JPH01246471A - Lubricant for treatment of thermoplastic synthetic fiber - Google Patents

Abstract

PURPOSE:To produce the subject lubricant emitting little fume, free from production of tarry substance and having excellent heat-resistance, by using a lubricant component consisting of a compound having a specific kinetic viscosity and produced by reacting a specific ester compound with an olefin in the presence of a radical generator. CONSTITUTION:A >=30C monoester compound (e.g., tridecyl stearate) is made to react with an olefin in the presence of a radical generator such as an organic peroxide (e.g., alkyl peroxide) to obtain a compound having a kinetic viscosity increased to 1.2-50times the kinetic viscosity of the ester compound at 40 deg.C. When a lubricant for textile treatment containing said product as a lubricant component is supplied in the form of e.g., an emulsion to a production process of a thermoplastic synthetic fiber, e.g., a thermal drawing or false-twisting process, it exhibits excellent heat resistance to prevent the formation of tar and the generation of fume and keeps the operation efficiency. The libricant especially satisfies the requirement of the recent high-speed processing. The olefin is preferably a 4-30C alpha-olefin.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a treatment oil for thermoplastic synthetic fibers, and particularly to a treatment oil for thermoplastic synthetic fibers that undergoes a heating process.

[Conventional technology]

Conventionally, when producing thermoplastic synthetic fibers, the spun yarn is heated to draw it using a melt-spinning method, or heat-set is performed to improve its properties.

In addition, thermoplastic synthetic fibers that undergo a false twisting process are generally heat treated to fix their shape, and synthetic fibers used for industrial materials such as tire cord yarns are It is customary to draw under severe heating conditions to obtain strength yarns. In various manufacturing processes, fiber threads are often processed at fairly high speeds, and in order to smoothly proceed with processes such as spinning, drawing, and processing, fiber threads are highly heat resistant to processing oils that are treated with them. , smoothness, and antistatic properties are required.

In order to satisfy these demands, esters of mineral oils, higher alcohols and fatty acids, and esters of dibasic acids such as adipic acid and sebacic acid have been used as lubricant components to be blended with emulsifiers, charged spinning agents, etc. Fatty acid esters of polyhydric alcohols such as trimethylolpropane, glycerin, etc. have been used.

[Problem to be solved by the invention]

However, although these conventionally used processing oils exhibit good smoothness, they are not suitable for thermoplastic synthetic fiber yarns that undergo particularly harsh heating processes such as hot drawing and false twisting processes. They do not have sufficient heat resistance, and they emit smoke, which worsens the working environment, and tar-like substances are formed on the heater, causing noticeable dirt in the yarn path, resulting in single yarn wrapping and yarn breakage. As a result, smooth stretching and false twisting cannot be performed, and the machine must be stopped and cleaned to remove the tar-like substance, causing process troubles and reducing efficiency. Furthermore, in conjunction with the recent speeding up of textile manufacturing processes, there is an increasingly strong demand for strengthening environmental protection in the regions where textile manufacturers are located (for example, to prevent air volition due to smoke generation). It became necessary to improve the heat resistance of the stage.

[Means to solve the problem]

Therefore, in view of this situation, the present inventors conducted repeated studies in order to suppress the generation of smoke and tar-like substances during the heating process, and as a result, they arrived at the present invention.

That is, the present invention combines a monoester compound having 30 or more carbon atoms and an olefin with a kinematic viscosity at 40°C (JIS
; JIs 2283-1956. JIS Z 8
803-1959) in the presence of a radical generator so that the amount is 1.2 times or more and 50 times or less of the original ester compound, as a lubricant component. The present invention provides an oil agent for treating synthetic fibers.

The synthetic fiber treatment oil of the present invention emits virtually no smoke and does not form tar-like substances.

The compounds of the present invention can be readily prepared by known methods, for example: J.C., J.Cem.

Soc, 1918 (1965), by the addition reaction of fatty acid esters and olefins.

As the raw material ester compound in the present invention, tridecyl stearate, oleyl oleate, octyl dodecyl oleate, etc. can be used, but are not necessarily limited to these.

In addition, the type of olefin is not particularly limited, but
Preferably, α-olefins have a C3 degree or less, particularly C4 to C3 degrees, and more preferably C6 to C2 degrees. The amount of olefin added is preferably at most two equivalents of the ester group, particularly preferably at most one equivalent.

When adding an olefin to an ester compound,
It is necessary to use a radical generator, such as peroxides, azobis compounds, radiation, etc. Among these, it is desirable to use organic peroxides, and particularly good organic peroxides include dialkyl peroxide, hydroperoxide, diacyl peroxide,
These include peroxy esters, ketone peroxides, peroxy dicarbonates, and peroxy ketals. Specific examples include ditertiary butyl peroxide, dicumyl peroxide, and tertiary butyl hydroperoxide.

The amount of the radical generator to be used is preferably 0.01 to 5 times the amount of the olefin by mole, particularly preferably 0.05 to 2 times the amount by mole.

As for the reaction conditions for adding an olefin to an ester compound, there is a known method for boat fishing in which an olefin and a radical generator are added to an ester compound heated to 50 to 250°C, but this method is not always possible. It is not limited to.

Alternatively, a method of adding a radical generator to a mixture of an ester compound and an olefin may be used.

The compound thus obtained has a kinematic viscosity at 40°C of 1.2 to 50% of the kinematic viscosity of the original ester compound.
times, preferably 1.5 to 20 times.

If it is smaller than 1.2 times, the heat resistance will not be sufficient, and if it is larger than 50 times, the lubricity will be poor.

In addition to the compounds of the present invention, the oil for treating thermoplastic synthetic fibers used in the present invention may optionally include known lubricants (for example, aliphatic monoesters such as lauryl oleate, oleyl oleate, dioleyl adipate, dioctyl phthalate, Dibasic acid diesters and dihydric alcohol diesters such as pentyl glycol diolate and ethylene glycol diolate, polyhydric alcohol esters such as trimethylolpropane trilaurate, glycerin triolate, and pentaerythritol tetraoleate, triisostearyl trimellitate etc.), polyoxyethylene sorbitan esters, emulsifiers such as ethylene oxide adducts of hydrogenated castor oil, higher alcohol ethylene oxide adducts, and higher fatty acid ethylene oxide adducts, as well as alkyl phosphate potassium salts and oleic acid. Antistatic agents such as potassium, imidapurine-type amphoteric active agents, and betaine-type amphoteric active agents can be mixed and used.

Therefore, the lubricating treatment composition of the present invention can be emulsified in water to form an aqueous emulsion by a conventional method, or dissolved in a low-viscosity diluting solvent, and applied to fiber yarn by one oiling roller method, spray method, nozzle oiling method, etc. 0.2 to 2.0% by weight of oil is added to the strip.

Thermoplastic synthetic fibers treated with the lubricating composition of the present invention exhibit very excellent heat resistance and do not emit smoke on heater plates or rollers heated to 160 to 250°C during the hot drawing or heat setting process. It does not deteriorate the working environment or generate tar-like substances on the heater, which reduces work efficiency. Furthermore, it exhibits good lubricity as well as those conventionally used.

〔Example〕

Hereinafter, the present invention will be explained in detail with reference to synthesis examples and examples, but the present invention is not limited to these synthesis examples and examples.

Synthesis Example 1 Tridecyl stearate 139.8 g (0,3n
1-dodecene 50.4 g (0,3n
ol) and radical generator ditertiary butyl peroxide (hereinafter abbreviated as DTBPO) 43.8 g (
0.3nol) at 190°C under nitrogen atmosphere.
After the dropwise reaction took place over a period of time, it was aged at 190°C for 30 minutes, and then unreacted olefin was removed at 150-190°C/10-3nuaf1g to obtain 165.2g of Compound A.

Synthesis Example 2 Tridecyl stearate 139.8 g (0,3n
1-dodecene 50.4 g (0,3n
A mixture of 1.9 g (0.15 nol) of DTBPO and 1.9 g (0.15 nol) of DTBPO was reacted dropwise at 190°C under a nitrogen atmosphere for 2 hours, and then aged at 190°C for 30 minutes.
Unreacted olefin was removed at 90° C./10-3 n+mHg to obtain 8185.4 g of compound.

Synthesis Example 3 Tridecyl stearate 139.8 g (0,3n
+ol) to l-dodecene 50.4 g (0,3
nol) and DTBPO13,1g (0,09nol)
The mixture was reacted dropwise at 190°C under nitrogen aeration for 2 hours, then aged at 190°C for 30 minutes, and then heated at 150°C.
Unreacted olefin was removed at 190°C/10-3 mmHg to obtain 61.0 g of compound CI.

Synthesis Example 4 Tridecyl stearate 139.8 g (0,3n
l-dodecene 50.4 g (0,3n
ol) and DTBPO.

A mixture of '-4g (0.03nol) was added dropwise at 190°C under nitrogen aeration for 2 hours, and then reacted for 3 hours at 190°C.
Aged for 0 minutes, then 150-190℃/10-3
Remove unreacted olefin with mmtlg to prepare compound D1
62.0g was obtained.

Synthesis Example 5 Tridecyl stearate H39.8g (0.3nol
) to 1-hexadecene 67.2 g (0,3n
A mixture of 43.8g (0.3nol) of DTBPO and 43.8g (0.3nol) of DTBPO was reacted dropwise at 190°C under a nitrogen atmosphere for 2 hours, and then aged at 190°C for 30 minutes.
Unreacted olefin was removed at 90° C./10-3 mm (11 g) to obtain 189.3 g of Compound E.

Synthesis Example 6 Tridecyl stearate 139.8 g (0,3n
ol) to l-octene 33.6 g (0,3n
A mixture of 43.8g (0.3nol) of DTBPO and 43.8g (0.3nol) of DTBPO was reacted dropwise at 190°C under nitrogen aeration for 2 hours, and then aged at 190°C for 30 minutes.
Unreacted olefin was removed at 0° C./10 to 3 mmHg to obtain 155.7 g of compound F.

Synthesis Example 7 Oleyl oleate 159.6 g (0.3 mol)
50.4 g (0.3 mol) of l-dodecene
A mixture of 43.8 g (0.3 mol) of Tokuchi TBPO was reacted dropwise at 190°C under a nitrogen atmosphere for 2 hours, and then aged at 190°C for 30 minutes, and then aged at 150 to 190°C.
/10-3 mm) Unreacted olefin was removed with Ig to obtain 9.7 g of compound c 1B.

Synthesis Example 8 Octyldodecyl oleate 168.6 g (0.3m
l-dodecene 50.4 g (0.3 m
A mixture of 43.8 g (0.3 mol) of DTBPO and 43.8 g (0.3 mol) of DTBPO was reacted dropwise at 190°C under a nitrogen atmosphere for 2 hours, and then aged at 190°C for 30 minutes, and then 150-19
Unreacted olefin was removed at 0° C./10-3 mm to obtain 197.4 g of compound H.

Synthesis Example 9 Tridecyl stearate 139.8 g (0,3+
++ol) to l-dodecene 50.4g (0,3
mol) and tert-butyl perbenzoate 58.
A mixture of 26 g (0.3 mol) was reacted dropwise at 170°C under nitrogen atmosphere for 2 hours, and then reacted at 170°C for 30 hours.
Aged for minutes, then 150-190℃/10-3 mo
+Hg to remove unreacted olefin and compound 1 162
．． 2 g was obtained.

Synthesis Example 1O Tridecyl stearate 139.8 g (0.3 m
1-dodecene 50.4 g (0.3 m
ol) and tert-butyl hydroperoxide 2
A mixture of 7.0 g (0.3 mol) was reacted dropwise at 230°C under nitrogen aeration for 2 hours, and then reacted at 230°C for 2 hours.
Aging for hours, then 150-190℃/10-3mmH
Compound J was obtained by removing unreacted olefin at 160.5 g.
I got g.

Table 1 shows the synthesis conditions for the above-mentioned compounds of the present invention and a comparison of kinematic viscosity with conventionally used esters that are their raw materials.

Example 2 Table 2 shows the results of a comparative study of the heat resistance of the compounds A-J of the present invention shown in Table 1 and the conventionally used esters -M as their raw materials.

To measure the amount of smoke generated, a sample was dropped onto a heater at 240'C, and smoke generation was visually determined. Also, 0.5 in aluminum cup
A sample of 1 g was taken, and the weight loss rate after standing at 240'C for 4 hours and the residual rate after washing with acetone were measured to obtain the volatile content and tar conversion rate. From Table 2, it can be seen that the compounds of the present invention exhibit very excellent heat resistance, have low amounts of smoke and volatile matter, and do not form tar-like substances.

Table 2 Example 2 Compounds A-J of the present invention listed in Table 1 and -M were used as the conventionally used esters as their raw materials, and were blended with three types of surfactants as shown in Table 3. An oil agent for treating thermoplastic synthetic fibers was prepared.

Apply this oil to polyester 1000D yarn at 1.0% OPU.
The fiber-to-metal dynamic friction coefficient and the fiber-to-metal static friction coefficient were tested and evaluated at a bottle temperature of 230° C. using a chrome-plated matte pin as a friction body. The compositions of the oil agents and the test results conducted on them are shown in Table 3. Table 3 shows that the lubricating properties of the oil containing the compound of the present invention are comparable to those of conventional products.

Claims (1)

[Scope of Claims] 1. A monoester compound having 30 or more carbon atoms and an olefin are combined with a kinematic viscosity at 40°C (JIS;
2283-1956, JIS Z8803-1959) in the presence of a radical generator so that the amount is 1.2 times or more and 50 times or less of the original ester compound. An oil agent for treating thermoplastic synthetic fibers. 2.Claim 1, wherein the olefin has 4 to 30 carbon atoms.
The oil agent for treating thermoplastic synthetic fibers described above.