preferably 500 or less, more preferably 250 or less, still more preferably 100 or less. That is, the bath ratio is preferably 2 to 500, more preferably 3 to 250, still more preferably 5 to 100, still more preferably 10 to 100, and even more preferably 20 to 100.
  • 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 naturally-derived fibers in addition to shape durability and high durability.
  • Immersion of naturally-derived fibers in the fiber treatment agent in step (i) is performed under heating, and this heating is performed by heating the fiber treatment agent.
  • This heating may be performed by immersing the naturally-derived fiber in the heated fiber treatment agent, or by immersing the naturally-derived fiber in the low-temperature fiber treatment agent and then heating the fiber.
  • the temperature of the fiber treatment agent increases the interaction between the water-soluble condensate formed from the component (A) and the component (B) and the fiber-constituting molecule in the naturally-derived fiber, for example, a protein molecule, and also in the naturally-derived fiber.
  • the temperature is preferably 20 ° C or higher, more preferably 35 ° C or higher, still more preferably 45.
  • the temperature is preferably lower than 100 ° C, more preferably 80 ° C or lower, still more preferably 70 ° C or lower, still more preferably 60 ° C or lower, in order to prevent naturally-derived fibers from being denatured and deteriorated by heat. be.
  • the immersion time in step (i) is the elasticity to naturally derived fibers when the heating time until the treatment agent has a turbidity of 1000 NTU or less immediately after preparation is defined as T. From the viewpoint of exhibiting the improving effect, it is preferably 0.3T or more, more preferably 0.4T or more, further preferably 0.5T or more, and preferably 0.95T or less, more preferably 0.95T or less in order to suppress damage to naturally derived fibers. It is 0.90T or less, more preferably 0.85T or less.
  • the specific immersion time is appropriately adjusted depending on the heating temperature used, but for example, from the viewpoint of exhibiting the effect of improving the elasticity of naturally derived fibers, it is preferably 15 minutes or more, more preferably 30 minutes or more, still more preferably. It is 1 hour or more, and is preferably 48 hours or less, more preferably 24 hours or less, still more preferably 12 hours or less in order to suppress damage to naturally derived fibers.
  • Step (i) is preferably performed in an environment where evaporation of water is suppressed.
  • Specific means for suppressing the evaporation of water include a method of covering a container of a fiber treatment agent in which naturally-derived fibers are immersed with a film-like substance made of a material that does not allow water vapor to pass through, a cap, a lid, or the like.
  • the naturally derived fibers may or may not be rinsed, but rinsing is preferable from the viewpoint of preventing the feeling of the naturally derived fibers from being deteriorated by the excess polymer.
  • a hard resin layer is formed on the surface of the naturally derived fiber, which makes it difficult to maintain a high degree of elasticity (tenacity) of the naturally derived fiber. Since it is difficult to secure a good feel on the fiber surface, it is preferable to remove the naturally derived fiber from the treatment agent before the turbidity of the treatment agent exceeds 1000 NTU.
  • the turbidity of the treatment agent can be confirmed by the above-mentioned turbidity measurement method by appropriately collecting a sample from the treatment agent. If the treated naturally-derived fiber that has been taken out is insufficiently treated, the process (i) may be performed again.
  • step (i) is followed by the following step (ii), and the step (i) and the step (ii) are repeated two or more times.
  • step (ii) The process of removing naturally derived fibers from the treatment agent before the turbidity of the treatment agent exceeds 1000 NTU.
  • step (ii) After removing the naturally derived fiber from the treatment agent in the above step (ii), it is preferable to rinse the surface of the naturally derived fiber to wash away the insoluble condensate. That is, it is preferable to perform the following step (iii) after the step (ii). (iii) Rinsing process of taken out naturally derived fiber
  • the rinsing composition may be composed of only the component (D), or may contain water in addition to the component (D).
  • the content of the component (D) in the rinsing composition when water is contained is preferably 60% by mass or more, more preferably 80% by mass or more, and even more preferably 95% by mass or more.
  • Step of immersing naturally derived fibers in a post-crosslinking agent containing components (E) and (C) (E): Formaldehyde, hydrate of formaldehyde, glyoxal acid, hydrate of glyoxylic acid, glyoxal salt , Glyoxal, glyoxal hydrate, glutalaldehyde, and at least one formaldehyde derivative (C) selected from glyoxal aldehyde hydrate: water.
  • the content of the component (E) in the post-crosslinking agent is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 1% by mass or more, and preferably 60% by mass or less, more preferably. It is 40% by mass, more preferably 20% by mass or less. That is, the content of the component (E) in the post-crosslinking agent is preferably 0.01 to 60% by mass, more preferably 0.1 to 40% by mass, and further preferably 1 to 20% by mass.
  • the post-crosslinking agent can contain a pH adjuster such as sodium hydroxide, potassium hydroxide, phosphoric acid, hydrochloric acid, and an organic acid.
  • a pH adjuster such as sodium hydroxide, potassium hydroxide, phosphoric acid, hydrochloric acid, and an organic acid.
  • the post-crosslinking agent does not contain the triazine derivative of the component (B).
  • the pH of the post-crosslinking agent is preferably 11.0 or less, more preferably 10.0 or less, still more preferably 9.0 or less, and preferably 2.0 or more, more preferably 3.0 or more, from the viewpoint of suppressing damage to naturally derived fibers. More preferably, it is 4.0 or more. That is, the pH of the post-crosslinking agent is preferably 2.0 to 11.0, more preferably 3.0 to 10.0, and even more preferably 4.0 to 9.0, from the viewpoint of suppressing damage to naturally-derived fibers.
  • the temperature of the post-crosslinking agent used in step (iv) is the interaction between the condensate of component (A) and component (B) produced in the naturally derived fiber and the fiber constituent molecules in the naturally derived fiber, such as protein molecules.
  • the temperature is preferably 20 ° C. or higher, more preferably 35 ° C. or higher, still more preferably 45 ° C. or higher, and the naturally derived fiber is denatured by heat. It is preferably less than 100 ° C., more preferably 80 ° C. or lower, still more preferably 70 ° C. or lower, still more preferably 60 ° C. or lower, from the viewpoint of preventing deterioration.
  • the naturally occurring fibers immersed in the post-crosslinking agent may be dry or wet.
  • the amount of the post-crosslinking agent for immersing the naturally-derived fiber is a bath ratio to the mass of the natural fiber (mass of the post-crosslinking agent / mass of the fiber treated in steps (i) to (iii)), preferably 2.
  • the above is more preferably 3 or more, still more preferably 5 or more, still more preferably 10 or more, still more preferably 20 or more, still preferably 500 or less, more preferably 250 or less, still more preferably 100 or less. That is, the bath ratio is preferably 2 to 500, more preferably 3 to 250, still more preferably 5 to 100, still more preferably 10 to 100, and even more preferably 20 to 100.
  • the immersion time of the naturally-derived fiber in the post-crosslinking agent is preferably 1 minute or longer, more preferably 3 minutes or longer, still more preferably 5 in order to permeate and diffuse the post-crosslinking agent into the naturally-derived fiber. It is more than a minute, preferably 5 hours or less, more preferably 3 hours or less, still more preferably 1 hour or less.
  • the fiber treatment method of the present invention further provides decolorization, dyeing, surface finishing for imparting hydrophobicity and low friction, and further fiber elasticity (tenacity).
  • Each one or more treatments selected from the heat treatments for improvement may be additionally performed.
  • the decolorization and dyeing treatments may be performed before or after the above-mentioned steps (i) to (iv), and between the steps (i) to (iv). You may go to. It is also possible to add multiple treatments in combination, and if both bleaching and dyeing are to be added, any treatment may be performed first, except that bleaching must be performed prior to dyeing. , Another treatment can be performed between bleaching and dyeing.
  • the surface finish for imparting hydrophobicity and low friction, and the heat treatment for further improving the fiber elasticity (tenacity) are performed after the above-mentioned steps (i) to (iii) or in step (iv).
  • the treatment with the post-crosslinking agent is also performed, it is necessary to perform the treatment after the step (iv), and in particular, by further performing the treatment after the step (iv), better results can be obtained.
  • the surface finish for imparting hydrophobicity and low friction, and the heat treatment for further improving the fiber elasticity (tenacity) are performed after the steps (i) to (iii) or the step (iv) as described above.
  • the order of processing with decolorization and dyeing is not particularly limited as long as it is performed at the stage of.
  • Decolorization is performed by immersing naturally derived fibers in a decolorizing agent composition containing an alkaline agent, an oxidizing agent and water.
  • the decolorizing agent composition is usually a two-dosage form, the first agent containing an alkaline agent and water, and the second agent containing an oxidizing agent and water.
  • the two agents are usually stored separately and mixed prior to dipping the naturally occurring fibers.
  • Suitable alkaline agents include, for example, ammonia and salts thereof; alkanolamines (monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol, etc.) and salts thereof; alcandiamine (1,3). -Propanediamine etc.) and salts thereof; and carbonates (guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc.); and mixtures thereof include, but are not limited to.
  • 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, still more preferably 1% by mass. % Or more, preferably 15% by mass or less, more preferably 10% by mass or less, still more preferably 7.5% by mass or less.
  • Suitable oxidizing agents include, but are not limited to, hydrogen peroxide, urea peroxide, melamine peroxide and sodium bromate. Among these oxidizing agents, hydrogen peroxide is preferable.
  • 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, still 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. be. This pH can be adjusted with a suitable buffer.
  • the pH of the decolorizing agent composition at 25 ° C. is preferably 6 or more, more preferably 6.5 or more, still more preferably 6.8 or more, and preferably 11 or less, more preferably 10.5 or less, still more preferably 10 or less. ..
  • the dyeing agent composition contains a dye, and may optionally contain an alkaline agent, an acid, an oxidizing agent, or the like.
  • the dye include a direct dye, an oxidation dye and a combination 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 having an azophenol structure selected from the group consisting of HC Red 18, HC Blue 18 and HC Yellow 16 below, and these. Examples include 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.
  • Examples include, but are not limited to, Yellow 87 and mixtures thereof.
  • Basic Red 51, Basic Orange 31, Basic Yellow 87 and mixtures thereof are particularly preferred.
  • 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, and 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.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
  • the 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 and 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, and 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 dye examples 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 having 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, still more preferably 0.05% by mass or more, and blended, from the viewpoint of obtaining sufficient dyeability. From the viewpoint of sex, it is preferably 10% by mass or less, more preferably 7.5% by mass or less, still more preferably 5.0% by mass or less, still more preferably 3.0% by mass or less.
  • the dyeing composition contains only the direct dye as a dye, no oxidizing agent is required to dye the naturally occurring fiber, but if the color of the naturally occurring fiber is to be lightened, the oxidizing agent is contained in the composition. You can also let it.
  • the dye composition contains an oxidative dye
  • the first agent contains an oxidative dye intermediate (precursor and coupler) and an alkaline agent
  • the second agent contains an oxidant such as hydrogen peroxide.
  • the two agents are usually stored separately and mixed prior to dipping the naturally occurring fibers.
  • the oxidation dye intermediate is not particularly limited, and any known precursor or coupler usually used for dyeing products can be preferably used.
  • Precursors include, for example, paraphenylenediamine, toluene-2,5-diamine, 2-chloro-paraphenylenediamine, N-methoxyethyl-paraphenylenediamine, N-phenylparaphenylenediamine, N, N-bis (2-).
  • coupler examples include metaphenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4- (2-hydroxyethylamino) anisole, 2,4-diamino-5-methylphenetol, and 2,4-diamino-.
  • the contents of the precursor and the coupler in the dye composition are 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, respectively. More preferably, it is 5% by mass or less.
  • the dyeing agent composition contains an oxidative dye, it further contains an alkaline agent.
  • alkaline agents include, for example, ammonia and salts thereof; alkanolamines (monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol, etc.) and salts thereof; alcandiamine (1,3). -Propanediamine etc.) and salts thereof; and carbonates (guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc.); and mixtures thereof include, but are not limited to.
  • the content of the alkaline agent in the dyeing agent composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, still more preferably 1% 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 oxidant is stored separately from the composition containing the oxidative dye (first agent) and mixed before immersing the naturally derived fiber.
  • Suitable oxidizing agents include, but are not limited to, hydrogen peroxide, urea peroxide, melamine peroxide and sodium bromate. Among these oxidizing agents, hydrogen peroxide is preferable.
  • the content of the oxidizing agent in the dyeing 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, still 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. Is. This pH can be adjusted with a suitable buffer.
  • the pH of the dyeing agent composition obtained by mixing the first agent and the second agent at 25 ° C. is preferably 6 or more, more preferably 6.5 or more, still more preferably 6.8 or more, and preferably 11 or less. It is preferably 10.5 or less, more preferably 10 or less.
  • the dyeing agent composition contains an oxidative dye, it can further contain the direct dye exemplified above.
  • the dyeing agent composition can preferably further contain the following surfactants, conditioning components and the like, and can preferably take the form of a solution, emulsion, cream, paste and mousse.
  • the temperature of the dyeing composition is preferably 0 ° C. or higher, more preferably 10 ° C. or higher, still more preferably 10 ° C. or higher, from the viewpoint of efficiently permeating and diffusing the dyeing agent composition into naturally derived fibers and further enhancing the dyeing effect. It is 20 ° C. or higher, preferably 90 ° C. or lower, and more preferably 80 ° C. or lower.
  • the surface finish for imparting hydrophobicity and reducing friction is a step after the above-mentioned steps (i) to (iii), and when the treatment with a cross-linking agent is performed after the step (iv), the step (iv) At a later stage, this is done by immersing naturally derived fibers in the surface finishes shown below.
  • the surface finishing agent contains the following components (F) and (C).
  • F Epoxyaminosilane copolymer which is a reaction product of the following compounds (a) to (d)
  • Ether (c) Aminopropyltrialkoxysilane
  • Component (F): Epoxy Aminosilane Copolymer The epoxy aminosilane copolymer of the component (F) is a reaction product of the compounds (a) to (d) shown below.
  • the compound (a) is a polysiloxane containing at least two oxylanyl groups or oxetanyl groups, and examples thereof include those represented by the following general formula (5).
  • R represents a hydrocarbon group having 1 to 6 carbon atoms which may contain a hetero atom and having an oxylanyl group or an oxetanyl group at the terminal, and x represents a number of 1 to 1000.
  • the compound (b) is a polyether containing at least two oxylanyl groups or oxetanyl groups, and examples thereof include those represented by the following general formula (6).
  • R has the same meaning as described above, y is 1 to 100, z is 0 to 100, and y + z is 1 to 200. ]
  • R includes oxylanylmethyl group (glycidyl group), oxylanylmethoxy group (glycidyloxy group), oxylanylmethoxypropyl group (glycidyloxypropyl group), oxetanylmethyl group, oxetanylmethoxy group, oxetanylmethoxypropyl group, Examples thereof include 3-ethyloxetanylmethyl group, and among them, a hydrocarbon group having an oxylanyl group and which may contain a heterooxygen atom and having 1 to 4 carbon atoms is preferable, and an oxylanylmethyl group (glycidyl group) and an oxyla are preferable. At least one selected from an enylmethoxy group (glycidyloxy group) and an oxylanylmethoxypropyl group (glycidyloxypropyl group) is
  • Compound (c) is aminopropyltrialkoxysilane.
  • alkoxy group in the compound (c) include those having 1 to 6 carbon atoms, preferably those having 2 to 4 carbon atoms, and more preferably those having 3 carbon atoms, and among them, an isopropoxy group is preferable.
  • Examples of the compound (c) include aminopropyltrimethoxysilane, aminopropyltriethoxysilane, aminopropyltripropoxysilane, aminopropyltriisopropoxysilane, aminopropyltributoxysilane, and aminopropyltritert-butoxysilane. However, aminopropyltriisopropoxysilane is preferable.
  • Compound (c) can be used alone or in combination of two or more.
  • Compound (d) is a compound selected from the group consisting of the following primary and secondary amines.
  • -Primary amines methylamine, ethylamine, propyleneamine, ethanolamine, isopropylamine, butylamine, isobutylamine, hexylamine, dodecylamine, oleylamine, aniline, aminopropyltrimethylsilane, aminopropyltriethylsilane, aminomorpholin, aminoethyl Dimethylamine, aminoethyldiethylamine, aminoethyldibutylamine, aminopropyldimethylamine, aminopropyldibutylamine, aminopropyldibutylamine, benzylamine, naphthylamine, 3-amino-9-ethylcarbazole, 1-aminoheptafluorohexane, 2,2 , 3,3,4,4,5,5,6,6,7,7,8,8,8,
  • primary amines are preferred, and one selected from aminopropyldiethylamine, aminopropyldimethylamine, and aminopropyldibutylamine is even more preferred.
  • Compound (d) can be used alone or in combination of two or more.
  • the reaction of compounds (a) to (d) is carried out by refluxing in a solvent such as isopropanol for a certain period of time.
  • a solvent such as isopropanol
  • the molar ratio of the oxylanyl group or the oxetanyl group of the compounds (a) and (b) to the amino group of the compound (c) is preferably 1 or more, more preferably 1.1 or more, still more preferably 1.2 or more, and also. It is preferably 4 or less, more preferably 3.9 or less, and further preferably 3.8 or less.
  • component (F) examples include those having the INCI name of Polysilicone-29, and an example of a commercially available product thereof is Silsoft CLX-E (effective content 15% by mass, dipropylene) of Momentive Performance Materials. Glycol and water included).
  • the content of the component (F) in the surface finishing agent is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.10% by mass or more, from the viewpoint of imparting sufficient hydrophobicity to naturally derived fibers. It is more preferably 0.20% by mass or more, and from the viewpoint of not giving a sticky feel, it is preferably 15.00% by mass or less, more preferably 10.00% by mass or less, still more preferably 8.00% by mass or less, still more preferably 6.00% by mass. It is as follows.
  • the pH of the surface finishing agent at 25 ° C. is preferably in the following range from the viewpoint of increasing the reaction rate of the trialkoxysilane portion of the component (F) in the acidic region or the basic region.
  • the surface finishing agent is in an acidic region, it is preferably 1.0 or more, more preferably 1.5 or more, still more preferably 2.0 or more, preferably 5.0 or less, more preferably 4.0 or less, still more preferably 3.5 or less.
  • the surface finishing agent is a basic region, it is preferably 7.0 or more, more preferably 7.5 or more, still more preferably 8.0 or more, preferably 11.0 or less, more preferably 10.5 or less, still more preferably 10.0 or less. Is.
  • the surface finishing agent may appropriately contain a pH adjusting agent.
  • a pH adjuster as an alkaline agent, an alkanolamine such as monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol, 2-aminobutanol or a salt thereof; an alkanediamine such as 1,3-propanediamine or a salt thereof. Salts; carbonates such as guanidine carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and the like; hydroxides such as sodium hydroxide and potassium hydroxide can be used.
  • an inorganic acid such as hydrochloric acid and phosphoric acid
  • a hydrochloride such as monoethanolamine hydrochloride
  • a phosphate such as monopotassium dihydrogen phosphate and disodium monohydrogen phosphate
  • an organic acid such as lactic acid and malic acid. Acids and the like can be used.
  • the amount of the surface finishing agent for immersing the naturally-derived fiber is a bath ratio (mass of the surface finishing agent / mass of the naturally-derived fiber) to the mass of the naturally-derived fiber, and is preferably 2 or more, more preferably 5 or more, still more preferably. It is 10 or more, preferably 100 or less, more preferably 50 or less, still more preferably 20 or less.
  • the naturally derived fiber can be heated while being stretched by applying tension.
  • the fiber draw ratio during heating is preferably 0.1% or more, more preferably 0.2% or more, still more preferably 0.5% or more, and damage to the fiber, from the viewpoint of more effectively improving the elasticity of the fiber. From the viewpoint of suppression, it is preferably 10% or less, more preferably 5% or less, still more preferably 2% or less.
  • the heating temperature is preferably 120 ° C. or higher, more preferably 140 ° C. or higher, still more preferably 160 ° C. or higher, from the viewpoint of more effectively improving the elasticity of the fiber, and from the viewpoint of suppressing damage to the fiber. It is preferably 240 ° C. or lower, more preferably 220 ° C. or lower, and further preferably 200 ° C. or lower.
  • the heating time is preferably 1 second or longer, more preferably 3 seconds or longer, still more preferably 5 seconds or longer, from the viewpoint of more effectively improving the elasticity of the fiber, and from the viewpoint of suppressing damage to the fiber. It is preferably 60 seconds or less, more preferably 30 seconds or less, still more preferably 20 seconds or less.
  • the draw ratio at this time is preferably 0.1% or more, more preferably 0.2% or more, still more preferably 0.5% or more, and suppresses damage to the fibers, from the viewpoint of more effectively improving the elasticity of the fibers. From the viewpoint of the above, it is preferably 10% or less, more preferably 5% or less, still more preferably 2% or less.
  • the water temperature is preferably 5 ° C. or higher, more preferably 20 ° C. or higher, still more preferably 30 ° C. or higher from the viewpoint of more effectively improving the elasticity of the fiber, and from the viewpoint of suppressing damage to the fiber. It is preferably 80 ° C. or lower, more preferably 60 ° C. or lower, and even more preferably 50 ° C. or lower.
  • the standing time in water is preferably 1 minute or longer, more preferably 5 minutes or longer, still more preferably 30 minutes or longer, and damage to the fibers, from the viewpoint of more effectively improving the elasticity of the fibers. From the viewpoint of suppression, it is preferably 48 hours or less, more preferably 24 hours or less, still more preferably 3 hours or less.
  • the fibers By treating naturally-derived fibers by the above fiber treatment method, the fibers contain condensates produced from the components (A) and (B), resulting in excellent shape sustainability and tensile elastic modulus, which are naturally derived. Fibers for headdress products with highly improved elasticity (tenacity) of the fibers can be produced, and wigs can be produced using the fibers. Examples of the headdress product in the present invention include hair wigs, wigs, weaving, hair extensions, blade hairs, hair accessories, doll hairs and the like.
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • the content of the component derived from the component (A) in the fiber treatment agent is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 1.5% by mass or more, still more preferably 3% by mass or more. It is even more preferably 5% 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, still more preferably 35% by mass or less, still more preferably.
  • the fiber treatment agent according to ⁇ 1> which is 30% by mass or less.
  • Ingredient (B) is preferably melamine, monomethylol melamine, dimethylol melamine, trimethyl melamine, benzoguanamine, acetoguanamine, 2,4-diamino-1,3,5-triazine, ammerin, and 2-chloro-4, At least one selected from 6-diamino-1,3,5-triazine, more preferably at least one selected from melamine, monomethylol melamine, dimethylol melamine and trimethylol melamine, still more preferably melamine, ⁇ 1.
  • the fiber treatment agent according to ⁇ 2> is preferably melamine, monomethylol melamine, dimethylol melamine, trimethyl melamine, benzoguanamine, acetoguanamine, 2,4-diamino-1,3,5-triazine, ammerin, and 2-chloro-4, At least one selected from 6-diamino-1,3,5-triazine, more preferably at least one selected
  • the content of the component derived from the component (B) in the fiber treatment agent is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 2.5% by mass or more, still more preferably 5% by mass or more. It is preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less, still more preferably 35% by mass or less, still more preferably 30% by mass or less, ⁇ 1.
  • the total content of the component derived from the component (A) and the component derived from the component (B) in the fiber treatment agent is preferably 2.5% by mass or more, more preferably 5% by mass or more, still more preferably 10. It is preferably 80% by mass or less, more preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, still more preferably 50% by mass or less, still more preferably 40% by mass or less.
  • the fiber treatment agent according to any one of ⁇ 1> to ⁇ 4>.
  • the molar ratio (A) / (B) of the component derived from the component (A) to the component derived from the component (B) is preferably 0.005 or more, more preferably 0.01 or more, still more preferably 0.05 or more, and even more.
  • Fiber treatment agent is preferably 0.1 or more, preferably less than 5, more preferably 4 or less, still more preferably 3 or less, still more preferably 2 or less.
  • the content of the condensate produced from the components (A) and (B) is preferably more than 1% by mass, more preferably 1.5% by mass or more, still more preferably 2.5% by mass or more, still more preferably 5% by mass or more. Even more preferably 10% by mass or more, preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, still more preferably 50% by mass or less, still more preferably 40.
  • the content of the component (C) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, still more preferably 40% by mass or more. Further, it is described in any one of ⁇ 1> to ⁇ 7>, preferably 99% by mass or less, more preferably 97% by mass or less, still more preferably 95% by mass or less, still more preferably 90% by mass or less. Fiber treatment agent.
  • D Organic compounds having a Hansen solubility parameter SP value of 16 MPa 1/2 or more and 40 MPa 1/2 or less (excluding organic salts and compounds having a molecular weight of 150 or less having an aldehyde group).
  • the component (D) is preferably at least one selected from monohydric alcohols, dihydric alcohols, dihydric alcohol derivatives, trihydric or higher polyhydric alcohols, lactam, imidazolidinone, pyrimidinone, lactones, alkylene carbonates and general-purpose organic solvents. From species, more preferably at least one selected from dihydric alcohols, lactams and imidazolidinones, more preferably from diethylene glycol, triethylene glycol, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and DMDM hydantin.
  • the fiber treatment agent according to ⁇ 9> which is at least one selected.
  • the SP value of the Hansen solubility parameter of the component (D) is preferably 35.8 MPa 1/2 or less, more preferably 34.7 MPa 1/2 or less, still more preferably 29.2 MPa 1/2 or less, and preferably 17.8.
  • the fiber treatment agent according to ⁇ 9> or ⁇ 10> which has a MPa of 1/2 or more, more preferably 21.1 MPa 1/2 or more, and even more preferably 22.0 MPa 1/2 or more.
  • the cationic surfactant is preferably a monolong-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, more preferably the following general formula.
  • R 4 is a saturated or unsaturated linear or branched alkyl group having 8 to 22 carbon atoms, R 8 -CO-NH- (CH 2 ) m- or R 8 -CO-O- (CH). 2 ) m- (R 8 indicates a saturated or unsaturated linear or branched alkyl chain having 7 to 21 carbon atoms, and m indicates an integer of 1 to 4), R 5 , R 6 and R.
  • X- indicates a chloride ion, a bromide ion, a metosulfate ion or an etosulfate ion.
  • the content of the cationic surfactant is preferably 0.05% by mass or more, more preferably 0.10% by mass or more, and preferably 10% by mass or less, more preferably 5% by mass or less, ⁇ 12> or.
  • the fiber treatment agent according to any one of ⁇ 1> to ⁇ 14> which further preferably further contains one or more selected from silicone, more preferably dimethylpolysiloxane and amino-modified silicone.
  • the content of silicone 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, and preferably 20% by mass or less, more preferably 10% by mass or less, still more preferably. Is 5% by mass or less, according to ⁇ 15>.
  • the content of the cationic polymer is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, further preferably 0.05% by mass or more, and preferably 20% by mass or less, more preferably 10% by mass or less.
  • turbidity is preferably 500 NTU or less, more preferably 100 NTU or less, still more preferably 20 NTU or less.
  • the pH is preferably 3.0 or higher, more preferably 3.5 or higher, still more preferably 4.0 or higher, still more preferably 4.5 or higher, and preferably 12.0 or lower, more preferably 11.0 or lower, still more preferably 10.0 or lower, even more preferably 10.0 or lower.
  • ⁇ 21> It is preferably for naturally derived fibers, more preferably for fibers collected from natural animals and plants, or for fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk scraps or silk fibroin, and further. It is preferably for fibers collected from natural animals and plants other than human hair fibers, or for fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk dust or silk fibroin, and even more preferably. Any of ⁇ 1> to ⁇ 20>, which is a treatment agent for regenerated protein fibers selected from regenerated collagen fibers made from collagen and regenerated silk fibers made from silk fibroin, and more preferably for regenerated collagen fibers.
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • the heating temperature is preferably 85 ° C. or higher, more preferably 88 ° C. or higher, still more preferably 90 ° C. or higher, and preferably 120 ° C. or lower, more preferably 115 ° C. or lower, still more preferably 110 ° C. or lower.
  • ⁇ 24> The method for producing a fiber treatment agent according to ⁇ 22> or ⁇ 23>, wherein the heating time is preferably 1 minute or more, more preferably 5 minutes or more, preferably 20 minutes or less, and more preferably 15 minutes or less. ..
  • the pH at the time of heating is preferably 7.0 or more, more preferably 8.0 or more, still more preferably 9.0 or more, and preferably 13.0 or less, more preferably 12.0 or less, still more preferably 11.0 or less, ⁇ 22> to The method for producing a fiber treatment agent according to any one of ⁇ 24>.
  • the fiber treatment agent is preferably for naturally derived fibers, more preferably for fibers collected from natural animals and plants, or artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk dust or silk fibroin.
  • fibers more preferably for fibers collected from natural animals and plants other than human hair fibers, or for fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk dust or silk fibroin.
  • a treatment agent for regenerated protein fibers selected from regenerated collagen fibers made from collagen as a raw material and regenerated silk fibers made from silk fibroin, and even more preferably a treatment agent for regenerated collagen fibers.
  • the method for producing a fiber treatment agent according to any one of ⁇ 25>.
  • a fiber treatment method including the following step (i). (i) A step of immersing the fiber in the fiber treatment agent according to any one of ⁇ 1> to ⁇ 21> and treating the fiber while maintaining the turbidity of the treatment agent at 1000 NTU or less.
  • the heating time for heating the treatment agent having a turbidity of 1000 NTU or less immediately after preparation until the treatment agent exceeds the turbidity of 1000 NTU is preferably 0.2 T or more.
  • the fiber treatment method according to ⁇ 28>, wherein the fiber treatment method is preferably 0.3 T or more, more preferably 0.4 T or more, preferably 0.8 T or less, more preferably 0.7 T or less, still more preferably 0.6 T or less.
  • the amount of the fiber treatment agent in which the fiber is immersed in the step (i) is preferably 2 or more, more preferably 3 or more, still more preferably 3 or more in terms of the bath ratio to the mass of the fiber (mass of the fiber treatment agent / mass of the fiber). Any one of ⁇ 27> to ⁇ 29>, which is 5 or more, more preferably 10 or more, still more preferably 20 or more, still preferably 500 or less, more preferably 250 or less, still more preferably 100 or less.
  • the temperature of the fiber treatment agent in the step (i) is preferably 20 ° C. or higher, more preferably 35 ° C. or higher, further preferably 45 ° C. or higher, and preferably less than 100 ° C., more preferably 80 ° C. or lower, further.
  • the heating time in step (i) for heating the treatment agent having a turbidity of 1000 NTU or less immediately after preparation and the heating time until the treatment agent exceeds the turbidity of 1000 NTU is defined as T, it is preferably 0.3 T or more. Any one of ⁇ 27> to ⁇ 31>, preferably 0.4 T or more, more preferably 0.5 T or more, preferably 0.95 T or less, more preferably 0.90 T or less, still more preferably 0.85 T or less.
  • the fiber treatment method according to any one of ⁇ 27> to ⁇ 32>, wherein the following step (ii) is performed after the step (i), and the step (i) and the step (ii) are repeated two or more times. .. (ii)
  • the process of removing fibers from the treatment agent before the turbidity of the treatment agent exceeds 1000 NTU.
  • the fiber treatment method according to ⁇ 33> wherein the following step (iii) is performed after the step (ii). (iii) Rinsing process of removed fibers
  • rinsing of the step (iii) is preferably carried out using a rinsing composition containing the component (D).
  • D Organic compounds having a Hansen solubility parameter SP value of 16 MPa 1/2 or more and 40 MPa 1/2 or less (excluding organic salts and compounds having a molecular weight of 150 or less having an aldehyde group).
  • the rinsing composition contains water in addition to the component (D), and the content of the component (D) in the rinsing composition is preferably 60% by mass or more, more preferably 80% by mass or more, and even more preferably.
  • the fiber treatment method according to any one of ⁇ 27> to ⁇ 36>, wherein the following step (iv) is further performed after the steps (i) to (iii).
  • Step of immersing the fiber in a post-crosslinking agent containing components (E) and (C) E): Formaldehyde, hydrate of formaldehyde, glyoxylic acid, hydrate of glyoxylic acid, glyoxate, glyoxal , Glyoxal hydrate, glutaraldehyde, and at least one formaldehyde derivative selected from glutaraldehyde hydrate (C): water.
  • the content of the component (E) in the post-crosslinking agent is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 1% by mass or more, and preferably 60% by mass or less, more preferably.
  • the fiber treatment method according to ⁇ 37> which is 40% by mass, more preferably 20% by mass or less.
  • the temperature of the post-crosslinking agent is preferably 20 ° C. or higher, more preferably 35 ° C. or higher, still more preferably 45 ° C. or higher, and preferably less than 100 ° C., more preferably 80 ° C. or lower, still more preferably 70 ° C. or lower.
  • ⁇ 40> Preferably, after step (i) to (iii) or step (iv), a step of immersing the fiber in a surface finishing agent containing the following components (F) and (C) is further performed, ⁇ 27>.
  • Epoxyaminosilane copolymer which is a reaction product of the following compounds (a) to (d) (a) Polysiloxane having at least two oxylanyl groups or oxetanyl groups (b) Poly having at least two oxylanyl groups or oxetanyl groups Ether (c) Aminopropyltrialkoxysilane (d) A compound selected from the group consisting of the following primary and secondary amines-Primary amines: methylamine, ethylamine, propyleneamine, ethanolamine, isopropylamine, Butylamine, isobutylamine, hexylamine, dodecylamine, oleylamine, aniline, aminopropyltrimethylsilane, aminopropyltriethylsilane, aminomorpholin, aminopropyldiethylamine, benzylamine, naphthylamine, 3-amino-9-ethylcarbazole, 1-
  • the content of the component (F) in the surface finishing agent is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.10% by mass or more, still more preferably 0.20% by mass or more, and more preferably.
  • the fibers to be treated are preferably naturally derived fibers, more preferably fibers collected from natural animals and plants, or artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk dust or silk fibroin. Fibers, more preferably fibers collected from natural animals and plants other than human hair fibers, or fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk scraps or silk fibroin, even more preferably. Is described in any one of ⁇ 27> to ⁇ 42>, which is a regenerated protein fiber selected from a regenerated collagen fiber made from collagen and a regenerated silk fiber made from silk fibroin, and more preferably a regenerated collagen fiber. Fiber treatment method.
  • a method for producing a fiber for a headdress product which comprises a step of treating the fiber by the fiber treatment method according to any one of ⁇ 27> to ⁇ 43>.
  • a method for manufacturing a headdress product which comprises a step of treating the fiber by the fiber treatment method according to any one of ⁇ 27> to ⁇ 43>.
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • a headdress product whose constituent is a fiber containing a condensate produced from the components (A) and (B).
  • R 1 to R 3 may be the same or different, and may be a hydrogen atom, a hydroxymethylamino group, an amino group, a hydroxyl group, a halogen atom, a phenyl group, a linear or branched chain having 1 or more and 6 or less carbon atoms.
  • An alkyl group or an alkenyl group, or a linear or branched alkoxy group or an alkenyloxy group having 1 or more and 6 or less carbon atoms is shown.
  • a fiber treatment agent containing the following components (A) to (C).
  • the fiber treatment agent according to ⁇ 45> which further contains the following component (D).
  • D One or more selected from diethylene glycol, triethylene glycol, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and DMDM hydantoin 15-45% by mass
  • ⁇ 50> It is preferably for naturally derived fibers, more preferably for fibers collected from natural animals and plants, or for fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk scraps or silk fibroin, and further. It is preferably for fibers collected from natural animals and plants other than human hair fibers, or for fibers artificially produced from keratin, collagen, casein, soybeans, peanuts, corn, silk dust or silk fibroin, and even more preferably.
  • the treatment agent for a regenerated protein fiber selected from a regenerated collagen fiber made from collagen and a regenerated silk fiber made from silk fibroin, and more preferably a treatment agent for the regenerated collagen fiber, according to ⁇ 48> or ⁇ 49>. Fiber treatment agent.
  • a fiber treatment agent kit comprising the fiber treatment agent according to any one of ⁇ 48> to ⁇ 50> and a post-crosslinking agent containing the components (E) and (C) and having a pH of 1.0 to 4.5.
  • E Glyoxylic acid or formaldehyde 1-20% by mass
  • C Remaining amount of water
  • the fiber treatment agent kit according to ⁇ 51> further comprising a surface finishing agent containing the components (F) and (C).
  • a surface finishing agent containing the components (F) and (C).
  • a fiber treatment agent kit containing the fiber treatment agent according to any one of ⁇ 48> to ⁇ 50> and a surface finish agent containing the components (F) and (C).
  • F Polysilicone-29 0.1-15% by mass
  • C Remaining amount of water
  • Examples 1-12, Comparative Examples 1-6 Using the compositions of the formulations shown in Table 1, the regenerated collagen fibers were treated according to the following method, and various evaluations were performed.
  • the pH of each composition was measured by measuring the prepared composition at room temperature (25 ° C.) as it was with a pH meter (F-52, manufactured by HORIBA).
  • the turbidity of the composition is such that the fiber treatment agent is used as it is at room temperature (25 ° C).
  • the measurement was carried out in a measurement cell ( ⁇ 25 x 60 mm borosilicate glass) of a radiation diode (850 nm) / detector: crystalline silicon solar cell module).
  • Regenerated collagen fiber manufactured by Kaneka Corporation was purchased in the form of a commercially available extension product, and the fiber was cut from the fiber and divided into hair bundles for evaluation.
  • the extension product has a notation of using 100% Ultima as the fiber type, and the one with a color count of 3 brown and a straight shape was used.
  • the container containing the hair bundle was removed from the water bath and returned to room temperature.
  • a warm air dryer Nobby White NB3000 manufactured by Tescom
  • a fiber treatment agent with a predetermined bath ratio (1.5 g for Comparative Example 4 and 1.0 g for Comparative Example 5) is applied to a hair bundle of 0.5 g of regenerated collagen fiber (*) and a length of 22 cm, and the hair bundle is well blended and then sealed.
  • the container was placed in an oven set at 65 ° C. (forced convection dryer with stainless steel window; SOFW-450 manufactured by AS ONE), and heated for a predetermined time.
  • Regenerated collagen fiber manufactured by Kaneka Corporation was purchased in the form of a commercially available extension product, and the fiber was cut from the fiber and divided into hair bundles for evaluation.
  • the extension product has a notation of using 100% Ultima as the fiber type, and the one with a color count of 3 brown and a straight shape was used.
  • the container containing the hair bundle was removed from the oven and returned to room temperature. 3.
  • the hair bundle was covered with a turbid and opaque white precipitate in all of Comparative Examples 4 and 5.
  • whisk with shampoo for evaluation for 60 seconds
  • rinse with tap water at 30 ° C for 30 seconds drain lightly with a towel, and then warm the hair bundles. It was dried while combing with a wind dryer (Nobby White NB3000 manufactured by Tescom). At this point, the tufts remained straight.
  • the average breaking elongation (B%) of the hair bundle after treatment is based on the average breaking elongation (A%) at the time of fiber tension in the as-is (untreated) state cut from the commercial product.
  • the degree of increase (C%) from the untreated state is described in the table as "the rate of increase in the average elongation at break during fiber tension [%]".
  • C (%) B (%) -A (%)
  • the fiber piece was set in the "MTT690 automatic fiber tensile tester" manufactured by DIA-STRON limited, and automatic measurement was started, and the breaking load when the fiber was stretched in a wet state was obtained.
  • the average breaking load (W 0 (gf)) of the hair bundle after treatment (W 1 (gf)) is based on the average breaking load (W 0 (gf)) when the fiber is pulled as it is cut from the commercial product (untreated).
  • the extent to which ()) increased from the untreated state (Y (gf)) is described in the table as "increase in average breaking load during fiber tension [gf]".
  • Y (gf) W 1 (gf) -W 0 (gf)
  • ⁇ Thermal shape memory ability> The evaluation of the thermal shape memory ability was performed using the hair bundle immediately after being treated by the above ⁇ treatment method>. When the value of the result of "I: shape addition (curl)" was 5% or less, it was considered that there was no effect, and the subsequent processing and evaluation were not performed.
  • the hair bundle wrapped around the rod was immersed in a water bath (manufacturer: Toyo Engineering Works, Ltd./model number: TBS221FA) at 60 ° C. and heated for 1 minute. 3. 3. The hair bundle was removed from the water bath, immersed in water at 25 ° C. for 1 minute, and returned to room temperature. 4. After removing the hair bundle from the rod and passing the comb three times, I hung it and took a picture from the side.
  • a water bath manufactured by Toyo Engineering Works, Ltd./model number: TBS221FA
  • ⁇ II Reshape (straight) 1.
  • the hair bundle evaluated in I was entangled through a comb, and then slid 6 times at a speed of 5 cm / sec with a flat iron (manufactured by Miki Denki Sangyo Co., Ltd./model number: AHI-938) having an actual measurement temperature of 140 ° C. 2.
  • 3. 3 The hair was dried while being vibrated so that the natural shape of the hair appeared (without using a dryer), passed through a comb, and then hung and visually observed from the side.
  • the untreated hair bundle length was defined as L 0 (22 cm), the treated hair bundle length was L, and the straightening rate (ST) (%) obtained according to the following equation was defined as the degree of achievement of straightening.
  • ST 100%, the hair bundle is completely straightened.
  • ST [1- (L 0 -L) / L 0 ] x 100
  • ⁇ III Reshape addition (curl)> 1.
  • 1. After wetting the hair bundle evaluated in II with tap water at 30 ° C. for 30 seconds, the wet hair bundle was wrapped around a plastic rod having a diameter of 14 mm and fixed with a clip. 2.
  • the hair bundle wrapped around the rod was immersed in a water bath (manufacturer: Toyo Engineering Works, Ltd./model number: TBS221FA) at 60 ° C. and heated for 1 minute. 3.
  • the hair bundle was removed from the water bath, immersed in water at 25 ° C. for 1 minute, and returned to room temperature. 4. After removing the hair bundle from the rod and passing the comb three times, I hung it and took a picture from the side.
  • Example 13 post-crosslinking treatment
  • the regenerated collagen fibers treated in Example 5 were treated with the post-treatment agents shown in Table 2 and various evaluations were performed.
  • 1. Immerse a 22 cm long hair bundle of 0.5 g of regenerated collagen fiber in a container containing 40 g of post-crosslinking agent, seal the mouth of the container, and use a water bath at a predetermined temperature for each container (manufacturer: Toyo Seisakusho Co., Ltd./model number:: It was immersed in TBS221FA) and heated for a predetermined time.
  • the container containing the hair bundle was removed from the water bath and returned to room temperature. 3.
  • Example 14 (Surface finish treatment) The regenerated collagen fibers treated in Example 5 were treated with the surface finishing agents shown in Table 3 and various evaluations were performed.
  • the hair bundle was immersed in a container containing 40 g of a surface finishing agent and allowed to stand at room temperature for 30 minutes. 2.
  • the hair bundle was taken out of the container and dehydrated for 5 minutes with a household centrifugal dehydrator (ultra-high-speed dehydrator Powerful Spin Dry APD-6.0 / manufactured by Aluminus) (spin coating method).
  • 3. The hair bundle was removed from the dehydrator and heated in an oven set at 60 ° C. (forced convection dryer with stainless steel window; SOFW-450 manufactured by AS ONE Corporation) for 3 hours. 4.
  • the tresses were removed from the oven and returned to room temperature. 5.
  • the hair bundle was rinsed with running water at 30 ° C. for 30 seconds, drained lightly with a towel, and then dried while combing with a warm air dryer (Nobby White NB3000 manufactured by Tescom).
  • Examples 15-18 The regenerated collagen fiber hair bundles treated in Examples 1 and 10 were slid 30 times at a speed of 5 cm / sec with a flat iron (manufactured by Miki Denki Sangyo Co., Ltd./model number: AHI-938) having an actual measurement temperature of 160 ° C. After that, various evaluations were performed (Examples 15 and 17). Further, in order to apply tension to the hair bundle after the ironing treatment to the extent that each fiber constituting the hair bundle is stretched in the range of 0.1 to 0.5% on average, both ends of the hair bundle are sandwiched between hairpins and pulled. In this state, the hairpin was fixed to the wall of the water bath with tape and allowed to stand in water at 40 ° C. for 1 hour, and then the hair bundles dried by a dryer were also evaluated in various ways (Examples 16 and 18).

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WO2019159867A1 (ja) * 2018-02-15 2019-08-22 花王株式会社 人毛繊維処理剤
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See also references of EP4268651A4

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