US2180436A - Textile materials - Google Patents
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- US2180436A US2180436A US171065A US17106537A US2180436A US 2180436 A US2180436 A US 2180436A US 171065 A US171065 A US 171065A US 17106537 A US17106537 A US 17106537A US 2180436 A US2180436 A US 2180436A
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- alkali
- cellulose
- polyglycol
- finish
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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
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
-
- 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
-
- 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
- Y10T428/2965—Cellulosic
Definitions
- This invention relates to the preparation of an improved finish for textile materials and to the application of that finish to yarns, fibers, threads, fabrics, etc. containing organic derivatives of cellulose.
- the invention relates more particularly to the preparation of an antistatic finish for textile materials which contains an alkali polyglycol sulphonate.
- An object of the invention is the preparation of a class of compounds adapted for use in connection with textile materials, films or foils made of or containing an organic derivative of cellulose.
- the materials of this class may be em- .ployed in yarn lubricants, anti-static textile finishes, dye pastes, wetting out agents, etc.
- textile finish includes any or all of the preparations normally applied to textile materials at one time or another in their course of manufacture from spinning' of the filaments to the finished fabrics.
- Another object of this invention is the application of this class of compounds to textile materials or other articles containing organic de- 5 rivatives of cellulose. Other objects of this invention will appear from the following detailed description.
- alkali polyglycol sulphonates are 5 especially suitable as aids in anti-static finishes, wetting-out agents and as dispersing mediums in connection with the processing of organic derivative of cellulose textile materials. These compounds have the advantage over those formerly 10 used in that they may be employed with hard Water as they form soluble compounds with the alkali-earth metals. Further advantages of the alkali polyglycol sulphonates are that they are stable to heat, acids and alkali; neither breaking 5 down to undesirable compounds nor effecting undesirable changes in the organic derivative of cellulose. Moreover, I have found an economic v method of preparing the alkali polyglycol sulphonates. 20
- I prepare a1- kali polyglycol sulphonates by reacting an alkali bisulphite with a cyclic ether, there being more than one mole of cyclic ether present. After one mole of the cyclic ether has reacted with the alkali bisulphite an alkali hydroxide may be added to the reaction to act as a catalyst in promoting the reaction of the remaining cyclic ether.
- the alkali bisulphite is preferably sodium or potassium bisulphite, while any cyclic ether may be employed.
- cyclic ethers which may be used in accordance with my invention are ethylene oxide, propylene oxide, trimethylene oxide, butylene oxide and the isomers and homologues of these ethers.
- three or more moles, say 3 to 8 moles, of the cyclic ether are reacted with one mole of the alkali bisulphite.
- the fatty acid esters or fatty ethers of the alkali polyglycol sulphonates should be used.
- alkali polyglycol sulphonate is to be construed as including within its scope the alkali salts formed by the reaction of a bisulphite with acyclic ether, and the fatty ether or fatty acid ester derivatives of these compounds.
- alkali polyglycol sulphonates are relatively stable compounds that do not break down upon storage,'contact with acids, bases or when heated up to their boiling point and as they are exceptionally suitable as wetting-out compounds, antin static materials and may be made to have good lubricating properties, they may be employed in connection with all types of textile fibers. They may be employed in the carding, spinning and weaving "of cotton, wool, linen, etc. or in the twisting, packaging and weaving of silk, and as a wetting-out agent in the dyeing of all textile materials. They are of particular importance in connection with textile materials made of or containing an organic derivative of cellulose as many of the present textile finishes are injurious to these materials.
- the textile material may be made of any suitable organic derivative of cellulose such as the organic esters of cellulose and cellulose ethers.
- suitable organic derivative of cellulose such as the organic esters of cellulose and cellulose ethers.
- the organic esters of cellulose are cellulose acetate, cellulose formate, cellulose propionate and cellulose butyrate, while examples of the cellulose ethers are ethyl cellulose, methyl cellulose and benzyl cellulose.
- Example I 300 parts of sodium bisulphite are dissolved in 500 parts of water. This solution is placed in a reflux still equipped with a stirrer and inlet connection. More than 250 parts liquid ethylene oxide are allowed to evaporate and enter the refiux still at room temperature. The vapors of the ethylene oxide are passed into the sodium bisulphite solution while the solution is stirred. The temperature of the solution gradually rises to between 70 and C. and remains at this point until all the ethylene oxide has been introduced into the solution. The water running in the reflux condenser is maintained at about 10 C. or sufiiciently low to condense most of the ethylene oxide which escapes absorption and returns it to the sodium bisulphite solution.
- HO-CHz-CH2-OCH2CHz-SO4Na formed by the action of sulfuric acid on the polyglycols. These compounds are very unstable, hydrolyzing in water and being easily decomposed by alkalies.
- the alkali polyglycol sulphonates are exceptionally suited as anti-static finishes on textile materials containing organic derivatives of cellulose.
- organic derivative of cellulose say cellulose acetate
- woolen system or the cotton system much difliculty has been encountered due to static electricity being retained by the fibers which prevents uniform 40 carding and drafting operations. It becomes necessary to treat these staple fibers so that they may become conductors of electricity in order to produce uniform yarns and threads.
- Example II Cellulose acetate staple fibers are treated with a 1% finish comprising parts of alkali polyglycol sulphonate and 5 parts sulphated oleyl alcohol, lauryl alcohol or other sulphated alcohol containing more than four carbon atoms.
- the so sulphonated or sulphated fatty alcohols are not a necessary addition to the finish but may be added to increase the lubricative property of the finish.
- This finish is applied to the fibers by immersing them in a 2% aqueous solution of the 65 same and then driving off the water by any suitable method of extraction.
- the fibers are sumciently lubricated for both the cotton method and woolen method of forming yarns and are made sufficiently anti-static to form uniform threads 70 or yarns. 1
- the percentage of finish applied may vary within wide limits from 1% as stated above.
- the fibers may be finished with from 0.5% to 10% on the weight of the fiber of the ma 5 terial.
- yarns of continuous filaments, staplized fiber or spun stable fiber are treated with the finish it is preferable to use approximately 3 of the finish on the weight of the yarn.
- alkali polyglycol sulphonate other oily materials may be added to it such as vegetable oil, mineral oil or the sulphated or sulphonated vegetable oils, alcohols, etc., or the lubricative properties of the alkali polyglycol sulphonate may be increased by forming the fatty acid esters or fatty ethers of the same such as the reaction of the alkali polyglycol sulphonate with stearic acid, oleic acid and the like. If desired up to 50% on the weight of complete finish of the other oily materials may be added to the alkali polyglycol sulphonate.
- the alkali polyglycol sulphonate may also be employed as the dispersing or wetting-out agent in dye pastes.
- the alkali polyglycol sulphonate and a dye may be ground together into the form of a paste. Turkey red oil or other dispersing agents may or may not be added to the paste.
- These pastes when added to a dye bath are readily dispersed.
- the same may be employed to form pastes used in printing textiles, such as .a printing paste containing dye and/or discharge reagents which pastes also may contain starch, albumin, glycerine or glycol.
- a finish for textile materials containing an organic derivative of cellulose comprising an alkali polyglycol sulphonate.
- a finish for textile materials containing cellulose acetate comprising an alkali polygylcol sulphonate.
- a finish for textile materials containing an organic derivative of cellulose comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite.
- a finish for textile materials containing cellulose acetate comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite.
- a finish for textile materials containing cellulose acetate comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite and a sulphated alcohol contain ing more than four carbon atoms.
- An anti-static finish for textile materials containing cellulose acetate comprising an alkali polyglycol sulphonate and a sulphonated oil.
- Textile materials comprising an organic derivative of cellulose and an alkali polyglycol sulphonate.
- Textile materials comprising cellulose acetate and an alkali polyglycol sulphonate.
- An anti-static finish for textile vmaterials containing an organic derivative of cellulose, an alkali polyglycol sulphonate and a sulphated alcohol containing more than four carbon atoms.
- An anti-static finish for textile materials containing cellulose acetate, an alkali polyglycol sulphonate and a sulphated alcohol containing more than four carbon atoms.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Nov. 21, 1939 PATENT OFFICE TEXTILE MATERIALS Richard R. Sitzler, Cumberland, Md., assignor to Celanese Corporation of America, a corporation of Delaware N Drawing. Application October 26, 1937, Serial No. 171,065
18 Claims.
This invention relates to the preparation of an improved finish for textile materials and to the application of that finish to yarns, fibers, threads, fabrics, etc. containing organic derivatives of cellulose. The invention relates more particularly to the preparation of an antistatic finish for textile materials which contains an alkali polyglycol sulphonate.
An object of the invention is the preparation of a class of compounds adapted for use in connection with textile materials, films or foils made of or containing an organic derivative of cellulose. The materials of this class may be em- .ployed in yarn lubricants, anti-static textile finishes, dye pastes, wetting out agents, etc. For the purpose of describing this invention and in the appended claims, the term textile finish includes any or all of the preparations normally applied to textile materials at one time or another in their course of manufacture from spinning' of the filaments to the finished fabrics. Another object of this invention is the application of this class of compounds to textile materials or other articles containing organic de- 5 rivatives of cellulose. Other objects of this invention will appear from the following detailed description.
Many organic sodium salts have been used in finishes and as wetting-out agents in the textile 30 industry, among which may be named the sodium salt of sulphated eleyl alcohol, the sodium salt of sulphonated olive oil, etc., which may or may not contain sperm oil, fatty acids, etc. These salts must be used with soft water for, 5 when they are used with hard water, alkali-earth metal compounds which are insoluble are formed. The formation of these insoluble compounds reduces the beneficial effect of the finishysince they form a solid material which clogs filters, 40 pump systems and wicks. When such compounds are applied by padding methods they form an undesirable precipitate on the dressing of the padding mangle and when employed with dyes the solid insoluble particles make for un- 45 even dyeing and produce specks on the material. Many other types of anti-static materials and finishes employed in the general textile industry cannot be employed on organic derivative of cellulose materials since these materials by- 50 drolyze or saponify'in the presence of acids or alkalies to form compounds which effect the stability, delustering properties, ageing properties, dye aflinity, etc. of the organic derivative of cellulose. Many textile finishes themselves 55 break down by saponification or hydrolyzation into compounds which adversely affect the organic derivative of cellulose materials. For instance, the sodium salt of sulphonated olive oil is broken down in the presence of acids.
I have found alkali polyglycol sulphonates are 5 especially suitable as aids in anti-static finishes, wetting-out agents and as dispersing mediums in connection with the processing of organic derivative of cellulose textile materials. These compounds have the advantage over those formerly 10 used in that they may be employed with hard Water as they form soluble compounds with the alkali-earth metals. Further advantages of the alkali polyglycol sulphonates are that they are stable to heat, acids and alkali; neither breaking 5 down to undesirable compounds nor effecting undesirable changes in the organic derivative of cellulose. Moreover, I have found an economic v method of preparing the alkali polyglycol sulphonates. 20
In accordance with'my invention I prepare a1- kali polyglycol sulphonates by reacting an alkali bisulphite with a cyclic ether, there being more than one mole of cyclic ether present. After one mole of the cyclic ether has reacted with the alkali bisulphite an alkali hydroxide may be added to the reaction to act as a catalyst in promoting the reaction of the remaining cyclic ether. The alkali bisulphite is preferably sodium or potassium bisulphite, while any cyclic ether may be employed. Examples of cyclic ethers which may be used in accordance with my invention are ethylene oxide, propylene oxide, trimethylene oxide, butylene oxide and the isomers and homologues of these ethers. Preferably three or more moles, say 3 to 8 moles, of the cyclic ether are reacted with one mole of the alkali bisulphite.
If a more lubricative material is desired, the fatty acid esters or fatty ethers of the alkali polyglycol sulphonates should be used. For the purpose of this specification and in the appended claims, the term alkali polyglycol sulphonate is to be construed as including within its scope the alkali salts formed by the reaction of a bisulphite with acyclic ether, and the fatty ether or fatty acid ester derivatives of these compounds.
As alkali polyglycol sulphonates are relatively stable compounds that do not break down upon storage,'contact with acids, bases or when heated up to their boiling point and as they are exceptionally suitable as wetting-out compounds, antin static materials and may be made to have good lubricating properties, they may be employed in connection with all types of textile fibers. They may be employed in the carding, spinning and weaving "of cotton, wool, linen, etc. or in the twisting, packaging and weaving of silk, and as a wetting-out agent in the dyeing of all textile materials. They are of particular importance in connection with textile materials made of or containing an organic derivative of cellulose as many of the present textile finishes are injurious to these materials. The textile material may be made of any suitable organic derivative of cellulose such as the organic esters of cellulose and cellulose ethers. Examples of the organic esters of cellulose are cellulose acetate, cellulose formate, cellulose propionate and cellulose butyrate, while examples of the cellulose ethers are ethyl cellulose, methyl cellulose and benzyl cellulose.
The following example illustrates the general method of preparing phonate:
Example I 300 parts of sodium bisulphite are dissolved in 500 parts of water. This solution is placed in a reflux still equipped with a stirrer and inlet connection. More than 250 parts liquid ethylene oxide are allowed to evaporate and enter the refiux still at room temperature. The vapors of the ethylene oxide are passed into the sodium bisulphite solution while the solution is stirred. The temperature of the solution gradually rises to between 70 and C. and remains at this point until all the ethylene oxide has been introduced into the solution. The water running in the reflux condenser is maintained at about 10 C. or sufiiciently low to condense most of the ethylene oxide which escapes absorption and returns it to the sodium bisulphite solution. By this method the first two or three moles of ethylene oxide combine with the sodium bisulphite very'readily but the reaction slows down considerably when attempts are made to add four or more moles of the oxide. For the preparation of these longer chain compounds an alkali catalyst, say sodium hydroxide, is employed. Care is taken, however, not to add the catalyst until after the first mole of ethylene oxide has been reacted with the cyclic ether, in order to prevent the alkali from combining with the sodium bisulphite and thus remove both the sulphite and the catalyst from the reaction. It is not necessary to weigh the ethylene oxide-sodium bi-bisulphite' mixture to determine when the catalyst should be added as the reaction mixture turns slightly brown and the pH value changes from slightly acid to neutral or slightly alkaline after the first mole of oxide has combined with the bisulphite.
After the reaction has been carried to the desired extent, say the combining of 3 to 8 or more moles of the cyclic ether with one of the sulphite, enough acid, say boric acid, acetic acid or sulphuric acid, is added to neutralize the alkali hydroxide used as catalyst. The mixture is then heated to slightly above 100 C. to drive off the water present in the reaction mixture.
The equation for the reaction of one mole of ethylene oxide and one mole of sodium bisulphite is as follows:
When additional moles of ethylene oxide are added, I consider that compounds with the followthe alkali polyglycol su1-' ing structures are formed: Two moles of ethylene oxide-- HO-CHz-CH2-OCH2CH2-SO3Na Five moles of ethylene oxide- 5 HOCH2(CHzO-CH2) 4CH2--SOaNa 'It might be argued that the compounds formed with large amounts of ethylene oxide are merely mixtures of polyglycols and sodium hydroxy 10 ethane sulphonate. I do not consider that this is the case for the following reasons:
These compounds should not be confused with 25 polyglycol sulfates, i. e.
HO-CHz-CH2-OCH2CHz-SO4Na formed by the action of sulfuric acid on the polyglycols. These compounds are very unstable, hydrolyzing in water and being easily decomposed by alkalies. I
The alkali polyglycol sulphonates are exceptionally suited as anti-static finishes on textile materials containing organic derivatives of cellulose. In the production of yarns or threads from 35 fibers of organic derivative of cellulose, say cellulose acetate, by methods employing the woolen system or the cotton system, much difliculty has been encountered due to static electricity being retained by the fibers which prevents uniform 40 carding and drafting operations. It becomes necessary to treat these staple fibers so that they may become conductors of electricity in order to produce uniform yarns and threads. I have found that if staple fibers of cellulose acetate or 45 other organic derivative of cellulose are treated with alkali-polyglycol sulphonates the fibers are sumciently lubricated .for both the cotton and woolen method of forming yarns and the fibers are sufiiciently anti-static to form uniform yarns. 50
As an illustration of the application of an alkalipolyglycol sulphonate to staple fibers the following example is given:
Example II Cellulose acetate staple fibers are treated with a 1% finish comprising parts of alkali polyglycol sulphonate and 5 parts sulphated oleyl alcohol, lauryl alcohol or other sulphated alcohol containing more than four carbon atoms. The so sulphonated or sulphated fatty alcohols are not a necessary addition to the finish but may be added to increase the lubricative property of the finish. This finish is applied to the fibers by immersing them in a 2% aqueous solution of the 65 same and then driving off the water by any suitable method of extraction. The fibers are sumciently lubricated for both the cotton method and woolen method of forming yarns and are made sufficiently anti-static to form uniform threads 70 or yarns. 1
Obviously the percentage of finish applied may vary within wide limits from 1% as stated above. For instance, the fibers may be finished with from 0.5% to 10% on the weight of the fiber of the ma 5 terial. When yarns of continuous filaments, staplized fiber or spun stable fiber are treated with the finish it is preferable to use approximately 3 of the finish on the weight of the yarn. To increase the lubricative property of the alkali polyglycol sulphonate other oily materials may be added to it such as vegetable oil, mineral oil or the sulphated or sulphonated vegetable oils, alcohols, etc., or the lubricative properties of the alkali polyglycol sulphonate may be increased by forming the fatty acid esters or fatty ethers of the same such as the reaction of the alkali polyglycol sulphonate with stearic acid, oleic acid and the like. If desired up to 50% on the weight of complete finish of the other oily materials may be added to the alkali polyglycol sulphonate.
The alkali polyglycol sulphonate, besides being employed as an anti-static finish on yarns or fibers, may also be employed as the dispersing or wetting-out agent in dye pastes. For instance, the alkali polyglycol sulphonate and a dye may be ground together into the form of a paste. Turkey red oil or other dispersing agents may or may not be added to the paste. These pastes when added to a dye bath are readily dispersed. Instead of being employed in the formation of pastes to be added. to aqueous dye baths, the same may be employed to form pastes used in printing textiles, such as .a printing paste containing dye and/or discharge reagents which pastes also may contain starch, albumin, glycerine or glycol.
It is to be understood that the foregoing detailed description is merely given by way of illustration and that many variations may be made therein without departing from the spirit of my invention.
Having described my invention, what I desire to secure by Letters Patent is:
1. In a method of preparing a finish for textile materials, the step of reacting one mole of alkali .bisulphite with more than one mole of a cycle ether.
2. In a method of preparing a finish for textile materials, the steps of reacting one mole of alkali bisulphite with slightly more than one mole of a cyclic ether, adding an alkali hydroxide to the reaction as a catalyst and effecting the reaction of more cyclic ether.
3. In a method of preparing a finish for textile materials, the step of reacting one mole of sodium bisulphite with more than one mole of a cyclic ether.
4. In a method of preparing a finish for textile materials, the step of reacting one mole of alkali bisulphite with more than one mole of ethylene.
oxide.
5. In a method of preparing a finishfor textile materials, the step of reacting one mole of sodium bisulphite with more than one mole of ethylene oxide.
6. In a method of preparing a finish for textile materials, the steps of reacting one mole of alkali bisulphite with slightly more than one mole of ethylene oxide, adding an alkali hydroxide to the reactionas a catalyst and effecting the reaction of more ethylene oxide.
7. In a method of preparing a finish for textile materials, thesteps of reacting one mole of sodium bisulphite with more than one mole of a cyclic ether, and esterifying-the reaction product with a fatty acid.
8. A finish for textile materials containing an organic derivative of cellulose comprising an alkali polyglycol sulphonate.
9. A finish for textile materials containing cellulose acetate comprising an alkali polygylcol sulphonate.
10. A finish for textile materials containing an organic derivative of cellulose comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite.
11. A finish for textile materials containing cellulose acetate comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite.
12. A finish for textile materials containing cellulose acetate comprising an alkali polyglycol sulphonate formed by the reaction of more than one mole of cyclic ether with one mole of an alkali bisulphite and a sulphated alcohol contain ing more than four carbon atoms.
13. An anti-static finish for textile materials containing anorganic derivative of cellulose, comprising an alkali polyglycol sulphonate and a sulphonated oil. v
14. An anti-static finish for textile materials containing cellulose acetate, comprising an alkali polyglycol sulphonate and a sulphonated oil.
15. Textile materials comprising an organic derivative of cellulose and an alkali polyglycol sulphonate.
16. Textile materials comprising cellulose acetate and an alkali polyglycol sulphonate.
17. An anti-static finish for textile vmaterials containing an organic derivative of cellulose, an alkali polyglycol sulphonate and a sulphated alcohol containing more than four carbon atoms.
18. An anti-static finish for textile materials containing cellulose acetate, an alkali polyglycol sulphonate and a sulphated alcohol containing more than four carbon atoms.
RICHARD R. SITZLER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US171065A US2180436A (en) | 1937-10-26 | 1937-10-26 | Textile materials |
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US171065A US2180436A (en) | 1937-10-26 | 1937-10-26 | Textile materials |
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US2180436A true US2180436A (en) | 1939-11-21 |
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US171065A Expired - Lifetime US2180436A (en) | 1937-10-26 | 1937-10-26 | Textile materials |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2790764A (en) * | 1953-03-13 | 1957-04-30 | Bohme Fettchemie Gmbh | Composition for preventing textile materials from becoming electrically charged |
-
1937
- 1937-10-26 US US171065A patent/US2180436A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2790764A (en) * | 1953-03-13 | 1957-04-30 | Bohme Fettchemie Gmbh | Composition for preventing textile materials from becoming electrically charged |
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