JP2000282363A - Oiling agent for synthetic fiber - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an oiling agent which is used for synthetic fibers, has good heat resistance, scarcely causes the breakage of fibers, and is suitable for the fibers to be fed to processing processes accompanied by a heating process, by formulating a specific compound comprising an ether bond-containing dicarboxylic acid ester as a smoothing agent preferably with at least one of another smoothing agent, a surfactant, an antistatic agent, and the like. SOLUTION: This oiling agent for synthetic fibers contains 40 to 80 wt.% of a compound of the formula [OR1 is a monohydroxy compound residue; OA and OQ are each a 2C to 4C oxyalkylene; OR2 is OH or a monohydroxy compound residue; (p), (q) are each 0 to 30; (m) and (n) are each 1 to 6] as a smoothing agent compound, and preferably further 10 to 50 wt.% of another smoothing agent such as a fatty acid ester, 5 to 45 wt.% of a nonionic surfactant such as a higher alcohol alkylene oxide adduct, and 1 to 10 wt.% of an antistatic agent such as lauryl alcohol phosphoric acid ester sodium salt.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oil agent for synthetic fibers, and more particularly, it is used in the production and processing of fibers involving a heating step, and has a good heat resistance and stable operation without thread breakage. The present invention relates to an oil agent for synthetic fibers which can maintain good properties and can obtain a yarn having good performance with little fuzz.

[0002]

2. Description of the Related Art Conventionally, various oil agents have been used in the spinning and drawing steps of synthetic fibers according to the purpose. However, today, in order to improve productivity and quality, spinning and drawing speeds have been increased, and processing at high temperatures has led to a strong demand for improved lubricity and heat resistance of fiber oil agents.

Conventionally, lubricating components of synthetic fiber oils include paraffinic hydrocarbons such as mineral oil, natural oils such as rapeseed oil and coconut oil, and lauryl oleate, neopentyl dilaurate and oleyl oleate. Higher fatty acid esters such as ate and dioleyl adipate are known. However, they do not have sufficient heat resistance under recent severe spinning conditions.

[0004]

In order to solve this problem, an ester of a bisphenolalkylene oxide adduct described in JP-B-47-29474 has been proposed as a lubricant component having a low decomposition and low tar content. . However, while the heat resistance of these oils belongs to a fairly good class, they are inferior in smoothness, tend to cause single yarn winding during drawing, yarn breakage, or fuzz generation during high-speed twisting. However, it is not enough to obtain a high-strength yarn of higher quality.

[0005] Further, sulfur-containing esters described in JP-B-55-9114 and JP-B-55-9115 have been proposed as having low decomposition, low tar and good lubricity. However, the heat resistance of these treating agents belongs to the category of good, but because of their good heat resistance, they do not volatilize and remain on the hot stretching roller. It has a tendency to become a so-called tar, which tends to cause winding of single yarn during drawing, yarn breakage, or generation of fluff, and to obtain a high-quality yarn of higher quality in recent years stably for a long time. It is not enough to achieve both workability and quality.

[0006]

SUMMARY OF THE INVENTION The present inventors provide a synthetic fiber yarn with a high degree of smoothness and have an excellent heat resistance even under the severe heat treatment required in recent fiber production and processing steps. As a result of repeated studies for the purpose of obtaining an oil agent for fibers that has a property and enables smooth continuous heat treatment for a long period of time without hindering the yarn production, the present invention has been achieved.

That is, the present invention is an oil agent for synthetic fibers, which comprises an ester compound of a dicarboxylic acid having an ether bond represented by the following general formula (1).

[0008]

Embedded image

Wherein OR ₁ is a monohydroxy compound residue, OA and OQ are each independently a C ₂ -C ₄ oxyalkylene group, OR ₂ is OH or a monohydroxy compound residue, and p and q are each independently An integer from 0 to 30,
m and n are each independently an integer of 1 to 6

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, OR ₁ in the general formula (1) is a monohydroxy compound residue (a group excluding H in a hydroxyl group), for example, an aliphatic saturated alcohol, an aliphatic unsaturated There may be mentioned the residues of monohydric alcohols such as alcohols, cycloaliphatic alcohols, aromatic alcohols and the like and phenols. Although the carbon number of these residues is not particularly limited, it is usually 1 to 30, preferably 4 to 24.

Specific examples of the monohydroxy compound forming the above residue include monohydric alcohols such as methyl alcohol, ethyl alcohol, propyl alcohol, n-butyl alcohol, isobutyl alcohol, t-butyl alcohol, Linear or side chains such as isoamyl alcohol, octyl alcohol, 2-ethylhexyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, synthetic alcohols (eg, Ziegler alcohol, oxo alcohol, etc.) Aliphatic saturated alcohols having the formula:
Aliphatic unsaturated alcohols such as allyl alcohol, crotyl alcohol, propargyl alcohol, oleyl alcohol, and linoleyl alcohol; aliphatic saturated and unsaturated alcohols such as incense alcohol, tallow reduced alcohol, and palm oil reduced alcohol; Pentanol,
Alicyclic alcohols such as cyclohexanol and cycloheptanol; aromatic alcohols such as benzyl alcohol and cinnamyl alcohol; Examples of phenols include phenol, cresol, isopropylphenol, t-butylphenol,
Examples include aminophenol, octylphenol, nonylphenol, tetradecylphenol, octadecylphenol, oleylphenol, dinonylphenol and the like. Of these, preferred are monohydric alcohols, and more preferred are aliphatic monohydric alcohols.

OR ₂ in the general formula (1) is OH or a monohydroxy compound residue, and examples of the monohydroxy compound residue include the same examples as those described above. Preferred are the same. In the general formula (1), OA and OQ are each independently a C _{2 to} C ₄ oxyalkylene group (which may have a side chain), and include an oxyethylene group, an oxypropylene group, and an oxybutylene group. Of these, an oxyethylene group is preferred. The repetition of the oxyalkylene group may be the same or different. When two or more different oxyalkylene groups are contained, the mode of addition may be random addition or block addition.

In the general formula (1), p and q are each independently an integer of 0 to 30, preferably 1 to 25, more preferably 3 to 20. When p and q are more than 30, it becomes solid at room temperature, and the stability of the appearance cannot be maintained, and the viscosity of the whole oil agent is remarkably increased to cause problems such as thread breakage when spinning fine denier yarn. May cause. In the general formula (1), m and n are each independently 1
And an integer of 6 to 6, preferably 1 to 2. m,
When n exceeds 6, the heat resistance may be rather reduced.

The compound represented by the general formula (1) can be obtained by various known reactions. For example, it can be obtained by esterifying a corresponding dicarboxylic acid and a monohydroxy compound. Examples of the dicarboxylic acid include m,
A dicarboxylic acid (diglycolic acid) corresponding to the case where n is 1 and a dicarboxylic acid (di-glycolic acid) corresponding to the case where m and n are 2
β-hydropropionic acid) and dicarboxylic acids (di-γ-hydrobutanoic acid) corresponding to the case where m and n are 3, among which diglycolic acid and di-β-hydroacid are preferable. Propionic acid.

In the above esterification reaction, the ratio of dicarboxylic acid to monohydroxy compound is such that alcoholic hydroxyl group equivalent / carboxyl group equivalent is usually 1.3 to 0.3.
7, preferably 1.1 to 0.9. The reaction is usually carried out in the presence of a catalyst, usually at 100 to 200 ° C, preferably at 130 to 200 ° C.
The reaction is performed at 170 ° C., and can be performed under normal pressure, reduced pressure, or increased pressure. The reaction time is usually 2 to 10 hours. Examples of the catalyst include catalysts usually used in esterification reactions, for example, sulfonic acid salts such as paratoluenesulfonic acid and methanesulfonic acid; inorganic acids such as sulfuric acid; and metal-containing compounds such as dibutyltin oxide and zinc acetate. After the reaction, the compound of the present invention can be obtained usually by purification using an adsorbent such as diatomaceous earth and molecular sieve.

The dicarboxylic acid and the monohydroxy compound constituting the compound represented by the general formula (1) may be used as a mixture of two or more dicarboxylic acids and monohydroxy compounds.

In the oil agent of the present invention, the compound represented by the general formula (1) may be used alone or in combination of two or more. Further, it may further contain at least one of other leveling agents, surfactants and antistatic agents.

Other leveling agents include mineral oils (refined spindle oil, liquid paraffin, etc.), animal and vegetable oils (coconut oil, castor oil, etc.), and fatty acid esters having 8 to 60 carbon atoms (2-
Ethylhexyl palmitate, lauryl oleate, isostearyl laurate, oleyl oleate, dioleyl adipate, dioleyl thiodipropionate, diisostearyl thiodipropionate, etc., alkyl ether ester having a number average molecular weight of 400 to 2,000 (lauryl alcohol) Laurate of 3 moles of ethylene oxide adduct of ethylene oxide, ethylene oxide 3 of oleyl alcohol
Adipate of a molar adduct, an ester of an alkylene oxide adduct of a higher aliphatic alcohol such as thiodipropionate of a 5-mol adduct of ethylene oxide of isostearyl alcohol, and wax. Of these, fatty acid esters and alkyl ether esters are preferred.

The surfactant is preferably a nonionic surfactant, and the nonionic surfactant has a number average molecular weight of 400 to 400.
3000 higher alcohol alkylene oxide adducts (octyl alcohol ethylene oxide and / or
Or propylene oxide, ethylene oxide and / or propylene oxide adduct of stearyl alcohol, etc., alkylene oxide adduct of polyhydric alcohol ester (addition mole number 5 to 50, for example, 25 mol of ethylene oxide adduct of hydrogenated castor oil, sorbitan Trioleate ethylene oxide 20 mol adduct) and the like.

Examples of the antistatic agent include phosphates (sodium phosphate of lauryl alcohol, potassium phosphate of oleyl alcohol, etc.), phosphites (triphenyl phosphite, tridecyl phosphite, etc.), fatty acid soaps (olein, etc.). Acid soap, castor oil soap, etc.).

Further, the oil agent contains other additives and pH.
A modifier may be contained. Examples of the additive include a hindered phenol-based antioxidant such as an antioxidant (triethylene glycol-bis [3- (3-t-butyl-5-methyl-4-hydroxyphenyl) propionate]) and tetrakis [methylene-3]. -(Dodecylthio) propionate] thioether-based antioxidants such as methane, phosphite-based antioxidants such as tris (monononylphenyl) phosphite, etc., and ultraviolet absorbers (2- (5-methyl-2-hydroxyphenyl) Benzotriazole-based ultraviolet absorbers such as benzotriazole;
Hindered amine-based ultraviolet absorbers such as 6,6-tetramethyl-4-piperidyl) sebacate; silicon compounds (unmodified dimethyl silicone oil such as dimethylpolysiloxane; methylphenylpolysiloxane; polyether-modified polysiloxane; Modified silicone oil) and fluorine compounds (perfluorooctylsulfonic acid sodium salt, 2,2,3,3-tetrafluoro-1-propanol, etc.). Examples of the pH adjuster include alkali metals (such as sodium hydroxide and potassium hydroxide), alkylamine oxide adducts of alkylamine (3 mol adduct of laurylamine with ethylene oxide, and 10 mol adduct of stearylamine with ethylene oxide). can give.

The content of the compound represented by the general formula (1) in the entire treating agent is not particularly limited, but is usually from 10 to 100% by mass from the viewpoint of stabilization of a target yarn.
It is preferably from 10 to 90% by mass, particularly preferably from 40 to 80% by mass.

The content of the other leveling agent is usually 90% by mass or less, preferably 80% by mass or less, particularly preferably 10 to 50% by mass. The content of the surfactant is usually 70% by mass or less, preferably 60% by mass or less, and particularly preferably 5 to 45% by mass. The content of the antistatic agent is usually 20% by mass or less, preferably 15% by mass or less, and particularly preferably 1 to 10% by mass. The content of other additives is usually 10% by mass or less, preferably 8% by mass.
%, Particularly preferably 0.3 to 6% by mass. The amount of the pH adjuster added is usually 10% by mass or less, preferably 8% by mass or less, particularly preferably 0.03% by mass.
% To 6% by mass.

The oil agent of the present invention has excellent heat resistance and is used in the production and processing steps of fibers. In particular, filaments for industrial materials having high strength made of thermoplastic synthetic fibers such as nylon and polyester are used. Suitable for the production process of fibers that require a severe heat process such as yarn and false twisted yarn.

The oil agent of the present invention is supplied to the spun yarn by treating it in a non-water-containing state or in an emulsion state emulsified with water in the melt fiber spinning step of the synthetic fiber.
In the case of a non-water-containing treating agent, it is used as crude oil or diluted with a diluent (such as a low-viscosity mineral oil). The dilution ratio is usually 20 to 80% by mass, preferably 30 to 70% by mass. The concentration of the emulsion is usually 5 to 30% by mass, preferably 10 to 25% by mass.

There is no particular limitation on the oiling method, and nozzle oiling and roller oiling can be applied. The amount of the oil agent is usually 0.3 to 2.0% by mass, preferably 0.5 to 1.5% by mass, based on the fiber.

[0027]

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 Compounds (No. 1 to No. 1) of the present invention shown in Table 1 below
6) and conventional oil agent components (Nos. 7 to 9)
Tarification after leaving in a circulating air dryer at 240 ° C. for 4 hours and 8 hours, and 1% adhesion of a commercially available 1260 denier nylon filament yarn to a sample yarn obtained by drying at the tip of a metal tip, and metal friction by a running yarn method. Table 2 shows the results of measuring the coefficients.

[0029]

[Table 1]

[0030]

[Table 2]

Example 2 The following oils (Nos. AF) and comparative oils (Nos. GI) of the present invention were tarified after being left in a circulating drier at 240 ° C. for 4 hours and 8 hours. And a commercially available one
Table 3 shows the results obtained by attaching 1% to a sample yarn obtained by washing and drying a 260 denier nylon filament yarn with hot water and measuring a coefficient of friction against metal by a running yarn method.

(Oil Agent A of the Present Invention) 160 mass% hydrogenated castor oil (EO) ₂₅ 25 mass% Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate ester sodium salt of lauryl alcohol 2% by mass (Oil agent B of the present invention) 2 60% by mass Hardened castor oil (EO) ₂₅ 25% by mass Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate sodium salt of lauryl alcohol 2% by mass (Oil agent C of the present invention) 3 40 mass% oleyl oleate 20 mass% hydrogenated castor oil (EO) ₂₅ 25 mass% Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate ester sodium salt of lauryl alcohol 2% by mass (Oil agent D of the present invention) 4 60% by mass Hardened castor oil (EO) ₂₅ 25% by mass Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Lauryl alcohol phosphate ester sodium salt 2% by mass (Oil E of the present invention) 5 40% by mass Dioleyl adipate 20% by mass Hardened castor oil (EO) ₂₅ 25% by mass Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Lauryl alcohol phosphate ester sodium salt 2% by mass (Oil agent F of the present invention) 6 40 mass% oleyl oleate 20 mass% hydrogenated castor oil (EO) ₂₅ 25 mass% Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13 mass% Lauryl alcohol phosphate sodium salt 2 mass%

(Comparative Oil Agent G) Dioleyl adipate 60% by mass Hardened castor oil (EO) ₂₅ 25% by mass Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate ester sodium salt of lauryl alcohol 2% by mass (Comparative oil H) Bisphenol (EO) ₂ Dilaurate 60% by mass Hardened castor oil (EO) ₂₅ 25% % Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate ester sodium salt of lauryl alcohol 2% by mass (Comparative oil solution I) Dioleyl thiodipropionate 60% by mass Hardened castor oil (EO) ₂₅ 25% % Octyl alcohol (PO) ₁₀ (EO) ₂₀ block adduct 13% by mass Phosphate sodium salt of lauryl alcohol 2% by mass In the above notation, E in the components represents an ethylene group, and P represents a propylene group.

[0034]

[Table 3]

Evaluation Evaluation of tar formation ：: No tar conversion ○: Slight tar conversion △: About half of tar conversion ×: Tar conversion

[0036]

The oil agent for synthetic fibers according to the present invention has excellent heat resistance and smoothness at the time of production, and exhibits excellent spinning properties during melt spinning and stretching of polyester and nylon. In particular, by applying the oil agent of the present invention, long-term heat resistance can be improved, and the smoothness is good, so that stable operability can be maintained.

Claims (3)

[Claims] 1. An oil agent for synthetic fibers comprising a compound represented by the following general formula (1) as a smoothing agent component. Embedded image Wherein OR ₁ is a monohydroxy compound residue, OA and OQ are each independently a C ₂ -C ₄ oxyalkylene group, OR ₂ is OH or a monohydroxy compound residue,
p and q are each independently an integer of 0 to 30; m and n are each independently an integer of 1 to 6; 2. The synthetic fiber oil preparation according to claim 1, further comprising at least one selected from other leveling agents, surfactants and antistatic agents. 3. A compound represented by the general formula (1):
The synthetic fiber according to claim 2, comprising 80% by mass, 10 to 50% by mass of another leveling agent, 5 to 45% by mass of a surfactant, and 1 to 10% by mass of an antistatic agent. Oil agent.