JPS59204921A - Production of synthetic fiber having water and oil repellency and antistaining property - Google Patents

Abstract

PURPOSE:To obtain synthetic fibers having improved water and oil repellency and antistaining property, by melt spinning a synthetic polymer, applying a spinning oiling agent containing no water to the resultant undrawn synthetic filament yarn, applying a specific treating agent thereto, and drawing and heat- treating the filament yarn. CONSTITUTION:A synthetic polymer, e.g. polyamide, is melt spun and extruded through a spinneret 1 and cooled in a cooling zone 2 to give an undrawn filament yarn 3. A spinning oiling agent containing no water with <=5% moisture is then applied to the undrawn filament yarn 3 in an oil application device 4, and then a composition consisting essentially of a compound expressed by the formula [Rf is perfluoroalkyl group; X is bifunctional alkyl, -CON(R')-Q-, etc.; (R' is H or lower alkyl group, etc.; Q is bifunctional organic group); A and A' are oxygen, etc.; W is tri- or polyfunctional organic group; a+b is >=3] in an amount of 0.03-2.00wt% based on the above-mentioned filament yarn 3 is applied thereto. The resultant filament yarn is then drawn and heat-treated to afford the aimed fibers.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing synthetic fibers having water-repellent, oil-repellent and antifouling properties.

Conventionally, in the field of textile products such as carpets, water-repellent, oil-repellent, and stain-repellent treatments have been widely used, and treatment agents such as perfluoroalkyl group-containing polyacrylates, various perfluoroalkyl group-containing urethane compounds, or JP-A-5
Water-repellent, oil-repellent and antifouling agent compositions (hereinafter simply referred to as treatment agents) described in JP-A No. 4-74000, JP-A-56-13L687, and JP-A-57-59285 are used. ing. As a method of applying the treatment to the carpet, a so-called post-treatment method is generally used in which the treatment agent is applied to the surface by spraying or dipping during or after carpet treatment.

However, in the case of the method of applying the treatment agent by spraying, it is not possible to uniformly apply the treatment agent to the fibers.
In the case of dipping, the treatment agent has the disadvantage that it adheres to substantially unnecessary parts such as the base fabric of the carpet or one part of the pile, which detracts from the texture of the entire carpet. Further, in the case of the above-mentioned post-processing method, there is a problem in that a large treatment agent application device having a size corresponding to the width of the carpet must be installed in the ordinary carpet manufacturing equipment.

In particular, when applying a treatment agent to cut-pile style carpets such as sakinny, plano/yue, or velor, the treatment agent sticks to the intertwined portions of the fibers, reducing the mutual degree of freedom. However, there is a problem that the texture becomes extremely rough and hard. Furthermore, since these processing agents have weak adhesion to air fibers, there is a problem in that their performance tends to deteriorate due to long-term use or washing.

As a means to improve the above-mentioned problem, a method is proposed in which a processing agent is mixed into the spinning oil that is added during the spinning of synthetic fibers to provide e-1 (as is known from Japanese Patent Laid-Open No. 55-90677). Although this method increases the advantage in terms of process control, it is easy to separate the spinning oil and treatment agent, and there are many restrictions on the management of the characteristics, mixing ratio, and changes over time of the spinning oil and treatment agent. However, there is a problem in that it cannot be put to practical use in mass production methods.

Furthermore, with regard to treatment agents, none of the conventionally known treatment agents can satisfy the temporal changes in water repellency, oil repellency, and antifouling performance, that is, the retention thereof, and only temporary effects can be expected.

The purpose of the present invention is to eliminate the drawbacks of conventional water-repellent, oil-repellent, and stain-resistant synthetic fibers, to more effectively improve water-repellent, oil-repellent, and stain-proof properties, and to provide extremely advantageous methods for manufacturing process control. Water repellent, oil repellent,
The object of the present invention is to obtain a synthetic fiber having antifouling properties.

As a result of intensive studies to achieve the above objective, the present inventors adopted a specific process of applying a non-hydrous spinning oil to synthetic fibers and then applying a treatment agent in addition to using a specific treatment agent. It was discovered that by doing so, synthetic fibers having excellent water repellency, oil repellency, and stain resistance can be obtained extremely efficiently, and the present invention was achieved.

That is, in the present invention, a synthetic polymer is melt-spun to form an undrawn yarn, a non-water-containing spinning oil with a water content of 5% or less is applied to the undrawn yarn, and it is kilned to obtain the general formula [xf-x-A -c
oNu), w-ENHco-A' -z)5 [However,
In the formula, Rf is a perfluoroalkyl group, and X is -R-1-
CONC Bi) -Q- or -8o2N(R') -Q
- (where R is a divalent alkyl group, R' is hydrogen or a lower alkyl group, and Q is a divalent organic group), A and A' are further -1-8- or -N (Z' - Here, Z' represents hydrogen or a monovalent organic group, Z is 1
a valent organic group, W is a trivalent or higher organic group, a and b are a+
Indicates an integer satisfying b≧3. ] A treatment agent containing a compound represented by the following as a main component is applied to the yarn in an amount of 0.03 to 2.
A method for producing synthetic fibers having water-repellent, oil-repellent, and antifouling properties, which comprises adding 0.00% by weight, and then subjecting the yarn to a drawing heat treatment, and a method for producing synthetic fibers having water-repellent, oil-repellent, and antifouling properties, and a fluid jet method in which the above-described drawn yarn subjected to the drawing heat treatment is mixed with a hot fluid. The present invention provides a method for producing synthetic fibers having water-repellent, oil-repellent, and stain-repellent properties, which is characterized by forming a continuous bulky yarn through a nozzle.

Hereinafter, a more detailed explanation will be given with reference to specific drawings. Note that the drawings are process diagrams showing preferred embodiments of the present invention.

As shown in Figure 1, melt the synthetic polymer and
The synthetic fibers spun from the cooling zone 2 are cooled. Synthetic polymers here refer to those that can be melt-spun, such as polyamides, polyesters, polyurethanes, polyolefins, etc., but since the main application of the present invention is in the carpet field, the synthetic polymers have excellent coloring properties, durability, and resistance to bedding.
Polyamide, which has excellent wear resistance and recovery properties, is most preferably used.

There are polyamides with different dyeing abilities, and any one can be used as required. Melt-spun undrawn spun yarn (undrawn yarn) can be obtained in various cross-sectional shapes, but in the case of carpet applications, it is necessary to improve crimpability, texture, water repellency, oil repellency, and antifouling agents. Due to its adhesion to fibers, Y-shaped
It is preferable to use threads with irregular cross-sections, such as a Japanese character shape.

A spinning oil is applied to the cooled undrawn yarn 3 by an oil applying device 4. The amount of the oil applied is 0 to the undrawn yarn.
．． It is within the range of 3 to 3% by weight.

The spinning oil agent contains a smoothing agent, an emulsifier, an antistatic agent, etc. and is normally used in the spinning process of synthetic fibers.
It is necessary that this is a substantially water-free oil agent with a water content of 05% or less.

After the spinning oil is applied,
When applying a treatment agent (=1) for imparting oil repellency and stain resistance, the surface of the synthetic fiber is covered with a non-water-containing oil agent, and the treatment agent is applied to the outer periphery of the non-water-containing oil agent. This is to prevent loss of stretchability.In other words, when the spinning oil is a water-containing oil, the treatment agent applied later diffuses into the water-containing oil and comes into direct contact with the formed fibers, causing the fiber surface to drop. The oil film becomes partially uneven,
Yarn breakage occurs frequently during stretching, which significantly deteriorates yarn spinning properties. In addition, processing agents are mixed into the spinning oil to create synthetic fibers (
When this is applied, similar symptoms are observed and the silk-spinning properties are deteriorated, which is not preferable.

Therefore, after the surface of the undrawn yarn 3 spun as described above is sufficiently and uniformly coated with a non-hydrous spinning oil, a treatment agent (preferably in the form of an aqueous dispersion) is applied using a treatment device 5. Therefore, the treatment agent is more uniformly dispersed on the surface of the spinning oil coating.

The device 5 for applying the treatment agent described in 01j may be provided between the take-up roller 6 of the undrawn yarn 3 and the drawing roller ruff 8.9, and in some cases, the drawing roller 8 or 9 may be connected to the heating roller t. When this is the case, it can also be provided at the point directly n1 of the addition p, r: 80-ra.

In other words, the drawn yarn may be heat-treated after the treatment agent has been applied, and in the present invention, including such application method, the l' treatment agent compound can be used in the engraving of the specification (without any change to the round table). The spun yarn is drawn and heat treated to make it C+.

The processing agent used in the present invention is a composition containing a compound having the general formula % as a main component, where Rf is a perfluoroalkyl group, and particularly has 6 to 12 carbon atoms.
Preferably. X is -R-1-CON (R')
-Q- or -3O2N(R')-Q-, where R
is a divalent alkyl group, R1 is hydrogen or a lower alkyl group, and Q is a divalent organic group. A and A in Matko style
' is -0-1-5-Matoko is -N (Z')-,
Z' here is hydrogen or a monovalent organic group. Z
is a monovalent organic group, and a specific example of -A'-Z is -NHCH20H1-NHC2H, OI(.

-0C2H,NO,, -0CzH40H, -N(C,L
-L, 0H) 2, light? Engraving of lll'F'f (no change in content) -OR, -5R, and -NCR#)2-N
HCR"+ (where R' is an alkyl group), etc. Also, each of Rf-X-A- or -Z-A'- may be of a plurality of types. As a compound into which W is introduced, Various polyvalent isocyanates can be generally applied to 1. Further, a and b are a + and b≧3.
The ratio of a to 1] may be obtained by IFI as the average value of ω of a large number of group companies.

In other words, the compound represented by the general formula L may be a mixture of multiple compounds, or a mixture with other perfluoroalkyl group-containing compounds or non-fluorinated polymers depending on the purpose. It may be.

Specific examples of compounds represented by the following general formulas include the following.

(Rf in the formula represents a perfluoroalkyl group having 6 to 14 carbon atoms.) As the processing agent application device 5, a known device is used. Further, the processing agent is adjusted to have a solid content concentration of 3 to 15%.

The amount of the treatment agent applied is such that the solid content of the water-repellent, oil-repellent, and stain-proofing composition containing the above-mentioned compound as a main component is 0.03 to 2% by weight, preferably 0.05 to 1% by weight, based on the synthetic fiber. , U% by weight.

In addition, in order to apply the treatment agent uniformly and effectively obtain water-repellent, oil-repellent, and stain-repellent properties with as little amount as possible, it is necessary to apply the treatment agent to each single yarn of the synthetic fibers by pulling them in rows t apart. This is why the treatment agent is applied at the aforementioned location.

The synthetic fibers to which the T-treatment agent has been applied as described above may be subjected to a drawing process after passing through the tearing roller 6 and forming a winding bobbin, but preferably as shown in the drawings. This is immediately followed by stretching rollers7.
It is stretched from 8.9t. More preferably, if the stretching roller 7 is used as a fixed stretching bin, crimp processing using a heated fluid, which will be described later, will be facilitated. The temperature of the heat treatment roller 8.9 is 100 to 250°C, preferably 160°C.
~200°C.

The drawn yarn is then wound 10 to 20 times around a heat treatment roller 8.9, thereby fixing the treatment agent onto 5 tons of synthetic fibers and heat fixing them. Then, by winding the thread into a bobbin (not shown in FIG. 1), it is preferably water-repellent.
Synthetic fibers with oil extraction stain resistance can be obtained.

In particular, when it is desired to obtain a crimped bulky yarn suitable for use in carpets, it is advisable to carry out the next process following the above-mentioned drawn and heat-treated yarn.

That is, by passing the drawn and heat-treated yarn through the jet nozzle 10 with a heating fluid of 150 to 350°C,
Furthermore, as heat setting progresses, continuous three-dimensional random crimping is efficiently imparted to the synthetic fiber. Superheated steam or air is suitable as the thermal fluid used here. The last t bulky yarns are wound up by the winding device 11. - As described above, the method of the present invention is characterized in that a water-repellent, oil-repellent, and antifouling treatment agent is applied after applying a water-free spinning oil to the synthetic fiber.

As a result, the effect of the treatment agent on the spinnability of synthetic fibers (
It is possible to prevent adverse effects such as single yarn breakage due to adhesion spots, and to avoid constraints such as compatibility and stability, which are problems when applying spinning oil and processing agents in a mixed system, as has been known in the past. It becomes possible to apply a treatment agent to a very wide tumor circumference without causing any damage.

The bulky yarn of the water-repellent, oil-repellent and stain-resistant synthetic fiber obtained in this way has four properties other than water-repellent, oil-repellent and stain-resistant properties: strength, elongation, boiling water shrinkage rate, and crimp elongation rate. , moisture content, dyeability,
There is almost no difference in light resistance and changes in these properties over time compared to untreated synthetic fibers.

Therefore, a major feature of the present invention is that a highly processed product can be rubbed in exactly the same manner as general synthetic fibers that are not treated with the treatment agent of the present invention during the high-level processing step.

That is, in the present invention and in general carpet processing, synthetic fibers are twisted with a twisting machine and steam-set depending on the purpose.

Next, the carpet is shaped and strained using a tufting machine or other carpet processing methods, and then dyed by batch dyeing or continuous dyeing to be finished into carpet products. In another process, after being twisted, it is dyed using methods such as cheese dyeing, hem dyeing, etc., and then shaped into a carpet using a tufting machine or other carpet processing methods. When using the water-repellent, oil-repellent, anti-fouling synthetic fiber continuous bulky yarn obtained by implementing the present invention,
Not only does it eliminate the need for spraying, dipping, and other application equipment for treatment agents, which were conventionally required as post-processing, but almost the same processing conditions as when using ordinary untreated synthetic fibers can be applied. A further advantage of the present invention is that the surfactant in the treatment agent that has an adverse effect on the water and oil repellency of carpet products is washed away during the dyeing process, and the subsequent drying process usually takes 5 to 30 minutes at 100 to 150C to dry algae. By doing so, the perfluoroalkyl groups are sufficiently oriented, resulting in extremely excellent water repellency, oil repellency, and stain resistance.

Details J: Nojo,? ! 'i (, j') No change in I content) Also, the deterioration of water repellency, oil resistance, and llj resistance due to long-term use or washing of Carpella I- obtained by implementing the present invention is due to conventional post-processing. It is quite small compared to that by law.

The synthetic fibers obtained by the method of the present invention can be applied to interior AA materials such as curtains, wall materials, and sheets, and fabrics such as bags, shoes, work clothes, and aprons, in addition to the above-mentioned carbella field.

Next, the present invention will be specifically explained with reference to Examples.

Example 1 Polyamide Berets 1 to 1 were melted and spun using gold having seven holes to obtain an undrawn yarn with a Y-shaped cross section. A water-free spinning oil is applied to the yarn in an amount of 20% by weight based on the yarn, and then the yarn is coated with the formula (where R'f is a carbon number of 6 to 141).
Aqueous dispersion treatment agent (11) with a concentration of 7.5% obtained by dispersing a perfluoroalkyl group-containing urethane compound (A) whose main structural formula is Q is applied to the yarn under conditions such that a solid content adhesion amount is 4% by weight,
Subsequently, using a drawing bottle, the yarn was stretched 4.0 times by t to obtain a drawn thread, and the drawn thread was wound several times around a heated roller heated to 170°C for heat treatment.

Next, this drawn yarn was passed through a fluid jet nozzle T together with hot air at 240° C. to form a bulky yarn, and then wound with an 11 winding machine. The spinning properties were good, and no difference was observed compared to when the 3111 agent was not applied.

The thus obtained water-repellent, oil-repellent, stain-resistant polyamide continuous bulky yarn was a three-dimensional randomly crimped yarn of 1300 denier and 68 filaments, and the characteristics of this yarn are summarized in Table 1 in comparison with the untreated system.

Next (2 twists of 190 tan/m are applied to the above processing system,
Two of these yarns were twisted together and S-twisted at 160 strands/m, then placed in an autoclave for 130 minutes.
(No change in content) Heat setting was performed at ℃ for 30 minutes.

Furthermore, using a cutting machine, tuft gauge 5/
32, Stitch 8/inch, Pile height 11.5mm Saxony style carpet, 95℃, 60f) I! After carrying out conventional dyeing using an acidic dye, washing with water, dehydration, and drying for 110 minutes and 20 minutes yielded a water-repellent, oil-repellent, and stain-resistant carpella 1-. Table 2 shows the performance of the force J-Pet 1-.

Example 2 A polyamide pellet was melted and spun using [1 gold] having Kuniji holes to obtain an undrawn yarn with a cross section of a shape. After adding 2.0% by weight of a water-free spinning oil to the yarn, the yarn was given the formula (here, Rf is a perfluoroalkyl group having 6 to 14 carbon atoms) as the main structural formula. An aqueous dispersion treatment agent (II) with a concentration of 580% obtained by dispersing Bl in water using an emulsifier was added to the yarn at a concentration of 0.3%. Granted under conditions that result in type classification,
Subsequently, the drawn yarn was drawn 45 times using a drawing bottle to obtain a drawn yarn, and the drawn yarn was wound several times around a heated roller heated to 180°C for heat treatment.5The drawn yarn was then heated to 250°C. The yarn was passed through a jet nozzle with steam to form a bulky yarn, and then wound up with a winder. The spinning properties were good, and there was almost no difference between the results and when no treatment agent was applied.

The water-repellent, oil-repellent, stain-resistant polyamide continuous bulky yarn thus obtained is a three-dimensional, undum-wound cotton yarn of 1,300 denier and 80 filaments, and the characteristics of this yarn are summarized in Table 1 in comparison with the untreated system. .

Furthermore, three yarns of this treatment system were combined to give an S twist of 40 tan/m, and then a tuft gauge of 5/5 was applied using a tufting machine.
32. Level loop style carve light 1 with stitches 8/inch and pile height 8g! , ff: engraving of Vj'-
(Contents unchanged. Processed to λ-soto, then dyed normally with acid dye using a Wins dyeing machine at 95°C for 60 minutes, washed with water, dehydrated, and dried at 110°C for 20 minutes to achieve water resistance. An oil and stain resistant carpet was obtained. Table 2 shows the performance of the carpeters 1 to 1.

Example 3 The treatment agent used in the same method as in Example 2 was a perfluoroalkyl group-containing urethane compound (where Rf is a perfluoroalkyl group having 6 to 14 carbon atoms) having the main structural formula: Aqueous dispersion treatment agent with a concentration of 5% obtained by dispersing q in water using an emulsifier (changed to ml). The quality of the yarn and the performance of the carpet were the same as in Example 2 (no change in content).

Example 4 The treatment agent used in the same method as Example 2 was a perfluoroalkyl thread-containing urethane compound having the structural formula (where Rf is a perfluoroalkyl having 6 to 14 carbon atoms, and R is the main component). An aqueous dispersion treatment agent with a concentration of 5% obtained by dispersing it in water using an emulsifier (changed to Ivl and obtained in the same manner except for The yarn quality and carpet performance were as low as in Example 2.

Comparative Example 1 The compound (5) in Example 1 and the water-free oil agent in Example 1 were mixed and applied to the undrawn yarn while stirring, and all other conditions were the same as in Example 1 to achieve water repellency, oil repellency, A stain-resistant polyamide fiber and a carpet made of the fiber were obtained.

Each characteristic and yarn-spinning property were as shown in Tables 1 and 2.

(Compound (A) and the non-water-containing oil separate when stirring is stopped, and the adhesion to the undrawn yarn becomes extremely uneven and the resulting yarn cannot be drawn. Comparative Example 2 Compound (B) in Example 2 and Example 2 A non-water-containing oil agent was mixed and applied to the undrawn yarn while stirring, and all other conditions were the same as in Example 2.A water-repellent, oil-repellent, stain-resistant polyamide fiber and a carpet made of the fiber were obtained. The properties and spinning properties were as shown in Tables 1 and 2e.

(If stirring of compound (B) and non-hydrous oil agent is discontinued,
Comparative Example 3 (Undrawn polyamide yarn obtained in the same manner as Example 2)
After applying this spinning oil with a water content of 45%,
．． Then, the treatment agent (Ill) described in Example 2 was applied to the undrawn polyamide yarn so that the solid content amount was 0.3% by weight, and all other conditions were the same as in Example 2.
The result of obtaining oil-repellent fibers was that, compared to when only a water-containing oil agent was simply applied, the spinning properties in the drawing process were significantly impaired, and single fiber breakage occurred frequently. In addition, when the obtained polyamide drawn yarn was crimped under the same conditions as in Example 2, the water repellency, oil repellency, and stain resistance were improved, but the strength required for synthetic fibers was significantly lowered for practical use. It was not possible to offer it to

Comparative Example 4 Polyamide fibers and a carpet made of the fibers were obtained under the same conditions as in Example 1 except that the treatment agent ([) in Example 1 was not applied. The results were as shown in Table 1.2.

Comparative Example 5 A carpet consisting of polyamide G i,il: and the fibers thereof was obtained under the same conditions as in Example 2 except that the treatment agent in Example 2 was not applied. The results were as shown in Table 1.2f.

Comparative Example 6 A carpet obtained under the same conditions as Comparative Example 4 was sprayed with the treatment agent (I) used in Example 1 to give a solid content of 0.4% by weight to the fibers. did. The quality of the obtained carpet was as shown in Table 2.

Comparative Example 7 Using a carpet spray obtained under the same conditions as Comparative Example 5, the treatment agent (Il) used in Example 2 was applied to the fibers at a rate of 0.
It was applied so that the solid content amount was 3% by weight. The quality of the obtained carpet was as shown in Table 2.

Comparison/Example Using polyester pellets as the synthetic crystal fiber material, Example 1.
2. Among the conditions of Comparative Examples 1 to 7, spinning temperature, stretching ratio,
Various fibers and carpets were obtained according to the conditions of Example 1.2 and Comparative Examples 1 to 3.5.6, except that the heating temperature was set to be suitable for polyester fibers. The results showed that although the water and oil repellency was slightly inferior to that obtained when polyamide was used, it was sufficiently usable for practical use, and its effects were sufficiently recognized.

The measurements of water repellency, oil repellency and stain resistance described in the above Examples and Comparative Examples were carried out as follows.

That is, water repellency is expressed as the number of seconds it takes for the liquid to soak into the carpet when approximately n04 cc of a 20% by volume aqueous solution of Impropanol is dropped onto the carpet from a height of 1 cIR. Note that measurements were performed at 50 or more locations to determine uniformity.

Oil repellency is determined by dropping approximately 0.05 CC of the test solution shown in Table 5 on the carpet from a height of 1α, and determining the penetration state after 30 seconds (AATCC-118-197J).The measurement is to determine uniformity. In order to do this, we visited more than 50 locations.

A stain-resistant i-carpet is placed on a carpet that is frequently walked on, and when a total of 40,000 pedestrians walk on the carpet, the staining condition is determined with the naked eye and the reflectance before and after use is measured to determine the contamination rate. The contamination rate is calculated as follows.

RB RB Reflectance of uncontaminated carpet RS = Reflectance of carpet after walking pollution Stain resistance 20 Dirt is hardly noticeable (judgment with naked eye) △ Stains are noticeable × Extremely (Table 6) As is clear from the second result, according to the method of the present invention, there is no deterioration in yarn reeling properties or deterioration in texture caused by applying a water-repellent, oil-repellent, or anti-fouling agent to synthetic fibers, and the treatment agent is not applied to the synthetic fibers. It has become industrially possible to obtain synthetic fibers that maintain almost the same spinnability and texture as those without the addition, and also have water-repellent, oil-repellent, and stain-repellent properties, especially carpets that have these properties. This has the advantage that the treatment agent can be applied very easily.

[Brief explanation of the drawing]

FIG. 1 is a process diagram showing a preferred embodiment of the present invention. 1... Spinneret 2... Cooling zone 3... Synthetic fiber 4... Spinning oil application device 5... Treatment agent application device 6... Take-off roller 7... Stretching pin or roller 8.9 ...Thermal roller 10...Thermal fluid jet nozzle 11... Winding device Patent applicant Toshi Co., Ltd. Asahi Glass Co., Ltd. Figure 1 1111 Procedure amendment (one-sided)
Showa Oro Monthly 8/9/14 Commissioner of the Japan Patent Office Kazuo Wakasugi 1 Display of the case 1984 TE Patent Application No. 76277 2 Name of the invention Method for producing synthetic fibers with water-resistant, oil-resistant, and stain-resistant properties 3 Address related to the case of the person making the amendment: 2-2 Nittahashi Muromachi, Chuo-ku, Tokyo August 30, 1982 (shipment date) Specification contents: 10, 11, 12, 17, 19,
Edit pages 21 and 22 as shown in the attached sheet.

Claims (1)

[Scope of Claims] 1. A synthetic polymer is melt-spun into an undrawn yarn, and a non-hydrous spinning oil having a water content of 5% or less is applied to the undrawn yarn;
Subsequently, the general formula % formula %) [However, Rf in the formula is a perfluoroalkyl group, and X is -
R-1-colR') -Q- or -302NCR'noQ- (where R is a divalent alkyl group, B' is hydrogen or a lower alkyl group, and Q is a divalent cyclic group), A and A' is 10-1-3- or -N(Z'horn-here Z
'represents hydrogen or a monovalent organic group), Z is a monovalent organic group, W is an organic group with a valence of 3 or more, a and b are a+b≧6
Indicates the integer. ] A water-repellent/oil-repellent/water-repellent product characterized by applying a composition containing the compound represented by the formula as a main component to the yarn in an amount of 0.03 to 2.00% by weight, and then subjecting the yarn to a stretching heat treatment. A method for producing synthetic fibers that are stain resistant. 2. Melt-spun the synthetic polymer to form an undrawn yarn, apply a water-containing spinning oil with a water content of 5% or more to the undrawn yarn, and then apply the general formula % to the undrawn yarn. ) [In the formula, Rf is) -fluoroalkyl group, X is -R-1-0ON(El')-Q-
CR')-Q-(where R is a divalent alkyl group R
/ represents hydrogen or a lower alkyl group, Q represents a divalent organic group), A and A' represent 10-, -S- or -N (Z'
)-(Here, 2' is hydrogen or 1 (1- indicates an organic group of 1111), 2 is a monovalent organic group, and W is a trivalent or higher valent organic group (
a and b represent integers such that a+b≧5, i−. ]
After adding 0.03 to 2,00% by weight of a composition containing a compound as a main component to the yarn, the yarn is subjected to drawing heat treatment to form a drawn yarn, and then A method for producing synthetic fibers having water-repellent, oil-repellent, and stain-repellent properties, characterized in that the drawn yarn is passed through a hot fluid jet nozzle to form a continuous bulky yarn.