WO2020195873A1 - Composition de silicone et agent de traitement de fibres - Google Patents

Composition de silicone et agent de traitement de fibres Download PDF

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Publication number
WO2020195873A1
WO2020195873A1 PCT/JP2020/010731 JP2020010731W WO2020195873A1 WO 2020195873 A1 WO2020195873 A1 WO 2020195873A1 JP 2020010731 W JP2020010731 W JP 2020010731W WO 2020195873 A1 WO2020195873 A1 WO 2020195873A1
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group
mass
silicone composition
parts
carbon atoms
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PCT/JP2020/010731
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English (en)
Japanese (ja)
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優太 濱嶋
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信越化学工業株式会社
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Publication of WO2020195873A1 publication Critical patent/WO2020195873A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
    • D06M13/217—Polyoxyalkyleneglycol ethers with a terminal carboxyl group; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • 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
    • 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
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences

Definitions

  • the present invention relates to a silicone composition. More specifically, the present invention relates to a silicone composition capable of imparting high flexibility and water absorption to fibers, and a fiber treatment agent containing the silicone composition.
  • organopolysiloxanes such as dimethylpolysiloxane, epoxy group-containing polysiloxane, and aminoalkyl group-containing polysiloxane have been widely used as treatment agents for imparting flexibility and smoothness to various fibers or textile products.
  • aminoalkyl group-containing organopolysiloxanes that can impart particularly good flexibility to various fibers or textile products are often used.
  • 54-43614 Japanese Patent Laid-Open No. 57-43673, JP-A-60-185879, JP-A-60-185880, JP-A64-61576, etc. are widely used because of their excellent flexibility. ing.
  • fibers treated with a treatment agent containing polysiloxane as a main component show water repellency. Even fibers that originally have water absorbency exhibit hydrophobicity after being treated with polysiloxane, and when used for clothing, for example, there is a drawback that the sweat-absorbing action during sweating is almost lost.
  • studies have been made to impart both flexibility and water absorption to the fibers. For example, a technique has been proposed in which an aminoalkyl group and a polyoxyalkylene group are contained in the same polysiloxane molecule. As a result, the water absorption is improved, but there is a drawback that the flexibility, smoothness, etc. are significantly lowered by containing the polyoxyalkylene group.
  • An object of the present invention is to provide a silicone composition that exhibits excellent flexibility and water absorption on the treated fiber surface in view of the above-mentioned problems of the prior art. Furthermore, an object of the present invention is to provide a silicone composition having excellent washing resistance and not impairing the flexibility of fibers even after washing, and a fiber treatment agent containing the silicone composition.
  • the present invention provides the following silicone compositions and fiber treatment agents.
  • 1. The following formula (1) (In the formula, R 1 is an unsubstituted or substituted divalent hydrocarbon group having 1 to 8 carbon atoms, a is a number of 0 to 4, and R 2 is a hydrogen atom or 1 to 1 carbon atoms independently of each other. 10 unsubstituted or substituted monovalent hydrocarbon group or acyl group.) Organopolysiloxane, which has a group bonded to a silicon atom and has a viscosity at 25 ° C.
  • R 3 is an alkyl group having 1 to 20 carbon atoms
  • b is a number of 1 to 30
  • X is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid.
  • R 4 is a phenyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a hydroxyl group independently of each other
  • R 5 is an independent formula ⁇ C e H 2e O ( C 2 H 4 O) f (C 3 H 6 O) g
  • R 7 is a hydrogen atom and has 1 to 6 carbon atoms.
  • composition of the present invention can impart excellent flexibility and water absorption to fibers.
  • the composition of the present invention is excellent in washing resistance, and the fiber treated with the composition of the present invention can maintain good flexibility even after washing.
  • R 1 is an unsubstituted or substituted divalent hydrocarbon group having 1 to 8 carbon atoms
  • a is a number of 0 to 4
  • R 2 is a hydrogen atom or 1 to 1 carbon atoms independently of each other. 10 unsubstituted or substituted monovalent hydrocarbon group or acyl group.
  • It is an organopolysiloxane represented by, which has a group bonded to a silicon atom and has a viscosity at 25 ° C. of 20 to 20,000 mPa ⁇ s.
  • the component (A) may be used alone or in combination of two or more.
  • the organopolysiloxane may have a linear structure, a branched structure, or a cyclic structure, but is preferably linear.
  • the group represented by the above formula (1) is bonded to the silicon atom of the polysiloxane skeleton, and may be present at one end, both ends, or a side chain in the molecule, and one end. Only, only both ends, only side chains, or may be attached to each.
  • the number of groups represented by the above formula (1) is at least one in the molecule, and it is preferable to have two or more groups.
  • R 1 is an unsubstituted or substituted divalent hydrocarbon group having 1 to 8 carbon atoms.
  • the divalent hydrocarbon group include alkylene groups such as methylene group, ethylene group, propylene group and butylene group, and propylene group is preferable.
  • a is an integer of 0 to 4, preferably 1 or 2.
  • R 2 is a hydrogen atom independently of each other, or a monovalent hydrocarbon group or acyl group having 1 to 10 carbon atoms.
  • Examples of the unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms include a linear alkyl group, a branched chain alkyl group, a cyclic alkyl group, an alkenyl group, an aryl group and an aralkyl group.
  • Examples of the acyl group having 1 to 10 carbon atoms include an acetyl group and the like. Of the groups represented by R 2 , 33% or more are preferably hydrogen atoms, and 50% or more are preferably hydrogen atoms.
  • the component (A) has a viscosity at 25 ° C. of 20 to 20,000 mPa ⁇ s, preferably 40 to 15,000 mPa ⁇ s, and more preferably 40 to 10,000 mPa ⁇ s.
  • the viscosity is a value measured by a BM type rotational viscometer.
  • Examples of the component (A) include organopolysiloxanes represented by the following general formulas (4) to (6).
  • the bonding order of each siloxane unit is not limited to the following.
  • R 9 is independent of each other, an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms
  • R 10 is independent of each other, -OY (Y is a hydrogen atom, or 1 to 12 carbon atoms. It is an unsubstituted or substituted monovalent hydrocarbon group.)
  • R 8 is R 9 or R 10 independently of each other.
  • R 11 is independent of each other and has the following equation (1) (In the formula, R 1 is an unsubstituted or substituted divalent hydrocarbon group having 1 to 8 carbon atoms, a is a number of 0 to 4, and R 2 is a hydrogen atom or 1 to 1 carbon atoms independently of each other. 10 unsubstituted or substituted monovalent hydrocarbon group or acyl group.) It is a group indicated by. h is an integer of 5 to 1,000, j is an integer of 0 to 3 independently of each other, k is 0 or 1 independently of each other, and j + k is 0 to 3 at each end. However, equations (4) and (6) are selected to have R 11 at at least one end. ]
  • the unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms defined by R 8 , Y, and R 9 is preferably an unsubstituted or substituted monovalent hydrocarbon group having 1 to 8 carbon atoms.
  • alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group and eicosyl group.
  • cycloalkyl group such as cyclopentyl group and cyclohexyl group
  • aryl group such as phenyl group and tolyl group
  • alkenyl group such as vinyl group and allyl group, and one of hydrogen atoms bonded to carbon atom of these groups.
  • alkyl halide group and an alkenyl halide group in which a part or the whole is substituted with a halogen atom such as chlorine or fluorine.
  • the methyl group is industrially preferable.
  • Y in the group represented by -OY defined by R 8 and R 10 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms.
  • the -Y group include an alkyl group such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group
  • the -OY group includes a hydroxyl group and a methoxy group.
  • Ethoxy group is preferred.
  • H is an integer of 5 to 1,000, preferably an integer of 10 to 800. If h is less than the above lower limit value, the effect of imparting flexibility or smoothness to the fiber may be insufficient. Further, when h exceeds the above upper limit value, the organopolysiloxane becomes highly viscous, which may make handling and emulsification difficult.
  • Equation (4) and (6) are selected to have R 11 at at least one end.
  • the organopolysiloxane represented by the above formulas (4) to (6) preferably has one or more R 10s in the molecule, j is preferably 1 or 2, more preferably 1, and j at both ends.
  • k at both ends is 1.
  • organopolysiloxane represented by the above formulas (4) to (6) include the following.
  • the organopolysiloxane represented by the above formulas (4) to (6) can be easily obtained by a known synthetic method.
  • a catalyst such as alkali metal hydroxide or tetramethylammonium hydroxide
  • cyclic siloxane such as octamethylcyclotetrasiloxane and 3-aminopropyldiethoxymethylsilane or N- (2-aminoethyl) -3.
  • -It is obtained by an equilibrium reaction with aminopropyldimethoxymethylsilane, a hydrolyzate thereof, and a compound selected from hexamethyldisiloxane or the like as another raw material.
  • both terminal hydroxy group-blocking dimethylpolysiloxane and 3-aminopropyldimethoxymethylsilane or N- (2-aminoethyl) -3-aminopropyldimethoxy It is obtained by demethanolic reaction with methylsilane.
  • the component (B) is the following formula (2) (In the formula, R 3 is an alkyl group having 1 to 20 carbon atoms, b is a number of 1 to 30, and X is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid.) It is an alkyl ether carboxylic acid represented by or a salt thereof.
  • the component (B) may be used alone or in combination of two or more.
  • R 3 is an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 15 carbon atoms is more preferable. Further, the alkyl chain of R 3 may be either a straight chain or a branched chain, and may contain one kind or two or more kinds of alkyl groups.
  • b indicates the number of moles of ethylene oxide added. b is a number of 1 to 30, preferably 3 to 20.
  • Examples of X include hydrogen atom, alkali metal such as sodium and potassium, alkaline earth metal such as calcium and magnesium, organic ammonium derived from alkanolamine such as ammonium, monoethanolamine, diethanolamine and triethanolamine, and L-arginine. Examples include basic amino acids.
  • X is preferably a hydrogen atom, an alkali metal, or an alkaline earth metal, and more preferably a hydrogen atom or an alkali metal.
  • alkyl ether carboxylic acid (B) or a salt thereof examples include polyoxyethylene lauryl ether acetate, polyoxyethylene lauryl ether sodium acetate, polyoxyethylene lauryl ether potassium acetate, polyoxyethylene lauryl ether calcium acetate, and polyoxyethylene lauryl.
  • examples thereof include ether magnesium acetate, polyoxyethylene lauryl ether ammonium acetate, polyoxyethylene dodecyl ether acetate, polyoxyethylene dodecyl ether sodium acetate, polyoxyethylene tridecyl ether acetate, polyoxyethylene tridecyl ether sodium acetate and the like.
  • (B) alkyl ether carboxylic acid or a salt thereof a commercially available product can be used.
  • examples of commercially available alkyl ether carboxylic acids or salts thereof include Kao Akipo RLM-45, Kao Akipo RLM-100, Kao Akipo RLM-45NV (manufactured by Kao Chemical Co., Ltd.), Beaulite LCA-30D, Beaulite ECA, (Sanyo Kasei). (Made by the company) and the like.
  • the action and effect of the component (B) is not limited, but it is considered that the combined use of the component (A) and the component (B) results in a highly hydrophilic silicone composition. It is considered that when the silicone composition of the present invention is treated on a cloth, it is possible to impart very excellent water absorption to the cloth in addition to the flexibility of the silicone.
  • the blending amount of the component (B) is 10 to 200 parts by mass, preferably 20 to 180 parts by mass, and more preferably 30 to 150 parts by mass with respect to 100 parts by mass of the component (A). If the blending amount of the component (B) is less than the above lower limit value, the effect of imparting water absorption to the fiber is insufficient, and if the amount of the component (B) exceeds the above upper limit value, the effect of imparting flexibility to the fiber is insufficient. is there.
  • the silicone composition of the present invention preferably contains the component (C) from the viewpoint of improving flexibility after washing.
  • the component (C) is composed of the following general formula (3).
  • R 4 is a phenyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a hydroxyl group independently of each other
  • R 5 is an independent formula ⁇ C e H 2e O ( C 2 H 4 O) f (C 3 H 6 O) g
  • R 7 is an organic group represented by R 7
  • R 6 is R 4 or R 5 independently of each other
  • R 7 is a hydrogen atom and has 1 to 6 carbon atoms.
  • c is an integer of 0 to 100
  • d is an integer of 0 to 100
  • c + d is an integer of 0 to 200
  • e is an integer of 2 to 5
  • f Is an integer from 1 to 40
  • g is an integer from 0 to 40.
  • R 6 is R 5.
  • It is a polyether-modified silicone represented by.
  • the component (C) can be used alone or in combination of two or more.
  • component (C) includes the following.
  • the blending amount is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the component (A), and more preferably 2 to 30 parts by mass with respect to 100 parts by mass of the component (A). To 20 parts by mass is more preferable.
  • the blending amount is preferably 10 to 10,000 parts by mass, more preferably 20 to 6,000 parts by mass, based on 100 parts by mass of the silicone composition.
  • the silicone composition of the present invention can be suitably used as a fiber treatment agent.
  • the above silicone composition is dissolved in an organic solvent, dispersed in water, or emulsified using an emulsifier such as a nonionic, anionic, cationic or amphoteric surfactant. It is preferable to use a product.
  • solvents can be used for the fiber treatment agent of the present invention, if necessary.
  • the solvent include ether solvents such as dibutyl ether, dioxane and THF, ketone solvents such as acetone and MEK, methanol, ethanol, 2-propanol, n-butanol, sec-butanol and 2-ethyl-1-hexanol.
  • the blending amount is not particularly limited, but is preferably 2,000 to 200,000 parts by mass, more preferably 10,000 to 100,000 parts by mass with respect to 100 parts by mass of the silicone composition. ..
  • the emulsifier when the fiber treatment agent of the present invention is made into an emulsion is not particularly limited.
  • a nonionic (nonionic) surfactant ethoxylated higher alcohol, ethoxylated alkylphenol, polyhydric alcohol fatty acid, etc.
  • examples thereof include esters, ethoxylated polyhydric alcohol fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid amides, sorbitol, sorbitan fatty acid esters, ethoxylated sorbitan fatty acid esters, sucrose fatty acid esters and the like.
  • the HLB is preferably in the range of 5 to 20, more preferably in the range of 10 to 16.
  • anionic surfactants include higher alcohol sulfates, alkylphenyl ether sulfates, alkylbenzene sulfonates, higher alcohol phosphates, ethoxylated higher alcohol sulfates, and ethoxylated alkylphenyl ether sulfates. Examples include salts and ethoxylated higher alcohol phosphates. Examples of cationic surfactants include alkyltrimethylammonium chloride, alkylamine hydrochloride, coconutamine acetate, alkylamine acetate, alkylbenzenedimethylammonium chloride and the like.
  • amphoteric surfactants include N-acylamidepropyl-N, N-dimethylammoniobetaines, N-acylamidepropyl-N, N'-dimethyl-N'- ⁇ -hydroxypropylammoniobetaines. Etc. are exemplified.
  • the blending amount is preferably 0.5 to 50 parts by mass and more preferably 5 to 30 parts by mass with respect to 100 parts by mass of the silicone composition.
  • the amount of water used for emulsification may be such that the pure content concentration of (A) organopolysiloxane is 10 to 80% by mass, preferably 20 to 70% by mass.
  • the emulsion can be obtained by a conventionally known method.
  • the above silicone composition and a surfactant are mixed, and the emulsion is mixed with a homomixer, a homogenizer, a colloid mill, a line mixer, a universal mixer (trade name), and an ultramixer (trade name). It may be emulsified with an emulsifying machine such as a product name), a planetary mixer (product name), a combination mix (product name), or a three-roll mixer.
  • the fiber treatment agent of the present invention further includes a wrinkle preventive agent, a flame retardant, an antistatic agent, a heat resistant agent and other fiber chemicals, an antioxidant, an ultraviolet absorber, and the like, as long as the object of the present invention is not impaired.
  • Ingredients such as pigments, metal powder pigments, rheology control agents, curing accelerators, deodorants, and antibacterial agents can also be added.
  • the fiber treatment agent of the present invention when attached to the fiber, it can be attached to the fiber by dipping, spraying, roll coating or the like.
  • the amount of adhesion varies depending on the type of fiber and is not particularly limited, but the total amount of adhesion of the components (A) and (B) in the silicone composition blended in the fiber treatment agent is in the range of 0.01 to 10% by mass. Is preferable.
  • it may be dried by blowing hot air or in a heating furnace. Although it depends on the type of fiber, drying may be performed at 100 to 180 ° C. for 30 seconds to 5 minutes.
  • the fibers or textile products that can be treated with the fiber treatment agent of the present invention are not particularly limited, and natural fibers such as cotton, silk, linen, wool, angora and mohair, polyester, polyethylene, polypropylene, nylon, acrylic and spandex are not particularly limited. It is also effective for synthetic fibers such as, and blended fibers that combine these. Further, the form and shape are not limited, and the fiber of the present invention is not limited to the shape of raw materials such as staples, filaments, tows, threads, etc. It becomes a treatable target of the treatment agent.
  • the silicone composition of the present invention has various uses other than fiber treatment applications, such as paints, adhesives, sealants, inks, paper impregnants, surface treatments, cosmetics, and the like. Can be used for. At this time, an additive can be used if necessary. Additives include, for example, anti-wrinkle agents, flame retardants, antistatic agents, heat-resistant agents and other textile agents, antioxidants, ultraviolet absorbers, pigments, metal powder pigments, rheology control agents, curing accelerators, deodorants. Examples include agents and antibacterial agents. These additives may be used alone or in combination of two or more.
  • Example 1 100 parts by mass of organopolysiloxane (amine equivalent: 830 g / mol, viscosity 70 mPa ⁇ s) represented by the following formula (A-1) and Kao Akipo RLM-45 (polyoxyethylene (4.5) lauryl ether acetic acid, solid content)
  • a silicone composition (1) was prepared by mixing 56 parts by mass (92% by mass, manufactured by Kao Co., Ltd.) (the pure equivalent amount is shown in the table, the same applies hereinafter) at room temperature (25 ° C.) for 30 minutes.
  • Example 2 100 parts by mass of organopolysiloxane represented by the above formula (A-1) and 90 parts by mass of Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Corporation) at room temperature ( The mixture was mixed at 25 ° C. for 30 minutes to prepare a silicone composition (2).
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Corporation
  • Example 3 100 parts by mass of organopolysiloxane represented by the above formula (A-1) and 330 parts by mass of Kao Akipo RLM-100 NV (polyoxyethylene (10) sodium lauryl ether acetate, solid content 24% by mass, manufactured by Kao Corporation) at room temperature.
  • the silicone composition (3) was prepared by mixing at (25 ° C.) for 30 minutes.
  • Example 4 100 parts by mass of organopolysiloxane represented by the following formula (A-2) (amine equivalent: 2300 g / mol, viscosity 70 mPa ⁇ s) and Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass) %, Manufactured by Kao Co., Ltd.) 180 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (4).
  • A-2 amine equivalent: 2300 g / mol, viscosity 70 mPa ⁇ s
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass
  • Manufactured by Kao Co., Ltd. 180 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (4).
  • Example 5 100 parts by mass of organopolysiloxane represented by the following formula (A-3) (amine equivalent: 290 g / mol, viscosity 240 mPa ⁇ s) and Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass) %, Manufactured by Kao Co., Ltd.) 130 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (5).
  • A-3 amine equivalent: 290 g / mol, viscosity 240 mPa ⁇ s
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass
  • Manufactured by Kao Co., Ltd. 130 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (5).
  • Example 6 100 parts by mass of organopolysiloxane represented by the following formula (A-4) (amine equivalent: 300 g / mol, viscosity 420 mPa ⁇ s) and Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass) %, Manufactured by Kao Co., Ltd.) 130 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (6).
  • A-4 amine equivalent: 300 g / mol, viscosity 420 mPa ⁇ s
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89 mass
  • Manufactured by Kao Co., Ltd. 130 parts by mass was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (6).
  • Example 7 100 parts by mass of organopolysiloxane represented by the above formula (A-1), 100 parts by mass of Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.) and the following formula ( 20 parts by mass of the polyether-modified silicone shown in C-1) was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (7).
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.
  • Example 8 100 parts by mass of organopolysiloxane represented by the above formula (A-4), 100 parts by mass of Kao Akipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.) and the above formula ( 20 parts by mass of the polyether-modified silicone shown in C-1) was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (8).
  • Kao Akipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.
  • Example 9 100 parts by mass of organopolysiloxane represented by the above formula (A-1), 100 parts by mass of Kaoakipo RLM-100 (polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.) and the following formula (C) 20 parts by mass of the polyether-modified silicone shown in -2) was mixed at room temperature (25 ° C.) for 30 minutes to prepare a silicone composition (9).
  • Kaoakipo RLM-100 polyoxyethylene (10) lauryl ether acetic acid, solid content 89% by mass, manufactured by Kao Co., Ltd.
  • C 20 parts by mass of the polyether-modified silicone shown in -2
  • Ion-exchanged water was added to the water-absorbent silicone composition, and the mixture was stirred and diluted to a solid content of 2% by mass to prepare a test solution.
  • a polyester / cotton broad cloth (65% / 35%, manufactured by Tanito Shoten Co., Ltd.) was immersed in the test solution for 1 minute, then squeezed using a roll under the condition of a drawing ratio of 100%, and heat-treated at 150 ° C. for 2 minutes. Then, one drop (25 ⁇ L) of tap water was dropped on the treated cloth with a dropper, and the time (seconds) until the water drop was completely absorbed by the cloth was measured (water absorption before washing).
  • the residual amount of silicone on the fiber surface after one washing was measured with a fluorescent X-ray analyzer (manufactured by Rigaku), and the residual ratio (mass%) was calculated by comparing with the case where no washing was performed. A passing rate of 50% or more is considered acceptable.
  • the silicone composition of the present invention can impart excellent water absorption and flexibility to the fiber.
  • the silicone composition of the present invention is also excellent in washing durability and does not impair the flexibility of the fibers after washing.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne une composition de silicone qui contient (A) un organopolysiloxane ayant un groupe spécifique lié à un atome de silicium et ayant une viscosité de 20 à 20 000 mPa · s à 25 °C et (B) un acide carboxylique d'alkyléther spécifique ou un sel de celui-ci, et qui fournit une excellente flexibilité et une excellente capacité d'absorption d'eau à la surface des fibres traitées avec celui-ci.
PCT/JP2020/010731 2019-03-27 2020-03-12 Composition de silicone et agent de traitement de fibres WO2020195873A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01306682A (ja) * 1988-05-30 1989-12-11 Toray Dow Corning Silicone Co Ltd 繊維用処理剤組成物
JPH115903A (ja) * 1997-04-21 1999-01-12 Toray Dow Corning Silicone Co Ltd ポリオキシエチレンアルキルエーテル脂肪酸アミド変性オルガノポリシロキサン組成物
JPH11293297A (ja) * 1998-04-06 1999-10-26 Lion Corp 衣料用液体洗浄剤組成物
JP2008133547A (ja) * 2006-11-27 2008-06-12 Sanyo Chem Ind Ltd 弾性繊維用油剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01306682A (ja) * 1988-05-30 1989-12-11 Toray Dow Corning Silicone Co Ltd 繊維用処理剤組成物
JPH115903A (ja) * 1997-04-21 1999-01-12 Toray Dow Corning Silicone Co Ltd ポリオキシエチレンアルキルエーテル脂肪酸アミド変性オルガノポリシロキサン組成物
JPH11293297A (ja) * 1998-04-06 1999-10-26 Lion Corp 衣料用液体洗浄剤組成物
JP2008133547A (ja) * 2006-11-27 2008-06-12 Sanyo Chem Ind Ltd 弾性繊維用油剤

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