JP3883996B2 - Flame retardant for polyester synthetic fiber - Google Patents

Description

  The present invention relates to a flame retardant for polyester-based synthetic fibers. More particularly, the present invention relates to a non-halogen post-processing flame retardant.

Conventionally, as a flame retardant for post-processing used for cotton and yarn made of polyester-based synthetic fibers, and knitted fabrics or nonwoven fabrics made of them, an aqueous dispersion of hexabromocyclododecane (for example, see Patent Document 1), etc. Halogen compounds have been used, but halogen compounds have become a problem from the viewpoint of environmental protection, and recently, non-halogen flame retardants have been demanded. Various types of phosphorus compounds have been studied as flame retardant components that replace halogen compounds, and for example, polyphosphate compounds (see Patent Documents 2 and -3) have been proposed. However, these polyphosphates are usually emulsified and dispersed, and then added to a dye bath or padding bath to give them to polyester-based synthetic fibers. It was difficult to make an emulsified dispersion with good stability and good stability.
JP 57-137377 A Japanese Patent Publication No. 2-18336 JP-A-8-41781

All of the conventional polyphosphate flame retardants have insufficient storage stability of the emulsified dispersion. Further, the durability of the flame retardant effect is insufficient, and there is a problem that the flame retardant effect is lowered after washing or dry cleaning of a fiber subjected to flame retardant treatment, such as yarn, knitted fabric or nonwoven fabric.
An object of the present invention is to provide a flame retardant for a polyester-based synthetic fiber that uses a polyphosphate compound and has good storage stability and can impart durable flame retardancy.

  As a result of intensive studies to achieve the above object, the present inventors have good emulsion stability, as a result, good storage stability, and good flame retardancy and flame retardant effect for polyester synthetic fibers. The present inventors have found a flame retardant imparting the durability of the present invention and have reached the present invention.

  That is, the present invention provides phosphoryl using an esterified product (A) obtained from an alkylene oxide adduct (a) of a naturally derived oil and fat having two or more hydroxyl groups and a dicarboxylic acid or an ester-forming derivative (b) thereof. A flame retardant for polyester synthetic fibers obtained by emulsifying and dispersing a condensate (B) of a trihalide and a monovalent and / or divalent phenol compound, a flame retardant polyester synthetic fiber comprising the flame retardant, and the flame retardant It is a polyester-based synthetic fiber product made of flame-retardant polyester-based synthetic fiber.

(1) Although the flame retardant of the present invention is in an emulsified form, it is difficult to cause aggregation and separation, has long-term emulsion stability, and has long-term storage stability.
(2) The polyester-based synthetic fiber that has been post-processed and flame-retardant treated with the flame retardant of the present invention is excellent in flame retardancy and is excellent in durability of flame retardancy, such as washing resistance and dry cleaning resistance. .
(3) Since the flame retardant of the present invention does not contain a halogen atom, it does not generate a halogenated gas when the polyester synthetic fiber product is burned, and does not adversely affect the safety of the environment and the human body.

  In the present invention, among the naturally-derived oils and fats having two or more hydroxyl groups constituting (a), preferred are oils and fats having 2 to 3 or more, particularly 2 or 3 hydroxyl groups. As these oils and fats, for example, Asagaaceae seed oil (number of hydroxyl groups = 2 on average), oilseed seed oil (number of hydroxyl groups = 2 on average), castor oil (number of hydroxyl groups = 3 on average) , Kamala oil (number of hydroxyl groups = 3 on average), wool wax (number of hydroxyl groups = 2 on average), hydrogenated products thereof, and combinations of two or more of these, storage of flame retardants From the viewpoint of stability, castor oil or hardened castor oil is preferable.

  (A) is an alkylene oxide (hereinafter abbreviated as AO) adduct of naturally-occurring oils and fats having two or more hydroxyl groups, and the number of moles of AO added to 1 mol of the oils and fats is preferably 10 to 70 mol, More preferably, it is 20-60 mol. If the AO addition mole number is 10 to 70, the storage stability of the flame retardant tends to be further improved.

  Examples of AO include alkylene oxides having 2 and 3 carbon atoms such as ethylene oxide (hereinafter abbreviated as EO) and propylene oxide (hereinafter abbreviated as PO). Preferred is EO alone or a combination of EO and PO, and more preferred is EO alone. The preferred weight ratio of EO based on the weight of AO when used in combination is 80% or more, particularly 90% or more.

Of the dicarboxylic acid or its ester-forming derivative (b) in the present invention, examples of the dicarboxylic acid include aromatic dicarboxylic acids, aliphatic dicarboxylic acids, and alicyclic dicarboxylic acids.
Examples of the aromatic dicarboxylic acid include dicarboxylic acids having 8 to 16 carbon atoms, such as terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid (2,6- and / or 2,7-form), diphenyl-4,4′-dicarboxylic acid. , Diphenoxyethanedicarboxylic acid and 3-sulfoisophthalic acid.

  Examples of the aliphatic dicarboxylic acid include saturated dicarboxylic acids having 2 to 50 carbon atoms such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid and decanedicarboxylic acid. Examples include acids such as maleic acid, fumaric acid, itaconic acid and dimer acid.

  As the alicyclic dicarboxylic acid, those having 6 to 20 carbon atoms such as 1,3-cyclobutanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, Examples include 1,3-dicarboxymethylcyclohexane, 1,4-dicarboxymethylcyclohexyl, and dicyclohexyl-4,4′-dicarboxylic acid.

  Of the above dicarboxylic acids, aromatic dicarboxylic acids (particularly terephthalic acid and isophthalic acid) and combinations thereof with other dicarboxylic acids (usually 100/0 to 65 by weight) are preferred from the viewpoint of storage stability of the flame retardant. / 35, preferably 100/0 to 80/20).

Examples of ester-forming derivatives of dicarboxylic acids include lower alkyl (C1-4) esters and carboxylic anhydrides.
Examples of the lower alkyl ester include dimethyl terephthalic acid, dimethyl isophthalic acid, dimethyl naphthalene dicarboxylic acid (2,6- and / or 2,7-isomer), dimethyl itaconic acid, dimethylcyclohexanedicarboxylic acid (1,4- and / or 1). , 3- isomer) and the like, and preferred are dimethyl terephthalic acid and dimethyl isophthalic acid, particularly dimethyl terephthalic acid.

  Examples of the carboxylic anhydride include carboxylic anhydrides having 4 to 20 carbon atoms, such as maleic anhydride, itaconic anhydride, and phthalic anhydride, and preferred are maleic anhydride, itaconic anhydride, particularly maleic anhydride.

The esterified product (A) can be obtained by the esterification reaction or transesterification reaction of (a) and (b). In these reactions, the equivalent ratio of hydroxyl group / carboxyl group (carboxyl group also includes a carboxyl group derived from an ester-forming derivative) is usually 1 / 0.1 to 1/1, and the storage stability of the flame retardant From the viewpoint, it is preferably 1 / 0.15 to 1 / 0.95, and the terminal group of the obtained esterified product is preferably a hydroxyl group.
The number average molecular weight (measured by gel permeation chromatography (hereinafter abbreviated as GPC)) of (A) is preferably 500 to 5,000, more preferably 700 to 4,000. Within this range, the storage stability of the flame retardant tends to be further improved.

The transesterification reaction and the esterification reaction are usually performed in the presence of a catalyst.
Transesterification catalysts include metal compounds such as lithium oxide, lithium methylate, lithium ethylate, lithium acetate, sodium methylate, sodium ethylate, sodium formate, sodium acetate, sodium acetate and potassium acetate, zinc formate, acetic acid Zinc compounds such as zinc, zinc propionate and zinc borate, manganese compounds such as manganese acetate and manganese borate, cobalt compounds such as cobalt formate, cobalt chloride and cobalt acetate, alkaline earth such as calcium acetate, magnesium acetate and barium acetate Metal compounds, titanium compounds such as titanium isopropoxide and titanium butoxide, and tin compounds such as dibutyltin oxide, and two or more of these may be used in combination.
The esterification reaction includes the same metal compound and / or acid catalyst as used in the transesterification reaction, such as paratoluenesulfonic acid, methanesulfonic acid, and sulfuric acid, and two or more of these may be used in combination.
The reaction time for the transesterification or esterification reaction is usually 1 to 20 hours, preferably 2 to 10 hours. The end point of the reaction can be confirmed by the saponification value or the hydroxyl value of the esterified product obtained. Usually, the saponification value is 200 to 10, preferably 150 to 20, and more preferably 100 to 25 from the viewpoint of emulsifying power. The hydroxyl value is usually 5 to 100, preferably 10 to 80, and further 15 to 70. The (saponification value + hydroxyl value) is usually 10 to 250, preferably 20 to 200.

(B) in the present invention is a condensate of a phosphoryl trihalide and a monovalent and / or divalent phenol compound.
Phosphoryl trihalides include phosphoryl trichloride, phosphoryl tribromide and phosphoryl triiodide, with phosphoryl trichloride being preferred.
Examples of the monohydric phenol compound include monohydric phenol compounds having 6 to 18 carbon atoms, such as phenol, cresol, xylenol and p-ethylphenol.
Examples of the dihydric phenol compound include C6-C18 dihydric phenol compounds such as resorcinol, catechol and hydroquinone.
Examples of the phenolic compound include one or more monohydric phenolic compounds, one or more dihydric phenolic compounds, or a combination thereof. Preferred are one or more monohydric phenolic compounds and bivalent compounds. A combined use with one or more phenolic compounds, particularly a combined use of phenol and resorcinol.

  Among (B), the condensate (B1) of phosphoryl trichloride, phenol and resorcinol is particularly preferable from the viewpoint of flame retardancy and storage stability of the flame retardant.

In (B), a Lewis acid catalyst is added to a phosphoryl trihalide, a monohydric phenol compound and / or a dihydric phenol compound, and the reaction is performed by heating while removing by-product hydrogen halide outside the system. Is obtained. Examples of the Lewis acid catalyst include magnesium chloride. The reaction temperature is usually 100 to 200 ° C. (preferably 120 to 180 ° C.), and the reaction time is 2 to 10 hours.
The molar ratio charged between the phosphoryl trihalide and the phenol compound is usually 1 to 1.2 / 1.45 to 1.55, preferably 1 to 1.1 / 1.5.
In addition, the charged molar ratio of phosphoryl trichloride, phenol and resorcinol in the production of (B1) is usually 1 to 1.2 / 1 / 0.45 to 0.55, preferably 1 to 1.1 / 1. /0.5.

  (B1) is usually (3-hydroxyphenyl) diphenyl phosphate, triphenyl phosphate, di (3-hydroxyphenyl) phenyl phosphate, and 1,3-phenylenebis (diphenyl phosphate) [phosphoric acid (3 -Hydroxyphenyl) phenyl], which is commercially available under trade names such as “CR733S” manufactured by Daihachi Chemical Industry Co., Ltd.

  In the present invention, the content of (B) based on the weight of the flame retardant is preferably 20% or more from the viewpoint of economy during production or transportation (in the following, unless otherwise specified,% represents% by weight), Further, it is 25% or more, particularly 30% or more, and is preferably 80% or less, more preferably 70% or less, particularly preferably 60% or less from the viewpoint of easy handling of the flame retardant.

In the flame retardant of the present invention, (A) is preferably 5 to 40 parts relative to 100 parts of (B) (in the following, unless otherwise specified, parts represent parts by weight), and 10 to 30 parts. More preferably, it is a part. If (A) is 5 parts or more, the storage stability of the flame retardant is likely to be further improved, and if it is 40 parts or less, the flame retardancy is likely to be improved.
The total content of (A) and (B) based on the weight of the flame retardant of the present invention is preferably 21 to 70%, more preferably 30 to 60%.

  The flame retardant of the present invention may contain a nonionic surfactant and / or an anionic surfactant other than (A) as required, as long as the effect is not inhibited.

  Examples of the nonionic surfactant include an AO addition type nonionic surfactant [higher alcohol (carbon number 8 to 18), higher fatty acid (carbon number 12 to 24), higher alkylamine (carbon number 8 to 24), etc. AO added directly to AO [weight average molecular weight (measured by GPC, hereinafter abbreviated as Mw) = 158 to 200,000]; polyalkylene glycol obtained by adding AO to glycol (Mw 150 to 6,000) A higher fatty acid (carbon number 8 to 60, for example, ethylene glycol, propylene glycol, glycerin, pentaerythritol, sorbitan) and a higher fatty acid (carbon number). 12 to 24, for example, lauric acid, stearic acid) is reacted with esterified product obtained from AO Added (Mw 250 to 30,000); higher fatty acid amide added with AO (Mw 200 to 30,000); polyvalent (divalent to octavalent or higher) alcohol alkyl (carbon number 8 to 60) ) Ether added with AO (Mw 120 to 30,000, etc.)] and polyvalent (divalent to octavalent or higher) alcohol (carbon number 7 to 60) type nonionic surfactant [polyhydric alcohol Fatty acid (carbon number 8 to 60) ester, polyvalent (divalent to octavalent or higher) alcohol alkyl (carbon number 7 to 60) ether, fatty acid (carbon number 8 to 60) alkanolamide, etc.). .

  Examples of the anionic surfactant include carboxylic acids (saturated or unsaturated fatty acids having 8 to 22 carbon atoms) or salts thereof (salts such as sodium, potassium, ammonium, and alkanolamine), and salts of carboxymethylates (8 carbon atoms). -16 fatty alcohol and / or a salt of carboxymethylated product such as an AO (1-10 mol) adduct thereof), sulfate ester salt [higher alcohol sulfate ester (sulfate ester of fatty acid alcohol having 8 to 18 carbon atoms) Salts)], higher alkyl ether sulfates [sulfate esters of AO (1-10 mol) adducts of fatty acid alcohols having 8 to 18 carbon atoms], sulfated oils (natural unsaturated oils or unsaturated waxes) ) And sulfated fatty acid ester (unsaturated fatty acid lower alcohol ester) Sulfated olefins (sulfurized olefins having 12 to 18 carbon atoms and neutralized), sulfonates [alkylbenzenesulfonates, alkylnaphthalenesulfonates, sulfosuccinic acid diester type , Α-olefin (carbon number 12-18) sulfonate, Igepon T type, etc.] and phosphate ester salt [higher alcohol (carbon number 8-60) phosphate ester salt, higher alcohol (carbon number 8-60) AO Adduct phosphate ester salt, alkyl (carbon number 8 to 60) phenol AO adduct phosphate ester salt, etc.].

  The amount of these surfactants to be added is usually 0 to 50 parts, preferably 0.001 to 50 parts, more preferably 0.05 to 35 parts, relative to 100 parts of (A). If 0.001 part or more is blended, the storage stability of the flame retardant tends to be further improved, and if it is 50 parts or less, the durability of the flame retardant effect is rarely lowered.

  There is no restriction | limiting in particular in the manufacturing method of the flame retardant of this invention, For example, by adding water gradually, stirring the mixture of (A) (and other surfactant if necessary) and (B). , (B) can be emulsified and dispersed. A homogenizer etc. can also be used for emulsification dispersion.

The flame retardant of the present invention is obtained by emulsifying and dispersing (B) in water, and the volume average particle size of (B) in the flame retardant is the adsorptivity to polyester fibers and the flame retardancy after washing and after dry cleaning. In view of the above, it is preferably in the range of 0.01 to 5 μm, more preferably in the range of 0.1 to 2 μm. If it is 0.01 μm or more, (B) is easily adsorbed to the polyester-based synthetic fiber, and if it is 5 μm or less, (B) penetrates into the polyester-based synthetic fiber, and has flame retardancy after washing and after dry cleaning. Especially good. The volume average particle size can be measured by a laser diffraction particle size distribution measurement method (for example, a laser diffraction particle size distribution measurement device LA-700 manufactured by Horiba, Ltd.).
The viscosity of the flame retardant of the present invention is preferably 5 to 500 mPa · s, more preferably 10 to 400 mPa · s at 25 ° C. The viscosity can be measured with a BL type viscometer.

The composition of the polyester synthetic fiber that can be flame-retardant processed with the flame retardant of the present invention includes polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate / isophthalate. Polyethylene terephthalate / 5-sodium sulfoisophthalate, polyethylene / polyoxybenzoyl terephthalate, and polybutylene terephthalate / isophthalate.
Examples of the polyester synthetic fiber include cotton, yarn, tow, top, casset, knitted fabric, and non-woven fabric.
The polyester-based synthetic fiber according to the present invention includes a blended and woven fabric using two or more kinds of polyester-based synthetic fibers having different compositions, or the above-mentioned polyester-based synthetic fiber and other natural materials (cotton, hemp, wool, etc.), Semi-synthetic (rayon, acetate, etc.), synthetic (nylon, acrylic, etc.) and / or inorganic (carbon, glass, ceramics, asbestos, metal, etc.) blended and woven fabrics and the like are included.

The flame retardant polyester synthetic fiber of the present invention can be obtained by treating the flame retardant of the present invention with a known technique into a polyester synthetic fiber.
For example, when dyeing polyester-based synthetic fibers (for example, woven fabric) using a liquid dyeing machine, the flame retardant is added to the dye bath, and the dyeing and the flame retardant treatment are performed simultaneously (wash bath and bath treatment method). Is mentioned. In this case, the fibers are immersed and the treatment is performed at a temperature of 80 ° C. to 130 ° C. for several minutes to 60 minutes. Then, after dehydrating using a centrifugal dehydrator if necessary, heat treatment is performed for about several minutes at a temperature of 120 ° C. to 180 ° C. using a tenter or the like.

As another treatment method, polyester-based synthetic fibers (for example, woven fabric) are dipped in a flame retardant, dried at a temperature of 100 ° C. to 140 ° C. for several minutes, and further heated at a temperature of 120 ° C. to 180 ° C. with a tenter or the like. The pad-dry method in which heat treatment is performed for several minutes at the same time; and the spray method in which the flame retardant is sprayed on fibers (for example, woven fabric), followed by drying at a temperature of 100 ° C. to 140 ° C. for several minutes, and further a tenter, etc. The method of performing heat treatment at a temperature of 120 ° C. to 180 ° C. for about several minutes.
Of these, the dye bath and bath treatment method is preferred from the viewpoint of the durability of the flame retardant effect after washing and after dry cleaning.

The flame retardant of the present invention is preferably attached in an amount of 0.1 to 30% by dry weight with respect to the weight of the polyester synthetic fiber. From the viewpoint of flame retardancy and friction fastness, 1 to 25% is more preferable. If 0.1% or more is adhered, the flame retardancy tends to be easily exerted, and if it is 30% or less, the friction fastness is rarely impaired.
The adhesion amount of the flame retardant can be calculated by subtracting the weight of the fabric before the flame retardant treatment from the weight of the fiber after the flame retardant treatment, drying and heat treatment.

The flame retardant of the present invention may be used in combination with other fiber processing agents and / or stabilizers. Examples of such fiber processing agents and stabilizers include softeners (silicone emulsions such as “Saffanol N-750” manufactured by Sanyo Chemical Industries, Ltd.) and water absorbing processing agents (polyester resin emulsions such as “Permarin MR- manufactured by Sanyo Chemical Industries, Ltd.”). 100 "), antistatic agents (phosphate salt surfactants such as" Sunstat KT-600 "manufactured by Sanyo Chemical Industries), water and oil repellents (paraffinic wax such as" Isotol H "manufactured by Sanyo Chemical Industries) , Anti-slip agents (colloidal silica such as “Permarine SCC-A” manufactured by Sanyo Chemical Industries), hard finishes, texture modifiers, preservatives, antioxidants, pH adjusters, etc. It can be used in the same bath or in another bath.
The amount of these other fiber processing agents and stabilizers used is preferably 30% or less, more preferably 15% or less, based on the weight of the flame retardant of the present invention.

  The polyester-based synthetic fiber obtained by treating with the flame retardant of the present invention includes seats (seats for transportation such as automobiles, railways, ships and airplanes, seats for public facilities such as theaters, hospitals and hotels, and households) Textiles such as seats, seat covers, curtains, roll curtains, interior materials (wall / ceiling cloth, shoji paper, carpets, etc.), paddles, building curing sheets, protective nets, and tents.

Hereinafter, the present invention will be further described with reference to examples, but the present invention is not limited thereto. In the examples, the ratio indicates a weight ratio.
The volume average particle diameter was measured with a laser diffraction particle size distribution analyzer LA-700 manufactured by Horiba.

Example 1
A glass reactor equipped with a stirrer, a thermometer and a cooling tube was charged with 430 parts of an EO43 mole adduct of castor oil, 33 parts of dimethylterephthalic acid and 1 part of manganese acetate, and mixed at 160 to 180 ° C. at normal pressure. Transesterification was carried out by heating for a period of time to remove almost the theoretical amount of methanol to obtain 452 parts of an esterified product (A-1) having a saponification number of 95 and a hydroxyl number of 35. (A-1) To a mixture of 60 parts and “CR-733S” (B-1) 400 parts manufactured by Daihachi Chemical Industry Co., Ltd., 540 parts of water was added little by little with stirring, and the flame retardant “S1” was added. Got. “S1” was a milky white emulsion having a concentration of 46%, a viscosity of 45 mPa · s (25 ° C.), and a volume average particle size of 0.25 μm.

Example 2
430 parts of castor oil EO 43 mol adduct, 50 parts of dimethyl 5-sodiumsulfoisophthalate and 1 part of manganese acetate were charged in the same reaction vessel as in Example 1, and heated at 160 to 180 ° C. for 6 hours at normal pressure. The ester exchange reaction was carried out to remove almost the theoretical amount of methanol to obtain 470 parts of an esterified product (A-2) having a saponification number of 95 and a hydroxyl number of 35. In the same manner as in Production Example 1, 500 parts of water was gradually added to a mixture of 50 parts of (A-2) and 450 parts of (B-1) while stirring and emulsified to obtain a flame retardant “S2”. “S2” was a milky white emulsion having a concentration of 50%, a viscosity of 180 mPa · s (25 ° C.), and a volume average particle size of 0.2 μm.

Example 3
In a reaction vessel similar to that in Example 1, 350 parts of EO 30 mol adduct of hardened castor oil, 50 parts of dimethyl 5-sodium sulfoisophthalate and 1 part of manganese acetate were charged and mixed, and heated at 160 to 180 ° C. for 6 hours at normal pressure. Then, a transesterification reaction was carried out to remove almost the theoretical amount of methanol to obtain 390 parts of an esterified product (A-3) having a saponification number of 9 and a hydroxyl number of 3. In the same manner as in Production Example 1, 500 parts of water was gradually added to a mixture of 50 parts of (A-3) and 400 parts of (B-1) while stirring and emulsified and dispersed to obtain flame retardant “S3”. “S3” was a milky white emulsion having a concentration of 45%, a viscosity of 63 mPa · s (25 ° C.), and a volume average particle size of 0.2 μm.

Comparative Example 1
Example 1 except that 30 parts of nonylphenol EO 15 mole adduct and 20 parts of lauryl alcohol EO 20 mole adduct were used in place of (A-1), 450 parts were used for (B-1), and 500 parts were used for water. In the same manner, a comparative flame retardant “X1” was obtained. “X1” was a milky white emulsion having a concentration of 50%, a viscosity of 185 mPa · s (25 ° C.), and a volume average particle size of 1.2 microns.

Comparative Example 2
A flame retardant for comparison in the same manner as in Production Example 1 except that 50 parts of lauryl alcohol EO 20 mol adduct was used instead of (A-1), 450 parts of (B-1) and 500 parts of water were used. “X2” was obtained. “X2” was a milky white emulsion having a concentration of 50%, a viscosity of 140 mPa · s (25 ° C.), and a volume average particle size of 0.8 microns.

About the above flame retardant, the storage stability of the emulsion after 1-month storage at 40 degreeC was evaluated. The results are shown in Table 1.
In the evaluation method, the volume average particle size after storage for 1 month at 40 ° C. was measured, and the appearance of the emulsion was visually observed.
Appearance criteria are ○: milky white emulsion
Δ: Emulsion with boundary between upper and lower layers recognized
X: Separated into three layers, upper and lower layers are transparent, intermediate layer is emulsion

Flame Retardancy Test Evaluation Method After scouring a polyester woven fabric of 300 g / m2 by a conventional method and drying as a test cloth, 1
What was heat-set at 80 ° C. for 1 minute was used.
As a washing bath, dye [Kayalon Polyester Navy Bule 2R-SF (made by Nippon Kayaku)] 2% o. w. f. (Abbreviation of “on the weight of fiber”), dispersive leveling agent [Ionette RAP-250 (manufactured by Sanyo Chemical Industries)] 0.5 g / l, flame retardant 15% (15% as an emulsion) o. w. f. In addition, a washing bath composed of water and water was prepared, and the dyeing of the test cloth and the flame retardant treatment were simultaneously performed at a bath ratio of 1:10.
The dyeing machine was processed at 130 ° C. for 30 minutes using a color master (Aoi dyeing machine dyeing machine), washed with water, dried (100 ° C. × 3 minutes), and further heat-treated (170 ° C. × 1 minute).
About the obtained flame-retardant polyester woven fabric, the adhesion amount of the flame retardant and the flame retardance test were done with the following test method. The difficulty test was performed initially, after washing and after dry cleaning.
The results are shown in Table 1. The “blank” in Table 1 is obtained by scouring a 300 g / m 2 polyester woven fabric and drying it, followed by heat setting at 180 ° C. for 1 minute.
(1) Amount of flame retardant attached Dye flame retardant treatment of weight (g) obtained by subtracting weight (g) of fabric before dye flame retardant treatment from weight (g) of fabric after dye flame retardant treatment, drying and heat treatment Expressed as a percentage of the previous fabric weight (g). (2) Flame retardance test It evaluated by the JISL 1091D method (flame-contacting test). It shows that there is a flame-retardant effect, so that the number of times of flame contact is large.
<How to wash>
It carried out according to JIS L 1042 method.
<Dry cleaning method>
It implemented according to JISL1018 method.

  The polyester-based synthetic fiber flame-treated with the flame retardant of the present invention can be suitably used as a polyester-based synthetic fiber product for seats, interior materials, building curing, protective nets, tents or canvas. .

Claims (8)

Using an alkylene oxide adduct (a) of a naturally derived oil or fat having two or more hydroxyl groups and an esterified product (A) obtained from a dicarboxylic acid or an ester-forming derivative thereof (b), phosphoryl trihalide and 1 A flame retardant for polyester synthetic fibers obtained by emulsifying and dispersing a condensate (B) with a monovalent and / or divalent phenolic compound. The flame retardant according to claim 1, wherein (a) is an alkylene oxide adduct of castor oil or hydrogenated castor oil. The flame retardant according to claim 1 or 2, wherein the number of moles of alkylene oxide added in (a) is 10 to 70 moles. The flame retardant according to any one of claims 1 to 3, wherein the alkylene oxide is ethylene oxide. The flame retardant according to any one of claims 1 to 4, wherein (b) is at least one selected from the group consisting of terephthalic acid, dimethyl terephthalic acid, and ester-forming derivatives thereof. The flame retardant according to any one of claims 1 to 5, wherein (B) is a condensate (B1) of phosphoryl trichloride, phenol and resorcinol. A flame retardant polyester synthetic fiber obtained by heat-treating the flame retardant according to any one of claims 1 to 6 in a dry weight of 0.1 to 30% by weight to a polyester synthetic fiber. A polyester-based synthetic fiber product for seats, interior materials, building curing, protective nets, tents, or canvas, comprising the flame-retardant polyester-based synthetic fiber according to claim 7.