JPS626031B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a treatment oil for synthetic fibers, and more particularly to a treatment oil for synthetic fibers that has excellent antistatic properties and fiber bundle cohesiveness at low humidity, and does not cause roller winding. In general, as spinning oils for synthetic fibers, oils containing alkyl phosphate K salt as the main ingredient and nonionic surfactants such as alkyl sulfates, higher alcohols, or ethylene oxide admixtures of fatty acids are widely used. . However, these lubricants have insufficient antistatic properties in low humidity conditions, which generates static electricity, which causes cylinder winding in cards, dot roll-up, and coil tube clogging. Furthermore, due to the lack of convergence of the fiber bundles, there is a drawback that in the carding process and drawing process, the amount of sliver stored in the can is small, reducing work efficiency. To prevent static electricity under low humidity, increase the phosphorylation degree and monoester ratio of alkyl phosphate esters. Alternatively, it may be possible to use cationic surfactants or amphoteric surfactants, but these surfactants are highly hygroscopic and
It has the disadvantage of causing roller wrapping and rusting of the metal parts of the spinning machine. In addition, it is possible to improve the cohesiveness of fiber bundles by using animal and vegetable oils, fatty acid esters, fatty acid soaps, or nonionic surfactants such as higher alcohols or ethylene oxide adducts of fatty acids. For example, if a large amount of these ingredients is used,
If it is used in an amount of 30% by weight or more, it has serious drawbacks such as poor opening properties, high stickiness of the oil agent that causes roller sticking, and further deterioration of antistatic ability. As described above, in conventional spinning oils, when the antistatic property under low humidity is improved, the hygroscopicity increases and roll-up occurs. Alternatively, increasing the cohesiveness of fiber bundles may result in poor opening properties.There is still no oil agent that can solve all of the properties necessary for spinnability, such as antistatic properties, cohesiveness, roller winding properties, and smoothness. The current situation is that it has not been developed. The inventors of the present invention have conducted intensive studies to develop an oil agent that has excellent antistatic properties and fiber bundle convergence properties under low humidity conditions and does not cause roller wrapping. ester, and that excellent effects can be achieved by further containing a phosphate ester-based anionic surfactant in the N-acyl sarcosinate and oxyalkylene derivative ester. Heading, we arrived at the present invention. That is, the present invention provides N-acyl sarcosinate
(A) and an oxyalkylene derivative ester (B) (No. 1)
Invention): A synthetic fiber processing oil (second invention) characterized by containing the above (A) and (B) and a phosphate ester anionic surfactant (C). In the present invention, as the N-acyl sarcosinate (A), those represented by the following general formula (1) can be used. [In the formula, R represents a hydrocarbon group having 6 or more carbon atoms, and M represents a cation. ] In general formula (1), R has 6 to 30 carbon atoms
(preferably 8 to 22) straight-chain or branched, saturated or unsaturated, aliphatic, cycloaliphatic or aromatic hydrocarbon groups such as alkyl groups, alkenyl groups,
Examples include a cycloalkyl group, an alkylaryl group, and an allyl group. Examples of the acyl group RCO- are enantoyl, capryloyl, pelargoyl,
Examples include saturated aliphatic acyl groups such as caproyl, lauroyl, tridecyl, myristoyl, palmitoyl, and stearoyl; unsaturated aliphatic acyl groups such as oleoyl; and aromatic acyl groups such as benzoyl, toluoyl, cinnamoylnaphthoyl, and salicyloyl. Among these, preferred are aliphatic acyl groups such as lauroyl, stearoyl, and oleoyl. Examples of M include H or alkali metals such as sodium, potassium, and lithium; ammonium; and organic amine cations such as mono-, di-, or triethanolamine, propanolamine, and cyclohexylamine. As the oxyalkylene derivative ester (B) in the present invention, those represented by the following general formula (2) are used. [In the formula, R ₁ is a polyhydric alcohol residue or a carboxylic acid residue (residue excluding an active hydrogen atom); A is an alkylene group; R ₂ is an acyl group or an alkyl group,
Alkenyl group, cycloalkyl group, alkylaryl group, aryl group or aralkyl group (but
If R ₁ is a polyhydric alcohol residue, an acyl group);
_R3 is H, an acyl group or an alkyl group, an alkenyl group, a cycloalkyl group, an alkylaryl group,
Aryl group or aralkyl group; n and m are integers of 0 or 1 or more (however, if R ₁ is a carboxylic acid residue and R ₂ or/and R ₃ is an acyl group, n
and/or m is not 0), and at least one of p n's and q m's is 1 or more; p is an integer of 1 or more (however, if R ₁ is a polyhydric alcohol residue, 2 (an integer greater than or equal to); q represents an integer greater than or equal to 0 or 1; ] In general formula (2), the polyhydric alcohol residue of R ₁ includes aliphatic polyhydric alcohols, such as alkylene glycols such as ethylene glycol, propylene glycol, butylene glycol, neopentyl glycol, and hexylene glycol, trimethylolpropane, Trihydric or higher alcohols such as glycerin, hexanetriol, pentaerythritol, sorbitan, sorbitol, sucrose; amine polyols such as di- or triethanolamine, propanolamine, alkyldicalkanolamines (alkyldiethanolamines, etc.), tetra(hydroxyalkyl) ) Alkylene diamines; sulfur-containing polyols such as thiodiglycol; oxyalkylated products (ethylene oxide and/or propylene oxide adducts) of aromatic polyhydric alcohols such as polyhydric phenols [such as hydroquinone, bisphenols (bisphenol A, etc.)]
Examples include residues of polyhydric alcohols such as. Examples of the carboxylic acid residue for R ₁ include the following carboxylic acid residues. (1) Monocarboxylic acid: linear or branched aliphatic monocarboxylic acid (C2-30 preferably C8-22)
For example, acetic acid, propionic acid, caprylic acid, 2
- Ethylhexane, lauric acid, stearic acid, isostearic acid, montanic acid, oleic acid, linoleic acid, erucic acid, coconut oil fatty acid,
Palm oil fatty acids, tallow fatty acids; alicyclic carboxylic acids such as cyclohexanoic acid; aromatic monocarboxylic acids such as benzoic acid, toluic acid, cinnamic acid, naphthoic acid, etc. (2) Dicarboxylic acid: fatty acid dicarboxylic acid (C3~
40) For example, succinic acid, adipic acid, sebacic acid, dimer acid (dimer of C18 fatty acids); aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid. (3) Tricarboxylic acids: aliphatic tricarboxylic acids such as tricarballylic acid, aromatic tricarboxylic acids such as benzenetricarboxylic acid (such as trimellitic acid). (4) Ether or thioether-containing carboxylic acid: general formula (3) [In the formula, X is O or S; R' and R'' represent the same or different alkylene groups (preferably C1 to 6)] Oxydicaproic acid; thiodiacetic acid, thiodipropionic acid, thiodicaproic acid, etc.). (5) Oxycarboxylic acid: Aliphatic oxycarboxylic acid such as lactic acid, α-oxybutyric acid, tartaric acid, citric acid; Aromatic oxycarboxylic acid such as salicylic acid (6) Amino acids: aliphatic amino acids such as β-alanine; aromatic amino acids such as o-, m- or p-aminobenzoic acid, etc. Among these carboxyl group-containing compounds, preferred are 2-ethylhexanoic acid, These are aliphatic monocarboxylic acids such as lauric acid, oleic acid, and isostearic acid, and dicarboxylic acids such as adipic acid, sebacic acid, and thiodipropionic acid.In the general formula (2), the acyl groups of R ₂ and R ₃ are Examples include the acyl groups of monocarboxylic acids listed in the section of carboxylic acid residues. Examples of the alkyl groups for R ₂ and R ₃ include C1-30, preferably C1-20 straight-chain and/or branched alkyl groups, such as methyl. , propyl, butyl, octyl, 2-ethylhexyl, lauryl, tridecyl, stearyl; alkenyl groups include C8-22 alkenyl groups, such as oleyl; cycloalkyl groups, such as cyclohexyl; alkylaryl groups, include alkyl (C1-22); 20) Substituted phenyl groups such as tolyl, cumyl, octylphenyl, nonylphenyl groups; Aryl groups include phenyl, naphthyl, styrenated phenyl groups, etc.; Examples of aralkyl groups include benzyl groups. Multiple R ₂ and R ₃ exist. In the general formula ( ₂ ), at least one of R ₁ , R ₂ , and R ₃ has 6 or more carbon atoms (especially 8 to 22). In the case of a polyhydric alcohol residue or a polyhydric carboxylic acid residue, at least one of p R ₂ and q R ₃ has 6 or more carbon atoms (especially 8 to 8 carbon atoms).
22) is preferred. In general formula (2), A includes an alkylene group having 2 to 4 carbon atoms. Oxyalkylene group -
The alkylene oxides (hereinafter abbreviated as AO) used to form AO- include ethylene oxide (hereinafter abbreviated as EO), propylene oxide (hereinafter abbreviated as PO),
), 1.2-, 2.3-, 1.3- or 1.4-butylene oxide, and combination systems thereof (random and block).
This is a combination system of EO and other AOs (PO, etc.) (especially those with EO of 50% or more). n A's and m A's in the oxyalkylene chain -(AO) _o -, -(AO) _n - may be the same or different,
Further, p -(AO) _o - and q -(AO) _n - may be the same or different. The number of moles of AO added is preferably 1 to 10 moles per functional group. A.O.
If the number of moles added is less than 1 mole per functional group, it is undesirable in terms of antistatic ability, and if the number of moles added exceeds 10 moles, the tackiness of the oil increases, which is undesirable. p is an integer of 1 or more, usually 1 to 8
Preferably it is 1 to 4 (provided that when R ₁ is a polyhydric alcohol residue, it is an integer of 2 or more). q is an integer of 0 or 1 or more, usually 0 to 4, preferably 0 to 2
It is. The AO derivative esters represented by the general formula (2) include the following: [] Those in which R ₁ is a monocarboxylic acid residue: (1) Esters of monohydric alcohol AO adducts and monocarboxylic acids, e.g. Methanol (EO) ₃ laurate (laurate, a molar adduct of methanol with EO3. The same expression will be used hereinafter), Methanol (PO) ₅ oleate, Octyl alcohol (EO) ₄ stearate, Lauryl alcohol (EO) ₂ stearate, oxocol
1415 (EO) _3laurate ; (2) Phenols or substituted phenols AO
Adduct monocarboxylic acid esters such as cumylphenol (EO) _3laurate . [] Those in which R ₁ is a polyhydric alcohol residue: Poly(di, tri, tetra, etc.) esters of polyhydric alcohol AO adducts and monocarboxylic acids, such as dilaurate of PEG300 (polyethylene glycol with a molecular weight of 300), PEG300 distearate; Glycerin (EO) ₃ G or Tri Stearate, Glycerin (PO) ₃ (EO) ₃
Tristearate, trimethylolpropane (EO) ₅ Trilaurate, trimethylolpropane (EO) ₂₀ Tristearate, sorbitol (EO) ₁₅ Tristearate, sorbitol (EO) ₄₀ Tetrastearate; triethanolamine (EO) ₅ tribehenate, triethanolamine (EO) ₃ trilaurate; bisphenol A (PO) ₂ (EO) ₄ dilaurate; thiodiglycol (EO) ₄ distearate, etc. [] Those in which R ₁ is a polyhydric carboxylic acid residue: Esters of AO adducts such as monohydric alcohols, monocarboxylic acids, phenols, substituted phenols, etc. and polyhydric carboxylic acids, such as dimethanol (EO) ₃ adipate, Dilauryl alcohol (EO) ₃ adipate, dinonylphenol (EO) ₂ adipate, trilauryl (EO) ₂ trimellitate, dilauryl (EO) ₂ thiodipropionate, etc. These oxyalkylene derivative esters are 2
More than one species may be used in combination. Among these oxyalkylene derivative esters, preferred are monocarboxylic acid esters of monohydric alcohol AO adducts, diesters of monohydric alcohol AO adducts and dihydric carboxylic acids, and diesters of dihydric alcohol AO adducts and monocarboxylic acids. It is a triester of a diester and a trihydric alcohol AO adduct with a monocarboxylic acid. As for the degree of esterification of the oxyalkylene derivative, it is preferable to completely esterify it from the viewpoint of preventing roller sticking. in AO derivative ester
Those having an EO content of 5 to 90% by weight (especially 10 to 50%) are preferred. In the second invention, the phosphate ester-based anionic surfactant (C) used together with (A) and (B) is a higher alcohol having 8 to 30 carbon atoms (linear, unsaturated, or branched are fine). Or, its AO adduct or alkylphenol (alkyl group has 4 carbon atoms)
Phosphate ester (mono and/or di-ester) salts of the AO adducts of ~20) can be used. Examples of neutralizing salts include metal salts such as Na and K, ammonium salts, and organic amine salts such as mono-, di-, or tri-ethanolamine and propanolamine. Higher alcohols used in the production of phosphate ester-based anionic surfactants include natural alcohols (lauryl alcohol, stearyl alcohol, etc.), synthetic alcohols [Tigra alcohol; oxo alcohols such as Dovanol (Ciel Chemical), Oxocol (Nissan Chemical) , Diamond Doll (manufactured by Mitsubishi Kasei)
etc., tridecyl alcohol]; Examples of the alkylphenol include octylphenol and nonylphenol. Specific examples of phosphate ester-based anionic surfactants include JP-B No. 50-30199, JP-A-50-194, JP-A-46-9880, and JP-A-Sho 38-
Examples include those described in Publication No. 12524 and the like. (A) in the present invention (first invention, second invention),
In addition to (B) and (C), various conventionally known smoothing agents and various surfactants can be used in combination if necessary. Such substances include mineral oils, animal and vegetable oils,
Smoothing agents such as fatty esters, waxes, and higher alcohols; Nonionic surfactants such as alkyleoxide adducts of higher alcohols or fatty acids; Anionic surfactants such as alkyl sulfates, alkyl ether sulfates, sulfonates, and fatty acid soaps; Various surfactants such as cationic surfactants other than quaternary ammonium salts, (primary to tertiary amine salt type, sulfonium salt type, phosphonium salt type, arsonium salt type), amphoteric surfactants such as alkyl betaines, etc. can be mentioned. In the first invention, the contents of (A) and (B) are ( A)
The content of (B) is usually 1 to 30% by weight, preferably 5 to 20% by weight, and the content of (B) is usually 10 to 90% by weight, preferably 20 to 80% by weight. The weight ratio of (A) and (B) is usually 1:0.3 to 1:90, preferably 1:1 to 1:16. If the content of (A) is less than 1% by weight, the antistatic effect of the treated oil will be poor, and if it exceeds 30% by weight, the tackiness of the treated oil will increase, causing roller sticking, which is undesirable. Furthermore, if the content of (B) is less than 10% by weight, the opening properties and smoothness of the treated oil will be poor, resulting in poor card passage and neps, and if it exceeds 90% by weight, the antistatic properties of the treated oil will deteriorate. This is not preferable as it tends to reduce the effectiveness. The second invention further improves card passage property and antistatic property by further containing (C) in (A) and (B) in the first invention, and (C)
The content of is usually 10% based on the weight of the entire treated oil (treated oil containing (A), (B), and (C)).
~89% by weight, preferably 30-80% by weight. [(A)
+(B)] and (C) is preferably 1:0.1 to 1:8, particularly 1:0.4 to 1:4. The weight ratio of (A) and (C) is usually 1:0.3 to 1:89, preferably 1:0.75 to
It was 1:13. When the content of (C) is less than 10% by weight, the opening properties of the treated oil tend to decrease, and
If it exceeds 89% by weight, the treated oil will have poor cohesiveness and is not preferred. In the treated oil agent of the present invention, the blending amounts of (A), (B), (C) and other components can be varied depending on the treatment purpose, treatment method, etc. An example of the blending amount (wt%) is as follows: Total of (A), (B), and (C): 21 to 100% (preferably 50 to 100%)
100%) Smoothing agent component: 0-50% (preferably 0-20%) Other surfactants: 0-50 (preferably 0-25%) Other additives: 0-5% (preferably 0-20%) 5
%) The treated oil agent of the present invention can be used in the spinning process of all synthetic fibers such as polyamide fibers, polyester fibers, acrylic fibers, polypropylene fibers, and polyvinyl fibers. The method of using the treated oil agent of the present invention can be the same as in conventional methods, for example in the form of an emulsion emulsified with water (the concentration of the treated oil agent is usually 1 to 10% by weight) or water-free (crude oil or organic solvent solution). Lubricating can be carried out at any position in the synthetic fiber manufacturing process by a known lubricating method such as a roller lubricating method, an immersion lubricating method, or a spray lubricating method. Alternatively, after applying the treatment agent by the immersion oiling method, the treated fibers can be subjected to dry heat treatment and then re-oiled again by the spraying method. It can be applied at various stages such as the spinning process, the process immediately before drawing, and the drawing process; the fibers can be in various forms, such as filament yarn (multifilament yarn) - staple, undrawn yarn - drawn yarn, etc. Can be mentioned. The amount of treatment agent deposited is usually 0.05 to 3% as a solid content based on the fiber.
(Weight) Preferably 0.08 to 0.3%. The treated oil agent containing (A) and (B) of the present invention is an oil agent that has excellent antistatic properties and fiber bundle cohesiveness at low humidity, and is less likely to roll around with a roller. Furthermore, the treated oil agent of the second invention further containing (C) has excellent card passing properties and synergistically excellent antistatic properties. The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
(Parts indicate parts by weight.) Example 1 A polyester staple (1.5 d, 38 mm) was lubricated with 0.15% by weight of the following treatment oil using the immersion lubricating method at 20°C and at a humidity of 40% RH. After aging under conditions of 80% RH for a day and night to reach an equilibrium moisture content, a spinning test was conducted and the results are shown in Tables 1 and 2. Oil agent A (product of the present invention) PEG-300 distearate 85 parts oleyl sarcosinate K salt 15 parts Oil agent B (product of the invention) Stearyl alcohol (EO) ₄ stearate 60 parts hydrogenated castor oil (EO) ₂₅ 30 parts oleyl sarcosinate K salt 10 parts Oil C (inventive product) Glycerin (EO) ₃ Tristearate 30 Lauryl alcohol (EO) ₂ Stearate 20 Trimethylolpropane (EO) ₂₄ Distearate
30 Stearoyl sarcosinate K salt 20 Oil agent D (inventive product) Sorbitol (EO) ₁₅ Tristearate 35 Sorbitol (EO) ₂₅ Tristearate 30 Lauryl alcohol (EO) ₂ stearate 20 Lauroyl sarcosinate K salt 15 Oil agent E ( Products of the present invention) Lauryl alcohol phosphate ester K salt 40 Glycerin (EO) ₅ Tristearate 35 Pentaerythritol (EO) ₂₈ Distearate 15 Oleoyl sarcosinate K salt 10 Oil agent F (comparative example) Cetyl alcohol phosphate ester K salt 80 PEG-300 monolaurate 20 Oil agent G (comparative example) Lauryl alcohol phosphate ester K salt 70 2 ethylhexyl stearate 15 Higher alcohol (EO) ₇ 15 Oil agent H (comparative example) PEG-600 dilaurate 100 parts oil agent I (comparative example) ) Oleoyl sarcosinate K salt 100 parts

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[Table] The results show that the conventional oils F and G have poor antistatic properties and roller winding at low humidity, and are also poor in sliver convergence. Oils H and I are comparative examples in which the components used in the product of the present invention were used alone, and Oil H does not have antistatic ability. Oil I has high hygroscopicity and tends to roll up when the humidity is high. In comparison, it is clear that the oils A to E, which are products of the present invention, have excellent performance such as excellent antistatic properties and sliver convergence properties under low humidity conditions, and little roller wrapping even under high humidity conditions.

Claims (1)

[Claims] 1 N-acyl sarcosinate (A) and general formula [In the formula, R ₁ is a polyhydric alcohol residue or a carboxylic acid residue, A is an alkylene group, and R ₂ is an acyl group, or an alkyl group, an alkenyl group, a cycloalkyl group, an alkylaryl group, an aryl group, or an aralkyl group. , (However, if R ₁ is a polyhydric alcohol residue, it is an acyl group); R ₃ is H, an acyl group, or an alkyl group, an alkenyl group, a cycloalkyl group,
Alkylaryl group, aryl group or aralkyl group; n and m are integers of 0 or 1 or more (however, if R ₁ is a carboxylic acid residue and R ₂ or/and R ₃ is an acyl group, n and/or m are 0 p is an integer of 1 or more (however, if R ₁ is a polyhydric alcohol residue, an integer of 2 or more); q
represents an integer of 0 or 1 or more.] An oxyalkylene derivative ester (B) represented by the following: A treating oil for synthetic fibers. 2 (A) is 1 to 30 based on the weight of all treated oils.
% by weight of the synthetic fiber treatment oil agent according to claim 1. 3. The treated oil agent for synthetic fibers according to claim 1 or 2, wherein 10 to 90% by weight of (B) is added based on the weight of the entire treated oil agent. 4 N-acyl sarcosinate (A) and general formula [In the formula, R ₁ is a polyhydric alcohol residue or a carboxylic acid residue; A is an alkylene group; R ₂ is an acyl group, or an alkyl group, an alkenyl group, a cycloalkyl group, an alkylaryl group, an aryl group, or an aralkyl group ( However, if R ₁ is a polyhydric alcohol residue, it is an acyl group); R ₃ is H, an acyl group, or an alkyl group, an alkenyl group, a cycloalkyl group, an alkylaryl group, an aryl group, or an aralkyl group; n and m are 0 or an integer greater than or equal to 1 (however,
If R ₁ is a carboxylic acid residue and R ₂ or/and R ₃ is an acyl group, n and/or m are not 0)
, at least one of p of n and q of m
p is an integer of 1 or more (however, if R is a polyhydric alcohol residue, it is an integer of 2 or more); q represents 0 or an integer of 1 or more. ] A processing oil agent for synthetic fibers, characterized in that it contains an oxyalkylene derivative ester (B) represented by the following and a phosphate ester-based anionic surfactant (C). 5. The synthetic fiber treatment oil agent according to claim 4, wherein 1 to 30% by weight of (A) is added based on the weight of the entire treated oil agent. 6. The treated oil agent for synthetic fibers according to claim 4 or 5, wherein 10 to 90% by weight of (B) is added based on the weight of the entire treated oil agent. 7 (C) is added in an amount of 10 to 89% by weight based on the weight of the entire treated oil agent.