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US3296019A - Poly (ethylene oxide) adducts of fatty oils and fatty amines as antistatic coating for polyolefin fibers - Google Patents

Poly (ethylene oxide) adducts of fatty oils and fatty amines as antistatic coating for polyolefin fibers Download PDF

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Publication number
US3296019A
US3296019A US188838A US18883862A US3296019A US 3296019 A US3296019 A US 3296019A US 188838 A US188838 A US 188838A US 18883862 A US18883862 A US 18883862A US 3296019 A US3296019 A US 3296019A
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Prior art keywords
fatty
ethylene oxide
oil
polyolefin fibers
finish
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US188838A
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Ann S Keller
Harry H Hall
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FMC Corp
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FMC Corp
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer

Definitions

  • This invention relates to finished polyolefin fibers. More particularly, it relates to polyolefin yarns or fibers having applied finishes which enable the yarns to be satisfactorily processed and utilized in the commercial production of textiles and in machine sewing operations.
  • Polyolefin yarns for example polypropylene and polyethylene yarns, tend to develop high electrostatic charges and excessive tensions when running over guides, godets and other objects during processing and subsequent handling.
  • the utilization of unfinished polyolefin yarns in textile production and sewing equipment is unsatisfactory.
  • the primary object of this invention is to provide a finished polyolefin yarn which is suitable for high speed processing, textile and sewing operations.
  • a finish composition for polyolefin fibers comprising from about 10 to about 30% by weight of a finish consisting essentially of l to parts by weight of a polyethylene oxide modified fatty oil and 1 part by weight of a polyethylene oxide modified C C fatty acid primary amine, and from about 90 to 70% by weight of water.
  • This finish composition is applied to polyolefin yarns including, for example, polyethylene, polypropylene and polyisobutylene yarns or fibers by any known means including bath, spray, padding, kiss roll application or the like.
  • water base finish compositions are unsatisfactory for application to polyolefin yarn or fibers because of the hydrophobic nature of these polymers.
  • the present finish composition is an exception and provides unexpectedly good lubrication and static suppression.
  • the fatty oils of the invention include, for example, castor oil, cotton seed oil, flax seed oil, olive oil, peanut- "ice oil, corn oil, coconut oil, soya bean oil, palm oil, perilla oil, tallow, whale oil, bone oil, etc. If desired, these oils may be partially hydrogenated toincrease saturation and vary the melting range thereof.
  • the fatty oils are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty oil.
  • the adducts generally have an average or from about 15 to or more ethylene oxide units per glycerine molecule in the fatty oil and preferably from 20 to about 30 ethylene oxide units per molecule.
  • the fatty acid primary amines of this invention are preferably derived from the amination of fatty acids or a mixture of fatty acids obtained from the distillation of the products of hydrolysis of the above described fatty oils.
  • the C -C fatty acids include, for example, la-uric acid, myristic acid, palmitic acid, stearic acid, ole-ic acid, linoleic acid, etc. Mixtures of these acids, for example those obtained from tallow oil, namely, stearic, p-almitic and oleic, are as good or better than individual fatty acids for the purposes of this invention.
  • the fatty acid primary amines are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty acid amines wherein each fatty amine molecule has attached thereto a chain having an average of from about 10 to 30' and more ethylene oxide units and preferably from about 15 to 25 ethylene oxide units per molecule of fatty amine.
  • Polyolefin fibers and in particular polypropylene fibers are much more diflicult to finish than other synthetic or natural polymer fibers. They are non-polar materials and as such have no affinity for the usual yarn finishes. They are hydrophobic, and in general, water base finish compositions cannot be used to obtain a satisfactory finish.
  • the polyolefin fibers are degraded by treatment with hydrocarbon oil base compositions and become undesirably soft. For these reasons, the finish composition is extremely critical in order to obtain satisfactory yarn characteristics.
  • Example I proximately 800 denier, 34 filament yarn by means of a kiss roll 6 inches in diameter and 1 /2 inches wide just prior to primary take-up.
  • the finished yarn was collected onto a standard take-up tube with ease.
  • the finish was also found to be an aid in processing the yarn through a draw-twisting unit.
  • Example II A finish was prepared and applied to polypropylene fiber as described in Example I except that 4 parts of the polyethylene oxide a-dduct of hydrogenated castor oil were used instead of 2 parts and the combination was mixed with water at a concentration of 15% by weight. The fiber was found to have even better processing properties than the finished yarn of Example I.
  • Polyolefin fibers having incorporated thereon a finish consisting essentially of l to 5 parts by weight of a polyethylene oxide modified fatty oil having an average of at least 15 ethylene oxide units per glyceride molecule and 1 part by weight of a polyethylene oxide modified primary amine having an average of at least 10 ethylene oxide units per amine molecule said primary amine obtained from a C -C fatty acid.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent POLY(ETHYLENE OXIDE) ADDUTS OF FATTY OILS AND FATTY AMINES AS ANTISTATIC COATING FOR POLYOLEFIN FIBERS Ann S. Keller, Norristown, and Harry H. Hall, Springfield, Pa., assignors, by mesne assignments, to FMC Corporation, San Jose, Calif., a corporation of Delaware N0 Drawing. Filed Apr. 19, 1962, Ser. No. 188,838
4 Claims. (Cl. 117138.8)
This invention relates to finished polyolefin fibers. More particularly, it relates to polyolefin yarns or fibers having applied finishes which enable the yarns to be satisfactorily processed and utilized in the commercial production of textiles and in machine sewing operations.
Polyolefin yarns, for example polypropylene and polyethylene yarns, tend to develop high electrostatic charges and excessive tensions when running over guides, godets and other objects during processing and subsequent handling. The utilization of unfinished polyolefin yarns in textile production and sewing equipment is unsatisfactory.
Static and tension problems have been encountered in the use of other natural and synthetic polymer yarns, and finishes which are satisfactory from both the standpoints of application and use have been developed for them. However, the polyolefins have different physical characteristics than most other filament forming polymers and conventional finishes and methods for application thereof are not suitable or effective in providing the necessary fiber to fiber lubrication, proper fiber to metal frictional behavior, and adequate static suppression.
The primary object of this invention is to provide a finished polyolefin yarn which is suitable for high speed processing, textile and sewing operations.
It is another object of this invention to provide a method of finishing polyolefin fibers which is effective in providing fiber lubrication and static suppression.
These and other objects are accomplished in accordance with this invention with a finish composition for polyolefin fibers comprising from about 10 to about 30% by weight of a finish consisting essentially of l to parts by weight of a polyethylene oxide modified fatty oil and 1 part by weight of a polyethylene oxide modified C C fatty acid primary amine, and from about 90 to 70% by weight of water. This finish composition is applied to polyolefin yarns including, for example, polyethylene, polypropylene and polyisobutylene yarns or fibers by any known means including bath, spray, padding, kiss roll application or the like.
Generally speaking, water base finish compositions are unsatisfactory for application to polyolefin yarn or fibers because of the hydrophobic nature of these polymers. The present finish composition, however, is an exception and provides unexpectedly good lubrication and static suppression.
The fatty oils of the invention include, for example, castor oil, cotton seed oil, flax seed oil, olive oil, peanut- "ice oil, corn oil, coconut oil, soya bean oil, palm oil, perilla oil, tallow, whale oil, bone oil, etc. If desired, these oils may be partially hydrogenated toincrease saturation and vary the melting range thereof.
The fatty oils are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty oil. The adducts generally have an average or from about 15 to or more ethylene oxide units per glycerine molecule in the fatty oil and preferably from 20 to about 30 ethylene oxide units per molecule.
The fatty acid primary amines of this invention are preferably derived from the amination of fatty acids or a mixture of fatty acids obtained from the distillation of the products of hydrolysis of the above described fatty oils. The C -C fatty acids include, for example, la-uric acid, myristic acid, palmitic acid, stearic acid, ole-ic acid, linoleic acid, etc. Mixtures of these acids, for example those obtained from tallow oil, namely, stearic, p-almitic and oleic, are as good or better than individual fatty acids for the purposes of this invention. The fatty acid primary amines are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty acid amines wherein each fatty amine molecule has attached thereto a chain having an average of from about 10 to 30' and more ethylene oxide units and preferably from about 15 to 25 ethylene oxide units per molecule of fatty amine.
Many lubricant-antistat combinations were investigated to develop a satisfactory finish composition for polyolefin fiber. Before combinations of lubricants and antistats were tried, however, a screening test was conducted to determine whether the lubricant or antistat material would degrade the polyolefin. Screening involved placing approximately 0.2 ml. of the liquid lubricant or antistat onto a sheet of polypropylene film which has been secured to a glass plate. A piece of graph paper was placed between the film and the glass and served two purposes; it would indicate penetration of the film by the liquid, and also give an indication of the spreading action of the lubricant or antistat. The material passed the screening test if 24 hours of film contact produced no change in film appearance such as waviness or puckering. If puckering did occur it was assumed that it was caused by penetration of the lubricant or antistat into the film and this type of behavior would also occur with a polypropylene fiber. Puckering was considered to be caused by plasticization or a similar phenomenon and test materials causing it were rejected.
The above screening test indicated that paraffinic oils and low molecular weight esters had a noticeable undesirable effect on the test film. Applications of these materials to polyolefin yarn at spinning and the consequential softening or plasticization of this yarn corroborated the screening test results.
To demonstate the specificity of this invention there is set forth in the following table a list of finishes, the components of which have passed screening tests but which have been found unsatisfactory either in their application or in their ability to improve characteristics of the yarn.
TABLE I No. Finish Composition Percent By Weight 1 Diethyl cyclohexylamine salt of lauryl sulfate 3-5 Coconut oil- 95-97 2 Diethyl cyclohexylamine salt of lauryl sulfate 3-10 Sorbitan monooleate 1. Butyl stearate 85-95. 5 3 Diethanolamine salt of dilauryl phosphate. 3 Sorbitan monooleate 4 Butyl stearate 93 4. l-hydroxyethyl-Z-oleyl ethyl glyoxolinium ethosulfate 3 Sorbitan monooleate 3 Butyl stearate 94 5. Sorbitan monooleate 5 Butyl stearate 95 6- 1-hydroxyethyl-2-oleyl ethyl glyoxolinium ethosulfate 3 Sorbitan monooleate 4 Coconut oil 93 7 l-hydroxyethyl-2-oleyl ethyl glyoxol 5 Sorbitan trioleate. Esterified pentaerythritol. 75 8. Diethyl cyclohexylamine salt of lauryl sulfate- 10 Water. 90 9 Diethyl cyclohexylamine salt of lauryl sulfate 10 Diethylene glycol... 90 10 Deithyl cyclohexylarnine salt of lauryl sulfate 5 Polyethylene glycol (M.W. 400) monooleate. 95 11 Diethyl cyclohexylamine salt of lauryl sulfat 5 Dialiphatic ether of polyethylene glycol 95 12 Esterified pentaerythritoL- 60 Nonionic emulsifying agent 13 10 90 95 3 N-cetyl N-ethyl morpho 2 Finish No. 14- 20 Water 80 N-cetyl N-eth 5 Technical grade octanol 95 N -cetyl N-ethyl morpholiuium ethosulfate- 10 Water 90 N-eetyl N-ethyl morpholinium ethosulfate- 10 Diethylene glycol 90 Ncetyl N-ethyl morpholinium ethosulfate 2 Finish No. 12. ....i 98 Polyoxyethylene modified tallow acid primary amine 5 Polyethylene glycol (M.W. 200) monolaurate 95 Polyethylene glycol (M.W 200) monopelargonate" 100 Polyethylene glycol (M.W 1000) monostearate. 2 Polyethylene glycol (M.W 200) monopelargonate 98 Diethanolamine salt of dllauryl phosphate 5 Finish No. 22- 95 Diethanolamine salt of dilauryl phosphate 10 Polyethylene glycol (M.W. 200) monopelargonate-. 90 Polyethylene glycol (M.W. 400) monopalmitate 2 Water. 98 Diethanolamine salt of dilauryl phosphate 10 Polyethylene glycol (M.W. 200) monolaurate 90 In addition to the above yarn finish compositions, many other unsatisfactory combinations were tested which were identifiable only under chemical trade names and/or broad chemical terms.
Polyolefin fibers and in particular polypropylene fibers are much more diflicult to finish than other synthetic or natural polymer fibers. They are non-polar materials and as such have no affinity for the usual yarn finishes. They are hydrophobic, and in general, water base finish compositions cannot be used to obtain a satisfactory finish. The polyolefin fibers are degraded by treatment with hydrocarbon oil base compositions and become undesirably soft. For these reasons, the finish composition is extremely critical in order to obtain satisfactory yarn characteristics.
The following examples are set forth to demonstrate finish application and composition in accordance with the invention.
Example I proximately 800 denier, 34 filament yarn by means of a kiss roll 6 inches in diameter and 1 /2 inches wide just prior to primary take-up. The finished yarn was collected onto a standard take-up tube with ease. The finish was also found to be an aid in processing the yarn through a draw-twisting unit.
Example II A finish was prepared and applied to polypropylene fiber as described in Example I except that 4 parts of the polyethylene oxide a-dduct of hydrogenated castor oil were used instead of 2 parts and the combination was mixed with water at a concentration of 15% by weight. The fiber was found to have even better processing properties than the finished yarn of Example I.
Various changes and modifications may be made in practicing the invention without departing from the spirit and scope thereof and, therefore, the invention is not to be limited except as defined in the appended claims.
We claim:
1. Polyolefin fibers having incorporated thereon a finish consisting essentially of l to 5 parts by weight of a polyethylene oxide modified fatty oil having an average of at least 15 ethylene oxide units per glyceride molecule and 1 part by weight of a polyethylene oxide modified primary amine having an average of at least 10 ethylene oxide units per amine molecule said primary amine obtained from a C -C fatty acid.
5 2. The polyolefin fibers of claim 1 wherein the fatty oil is hydrogenated castor oil.
3. The polyolefin fibers of claim 1 wherein the C12 C fatty acid is a mixture of acids derived from tallow. 4. Polypropylene fibers having incorporated thereon a finish consisting essentially of 1 to 5 parts by weight of a polyethylene oxide modified hydrogenated castor oil having an average of at least 15 ethylene oxide units per glyceri-de molecule and 1 part by Weight of a polyethylene oxide modified primary amine having an average of at least 10 ethylene oxide units per amine molecule and wherein said primary amine is obtained from the fatty acids derived from talloW.
References Cited by the Examiner UNITED STATES PATENTS Schoeller et a1, 2608.9 Cresswell et al.
Walles.
McGary et al. 260-23 Levine 117--139.5 Kocay et a1. 2528.8 Swern et al. 260-23 LEON J. BERCOVITZ, Primary Examiner.
R. W. GRIFFIN, C. W. IVY, Assistant Examiners.

Claims (1)

1. POLYOLEFIN FIBERS HAVING INCORPORATD THEREON A FINISH CONSISTING ESSENTIALLY OF 1 TO 5 PARTS BY WEIGHT OF A POLYETHYLENE OXIDE MODIFIED FATTY OIL HAVING AN AVERAGE OF AT LEAST 15 ETHYLENE OXIDE UNITS PER GLYCERIDE MOLECULE AND 1 PART BY WEIGHT OF A POLYETHYLENE OXIDE MODIFIED PRIMARY AMINE HAVING AN AVERAGE OF AT LEAST 10 ETHYLENE OXIDE UNITS PER AMINE MOLECULE SAID PRIMARY AMINE OBTAINED FROM A C12-C18 FATTY ACID.
US188838A 1962-04-19 1962-04-19 Poly (ethylene oxide) adducts of fatty oils and fatty amines as antistatic coating for polyolefin fibers Expired - Lifetime US3296019A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957936A (en) * 1971-07-22 1976-05-18 Raduner & Co., Ag High temperature process for modifying thermoplastic filamentous material
EP0491293A3 (en) * 1990-12-17 1992-11-19 Kimberly-Clark Corporation Polyolefin articles and methods of making same
US5258221A (en) * 1990-12-17 1993-11-02 Kimberly-Clark Corporation Polyolefin article

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2614289A (en) * 1947-09-04 1952-10-21 American Cyanamid Co Fiber-forming apparatus
US2832697A (en) * 1956-04-30 1958-04-29 Dow Chemical Co Method for applying antistatic agents to polymeric substances and destaticized articles thereby obtained
US2999827A (en) * 1959-01-21 1961-09-12 Union Carbide Corp Epoxy coating compositions
US3009830A (en) * 1960-03-15 1961-11-21 Hercules Powder Co Ltd Finishing polyolefin filamentary textile article and the article obtained therefrom
US3048539A (en) * 1959-06-29 1962-08-07 American Cyanamid Co Antistatic textile lubricant finishes
US3049504A (en) * 1954-04-12 1962-08-14 Swern Daniel Epoxidized animal fat diacetoglycerides as plasticizers

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2614289A (en) * 1947-09-04 1952-10-21 American Cyanamid Co Fiber-forming apparatus
US3049504A (en) * 1954-04-12 1962-08-14 Swern Daniel Epoxidized animal fat diacetoglycerides as plasticizers
US2832697A (en) * 1956-04-30 1958-04-29 Dow Chemical Co Method for applying antistatic agents to polymeric substances and destaticized articles thereby obtained
US2999827A (en) * 1959-01-21 1961-09-12 Union Carbide Corp Epoxy coating compositions
US3048539A (en) * 1959-06-29 1962-08-07 American Cyanamid Co Antistatic textile lubricant finishes
US3009830A (en) * 1960-03-15 1961-11-21 Hercules Powder Co Ltd Finishing polyolefin filamentary textile article and the article obtained therefrom

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957936A (en) * 1971-07-22 1976-05-18 Raduner & Co., Ag High temperature process for modifying thermoplastic filamentous material
EP0491293A3 (en) * 1990-12-17 1992-11-19 Kimberly-Clark Corporation Polyolefin articles and methods of making same
US5258221A (en) * 1990-12-17 1993-11-02 Kimberly-Clark Corporation Polyolefin article

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