WO2008047897A1 - Agent ignifugeant ne contenant pas d'halogène et procédé destiné à ignifuger une fibre utilisant cet agent - Google Patents

Agent ignifugeant ne contenant pas d'halogène et procédé destiné à ignifuger une fibre utilisant cet agent Download PDF

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WO2008047897A1
WO2008047897A1 PCT/JP2007/070417 JP2007070417W WO2008047897A1 WO 2008047897 A1 WO2008047897 A1 WO 2008047897A1 JP 2007070417 W JP2007070417 W JP 2007070417W WO 2008047897 A1 WO2008047897 A1 WO 2008047897A1
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group
general formula
aqueous dispersion
formula
represented
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PCT/JP2007/070417
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English (en)
Japanese (ja)
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Hidehiro Arai
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Nippon Kayaku Kabushiki Kaisha
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Priority to JP2008539882A priority Critical patent/JPWO2008047897A1/ja
Publication of WO2008047897A1 publication Critical patent/WO2008047897A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32—Polyesters
    • 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
    • D06M2200/30—Flame or heat resistance, fire retardancy properties

Definitions

  • Non-halogen flameproofing agent and method for flameproofing fiber using the same
  • the present invention provides an aqueous dispersion capable of imparting a flameproof performance with excellent durability to a synthetic fiber structure, a non-halogen flameproofing agent using the aqueous dispersion, and prevention of fibers using the same.
  • the present invention relates to a flame treatment method and a flame-proofed fiber.
  • halogen compounds include brominated cycloalkanes such as 1, 2, 5, 6, 9, 10 hexapromocyclododecane (Patent Documents 1 and 2).
  • Patent Document 1 Japanese Patent Publication No.53-8840
  • Patent Document 2 JP-A-1 213474
  • Patent Document 3 Japanese Patent Laid-Open No. 10-298188
  • Patent Document 4 JP-A-10-212669
  • Patent Document 5 Japanese Patent Laid-Open No. 2001-254268
  • Patent Document 6 JP 2000-328445 Koyuki
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2004-225176
  • Patent Document 8 Japanese Unexamined Patent Publication No. 2006-70417
  • a flameproofing agent and a flameproofing processing method capable of imparting durable and excellent flameproofing performance to conventional fibers, in particular, blended fibers of CDP fibers and polyester fibers.
  • phosphine oxide represented by general formula (1) phosphine represented by general formula (2)
  • phosphite represented by general formula (3) An aqueous dispersion containing a phosphorus compound and a surfactant.
  • R R and R are each independently a (C1 C8) alkyl group or a hydroxyl group
  • R 1, R 2 and R are each independently a hydroxyl group, amino group, cyan group,
  • Aryl optionally substituted by a syl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group. Indicates a group. )
  • R 1, R 2 and R are each independently a hydroxyl group, amino group, cyan group,
  • Aryl optionally substituted by a syl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group. Indicates a group. )
  • R 1, R 2 and R are each independently a hydroxyl group, amino group, cyan group,
  • Phosphine oxide represented by general formula (1) Phosphine oxide represented by general formula (1), phosphine represented by general formula (2), phosphite represented by general formula (3) and phosphoric acid represented by general formula (4)
  • the surfactant is contained in the amount of the phosphorus compound relative to the amount of the phosphorus compound, the surfactant is contained in an amount of 5 to 200% by weight based on the total amount of the phosphorus compound and the ultraviolet absorber.
  • composition comprising a seed to three phosphorus compounds and a surfactant.
  • Polyester fiber strength The flameproofing agent according to 16) above, which is a cation dyeable polyester fiber or a blended fiber containing a cation dyeable polyester fiber.
  • Fibers in particular cationic dyeable polyester fibers or cationic dyeable polyester fibers, and other polyester fibers can be obtained by using a flameproofing agent using an aqueous dispersion containing the specific phosphorus compound of the present invention and a surfactant. Durable and high-performance flameproofing can be applied to the blended fiber.
  • the aqueous dispersion of the present invention is selected from the group consisting of the phosphine oxide represented by the general formula (1), the phosphine represented by the general formula (2), and the phosphite represented by the general formula (3).
  • a phosphate represented by the general formula (4) may be used.
  • an aqueous dispersion containing a compound and a surfactant, a phosphine oxide represented by the above general formula (1), a phosphine represented by the general formula (2), and a phosphine represented by the general formula (3) is preferred.
  • An aqueous dispersion containing a phosphorous ester represented by the general formula (4) and a surfactant as the phosphorous compound and a phosphorous compound selected from the group consisting of phytes is preferred.
  • R 1, R 4, R 3, R 4 in the general formula (4) examples include (CI C8) linear or branched alkyl group and (C3-C8) cyclic alkyl group.
  • CI C8 linear or branched alkyl group examples include (CI C8) linear or branched alkyl group and (C3-C8) cyclic alkyl group.
  • Examples of the (C1 C4) alkyl group include a methyl group, an ethyl group, an n propyl group, an isopropyl group, an n butyl group, an isobutyl group, and a t butyl group.
  • Examples of the di (C14) alkylamino group include N, N dimethylamino group, N, N jetylamino group, N, N di-n-propylamino group, N, N diisopropylamino group, N, N di-n-butylamino group.
  • N N diisobutylamino group, N, N di-t-butylamino group, N-methyl, N-ethylamino group, N-methyl, N-n-propylamino group, N-ethyl, N-isopropylamino group, N-isopropyl, N — N-butylamino group, N-ethyl, N-isobutyramino group, N-n-propyl, N-t-butylamino group, and the like.
  • the aryleno group include a phenyl group, a biphenyl group, and a naphthyl group.
  • Examples of the (C1-C4) alkoxy group include a methoxy group, an ethoxy group, an npropoxy group, an isopropoxy group, an nbutoxy group, an isobutoxy group, and a tbutoxy group.
  • Aryl groups include, for example, phenyl, methylphenyl, ethenylphenyl, n-propylphenyl, i-propylphenyl, dimethylphenyl Group, hydroxyphenyl group, methoxyphenyl group, ethoxyphenyl group, phenoxyphenyl group, aminophenyl group, N, N dimethylaminophenyl group, N, N jetylaminophenyl group, N, N diphenyl Examples thereof include an aminophenyl group, a cyanophyl group, a carboxyphenyl group, a biphenyl group, and a naphthyl group.
  • a phenyl group, a methylphenyl group, and a naphthyl group are particularly preferable, in which a phenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, and a naphthyl group are preferable.
  • the substitution position of the substituent in the aryl group is not particularly limited, and may be any position where substitution is possible.
  • the phosphorus compounds represented by the general formulas (1) to (4) may be commercially available compounds, or may be prepared by a usual production method.
  • the phosphoxide represented by the general formula (1) may be used.
  • the surfactant contained in the aqueous dispersion of the present invention includes a cationic type, a nonionic type and / or an anionic type surfactant, and includes a nonionic type, an anionic type or a nonionic type. It is preferable to use a mixture with an anionic surfactant.
  • the surfactant is used to disperse the aforementioned phosphorus compound.
  • anionic surfactant examples include alkyl sulfate salts such as higher alcohol sulfates, higher alkyl ether sulfates and sulfated fatty acid esters; alkylbenzene sulfonates and alkylnaphthalene sulfonates. Alkyl sulfonates; alkyl phosphate salts such as higher alcohol phosphate salts and higher alcohol alkylene oxide adduct phosphate salts.
  • Alkynoarylarylsulfonate salts polyoxyalkylene alkyl ether sulfate salts, ether ether carboxylate salts, polycarboxylate salts, funnel oil, petroleum sulfonates, and alkyl diphenyl ether sulfonate salts.
  • preferred anionic surfactants include the following general formula (107)
  • R represents a hydrogen atom, a (C6-C18) alkyl group, a styryl group or a benzyl group, n represents an integer of 1 to 15
  • n represents an integer of 1 to 15
  • R is an alkyl group or alkylaryl group
  • R is a hydrogen atom or R 0 (CH CH O) represents a group
  • R represents an alkyl group or an alkylaryl group
  • n represents a positive integer.
  • the surfactant represented by the general formula (107) is preferably a straight-chain alkyl group in which R is (C1 to C12), n force S4 to 12; R is a nonyl group, and n is 7 Is more preferred
  • Examples of the surfactant represented by the general formula (301) include Prisurf AL (trade name: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
  • Nonionic surfactants as surfactants contained in the aqueous dispersion of the present invention include polyoxyethylene styrenated phenyl ethers such as polyoxyethylene distyrenated phenyl ethers or polyoxyethylenes. And ethylene tristyrenated phenyl ether, and the following general formula (108)
  • the compound represented by (108) or a mixture thereof is preferred.
  • m ′ is !!-3 and n is 8-30.
  • Examples of the mixture of the compound represented by the general formula (108) include Neugen EA-87 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
  • the above surfactants may be used alone or in combination. Even if a plurality of types of anionic or nonionic surfactants are mixed, a plurality of types of anionic and nonionic types are used. Ion type surfactants can be mixed and used! /.
  • the above surfactant may be a commercially available compound or may be prepared by a usual production method.
  • the aqueous dispersion of the present invention may contain an ultraviolet absorber for the purpose of improving light fastness! /.
  • the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs ultraviolet rays, for example, salicylic acid type, benzophenone type, benzotriazole type, hindered amine type, triazine type, cinnamic acid type compound, stilbene type compound, or benzoxazo compound.
  • fluorescent brighteners which are compounds that emit ultraviolet light by absorbing ultraviolet rays, typified by the organic compounds.
  • R 1 represents (C1 to C 12) represents a linear or branched alkyl group or a Tamyl group, and a (C1 to C12) linear or branched alkyl group is preferred. More preferred are (C3 to C6) linear or branched alkyl groups, and still more preferred are (C3 to C5) branched alkyl groups such as isopropyl, isobutyl, sbutyl, t A butyl group, a 1 methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, and a 1 ethylpropyl group.
  • R is a hydroxy group, a linear or branched alkyl group of (C1-C12), (C1-C12)
  • a linear or branched alkyl group or a benzyloxy group of (C1 to C12), and a linear or branched alkyl group of (C1 to C6) is more preferred. And more preferably a (C1-C3) linear or branched alkyl group, and examples thereof include a methyl group, an ethyl group, an npropyl group, and an isopropyl group.
  • R is a hydrogen atom, a hydroxyl group, a linear or branched alkyl group of (C1 to C12) or (C1
  • To C12 represents a linear or branched alkoxy group, and a hydrogen atom or a linear or branched alkyl group of (C1 to C3) is preferred.
  • (C1 to C3) in R above represents a hydrogen atom or a linear or branched alkyl group of (C1 to C3).
  • R represents a hydrogen atom or a hydroxyl group, preferably a hydroxyl group.
  • X represents a hydrogen atom or a chlorine atom, and a chlorine atom is more preferred! /.
  • R to R and X are R force 3 ⁇ 4-butyl group, R force S methyl group, R
  • Examples of the ultraviolet absorber other than the benzotriazole compound represented by the general formula (106) include a benzophenone compound represented by the formula (101), the formula (102), or the formula (103), a general formula (104 ) (Wherein R and R are independently
  • R is hydroxyl, methoxy, ethoxy or benzyloxy
  • R is a hydrogen atom, hydroxyl group, methoxy group or ethoxy group, R is a hydrogen atom or hydroxyl group
  • X represents a hydrogen atom or a chlorine atom.
  • a benzotriazole-based one represented by the general formula (106) is particularly preferable.
  • the above ultraviolet absorber may be a commercially available compound or may be prepared by a usual production method.
  • the aqueous dispersion of the present invention is used as a flameproofing agent, and the composition containing the specific phosphorus compound and the surfactant is also included in the present invention.
  • the flameproofing agent is also included in the present invention.
  • the composition includes an aqueous dispersion, or a mixture of the specific phosphorus compound and the surfactant described above before preparation into an aqueous dispersion.
  • a preferred embodiment of the flameproof aqueous dispersion of the present invention is selected from the group consisting of compounds of the general formula (1), general formula (2), general formula (3) and general formula (4).
  • Phosphorus compounds are generally contained in the aqueous dispersion in a total amount of !! to 90% by weight, preferably 5 to 70% by weight, particularly preferably 10 to 50% by weight.
  • the aqueous dispersion of the present invention contains one phosphorus compound selected from the group consisting of the compounds represented by the general formula (1), the general formula (2), and the general formula (3). And one containing a phosphorus compound selected from the group consisting of compounds of general formula (1), general formula (2) and general formula (3) and a compound of general formula (4) I like it!
  • One type of phosphorus compound selected from the group consisting of compounds of general formula (1), general formula (2) and general formula (3) was contained in the aqueous dispersion in an amount of 0 .;! To 89.9% by weight. Those are preferred. Furthermore, it is preferable that the compound of the general formula (4) is contained in an aqueous dispersion in an amount of 0.;! To 89.9% by weight.
  • the phosphorus compounds represented by the general formula (1) may be selected from a plurality of compounds represented by the same general formula.
  • the aqueous dispersion of the present invention contains an ultraviolet absorber, its content is usually 0 .;
  • the content of the surfactant contained in the aqueous dispersion of the present invention is usually 5 to 200% by weight, preferably, based on the amount of the phosphorus compound and, if an ultraviolet absorber is contained, the total amount thereof. Is in the range of 10 to 100% by weight, particularly preferably 10 to 50% by weight.
  • the aqueous dispersion of the present invention includes polyvinylinorenoreconole, methinoresenorelose, canolepoxymethinoresenololose, starch paste for enhancing storage stability within the range not impairing the effect thereof.
  • Protective colloid agents such as: flameproofing aids for enhancing the flameproofing effect; antioxidants and the like may be included as necessary.
  • alkaline agents acids, fats and oils, higher alcohols, higher fatty acids, lower alcohols, organic solvents, penetration enhancers, polyhydric alcohols, preservatives, chelating agents, pH adjusters, wetting agents
  • an antifoaming agent, a fungicide, a pigment or a pigment may be added and used.
  • the aqueous dispersion of the present invention is prepared by adding a phosphorus compound and a surfactant, and further, if necessary, an ultraviolet absorber to water, and wet-pulverizing the resulting mixture using, for example, a sand grinder.
  • a sand grinder a sand grinder.
  • the particle size of the flameproofing agent used is a very important factor for the flameproofing performance, and the smaller the flameproofing agent particle size, the higher the flameproofing performance of the fiber. Can be granted. For example, it is known that if the dispersibility is poor, the flame retardant reaggregates and the particle size increases. In particular, when durability is required for the flameproofing performance of the flameproofing agent, the particle size of the flameproofing agent should be small so that the flameproofing agent can sufficiently diffuse inside the fiber. Fine particles having an average particle size of 2 m or less are preferred.
  • a surfactant as a dispersant, a phosphorus compound, and further an ultraviolet absorber are dispersed in water as fine particles having an average particle diameter of 2 ⁇ or less in a stable and high concentration state. That's the power S.
  • the aqueous dispersion of the present invention is preferably used as a flameproofing agent for fibers.
  • a fiber for flameproofing polyester fiber, particularly CDP fiber, or CDP fiber and other polyester fiber is used. Blended fiber is preferred.
  • CDP fibers and polyester fibers include polyethylene fibers such as polyethylene terephthalate, polybutylene terephthalate, polyoxyethoxybenzoate, polyethylene naphthalate, and cyclohexanedimethylene terephthalate;
  • Isophthalic acid, adipic acid, sulfoisophthalic acid and other dicarboxylic acid components propylene glycolanol, butylene glycolanol, cyclohexane dimethanolol, diethylene glycolol
  • fibers obtained by additionally copolymerizing diol components such as, but are not limited thereto.
  • these fibers may be any form such as yarn, woven fabric, knitted fabric, and non-woven fabric.
  • a method for flameproofing a fiber using the aqueous dispersion of the present invention as a flameproofing agent is also included in the present invention.
  • methods such as dip dyeing bathing and padding can be used.
  • a dispersion dye such as a fiber and a dispersion-type cationic dye and the aqueous dispersion of the present invention are used in combination at a temperature in the range of 110 to 150 ° C, preferably 120 to 140 ° C. Process for about 10 to 60 minutes. If necessary, dyes such as fluorescent dyes can be further removed.
  • the fiber structure is subjected to heat treatment such as dry heat treatment or steam heat treatment (using saturated atmospheric steam treatment, superheated steam treatment, high pressure steam treatment, etc.) after padding.
  • heat treatment such as dry heat treatment or steam heat treatment (using saturated atmospheric steam treatment, superheated steam treatment, high pressure steam treatment, etc.)
  • the heat treatment temperature is usually 110 to 210 ° C, preferably 170 to 210 ° C. If the heat treatment temperature exceeds 210 ° C, polyester synthetic fibers may be yellowed or embrittled.
  • the dip dyeing bath method and the padding method may be used in combination.
  • the fiber should be flameproofed by the dip dyeing bath method and then reprocessed by the padding method. Higher flameproofing performance can be imparted by using two kinds of methods together.
  • Me represents a methyl group
  • Ph represents a phenyl group
  • Et represents an ethyl group.
  • the compound of the above formula (201) is a compound of the above general formula (2) in which R 1, R 2 and R 3 are phenyl groups.
  • a compound which compound can be synthesized by the method described in JP-A-2004-43405. This compound is commercially available as TPP (trade name; manufactured by Hokuko Chemical Co., Ltd.).
  • the compound of the above formula (202) is a compound of the above general formula (1) in which R 1, R 2 and R 3 are phenyl groups.
  • a compound can be synthesized by the method described in JP-A-62-145095, for example.
  • This compound is commercially available as TPPO (trade name; manufactured by Hokuko Chemical Co., Ltd.).
  • the compound of the above formula (203) is R 1, R 2 and R 4, which is a methylphenyl group.
  • the compound of the above formula (205) is R 1, R 2 and R 6 which are methyl phenyl groups.
  • R is a naphthyl group, R and R force S phenyl group
  • the compound of the above formula (208) is R 1, R 2 and R 6 which are methyl phenyl groups.
  • This compound is a compound of general formula (4).
  • This compound can be synthesized by the method described in JP-A-2004-43405.
  • This compound is commercially available as TCP (trade name; manufactured by Daihachi Chemical Co., Ltd.).
  • R is a diphenyl group, R and R force S phenyl group
  • the compound of the above formula (211) is a compound of the above general formula (4) in which R 1, R 2 and R 3 are phenyl groups.
  • TPP (trade name; manufactured by Daihachi Chemical Co., Ltd.)
  • the compound of the above formula (220) is R and R force S phenyl group, R force S methyl group.
  • the compound of the above formula (222) is a compound of the above general formula (1) in which R and R force are S phenyl groups, and R is a cyclohexyl group.
  • a compound can be prepared, for example, by subjecting a compound marketed as DPCP (trade name: manufactured by Hokuko Chemical Co., Ltd.) to air oxidation or oxidation using hydrogen peroxide.
  • DPCP trade name: manufactured by Hokuko Chemical Co., Ltd.
  • the compound of the above formula (223) is R 1, R 2 and R 6 which are methyl phenyl groups
  • This compound is, for example, a compound commercially available as TPTP (trade name: manufactured by Hokuko Chemical Co., Ltd.), oxidized with air or hydrogen peroxide. It can be prepared by attaching to.
  • the compound of the above formula (224) is R 1, R 2, and R 4 power 3 -octyl group.
  • This compound is commercially available as TOPO (trade name: manufactured by Hokuko Chemical Co., Ltd.).
  • the compound of the above formula (210) is resorcinol bis (diphenyl phosphate) and is commercially available as RDP.
  • the compound of the above formula (213) has an R force 3 ⁇ 4 butyl group, an R force S methyl group, R is a hydrogen atom, R
  • the compound of the above formula (212) is an anionic surfactant represented by the above general formula (107), wherein R is an n nonyl group and n is 7.
  • a 30% aqueous solution containing the compound is commercially available as Hytenor Nore NE-05 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.). In this example, a commercially available 30% aqueous solution was used as it was.
  • Neugen EA-87 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was used as the nonionic surfactant. As described above, this nonionic surfactant is commercially available as a mixture of compounds represented by the general formula (108) wherein m ′ is !!-3 and n ′ is 8-30.
  • a mixture having the composition shown in Table 1 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.893 m.
  • a mixture having the composition shown in Table 2 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.899 m.
  • a mixture having the composition shown in Table 4 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.959 m.
  • a mixture having the composition shown in Table 5 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.883 m.
  • Formula (211) (—Compound of general formula (4)) 15. 0% Formula (213) (UV absorber) 1 ⁇ 0%
  • a mixture having the composition shown in Table 7 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.924 m.
  • a mixture having the composition shown in Table 10 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.901 m. ⁇
  • a mixture having the composition shown in Table 11 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.892 m.
  • Antifungal agent 0.l ° / c
  • a mixture having the composition shown in Table 12 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.894 m.
  • a mixture having the composition described in Table 14 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.963 11 m.
  • a mixture having the composition shown in Table 15 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.966 11 m.
  • a mixture having the composition described in Table 16 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.935 11 m.
  • a mixture having the composition described in Table 17 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.99811 m.
  • a mixture having the composition described in Table 18 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.94511 m. M18
  • the dyes used are disperse dyes: Power Yalon Microester Yellow AQ—LE 0 • 24%, Power Yalon Microester Red AQ—LE 0.24%, Power Yaron Microester Blue AQ—LE 0.24%; Cationic Dye As follows: Caklinole Yellow 3RL—ED 0.46%, Cakolinole Red GL—ED 0.24%, Cakolinole Blue GSL—ED 0.22%.
  • each fabric was subjected to reduction cleaning, followed by heat treatment at 180 ° C. for 30 seconds. Furthermore, in accordance with JIS K 3371, weak alkaline first-class detergent is used at a rate of lg / L. The bath ratio was 1:40, and each fabric was washed with water for 15 minutes at 60 ° C ⁇ 2 ° C, then rinsed 3 times for 5 minutes at 40 ° C ⁇ 2 ° C, and centrifuged for 2 minutes. Thereafter, hot air drying at 60 ° C ⁇ 5 ° C was taken as one cycle, and this was performed for 5 cycles.
  • the above reduction cleaning means preparing an aqueous solution of hydrosulfite 2g / L, caustic soda 2g / L, and surfactant lg / L, heating to 80 ° C, and then adding a flame-proofed fabric. For 20 minutes.
  • Tests were conducted using the JIS L 1091 A-1 method (45 degree microburner method) of the Fire Service Act, and the following evaluations were made.
  • the average afterflame time was calculated by dividing the total afterflame time measured in Test A by the number of measurements. The unit is seconds. The shorter the average afterflame time, the higher the flameproof performance.
  • the average burning area was calculated by measuring the burning area of the test piece and dividing the sum by the number of measurements. The unit is cm 2. The smaller the average combustion area, the higher the flameproof performance. [0058] (2) Test results
  • the pass rate of evaluation A is 75 to 100% for fabrics flameproofed with the aqueous dispersions prepared in Examples of the present invention;!
  • the fabric flameproofed with the aqueous dispersions prepared in Comparative Examples 1-5 was 0-69%, and the fabric flameproofed with the aqueous dispersion of the present invention had a pass rate. high.
  • the average afterflame time of evaluation B it was prepared in Comparative Examples 1 to 5 while the fabric flameproofed with the aqueous dispersion prepared in Examples 1 to 13 was 0.5 to 2.9. Fabrics that are flameproofed with an aqueous dispersion are 4.;!
  • the average burning area of evaluation C was prepared in Comparative Examples 1 to 5 while the fabric flameproofed with the aqueous dispersion prepared in Examples 1 to 13 was 3.6 to 4.7.
  • the flame-treated fabric with an aqueous dispersion is 7.;! ⁇ 33.6 and the average burning area Is also big.
  • a mixture having the composition shown in Table 20 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.899 m.
  • a mixture having the composition described in Table 21 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.912 11 m.
  • Antifungal agent 0. l ° / c
  • a mixture having the composition shown in Table 22 was wet-ground using a sand grinder 0 to prepare an aqueous dispersion of the present invention having an average particle size of 0.894 m.
  • a mixture having the composition described in Table 23 was wet-ground using a sand grinder.
  • An aqueous dispersion of the invention having an average particle size of m was prepared.
  • a mixture having the composition described in Table 24 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.898 m.
  • a mixture having the composition described in Table 25 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.957 11 m.
  • a mixture having the composition described in Table 26 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.954 11 m.
  • a mixture having the composition described in Table 27 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.9791 m.
  • a mixture having the composition described in Table 28 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.99811 m.
  • a mixture having the composition described in Table 29 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.94511 m.
  • Example 15 to 19 and Comparative Examples 7 to 11 were used in Example 20 or Comparative Example 12 for flameproofing polyester / CDP blended fiber fabrics. ! / In the same manner as in Test Example 1, a flame retardancy test was conducted. The results are shown in Table 30.
  • the pass rate of evaluation A was 100% for all the fabrics flameproofed with the aqueous dispersion prepared in Examples 15 to 19 of the present invention.
  • the fabrics flame-proofed with the aqueous dispersion prepared in Comparative Examples 7 to 11 containing a phosphate type compound such as the compound of the general formula (4) alone are 0 to 82%, and A fabric that has been flameproofed with an aqueous dispersion has a higher acceptance rate.
  • the average afterflame time of evaluation B was 0.5 to 0.9 for the fabric flame-proofed with the aqueous dispersion prepared in Examples 15 to 19, whereas the average afterflame time was prepared in Comparative Examples 7 to 11
  • the flame-proof fabric with the aqueous dispersion was 2.5 to 18.3, and the latter has an average after-flame time that is about 3 to 37 times longer.
  • Further evaluation The average combustion area of C
  • the fabric fire-treated with the aqueous dispersion prepared in 15 to 19 is 3.6 to 3.9, whereas the fabric fire-treated with the aqueous dispersion prepared in Comparative Examples 7 to 11 is 4. 7 to 33.6, the latter 1.2 to 9.3 times the average burning area.
  • a mixture having the composition described in Table 31 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.502 m.
  • a mixture having the composition described in Table 32 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.602 m.
  • a mixture having the composition described in Table 33 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.867 m.
  • a mixture having the composition described in Table 34 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.776 m.
  • a mixture having the composition described in Table 35 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.872, im.
  • a mixture having the composition described in Table 36 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.888 m.
  • a mixture having the composition described in Table 37 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.999 m.
  • Example 2 A blended fiber fabric containing 50% of CDP and other polyesters (CD P) in the same dyeing bath treatment method as in Example 14 using the aqueous dispersion prepared in! -27. / PET mixed fabric B) 40cm square was dyed and fireproofed at the same time.
  • Example 2 A flame retardant test was conducted in the same manner as in Test Example 1 on the polyester / CDP blended fiber fabric subjected to flameproofing in Example 28 using the aqueous dispersion prepared in! -27. The results are shown in Table 38.
  • a mixture having the composition shown in Table 39 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.688 m. 3 ⁇ 439
  • a mixture having the composition described in Table 40 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.622 m.
  • a blended fiber fabric (CD P / PET) containing 50% each of CDP and other polyesters by the same dyeing bath treatment method as in Example 14.
  • Mixed dough A 40cm squares were dyed and fireproofed at the same time.
  • a mixture having the composition described in Table 43 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.901 m.
  • a mixture having the composition described in Table 44 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.769 m.
  • a mixture having the composition described in Table 45 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.862 m.
  • a mixture having the composition shown in Table 48 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.988 m.
  • a blended fiber fabric (CD P / PET) containing 50% each of CDP and other polyesters by the same dyeing bath treatment method as in Example 14.
  • Mixed dough B 40cm square was dyed and fireproofed at the same time.
  • an aqueous dispersion of a non-halogen flameproofing agent capable of imparting durable and excellent flameproofing performance to fibers, in particular, blended fibers of CDP and other polyesters. S can.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fireproofing Substances (AREA)

Abstract

L'invention concerne une dispersion aqueuse contenant de un à trois composé(s) de phosphore choisi(s) parmi le groupe constitué d'oxydes de phosphine représenté par la formule générale (1) ci-dessous, de phosphines représentés par la formule générale (2) ci-dessous et de phosphites représentés par la formule générale (3) ci-dessous ou, en variante, de tels composés de phosphore et un ester d'acide phosphorique représenté par la formule générale (4) ci-dessous, et un agent tensioactif. Cette dispersion aqueuse est susceptible d'attribuer à des fibres, particulièrement à des fibres de CDP (polyester pouvant être teint à l'aide d'un colorant cationique) ou à des fibres mélangées contenant des fibres de CDP, d'excellentes propriétés antidéflagrantes durables. (Dans la formule (1), R11, R12 et R13 représentent indépendamment un groupe phényle ou similaire). (Dans la formule (2), R21, R22 et R23 représentent indépendamment un groupe phényle ou similaire). (Dans la formule (3), R31, R32 et R33 représentent indépendamment un groupe phényle ou similaire.) (Dans la formule (4), R41, R42 et R43 représentent indépendamment un groupe phényle ou similaire).
PCT/JP2007/070417 2006-10-20 2007-10-19 Agent ignifugeant ne contenant pas d'halogène et procédé destiné à ignifuger une fibre utilisant cet agent WO2008047897A1 (fr)

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WO2009122980A1 (fr) * 2008-03-31 2009-10-08 日華化学株式会社 Matériau ignifugeant pour fibre polyester, fibre polyester ignifugée à l’aide de ce matériau et procédé de production de ladite fibre polyester ignifugée
JP2012021247A (ja) * 2010-07-16 2012-02-02 Tb Kawashima Co Ltd 脱ハロゲン系難燃加工剤およびそれを使用したポリエステル系繊維製品の難燃加工法
CN102575169A (zh) * 2009-08-06 2012-07-11 阿灵索斯米乔斯莱肯公司 用于控火的水性组合物及方法
JP2012188776A (ja) * 2011-03-10 2012-10-04 Matsumoto Yushi Seiyaku Co Ltd 合成繊維の製造方法、繊維処理剤および合成繊維の融着防止方法
KR101350975B1 (ko) * 2011-08-31 2014-01-14 안현길 방염 조성물

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KR101442125B1 (ko) * 2013-06-17 2014-09-22 (주)건용 아미노알킬-비스-포스포닉산을 이용한 섬유용 방염제 조성물

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JP2012021247A (ja) * 2010-07-16 2012-02-02 Tb Kawashima Co Ltd 脱ハロゲン系難燃加工剤およびそれを使用したポリエステル系繊維製品の難燃加工法
JP2012188776A (ja) * 2011-03-10 2012-10-04 Matsumoto Yushi Seiyaku Co Ltd 合成繊維の製造方法、繊維処理剤および合成繊維の融着防止方法
KR101350975B1 (ko) * 2011-08-31 2014-01-14 안현길 방염 조성물

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