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Publication numberUS3888775 A
Publication typeGrant
Publication dateJun 10, 1975
Filing dateJan 24, 1973
Priority dateJan 29, 1972
Also published asDE2304221A1, DE2304221B2, DE2304221C3
Publication numberUS 3888775 A, US 3888775A, US-A-3888775, US3888775 A, US3888775A
InventorsYoshihiro Kobayashi, Yukimichi Koizumi, Takamitsu Kondo, Yasuhiro Murase
Original AssigneeTeijin Ltd
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Oil composition for synthetic staple fibers
US 3888775 A
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Description  (OCR text may contain errors)

United States Patent Koizumi et al.

[4 1 June 10, 1975 OIL COMPOSITION FOR SYNTHETIC STAPLE FIBERS Inventors: Yukimichi Koizumi; Yoshihiro Kobayashi, both of Mihara; Yasuhiro Murase; Takamitsu Kondo, both of Matsuyama, all of Japan Assignee: Teijin Lirnited, Osaka, Japan Filed: Jan. 24, 1973 Appl. No.: 326,452

Foreign Application Priority Data Jan. 29, 1972 Japan 47-010756 U.S. Cl. 252/8.8; 252/8.9; 117/139.5 F Int. Cl D06m ll/OO Field of Search 252/86, 8.8, 8.9;

[56] References Cited UNITED STATES PATENTS 3,567,635 3/1971 Ballou.... 252/88 3,652,419 3/1972 Karg 252/88 3,691,110 9/1972 Ohfuka et al. 252/88 X Primary ExaminerStephen J. Lechert, Jr. Attorney, Agent, or Firm-Sherman & Shalloway [57] ABSTRACT 7 Claims, No Drawings OIL COMPOSITION FOR SYNTHETIC STAPLE FIBERS This invention relates to an oil for use in synthetic staple fibers, and more specifically, to a treating oil suitable for use in treating synthetic staple fibers on an open-end spinning machine constructed so as to spread a fibrous material using a combing roller, and supplying it to a rotating spinning chamber.

Great attention has been directed in recent years to ringless spinning machines in which ring travellers are not used, and various types of such a spinning frame have been studied and explotied. Of these, the drum open-end spinning frame described in the specification of U.S. Pat. No. 3,368,340 or British Pat. No. 1,1 13,003 differs in the principle of spinning from the conventional ring frames. Such an open-end spinning machine has the great advantages of shortening the spinning process, increasing the spinning speed, and winding the spun yarn on a package of a desired size, which drastically saves the labor needed for doffing and also makes it possible to produce a yarn of a high degree of uniformity.

Many oils are known for application to synthetic staple fibers to be spun on the conventional ring spinning frames. For example, for application to polyester fibers, alkyl phosphate salts, or blends of alkyl phosphate salts or alkyl surfate salts with ether and/or ester-type non-ionic surface active agents are known. For polyacrylonitrile fibers, blends of alkyl phosphate salts with polyhydric alcohol alkyl ester or cationic surface active agents are known. Furthermore, blends of alkyl sulfate salts with nonionic surface active agents, or cationic surface active agents are known for application to polypropylene fibers. For polyvinyl alcohol fibers, blends composed of mineral oils, sufated sperm oil and estertype nonionic surface active agents. These oils have compositions which have been chosen so as to prevent static build-up in each spinning step, maintain the bulkiness of lap at a low level, improve the processability on a carding, prevent fiber wrapping in the drawing, roving and spinning processes, and minimize the draft unevenness of the sliver and roving.

When synthetic staple fibers treated with such an oil are processed on an open-end spinning frame of the type described, it is substantially possible to spin the fibers, but because of the below-mentioned deficiencies, the inherent performance of the open-end spinning frame cannot be fully exhibited. Specifically, with most of these staple fibers, powdery scum containing fibers with a length of about 3 mm is deposited in the spinning chamber, and with the passage of the operating time, the nonuniformity of the yarn increases and also yarn breakage occurs frequently. It is necessary therefore to stop the operation several times until the doffing operation so as to clean the inside of the spinning chamber. Staple fibers which do not have so much powdery scum desposited thereon causes a frequent occurrence of yarn breakage by wrapping about the combing roller part and thus require great manpower to remove the wrapped fibers; also, it is difficult to obtain a yarn of uniform quality. Furthermore, the more frequent the occurrence of powdery scum is, the more tendency is there to reduced tenacities of the yarn.

The powdery scum is fine fiber wastes formed as a result of the fine cutting or shaving of fibers by a strong combing action of a combing roller, which have been transferred to the spinning chamber. This powdery scum deposits on the inner wall portion with which the fibers do not directly come into contact. When the amount of such powdery scum is increased andcannot cope with centrifugal force, the scum mixes into the fibers, and thus causes the non-uniformity or breakage of the yarn. In addition, the fibers undergo marked damage at this time by passage of the combing roller and the tenacity of the constituent single filaments decreases greatly on an average. As a result, the tenacity of the resulting yarn processed on the open-end spinning yarn is also remarkably reduced.

Accordingly, a main object of this invention is to provide an oil which can remove the above deficiencies during the spinning of synthetic fibers on an open-end sinning frame.

Another object of this invention is to provide an oil which does not cause troubles during the spinning of synthetic fibers on a ring spinning frame.

Other objects of this invention will become apparent from the following description. v

According to this invention, there is provided, as an oil for synthetic fibers, a composition consisting essentially of:

a. l0-40% by weight of a fatty acid ester of a monohydric or polyhydric alcohol,

b. lO-40% by weight of a reaction product formed between 2 moles of a fatty acid containing 8 22 carbon atoms and 1 mol of polyethylene polyamine,

c. l0-30% by weight of an antistatic agent, and

d. 10-70% by weight of an emulsifier.

Synthetic fibers that can be treated with the oils 0 this invention are, for example, polyester, polyamide, polyacrylonitrile, polyolefin and polyvinyl chloride fibers.

Examples of the fatty acid ester of monohydric alcohols used in the present invention are monobasic acid ester such as methyl laurate, oleyl laurate, octyl myristate, isopropyl palmitate, octyl palmitate, lauryl isostearate, butyl stearate, amyl stearate, oleyl stearate, lauryl oleate, or oleyl oleate, and dibasic acid esters such as dioctyl adipate, dioctyl sebacate, dioleyl sebacate or dioctyl azelate. Examples of the fatty acid esters of polyhydric alcohols are ethylene glycol dioleate, glycerine trilaurate, trimethylol propane dilaurate, and trimethylol propane tridecanoate.

These fatty acid esters (a) as a component of the oil of this invention serve to impart a high degree of lubrication at a time when fibers to be treated undergo a strong and high-speed combing action by a combing roller, and to reduce the occurence of the powdery scum. In order to obtain this effect, it is necessary that the amount of this component (a) should be at least 10 percent by weight based on the total amount of the oil. For more effects, it is preferred that the amount be at least 15 percent by weight. Usually, it is sufficient that the amount be 35 percent by weight, and at most 40 percent by weight. If the amount of this component exceeds 40 percent by weight, the wrapping of the fibers around the combing roller of an open-end spinning frame becomes frequent, and the wrapping of the fibers around a card cylinder also becomes frequent in the fore-spinning step, in which case it is difficult to form a uniform web.

The term reaction product formed between 2 mols of a fatty acid having 8 to 22 carbon atoms and l mol Q 3 of polyethylene'gpolyamine" denotes a mixture composed mainly ofia compound expressed by the general formula wherein each of R, and R is a hydrocarbon radical having 7-21 carbon atoms and n is an integer. In the following, this may sometimes be referred to simply as polyamide (b).

The polyamide (b) used in this invention greatly contributes to the reduction of static friction of fibers to be treated, and the prevention of the fibers from wrapping around the combing roller. Substances which have an effect of preventing this wrapping may be those used as a component of an oil for treating synthetic staple fibers to be spun on the ring spinning frame, for example, alkylsulfate salts, or fatty acid soaps. However, if such a substance is used instead of the polyamide (b) in this invention, lubrication of the fibers at high speed is greatly reduced, which in turn causes a considerable formation of the powdery scum in an open-end spinning frame. On the other hand, the polyamide (b), when blended with the fatty acid ester (a) even in a relatively small amount, brings about a reduction in the wrapping of the fibers around the combing roller and, surprisingly, also a reduction in the amount of the powdery scum. However, such an effect is greatly reduced when the fatty acid which constitutes the polyamide has less than 8 carbon atoms. Therefore, it is desirable that the number of carbon atoms of the fatty acid be at least 8, preferably at least 10. On the other hand, if the number of carbon atoms exceeds 22, the fibers treated have reduced lubricating properties, and also it is difficult to convert the fatty acid ester and the polyamide to an emulsified form. Furthermore, when n in formula (1) above exceeds 5, the reduction in lubricating prop erty at high speed and the difficulty of emulsification may sometimes take place undersirably.

In order to reduce the wrapping of the fibers arouind the combing roller, the amount of the polyamide (b) should be at least 10 percent by weight based on the total amount of the oil. If the amount exceeds 40 percent by weight, friction between the fibers becomes too low, and a web of fibers at a card tends to sag. Furthermore, the sliver becomes bulky, or the oil becomes separated from the surfaces of the fibers. The preferred amount of the polyamide (b) is usually to 35 percent by weight. When these components are used in the form of an aqueous emulsion, the sum of the amounts of the fatty acid ester (a) and the polyamide (b) should not exceed 70 percent by weight based on the total amount of the oil, since otherwise difficulty of emulsification might sometimes arise.

The antistatic agent (c) used in the present invention may be selected from various cationic surface active agents of the quaternary ammonium salt type, amphoteric surface active agents of the alkyl betaine type, and polyoxyethylene-added alkylamines. The antistatic agent, however, tends to exert an adverse effect on the prevention of the powdery scum. Accordingly, the amount of the antistatic agent should be minimized and it should not be used in an amount more than necessary for imparting sufficient antistatic properties at the temperature and humidity usually employed. Usually, the

amount of the antistatic agent is 10 to 30 percent by weight.

The emulsifier (d) is used to emulsify the above ingredients, and is preferably composed mainly of a nonionic surface active agent. Examples of the nonionic surfactant are polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl phenols, polyoxyethylene fatty acid esters, an ethylene oxide adduct of castor oil, fatty acid monoesters of glycerine, fatty acid monoesters of sorbitan, and ethylene oxide adducts of these esters. The amount of the emulsifier (d) is usually at least 10 percent by weight based on the total amount of the oil. In order to obtain a more stable emulsion, it is desirable to blend it in an amount of more than 20 percent by weight. However, in order to obtain sufficient effects of the ingredients blended, the amount of the emulsifier should be minimized. If the proportion of the emulsifier exceeds percent by weight, there is not so considerable formation of the powdery scum, but the wrapping of the fibers around the combing roller and the yarn breakage become very frequent. It is desirable therefore to limit the amount to not more than 60 percent by weight.

In addition to the esssential ingredients (a), (b), (c) and (d), the oil of this invention may, if desired, contain other conventional additives such as a rust-proof agent, antioxidant, antiseptic or emulsion stabilizer.

Usually, the oil of this invention is applied to fibers in the form of an aqueous emulsion. Specific procedures for application include the dipping method, roller contacting method, and spray method. The concentration of the oil in the aqueous emulsion can vary according to the conditions. For example, when the dipping method is used, amounts of 0.5 to 5 percent by weight are suitable. The application of the oil to fibers can be performed at any desired stage in the process for producing fibers. Fibers to which the oil has been applied by the dipping method may be dried and heattreated, and the oil may be applied thereto again.

The amount of the oil to be deposited on synthetic fibers is preferably within the range of 0.08 to 0.30 percent by weight of fibers. If the amount is smaller than 0.08 percent by weight, sufficient lubricating property cannot be obtained, and the amount of the powdery scum deposited in an open-end spinning step increases. Furthermore, the antistatic properties of the fibers are insufficient, and troubles occur in the fore-spinning step owing to static build-up.

The amount of the powdery scum in the open-end spinning step can be reduced to a lesser degree with larger amounts of the oil depositied on the fibers. However, it is usually sufficient that the amount should be 0.25 percent by weight, at most 0.3 percent by weight. If the amount exceeds 0.3 percent by weight, the wrapping of fibers around the combing roller in the openend spinning step becomes frequent, and moreover the wrapping of the fibers to a card cylinder and the disturbance of the web in the fore-spinning step take place. Also, the fibers very frequently wrap around rollers in the drawing step.

As described above, when synthetic staple fibers treated with the oil of this invention are spun on a drum open-end spinning frame built so as to spread the fibers by a combing roller, the occurence of the powdery scum and the wrapping of the fibers onto the combing roller are reduced, and the spinning frame can be operated continuously for prolonged periods of time. Furthermore, the spun yarns are uniform as compared with spum yarns obtained on the conventional ring spinning frame. Thus, the characteristics of the open end spinning frame can be sufficiently exhibited. As will be shown by the following Examples, synthetic fibers treated with the oil of this invention can be spun with good results not only on an open-end spinning frame but also on a ring spinning frame.

The following Examples will illustrate the present invention.

EXAMPLE 1 A drawn tow of polyethylene terephthalate (monofilament denier having an intrinsic viscostiy, as measured in an ortho-chlorophenol solution, of 0.65 was immersed in each of aqueous emulsions of the l 1 oils indicated in Tables l2, and squeezed to such an extent that the oil take-up was 0.15 percent by weight based on the weight of the tow. The tow was then crimped, and heat-treated for 30 minutes in a dry heat at 120C. The tow was cut into portions each having a length of 38 mm, and these staple fibers were treated by a conventional technique and subjected to a card. Then, the carded fibers were passed twice through a drawing frame to produce a sliver (200 grains/6 yards). The sliver was processed on an open-end spinning frame, and the occurance of the powdery scum, the fiber wrapping around a combing roller, and the number of yarns broken were measured. The results are shown in Tables 1 and 2.

The open-end spinning frame used was of the ED- 200 type produced by Toyota Automatic Loom Works, Ltd. A yarn of count was spun for 5 hours on one spinning frame (200 spindles) with the speeds of the rotor and the combing roller maintained at 30,000 rpm and 7,000 rmp respectively. When the yarn was broken during this time, it was tied immediately. The total number of yarn breakages was measured, and converted to a value per spinning frame per hour. This value was made the number of yarn breakages (per one frame per hour). The degree of occurrence of the powdery scum was evaluated after the 5-hour spinning on a scale of the following five grades with respect to the amount of the scum deposited within the rotor in any 10 spindles, and the average value was calculated. If this degree is grade 4 or more (at the worst at least grade 3.5), almost no trouble occurs during operation, and the spinning frame can be operated for prolonged periods of time.

Standard of evaluating the occurrence of scum Grade 5: No deposition at all Grade 4: Slight deposition in part Grade 3: Uniform deposition in a thin layer Grade 2: Uniform deposition in a thick layer Grade 1: Spinning condition becomes poor because of the peel-off of the scum Table 1 Oils Spinning properties Run Ingredients Propor- Number Number Scum No. tion(%) of yarn of (grade) breakages fiber- (per one wrapping frame around a per hour) combing roller (per one frame per hour) Com- PEG*(600) paramonopalmitate tive PEG (400) Exam- A monomyristy- 40 48.2 21.6 3.5 ple rate POE**( 3) 20 lauryl sulfate Na salt Com- POE(1 lauryl sulfate para- Na salt 12.8 1.2 2.0 tive B Mineral oil 20 Example PEG (200) monostea- 20 rate POE(3) cetyl ether 10 ditto C Alkyl phosphate 50 16.4 0 2.5

K salt Fatty acid K salt 20 POE-added alkyl ether 30 'PEG=polyethylcne glycol POE=polyoxyethylcnc Table 2 Composition of oil Spinning Properties Fatty Poly- Anti- Emul- Number Number Run acid amide static sifyof yarn of fiber No. ester agent ing breakage wrapping agent (per around Scum frame a comb (grade) per ing hour) roller (per frame per hour) Comparative Example D 50 20 30 36.8 l8.2 4.0 Example of this invention E 40 14.4 2.6 4.4 F 30 20 20 30 4.8 0.4 4.2 G 20 30 20 30 2.8 0 4.2 H 10 40 20 30 6.8 0 4.0 Comparative Example I 0 50 2O 30 I28 0 3.0 Example of this invention .l l0 10 20 60 7.4 1.8 3.6 K 35 20 10 8.8 0.8 4.6

The oils used in Runs Nos. A, B and C were those used on polyester fibers to be spun on a ring spinning frame, or those having similar compositions. In Table 2, the fatty acid ester was butyl sterate, and the polyamide was a reaction product formed between 2 mols of palmitic acid and 1 mol of diethylene triamine. The antistatic agent was oleyl dimethyl ethyl ammoniumethosulfate, and the emulsifying agent was at least one of monoand di-palmitates and monoand di-stearates of polyethylene glycol (molecular weight 200 to 2,000).

The following conclusions can be drawn from Tables 1 to 2.

In the Comparative Examples, no particularly serious trouble occurred in the fore-spinning step, but in the open-end spinning frame, various troubles were observed. In Run No. A, the occurrence of the scum was relatively slight, but the number of fiber wrapping around a combing roller and the number of yarn breakages were very large. In Runs Nos. B and C, the number of fiber wrapping around a combing roller and the number of yarn breakages were small, but there was considerable occurrence of the scum. Accordingly, it is seen that the oils which are used in the conventional ring spinning step cannot be directly applied to the open-end spinning step. In Run No. D (a comparative example in which an oil not containing the polyamide was used), the occurrence of scum was slight, but the number of fiber wrapping around a combing roller increases, thus also bringing about an increase in the number of yarn breakages. In Run No. I (a comparative example in which an oil not containing the fatty acid ester was used), no fiber wrapping around a combing roller was observed, but probably because of a reduced friction between the fibers, yarn breakage frequently occurred as a result of slippage. Powdery scum was also formed in great quantities.

In contrast, in the Examples of the present invention (Runs Nos. E, F, G, H, J and K), spinning could be performed in good condition with reduced occurrence of scum, reduced fiber wrapping around a combing roller and reduced yarn breakage.

EXAMPLE 2 In Run No. F in Example I, an aqueous emulsion was prepared using another fatty acid ester instead of the butyl stearate. Polyester fibers treated with the aqueous emulsion under the same conditions as in Example 1 were subjected to an open-end spinning frame. As a result, the spinning properties were good as shown in Table 3.

An aqueous emulsion was prepared in accordance with the recipe used in Run No. G of Example 1, using a polyamide prepared from various fatty acids or by varying the molecular weight [n in the formula (1)] of polyethylene polyamine. Polyester staple fibers treated with the aqueous emulsion under the same conditions as in Example 1 were processed on an open-end spinning frame. As a result, the spinning properties were good as shown in Table 4.

Table 4 Polyamides Spinning properties Run Fatty acid n Number of Number of Occur- Nos. yarn breakfiber wraprence ages (per ping (per of scum one frame one frame (grade) per hour) per hour) P Laurie 2 5.8 0.4 4.0

acid Q Laurie 4 8.2 0 4.0

acid R Palmitic 4 6.8 0 4.2

acid S Stearic 2 3.4 0 4.2

acid

EXAMPLE 4 The oil used in Run No. G was applied in varying amounts in the form of aqueous emulsion to polyester fibers, and the staple fibers were mixed with cotton sliver (mixing ratio 35 percent by weight) in the drawing step to produce a sliver (200 grain/6 yards). The sliver was processed in the same type of open-end spinning frame as used in Example l to form a yarn of 30 count.

The spinning properties were good as shown in Table 5 over a considerable wide range of the oil take-up.

Polyacrylonitrile staple fibers 1.5 denier, 38 mm) were dipped in a 0.5 percent emulsion of the oil used in Run No. G, and squeezed by a centrifugal dehydrator to an emulsion take-up of 45 percent, followed by drying at 80C. The fibers so treated were processed on an open-end spinning frame under the same conditions as in Example 1 to produce a yarn of 20 count. The occurrence of scum was grade 4.0, and there was no fiber wrapping around a combing roller. The yarn breakage was 4.2 per frame per hour. Thus, the spinning properties were good.

EXAMPLE 6 Polyester fibers with an oil take-up ofO. 14 percent by weight as used in Example 4 were mixed with cotton sliver (mixing ratio 35 percent by weight) in the drawing step to roduce a sliver (300 grain/6 yards). The mixture was processed on a spinning frame to form a roving (250 grain/30 yards). The roving was then processed on a conventional ring spinning frame to produce a yarn of 45 count (the number of twists 21.4 turns/inch, speed of spindle rotation 12000 rpm. 50 spindles operated for hours). For comparision, commerically available polyester staple fibers (TEIJIN TETORON, SD l.4 38) used for a ring spinning frame were spum. It was found that the polyester fibers could be spun with good results without showing any appreciable difference from the comparative staple fibers in respect of the breakage of the roving in a flyer frame, the fiber wrapping around a roller and the yarn breakage, in a ring spinning frame, and the quality of the spun yarn.

What is claimed is:

1. An oil for use in synthetic staple fibers, said oil consiting essentially of (a) 10-40 percent by weight of a monobasic acid ester or dibasic acid ester of a monohydric or polyhydric alcohol, (b) 10-40 percent by weight ofa reaction product formed between 2 mols of a fatty acid containing 8-22 carbon atoms and 1 mol of polyethylene polyamine and having the formula wherein each of R and R is a hydrocarbon radical having 7-21 carbon atoms and n is an integer. (c) 10-30 percent by weight of an antistatic agent and ((1) 10-70 percent by weight of an emulsifying agent other than (a) and (b) above.

2. An oil for use in synthetic staple fibers, said oil consisting essentially of (a) 15-35 percent by weight of a monobasic acid ester or dibasic acid ester ofa monohydric or polyhydric alcohol, (b) 15-35 percent by weight of a reaction product formed between 2 mols of a fatty acid containing 8-22 carbon atoms and 1 mol of polyethylene polyamine and having the formula wherein each of R add R is a hydrocarbon radical having 7-21 carbon atoms and n is an integer, (c) 10-30 percent by weight of an antistatic agent and (d) 20-60 percent by weight of an emulsifying agent other than (a) and (b) above.

3. The oil of claim 1 wherein said monobasic acid ester is selected from the group consisting of methyl laurate, oleyl laurate, octyl myristate, isopropyl palmitate, octyl palmitate, lauryl isostearate, butyl stearate, amyl stearate, oleyl stearate, lauryl oleate or oleyl oleate and wherein the Clibasic acid ester is selected from the group consisting of dioctyl adipate, dioctyl sebacate, dioleyl sebacate or dioctyl azelate.

4. The oil of claim 1 wherein component (a) is a fatty acid ester of a polyhydric alcohol selected from the group consisting of ethylene glycol dioleate, glycerine trilaurate, trimethylol propane dilaurate, and trimethylol propane tridecanoate.

5. The oil of claim 1 wherein said antistatic agent is a cationic surface active agent, amphoteric surface active agent or polyoxyethylene alkylamine.

6. The oil of claim 1 wherein said emulsifier (d) comprises a nonionic surface active agent selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl phenols, polyoxyethylene fatty acid esters, an ethylene oxide adduct of castor oil, fatty acid monesters of glycerine, fatty acid monoesters of sorbitan, and ethylene oxide adducts of these esters.

7. The oil of claim 2 consisting essentially of (a) 15-35 percent by weight of a monobasic acid ester or dibasic acid ester of a monohydric or polyhydric alcohol selected from the group consisting of methyl laurate, oleyl laurate, octyl myristate, isopropyl palmitate, octyl palmitate, lauryl isosterate, butyl stearate, amyl stearate, oleyl stearate, lauryl oleate or oleyl oleate, ethylene glycol dioleate, gylcerine trilaurate, trimethylol propane dilaurate, and trimethylol propane tridecanoate, (b) 15-35 percent by weight of a compound having the formula 1 2 2 2 wherein each of m and 2 is hydrocarbon radical having 9-21 carbon atoms and n is an integer of from l-5, (c) 10-30 percent by weight of an antistatic agent selected from cationic surface active agents, amphoteric surface agents and polyoxyethylene alkylamines and ((1) 20-60 percent by weight of an emulsifying agent selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl phenols, polyoxyethylene fatty acid esters, and ethylene oxide adduct of castor oil, fatty acid monoesters of glycerine, fatty acid monoesters of sorbitan, and ethylene oxide adducts of these esters.

Patent Citations
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US3691110 *Jun 2, 1970Sep 12, 1972Asahi Chemical IndAntistatic treating agent from polyepoxide-polyamine reaction
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3993571 *Apr 11, 1975Nov 23, 1976Allied Chemical CorporationButyl stearate, sorbitan monooleate and polyoxyethylene(20)sorbitan monooleate
US4122018 *May 16, 1977Oct 24, 1978Henkel Kommanditgesellschaft Auf AktienSmoothing agents for treating textile fiber material
US4201680 *Jun 22, 1978May 6, 1980Henkel Kommanditgesellschaft Auf AktienSmoothing agents for treating textile fiber material
US4261839 *Mar 19, 1979Apr 14, 1981Hoechst AktiengesellschaftTertiary butyl ethers as fiber preparation agents
US4505956 *Apr 30, 1982Mar 19, 1985Takemotoyushi Co. Ltd.Lubricant for treating synthetic fibers
US6537662 *Jan 11, 1999Mar 25, 20033M Innovative Properties CompanySoil-resistant spin finish compositions
US7772413Nov 17, 2005Aug 10, 2010Glaxo Group LimitedAmide and peptide derivatives of tetraalkylenepentamines as transfection agents
WO2006053783A1 *Nov 17, 2005May 26, 2006Glaxo Group LtdAmide and peptide derivatives of tetraalkylenepentamines as transfection agents