US3193407A - Finished polyolefin fibers and method of preparation - Google Patents

Finished polyolefin fibers and method of preparation Download PDF

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US3193407A
US3193407A US188865A US18886562A US3193407A US 3193407 A US3193407 A US 3193407A US 188865 A US188865 A US 188865A US 18886562 A US18886562 A US 18886562A US 3193407 A US3193407 A US 3193407A
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finish
yarn
fibers
polyethylene glycol
polyolefin
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US188865A
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Ann S Keller
Harry H Hall
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FMC Corp
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    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/477—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having six-membered heterocyclic rings
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/19—Non-high polymeric antistatic agents/n
    • Y10S260/20—Antistatic agent contains pentavalent nitrogen
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/09—Polyolefin
    • 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
    • Y10T428/2938—Coating on discrete and individual rods, strands or filaments
    • 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 yarn in textile production and sewing equipment is unsatisfactory.
  • a primary object of this invention is to provide a finished polyolefin yarn which is suitable for high speed processing, textile and sewing operations.
  • a polyolefin yarn including polyethylene, polypropylene and polyisobutylene yarn having incorporated thereon a finish consisting of from 3 to 12% by weight of a morpholine derivative of the following general formula R OIL-CH l/ RN i NHFGQ wherein R is an alkyl sulfate having 1 to 2 carbon atoms, R is an aliphatic hydrocarbon radical having from 12 to carbon atoms and R is an alkyl radical having 1 to 2 carbon atoms, and a lubricant selected from the group consisting of fatty acid monoesters of polyethylene glycols wherein the fatty acid has from 12 to 18 carbon atoms and the polyethylene glycol has an average molecular weight of from about 200 to 600 and glycerol trioleate.
  • the method of preparing finished polyolefin yarn comprises applying to said yarn the above-described finish composition in the absence of Water and a hydrocarbon oil.
  • the morpholine derivative of this invention is a known antistat for synthetic fibers applied in a mineral oil vehicle or carrier.
  • the compounds include for example N- cetyl N-ethyl morpholinium ethosulfate; N-cetyl N-methyl morpholinium methosulfate; N-lauryl N-ethyl morpholinium ethosulfate; N-stearyl N-ethyl morpholinium ethosulfate; N-soyalyl N-ethyl morpholinium ethosulfate; etc.
  • the fatty acid monoesters of polyethylene glycols having molecular weights of at least about 200 up to about 600 provide excellent lubricity for the polyolefin fibers in multifilament, monofilament and staple form when applied dry, i.e., without water or mineral oil.
  • these lubricants include the oleic acid monoester of polyethyl- 3,193,407 Fatented July 6, 1965 ene glycols having molecular weights respectively, of about 200, about 400, and about 600; the lauric acid monoester of polyethylene glycols having molecular weights respectively of about 200, about 400 and about 600; the stearic acid monoester of polyethylene glycols having molecular weights respectively of about 200 and about 400; the palmitic acid monoester of polyethylene glycols having molecular weights respectively of about 200, about 400 and about 600; etc.
  • the finishes of this invention may be applied to the fiber by any known means including bath, spray, padding, kiss roll application or the like.
  • Sorbitan monooleatc 4 Coconut oil 93 7 l-hydroxyethyl-Z-oleyl ethyl glyoxoliuium 5 ethosulfatc.
  • Sorbitan trioleate 20 Esterified pentaerythritol 75 8 Diethyl cyclohexylamine salt of la yl sulfate. 10
  • Polyolefin fibers and in particular polypropylene fibers are much more difficult to finish than other synthetic or natural polymer fibers; They are non-polar materials and as such have no ailinity for yarn finishes. They are hydrophobic and, in general, water based 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.
  • Example I a 4 200.
  • the finish was applied to the melt spun yarn in the same manner described in Example I.
  • the finished .yarn was processed in the usual fashion without demonstrating any dilficulties caused by static or excessive tension.
  • Example III A yarn finish was prepared by mixing together 5% by weight of N-cetyl N-ethyl morpholinium ethosul fate and 95% by weight of glycerol trioleate. This finish was applied to the yarn as described in Example I. The finished yarn was proccssed as usual without experiencing any difficulties caused by static or excessive tension.
  • CHZ-OHZ carbon atoms and'R" is an alkyl radical having 1-2 carbon atoms and from 97 to 95% by weight of a lubricant selected from the group consisting, of fatty acid monoesters of polyethylene glycol wherein the fatty acid has from 12-18 carbon atoms and the polyethylene glycol has an average molecular weight of from about 200 to Q about 600 and glycerol trioleate.
  • the fibers of claim 1 which is polypropylene.
  • Tl1e fibers of claim 1 wherein the lubricant is glycerol trioleate.
  • a method of preparing finished fibers which comprises treating polyolefin fibers with a finish in the absence of'water and hydrocarbon oil, said vfinish consisting of from 3-5% by weight of a morpholine derivative having the-following general formula:
  • R is an aliphatic hydrocarbon radical having *12-30 car- 'bon atoms and R is an alkyl radical having l-Z carmonoesters, polyethylene glycols wherein the fatty acid 1 has from 12-18 carbon atoms and the polyethylene glycol has an average molecular weight-of from about 200 to 7 it.
  • polypropylene fibers are treated with a finish consisting of N-cetyl N-ethyl morpholinium ethosulfate and the lauric acid monoester of a polyethylene glycol.
  • polypropylene fibers are treated with a finish consisting of N-cetyl N-ethyl morpholinium ethosulfate and glycerol trioleate.

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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 ""ce 3,193,407 FINISHED PQLYOL-EFIN FIBERS AND METHGD 0F PREPARATION Ann S. Keller, Norristown, and Harry H. Hall, Springfield, Pa., assignors, by mesne assignments, to FMC Corporation, San Jose, Calif., a corporation of Delaware No Drawing. Filed Apr; 19, 1962, Ser. No. 188,865
Claims. ((11. 117-138.?3)
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 yarn 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 charac teristics 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.
A 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 polyolefin yarn including polyethylene, polypropylene and polyisobutylene yarn having incorporated thereon a finish consisting of from 3 to 12% by weight of a morpholine derivative of the following general formula R OIL-CH l/ RN i NHFGQ wherein R is an alkyl sulfate having 1 to 2 carbon atoms, R is an aliphatic hydrocarbon radical having from 12 to carbon atoms and R is an alkyl radical having 1 to 2 carbon atoms, and a lubricant selected from the group consisting of fatty acid monoesters of polyethylene glycols wherein the fatty acid has from 12 to 18 carbon atoms and the polyethylene glycol has an average molecular weight of from about 200 to 600 and glycerol trioleate.
The method of preparing finished polyolefin yarn comprises applying to said yarn the above-described finish composition in the absence of Water and a hydrocarbon oil.
The morpholine derivative of this invention is a known antistat for synthetic fibers applied in a mineral oil vehicle or carrier. The compounds include for example N- cetyl N-ethyl morpholinium ethosulfate; N-cetyl N-methyl morpholinium methosulfate; N-lauryl N-ethyl morpholinium ethosulfate; N-stearyl N-ethyl morpholinium ethosulfate; N-soyalyl N-ethyl morpholinium ethosulfate; etc.
The fatty acid monoesters of polyethylene glycols having molecular weights of at least about 200 up to about 600 provide excellent lubricity for the polyolefin fibers in multifilament, monofilament and staple form when applied dry, i.e., without water or mineral oil. Examples of these lubricants include the oleic acid monoester of polyethyl- 3,193,407 Fatented July 6, 1965 ene glycols having molecular weights respectively, of about 200, about 400, and about 600; the lauric acid monoester of polyethylene glycols having molecular weights respectively of about 200, about 400 and about 600; the stearic acid monoester of polyethylene glycols having molecular weights respectively of about 200 and about 400; the palmitic acid monoester of polyethylene glycols having molecular weights respectively of about 200, about 400 and about 600; etc.
The finishes of this invention may be applied to the fiber by any known means including bath, spray, padding, kiss roll application or the like.
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 had 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 twenty-four 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 parafiinic oils and low molecular weight esters had a noticeable undesirable effect on the test film. Application of these materials to polyolefin yarn at spinning and the consequential softening or plasticization of this yarn corroborated the screening test results.
To demonstrate the specificity of this invention there is set forth in the following table a list of finishes the components of which have passed the screening test but which have been found unsatisfactory either in their application or in their ability to improve the characteristics of the yarn.
TABLE I No. Finish composition Percent by weight 1 Diethy cyclohexylamine salt of lauryl sulfate 3-5 Coconut oil 95-97 2 Diethyl cyclohexylamine salt of lauryl su1late 3-10 Sorbitan monooleate 1. 5-5
Butyl stearate -95. 5
3 Diethanolaminc salt; of d uryl phosphate 3 Sorbitan monooleate. 4
Butyl stearate 93 4 l-hydroxyethyl-Z-oleyl ethyl glyoxolinium 3 ethosulfate.
Sorbitan monooleate 3 Butyl stearate 94 5 Sorbi'tan monooleate 5 Butyl stearate 95 6 l-hydroxyethyl-Z-oleyl ethyl glyoxolinium 3 ethosulfate.
Sorbitan monooleatc 4 Coconut oil 93 7 l-hydroxyethyl-Z-oleyl ethyl glyoxoliuium 5 ethosulfatc.
Sorbitan trioleate 20 Esterified pentaerythritol 75 8 Diethyl cyclohexylamine salt of la yl sulfate. 10
Water 9 Diethyl cyclohexylamine salt of lauryl sulfate" 10 Diethylene glycol 90 10 Diethyl cyclohexylamine salt of lauryl sulfate; 5
Polyethylene glycol (M.W. 400) mon0oleate 11 r. Diethyl cyclonexylamine salt of lauryl sulfate. 5
Dialiphatie ether of polyethylene glycol 95 12 Ester-flied pentaerythritol 60 Nonionic emulsifying agents v 40 amass? 7 TABLE i-Contmued No Finish composition Percent by a 1 weight 13 Finish No. 12 10 Wat 90 95 3 2 20 Water 80 16 N-cetyl N-ethyl morpholinium ethosuliata Technical grade octanol '95 17 N-cetyl N-ethyl morpholiniurn ethosulfate Water 90 18 N-cetyl N-ethyl morp Diethylene glycol 9O 19 N-eetyl N-ethyl morpholinium ethosulfate... 2 Finish No. 12 98 20 Polyoxyethylenc modified tallow acid primary 5 amine. Polyethylene glycol (M.W. 200) monolaurate... 95 21 Polyethylene glycol (M.W. 2G0) monopelmgo- 100 n e. a 22 Polyethylene glycol (M.W. 1000) monostearate. 2 Polyethylene glycol (M.W. 200) monopelargo- 98 nate. V 23 Diethanolamine'salt of dilauryl phosphate. I 13 Finish No.22 9o 24 Diethanolamine salt of dilauryl phosphate 10 Polytethylene glycol (M.W. 200) monopelargo-, 90
na e. 25 Polyethylene glycol (M.W. 400) monopalmitate 2 Water; V 98 26 Diethanolamine salt of dilauryl phosphate l0 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 tradenames and/or broad chemical terms.
Polyolefin fibers and in particular polypropylene fibers are much more difficult to finish than other synthetic or natural polymer fibers; They are non-polar materials and as such have no ailinity for yarn finishes. They are hydrophobic and, in general, water based 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 method of finish application and finish composition are'extremely critical in order to obtain satis factory yarn characteristics. r n
The following examplesare set forth to demonstrate finish application and compositions in accordance with the invention.
Example I a 4 200. The finish was applied to the melt spun yarn in the same manner described in Example I. The finished .yarn was processed in the usual fashion without demonstrating any dilficulties caused by static or excessive tension.
and friction properties to the yarn.
Example III A yarn finish was prepared by mixing together 5% by weight of N-cetyl N-ethyl morpholinium ethosul fate and 95% by weight of glycerol trioleate. This finish was applied to the yarn as described in Example I. The finished yarn was proccssed as usual without experiencing any difficulties caused by static or excessive tension.
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: 7
1. Polyolefin fibers having incorporated thereon a finish consisting of 3 to 5% by weight of a morpholine derivative of the following general formula:
CHZ-OHZ carbon atoms and'R" is an alkyl radical having 1-2 carbon atoms and from 97 to 95% by weight of a lubricant selected from the group consisting, of fatty acid monoesters of polyethylene glycol wherein the fatty acid has from 12-18 carbon atoms and the polyethylene glycol has an average molecular weight of from about 200 to Q about 600 and glycerol trioleate.
. 2. The fibers of claim 1 which is polypropylene.
3. The fibers of claim 1 wherein the morpholine derivative is N-cetyl N-ethyl morpholinium ethosulfate.
4. The fibers of claim 1 wherein the lubricant is the oleic acid monoester of a polyethylene glycol.
5. The fibers of claim 1 wherein the lubricant is the lauric acid monoester of a polyethylene glycol.
6. Tl1e fibers of claim 1 wherein the lubricant is glycerol trioleate. g
'7. A method of preparing finished fibers which comprises treating polyolefin fibers with a finish in the absence of'water and hydrocarbon oil, said vfinish consisting of from 3-5% by weight of a morpholine derivative having the-following general formula:
In further processing such as draw-twisting, no difficulty with the yarn was observed. V n
The above procedure was also carried outwith a finish consisting of 10% by weight of the same morpholinium compound and by. weight of the same polyglycol ester, but the finish failed to provide satisfactory processing characteristics for the yarn. This demonstrates that component amounts for the composition are also critical.
E xample I1 V V g Y A yarn finish was prepared by inixing together 5% by.
' weight of N-cetyl N-ethyl morpholinium'ethosulfate and by weight of thelauric acid monoester of polyeth about 600'and glyceroltrioleate.
UH -CH wherein R is an alkyl sulfate having 1-2 carbon atoms,
R is an aliphatic hydrocarbon radical having *12-30 car- 'bon atoms and R is an alkyl radical having l-Z carmonoesters, polyethylene glycols wherein the fatty acid 1 has from 12-18 carbon atoms and the polyethylene glycol has an average molecular weight-of from about 200 to 7 it. The method of, c1aim7 wherein polypropylene fibers aretreated with a finish consisting of N-cetyl 'N-ethyl.
morpholinium ethosulfate and the oleic acid monoester of a polyethylene glycol.
9. The method of claim 7 wherein polypropylene fibers are treated with a finish consisting of N-cetyl N-ethyl morpholinium ethosulfate and the lauric acid monoester of a polyethylene glycol.
10. The method of claim 7 wherein polypropylene fibers are treated with a finish consisting of N-cetyl N-ethyl morpholinium ethosulfate and glycerol trioleate.
References Cited by the Examiner UNITED STATES PATENTS 2,690,426 9/54 Jefierson et a1. 117139.5 XR 2,695,270 11/54 Jeflerson et a1. 117-139.5 XR 3,009,830 11/61 Levine 117139.5 XR
WILLIAM D. MARTIN, Primary Examiner.
RICHARD D. NEVIUS, Examiner.

Claims (1)

1. POLYOLEFIN FIBERS HAVING INCORPORATED THEREON A FINISH CONSISTING OF 3 TO 5% BY WEIGHT OF A MORPHOLINE DERIVATIVE OF THE FOLLOWING GENERAL FORMULA:
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256137A (en) * 1963-07-10 1966-06-14 Us Rubber Co Adhering textile materials to rubber
US3266970A (en) * 1963-07-10 1966-08-16 Us Rubber Co Adhering textile materials to rubber
US3281311A (en) * 1963-07-10 1966-10-25 Us Rubber Co Adhering textile materials to rubber
US3327502A (en) * 1966-11-23 1967-06-27 American Can Co Knitted paper fabric
US3432898A (en) * 1965-03-19 1969-03-18 Techniservice Corp Process of stuffer-crimping lubricated synthetic fibers
US3474616A (en) * 1967-06-29 1969-10-28 Du Pont Product and process

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2690426A (en) * 1950-03-07 1954-09-28 Atlas Powder Co Lubricating compositions
US2695270A (en) * 1951-03-22 1954-11-23 Atlas Powder Co Oil soluble cationic textile antistatic agent
US3009830A (en) * 1960-03-15 1961-11-21 Hercules Powder Co Ltd Finishing polyolefin filamentary textile article and the article obtained therefrom

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2690426A (en) * 1950-03-07 1954-09-28 Atlas Powder Co Lubricating compositions
US2695270A (en) * 1951-03-22 1954-11-23 Atlas Powder Co Oil soluble cationic textile antistatic agent
US3009830A (en) * 1960-03-15 1961-11-21 Hercules Powder Co Ltd Finishing polyolefin filamentary textile article and the article obtained therefrom

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256137A (en) * 1963-07-10 1966-06-14 Us Rubber Co Adhering textile materials to rubber
US3266970A (en) * 1963-07-10 1966-08-16 Us Rubber Co Adhering textile materials to rubber
US3281311A (en) * 1963-07-10 1966-10-25 Us Rubber Co Adhering textile materials to rubber
US3432898A (en) * 1965-03-19 1969-03-18 Techniservice Corp Process of stuffer-crimping lubricated synthetic fibers
US3327502A (en) * 1966-11-23 1967-06-27 American Can Co Knitted paper fabric
US3474616A (en) * 1967-06-29 1969-10-28 Du Pont Product and process

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