Title of Invention	A COMPOSITION FOR IMPARTING SPIN FINISH TO SYNTHETIC FIBERS AND A PROCESS FOR PRODUCING SYNTHETIC FIBERS WITH SPIN FINISH
Abstract	ABSTRACT 1517/MAS/96 "A composition for imparting spin finish to synthetic fibers and a process for producing synthetic fibers with spin finish This invention relates to a composition for imparting spin finish to synthetic fibers. In addition to conventional components such as lubricants, the composition of this invention contains from 0.1 to 2% by weight of a quaternary ammonium salt of an organic carboxylic acid represented by the general formula wherein Ri to R4 each represent an alkyl or alkenyl group having 1 to 8 carbon atoms and X is an anion of an organic carboxylic acid. The invention also provides a process for producing synthetic fibers with spin finish

Title of Invention

A COMPOSITION FOR IMPARTING SPIN FINISH TO SYNTHETIC FIBERS AND A PROCESS FOR PRODUCING SYNTHETIC FIBERS WITH SPIN FINISH

Abstract

ABSTRACT 1517/MAS/96 "A composition for imparting spin finish to synthetic fibers and a process for producing synthetic fibers with spin finish This invention relates to a composition for imparting spin finish to synthetic fibers. In addition to conventional components such as lubricants, the composition of this invention contains from 0.1 to 2% by weight of a quaternary ammonium salt of an organic carboxylic acid represented by the general formula wherein Ri to R4 each represent an alkyl or alkenyl group having 1 to 8 carbon atoms and X is an anion of an organic carboxylic acid. The invention also provides a process for producing synthetic fibers with spin finish

Full Text	The present invention relates to a composition for imparting spin finish to synthetic fibers and a process for producing synthetic fibers with spin finish. More precisely, it relates to a spin finish to be applied to multi-filaments yam of thermoplastic, synthetic fibers in the step of melt-spinning them, and also to multi¬filaments yam as treated with the spin finish. Description of the Prior Art It has heretofore been known to apply an aqueous emulsion of a spin finish for synthetic fibers to multi-filaments of thermoplastic, synthetic fibers in the step of melt-spinning them, and the spin finish comprises a mixture composed of a surfactant, a lubricant, etc. The surfactant may be either ionic or nonionic. Ionic surfactants are used essentially for the purpose of preventing static electrification of synthetic fibers. After having adhered to synthetic fibers, an ionic surfactant often peels off, during the step of forming yams and the step of processing the yams, to give scum in the yam guides, or it often peels off during the step of heat- treating the yarns to also give carbides such as tar, etc. in the yarn guides. For these reasons, the use of ionic surfactants are problematic in that the cycle for cleaning the yam guides shall be shortened. In order to solve this problem, a spin finish comprising a salt of mono-olefinic dicarboxylic acid or a salt of its derivative has been proposed (see Japanese Patent KOKOKU Nos. 25666/1982 and 14469/1982). Using this, the amount of the substance to be peeled from the yams being formed or processed is reduced. On the other hand, various substances are used as the lubricant constituting the spin finish. For example, for use in the step of forming or processing yarns that is accompanied by heat-treatment at high temperatures, such as in producing draw textured yarns (hereinafter referred to as DTY) from partially oriented yarns (hereinafter referred to as POY) of polyester, the spin finish comprises, as the base component, a polyether-type lubricant in order to minimize as much as possible the formation of carbides such as tar, etc. on a hot plate, etc. However, it is impossible to satisfactorily prevent the formation of such carbides when the spin finish is used. Recently, therefore, it has been proposed to add a silicone compound or a fluoride compound to the spin finish for DTY that shall be sxobjected to heat-treatment at high temperature in order to prevent the accumulation of carbides in the devices used (see Japanese Patent KOKOKU No. 21380/1994, etc.). However, the conventional spin finish that have heretofore been proposed are still unsatisfactory when used in the recent high-speed yarn forming and processing. (For example, in the recent DTY processing, the rate of the yams to be processed is often above 800 or even 1000 m/min.) In high-speed DTY processing with a radiation heater which has been put to practical use in these days, the temperature of the heater is 400'C or higher and the pyrolysate scum firmly adheres to the guides in the heater. For the system of such high-speed DTY processing, even the spin finish containing such a silicone compound or fluoride compound is unsatisfactory. In addition, an aqueous emulsion of such spin finish is peculiarly problematic in the following point. That is, bacteria, fungi, yeasts, etc. easily propagate in the emulsion. Therefore, the emulsion is rotted by them to give a gel-like substance, which is accumulated in the yam giiides to often form scum. In order to solve this problem, a large amount of an antiseptic has heretofore been added to the emulsion, which, however, causes another problem in that it results in the increase of the cost of the emulsion and worsens the working environment where the emulsion is used. SUMMARY-QE-T-aE-J&NVB^K€N We, the present inventors, having noted that the carbides such as tar, etc. as well as scum are essentially derived from the antistatic component (for preventing static electrification) to be in the spin finish for synthetic fibers, have assiduously studied and, as a result, have found that if a small amount of a particular compound is added to the spin finish as an antistatic component and when synthetic fibers are treated with the spin finish, it is possible to drastically reduce the formation of carbides such as tar, etc. and also scum, and that the particular compound as added to the spin finish also acts to prevent an aqueous emulsion of the spin finish from being rotted. On the basis of these findings, we have completed the present invention. The object of the present invention is to reduce the formation of carbides such as tar, etc. as well as scum during high-speed spinning, drawing and processing and also during high-temperature spinning, drawing and processing which is accompanied by heat-treatment at high temperatures, such as DTY processing or the like, thereby prolonging the cycle of cleaning the yarn guides while noticeably reducing the amount of the antiseptic to be added to an aqueous emulsion of a spin finish for synthetic fibers with reducing the cost for spinning, drawing and processing yarns of synthetic fibers and improving the working environment for spinning, drawing and processing them. The above-mentioned object and other objects of the present invention will be clarified further more in the following description, and these objects are attained by the present invention comprising the constitution mentioned below. Specifically, the present invention provides a spin finish for synthetic fibers, which comprises a quaternary ammonium salt of an organic carboxylic acid as an antistatic component (for preventing static electrification). The present invention also provides synthetic fibers as treated with the spin finish. The quaternary ammonium salt of an organic carboxylic acid for use in the present invention may be represented by a general forroula (1): R R, — N — R4 X- • • • ( 1) Ra wherein Ri to R4 each represent an alkyl or alkenyl group having from 1 to 12 carbon atoms; and X- represents an anion of an organic carboxylic acid. The gxiatemary ammonium salt of an organic carboxylic acid may be a reaction product to be obtained through the reaction of a reaction product, which results from the reaction of a tertiary amine and a dialkyl carbonate, and an organic carboxylic acid. The spin finish of the present invention may contain a polyether-type lubricant. BESMiSS:) I^SQ^EP^'IQN Of^^^ffi ^SfM^RH) EI>@QDIMEtJTS The spin finish for synthetic fibers of the present invention comprises, as an antistatic component (for preventing static electrification), a quaternary aittnonium salt of an organic carboxylic acid. Where the spin finish is used for forming and processing yarns of synthetic fibers, which is accompanied by heat-treatment of the yams at high temperatures, such as processing of DTY, it is preferable that the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish is a compound of a general formula (1): R R, — N — R« X- •••(!) wherein Ri to R4 each represent an alkyl or alkenyl group having from 1 to 12 carbon atoms, preferably an alkyl or alkenyl group having from 1 to 5 carbon atoms; and X-represents an anion of an organic carboxylic acid. The amount of the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish of the present invention is generally from 0.1 to 5.0 % by weight, preferably from 0.2 to 2.0 % by weight, relative to the total weight of the spin finish. If the salt content is less than 0.1 % by weight, the antistatic capacity of the spin finish tends to lower. If, however, it is more than 5.0 % by weight, the amount of scum or tar to be formed tends to increase or the degree of oil dropping in the step of processing DTY tends to increase. The organic carboxylic acid that constitutes the quaternary ammonium salt of the acid for use in the present invention includes aliphatic monocarboxylic acids (e.g., formic acid, acetic acid, propionic acid, caproic acid, caprylic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, 2-ethylhexanoic acid, isostearic acid, acrylic acid, methacrylic acid, oleic acid, erucic acid, cyclohexane-carboxylic acid, glycolic acid, lactic acid, laurylthiopropionic acid, etc.), aliphatic dicarboxylic acids (e.g., oxalic acid, raalonic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, undecanoic diacid, dodecanoic diacid, maleic acid, thiodipropionic acid, etc.), aromatic monocarboxylic acids (e.g., benzoic acid, toluic acid, ethyl-benzoic acid, etc.), and aromatic dicarboxylic acids (e.g., phthalic acid, isophthalic acid, terephthalic acid, etc.). Of these, preferred are aliphatic monocarboxylic acids, aliphatic dicarboxylic acids and aromatic dicarboxylic acids. Especially preferred are 2-ethylhexanoic acid, maleic acid and phthalic acid. One or more of the above-mentioned organic carboxylic acids can be used singly or as combined. The quaternary ammonium residue that constitutes the quaternary ammonium salt of an organic carboxylic acid for use in the present invention as well as the quaternary ammonium cation that constitutes the compound of formula (1) also for use in the present invention is derived from a quaternated derivative of a tertiary amine having alkyl or alkenyl groups with from 1 to 5 carbon atoms. The tertiary amine includes aliphatic amines (e.g., trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-octylamine, octyldimethylamine, lauryldimethylamine, stearyldimethylamine, etc.), cind alicyclic amines (e.g., N-methylpyrrolidine, N-ethylpyrrolidine, N-methylpiperidine, N-ethylpiperidine, N-methylhexamethyleneimine, N- ethylhexamethyleneimine, N-methyImorpholine, N-butyImorpholine, N,N'-dimethylpiperazine, N,N'-diethylpiperazine, l,5-dia2abicyclo[4,3,0]-5-nonene, 1,8-diazabicyclo[5,4,0]-undecene, etc.). Of these, preferred are aliphatic amines. Especially preferred are trimethylamine, triethylamine and octyldimethylamine. Qioatemary ammonium salts of organic carboxylic acids and compounds of formula (1) for use in the present invention can be obtained by reacting a reaction product, which is obtained through the reaction of a tertiary amine with a dialkyl carbonate, with an organic carboxylic acid, for example, in the manner as mentioned below. Quaternary ammonium salts of organic carboxylic acids for use in the present invention can be produced, for example, according to the following method. To produce trimethyloctylammonium 2-ethylhexanoate, one mol of octyldimethylainine is fed into an autoclave along with one mol or more of dimethyl carbonate and methanol and these are reacted under pressure of about 5 kg/cm^ at about 120'C to obtain a methanol solution of trimethyloctylammonium methyl carbonate. Next, the methanol solution of trimethyloctylammonium methyl carbonate is gradually added to 2-ethylhexanoic acid at from 80 to 901C , while carbon dioxide being generated and methanol are removed through distillation. Next, water is added to the reaction systan. which is thus subjected to complete anion-exchange reaction. After having adjusted its concentration, the system gives trimethyloctylammonium 2-ethylhexanoate. Compounds of formula (1) can be produced, for example, according to the following method. To produce triethylmethylammonium maleate, one mol of triethylamine is fed into an autoclave along with one mol or more of dimethyl carbonate and methanol and these are reacted under pressure of about 5 kg/cm2 at about 1200 to obtain a methanol solution of triethylmethylammonium methyl carbonate. Next, a methanol solution of maleic acid is gradually added to the methanol solution at from 80 to 90 C , while carbon dioxide being generated and methanol are removed through distillation. Next, water is added to the reaction system, which is thus subjected to complete anion-exchange reaction. After having adjusted its concentration, the system gives triethylmethylammonium maleate. The spin finish of the present invention may optionally contain a lubricant (e.g., mineral oils, esters of fatty acids, polyethers, silicone oils, etc.). In particular, where the spin finish comprises, as the quaternary ammonium salt of an organic carboxylic acid, a compound of formula (1) in order that the agent is used in a step of forming and processing synthetic fibers which is accompanied by heat-treatment of the fibers at high temperatures, for example, in ETY processing or the like, it is desirable that the spin finish contains a polyether-type lubricant. The polyether-type lubricant includes compounds to be prepared by addition (co)polymerization of an alkylene oxide having from 2 to 4 carbon atoms with an alcohol having one or more hydroxyl groups in the molecule (hereinafter referred to as adducts), and compounds to be derived from the adducts by blocking the terminal hydroxyl group.thereof with an alkyl group. The terminology " addition (co)polymerization" as referred to herein indicates "addition copolyraerization" or "addition polymerization", and its mode may be any of random addition and block addition. To block the terminal hydroxyl group of the adduct with an alkyl group, employable is any of alkoxylation and acylation. It is preferable that the polyether-type lubricant for use in the present invention has a number average molecular weight of from 1000 to 20,000. The polyether-type lubricant content of the spin finish is preferably from 70 to 99.5 % by weight relative to the total weight of the spin finish. The alcohol that constitutes the adduct includes any desired, natural and synthetic monoalcohols (e.g., methanol, ethanol, isopropanol, butanol, isoamyl alcohol, 2-ethylhexanol, lauryl alcohol, isotridecyl alcohol, isocetyl alcohol, stearyl alcohol, isostearyl alcohol, etc.). dialcohols (e.g., ethylene glycol, propylene glycol, neopentyl glycol, hexylene glycol, etc.) and trialcohols and higher polyalcohols (e.g., glycerin, trimethylolpropane, pentaerythritol, sorbitan, sorbitol, etc.). The alkylene oxide with from 2 to 4 carbon atoms that constitutes the adduct includes ethylene oxide (hereinafter referred to as "EO"), 1,2-propylene oxide (hereinafter referred to as "PO"), 1,2-butylene oxide, tetrahydrofuran, etc. It is preferable that the adduct consists essentially of EO. Where EO is copolyroerized with other alkylene oxide(s), it is desirable that the proportion of BO is from 5 to 80 % by weight. As specific examples of the polyether-type lubricant usable in the present invention, mentioned are butanol-(EO/PO) random adduct (EO/PO = 50/50 % by weight, mean molecular weight = 1,400), hexylene glycol-(EO/PO) random adduct (EO/PO = 40/60 % by weight, mean molecular weight = 4,000), and methyl ether of trimethylolpropane-(EO)(PO) block adduct (EO/PO = 20/80 % by weight, mean molecular weight = 5,000). The spin finish of the present invention may contain any other optional components, insofar as the components added do not make the spin finish containing them overstep the spirit and scope of the present invention. Such optional components include emulsifiers (e.g., polyalcohol ester-type nonionic surfactants, polyethylene glycol-type nonionic surfactants, amide-type nonionic surfactants, etc.), antistatic agents (e.g., soap, sulfate-type anionic surfactants, sulfonate-type anionic surfactants, phosphate-type anionic surfactants, betairl-type ampholytic surfactants, etc.), oilness-improving agents (e.g., higher fatty acids, higher aliphatic amines), extreme pressure additives, rust inhibitors, antioxidants and other functional additives, and their compounds not specifically defined. The spin finish of the present invention is applied, as its aqueous emulsion, to filaments being spun during the step of melt-spinning synthetic fibers. The concentration of the emulsion may be freely selected within a range between 0.5 % by weight and 30 % by weight. Preferably, however, it is from 5 to 20 % by weight. The means of applying the emulsion to the filaments is not specifically defined. Employable is any of nozzle oiling and roller oiling. The amount of the spin finish of the present invention to be adhered to synthetic fibers is generally from 0.1 to 2.0 % by weight, preferably from 0.2 to 1.5 % by weight, in terms of the net weight thereof relative to the weight of the synthetic fibers. Synthetic fibers to be treated with the spin finish of the present invention include, for example, multi-filaments of thermoplastic synthetic fibers of polyesters, nylons, polypropylenes, etc. the kinds of the yams made of such synthetic fibers are not specifically defined. The present invention can be applied to various yams that widely include from small denier yams for clothing to large denier yams for industrial materials. One can understand the present invention more clearly, referring to the following examples which embody the present invention and to the following comparative examples which are to be compared with the present invention. These examples and comparative examples are to explain the present invention but are not to restrict the scope of the present invention. Accordingly, the present invention provides a composition for imparting spin finish to synthetic fibers, characterized in that the said composition contains from 0.1 to 2.0% by weight of a quaternary ammonium salt of an organic carboxylic acid represented by general formula (1): h Ri-N—R. X- ... (1) I R3 wherein R] to R4 each represent an alkyl or alkenyl group having from 1 to 8 carbon atoms; and X represents an anion of an organic carboxylic acid. Accordingly, the present invention also provides a process for producing synthetic fibers with spin finish comprising the step of treating said yam with the composition for imparting spin finish as claimed in claims 1 to 8 preferably at the melt spinning stage. In the following examples and comparative examples, parts and % are by weight. Examples 1 to 4, Comparative Examples 1 to 4: The following compounds (A) to (C) were selected as examples of the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish of the present invention. The compound and a conventional antistatic agent were added to a base oil to prepare spin finish samples for synthetic fibers of Examples 1 to 4 and Comparative Examples 1 to 4 as shown in Table 1 below. In Table 1, the amounts of the constitutive components are represented by "% by weight". Composition of Base Oil: Isotridecyl stearate 60 parts Glycerin monooleate 10 parts Oleyl alcohol-5E0 adduct 12 parts Hydrogenated castor oil-15BO adduct 15 parts Laurie acid diethanolamide 2 parts Quaternary ammonium salt of organic carboxylic acid of the invention: Compound A: Triethylmethylammonium phthalate Compound B: Tetramethylammonium maleate Compound C: Octyltriraethylamraonium 2-ethylhexanoate Conventional antistatic agent: Compound D: Sodium paraffin (C14-16) sulfonate (WAROLAT U, produced by Bayer Co.) Compound E: Sodium diisooctylsulfosuccinate Compound F: Potassium pentadecenylsuccinate Compound G: Ammoniiam laurate Table 1 Number of Spin Finish Sample Example Comparative Example 1 2 3 4 1 2 3 4 Base Oil 95 95 95 95 95 95 95 95 Compound A 0.5 Compound B 1.0 Compound C 1.0 2.0 Compound D 1.0 1.0 1.0 1.0 3.0 1.0 1.0 1.0 Compound E 2.0 Compound F 2.0 Compound G 2.0 Next, yarns as prepared by deoiling (washing) commercially-available polyester filaments (75 deniers/36 filaments) were treated with any one of the spin finish samples of Examples 1 to 4 and Comparative Examples 1 to 4, the net weight of the spin finish adhered being 0.8 %, and then dried. The thus-treated yarn samples were tested, according to the test methods mentioned below, to measure the amount of static charges generated after the test, the amount of scum formed after the test and the amount of tar formed after the test. The results are shown in Table 2 below. Test Methods: Amount of static charges generated: The yarn sample was run at a speed of 300 m/min under an original tension of 10 g, while being wound around an alumina ceramic pin, and the amount of static charges generated on the sample was measured using a potentiometer. Amount of scvsm formed and dropped: The yarn sample was rxm at a speed of 300 m/min under an original tension of 10 g, while being kept in contact with reed blades. After one hour, the amount of the substance as adhered to the reed blades and the amount of the substance as dropped down below the reed blades were measured with the naked eye. In the column for "Amount of Scum Dropped" in Table 2, "00" indicates that "no scum dropped", "O" indicates that "a little scum dropped", "A" indicates that "some scum dropped", and "X" indicates that " much scum dropped". Amount of tar formed: The yarn sample was run at a speed of 300 m/min under an original tension of 10 g, while being wound around a hot roller having a surface temperature of 200'C . After one hour, the amount of tar formed was measured with the naked eye. In the column for "Amount of Tar Formed" in Table 2, " 00" indicates that "no tar formed", "0" indicates that "a little tar formed", "A" indicates that "some tar formed", and "X" indicates that "much tar formed". Table 2 ^■r Test Results JNumDer \JI. Spin Finish Sample Amount of Staic Charges Generated (V) Amount of Scum Dropped Amount of Tar Formed Example 1 (-) 40 0 or 00 0 2 (-) 50 0 0 3 (-) 60 0 0 4 ( + ) 20 0 0 Comp. Example 1 ( - ) 320 X X 2 ( - ) 260 0 A 3 ( - ) 330 X X 4 ( - ) 440 A or X X From Table 2 above, it is understood that the spin finish samples of the present invention all have much better antistatic capacity than the conventional spin finish samples. Next, using ion-exchanged water, aqueous 10-% emulsions each comprising any one of the spin finish samples of Examples 1 to 4 and Comparative Examples 1 to 4 were prepared. The emulsions were sealed in an incubator at 37 X; for 72 hours. After that, the nximber of the total microbes, X (cells/cc) in each emulsion was measured using " San-ai Bio Checker TTC" (produced by San-ai Petroleum Co.) and represented in terms of the common logarithmic nxomber (log X). The results are shown in Table 3 below. Table 3 Number of Spin Finish Sample Test Result (log X) Example 1 0 2 0 3 1 4 0 Comparative Example 1 4 or 5 2 4 or 5 3 4 or 5 4 6 or 7 From Table 3 above, it is obvious that the spin finish samples of the present invention are effective in inhibiting the growth of bacteria, etc. Examples 5 to 12, Comparative Examples 5 to 12: The following compounds (H) to (J) were selected as examples of the compound of formula (1) to be in the spin finish of the present invention. The compound or a conventional antistatic agent (K, L or D mentioned below) was added to a base oil comprising a polyether-type lubricant to prepare spin finish samples for synthetic fibers of Examples 5 to 12 and Comparative Examples 5 to 12 as shown in the following Tables 4 and 5, respectively. The amount of static charges generated around polyester yams as treated with any of these samples, and the amount of the residue as remained after heat-treatment of each sample (this indicates the heat resistance of each sample) were measured according to the methods mentioned below. The test results are shown in Tables 4 and 5. Composition of Base Oil: Butanol-(EO/P0) random adduct (EO/PO = 50/50, mean molecular weight = 1,400) 60 parts Lauryl alcohol-(PO)(EO) block adduct (BO/PO = 40/60, mean molecular weight = 1,400) 20 parts Propylene glycol-(BO/PO) random adduct (BO/PO = 50/50, mean molecular weight = 2,000) 10 parts 2-Ethylhexyl palmitate 10 parts Compound of formula (1) of the invention: Compound H: Methyltriethylammonium phthalate Compound I: Methyltriethylartmoniijm maleate Compound J: Tetramethylainoaonium 2-ethYlhexanoate Conventional antistatic agent: Compound K: Potassium phosphate ester of lauryl alcohol-3B0 adduct Compound L: Potassium phosphate ester of isostearyl alcohol-5B0 adduct Compound D: Mentioned above Test Methods: Amount of static charges generated: Yams as prepared by deoiling (washing) commercially-available polyester filaments (75 deniers/36 filaments) were treated with any one of the spin finish samples of Examples 5 to 12 and Comparative Examples 5 to 12, the net weight of the spin finish sample adhered being 0.3 %, and then dried. The thus-treated yarn samples were run at a speed of 100 m/min or 300 m/min in an atmosphere having a temperature of 20*C and a relative humidity of 40 %, while being wound around a mat-finished chromium pin, an alumina ceramic pin or an urethane disc, and the amount of static charges generated on each sample was measured using a current-collecting potentiometer. Amount of residue remained after heat-treatment: 0.5 g of each of the spin finish samples of Examples 5 to 12 and Comparative Examples 5 to 12 was put onto a stainless steel dish having a diameter of 50 mm and a height of 10 mm, and heated in an air-circulating drier at 220'C for 8 hours. The amount of the residue remained on each dish was measured. Next, each dish was further heated in an electric furnace at 400'C for 20 minutes, and the amount of the residue still remained thereon was measured. Table 4 Number of Spin Finish Sample Example 5 6 7 8 9 10 11 12 Base Oil 99.7 99.7 99.7 99.5 99.0 99.7 99.5 99.0 Compound H 0.3 0.5 Compound I 0.3 0.5 1.0 Compound J 0.3 0.5 1.0 Amount of Staic Charges Generated (V) Around mat-finished chromium pm 100 m/min -50 -30 -10 -50 -20 -10 -40 -20 300 m/min -60 -40 -20 -60 -40 -20 -50 -40 Around alumina ceramic pm 100 m/min -120 -100 -80 -100 -50 -40 -90 -60 300 m/min -150 -120 -90 -120 -90 -60 -120 -100 Around urethane disc 100 m/min -100 -80 -60 -100 -40 -30 -100 -90 300 m/min -120 -100 -80 -120 -80 -70 -140 -100 Percentage of Residue after Heat -Treatment (%) 2201 , 8 hr 4001 , 20 min 0.1 0 0.1 0 0.1 0 0.1 0 0.1 0 0.15 0.05 0.1 0 0.2 0.05 Table 5 Number of Spin Finish Sample Comparative Example 5 6 7 8 9 10 11 12 Base Oil 99.7 99.0 99.7 99.5 99.0 99.7 99.5 99.0 Compound K 0.3 1.0 Compound L 0.3 0.5 1.0 Compound D 0.3 0.5 1.0 Amount of Staic Charges Generated (V) Around mat-finished chromium pin 100 m/min -480 -180 -450 -300 -230 -510 -390 -220 300 m/min -580 -250 -550 -380 -280 -590 -480 -280 Around alumina ceramic pm 100 m/min -720 -450 -520 -360 -280 -920 -720 -530 300 m/min -860 -550 -680 -530 -400 -980 -860 -630 Around ur ethane disc 100 m/min -320 -280 -420 -330 -220 -450 -390 -280 300 m/min -480 -360 -520 -460 -370 -520 -420 -360 Percentage of Residue after Heat -Treatment (%) 220r , 8 hr 400 r , 20 rain 0.7 0.2 1.1 0.7 0.5 0.2 1,2 0.4 1.4 0.8 0.5 0.2 0.9 0.4 1.2 0.7 From Tables 4 and 5, it is understood that the spin finish samples of the present invention each comprising a compound of formula (1) have higher antistatic capacity than the conventional spin finish samples and that the former have higher heat resistance than the latter as producing smaller amounts of tar and scum at high temperatures. Next, a polyester was melt-spun at a winding-up speed of 3400 m/min to produce POY of 115 deniers/36 filaments, while applying to POY an aqueous 10-% emulsion of the spin finish of Example 5 or Comparative Example 5, through a nozzle, the net amount of the spin finish adhered to POY being 0.3 %. The POY sample was then processed into DTY continuously for one month, at a processing speed of 1200 m/min and at a heater temperature of 450'C / using a false twisting machine (HTS-1500 Model, produced by Teijin Machine Co.). The number of fluffs as formed around the thus-processed DTY was measured and the condition of the soiling, if any, of the guides in the heater was checked, according to the methods mentioned below. The results are shown in Table 6 below. Test Methods: Number of Fluffs: One month after the start of the processing test, the yarn thus processed were rewinded at a speed of 150 m/min, while measuring the number of the fluffs as formed per 10000m of the yarn using a fluff tester (DT-140 Model, produced by Toray Co.). Degree of Soiling of Guides: One month after the start of the processing test, the condition of the soiling, if any, of the guides in the heater was observed with the naked eye. Table 6 Number of Spin Finish Test Results Number of Fluffs Formed Around Processed Yam Soiling of Guides in Heater Example 5 5 Almost not soiled. Comparative Example 5 62 Thermal decomposates of spin finish adhered to the guides. From Table 6 above, it is understood that the spin finish of the present invention comprising a compound of formula (1) can exhibit extremely excellent capacity in high-speed DTY processing to be conducted in a radiation heater or the like at high temperatures, as ccxnpared with the conventional spin finish. WE CLAIM: 1. A composition for imparting spin finish to synthetic fibers, characterized in that the said composition contains from 0.1 to 2 0% by weight of a quaternary ammonium salt of an organic carboxylic acid represented by general formula (1): wherein R1 to R4 each represent an alkyl or alkenyl group having from 1 to 8 carbon atoms; and X represents an anion of an organic carboxylic acid. 2. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, wherein said quaternary ammonium salt of an organic carboxylic acid is prepared by reacting a tertiary amine with a dialkyl carbonate followed by treating the reaction product with an organic carboxylic acid. 3. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, wherein the organic carboxylic acid is a monocarboxylic acid or a dicarboxylic acid. 4. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, wherein said organic carboxylic acid is selected from maleic acid, ophthalmic acid and 2-ethylhexanoic acid or a mixture thereof. 5. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, which contains a polyether-type lubricant. 6. The composition for imparting spin finish to synthetic fibers as claimed in claim 5, wherein polyether-type lubricant content is from 70 to 99.5% by weight. 7. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, wherein R1 to R4 in formula (1) each are an alkyl or alkenyl group having from 1 to 5 carbon atoms. 8. The composition for imparting spin finish to synthetic fibers as claimed in claim 1, wherein the quaternary ammonium salt is an octyltrimethylammonium salt. 9. A process for producing synthetic fibers with spin finish comprising the step of treating said yam with the composition for imparting spin finish as claimed in claims 1 to 8 preferably at the melt spinning stage. 10. A composition for imparting spin finish to synthetic fibers substantially as herein described. 11. A process for producing synthetic fibers with spin finish substantially as herein described.

Full Text

The present invention relates to a composition for imparting spin finish to synthetic fibers and a process for producing synthetic fibers with spin finish. More precisely, it relates to a spin finish to be applied to multi-filaments yam of thermoplastic, synthetic fibers in the step of melt-spinning them, and also to multi¬filaments yam as treated with the spin finish.
Description of the Prior Art
It has heretofore been known to apply an aqueous emulsion of a spin finish for synthetic fibers to multi-filaments of thermoplastic, synthetic fibers in the step of melt-spinning them, and the spin finish comprises a mixture composed of a surfactant, a lubricant, etc.
The surfactant may be either ionic or nonionic. Ionic surfactants are used essentially for the purpose of preventing static electrification of synthetic fibers. After having adhered to synthetic fibers, an ionic surfactant often peels off, during the step of forming yams and the step of processing the yams, to give scum in the yam guides, or it often peels off during the step of heat-

treating the yarns to also give carbides such as tar, etc. in the yarn guides. For these reasons, the use of ionic surfactants are problematic in that the cycle for cleaning the yam guides shall be shortened. In order to solve this problem, a spin finish comprising a salt of mono-olefinic dicarboxylic acid or a salt of its derivative has been proposed (see Japanese Patent KOKOKU Nos. 25666/1982 and 14469/1982). Using this, the amount of the substance to be peeled from the yams being formed or processed is reduced. On the other hand, various substances are used as the lubricant constituting the spin finish. For example, for use in the step of forming or processing yarns that is accompanied by heat-treatment at high temperatures, such as in producing draw textured yarns (hereinafter referred to as DTY) from partially oriented yarns (hereinafter referred to as POY) of polyester, the spin finish comprises, as the base component, a polyether-type lubricant in order to minimize as much as possible the formation of carbides such as tar, etc. on a hot plate, etc. However, it is impossible to satisfactorily prevent the formation of such carbides when the spin finish is used. Recently, therefore, it has been proposed to add a silicone compound or a fluoride compound to the spin finish for DTY that shall be sxobjected to heat-treatment at high temperature in order to prevent the accumulation of carbides in the devices used

(see Japanese Patent KOKOKU No. 21380/1994, etc.).
However, the conventional spin finish that have heretofore been proposed are still unsatisfactory when used in the recent high-speed yarn forming and processing. (For example, in the recent DTY processing, the rate of the yams to be processed is often above 800 or even 1000 m/min.) In high-speed DTY processing with a radiation heater which has been put to practical use in these days, the temperature of the heater is 400'C or higher and the pyrolysate scum firmly adheres to the guides in the heater. For the system of such high-speed DTY processing, even the spin finish containing such a silicone compound or fluoride compound is unsatisfactory.
In addition, an aqueous emulsion of such spin finish is peculiarly problematic in the following point. That is, bacteria, fungi, yeasts, etc. easily propagate in the emulsion. Therefore, the emulsion is rotted by them to give a gel-like substance, which is accumulated in the yam giiides to often form scum. In order to solve this problem, a large amount of an antiseptic has heretofore been added to the emulsion, which, however, causes another problem in that it results in the increase of the cost of the emulsion and worsens the working environment where the emulsion is used.

SUMMARY-QE-T-aE-J&NVB^K€N
We, the present inventors, having noted that the carbides such as tar, etc. as well as scum are essentially derived from the antistatic component (for preventing static electrification) to be in the spin finish for synthetic fibers, have assiduously studied and, as a result, have found that if a small amount of a particular compound is added to the spin finish as an antistatic component and when synthetic fibers are treated with the spin finish, it is possible to drastically reduce the formation of carbides such as tar, etc. and also scum, and that the particular compound as added to the spin finish also acts to prevent an aqueous emulsion of the spin finish from being rotted. On the basis of these findings, we have completed the present invention.
The object of the present invention is to reduce the formation of carbides such as tar, etc. as well as scum during high-speed spinning, drawing and processing and also during high-temperature spinning, drawing and processing which is accompanied by heat-treatment at high temperatures, such as DTY processing or the like, thereby prolonging the cycle of cleaning the yarn guides while noticeably reducing the amount of the antiseptic to be added to an aqueous emulsion of a spin finish for synthetic fibers with reducing the cost for spinning, drawing and

processing yarns of synthetic fibers and improving the working environment for spinning, drawing and processing them.
The above-mentioned object and other objects of the present invention will be clarified further more in the following description, and these objects are attained by the present invention comprising the constitution mentioned below.
Specifically, the present invention provides a spin finish for synthetic fibers, which comprises a quaternary ammonium salt of an organic carboxylic acid as an antistatic component (for preventing static electrification). The present invention also provides synthetic fibers as treated with the spin finish.
The quaternary ammonium salt of an organic carboxylic acid for use in the present invention may be represented by a general forroula (1):
R
R, — N — R4 X- • • • ( 1)
Ra
wherein Ri to R4 each represent an alkyl or alkenyl group having from 1 to 12 carbon atoms; and X- represents an

anion of an organic carboxylic acid.
The gxiatemary ammonium salt of an organic carboxylic acid may be a reaction product to be obtained through the reaction of a reaction product, which results from the reaction of a tertiary amine and a dialkyl carbonate, and an organic carboxylic acid.
The spin finish of the present invention may contain a polyether-type lubricant.
BESMiSS:) I^SQ^EP^'IQN Of^^^ffi ^SfM^RH) EI>@QDIMEtJTS The spin finish for synthetic fibers of the present invention comprises, as an antistatic component (for preventing static electrification), a quaternary aittnonium salt of an organic carboxylic acid. Where the spin finish is used for forming and processing yarns of synthetic fibers, which is accompanied by heat-treatment of the yams at high temperatures, such as processing of DTY, it is preferable that the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish is a compound of a general formula (1):
R
R, — N — R« X- •••(!)

wherein Ri to R4 each represent an alkyl or alkenyl group having from 1 to 12 carbon atoms, preferably an alkyl or alkenyl group having from 1 to 5 carbon atoms; and X-represents an anion of an organic carboxylic acid.
The amount of the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish of the present invention is generally from 0.1 to 5.0 % by weight, preferably from 0.2 to 2.0 % by weight, relative to the total weight of the spin finish. If the salt content is less than 0.1 % by weight, the antistatic capacity of the spin finish tends to lower. If, however, it is more than 5.0 % by weight, the amount of scum or tar to be formed tends to increase or the degree of oil dropping in the step of processing DTY tends to increase.
The organic carboxylic acid that constitutes the quaternary ammonium salt of the acid for use in the present invention includes aliphatic monocarboxylic acids (e.g., formic acid, acetic acid, propionic acid, caproic acid, caprylic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, 2-ethylhexanoic acid, isostearic acid, acrylic acid, methacrylic acid, oleic acid, erucic acid, cyclohexane-carboxylic acid, glycolic acid, lactic acid, laurylthiopropionic acid, etc.), aliphatic dicarboxylic

acids (e.g., oxalic acid, raalonic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, undecanoic diacid, dodecanoic diacid, maleic acid, thiodipropionic acid, etc.), aromatic monocarboxylic acids (e.g., benzoic acid, toluic acid, ethyl-benzoic acid, etc.), and aromatic dicarboxylic acids (e.g., phthalic acid, isophthalic acid, terephthalic acid, etc.). Of these, preferred are aliphatic monocarboxylic acids, aliphatic dicarboxylic acids and aromatic dicarboxylic acids. Especially preferred are 2-ethylhexanoic acid, maleic acid and phthalic acid. One or more of the above-mentioned organic carboxylic acids can be used singly or as combined.
The quaternary ammonium residue that constitutes the quaternary ammonium salt of an organic carboxylic acid for use in the present invention as well as the quaternary ammonium cation that constitutes the compound of formula (1) also for use in the present invention is derived from a quaternated derivative of a tertiary amine having alkyl or alkenyl groups with from 1 to 5 carbon atoms. The tertiary amine includes aliphatic amines (e.g., trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-octylamine, octyldimethylamine, lauryldimethylamine, stearyldimethylamine, etc.), cind alicyclic amines (e.g., N-methylpyrrolidine, N-ethylpyrrolidine, N-methylpiperidine, N-ethylpiperidine, N-methylhexamethyleneimine, N-

ethylhexamethyleneimine, N-methyImorpholine, N-butyImorpholine, N,N'-dimethylpiperazine, N,N'-diethylpiperazine, l,5-dia2abicyclo[4,3,0]-5-nonene, 1,8-diazabicyclo[5,4,0]-undecene, etc.). Of these, preferred are aliphatic amines. Especially preferred are trimethylamine, triethylamine and octyldimethylamine.
Qioatemary ammonium salts of organic carboxylic acids and compounds of formula (1) for use in the present invention can be obtained by reacting a reaction product, which is obtained through the reaction of a tertiary amine with a dialkyl carbonate, with an organic carboxylic acid, for example, in the manner as mentioned below.
Quaternary ammonium salts of organic carboxylic acids for use in the present invention can be produced, for example, according to the following method. To produce trimethyloctylammonium 2-ethylhexanoate, one mol of octyldimethylainine is fed into an autoclave along with one mol or more of dimethyl carbonate and methanol and these are reacted under pressure of about 5 kg/cm^ at about 120'C to obtain a methanol solution of trimethyloctylammonium methyl carbonate. Next, the methanol solution of trimethyloctylammonium methyl carbonate is gradually added to 2-ethylhexanoic acid at from 80 to 901C , while carbon dioxide being generated and methanol are removed through distillation. Next, water is added to the reaction systan.

which is thus subjected to complete anion-exchange reaction. After having adjusted its concentration, the system gives trimethyloctylammonium 2-ethylhexanoate.
Compounds of formula (1) can be produced, for example, according to the following method. To produce triethylmethylammonium maleate, one mol of triethylamine is fed into an autoclave along with one mol or more of dimethyl carbonate and methanol and these are reacted under pressure of about 5 kg/cm2 at about 120*0 to obtain a methanol solution of triethylmethylammonium methyl carbonate. Next, a methanol solution of maleic acid is gradually added to the methanol solution at from 80 to 90 *C , while carbon dioxide being generated and methanol are removed through distillation. Next, water is added to the reaction system, which is thus subjected to complete anion-exchange reaction. After having adjusted its concentration, the system gives triethylmethylammonium maleate.
The spin finish of the present invention may optionally contain a lubricant (e.g., mineral oils, esters of fatty acids, polyethers, silicone oils, etc.). In particular, where the spin finish comprises, as the quaternary ammonium salt of an organic carboxylic acid, a compound of formula (1) in order that the agent is used in a step of forming and processing synthetic fibers which is accompanied by heat-treatment of the fibers at high

temperatures, for example, in ETY processing or the like, it is desirable that the spin finish contains a polyether-type lubricant. The polyether-type lubricant includes compounds to be prepared by addition (co)polymerization of an alkylene oxide having from 2 to 4 carbon atoms with an alcohol having one or more hydroxyl groups in the molecule (hereinafter referred to as adducts), and compounds to be derived from the adducts by blocking the terminal hydroxyl group.thereof with an alkyl group. The terminology " addition (co)polymerization" as referred to herein indicates "addition copolyraerization" or "addition polymerization", and its mode may be any of random addition and block addition. To block the terminal hydroxyl group of the adduct with an alkyl group, employable is any of alkoxylation and acylation. It is preferable that the polyether-type lubricant for use in the present invention has a number average molecular weight of from 1000 to 20,000. The polyether-type lubricant content of the spin finish is preferably from 70 to 99.5 % by weight relative to the total weight of the spin finish.
The alcohol that constitutes the adduct includes any desired, natural and synthetic monoalcohols (e.g., methanol, ethanol, isopropanol, butanol, isoamyl alcohol, 2-ethylhexanol, lauryl alcohol, isotridecyl alcohol, isocetyl alcohol, stearyl alcohol, isostearyl alcohol, etc.).

dialcohols (e.g., ethylene glycol, propylene glycol, neopentyl glycol, hexylene glycol, etc.) and trialcohols and higher polyalcohols (e.g., glycerin, trimethylolpropane, pentaerythritol, sorbitan, sorbitol, etc.).
The alkylene oxide with from 2 to 4 carbon atoms that constitutes the adduct includes ethylene oxide (hereinafter referred to as "EO"), 1,2-propylene oxide (hereinafter referred to as "PO"), 1,2-butylene oxide, tetrahydrofuran, etc. It is preferable that the adduct consists essentially of EO. Where EO is copolyroerized with other alkylene oxide(s), it is desirable that the proportion of BO is from 5 to 80 % by weight.
As specific examples of the polyether-type lubricant usable in the present invention, mentioned are butanol-(EO/PO) random adduct (EO/PO = 50/50 % by weight, mean molecular weight = 1,400), hexylene glycol-(EO/PO) random adduct (EO/PO = 40/60 % by weight, mean molecular weight = 4,000), and methyl ether of trimethylolpropane-(EO)(PO) block adduct (EO/PO = 20/80 % by weight, mean molecular weight = 5,000).
The spin finish of the present invention may contain any other optional components, insofar as the components added do not make the spin finish containing them overstep the spirit and scope of the present invention. Such optional components include emulsifiers (e.g., polyalcohol

ester-type nonionic surfactants, polyethylene glycol-type nonionic surfactants, amide-type nonionic surfactants, etc.), antistatic agents (e.g., soap, sulfate-type anionic surfactants, sulfonate-type anionic surfactants, phosphate-type anionic surfactants, betairl-type ampholytic surfactants, etc.), oilness-improving agents (e.g., higher fatty acids, higher aliphatic amines), extreme pressure additives, rust inhibitors, antioxidants and other functional additives, and their compounds not specifically defined.
The spin finish of the present invention is applied, as its aqueous emulsion, to filaments being spun during the step of melt-spinning synthetic fibers. The concentration of the emulsion may be freely selected within a range between 0.5 % by weight and 30 % by weight. Preferably, however, it is from 5 to 20 % by weight. The means of applying the emulsion to the filaments is not specifically defined. Employable is any of nozzle oiling and roller oiling.
The amount of the spin finish of the present invention to be adhered to synthetic fibers is generally from 0.1 to 2.0 % by weight, preferably from 0.2 to 1.5 % by weight, in terms of the net weight thereof relative to the weight of the synthetic fibers.
Synthetic fibers to be treated with the spin finish of

the present invention include, for example, multi-filaments of thermoplastic synthetic fibers of polyesters, nylons, polypropylenes, etc. the kinds of the yams made of such synthetic fibers are not specifically defined. The present invention can be applied to various yams that widely include from small denier yams for clothing to large denier yams for industrial materials.
One can understand the present invention more clearly, referring to the following examples which embody the present invention and to the following comparative examples which are to be compared with the present invention. These examples and comparative examples are to explain the present invention but are not to restrict the scope of the present invention.
Accordingly, the present invention provides a composition for imparting spin finish to synthetic fibers, characterized in that the said composition contains from 0.1 to 2.0% by weight of a quaternary ammonium salt of an organic carboxylic acid represented by general formula (1):
h
Ri-N—R. X- ... (1)
I
R3
wherein R] to R4 each represent an alkyl or alkenyl group having from 1 to 8 carbon atoms; and X represents an anion of an organic carboxylic acid.

Accordingly, the present invention also provides a process for producing synthetic fibers with spin finish comprising the step of treating said yam with the composition for imparting spin finish as claimed in claims 1 to 8 preferably at the melt spinning stage.
In the following examples and comparative examples, parts and % are by weight.
Examples 1 to 4, Comparative Examples 1 to 4:
The following compounds (A) to (C) were selected as examples of the quaternary ammonium salt of an organic carboxylic acid to be in the spin finish of the present invention. The compound and a conventional antistatic agent were added to a base oil to prepare spin finish samples for synthetic fibers of Examples 1 to 4 and Comparative Examples 1 to 4 as shown in Table 1 below. In Table 1, the amounts of the constitutive components are

represented by "% by weight".
Composition of Base Oil:
Isotridecyl stearate 60 parts
Glycerin monooleate 10 parts
Oleyl alcohol-5E0 adduct 12 parts
Hydrogenated castor oil-15BO adduct 15 parts
Laurie acid diethanolamide 2 parts
Quaternary ammonium salt of organic carboxylic acid of the
invention:
Compound A: Triethylmethylammonium phthalate
Compound B: Tetramethylammonium maleate
Compound C: Octyltriraethylamraonium 2-ethylhexanoate
Conventional antistatic agent:
Compound D: Sodium paraffin (C14-16) sulfonate (WAROLAT U, produced by Bayer Co.) Compound E: Sodium diisooctylsulfosuccinate Compound F: Potassium pentadecenylsuccinate Compound G: Ammoniiam laurate

Table 1

Number of Spin Finish Sample

Example Comparative Example

1 2 3 4 1 2 3 4
Base Oil 95 95 95 95 95 95 95 95
Compound A 0.5
Compound B 1.0
Compound C 1.0 2.0
Compound D 1.0 1.0 1.0 1.0 3.0 1.0 1.0 1.0
Compound E 2.0
Compound F 2.0
Compound G 2.0
Next, yarns as prepared by deoiling (washing) commercially-available polyester filaments (75 deniers/36 filaments) were treated with any one of the spin finish samples of Examples 1 to 4 and Comparative Examples 1 to 4, the net weight of the spin finish adhered being 0.8 %, and then dried. The thus-treated yarn samples were tested, according to the test methods mentioned below, to measure the amount of static charges generated after the test, the amount of scum formed after the test and the amount of tar formed after the test. The results are shown in Table 2 below. Test Methods:

Amount of static charges generated:
The yarn sample was run at a speed of 300 m/min under an original tension of 10 g, while being wound around an alumina ceramic pin, and the amount of static charges generated on the sample was measured using a potentiometer. Amount of scvsm formed and dropped:
The yarn sample was rxm at a speed of 300 m/min under an original tension of 10 g, while being kept in contact with reed blades. After one hour, the amount of the substance as adhered to the reed blades and the amount of the substance as dropped down below the reed blades were measured with the naked eye. In the column for "Amount of Scum Dropped" in Table 2, "00" indicates that "no scum dropped", "O" indicates that "a little scum dropped", "A" indicates that "some scum dropped", and "X" indicates that " much scum dropped". Amount of tar formed:
The yarn sample was run at a speed of 300 m/min under an original tension of 10 g, while being wound around a hot roller having a surface temperature of 200'C . After one hour, the amount of tar formed was measured with the naked eye. In the column for "Amount of Tar Formed" in Table 2, " 00" indicates that "no tar formed", "0" indicates that "a little tar formed", "A" indicates that "some tar formed", and "X" indicates that "much tar formed".

Table 2

^■r Test Results
JNumDer \JI. Spin Finish Sample Amount of Staic Charges Generated (V) Amount of
Scum
Dropped Amount of
Tar
Formed
Example 1 (-) 40 0 or 00 0

2 (-) 50 0 0

3 (-) 60 0 0

4 ( + ) 20 0 0
Comp. Example 1 ( - ) 320 X X

2 ( - ) 260 0 A

3 ( - ) 330 X X

4 ( - ) 440 A or X X
From Table 2 above, it is understood that the spin finish samples of the present invention all have much better antistatic capacity than the conventional spin finish samples.
Next, using ion-exchanged water, aqueous 10-% emulsions each comprising any one of the spin finish samples of Examples 1 to 4 and Comparative Examples 1 to 4 were prepared. The emulsions were sealed in an incubator at 37 X; for 72 hours. After that, the nximber of the total microbes, X (cells/cc) in each emulsion was measured using " San-ai Bio Checker TTC" (produced by San-ai Petroleum Co.) and represented in terms of the common logarithmic nxomber

(log X). The results are shown in Table 3 below.
Table 3

Number of Spin Finish Sample Test Result (log X)
Example 1 0

2 0

3 1

4 0
Comparative Example 1 4 or 5

2 4 or 5

3 4 or 5

4 6 or 7
From Table 3 above, it is obvious that the spin finish samples of the present invention are effective in inhibiting the growth of bacteria, etc. Examples 5 to 12, Comparative Examples 5 to 12:
The following compounds (H) to (J) were selected as examples of the compound of formula (1) to be in the spin finish of the present invention. The compound or a conventional antistatic agent (K, L or D mentioned below) was added to a base oil comprising a polyether-type lubricant to prepare spin finish samples for synthetic fibers of Examples 5 to 12 and Comparative Examples 5 to 12 as shown in the following Tables 4 and 5, respectively. The amount of static charges generated around polyester

yams as treated with any of these samples, and the amount
of the residue as remained after heat-treatment of each
sample (this indicates the heat resistance of each sample)
were measured according to the methods mentioned below. The
test results are shown in Tables 4 and 5.
Composition of Base Oil:
Butanol-(EO/P0) random adduct (EO/PO = 50/50, mean
molecular weight = 1,400) 60 parts
Lauryl alcohol-(PO)(EO) block adduct (BO/PO = 40/60,
mean molecular weight = 1,400) 20 parts
Propylene glycol-(BO/PO) random adduct (BO/PO = 50/50,
mean molecular weight = 2,000) 10 parts
2-Ethylhexyl palmitate 10 parts
Compound of formula (1) of the invention:
Compound H: Methyltriethylammonium phthalate Compound I: Methyltriethylartmoniijm maleate Compound J: Tetramethylainoaonium 2-ethYlhexanoate
Conventional antistatic agent:
Compound K: Potassium phosphate ester of lauryl
alcohol-3B0 adduct
Compound L: Potassium phosphate ester of isostearyl
alcohol-5B0 adduct
Compound D: Mentioned above
Test Methods:
Amount of static charges generated:

Yams as prepared by deoiling (washing) commercially-available polyester filaments (75 deniers/36 filaments) were treated with any one of the spin finish samples of Examples 5 to 12 and Comparative Examples 5 to 12, the net weight of the spin finish sample adhered being 0.3 %, and then dried. The thus-treated yarn samples were run at a speed of 100 m/min or 300 m/min in an atmosphere having a temperature of 20*C and a relative humidity of 40 %, while being wound around a mat-finished chromium pin, an alumina ceramic pin or an urethane disc, and the amount of static charges generated on each sample was measured using a current-collecting potentiometer. Amount of residue remained after heat-treatment:
0.5 g of each of the spin finish samples of Examples 5 to 12 and Comparative Examples 5 to 12 was put onto a stainless steel dish having a diameter of 50 mm and a height of 10 mm, and heated in an air-circulating drier at 220'C for 8 hours. The amount of the residue remained on each dish was measured. Next, each dish was further heated in an electric furnace at 400'C for 20 minutes, and the amount of the residue still remained thereon was measured.

Table 4

Number of Spin Finish Sample

Example

5 6 7 8 9 10 11 12
Base Oil 99.7 99.7 99.7 99.5 99.0 99.7 99.5 99.0
Compound H 0.3 0.5
Compound I 0.3 0.5 1.0
Compound J 0.3 0.5 1.0
Amount of
Staic
Charges
Generated
(V)
Around mat-finished chromium
pm
100 m/min -50 -30 -10 -50 -20 -10 -40 -20
300 m/min -60 -40 -20 -60 -40 -20 -50 -40
Around
alumina
ceramic
pm
100 m/min -120 -100 -80 -100 -50 -40 -90 -60
300 m/min -150 -120 -90 -120 -90 -60 -120 -100
Around
urethane
disc
100 m/min -100 -80 -60 -100 -40 -30 -100 -90
300 m/min -120 -100 -80 -120 -80 -70 -140 -100

Percentage of Residue after Heat -Treatment
(%)
2201 , 8
hr
4001 , 20
min 0.1 0 0.1 0 0.1 0 0.1 0 0.1 0 0.15 0.05 0.1 0 0.2 0.05

Table 5

Number of Spin Finish Sample

Comparative Example

5 6 7 8 9 10 11 12
Base Oil 99.7 99.0 99.7 99.5 99.0 99.7 99.5 99.0
Compound K 0.3 1.0
Compound L 0.3 0.5 1.0
Compound D 0.3 0.5 1.0
Amount of
Staic
Charges
Generated
(V)
Around mat-finished chromium
pin
100 m/min -480 -180 -450 -300 -230 -510 -390 -220
300 m/min -580 -250 -550 -380 -280 -590 -480 -280
Around
alumina
ceramic
pm
100 m/min -720 -450 -520 -360 -280 -920 -720 -530
300 m/min -860 -550 -680 -530 -400 -980 -860 -630
Around ur ethane disc
100 m/min -320 -280 -420 -330 -220 -450 -390 -280
300 m/min -480 -360 -520 -460 -370 -520 -420 -360

Percentage of Residue after Heat -Treatment (%)
220r , 8
hr
400 r , 20
rain 0.7 0.2 1.1 0.7 0.5 0.2 1,2 0.4 1.4 0.8 0.5 0.2 0.9 0.4 1.2 0.7
From Tables 4 and 5, it is understood that the spin finish samples of the present invention each comprising a compound of formula (1) have higher antistatic capacity than the conventional spin finish samples and that the former have higher heat resistance than the latter as producing smaller amounts of tar and scum at high temperatures.
Next, a polyester was melt-spun at a winding-up speed of 3400 m/min to produce POY of 115 deniers/36 filaments, while applying to POY an aqueous 10-% emulsion of the spin finish of Example 5 or Comparative Example 5, through a nozzle, the net amount of the spin finish adhered to POY being 0.3 %. The POY sample was then processed into DTY continuously for one month, at a processing speed of 1200 m/min and at a heater temperature of 450'C / using a false twisting machine (HTS-1500 Model, produced by Teijin Machine Co.). The number of fluffs as formed around the thus-processed DTY was measured and the condition of the soiling, if any, of the guides in the heater was checked, according to the methods mentioned below. The results are

shown in Table 6 below.
Test Methods: Number of Fluffs:
One month after the start of the processing test, the yarn thus processed were rewinded at a speed of 150 m/min, while measuring the number of the fluffs as formed per 10000m of the yarn using a fluff tester (DT-140 Model, produced by Toray Co.). Degree of Soiling of Guides:
One month after the start of the processing test, the condition of the soiling, if any, of the guides in the heater was observed with the naked eye.
Table 6

Number of Spin Finish Test Results

Number of Fluffs Formed Around Processed Yam Soiling of Guides in Heater
Example 5 5 Almost not soiled.
Comparative Example 5 62 Thermal
decomposates of spin finish adhered to the guides.
From Table 6 above, it is understood that the spin finish of the present invention comprising a compound of formula (1) can exhibit extremely excellent capacity in high-speed DTY processing to be conducted in a radiation heater or the like at high temperatures, as ccxnpared with the conventional spin finish.

WE CLAIM:
1. A composition for imparting spin finish to synthetic fibers, characterized in that
the said composition contains from 0.1 to 2 0% by weight of a quaternary
ammonium salt of an organic carboxylic acid represented by general formula
(1):

wherein R1 to R4 each represent an alkyl or alkenyl group having from 1 to 8 carbon atoms; and X represents an anion of an organic carboxylic acid.
2. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, wherein said quaternary ammonium salt of an organic carboxylic acid
is prepared by reacting a tertiary amine with a dialkyl carbonate followed by
treating the reaction product with an organic carboxylic acid.
3. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, wherein the organic carboxylic acid is a monocarboxylic acid or a
dicarboxylic acid.
4. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, wherein said organic carboxylic acid is selected from maleic acid,
ophthalmic acid and 2-ethylhexanoic acid or a mixture thereof.

5. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, which contains a polyether-type lubricant.
6. The composition for imparting spin finish to synthetic fibers as claimed in
claim 5, wherein polyether-type lubricant content is from 70 to 99.5% by
weight.
7. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, wherein R1 to R4 in formula (1) each are an alkyl or alkenyl group
having from 1 to 5 carbon atoms.
8. The composition for imparting spin finish to synthetic fibers as claimed in
claim 1, wherein the quaternary ammonium salt is an octyltrimethylammonium
salt.
9. A process for producing synthetic fibers with spin finish comprising the step of
treating said yam with the composition for imparting spin finish as claimed in
claims 1 to 8 preferably at the melt spinning stage.
10. A composition for imparting spin finish to synthetic fibers substantially as
herein described.
11. A process for producing synthetic fibers with spin finish substantially as herein
described.

Documents:

1517-mas-1996 others.pdf

1517-mas-1996 abstract.pdf

1517-mas-1996 claims.pdf

1517-mas-1996 correspondence others.pdf

1517-mas-1996 correspondence po.pdf

1517-mas-1996 description (complete).pdf

1517-mas-1996 form-2.pdf

1517-mas-1996 form-26.pdf

1517-mas-1996 form-4.pdf

1517-mas-1996 form-6.pdf

1517-mas-1996 petiiton.pdf

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Patent Number

194923

Indian Patent Application Number

1517/MAS/1996

PG Journal Number

30/2009

Publication Date

24-Jul-2009

Grant Date

Date of Filing

29-Aug-1996

Name of Patentee

SANYO CHEMICAL INDUSTRIES LTD

Applicant Address

11-1, ICHINOHASHI-NOMOTO-CHO, HIGASHIYAMA-KU, KYOTO

Inventors:

#	Inventor's Name	Inventor's Address
1	HIROSHI YOSHIDA	C/O SANYO CHEMICAL INDUSTRIES LTD 11-1, ICHINOHASHI-NOMOTO-CHO, HIGASHIYAMA-KU, KYOTO
2	ICHIRO OZAKI	C/O SANYO CHEMICAL INDUSTRIES LTD 11-1, ICHINOHASHI-NOMOTO-CHO, HIGASHIYAMA-KU, KYOTO
3	SHUSUKE SAKAI	C/O SANYO CHEMICAL INDUSTRIES LTD 11-1, ICHINOHASHI-NOMOTO-CHO, HIGASHIYAMA-KU, KYOTO
4	MISAO YOSHIMI	C/O SANYO CHEMICAL INDUSTRIES LTD 11-1, ICHINOHASHI-NOMOTO-CHO, HIGASHIYAMA-KU, KYOTO

PCT International Classification Number

D06M13/224

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA