US2683101A - Treated textiles - Google Patents
Treated textiles Download PDFInfo
- Publication number
- US2683101A US2683101A US189068A US18906850A US2683101A US 2683101 A US2683101 A US 2683101A US 189068 A US189068 A US 189068A US 18906850 A US18906850 A US 18906850A US 2683101 A US2683101 A US 2683101A
- Authority
- US
- United States
- Prior art keywords
- hours
- textile
- treated
- static
- fibers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004753 textile Substances 0.000 title claims description 36
- 239000002216 antistatic agent Substances 0.000 claims description 10
- 239000000835 fiber Substances 0.000 description 9
- 230000003068 static effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 4
- -1 Undecyl Methyl Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002780 morpholines Chemical class 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 2
- VXYGFTZDXZHPHP-UHFFFAOYSA-N 4-dodecyl-4-methylmorpholin-4-ium Chemical compound CCCCCCCCCCCC[N+]1(C)CCOCC1 VXYGFTZDXZHPHP-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- QDQHWKZZJJDBND-UHFFFAOYSA-M 4-ethyl-4-hexadecylmorpholin-4-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+]1(CC)CCOCC1 QDQHWKZZJJDBND-UHFFFAOYSA-M 0.000 description 1
- WXICWQGWDGVMIP-UHFFFAOYSA-N 4-methylmorpholin-4-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[NH+]1CCOCC1 WXICWQGWDGVMIP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- RIHSFACLJWVMJY-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.C(C(O)C(O)C(=O)O)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O Chemical compound C(C1=CC=CC=C1)(=O)O.C(C(O)C(O)C(=O)O)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O RIHSFACLJWVMJY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920001875 Ebonite Polymers 0.000 description 1
- YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2418—Coating or impregnation increases electrical conductivity or anti-static quality
- Y10T442/2459—Nitrogen containing
Definitions
- Tow. filament into staple arranges the staple in suitable fashion and produces a loosely spun yarn. commonly known as Top/ Unless the electrojstati'cdualities or the tow are cntrolled,-produc- 1 tics of a continuous top is impossible.
- This invention relates to the production of treated textiles and related materials. More specifically the invention. relates to the production of treated fibers, staple fibers, felts, threads, cords,
- morp-holine derivatives which act as textil'e antistatic agents are materials of the class A onion? R-N ⁇ orno Lower Alkyl wherein R is a long chain aliphatic radical containing from 11 to carbon atoms and A isan anion. Suitable derivatives may be formed by substituting within the above formula, the com.- pcnents suggested in Table I:
- Electrostatic charges were then induced by first rubbing 12 times with a glass rod to induce an electrostatic charge and then,after observation as indicated below, rubbing 12 times with a hard rubber rod to induce an opposite electrostatic charge. Observations of the charges induced were given electrostatic rating as indicated in Table II.
- the concentration of the quaternary ammonium derivative in the aqueous. solution. may vary over a wide range depending upon the method of application and subsequent treatment of the soaked textile. In general, it has been found that efiective static protection requires that there be deposited on. the textile at least 0.4% or the quaternary ammonium compound based on the weight of the treated textile. This level can be reached satisfactorily with aqueous concentrations as low as 2%. The upper limit is governed only by the solubility of the antistatic agent.
- the ratio of liquor to textile is not critical. An approximate ratio of 50:1 has been found convenient and employed in the examples.
- Example I Observed Static Rating Test Conditions Air dried, room temperature After 22 hours at 65 C After 96 hours at 65 C After 168 hours at 65 C After 240 hours at 65 C.
- Test Conditions Observed Static Rat Air dried, room temperature After 22 hours at 65 C After 96 hours at 65 0.- After 168 hours at 65 O After 240 hours at 65 C After 240 hours at 65 C. After 240 hours at 65 C.
- Example III An identical yarn treated in a manner such as described in Example I without the antistatic agent was rated as shown below:
- Example IV A nylon yarn identical to that of Example I was treated in the manner described in Example I employing a 5% solution of lauryl methyl morpholinium methosulfate. were obtained.
- nylon has been used to quantitatively demonstrate the value of the morpholine quaternary ammonium compounds as antistatic agents since it is highly susceptible to such static charges, it will be apparent to those skilled in the art that other textiles of natural and especially synthetic origin may likewise be treated.
- acetate rayon, Viscose rayon, Orlon (a polyacrylonitrile) cotton, wool, silk, glass, linen and the like have all been found amenable to the process. Satisfactory electrostatic elimination is obtained by treatment of these various materials as indicated below:
- a treated textile as wherein the textile is rayon.
- a process of treating textiles to render them anti-static which comprises treating said textile with an aqueous solution containing at least 2% of a compound of the formula defined in claim -1 defined in claim 1
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
the trade as Tow. filament into staple, arranges the staple in suitable fashion and produces a loosely spun yarn. commonly known as Top/ Unless the electrojstati'cdualities or the tow are cntrolled,-produc- 1 tics of a continuous top is impossible.
Patented July 6, 1954 TREATED TEXTILES Allen V. Riley, Jr., New Castle, Del., and Richard D. Fine III, Merchantville, N. L, assignors to Atlas Powder Company, Wilmington, DeL, a
corporation of'Delaware I No Drawing.
Application October 7, 1950, SerialNo. 189,068
11 Claims. (Cl. 117---139.5)
This invention relates to the production of treated textiles and related materials. More specifically the invention. relates to the production of treated fibers, staple fibers, felts, threads, cords,
yarns, pellicles, filaments fabrics and the like of synthet'c or natural origin.
It is an object of the present invention to provide treated fibers, staple fibers, felts, cords,
threads, yarns, pellicles, filaments, fabrics and the like for use in textile and related manufacture which are antistatic in nature.
Other objects will become apparent the course of the following specification and appended claims.
Adaptability of fibers, staple fibers, felts, cords, threads, yarns, pellicles, filaments, fabrics and the like to automatic handling operations is of extreme importance in the manufacture of textiles. Modern high speed machinery technique requires a feed of appropriate characteristics to permit uninterrupted and fault free operation. The electrostatic qualities of the textile being handled can frequently spell the success or failure of such undertakings. Thus, yarn which tends to balloon, due to the accumulation of static charges as it passes over equipment, is entirely unsatisfactory for operations such as knitting where it produces uneven stitches and knotting. Furthermore, in the spinning of yarns, the presence of static electrical charges upon the particles being spun, will cause production of uneven yarns and a high percentage of slubs. Themost' acute problem arises in the use of the more modern machinery such as for instance the converters employed in'the Tow'to Top-spinning process. This machineis fed a bundle of continuous synthetic filament in parallel arrangement known to It then'cuts or breaks the In accordance with the present invention, it
has been discovered that by treating textile fibers,
staple fibers, felts, cords, threads, yarns, pellicles, filaments, fabrics and the like with a composition of matter comprising an aqueous solution of a clas of organic morpholine derivatives to be describedhereinafter, they can be rendered antistatic in nature.
The morp-holine derivatives which act as textil'e antistatic agents are materials of the class A onion? R-N \orno Lower Alkyl wherein R is a long chain aliphatic radical containing from 11 to carbon atoms and A isan anion. Suitable derivatives may be formed by substituting within the above formula, the com.- pcnents suggested in Table I:
Table I Lower Alkyl A Undecyl Methyl Halide Lauryl Ethyl Nitrate Myristyl Amyl Phosphate Oetyl Alkylsulfate Oleyl Cyanide Stcaryl Acetate Soyalyl Benzoate Citrate Tartrate static agents, the textile fiber in the form of a skein or yarn was first soaked for five minutes in a 5% aqueous solution of the quaternary. morpholinium derivative. It was centrifuged for 30 seconds in a small basket extractor and dried in air.
Electrostatic charges were then induced by first rubbing 12 times with a glass rod to induce an electrostatic charge and then,after observation as indicated below, rubbing 12 times with a hard rubber rod to induce an opposite electrostatic charge. Observations of the charges induced were given electrostatic rating as indicated in Table II.
Table II Qbservatlon 0 No evidence of electrostatic charge.
.. Just enough electrostatic charge to disturb a filament. Sulicient electrostatic charge to lift a filament from 3 7, Sufficient electrostatic charge to cause a slight ballooni'ng of'a'ske'in'.
Suliicient electrostatic charge to cause considerable ballooning of a skein.
The concentration of the quaternary ammonium derivative in the aqueous. solution. may vary over a wide range depending upon the method of application and subsequent treatment of the soaked textile. In general, it has been found that efiective static protection requires that there be deposited on. the textile at least 0.4% or the quaternary ammonium compound based on the weight of the treated textile. This level can be reached satisfactorily with aqueous concentrations as low as 2%. The upper limit is governed only by the solubility of the antistatic agent. The ratio of liquor to textile is not critical. An approximate ratio of 50:1 has been found convenient and employed in the examples.
The following examples are cited to illustrate the invention. They are not intended to limit it in any way.
Example I Observed Static Rating Test Conditions Air dried, room temperature After 22 hours at 65 C After 96 hours at 65 C After 168 hours at 65 C After 240 hours at 65 C.
After 240 hours at 65 C. After 2 hours at 65 C. After 240 hours at 65 C. After 240 hours at 65 C. After 240 hours at 65 C.
and 48 hours at 105 C and 96 hours at 105 C.-. and 192 hours at 105 C. and 240 hours at 105 O and 336 hours at 105 0.-
Oahu-0900000 Substituting cetyl Example 11 methyl morpholinium methosulfate for the quaternary ammonium compound of Example I, the following observations were made.
Test Conditions Observed Static Rat Air dried, room temperature After 22 hours at 65 C After 96 hours at 65 0.- After 168 hours at 65 O After 240 hours at 65 C After 240 hours at 65 C. After 240 hours at 65 C.
After 240 hours at 65 C.
, After 240 hours at 65 0.
After 240 hours at 65 0.
and 48 hours at 105 C. and 96 hours at 105 C." and 192 hours at 105 0.. and 240 hours at 105 0.- and 336 hours at 105 C.
NHHOQOQOCO OOOOOOOOOO Example III An identical yarn treated in a manner such as described in Example I without the antistatic agent was rated as shown below:
6 Observed Static Rating Test Conditions Air dried, room temperature 4 3 After 22 hours at C 3 3 After 96 hours at 65 C .l 3 3 After 168 hours at 65 C 3 3 After 2 10 hours at 65 C 4 4 After 240 hours at 65 0. and 48 hours at 105 0... 4 3 After 240 hours at 65 C. and 96 hours at 105 C 4 3 Example IV A nylon yarn identical to that of Example I was treated in the manner described in Example I employing a 5% solution of lauryl methyl morpholinium methosulfate. were obtained.
The following data Example V Substituting soyalyl ethyl morpholinium ethosulfate for the quaternary employed in Example IV above, identical results were obtained, except that after 240 hours at 65 C. and 192 hours at C., the negative charge was rated at 2 and the positive charge at 1.
All of the morpholine derivatives described are very valuable in controlling the undesirable accumulation of electrostatic charges. However, it is obvious from the examples above that the cetyl derivatives (Examples I and II) show an exceptional capacity in that regard.
While nylon has been used to quantitatively demonstrate the value of the morpholine quaternary ammonium compounds as antistatic agents since it is highly susceptible to such static charges, it will be apparent to those skilled in the art that other textiles of natural and especially synthetic origin may likewise be treated. Thus, acetate rayon, Viscose rayon, Orlon (a polyacrylonitrile) cotton, wool, silk, glass, linen and the like have all been found amenable to the process. Satisfactory electrostatic elimination is obtained by treatment of these various materials as indicated below:
It will be apparent that many variations can be made without departing from the scope of the invention which is defined in the appended claims.
What is claimed is:
1. A treated textile containing an anti-static agent of the formula C H2- 0 H2 Lower Alkyl wherein R, is an aliphatic radical containing from 11 to 20 carbon atoms, A is a lower alkyl sulfate radical; said anti-static agent being at least 0.4% by weight of the treated textile.
2. A treated textile as defined in claim 1 wherein the textile is formed of synthetic fibers.
3. A treated textile as defined in claim 1 wherein the textile is nylon.
4. A treated textile as wherein the textile is glass.
5. A treated textile as wherein the textile is rayon.
6. A treated textile as defined in claim 1 wherein the textile is acetate rayon.
7. A treated textile as defined in claim 1 wherein the textile is formed of acrylic fibers.
8. A treated textile containing as an anti-static agent at least 0.4% of cetyl ethyl morpholinium ethosulfate, based on the weight of the treated textile.
9. A treated textile containing as an anti-static agent at least 0.4% of soyalyl ethyl morpholinium ethosulfate, based on the weight of the treated textile.
10. A treated textile containing as an antistatic agent at least 0.4% of lauryl methyl morpholinium methosulfate, based on the weight of the treated textile.
11. A process of treating textiles to render them anti-static which comprises treating said textile with an aqueous solution containing at least 2% of a compound of the formula defined in claim -1 defined in claim 1 A OHz-CH: H CH2C2 Lower alkyl References Cited in the file of this patent UNITED STATES PATENTS Number Name Date ,137,235 Carothers Nov. 22, 1938 2,186,628 Dickey Jan. 9, 1940 2,197,930 Jackson et a1. Apr. 23, 1940 2,417,992 Niederl et al Mar. 25, 1947 2,563,506 Werntz Aug. 7, 1951
Claims (1)
1. A TREATED TEXTILE CONTAINING AN ANTI-STATIC AGENT OF THE FORMULA
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE506231D BE506231A (en) | 1950-10-07 | ||
| US189068A US2683101A (en) | 1950-10-07 | 1950-10-07 | Treated textiles |
| FR1042511D FR1042511A (en) | 1950-10-07 | 1951-10-01 | Improvements to processes for rendering textile materials antistatic |
| GB22913/51A GB702089A (en) | 1950-10-07 | 1951-10-02 | Improvements in or relating to a method of rendering a textile resistant to the accumulation of electrostatic charges |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US189068A US2683101A (en) | 1950-10-07 | 1950-10-07 | Treated textiles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2683101A true US2683101A (en) | 1954-07-06 |
Family
ID=22695782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US189068A Expired - Lifetime US2683101A (en) | 1950-10-07 | 1950-10-07 | Treated textiles |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2683101A (en) |
| BE (1) | BE506231A (en) |
| FR (1) | FR1042511A (en) |
| GB (1) | GB702089A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117113A (en) * | 1957-08-22 | 1964-01-07 | Btr Industries Ltd | Antistatic composition |
| US3230193A (en) * | 1961-05-16 | 1966-01-18 | Du Pont | Polyurethanes stabilized by phosphines |
| US3772070A (en) * | 1971-04-05 | 1973-11-13 | Burlington Industries Inc | Applying antistatic finish on synthetic textiles |
| US3868270A (en) * | 1972-12-04 | 1975-02-25 | Du Pont | Fibers with finish containing organic phosphates and sulphates |
| US4091165A (en) * | 1971-07-01 | 1978-05-23 | Mitsubishi Petrochemical Co., Ltd. | Surface processing copolymer for synthetic papers |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2137235A (en) * | 1937-02-15 | 1938-11-22 | Du Pont | Shaped articles from polymeric materials |
| US2186628A (en) * | 1937-11-26 | 1940-01-09 | Eastman Kodak Co | Yarn conditioning process and composition therefor |
| US2197930A (en) * | 1936-12-03 | 1940-04-23 | Eastman Kodak Co | Method of treating cellulose organic derivative cut staple fibers |
| US2417992A (en) * | 1942-04-14 | 1947-03-25 | Joseph B Niederl | N, n-dialkyl morpholinium alkylsulfates |
| US2563506A (en) * | 1951-08-07 | Quaternary ammonium salts of |
-
0
- BE BE506231D patent/BE506231A/xx unknown
-
1950
- 1950-10-07 US US189068A patent/US2683101A/en not_active Expired - Lifetime
-
1951
- 1951-10-01 FR FR1042511D patent/FR1042511A/en not_active Expired
- 1951-10-02 GB GB22913/51A patent/GB702089A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563506A (en) * | 1951-08-07 | Quaternary ammonium salts of | ||
| US2197930A (en) * | 1936-12-03 | 1940-04-23 | Eastman Kodak Co | Method of treating cellulose organic derivative cut staple fibers |
| US2137235A (en) * | 1937-02-15 | 1938-11-22 | Du Pont | Shaped articles from polymeric materials |
| US2186628A (en) * | 1937-11-26 | 1940-01-09 | Eastman Kodak Co | Yarn conditioning process and composition therefor |
| US2417992A (en) * | 1942-04-14 | 1947-03-25 | Joseph B Niederl | N, n-dialkyl morpholinium alkylsulfates |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117113A (en) * | 1957-08-22 | 1964-01-07 | Btr Industries Ltd | Antistatic composition |
| US3230193A (en) * | 1961-05-16 | 1966-01-18 | Du Pont | Polyurethanes stabilized by phosphines |
| US3772070A (en) * | 1971-04-05 | 1973-11-13 | Burlington Industries Inc | Applying antistatic finish on synthetic textiles |
| US4091165A (en) * | 1971-07-01 | 1978-05-23 | Mitsubishi Petrochemical Co., Ltd. | Surface processing copolymer for synthetic papers |
| US3868270A (en) * | 1972-12-04 | 1975-02-25 | Du Pont | Fibers with finish containing organic phosphates and sulphates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB702089A (en) | 1954-01-06 |
| BE506231A (en) | 1900-01-01 |
| FR1042511A (en) | 1953-11-02 |
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