JPH0835179A - Method of treating polyester fiber - Google Patents

Abstract

(57) [Summary] [Objective] The object of the present invention is to solve the problems of toxicity of epoxy compounds and workability of isocyanate which are concerned in the adhesion between polyester fiber and rubbers, and to provide a treated polyester fiber. It is an object of the present invention to provide a method for treating a polyester fiber capable of exhibiting adhesive performance as good as or better than conventional ones and mechanical properties such as strength and fatigue resistance. [Constitution] Polyester fiber is treated with a first treatment agent,
Next, resorcin / formalin / rubber latex (RF
In the treatment method of treating with a second treating agent containing L), the first treating agent has 1 hydroxyl group and 1 epoxy group in the molecule, respectively.
After reacting a compound containing more than one with a polyisocyanate compound having two or more isocyanate groups in the molecule,
A method for treating a polyester fiber, comprising a compound having a urethane bond, a hydroxyl group and a halogen group in the molecular structure, which is obtained by decomposing the remaining epoxy group by hydrogenolysis.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for treating polyester fiber, and the polyester fiber treated by the method of the present invention can be used for rubber composites such as tire cords, belts and hoses.

[0002]

2. Description of the Related Art Polyester fibers represented by polyethylene terephthalate fibers generally have physical properties such as excellent strength, Young's modulus, dimensional stability and fatigue resistance. It is widely used as a reinforcing fiber for rubber composites such as belts and hoses.

However, when compared with polyamide fibers such as nylon 6 and nylon 66, polyester fibers are
Adhesion to rubbers is poor even when treated with resorcinol / formalin / rubber latex (RFL), which is widely used for adhesion of rubber and fiber, and the excellent mechanical properties of polyester fiber are fully exhibited. I can't.

This is because the surface of the polyester fiber is inactive, the affinity and reactivity with RFL are poor, and the hydrogen bond ability of the ester bond in the polyester is smaller than the hydrogen bond ability of the amide bond of nylon. This is believed to be the main cause. Therefore, the surface of the polyester fiber is chemically and physically modified to introduce a functional group such as a hydroxyl group into the fiber surface to impart reactivity with RFL,
A method of imparting adhesiveness by treating with a highly reactive substance such as an epoxy compound or an isocyanate compound which has reactivity with polyester fiber and has affinity with polyester fiber has been put to practical use.

However, recently, there is a concern that epoxy compounds have an influence on health. Further, it has been pointed out that the isocyanate compound must be used in a solvent system, and needs to be blocked in order to use it in a water system, which is complicated.

[0006]

OBJECTS OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the present invention is to eliminate fear of toxicity such as epoxy compounds and isocyanates in adhesion between polyester fiber and rubbers, and It is an object of the present invention to provide a treatment method capable of maintaining the adhesive performance, strength, fatigue resistance, etc. that are equal to or higher than those of conventional ones.

[0007]

That is, according to the present invention, "(Claim 1) In a treatment method, a polyester fiber is treated with a first treatment agent and then with a second treatment agent containing resorcinol-formalin rubber latex (RFL), The first treating agent remains after reacting the compound (A) containing at least one hydroxyl group and at least one epoxy group in the molecule with the polyisocyanate compound (B) having two or more isocyanate groups in the molecule. A method for treating a polyester fiber, comprising a compound (C) having a urethane bond, a hydroxyl group and a halogen group in a molecular structure obtained by decomposing an epoxy group by hydrohalogenation. (A) is a linear or branched aliphatic hydrocarbon compound having 2 to 10 carbon atoms, and has at least one main chain or branched carbon atoms. The method for treating polyester fiber according to claim 1, which is a compound (A1) in which one hydroxyl group is bonded and at least one glycidyl ether group is bonded to one or more main chain or branched carbon. (Claim 3) The compound (A1) is glycerol polyglycidyl ether, trimethylolpropane polyglycidyl ether, sorbitol polyglycidyl ether,
1 selected from the group consisting of sorbitan polyglycidyl ether and pentaerythritol polyglycidyl ether
The method for treating polyester fiber according to claim 2, wherein the polyester fiber is one or more compounds. (Claim 4) The method for treating a polyester fiber according to claim 1, wherein the compound (A) is a polyglycidyl ether (A2) of polyglycerin having an unreacted hydroxyl group represented by the following general formula (Formula 2).

[0008]

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(Claim 5) The method for treating a polyester fiber according to claim 4, wherein the compound (A2) is polyglycerol polyglycidyl ether. (Claim 6) The method for treating a polyester fiber according to any one of claims 1 to 5, wherein the first treating agent contains a blocked polyisocyanate compound and a rubber latex. (Claim 7) The method for treating polyester fiber according to any one of claims 1 to 6, wherein the second treating agent contains a compound selected from the group consisting of a blocked polyisocyanate compound and ethylene urea. ".

The linear aromatic polyester in the present invention is represented by the general formula (Chemical Formula 3)

[0011]

Embedded image

A polyester having a repeating unit represented by the following as a main constituent.

In particular, polyesters containing at least one glycol selected from ethylene glycol and tetramethylene glycol as a main glycol component are preferably used. Typical polyester fibers are polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, and the like. The molecular weight, single yarn fineness, number of filaments, cross-sectional shape, fiber physical properties, fine structure, presence or absence of additives, polymer properties (concentration of terminal carboxyl groups, etc.) of the polyester fiber are not particularly limited.

Compound (C) having a urethane bond, a hydroxyl group and a halogen group in the molecular structure used for the first treating agent
Is a compound (A) containing at least one hydroxyl group and at least one epoxy group in the molecule, in an organic solvent using a suitable catalyst,
It can be obtained by reacting with a polyisocyanate compound (B) having two or more isocyanate groups in the molecule, and then subjecting the epoxy group to hydrogenolysis. Here, the epoxy content is preferably 0.1% or less, the hydrolyzable halogen content is 1% or more, and the total halogen content is 4% or more.

The compound (A) containing at least one hydroxyl group and at least one epoxy group in the molecule is a straight-chain or branched aliphatic hydrocarbon compound having 2 to 10 carbon atoms and has a main chain or a branched chain. A compound (A1) in which at least one hydroxyl group is bonded to carbon and at least one glycidyl ether group is bonded to carbon in the main chain or on a branch, and a compound represented by the following general formula (Formula 4) One or more compounds selected from polyglycidyl ethers of polyglycerin (A2) containing unreacted hydroxyl groups. Specifically, glycerol polyglycidyl ether, polyglycerol polyglycidyl ether, trimethylolpropane polyglycidyl ether, sorbitol polyglycidyl ether, sorbitan polyglycidyl ether,
Pentaerythritol polyglycidyl ether and the like.

[0016]

[Chemical 4]

The polyisocyanate compound (B) having two or more isocyanate groups in the molecule means hexamethylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, dicyclohexyl methane diisocyanate, o.
-Tolylene diisocyanate and the like.

As the reaction catalyst, an organic metal catalyst such as dibutyltin diacetate or dibutyltin dimaleate, an amine catalyst such as triethylamine or triethylenediamine, or the like can be used.

The compound (C) is preferably used as an emulsion. To prepare an emulsion or solution, a compound (C) as it is or dissolved in a small amount of solvent as necessary is added with a known emulsifier such as sodium alkylbenzene sulfonate, dioctyl sulfosuccinate sodium salt, nonylphenol ethylene oxide addition. It is emulsified or dissolved using a substance.

When the compound (C) is used as an aqueous dispersion, the amount of the dispersant, that is, the surfactant is 2 based on the solid content.
5% by weight or less, more preferably 15% by weight or less,
If it exceeds the above range, the adhesiveness tends to be slightly lowered.

The total solid content concentration of the first treating agent including the compound (C) is 0.1 to 30% by weight, and more preferably 0.3 to.
It is 20% by weight. If the concentration is too low, the adhesion performance will be insufficient, and conversely, if it is too high, the viscosity will be high and it will be difficult to control the adhesion amount.

When the compound (C) is mainly contained in the first treatment agent, the total solid content concentration is 0.1 to 15% by weight, more preferably 0.3 to 10% by weight. At this time, it is preferable to use, as the second treating agent, one containing a blocked polyisocyanate compound, ethylene urea or the like which will be described later.

When the first treating agent contains the compound (C), the blocked polyisocyanate compound (D) and the rubber latex (E), the total solid content concentration is 1 to 30% by weight, more preferably 3 to 20% by weight. %.

The blocked polyisocyanate compound used at this time is an addition compound of a polyisocyanate compound and a blocking agent, and the block component is liberated by heating to produce an active polyisocyanate compound. Examples of the polyisocyanate compound include tolylene diisocyanate, metaphenylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, polymethylene polyphenyl polyisocyanate, triphenylmethane triisocyanate, and the like, or these polyisocyanates and two active hydrogen atoms. Compounds having the above, such as trimethylolpropane and pentaerythritol, are combined with an isocyanate group (-NCO) and a hydroxyl group (-
Examples thereof include a polyalkylene glycol adduct polyisocyanate containing a terminal isocyanate group obtained by reacting at a molar ratio of OH) exceeding 1. In particular, aromatic polyisocyanates such as tolylene diisocyanate, diphenylmethane diisocyanate and polymethylene polyphenyl isocyanate are preferable because they exhibit excellent performance.

Examples of the blocking agent include phenols such as phenol, thiophenol, cresol and resorcinol, aromatic secondary amines such as diphenylamine and xylidine, phthalamides, lactams such as caprolactam and valerolactam, and the like. An oxime such as acetoxime, methyl ethyl ketone oxime and cyclohexane oxime, and acidic sodium sulfite are used.

The rubber latex is, for example, natural rubber latex, styrene-butadiene copolymer latex,
Vinyl pyridine / styrene / butadiene terpolymer latex, nitrile rubber latex, chloroprene rubber latex and the like, which are used alone or in combination. Of these, vinyl pyridine / styrene / butadiene terpolymer latex is preferably used alone or in combination. When used in combination, excellent performance is exhibited when more than 1/2 of the total latex weight is used.

When the first treating agent contains the compound (C), the blocked polyisocyanate compound (D) and the rubber latex (E), the compounding weight ratio of the respective components (C), (D) and (E) is (C) / [(C) + (D)] is 0.05 to
0.9, (E) / [(C) + D)] is preferably 0.5 to 15 before use. Especially (C) /
(C) + (D)] is 0.1 to 0.5, (E) / [(C)
+ (D)] is preferably in the range of 1-10.

If (C) / [(C) + (D)] is out of the above range, the rate of rubber adhesion to polyester fibers tends to be poor, and the adhesiveness tends to deteriorate, and (E) /
If [(C) + (D)] is smaller than the above range, the treated polyester fiber may be hardened and fatigue resistance may be deteriorated. On the other hand, if it is larger than the above range, adhesiveness may be deteriorated.

The second treatment agent is resorcin / formalin /
Although the composition contains rubber latex, the resorcin / formalin / rubber latex used here is usually RFL.
And the molar ratio of resorcin and formaldehyde is 1: 0.1 to 1: 8, more preferably 1: 0.5 to 1: 5, and particularly preferably 1: 1 to 1: 4. Used in the range.

The rubber latex is, for example, natural rubber latex, styrene-butadiene copolymer latex,
Vinyl pyridine / styrene / butadiene terpolymer latex, nitrile rubber latex, chloroprene rubber latex and the like, which are used alone or in combination. Of these, vinyl pyridine / styrene / butadiene terpolymer latex is preferably used alone or in combination. When used in combination, excellent performance is exhibited when more than 1/2 of the total latex weight is used.

The mixing ratio of resorcin / formalin and rubber latex depends on the adding ratio of the additive (F) described later, but the solid content ratio is 1: 1 to 1:15, more preferably 1: 3 to 1 The range of 12 is desirable. If the ratio of the rubber latex is too low, the treated polyester fiber material becomes hard and the fatigue resistance becomes poor. On the other hand, if the amount is too large, satisfactory adhesive strength and rubber adhesion cannot be obtained.

Additives such as blocked polyisocyanate and ethylene urea may be added to the second treating agent RFL. Blocked polyisocyanates are aliphatic, alicyclic or aromatic polyisocyanates and oximes, phenols,
It is obtained by reacting with caprolactam or the like, but a water-soluble blocked isocyanate represented by the following general formula (Formula 5) is preferable.

[0033]

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(In the formula, A is polyaromatic polyisocyanate (PAPI), X is a blocking agent residue, Y is a hydrophilizing agent residue, and B is a diol component.) Ethylene urea is disclosed in JP-B-57-21587. The general formula described in (Chemical Formula 6)

[0035]

[Chemical 6]

An ethylene urea compound represented by the formula (wherein R'is an aromatic or aliphatic hydrocarbon residue and n is 0, 1 or 2) is preferred. These additives are usually used in an aqueous dispersion using an emulsifier.

The blocked polyisocyanate and ethylene urea compound can be added alone or in combination. The addition rate is 0.5 to 30% by weight based on the RFL,
More preferably, it is 1.0 to 20% by weight. If the amount added is too small, good adhesion and rubber adhesion cannot be obtained. On the other hand, if the amount added is too large, the viscosity of the treating agent remarkably increases, and the treatment operation of the fiber material becomes difficult. In addition, the adhesive strength and the rubber adhesion rate have reached the saturation value and the effect of increasing the addition amount does not increase, the cost only rises, the fiber material after treatment becomes significantly hard and the strength decreases. The drawback is that it will come. The second treating agent is usually adjusted to contain 10 to 25% by weight of total solids.

To attach the first treating agent and the second treating agent to the polyester fiber material, application by a roller,
Any method such as spraying from a nozzle or dipping can be adopted. The amount of solids deposited on the polyester fiber is 0.1 to 10% by weight as the first treating agent composition, more preferably 0.5 to 5% by weight, and 0.5 to 10% by weight as the second treating agent composition. It is more preferable that the amount is 1 to 5% by weight. In order to control the amount of solid content adhered to the fibers, squeezing with a pressure contact roller, scraping with a scraper, etc., blowing with air blowing,
Means such as suction and beating with a beater may be used.

After treating the polyester fiber with the first treating agent, it is dried at 50 to 180 ° C. for 0.5 to 5 minutes, more preferably 1 to 3 minutes, and then at 180 ° C. to 10 ° C. lower than the melting point of the polyester fiber. , And more preferably 220-
After heat treatment at a temperature of 250 ° C. for 0.5 to 5.0 minutes, more preferably 1 to 3 minutes, and further after treatment with a treatment agent containing RFL of the second treatment agent, 0.5 to 5.0 at 80 to 180 ° C. 5 minutes,
More preferably, it is dried for 1 to 3 minutes, and then 150 to 26
0.5 at a temperature of 0 ° C., more preferably 220 to 250 ° C.
Heat treatment is performed for ˜5.0 minutes, more preferably for 1 to 3 minutes. If the heat treatment temperature is too low, the adhesion with rubbers becomes insufficient, while if the temperature is too high, the polyester fibers are melted and fused, become extremely hard, or strongly deteriorate, and cannot be put to practical use.

[0040]

The compound (C) contained in the first treating agent of the present invention has a halogen group such as a chlorine group or a bromine group having an affinity for the polyester fiber, and the hydroxyl group in the treating agent and the blocked isocyanate. It is presumed that and react with each other to enhance the cohesive force of the adhesive, and at the same time, the urethane bond and the hydroxyl group exhibit the affinity with RFL to develop the adhesiveness. Further, the polyester fiber treated by the method of the present invention has the adhesive performance equivalent to that of the conventional method.

The present invention will be specifically described below with reference to examples. In the examples, the cord peeling adhesive force, the pulling adhesive force, and the ply peeling force are values obtained as follows. <Cord peeling adhesive strength> It shows the adhesive strength between the treated cord and rubber. Un-vulcanized rubber sheet with natural rubber as the main ingredient
Vulcanize at 0 ° C. for 30 minutes at a pressing pressure of 50 kg / cm ² (initial value) or at 180 ° C. for 60 minutes at a pressing pressure of 50 kg / cm ² (heat resistant value), then leave 5 cords at both ends. 2 in the direction of 90 degrees to the rubber sheet surface
00 mm / min. The force required for peeling at the speed of k
It is shown in g / 5. <Cord pull-out adhesive strength> This shows the shear adhesive strength between the treated cord and rubber. Embed the cord in an unvulcanized rubber block containing carcass containing natural rubber as a main component,
Vulcanize at 30 ° C for 30 minutes (initial value) or 180 ° C for 60 minutes (heat resistance value), then 200m from the rubber block.
m / min. And the force required for pulling out is displayed in kg / cm. <Peeling force between plies> This shows the adhesive force between the treated cord and rubber. The treated cords are arranged at a cord density of 27 cords / inch, sandwiched between two 0.4 mm unvulcanized rubbers, and the two molded sheets obtained are cross-plied so as to form an angle of 90 degrees, and natural rubber is the main component. Embedded in unvulcanized rubber with carcass blended at 150 ° C for 30 minutes, 50 kg / cm
² press pressure (initial value) or 180 ℃, 60 minutes, 5
After vulcanizing at a pressing pressure (heat resistant value) of 0 kg / cm ² ,
Both plies are 200 mm / min. The force required for peeling at the pulling speed of is expressed in kg / inch. <Rubber Adhesion Rate> It is a scale showing the adhesiveness of rubber to fibers. The cord peeled from the rubber during the above-described measurement of the peeling force between the plies was observed with the naked eye, and the portion of the cord surface on which the rubber was attached was visually expressed and expressed as a percentage.

[0042]

Examples 1 to 7, Comparative Example 1 Compound (C1) (Synthetic Formula 1) having the urethane bond and the chlorine group in the molecular structure represented by the following general formula (Chemical Formula 7) is hexamethylene. Made by Kogyo Co., Ltd., prototype, concentration 63.8%) 1
To 0 g, 5 g of Neocor SW-30 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., 30% aqueous solution of dioctylsulfosuccinate sodium) as a surfactant was added and uniformly dissolved.
To this, 985 g of water was added with stirring and uniformly dissolved. The resulting blended liquid is used as the first treatment agent.

[0043]

[Chemical 7]

Also, 4.4 g of a 10% aqueous sodium hydroxide solution,
28% aqueous ammonia solution (12.8 g) was added to water (314.6 g), and the resulting solution was stirred well to give an aqueous solution of resorcinol / formalin initial condensate Adhar RF (Hodogaya Chemical Co., Ltd., 43% acetone). solution)
26.7 g was added and sufficiently stirred to disperse. Next, 263 g of Nipol 2518FS (Nippon Zeon Co., Ltd., vinylpyridine / styrene / butadiene terpolymer water emulsion) and Nipol LX-112 (Nihon Zeon Co., Ltd., styrene / butadiene copolymer 41%)
112.8 g of water emulsion) was diluted with 343.7 g of water.
The above-mentioned resorcinol / formalin initial condensation dispersion was slowly added to this diluted solution, and 11.1 g of formalin (37% aqueous solution) was further added and mixed uniformly, and then elastron was added to this mixed solution. 90.9 g of BN-04 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., water-soluble blocked polyisocyanate 33% aqueous solution) was added and mixed, and the resulting blended solution was used as a second treatment agent (20% concentration).

Polyethylene terephthalate having a [η] of 0.89 was melt-spun and stretched by a conventional method to obtain a multifilament of 1500 denier / 192 filaments, and then the two multifilaments were 40 × 40T.
A cord of 3000 denier / 384 filament was obtained by twisting at / 10 cm.

These codes are stored in the computer
Riki (CA Ritzler Co., Ltd., tire cord processing machine)
At 130 ° C. after immersion in the first treatment agent using
It was dried for 2 minutes and then heat-treated at 230 ° C. for 1 minute.
Then, after soaking in the second treatment agent, dry at 170 ° C for 2 minutes.
It is dried and then heat-treated at 230 ° C. for 1 minute. The treated poly
The solid content of the first treating agent is 2.2 in the stell tire cord.
%, The solid content of the second processing agent is 2.0% by weight.
It was The treated cord thus obtained is composed mainly of natural rubber
Embed in unvulcanized rubber containing carcass and press pressure
Force 50kg / cm ²At 150 ℃ for 30 minutes (first time
(Periodic value) and 180 ° C. for 60 minutes (heat resistance value).

The compounding conditions of the first treating agent were variously changed as shown in Tables 1 and 2 and repeated. The experimental results are shown in Tables 1 and 2. As a comparative example, Denacol EX-314 (manufactured by Nagase Kasei Kogyo Co., Ltd., glycerin diglycidyl ether) (Comparative Example 1) was used instead of the compound (C1), and the same procedure as in Example 1 was carried out. Was prepared and the adhesiveness was evaluated. The results are also shown in Tables 1 and 2. As is clear from Tables 1 and 2, the adhesion level of the present invention showed a value equivalent to or higher than that of the epoxy compound.

[0048]

Examples 8 to 11, Comparative Examples 2 to 5 Compound (C1) of Synthesis Example 1 (manufactured by Nagase Kasei Co., Ltd., prototype, concentration 6)
3.8%) 4.6 g of Neocor S as a surfactant
2.5 g of W-30 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., 30% aqueous solution of sodium dioctylsulfosuccinate) was added and uniformly dissolved. This was added to 734 g of water with stirring to uniformly dissolve each agent in water. Then S-3
(Meisei Chemical Industry Co., Ltd., ε-caprolactam blocked isocyanate 25% by weight water emulsion) was added and further stirred, and Nipol 2518FS (Nippon Zeon Co., Ltd., vinylpyridine / styrene / butadiene terpolymer 41% by weight). % Water emulsion) 212.5 g was added and mixed uniformly. The obtained mixture was used as a first treating agent.

The same second treating agent as in Example 1 was used, and polyethylene terephthalate fiber was treated and vulcanized in the same manner as in Example 1. The above experiment was repeated by changing the compounding conditions of the first treatment agent as shown in Table 3. The experimental results are shown in Tables 3 and 4.

As comparative examples, one obtained by removing the blocked polyisocyanate in the first bath agent from the example (Comparative Example 2), one excluding the rubber latex (Comparative Example 3), the blocked polyisocyanate and the rubber latex were used. The removal was performed (Comparative Example 4), and the one using Denacol EX-611 (sorbate polyglycidyl ether manufactured by Nagase Kasei Co., Ltd.) instead of the compound (C1) (Comparative Example 5) was performed. Others were the same as in the example. The results are also shown in Tables 3 and 4. As is clear from Tables 3 and 4, the compound (C), the blocked polyisocyanate (D) and the rubber latex (E) coexist in the first bath, and the second bath contains It was found that the adhesive property was the best when the blocked polyisocyanate (F) was added. Moreover, this adhesion level showed the same level as the conventional level.

[0051]

Examples 12 to 19 In Example 8, the compound (C
The compounding ratios of 1), blocked polyisocyanate (D) and rubber latex (E) were changed as shown in Table 5, and other conditions were the same as in Example 8. The results are shown in Tables 5 and 6. As is clear from the results shown in Tables 5 and 6, (C) / [(C) + (D)] is 0.05 to 0.9,
It was found that a higher level of adhesiveness can be obtained by blending (E) / [(C) + (D)] so as to be 0.5 to 15.

[0052]

[Table 1]

[0053]

[Table 2]

[0054]

[Table 3]

[0055]

[Table 4]

[0056]

[Table 5]

[0057]

[Table 6]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Reference number within the agency FI Technical display location D06M 13/432 15/693 // D06M 101: 32 (72) Inventor Mitsukuni Mohri Tatsuno City, Hyogo Prefecture 236, Nakai, Tatsuno-cho Nagase Kasei Kogyo Co., Ltd. (72) Inventor Satoru Fujii 236 Nakai, Tatsuno-cho Tatsuno-shi, Hyogo Prefecture Nagase Kasei Kogyo Co., Ltd. (72) Hiroyuki Iwasaki 236 Nakai, Tatsuno-cho, Tatsuno-shi, Hyogo Nagase Kasei Industry Co., Ltd.

Claims (7)

[Claims] 1. A method of treating a polyester fiber with a first treating agent and then with a second treating agent containing resorcinol-formalin rubber latex (RFL), wherein the first treating agent has a hydroxyl group in the molecule. And a compound (A) containing one or more epoxy groups each, and a polyisocyanate compound (B) having two or more isocyanate groups in the molecule are reacted with each other, and then the remaining epoxy groups are hydrohalogenolytically decomposed. A method for treating a polyester fiber, which comprises the compound (C) having a urethane bond, a hydroxyl group and a halogen group in its molecular structure, obtained by 2. The compound (A) is a linear or branched aliphatic hydrocarbon compound having 2 to 10 carbon atoms, in which at least one hydroxyl group is bonded to one or more main chains or branched carbons. And a compound (A1) in which at least one glycidyl ether group is bonded to one or more main chain or branched carbon atoms. 3. The compound (A1) is glycerol polyglycidyl ether, trimethylolpropane polyglycidyl ether, sorbitol polyglycidyl ether,
1 selected from the group consisting of sorbitan polyglycidyl ether and pentaerythritol polyglycidyl ether
The method for treating polyester fiber according to claim 2, wherein the polyester fiber is one or more compounds. 4. The method for treating a polyester fiber according to claim 1, wherein the compound (A) is a polyglycidyl ether (A2) of polyglycerin having an unreacted hydroxyl group represented by the following general formula (Formula 1). Embedded image 5. The method for treating a polyester fiber according to claim 4, wherein the compound (A2) is polyglycerol polyglycidyl ether. 6. The method for treating a polyester fiber according to claim 1, wherein the first treating agent contains a blocked polyisocyanate compound and a rubber latex. 7. The method for treating polyester fiber according to claim 1, wherein the second treating agent contains a compound selected from the group consisting of a blocked polyisocyanate compound and ethylene urea.