US2597947A - Textile treating compositions - Google Patents
Textile treating compositions Download PDFInfo
- Publication number
- US2597947A US2597947A US722290A US72229047A US2597947A US 2597947 A US2597947 A US 2597947A US 722290 A US722290 A US 722290A US 72229047 A US72229047 A US 72229047A US 2597947 A US2597947 A US 2597947A
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- United States
- Prior art keywords
- salt
- composition
- salts
- cellulose acetate
- lubricating
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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
- 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
- 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
Definitions
- present invention relates to the dressing of textile materials, especially for the purpose :of facilitating their manipulation.
- textile filaments, fibres, yarnsand'the like are dressed with 'salts of quaternary ammonium bases and or- 'ganic sulphonic acids.
- the salts for use according to the invention may be derived from mono-or poly-acid quaternary ammonium bases or from mixed aminoquaternary ammonium bases in which the amino group may be primary, secondary or tertiary.
- Preferably all the quaternary ammonium and the amino groups in the "bases are aliphatic groups, i. e. the nitrogen atom of each such "group is not directly attached to an aromatic nucleus.
- the quaternary bases contain at most one alcoholic hydrcxyl group for each quaternary nitrogen atom.
- the aliphatic "radicle of the 'sulphonic acid is an unsubstituted saturated ihydrocarbon :radicle, and accordingly :preferred acids are cetyl and :stearyl sulphonic :acids and-particularly laur-yl sulphonic acid.
- the aliphatic sulphonic acids -: may be produced by the reaction of an aqueous solution of the sodium salt of the corresponding aliphatic -sulphate -with-sodium sulphite at elevated tempera- :tures, e. :g. "above l- 0., and pressures, -e. g. about -500 lbs, and subsequent isolation :of the acids 'by known methods.
- compositions of the present invention *should preferably contain, either inthe acid or in the .basefrom which they are derived, groups containing several carbon atoms, e. -g. 6 or more, united one to another in the group.
- groups containing several carbon atoms e. -g. 6 or more, united one to another in the group.
- the salts may be producedby the reaction of the free quaternary ammonium base in a suitable solvent with the free sulphonic-acid.
- a free quaternary ammonium base in methanol solution as formed by the'treatment 0f the chloride or bromide of "the base with the calculated quantity of caustic soda or potash :in methanol solution and after the separation 'of the precipitated alkali halide .maybe treated with the acid and the desired salt .so formed separated from the methanol.
- the salts may be formed by the double decomposition of the halide, sulphate, oxalate or other suitable salt of the quaternary ammonium base and the sodium or other metallic salt of the organic sulphonic acid in a medium in which one or other reaction product is insoluble.
- the acid oxalate of a quaternary ammonium base and the potassium salt of the organic sulphonic acid may be reacted in aqueous solution to form the desired salt with precipitation of potassium hydrogen oxalate.
- the salts may be produced without the preliminary formation of a quaternary ammonium compound, as by reacting a tertiary amine with the appropriate ester of the organic sulphonic acid to produce the desired salt directly.
- dressing according to the invention is conveniently effected by applying to the materials solutions of the salts, for example aqueous solutions.
- the materials can, for example, be moistened with these solutions and thereafter dried in order to leave a deposit of the salt on the material.
- continuous filaments as spun may be treated with the solutions, e. g. by wick, bath, roller or spray methods, dried, if desired, as by passage through a hot chamber, and wound or twisted and wound.
- Continuous filament yarn in hank or package form may be immersed in the solutions, excess liquid removed by centrifuging, pressing or otherwise, and the material dried.
- cellulose acetate or other cellulose ester or ether staple fibre may be similarly treated or sprayed with a solution of the salt; by this treatment the subsequent working up into sliver, yarn or other form, may be greatly facilitated due to the reduced tendency of the dressed material to become electrified.
- Textile materials dressed with salts according to the present invention are found to have no substantial corrosive action on machine parts with which they contact.
- a particular merit of the salts described is that they are soluble in many of the oils commonly used in the lubrication of textile materials in order to facilitate the manipulation of the latter.
- a solution of a salt of a quaternary ammonium base and organic sulphonic acid in a lubricating oil By using as lubricant a solution of a salt of a quaternary ammonium base and organic sulphonic acid in a lubricating oil, the tendency of the material to develop electrical charges is simultaneously reduced.
- the lubricating oils which may be employed for this purpose are, for instance, animal or vegetable oils, e. g. coconut oil, olive oil or arachis oil, and esters of polymerised and/ or oxidised unsaturated fatty acids, especially those of the monohydric alcohols, e. g.
- lubricating oil is the polymerised and oxidised oleic acid ester of methyl cyclohexanol.
- Lubricants comprising mineral oils may also be used in conjunction with the salts to produce dressings in accordance with the present invention. If desired, the lubricating oil and the quaternary ammonium salt may be applied to the textile materials in separate operations, the salt being applied, for example, in aqueous solution.
- a lubricating oil can frequently be facilitated by the simultaneous presence of a higher fatty alcohol, particularly one containing twelve or more carbon atoms, e. g. oleyl alcohol.
- a higher fatty alcohol particularly one containing twelve or more carbon atoms, e. g. oleyl alcohol.
- Other hydroxylated compounds may also be present in the lubricating composition to assist in the incorporation of the salt and to modify the characteristics of the lubricant.
- assistants it is often possible to incorporate in the oil greater proportions of the salt than would otherwise be possible.
- An example of a suitable lubricating composition particularly for use with cellulose acetate materials, has the following composition:
- a composition suitable for lubricating cellulose acetate textile material consisting essentially of a lubricating oil, a higher fatty alcohol, and a salt of an aliphatic sulphonic acid containing 8 to 18 carbon atoms with ethylene-bis (triethyl ammonium hydroxide), the proportion of alcohol being sufficient to render the composition homogeneous and the proportion of the salt sufficient to render cellulose acetate textile material difiicult to electrify when lubricated with the composition.
- a composition suitable for lubricating cellulose acetate textile material consisting essentially of a lubricating oil, a higher fatty alcohol of at least 12 carbon atoms, and a salt of ethylene-bis(triethyl ammonium hydroxide) with an aliphatic sulphonic acid of which the aliphatic radicle is an unsubstituted saturated hydrocarbon radicle of 8 to 18 carbon atoms, the proportion of the alcohol being sufiicient to render the composition homogeneous and the a proportion of the salt suiiicient to render cellulose acetate textile material difiicult to electrify when lubricated with the composition.
- a composition suitable for lubricating cellulose acetate textile material comprising a lubricating oil, a higher fatty alcohol and a salt of ethylene-bis(triethyl ammonium hydroxide) with lauryl sulphonic acid, the proportion of the alcohol being sufficient to render the composition homogeneous and the proportion of the salt suflicient to render cellulose lubricated with the composition.
- a composition suitable for lubricating cellulose acetate textile material comprising a mixture of mineral lubricating oil and vegetable oil, oleyl alcohol and a salt of ethylene-bis(triethyl ammonium hydroxide) with lauryl sulphonic acid, the proportion of the alcohol being sufficient to render the composition homogeneous and the proportion of the salt sufficient to render cellulose acetate textile material difficult to electrify when lubricated with the composition.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented May 27, 1952 TEXTILE IEREATING COMPOSITIONS Horac'e Finningley Oxley and *Edward Boaden Thom-as, "Spondon, near Derby, and Harry Charles. Murfitt, London, England, assignors to Celanese Corporation of American: corporation 7 of Delaware NoDrawing. Application January '15, 1947, Se-
rial No. 722,290. In Great Britain January 25,
present invention relates to the dressing of textile materials, especially for the purpose :of facilitating their manipulation.
Various textile materials, forexample, natural .silk and cellulose ester and ether artificial silk, have a low electrical -.conductivity and .tend to acquire and retain electrical charges, especially while undergoing textile operations such as, for example, twisting and winding, knitting, and the workingupofstaple fibre yarns. Such-electrification of the materials leads togreatdifiiculties in carrying .out many :of ,the textile .opera- .tions which they .are normally required to .un- .dergo, as, for example, .those mentioned above.
Numerous agents have been proposed .forapplication to textile materials witha view .to reducing electrification, but in many cases the agents have been found to induce serious corrosion .of machine parts with which they come into contact.
In the manipulation of textile materials it is also generally desirable to lubricate them so as to facilitate the operations. This is particularly the case, for example, with dry-spun cellulose acetate immediately after its production and prior to its being wound or twisted and wound. Again, the knitting'properties of cellulose acetate yarn are greatly improved by lubrication. It is clearly of great advantage if the agent which reduces electrification can be applied simultaneously with the lubricant, and particularly if the agent is soluble-in the lubricating oil.
According to the present invention textile filaments, fibres, yarnsand'the like are dressed with 'salts of quaternary ammonium bases and or- 'ganic sulphonic acids.
The salts for use according to the invention may be derived from mono-or poly-acid quaternary ammonium bases or from mixed aminoquaternary ammonium bases in which the amino group may be primary, secondary or tertiary. Preferably all the quaternary ammonium and the amino groups in the "bases are aliphatic groups, i. e. the nitrogen atom of each such "group is not directly attached to an aromatic nucleus. Especially'high 'efiiciency in reducing the electrification oftextile materials -has been found to be possessed by the salts of "bases containing two 'or more quaternary ammonium groups. *These salts formed from organic -sulphonic acids and poly-acid quaternary ammonium bases are believed to be new compounds, and the "invention includes their manufacture as well as compositions containing rthem. Examples of suitable bases, the organic sulphonic acid ;salts of which '4 Claims. (Cl. 252-.-8.75)
may beaemployed according to the invention, are lauryl trimethyl ammonium hydroxide, diethylmethyl ethanol-ammonium hydroxide, triethyl ethanol-ammonium ihydroxide, cyclohexyl diethyl methyl ammonium hydroxide, ethylene bis-(triethyl ammonium hydroxide), ethylene bisdiethylethanol-ammonium hydroxide). hexamethylene bis-(triethyl ammonium hydroxide) and ethylene bis-'(lauryl-diethyl ammonium "hy- .droxide). Preferably the quaternary bases contain at most one alcoholic hydrcxyl group for each quaternary nitrogen atom.
Particularly valuable salts :are 'those derived from the aliphatic sulphonic acids, more particu- =larly such ascontain more than B carbon atoms, andespecially those "containing :l2-or more carrbonatoms, whether the-aliphatic radicle is saturated or unsaturated. Preferably the aliphatic "radicle of the 'sulphonic acid is an unsubstituted saturated ihydrocarbon :radicle, and accordingly :preferred acids are cetyl and :stearyl sulphonic :acids and-particularly laur-yl sulphonic acid. The aliphatic sulphonic acids -:may be produced by the reaction of an aqueous solution of the sodium salt of the corresponding aliphatic -sulphate -with-sodium sulphite at elevated tempera- :tures, e. :g. "above l- 0., and pressures, -e. g. about -500 lbs, and subsequent isolation :of the acids 'by known methods.
':Salts -for use-in :the compositions of the present invention *should preferably contain, either inthe acid or in the .basefrom which they are derived, groups containing several carbon atoms, e. -g. 6 or more, united one to another in the group. The presence of a straight chain-of several-carbon atoms, especiallyfi, 10, 12 or more carbon atoms, is particularly advantageous.
Various methods are available for the manufacture 'of the salts. Thus, they may be producedby the reaction of the free quaternary ammonium base in a suitable solvent with the free sulphonic-acid. For example, a free quaternary ammonium base in methanol solution, as formed by the'treatment 0f the chloride or bromide of "the base with the calculated quantity of caustic soda or potash :in methanol solution and after the separation 'of the precipitated alkali halide .maybe treated with the acid and the desired salt .so formed separated from the methanol.
"stages day heating and stirring .in each stage, with 1290 =gms. ethyl :chloride :at LOO- C. for .24
hours. After :each stage excess ethyl chloride is removed by distillation together with some methanol and the residual liquor treated in the cold with a solution of 400 gms. of sodium hydroxide in 3 litres of methanol. Finally, sodium chloride is removed by filtration to leave a methanol solution of the desired base, containing small amounts of diethyl ethanolamine and sodium chloride. This residue is treated with the calculated quantity of lauryl-sulphonic acid and the tertiary base removed by vacuum distillation to leave the desired salt, slightly contaminated with sodium chloride. According to a second method, the salts may be formed by the double decomposition of the halide, sulphate, oxalate or other suitable salt of the quaternary ammonium base and the sodium or other metallic salt of the organic sulphonic acid in a medium in which one or other reaction product is insoluble. Thus, for example the acid oxalate of a quaternary ammonium base and the potassium salt of the organic sulphonic acid may be reacted in aqueous solution to form the desired salt with precipitation of potassium hydrogen oxalate. Alternatively, the salts may be produced without the preliminary formation of a quaternary ammonium compound, as by reacting a tertiary amine with the appropriate ester of the organic sulphonic acid to produce the desired salt directly.
For reducing the electrification of textile materials, e. g. materials of cellulose ester or ether, dressing according to the invention is conveniently effected by applying to the materials solutions of the salts, for example aqueous solutions. Thus, the materials can, for example, be moistened with these solutions and thereafter dried in order to leave a deposit of the salt on the material. For instance, continuous filaments as spun may be treated with the solutions, e. g. by wick, bath, roller or spray methods, dried, if desired, as by passage through a hot chamber, and wound or twisted and wound. Continuous filament yarn in hank or package form may be immersed in the solutions, excess liquid removed by centrifuging, pressing or otherwise, and the material dried. Again, cellulose acetate or other cellulose ester or ether staple fibre may be similarly treated or sprayed with a solution of the salt; by this treatment the subsequent working up into sliver, yarn or other form, may be greatly facilitated due to the reduced tendency of the dressed material to become electrified. Textile materials dressed with salts according to the present invention are found to have no substantial corrosive action on machine parts with which they contact.
A particular merit of the salts described is that they are soluble in many of the oils commonly used in the lubrication of textile materials in order to facilitate the manipulation of the latter. By using as lubricant a solution of a salt of a quaternary ammonium base and organic sulphonic acid in a lubricating oil, the tendency of the material to develop electrical charges is simultaneously reduced. The lubricating oils which may be employed for this purpose are, for instance, animal or vegetable oils, e. g. coconut oil, olive oil or arachis oil, and esters of polymerised and/ or oxidised unsaturated fatty acids, especially those of the monohydric alcohols, e. g.
cyclohexanol or methyl cyclohexanol. An example of the last-mentioned type of lubricating oil is the polymerised and oxidised oleic acid ester of methyl cyclohexanol. Lubricants comprising mineral oils may also be used in conjunction with the salts to produce dressings in accordance with the present invention. If desired, the lubricating oil and the quaternary ammonium salt may be applied to the textile materials in separate operations, the salt being applied, for example, in aqueous solution.
The incorporation of the salts with a lubricating oil can frequently be facilitated by the simultaneous presence of a higher fatty alcohol, particularly one containing twelve or more carbon atoms, e. g. oleyl alcohol. Other hydroxylated compounds may also be present in the lubricating composition to assist in the incorporation of the salt and to modify the characteristics of the lubricant. By the use of such compounds as assistants, it is often possible to incorporate in the oil greater proportions of the salt than would otherwise be possible. An example of a suitable lubricating composition, particularly for use with cellulose acetate materials, has the following composition:
Percent Ethylene bis-(triethyl ammonium lauryl-sulphonate 7.5 Methyl cyclohexanol 7.5 Oleyl alcohol 5 White mineral oil (medium viscosity) 4O Arachis oil 40 Olive oil may be substituted for part or the Whole of the arachis oil in this composition.
When solutions of the salts in lubricating oils are required, it is often convenient to incorporate with the oil a crude preparation of the salt still containing inorganic salts formed in its production. The oil then dissolves the desired organic salt and the inorganic salts may be separated by filtration. In this way the use of a separate organic solvent, such as alcohol or acetone, in the production of the salts can be avoided.
Having described our invention, what we desire to secure by Letters Patent is:
1'. A composition suitable for lubricating cellulose acetate textile material, said composition consisting essentially of a lubricating oil, a higher fatty alcohol, and a salt of an aliphatic sulphonic acid containing 8 to 18 carbon atoms with ethylene-bis (triethyl ammonium hydroxide), the proportion of alcohol being sufficient to render the composition homogeneous and the proportion of the salt sufficient to render cellulose acetate textile material difiicult to electrify when lubricated with the composition.
2. A composition suitable for lubricating cellulose acetate textile material, said composition consisting essentially of a lubricating oil, a higher fatty alcohol of at least 12 carbon atoms, and a salt of ethylene-bis(triethyl ammonium hydroxide) with an aliphatic sulphonic acid of which the aliphatic radicle is an unsubstituted saturated hydrocarbon radicle of 8 to 18 carbon atoms, the proportion of the alcohol being sufiicient to render the composition homogeneous and the a proportion of the salt suiiicient to render cellulose acetate textile material difiicult to electrify when lubricated with the composition.
3. A composition suitable for lubricating cellulose acetate textile material, said composition comprising a lubricating oil, a higher fatty alcohol and a salt of ethylene-bis(triethyl ammonium hydroxide) with lauryl sulphonic acid, the proportion of the alcohol being sufficient to render the composition homogeneous and the proportion of the salt suflicient to render cellulose lubricated with the composition.
4. A composition suitable for lubricating cellulose acetate textile material, said composition comprisinga mixture of mineral lubricating oil and vegetable oil, oleyl alcohol and a salt of ethylene-bis(triethyl ammonium hydroxide) with lauryl sulphonic acid, the proportion of the alcohol being sufficient to render the composition homogeneous and the proportion of the salt sufficient to render cellulose acetate textile material difficult to electrify when lubricated with the composition.
HORACE FINNINGLEY OXLEY. EDWARD BOADEN THOMAS. HARRY CHARLES MURFITT.
REFERENCE S CITED UNITED STATES PATENTS Number Number Name Date Munz et al. July 12, 1932 Hueter Sept. 15, 1936 Downing et al Sept. 6, 1938 Faw Feb. 20, 1940 Cahn et al Apr. 1, 1941 Munz Feb. 3, 1942 De Groote Mar. 31, 1942 Dickey et al July 14, 1942 Iselin et a1 Aug. 25, 1942 Liberthson June 8, 1943 Dickey et al. Dec. 7, 1943 Thomas Sept. 4, 1945 FOREIGN PATENTS Country Date France Jan. 18, 1930 Addition to P. N. 645,395 Great Britain Sept. 21, 1938
Claims (1)
1. A COMPOSITION SUITABLE FOR LUBRICATING CELLULOSE ACETATE TEXTILE MATERIAL, SAID COMPOSITION CONSISTING ESSENTIALLY OF A LUBRICATING OIL, A HIGHER FATTY ALCOHOL, AND A SALT OF AN ALIPHATIC SULPHONIC ACID CONTAINING 8 TO 18 CARBON ATOMS WITH ETHYLENE-BIS (TRIETHYL AMMONIUM HYDROXIDE), THE PROPORTION OF ALCOHOL BEING SUFFICIENT TO RENDER THE COMPOSITION HOMOGENEOUS AND THE PROPORTION OF THE SALT SUFFICIENT TO RENDER CELLULOSE ACETATE TEXTILE MATERIAL DIFFICULT TO ELECTRIFY WHEN LUBRICATED WITH THE COMPOSITION.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2597947X | 1946-01-25 |
Publications (1)
Publication Number | Publication Date |
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US2597947A true US2597947A (en) | 1952-05-27 |
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ID=10911180
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US722290A Expired - Lifetime US2597947A (en) | 1946-01-25 | 1947-01-15 | Textile treating compositions |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3245905A (en) * | 1962-10-09 | 1966-04-12 | Eastman Kodak Co | Blended fibers having improved antistatic properties |
US3255107A (en) * | 1962-04-19 | 1966-06-07 | Fmc Corp | Finish composition for polyolefin fibers |
US3283005A (en) * | 1963-04-29 | 1966-11-01 | Armour & Co | p-xylylene bis quaternary ammonium compounds |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR645395A (en) * | 1926-12-11 | 1928-10-24 | Ig Farbenindustrie Ag | Humectants, detergents, emulsifiers |
FR36214E (en) * | 1927-12-15 | 1930-04-30 | Ig Farbenindustrie Ag | Humectants, detergents, emulsifiers, etc. |
US2054257A (en) * | 1933-11-17 | 1936-09-15 | Deutsche Hydrierwerke Ag | Emulsification process |
US2129264A (en) * | 1935-03-29 | 1938-09-06 | Du Pont | Nitrogen-containing organic compounds |
GB492742A (en) * | 1937-01-21 | 1938-09-21 | Du Pont | Self-emulsifying compositions and aqueous emulsions thereof |
US2191033A (en) * | 1938-06-10 | 1940-02-20 | Eastman Kodak Co | Composition for the treatment of synthetic warp yarns |
US2236515A (en) * | 1938-02-11 | 1941-04-01 | Emulsol Corp | Preparation of organic nitrogenous base salts |
US2271707A (en) * | 1937-06-24 | 1942-02-03 | Gen Aniline & Film Corp | Wetting agent |
US2278163A (en) * | 1939-05-12 | 1942-03-31 | Petrolite Corp | Aldimine salts of petroleum sulphonic acids |
US2289760A (en) * | 1938-12-21 | 1942-07-14 | Eastman Kodak Co | Yarn conditioning |
US2293826A (en) * | 1937-08-20 | 1942-08-25 | Geigy Ag J R | Treatment of textiles and other fibrous materials |
US2321496A (en) * | 1940-07-11 | 1943-06-08 | Sonneborn Sons Inc L | Polyamino petroleum sulphonates and their dehydrates |
US2336230A (en) * | 1941-08-15 | 1943-12-07 | Eastman Kodak Co | Surface-active agent |
US2384053A (en) * | 1940-06-04 | 1945-09-04 | Celanese Corp | Manufacture and use of new amine salts |
-
1947
- 1947-01-15 US US722290A patent/US2597947A/en not_active Expired - Lifetime
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR645395A (en) * | 1926-12-11 | 1928-10-24 | Ig Farbenindustrie Ag | Humectants, detergents, emulsifiers |
FR36214E (en) * | 1927-12-15 | 1930-04-30 | Ig Farbenindustrie Ag | Humectants, detergents, emulsifiers, etc. |
US1867022A (en) * | 1927-12-15 | 1932-07-12 | Ig Farbenindustrie Ag | Wetting, cleansing, and emulsifying agents and process of making same |
US2054257A (en) * | 1933-11-17 | 1936-09-15 | Deutsche Hydrierwerke Ag | Emulsification process |
US2129264A (en) * | 1935-03-29 | 1938-09-06 | Du Pont | Nitrogen-containing organic compounds |
GB492742A (en) * | 1937-01-21 | 1938-09-21 | Du Pont | Self-emulsifying compositions and aqueous emulsions thereof |
US2271707A (en) * | 1937-06-24 | 1942-02-03 | Gen Aniline & Film Corp | Wetting agent |
US2293826A (en) * | 1937-08-20 | 1942-08-25 | Geigy Ag J R | Treatment of textiles and other fibrous materials |
US2236515A (en) * | 1938-02-11 | 1941-04-01 | Emulsol Corp | Preparation of organic nitrogenous base salts |
US2191033A (en) * | 1938-06-10 | 1940-02-20 | Eastman Kodak Co | Composition for the treatment of synthetic warp yarns |
US2289760A (en) * | 1938-12-21 | 1942-07-14 | Eastman Kodak Co | Yarn conditioning |
US2278163A (en) * | 1939-05-12 | 1942-03-31 | Petrolite Corp | Aldimine salts of petroleum sulphonic acids |
US2384053A (en) * | 1940-06-04 | 1945-09-04 | Celanese Corp | Manufacture and use of new amine salts |
US2321496A (en) * | 1940-07-11 | 1943-06-08 | Sonneborn Sons Inc L | Polyamino petroleum sulphonates and their dehydrates |
US2336230A (en) * | 1941-08-15 | 1943-12-07 | Eastman Kodak Co | Surface-active agent |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3255107A (en) * | 1962-04-19 | 1966-06-07 | Fmc Corp | Finish composition for polyolefin fibers |
US3245905A (en) * | 1962-10-09 | 1966-04-12 | Eastman Kodak Co | Blended fibers having improved antistatic properties |
US3283005A (en) * | 1963-04-29 | 1966-11-01 | Armour & Co | p-xylylene bis quaternary ammonium compounds |
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