WO2011096391A1 - Aqueous dispersion for fireproofing, fireproofing method, and fireproofed fiber - Google Patents
Aqueous dispersion for fireproofing, fireproofing method, and fireproofed fiber Download PDFInfo
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- WO2011096391A1 WO2011096391A1 PCT/JP2011/052022 JP2011052022W WO2011096391A1 WO 2011096391 A1 WO2011096391 A1 WO 2011096391A1 JP 2011052022 W JP2011052022 W JP 2011052022W WO 2011096391 A1 WO2011096391 A1 WO 2011096391A1
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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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—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
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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
- D06M13/364—Cyanuric acid; Isocyanuric acid; Derivatives thereof
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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
- D06M13/395—Isocyanates
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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
- 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
- the present invention is an aqueous dispersion for flameproofing, which has excellent dispersion stability by using a combination of a specific halogen-based compound, a phosphate ester and a surfactant in a synthetic fiber structure, and is durable.
- TECHNICAL FIELD The present invention relates to an aqueous dispersion for flameproofing capable of imparting excellent flameproofing performance, a flameproofing method using the same, and fibers fireproofed thereby.
- brominated cycloalkane such as 1,2,5,6,9,10-hexabromocyclododecane is dispersed in water for flameproofing.
- a method for making a fiber into a flameproofing agent using an agent There is known a method for making a fiber into a flameproofing agent using an agent.
- the use of these brominated cycloalkane compounds is restricted due to problems such as the possibility of harmful effects on the natural environment. Therefore, in recent years, various phosphorus compounds have been investigated in place of this brominated cycloalkane compound, and flameproofing agents using phosphorus compounds such as organophosphates and methods for flameproofing fibers using the same have been proposed. (Patent Documents 1 to 4).
- fibers in particular, mixed fibers such as CDP (cation dyeable polyester) fibers and polyester fibers, or acrylic fibers and polyester fibers
- CDP chlorogenated cycloalkane compounds
- these are also fibers, in particular CDP (cation dyeable polyester) fibers and polyester fibers, or acrylic fibers. It was not possible to impart sufficient flameproofing performance to blended fibers such as polyester fibers and fibers provided with various functions such as antibacterial processing, deodorization processing, and surface processing.
- An object of the present invention is an aqueous dispersion for flameproofing which is excellent in dispersion stability. It is a fiber, in particular, mixed fibers such as CDP fiber, CDP fiber and polyester fiber, acrylic fiber and polyester fiber, and functionality. An object is to provide an aqueous dispersion for flameproofing capable of imparting excellent durable and flameproofing performance to the imparted fiber, a flameproofing method using the same, and a flameproofed fiber thereby. .
- the present inventors firstly impart a flameproof performance excellent in durability to a fiber by using a specific halogen compound and a specific phosphoric acid triaryl ester compound. I found that I can do it. However, when the obtained dispersion is dispersed using the ethylene oxide adduct sulfate ester of styrenated phenol that has been generally used so far, the dispersion stability is poor and separation, solid analysis, etc. occur and flameproofing It could not be used as a processing agent.
- An aqueous dispersion for flameproofing processing comprising a halogen compound (A) represented by the following formula (1), a phosphoric acid naphthyl diphenyl ester compound (B) represented by the following formula (2) and a surfactant (C).
- A halogen compound represented by the following formula (1)
- B phosphoric acid naphthyl diphenyl ester compound
- C surfactant
- the surfactant (C) is a compound represented by the following formula (3) or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or a compound represented by the following formula (4) or a salt thereof:
- An aqueous dispersion for flameproofing [Wherein R represents a phenyl group, a cresyl group, a naphthyl group or a biphenyl group, and n represents an integer of 1 to 40]
- R represents a (C8-C30) alkyl group or an aryl group which may have a substituent
- R ′ represents a hydrogen atom or a RO (CH 2 CH 2 O) n group, and n represents 1 to 30 Indicates an integer.
- An aqueous dispersion for flameproofing processing comprising a halogen compound (A) represented by the following formula (1), a phosphoric acid triphenyl ester compound (B ′) represented by the following formula (303), and a surfactant (C)
- the weight ratio of the halogen compound (A) to the phosphoric acid triphenyl ester compound (B ′) is in the range of 1.5: 1 to 20: 1
- the surfactant (C) is represented by the following formula (3 ) Or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or an aqueous dispersion for flameproofing which is a compound represented by the following formula (4) or a salt thereof;
- R represents a phenyl group, a cresyl group, a naphthyl group or a biphenyl group, and n represents an integer of 1 to 40]
- R represents a (C8-C30) alkyl group or an an
- aqueous dispersion for flameproofing according to any one of the above [1] to [3], which is contained in a total amount of 1 to 90% by weight in the aqueous dispersion for flame processing; [5]. Furthermore, the aqueous dispersion for flameproofing according to any one of the above [1] to [4], further comprising an ultraviolet absorber; [6].
- a method for flameproofing a fiber comprising using the aqueous dispersion for flameproofing according to any one of the above [1] to [8]; and [10].
- the aqueous dispersion for flameproofing of the present invention is a combination of the halogen compound (A) represented by the formula (1) and the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2), or
- the halogen compound (A) represented by the formula (1) and the phosphoric acid triphenyl ester compound (B ′) represented by the formula (303) are combined at a specific ratio, and the surfactant (C) Is an aqueous dispersion for flameproofing processing, and has excellent dispersion stability.
- fibers especially blended fibers such as CDP fibers, CDP fibers and polyester fibers, acrylic fibers and polyester fibers, and functions.
- the halogen compound (A) does not have a harmful effect on the natural environment, and gives an excellent aqueous dispersion for flameproofing with little harm to the environment.
- the aqueous dispersion for flameproofing of the present invention comprises the halogen compound (A) represented by the formula (1), the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2), and the surface activity. It contains a compound represented by the formula (3) or a salt thereof and a cresol sulfonic acid formalin condensate or a salt thereof, or a compound represented by the formula (4) or a salt thereof, which is an agent (C).
- the aqueous dispersion for flameproofing of the present invention comprises a halogen compound (A) represented by the formula (1) and a phosphoric acid triphenyl ester compound (B ′) represented by the formula (303),
- the surfactant (C) is a compound represented by the formula (3) or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or a compound represented by the formula (4) or a salt thereof.
- the weight ratio of the halogen compound (A) to the phosphoric acid triphenyl ester compound (B ′) is in the range of 1.5: 1 to 20: 1.
- the aqueous dispersion for flameproofing of the present invention may contain an ultraviolet absorber for the purpose of further improving the light fastness.
- the halogen compound (A) represented by the formula (1), the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2) and the phosphoric acid triphenyl ester compound represented by the formula (303) ( B ′) can be prepared by known methods described in the literature, and is also commercially available.
- the halogen compound (A) is available from Aldrich
- the phosphate naphthyl diphenyl ester compound (B) is commercially available from Daihachi Chemical Co., Ltd. under the trade name NDPP
- the phosphate triphenyl ester compound (B ') Is commercially available from Daihachi Chemical Co., Ltd. under the trade name TPP.
- R represents a phenyl group, a cresyl group, a naphthyl group or a biphenyl group
- the compound represented by the formula (3) is preferably a compound in which R is a naphthyl group or biphenyl group and n is 3 to 20, and a compound in which R is a naphthyl group and n is 4 to 13 is particularly preferable.
- the compound represented by the formula (3) may be a single product or a mixture. Examples of the compound represented by the formula (3) include Newcol B4-SN (manufactured by Nippon Emulsifier Co., Ltd.).
- Examples of the salt of the compound represented by the formula (3) include salts that are alkali metals, ammonium, and the like as counter cations.
- Examples of the counter cation include lithium, sodium, potassium, ammonium, and the like. Or ammonium is preferable.
- R has a (C8-C30) alkyl group or a substituent.
- R ′ is a hydrogen atom or RO (CH 2 CH 2 O) n group, and n is an integer of 1 to 30.
- R ′ is a RO (CH 2 CH 2 O) n group
- R and R ′ are preferably the same.
- R in the compound represented by the formula (4) is a (C8-C12) alkyl group, naphthyl group, biphenyl group, benzylphenyl group or styrylphenyl group, and a compound in which n is 3 to 20, Of these, compounds in which R is a naphthyl group, benzylphenyl group or styrylphenyl group and n is 4 to 13 are particularly preferred.
- the substitution position is not particularly limited as long as substitution is possible.
- substituents include halogen atoms such as fluorine atom, bromine atom and chlorine atom; (C1-C6) alkyl group optionally substituted with halogen atom such as methyl group, trifluoromethyl group, ethyl group and propyl group; And (C1-C6) alkoxy groups such as methoxy group and ethoxy group.
- the compound represented by the formula (4) may be a single product or a mixture. Examples of the compound represented by the formula (4) include Prisurf AL (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
- Examples of the salt of the compound represented by the formula (4) include salts that are alkali metals, ammonium, and the like as counter cations.
- Examples of the counter cation include lithium, sodium, potassium, ammonium, and the like. Ammonium is preferred.
- the cresolsulfonic acid formalin condensate in the surfactant (C) contained in the aqueous dispersion for flameproofing of the present invention is metacresolsulfonic acid, paracresolsulfonic acid, orthocresolsulfonic acid or a mixture thereof and formalin.
- a salt thereof a salt that is an alkali metal, ammonium, or the like is included as a counter cation. Examples of the counter cation include lithium, sodium, potassium, ammonium, and the like. Sodium or ammonium is preferred.
- the cresol sulfonic acid formalin condensate may be a single product or a mixture. Examples of the cresol sulfonic acid formalin condensate include Demol SC-30 (manufactured by Kao Corporation).
- any compound that absorbs ultraviolet rays can be used without particular limitation.
- UV absorber examples include salicylic acid compounds, benzophenone compounds, benzotriazole compounds, hindered amine compounds, triazine compounds, cinnamic acid compounds, stilbene compounds; or ultraviolet rays represented by benzoxazole compounds. It is also possible to use a compound (so-called fluorescent whitening agent) that absorbs and emits fluorescence.
- a structural formula of a preferable ultraviolet absorber is shown below.
- R 5 includes (C1-C12) linear or branched alkyl group or cumyl group, more preferably (C3-C6) linear or A branched chain alkyl group, and more preferably a (C3-C5) branched chain alkyl group, such as isopropyl group, isobutyl group, s-butyl group, t-butyl group, 1-methylbutyl group, 2-methylbutyl group. Group, 3-methylbutyl group, 1-ethylpropyl group and the like.
- examples of R 6 include a hydroxyl group, a (C1-C12) linear or branched alkyl group, a (C1-C12) linear or branched alkoxy group, or a benzyloxy group.
- a linear or branched alkyl group is preferred. More preferred is a (C1-C6) linear or branched alkyl group, and further preferred is a (C1-C3) linear or branched alkyl group, such as a methyl group, an ethyl group, or an n-propyl group. And isopropyl group.
- R 7 includes a hydrogen atom, a hydroxyl group, a (C1-C12) linear or branched alkyl group, or a (C1-C12) linear or branched alkoxy group, and includes a hydrogen atom, a methyl group , An ethyl group, an n-propyl group or an isopropyl group is preferable, and a hydrogen atom is more preferable.
- R 8 includes a hydrogen atom or a hydroxyl group, preferably a hydroxyl group, and X includes a hydrogen atom or a chlorine atom, and a chlorine atom is preferable.
- R 5 is a t-butyl group
- R 6 is a methyl group
- R 7 is a hydrogen atom
- R 8 is a hydroxyl group
- X is a chlorine atom
- Benzotriazole-based and benzophenone-based compound represented by the formula (105) [wherein R 1 is a (C1-C2) alkyl group or cumyl group, R 2 is a hydroxyl group, (C1-C2) alkoxy A group or a benzyloxy group, R 3 represents a hydrogen atom, a hydroxyl group or a (C1-C2) alkoxy group, R 4 represents a hydrogen atom or a hydroxyl group, and X represents a hydrogen atom or a chlorine atom. ].
- a particularly preferred compound is a benzotriazole compound represented by the formula (106).
- the content ratio of each component in the aqueous dispersion for flameproofing of the present invention is as follows. That is, the halogen compound (A) and the phosphoric acid naphthyl diphenyl ester compound (B) are usually 1 to 70% by weight, preferably 5 to 50% by weight, particularly preferably 5 to 30% by weight in the aqueous dispersion for flameproofing. It is contained in the range. In the aqueous dispersion for flameproofing, the weight ratio of the halogen compound (A) and the naphthyl diphenyl ester compound (B) is preferably 1:20 to 20: 1.
- the weight ratio of the halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) in the aqueous dispersion for flameproofing is in the range of 1.5: 1 to 20: 1.
- the halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) are usually 1 to 70% by weight, preferably 5 to 50% by weight, particularly preferably 5 to 30% by weight in the aqueous dispersion for flameproofing. Contained in a range.
- the total amount of (B ′) and the surfactant (C) is preferably 1 to 90% by weight in the aqueous dispersion for flameproofing.
- the content thereof is usually in the range of 0.1 to 10% by weight, preferably 0.5 to 10% by weight, particularly preferably 1 to 5% by weight in the aqueous dispersion for flameproofing. Contained.
- the amount of the surfactant (C) used is usually 5 to 80% by weight, preferably 10%, based on the total amount of the halogen compound (A), the phosphoric acid naphthyl diphenyl ester compound (B) and the optional ultraviolet absorber. It is in the range of ⁇ 50% by weight, particularly preferably 15 to 35% by weight.
- the compound represented by the above formula (3) or a salt thereof and the cresolsulfonic acid formalin condensate or the salt thereof are used as the surfactant (C)
- the compound represented by the above formula (3) or The weight ratio of the salt to the cresolsulfonic acid formalin condensate or the salt thereof is preferably in the range of 10: 1 to 1:10.
- the amount of water in the aqueous dispersion for flameproofing of the present invention is not particularly limited, but is preferably in the range of 20 to 80% by weight.
- the aqueous dispersion for flameproofing of the present invention may contain other additives such as surfactants and dispersants as necessary.
- protective colloid agents such as polyvinyl alcohol, methylcellulose, carboxymethylcellulose, starch paste, naphthyl diphenyl ester compound (B) and triphenyl ester compound (B ′) phosphate Flameproofing aids, antioxidants and the like for enhancing the flameproofing effect such as phosphoric acid esters and phosphoric acid amides may be included.
- alkali agents acids, fats and oils, higher alcohols, higher fatty acids, lower alcohols, organic solvents, penetration enhancers, polyhydric alcohols, preservatives, chelating agents, pH adjusters, dyes and pigments, etc. May be added.
- the aqueous dispersion for flameproofing of the present invention is prepared by pulverizing each of the above components with a sand grinder, if necessary, and adding them to water.
- the fiber that can be flameproofed by the aqueous dispersion for flameproofing of the present invention is not particularly limited, and examples thereof include polyester fibers, particularly CDP fibers, CDP fibers and polyester fibers, or acrylic fiber and polyester blended fibers.
- CDP fibers and polyester fibers include polyethylene terephthalate, polybutylene terephthalate, polyoxyethoxybenzoate, polyethylene naphthalate, cyclohexanedimethylene terephthalate, and other polyester fibers.
- polyester fibers examples include, but are not limited to, fibers of materials obtained by copolymerization of dicarboxylic acid components such as adipic acid and sulfoisophthalic acid, and diol components such as propylene glycol, butylene glycol, cyclohexane dimethanol, and diethylene glycol. It is not something.
- the aqueous dispersion for flameproofing of the present invention can also be used for fibers having various functionalities such as antibacterial processing, deodorizing processing, surface processing, and the like, thereby imparting the functionality.
- the fiber can also be flameproofed.
- the fiber structure may be in any form such as yarn, woven fabric, knitted fabric, and non-woven fabric.
- a known method such as a dip dyeing bath method or a padding method can be used.
- a disperse dye for fibers, a dispersive cationic dye or the like and the aqueous dispersion for flameproofing of the present invention are used in combination at 110 to 150 ° C., preferably 120 to 140 ° C. Processing is performed for about 10 to 60 minutes at a temperature in the range. If necessary, a dye such as a fluorescent dye can be further added.
- the fiber structure is padded and then heat-treated by dry heat treatment or steam heat treatment such as saturated atmospheric steam treatment, superheated steam treatment or high-pressure steam treatment.
- dry heat treatment or steam heat treatment such as saturated atmospheric steam treatment, superheated steam treatment or high-pressure steam treatment.
- the heat treatment temperature is usually in the range of 110 to 210 ° C., preferably in the range of 170 to 210 ° C. If the heat treatment temperature exceeds 210 ° C, the polyester synthetic fibers may be yellowed or embrittled.
- the dip dyeing bath method and the padding method may be used in combination.
- the fiber is subjected to flameproofing by the dip dyeing bath method and then reprocessed by the padding method. By this method, higher flameproof performance can be imparted.
- the compound of the formula (301) is commercially available from Yamamitsu Co., Ltd. under the trade name SANKO-BCA.
- the compound of formula (302) is commercially available from Hokuko Chemical Co., Ltd. under the trade name TPPO.
- Each component shown in the following Examples and Comparative Examples was pulverized with a sand grinder as necessary, and added to water together with other components to obtain an aqueous dispersion for flameproofing.
- Example 1 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 25.0% Phosphate naphthyl diphenyl ester compound (B) 5.0% New Coal B4-SN (compound of formula (3)) 3.3% Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Example 2 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 15.0% Phosphate naphthyl diphenyl ester compound (B) 15.0% New Coal B4-SN (compound of formula (3)) 3.3% Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Example 3 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- Example 4 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 15.0% Phosphate naphthyl diphenyl ester compound (B) 15.0% Prisurf ALNa salt (compound of formula (4)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Example 5 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 25.0% Phosphoric acid triphenyl ester (303) 5.0% New Coal B4-SN (compound of formula (3)) 3.3% Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Example 6 An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 20.0% Phosphoric acid triphenyl ester (303) 10.0% New Coal B4-SN (compound of formula (3)) 3.3% Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- composition Water 63.0% Halogen compound (A) 15.0% Compound of formula (301) 15.0% Prisurf ALNa salt (compound of formula (4)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- composition Water 63.0% Halogen compound (A) 15.0% Compound of formula (302) 15.0% Prisurf ALNa salt (compound of formula (4)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- composition Water 63.0% Halogen compound (A) 15.0% Phosphoric acid triphenyl ester (303) 15.0% Prisurf ALNa salt (compound of formula (4)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- composition Water 63.0% Halogen compound (A) 15.0% Phosphoric acid triphenyl ester (303) 15.0% New Coal B4-SN (compound of formula (3)) 3.3% Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Comparative Example 5 An aqueous dispersion for flameproofing was obtained using the composition shown below.
- composition Water 63.0% Halogen compound (A) 15.0% Phosphate naphthyl diphenyl ester compound (B) 15.0% New Coal B4-SN (compound of formula (3)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Comparative Example 7 An aqueous dispersion for flameproofing was obtained using the composition shown below.
- Comparative Example 8 An aqueous dispersion for flameproofing was obtained using the composition shown below.
- Comparative Example 9 An aqueous dispersion for flameproofing was obtained using the composition shown below.
- Comparative Example 10 An aqueous dispersion for flameproofing was obtained using the composition shown below.
- composition Water 63.0% Phosphate naphthyl diphenyl ester compound (B) 30.0% Prisurf ALNa salt (compound of formula (4)) 6.3% Thickener 0.5% Antifoam 0.1% Antifungal agent 0.1% Total amount: 100.0%
- Example 7 The fibers were flameproofed using each of the flameproofing aqueous dispersions prepared in Examples 1-6. At the same time, the fibers were similarly flameproofed using the aqueous dispersions for flameproofing prepared in Comparative Examples 1 to 10. That is, using each flameproofing aqueous dispersion prepared in Examples 1 to 6 or Comparative Examples 1 to 10 described above, 40 cm of a blended fiber of 70% polyester and 30% CDP by the same dye bath treatment method. Each side was dyed and fireproofed at the same time.
- the dyes used were disperse dyes: Kayalon Microester Yellow AQ-LE 0.24%, Kayalon Microester Red AQ-LE 0.24%, Kayaron Microester Blue AQ-LE 0.24% (all Nippon Kayaku ( Co., Ltd.), Kayacrill Yellow 3RL-ED 0.46%, Kayacrill Red GL-ED 0.24%, Kayacriru Blue GSL-ED 0.22% (all manufactured by Nippon Kayaku Co., Ltd.) .
- each fabric was subjected to reduction cleaning, and then heat-treated at 170 ° C. for 60 seconds. Further, according to JIS K3371, a weak alkaline first-class detergent was used at a rate of 1 g / L, a bath ratio of 1:40, and each fabric was washed with water at 60 ° C. ⁇ 2 ° C. for 15 minutes, and then 40 ° C. ⁇ 2 ° C. And 5 minutes of rinsing for 5 minutes, centrifugal dehydration for 2 minutes, and then water washing with hot air drying at 60 ° C. ⁇ 5 ° C. as one cycle for 5 cycles to obtain a flameproofed fiber.
- the above-described reduction cleaning refers to the following operation.
- an aqueous solution of hydrosulfite 2 g / L, caustic soda 2 g / L, and nonionic surfactant 1 g / L was prepared, heated to 80 ° C., and then added with the above flameproofed fabric for 10 minutes. The operation to process.
- Test example 1 Flame Retardancy and Dispersion Stability Test 16 kinds of blended fiber fabric and untreated fabric obtained by the operation of Example 7 were used as test pieces, and a flammability test was conducted on these. Further, a dispersion stability test of each aqueous dispersion for flameproofing prepared in Examples 1 to 6 or Comparative Examples 1 to 10 was performed.
- Test method Test method for flammability test Tests were conducted according to the Fire Service Act JIS L1091A-1 method (45 degree micro burner method), and the following evaluations were made. The results are shown in the table below.
- Pass rate A case where the after flame time was 3 seconds or less was regarded as acceptable, and a numerical value obtained by dividing the number of times of acceptance during the measurement by the number of times of measurement was described as the acceptance rate. The fractional part is rounded off and the unit is%. The higher the acceptance rate, the higher the flameproof performance.
- the parentheses after the pass rate are the number of passes and the number of measurements used to calculate the pass rate, and are indicated by “(pass times / measurement times)”.
- Evaluation B Average after flame time : The average afterflame time was calculated by dividing the total afterflame time measured in Evaluation A by the number of measurements. The unit is seconds. The shorter the average afterflame time, the higher the flameproof performance.
- the pass rate of evaluation A is 96 to 100% of the aqueous dispersion for flameproofing of Examples 1 to 6 of the present invention, whereas the aqueous dispersion for flameproofing of each comparative example is In the case of an aqueous dispersion for flameproofing that does not use a mixture of both the halogen compound (A) and the phosphoric acid naphthyl diphenyl ester compound (B) (comparative examples 1 to 3, 9, 10) is 64 to 66%, and the aqueous dispersion for flameproofing of Examples of the present invention has a higher pass rate.
- the pass rate of evaluation A of the aqueous dispersion for flameproofing of Examples 5 and 6 containing the halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) in the composition ratio of the present invention is 96%. 100%, but 64 to 80% of the aqueous dispersion for flameproofing of Comparative Examples 3 to 5 containing both of them at 1: 1 or 1: 2 and pass the aqueous dispersion for flameproofing of the present invention. The rate is high.
- the aqueous dispersions for flameproofing of Examples 1 to 6 were 0.7 to 1.8, whereas the aqueous dispersions for flameproofing of each comparative example were 2
- the average afterflame time of the aqueous dispersion for flameproofing of Comparative Example is long. Further, the dispersion stability is stable in the case of an aqueous dispersion for flameproofing using only the halogen compound (A) or the naphthyl diphenyl ester compound (B) (Comparative Examples 9 and 10), but mixed.
- aqueous dispersion for flameproofing In the case of an aqueous dispersion for flameproofing (Comparative Examples 6 to 8), the stability is deteriorated unless the surfactant (C) used in the present invention is used.
- the superiority of the aqueous dispersion for flameproofing of the present invention is clear from the overall pass results of evaluation A, average after-flame time of evaluation B, and dispersion stability test results.
- the test piece using the aqueous dispersion for flameproofing of the present invention exhibits excellent flameproofing performance, and the dispersion stability of the aqueous dispersion for flameproofing of the present invention is also excellent. found.
- the test piece using the flameproofing aqueous dispersion of the present invention retains the above performance despite repeated washing with water for 5 cycles. It is clear that it is excellent.
- the aqueous dispersion for flameproofing of the present invention is a combination of the halogen compound (A) represented by the formula (1) and the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2), or A specific proportion of the halogen compound (A) represented by the formula (1) and the phosphoric acid triphenyl ester compound (B ′) represented by the formula (303) are combined, and the surfactant (C)
- the dispersion is excellent in dispersion stability, and can impart durable and excellent flameproofing performance to fibers, particularly CDP and polyester, or acrylic fiber and polyester blended fibers.
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Abstract
Description
一方、臭素化シクロアルカン化合物に代わるハロゲン化合物としてもいくつか提案がされているが(特許文献5~7)、これらも繊維、特にCDP(カチオン可染型ポリエステル)繊維とポリエステル繊維、又はアクリル繊維とポリエステル繊維のような混紡繊維や、抗菌加工、消臭加工、表面加工等の種々の機能性を付与された繊維には十分な防炎性能を付与することができなかった。 However, when these phosphorus compounds are used, fibers, in particular, mixed fibers such as CDP (cation dyeable polyester) fibers and polyester fibers, or acrylic fibers and polyester fibers, antibacterial processing, deodorizing processing, Sufficient flameproofing performance could not be imparted to fibers provided with various functionalities such as surface processing.
On the other hand, although some proposals have been made as halogen compounds in place of brominated cycloalkane compounds (Patent Documents 5 to 7), these are also fibers, in particular CDP (cation dyeable polyester) fibers and polyester fibers, or acrylic fibers. It was not possible to impart sufficient flameproofing performance to blended fibers such as polyester fibers and fibers provided with various functions such as antibacterial processing, deodorization processing, and surface processing.
[1].下記式(1)で表されるハロゲン化合物(A)、下記式(2)で表されるリン酸ナフチルジフェニルエステル化合物(B)及び界面活性剤(C)を含む防炎加工用水性分散液であって、該界面活性剤(C)が下記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は下記式(4)で表される化合物若しくはその塩である、防炎加工用水性分散液;
[2].ハロゲン化合物(A)とリン酸ナフチルジフェニルエステル化合物(B)の重量比が1:20~20:1の範囲である上記[1]に記載の防炎加工用水性分散液;
[3].下記式(1)で表されるハロゲン化合物(A)、下記式(303)で表されるリン酸トリフェニルエステル化合物(B’)及び界面活性剤(C)を含む防炎加工用水性分散液であって、ハロゲン化合物(A)とリン酸トリフェニルエステル化合物(B’)の重量比が1.5:1~20:1の範囲であり、該界面活性剤(C)が下記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は下記式(4)で表される化合物若しくはその塩である防炎加工用水性分散液;
[4].ハロゲン化合物(A)、リン酸ナフチルジフェニルエステル化合物(B)及び界面活性剤(C)、又は、ハロゲン化合物(A)、リン酸トリフェニルエステル化合物(B’)及び界面活性剤(C)を防炎加工用水性分散液中に総量で1~90重量%含有する上記[1]~[3]のいずれかに記載の防炎加工用水性分散液;
[5].更に、紫外線吸収剤を含有する上記[1]~[4]のいずれかに記載の防炎加工用水性分散液;
[6].繊維の防炎加工に使用する上記[1]~[5]のいずれかに記載の防炎加工用水性分散液;
[7].繊維がポリエステル繊維である上記[6]に記載の防炎加工用水性分散液;
[8].ポリエステル繊維がカチオン可染型ポリエステル繊維又はカチオン可染型ポリエステル繊維を含有する混紡繊維である上記[7]に記載の防炎加工用水性分散液;
[9].上記[1]~[8]のいずれかに記載の防炎加工用水性分散液を用いることを含む繊維の防炎加工方法;及び
[10].上記[9]に記載の方法により防炎加工された繊維。 That is, the present invention relates to the following 1) to 10).
[1]. An aqueous dispersion for flameproofing processing comprising a halogen compound (A) represented by the following formula (1), a phosphoric acid naphthyl diphenyl ester compound (B) represented by the following formula (2) and a surfactant (C). The surfactant (C) is a compound represented by the following formula (3) or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or a compound represented by the following formula (4) or a salt thereof: An aqueous dispersion for flameproofing;
[2]. The aqueous dispersion for flameproofing according to the above [1], wherein the weight ratio of the halogen compound (A) and the naphthyl diphenyl ester compound (B) is in the range of 1:20 to 20: 1;
[3]. An aqueous dispersion for flameproofing processing, comprising a halogen compound (A) represented by the following formula (1), a phosphoric acid triphenyl ester compound (B ′) represented by the following formula (303), and a surfactant (C) The weight ratio of the halogen compound (A) to the phosphoric acid triphenyl ester compound (B ′) is in the range of 1.5: 1 to 20: 1, and the surfactant (C) is represented by the following formula (3 ) Or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or an aqueous dispersion for flameproofing which is a compound represented by the following formula (4) or a salt thereof;
[4]. Halogen compound (A), phosphate naphthyl diphenyl ester compound (B) and surfactant (C), or halogen compound (A), phosphate triphenyl ester compound (B ′) and surfactant (C) are prevented. The aqueous dispersion for flameproofing according to any one of the above [1] to [3], which is contained in a total amount of 1 to 90% by weight in the aqueous dispersion for flame processing;
[5]. Furthermore, the aqueous dispersion for flameproofing according to any one of the above [1] to [4], further comprising an ultraviolet absorber;
[6]. The aqueous dispersion for flameproofing according to any one of the above [1] to [5] used for flameproofing of fibers;
[7]. The aqueous dispersion for flameproofing according to the above [6], wherein the fiber is a polyester fiber;
[8]. The aqueous dispersion for flameproofing according to the above [7], wherein the polyester fiber is a cationic dyeable polyester fiber or a blended fiber containing a cationic dyeable polyester fiber;
[9]. A method for flameproofing a fiber, comprising using the aqueous dispersion for flameproofing according to any one of the above [1] to [8]; and [10]. A fiber that has been flameproofed by the method described in [9] above.
本発明の防炎加工用水性分散液は、前記式(1)で表されるハロゲン化合物(A)と前記式(2)で表されるリン酸ナフチルジフェニルエステル化合物(B)と、前記界面活性剤(C)である前記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は前記式(4)で表される化合物若しくはその塩を含有することを特徴とする。
又、本発明の防炎加工用水性分散液は、前記式(1)で表されるハロゲン化合物(A)と前記式(303)で表されるリン酸トリフェニルエステル化合物(B’)と、前記界面活性剤(C)である前記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は前記式(4)で表される化合物若しくはその塩を含有し、ハロゲン化合物(A)とリン酸トリフェニルエステル化合物(B’)の重量比が1.5:1~20:1の範囲であることを特徴とする。
更に、本発明の防炎加工用水性分散液は、より耐光堅牢度を向上させる目的で紫外線吸収剤を含有してもよい。
前記式(1)で表されるハロゲン化合物(A)、前記式(2)で表されるリン酸ナフチルジフェニルエステル化合物(B)及び前記式(303)で表されるリン酸トリフェニルエステル化合物(B’)は文献記載の公知方法により調製することができ、市販もされている。例えば、ハロゲン化合物(A)はアルドリッチ社から入手可能であり、リン酸ナフチルジフェニルエステル化合物(B)は大八化学(株)から商品名NDPPとして市販されており、リン酸トリフェニルエステル化合物(B’)は大八化学(株)から商品名TPPとして市販されている。 Hereinafter, the present invention will be described in detail.
The aqueous dispersion for flameproofing of the present invention comprises the halogen compound (A) represented by the formula (1), the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2), and the surface activity. It contains a compound represented by the formula (3) or a salt thereof and a cresol sulfonic acid formalin condensate or a salt thereof, or a compound represented by the formula (4) or a salt thereof, which is an agent (C). And
The aqueous dispersion for flameproofing of the present invention comprises a halogen compound (A) represented by the formula (1) and a phosphoric acid triphenyl ester compound (B ′) represented by the formula (303), The surfactant (C) is a compound represented by the formula (3) or a salt thereof and a cresolsulfonic acid formalin condensate or a salt thereof, or a compound represented by the formula (4) or a salt thereof. The weight ratio of the halogen compound (A) to the phosphoric acid triphenyl ester compound (B ′) is in the range of 1.5: 1 to 20: 1.
Furthermore, the aqueous dispersion for flameproofing of the present invention may contain an ultraviolet absorber for the purpose of further improving the light fastness.
The halogen compound (A) represented by the formula (1), the phosphoric acid naphthyl diphenyl ester compound (B) represented by the formula (2) and the phosphoric acid triphenyl ester compound represented by the formula (303) ( B ′) can be prepared by known methods described in the literature, and is also commercially available. For example, the halogen compound (A) is available from Aldrich, and the phosphate naphthyl diphenyl ester compound (B) is commercially available from Daihachi Chemical Co., Ltd. under the trade name NDPP, and the phosphate triphenyl ester compound (B ') Is commercially available from Daihachi Chemical Co., Ltd. under the trade name TPP.
前記式(3)で表される化合物としては、例えば、ニューコールB4-SN(日本乳化剤(株)製)等が挙げられる。 In the compound represented by the formula (3) in the surfactant (C) contained in the aqueous dispersion for flameproofing of the present invention, R represents a phenyl group, a cresyl group, a naphthyl group or a biphenyl group, and n Represents 1 to 40. The compound represented by the formula (3) is preferably a compound in which R is a naphthyl group or biphenyl group and n is 3 to 20, and a compound in which R is a naphthyl group and n is 4 to 13 is particularly preferable. . The compound represented by the formula (3) may be a single product or a mixture.
Examples of the compound represented by the formula (3) include Newcol B4-SN (manufactured by Nippon Emulsifier Co., Ltd.).
前記式(4)で表される化合物としては、例えば、プライサーフAL(第一工業製薬(株)製)等が挙げられる。 In the compound represented by the formula (4) in the surfactant (C) contained in the aqueous dispersion for flameproofing of the present invention, R has a (C8-C30) alkyl group or a substituent. R ′ is a hydrogen atom or RO (CH 2 CH 2 O) n group, and n is an integer of 1 to 30. When R ′ is a RO (CH 2 CH 2 O) n group, R and R ′ are preferably the same. R in the compound represented by the formula (4) is a (C8-C12) alkyl group, naphthyl group, biphenyl group, benzylphenyl group or styrylphenyl group, and a compound in which n is 3 to 20, Of these, compounds in which R is a naphthyl group, benzylphenyl group or styrylphenyl group and n is 4 to 13 are particularly preferred. When the aryl group has a substituent, the substitution position is not particularly limited as long as substitution is possible. Examples of the substituent include halogen atoms such as fluorine atom, bromine atom and chlorine atom; (C1-C6) alkyl group optionally substituted with halogen atom such as methyl group, trifluoromethyl group, ethyl group and propyl group; And (C1-C6) alkoxy groups such as methoxy group and ethoxy group. The compound represented by the formula (4) may be a single product or a mixture.
Examples of the compound represented by the formula (4) include Prisurf AL (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
クレゾールスルホン酸ホルマリン縮合物としては、例えば、デモールSC-30(花王(株)製)等が挙げられる。 The cresolsulfonic acid formalin condensate in the surfactant (C) contained in the aqueous dispersion for flameproofing of the present invention is metacresolsulfonic acid, paracresolsulfonic acid, orthocresolsulfonic acid or a mixture thereof and formalin. As a salt thereof, a salt that is an alkali metal, ammonium, or the like is included as a counter cation. Examples of the counter cation include lithium, sodium, potassium, ammonium, and the like. Sodium or ammonium is preferred. The cresol sulfonic acid formalin condensate may be a single product or a mixture.
Examples of the cresol sulfonic acid formalin condensate include Demol SC-30 (manufactured by Kao Corporation).
即ち、ハロゲン化合物(A)及びリン酸ナフチルジフェニルエステル化合物(B)は防炎加工用水性分散液中、通常1~70重量%、好ましくは5~50重量%、特に好ましくは5~30重量%の範囲で含有される。又、防炎加工用水性分散液中、ハロゲン化合物(A)とリン酸ナフチルジフェニルエステル化合物(B)の重量比は1:20~20:1が好ましい。
又、防炎加工用水性分散液における、ハロゲン化合物(A)とリン酸トリフェニルエステル化合物(B’)の重量比は1.5:1~20:1の範囲である。ハロゲン化合物(A)及びリン酸トリフェニルエステル化合物(B’)は防炎加工用水性分散液中、通常1~70重量%、好ましくは5~50重量%、特に好ましくは5~30重量%の範囲で含有される。本発明の防炎加工用水性分散液においては、ハロゲン化合物(A)、リン酸ナフチルジフェニルエステル化合物(B)及び界面活性剤(C)、又は、ハロゲン化合物(A)、リン酸トリフェニルエステル化合物(B’)及び界面活性剤(C)を防炎加工用水性分散液中に総量で1~90重量%含有するのが好ましい。 The content ratio of each component in the aqueous dispersion for flameproofing of the present invention is as follows.
That is, the halogen compound (A) and the phosphoric acid naphthyl diphenyl ester compound (B) are usually 1 to 70% by weight, preferably 5 to 50% by weight, particularly preferably 5 to 30% by weight in the aqueous dispersion for flameproofing. It is contained in the range. In the aqueous dispersion for flameproofing, the weight ratio of the halogen compound (A) and the naphthyl diphenyl ester compound (B) is preferably 1:20 to 20: 1.
Further, the weight ratio of the halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) in the aqueous dispersion for flameproofing is in the range of 1.5: 1 to 20: 1. The halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) are usually 1 to 70% by weight, preferably 5 to 50% by weight, particularly preferably 5 to 30% by weight in the aqueous dispersion for flameproofing. Contained in a range. In the aqueous dispersion for flameproofing of the present invention, the halogen compound (A), the phosphoric acid naphthyl diphenyl ester compound (B) and the surfactant (C), or the halogen compound (A), the phosphoric acid triphenyl ester compound The total amount of (B ′) and the surfactant (C) is preferably 1 to 90% by weight in the aqueous dispersion for flameproofing.
界面活性剤(C)として、前記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩とを使用する場合には、前記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩との重量比は、10:1~1:10の範囲が好ましい。 The amount of the surfactant (C) used is usually 5 to 80% by weight, preferably 10%, based on the total amount of the halogen compound (A), the phosphoric acid naphthyl diphenyl ester compound (B) and the optional ultraviolet absorber. It is in the range of ˜50% by weight, particularly preferably 15 to 35% by weight.
When the compound represented by the above formula (3) or a salt thereof and the cresolsulfonic acid formalin condensate or the salt thereof are used as the surfactant (C), the compound represented by the above formula (3) or The weight ratio of the salt to the cresolsulfonic acid formalin condensate or the salt thereof is preferably in the range of 10: 1 to 1:10.
又、本発明の防炎加工用水性分散液は抗菌加工、消臭加工、表面加工等の種々の機能性を付与された繊維にも使用することができ、それにより該機能性を付与された繊維にも防炎加工することができる。 Examples of CDP fibers and polyester fibers include polyethylene terephthalate, polybutylene terephthalate, polyoxyethoxybenzoate, polyethylene naphthalate, cyclohexanedimethylene terephthalate, and other polyester fibers. Examples include, but are not limited to, fibers of materials obtained by copolymerization of dicarboxylic acid components such as adipic acid and sulfoisophthalic acid, and diol components such as propylene glycol, butylene glycol, cyclohexane dimethanol, and diethylene glycol. It is not something.
The aqueous dispersion for flameproofing of the present invention can also be used for fibers having various functionalities such as antibacterial processing, deodorizing processing, surface processing, and the like, thereby imparting the functionality. The fiber can also be flameproofed.
以下の実施例及び比較例に示す各構成成分は必要に応じてサンドグラインダーにて粉砕し、他の成分と共に水に加えて防炎加工用水性分散液を得た。 The compound of the formula (301) is commercially available from Yamamitsu Co., Ltd. under the trade name SANKO-BCA. The compound of formula (302) is commercially available from Hokuko Chemical Co., Ltd. under the trade name TPPO.
Each component shown in the following Examples and Comparative Examples was pulverized with a sand grinder as necessary, and added to water together with other components to obtain an aqueous dispersion for flameproofing.
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 25.0%
リン酸ナフチルジフェニルエステル化合物(B) 5.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 1
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 25.0%
Phosphate naphthyl diphenyl ester compound (B) 5.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸ナフチルジフェニルエステル化合物(B) 15.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 2
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphate naphthyl diphenyl ester compound (B) 15.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 5.0%
リン酸ナフチルジフェニルエステル化合物(B) 25.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 3
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 5.0%
Phosphate naphthyl diphenyl ester compound (B) 25.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸ナフチルジフェニルエステル化合物(B) 15.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 4
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphate naphthyl diphenyl ester compound (B) 15.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 25.0%
リン酸トリフェニルエステル(303) 5.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 5
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 25.0%
Phosphoric acid triphenyl ester (303) 5.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて本発明の防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 20.0%
リン酸トリフェニルエステル(303) 10.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Example 6
An aqueous dispersion for flameproofing of the present invention was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 20.0%
Phosphoric acid triphenyl ester (303) 10.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
式(301)の化合物 15.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 1
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Compound of formula (301) 15.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
式(302)の化合物 15.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 2
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Compound of formula (302) 15.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸トリフェニルエステル(303) 15.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 3
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphoric acid triphenyl ester (303) 15.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸トリフェニルエステル(303) 15.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 4
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphoric acid triphenyl ester (303) 15.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 10.0%
リン酸トリフェニルエステル(303) 20.0%
ニューコールB4-SN(式(3)の化合物) 3.3%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 3.0%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 5
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 10.0%
Phosphoric acid triphenyl ester (303) 20.0%
New Coal B4-SN (compound of formula (3)) 3.3%
Demol SC-30 (Cresolsulfonic acid formalin condensate) 3.0%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸ナフチルジフェニルエステル化合物(B) 15.0%
ニューコールB4-SN(式(3)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 6
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphate naphthyl diphenyl ester compound (B) 15.0%
New Coal B4-SN (compound of formula (3)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸ナフチルジフェニルエステル化合物(B) 15.0%
デモールSC-30(クレゾールスルホン酸ホルマリン縮合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 7
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphate naphthyl diphenyl ester compound (B) 15.0%
DEMAL SC-30 (Cresolsulfonic acid formalin condensate) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 15.0%
リン酸ナフチルジフェニルエステル化合物(B) 15.0%
ノイゲンEA-87(非イオン性界面活性剤) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 8
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 15.0%
Phosphate naphthyl diphenyl ester compound (B) 15.0%
Neugen EA-87 (nonionic surfactant) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
ハロゲン化合物(A) 30.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 9
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Halogen compound (A) 30.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
以下に示す組成を用いて防炎加工用水性分散液を得た。
組成
水 63.0%
リン酸ナフチルジフェニルエステル化合物(B) 30.0%
プライサーフALNa塩(式(4)の化合物) 6.3%
増粘剤 0.5%
消泡剤 0.1%
防カビ剤 0.1%
全量:100.0% Comparative Example 10
An aqueous dispersion for flameproofing was obtained using the composition shown below.
composition
Water 63.0%
Phosphate naphthyl diphenyl ester compound (B) 30.0%
Prisurf ALNa salt (compound of formula (4)) 6.3%
Thickener 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total amount: 100.0%
前記の実施例1~6で調製した各防炎加工用水性分散液を用いて繊維を防炎加工した。同時に、比較例1~10で調製した各防炎加工用水性分散液を用いて同様に繊維を防炎加工した。
即ち、前記の実施例1~6又は比較例1~10で調製した各防炎加工用水性分散液を用い、浸染同浴処理法にて、ポリエステル70%及びCDP30%の混紡繊維の布帛40センチ四方をそれぞれ染色すると同時に防炎加工した。 Example 7
The fibers were flameproofed using each of the flameproofing aqueous dispersions prepared in Examples 1-6. At the same time, the fibers were similarly flameproofed using the aqueous dispersions for flameproofing prepared in Comparative Examples 1 to 10.
That is, using each flameproofing aqueous dispersion prepared in Examples 1 to 6 or Comparative Examples 1 to 10 described above, 40 cm of a blended fiber of 70% polyester and 30% CDP by the same dye bath treatment method. Each side was dyed and fireproofed at the same time.
なお前記の還元洗浄とは以下の操作をいう。即ち、ハイドロサルファイト2g/L、苛性ソーダ2g/L、ノニオン界面活性剤1g/Lの水溶液を調製し、これを80℃に加温した後、防炎加工済の前記の布帛を加えて10分間処理する操作である。 Thereafter, each fabric was subjected to reduction cleaning, and then heat-treated at 170 ° C. for 60 seconds. Further, according to JIS K3371, a weak alkaline first-class detergent was used at a rate of 1 g / L, a bath ratio of 1:40, and each fabric was washed with water at 60 ° C. ± 2 ° C. for 15 minutes, and then 40 ° C. ± 2 ° C. And 5 minutes of rinsing for 5 minutes, centrifugal dehydration for 2 minutes, and then water washing with hot air drying at 60 ° C. ± 5 ° C. as one cycle for 5 cycles to obtain a flameproofed fiber.
The above-described reduction cleaning refers to the following operation. That is, an aqueous solution of hydrosulfite 2 g / L, caustic soda 2 g / L, and nonionic surfactant 1 g / L was prepared, heated to 80 ° C., and then added with the above flameproofed fabric for 10 minutes. The operation to process.
難燃性および分散安定性試験
実施例7の操作で得た16種類の混紡繊維布帛と未処理布を試験片とし、これらについて燃焼性試験を行った。また、前記の実施例1~6又は比較例1~10で調製した各防炎加工用水性分散液の分散安定性試験を行った。 Test example 1
Flame Retardancy and Dispersion Stability Test 16 kinds of blended fiber fabric and untreated fabric obtained by the operation of Example 7 were used as test pieces, and a flammability test was conducted on these. Further, a dispersion stability test of each aqueous dispersion for flameproofing prepared in Examples 1 to 6 or Comparative Examples 1 to 10 was performed.
燃焼性試験の試験方法:
消防法JIS L1091A-1法(45度ミクロバーナー法)にて試験を行い、以下の評価を行った。その結果を下記表に示す。 (1) Test method
Test method for flammability test :
Tests were conducted according to the Fire Service Act JIS L1091A-1 method (45 degree micro burner method), and the following evaluations were made. The results are shown in the table below.
残炎時間が3秒以下の場合を合格とし、測定回数でその測定中における合格回数を除した数値を合格率として記載した。小数点以下は四捨五入し単位は%である。合格率の高い方が防炎性能が高い。合格率の後ろの括弧書きは合格率の算出に使用した合格回数と測定回数であり、「(合格回数/測定回数)」で表示した。 Evaluation A: Pass rate :
A case where the after flame time was 3 seconds or less was regarded as acceptable, and a numerical value obtained by dividing the number of times of acceptance during the measurement by the number of times of measurement was described as the acceptance rate. The fractional part is rounded off and the unit is%. The higher the acceptance rate, the higher the flameproof performance. The parentheses after the pass rate are the number of passes and the number of measurements used to calculate the pass rate, and are indicated by “(pass times / measurement times)”.
評価Aにて測定した残炎時間の総合計を測定回数で除することにより、平均残炎時間を算出した。単位は秒である。平均残炎時間の短い方が防炎性能が高い。 Evaluation B: Average after flame time :
The average afterflame time was calculated by dividing the total afterflame time measured in Evaluation A by the number of measurements. The unit is seconds. The shorter the average afterflame time, the higher the flameproof performance.
得られた防炎加工用水性分散液を60℃恒温槽内に2時間置き、その後室温にて1日放置後に分散体が、分離、結晶の析出等をしてないもの「○」、分離、結晶等の析出があるもの「×」とした。 Evaluation of dispersion stability :
The obtained aqueous dispersion for flameproofing was placed in a constant temperature bath at 60 ° C. for 2 hours, and after standing for 1 day at room temperature, the dispersion was not separated, crystal precipitated, etc. “×” indicates that crystals or the like are precipitated.
評価Aの合格率、評価Bの平均残炎時間、分散安定性の試験結果の全体から本発明の防炎加工用水性分散液の優位性は明らかである。 From the results of Table 1, the pass rate of evaluation A is 96 to 100% of the aqueous dispersion for flameproofing of Examples 1 to 6 of the present invention, whereas the aqueous dispersion for flameproofing of each comparative example is In the case of an aqueous dispersion for flameproofing that does not use a mixture of both the halogen compound (A) and the phosphoric acid naphthyl diphenyl ester compound (B) (comparative examples 1 to 3, 9, 10) is 64 to 66%, and the aqueous dispersion for flameproofing of Examples of the present invention has a higher pass rate. Moreover, the pass rate of evaluation A of the aqueous dispersion for flameproofing of Examples 5 and 6 containing the halogen compound (A) and the phosphoric acid triphenyl ester compound (B ′) in the composition ratio of the present invention is 96%. 100%, but 64 to 80% of the aqueous dispersion for flameproofing of Comparative Examples 3 to 5 containing both of them at 1: 1 or 1: 2 and pass the aqueous dispersion for flameproofing of the present invention. The rate is high. Regarding the average afterflame time of Evaluation B, the aqueous dispersions for flameproofing of Examples 1 to 6 were 0.7 to 1.8, whereas the aqueous dispersions for flameproofing of each comparative example were 2 The average afterflame time of the aqueous dispersion for flameproofing of Comparative Example is long. Further, the dispersion stability is stable in the case of an aqueous dispersion for flameproofing using only the halogen compound (A) or the naphthyl diphenyl ester compound (B) (Comparative Examples 9 and 10), but mixed. In the case of an aqueous dispersion for flameproofing (Comparative Examples 6 to 8), the stability is deteriorated unless the surfactant (C) used in the present invention is used.
The superiority of the aqueous dispersion for flameproofing of the present invention is clear from the overall pass results of evaluation A, average after-flame time of evaluation B, and dispersion stability test results.
Claims (10)
- 下記式(1)で表されるハロゲン化合物(A)、下記式(2)で表されるリン酸ナフチルジフェニルエステル化合物(B)及び界面活性剤(C)を含む防炎加工用水性分散液であって、該界面活性剤(C)が下記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は下記式(4)で表される化合物若しくはその塩である、防炎加工用水性分散液。
- ハロゲン化合物(A)とリン酸ナフチルジフェニルエステル化合物(B)の重量比が1:20~20:1の範囲である請求項1に記載の防炎加工用水性分散液。 The aqueous dispersion for flameproofing according to claim 1, wherein the weight ratio of the halogen compound (A) and the naphthyl diphenyl ester compound (B) is in the range of 1:20 to 20: 1.
- 下記式(1)で表されるハロゲン化合物(A)、下記式(303)で表されるリン酸トリフェニルエステル化合物(B’)及び界面活性剤(C)を含む防炎加工用水性分散液であって、ハロゲン化合物(A)とリン酸トリフェニルエステル化合物(B’)の重量比が1.5:1~20:1の範囲であり、該界面活性剤(C)が下記式(3)で表される化合物若しくはその塩とクレゾールスルホン酸ホルマリン縮合物若しくはその塩、又は下記式(4)で表される化合物若しくはその塩である防炎加工用水性分散液。
- ハロゲン化合物(A)、リン酸ナフチルジフェニルエステル化合物(B)及び界面活性剤(C)、又は、ハロゲン化合物(A)、リン酸トリフェニルエステル化合物(B’)及び界面活性剤(C)を防炎加工用水性分散液中に総量で1~90重量%含有する請求項1~3のいずれか一項に記載の防炎加工用水性分散液。 Halogen compound (A), phosphate naphthyl diphenyl ester compound (B) and surfactant (C), or halogen compound (A), phosphate triphenyl ester compound (B ′) and surfactant (C) are prevented. The aqueous dispersion for flameproofing according to any one of claims 1 to 3, which is contained in a total amount of 1 to 90% by weight in the aqueous dispersion for flameproofing.
- 更に、紫外線吸収剤を含有する請求項1~4のいずれか一項に記載の防炎加工用水性分散液。 The aqueous dispersion for flameproofing according to any one of claims 1 to 4, further comprising an ultraviolet absorber.
- 繊維の防炎加工に使用する請求項1~5のいずれか一項に記載の防炎加工用水性分散液。 6. The aqueous dispersion for flameproofing according to any one of claims 1 to 5, which is used for flameproofing of fibers.
- 繊維がポリエステル繊維である請求項6に記載の防炎加工用水性分散液。 The aqueous dispersion for flameproofing according to claim 6, wherein the fibers are polyester fibers.
- ポリエステル繊維がカチオン可染型ポリエステル繊維又はカチオン可染型ポリエステル繊維を含有する混紡繊維である請求項7に記載の防炎加工用水性分散液。 The aqueous dispersion for flameproofing according to claim 7, wherein the polyester fiber is a cation dyeable polyester fiber or a blended fiber containing a cation dyeable polyester fiber.
- 請求項1~8のいずれか一項に記載の防炎加工用水性分散液を用いることを含む繊維の防炎加工方法。 A method for flameproofing a fiber, comprising using the aqueous dispersion for flameproofing according to any one of claims 1 to 8.
- 請求項9に記載の方法により防炎加工された繊維。 A fiber that has been flameproofed by the method according to claim 9.
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JP2013014853A (en) * | 2011-07-01 | 2013-01-24 | Nicca Chemical Co Ltd | Flame retardant for polyester-based fiber, flame-retardant polyester-based fiber using the same and method for producing the same |
JP2013079472A (en) * | 2011-10-05 | 2013-05-02 | Nicca Chemical Co Ltd | Flame retardant agent for polyester-based fiber, flame-retardant processing method for polyester-based fiber, and flame-retardant polyester-based fiber |
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JP2009203595A (en) * | 2007-09-26 | 2009-09-10 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame retarding processing agent for polyester fiber and processing method thereof |
JP2011032588A (en) * | 2009-07-29 | 2011-02-17 | Komatsu Seiren Co Ltd | Flame retardant agent and flame retardant method for polyester fiber product |
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JPWO2009119789A1 (en) * | 2008-03-28 | 2011-07-28 | 日本化薬株式会社 | Aqueous dispersion of organophosphorus compound and flameproofing method using the same |
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JP2009203595A (en) * | 2007-09-26 | 2009-09-10 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame retarding processing agent for polyester fiber and processing method thereof |
JP2011032588A (en) * | 2009-07-29 | 2011-02-17 | Komatsu Seiren Co Ltd | Flame retardant agent and flame retardant method for polyester fiber product |
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JP2013014853A (en) * | 2011-07-01 | 2013-01-24 | Nicca Chemical Co Ltd | Flame retardant for polyester-based fiber, flame-retardant polyester-based fiber using the same and method for producing the same |
JP2013079472A (en) * | 2011-10-05 | 2013-05-02 | Nicca Chemical Co Ltd | Flame retardant agent for polyester-based fiber, flame-retardant processing method for polyester-based fiber, and flame-retardant polyester-based fiber |
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