US2694688A - Antistatic compositions for textiles - Google Patents
Antistatic compositions for textiles Download PDFInfo
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- US2694688A US2694688A US339454A US33945453A US2694688A US 2694688 A US2694688 A US 2694688A US 339454 A US339454 A US 339454A US 33945453 A US33945453 A US 33945453A US 2694688 A US2694688 A US 2694688A
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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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- 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
- Y10S260/17—High polymeric, resinous, antistatic agents
- Y10S260/18—High polymeric, resinous, antistatic agents containing pentavalent nitrogen
Definitions
- This invention relates to certain polymeric alkyl sulfate quaternary ammonium salts of the acrylyloxyethylamine type and to the treatment of textiles therewith.
- composition in the form of an aqueous dispersion which comprises, in proportion, about 15 parts by weight of a watersoluble polymer of a quaternary salt of an acrylyloxyalkyltrialkylamine in which each alkyl group has from 1 to 4 carbon atoms; about 2 to 10 parts by weight of a water-soluble salt of an aliphatic alcohol sulfate having from 8 to 20 carbon atoms; about to 10 parts by weight of one or more saturated aliphatic monohydric alcohols having from 2 to 12 carbon atoms, but averaging on a weight basis of from 3.0 to 5.0 carbon atoms; about 2.0 to 20 parts by weight of a mixture of monocyclic terpene hydrocarbons; and the balance being water to give 100 parts by weight.
- the term water-soluble is used to mean that the salt is soluble in Water.
- Those of the present invention are soluble at least to the extent of about 5% by weight, at about 70 to 80 C. although the solution may be colloidal rather than a true solution. At any rate, the solution should be homogeneous and capable of dilution at the working concentration.
- the average of carbon atoms in the alcohol containing from 2 to 12 carbon atoms on a weight basis is obtained by adding the product of the number of carbon atoms in each alcohol by the gveight percent used of the alcohol, and dividing the sum
- the agents are applied to textiles by any suitable procedure which leaves on the article treated about 0.05% to about 2% or even higher under extreme conditions of the active ingredient.
- the preferred range is usually from 0.25% to 0.9% of the methylsulfate salt, or the proportionately higher equivalent of the reacted salt based on the dry weight of the textile or other material treated.
- the monocyclic terpene hydrocarbons present in the preferred dispersions are the unsaturated monocyclic hydrocarbons derived from turpentine. These are readily available on the open market in several grades and contain dipentene, terpinolene and terpinene as their primary constituents.
- the dispersions are prepared conveniently by adding an aqueous solution of the long-chain alkyl sulfate, plus the alcohols and terpenes, to an aqueous solution of the quaternary ammonium salt at room temperature. A reaction takes place between the quaternary ammonium salt and the long-chain alkyl sulfate. Some of the shortchain alkyl sulfate anions are replaced by long-chain alkyl sulfate anions, throwing out some of the quaternary compound from solution in most instances. The resulting product is, therefore, actually a dispersion of this solid in the liquid components and is made homogeneous with a fine particle size by stirring vigorously at about room temperature during the reaction.
- dispersions may be applied to the fabric by 9. padding procedure, and if desired, may be applied in conjunction with any of the ordinary crease-resistant resin finishes for textiles as will be apparent from certain of the following examples.
- resins used for this purpose are the methylol ureas, methylol melamines, their ethers and l,3-bis(hydroxymethyl)- imidazolidone. These agents impart stiffness, crease-resistance, dimensional stability and other properties to textiles.
- Example I 18.4 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 6.15 parts of mixed monocyclic terpene hydrocarbons; 4.9 parts of ethyl or isopropyl alcohol; and 3.05 parts of C3 alcohol (primarily n-octanol) are mixed to yield a clear, light yellow fluid.
- This solution is added slowly with agitation to a mixture of 50 parts of a 30% aqueous solution of poly-betamethacrylyloxyethyldiethylmethyl ammonium methylsulfate .and 17.5 parts of water. A viscous, pourable white dispersion is formed which is stable at any dilution with water.
- Example II Example I is repeated using 25 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 7.5 parts of mixed monocyclic terpene hydrocarbons; 3 parts of 95% ethyl alcohol; 3.5 grams of C6 alcohol (primarily n-hexanol); 50 parts of a 30% aqueous solution of polybeta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 11 parts of water. A similar product is produced which has comparable properties as an antistatic agent.
- Example III Example I is repeated using 32.5 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 10.0 parts of mixed monocyclic terpene hydrocarbons; 3 parts of 95% ethyl alcohol; 3 parts of n-amyl alcohol; 50 parts of a 30% aqueous solution of poly-beta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 1.5 parts of water.
- the product is a stable dispersion as 1s, and also when diluted with water to about 1%.
- Example I V Example I is repeated using parts of sodium hexadecenyl sulfate to aqueous paste); 4 parts of 95 ethyl alcohol; 2.5 parts of Ca alcohol; parts of a 30% aqueous solution of poly-beta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 28.5 parts of water.
- this product is diluted with water to 1%, the stability of the dispersion is not as good as in the preceding examples.
- Example V Similar high anti-static properties of good durability are developed when Example I is repeated using polybeta-methacrylyloxyethyltrimethyl ammonium methylsulfate. Likewise, when poly-beta-methacrylyloxyethyltriethyl ammonium ethylsulfate is substituted for the quaternary ammonium compound of Example I, the
- resulting dispersion is suitable for imparting good antistatic protection to textiles made of acetate, nylon, polyacrylonitrile and polyethylene terephthalate.
- Example VI Substitution of each of the following for sodium hexadecenyl sulfate in Example I gives a dispersion suitable for imparting attractive anti-static properties to the abovementioned hydrophobic fibers:
- Example VII A dispersion is prepared by mixing 20 parts of polybeta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate with 20 parts of asolution of 3.1 parts of sodium hexadecenyl sulfate; 11.6 parts of a monocyclic terpene (by-product of camphor manufactured from turpentine); 2.7 parts of ethyl alcohol; 1.8 parts of technical octyl alcohol; 0.8 part of decyl alcohol; 1.1 parts of isopropyl alcohol; and 12.8 parts of water.
- sion is applied to fabrics composed of nylon, polyacrylonitrile, polyethylene terephthalate and of collulose acetate by padding in such a way that 0.3% by weight of ac tive ingredient was obtained on each of the fabrics.
- the anti-static properties measured at relative humidities from 120% to as described above were all good to excelcut.
- the disper- A similar good dispersion results from reducing the amount of complex dispersing agent to 10 parts.
- the pieces of textile have a pleasing hand and satisfactory degrees of crease-resistance and dimensional stability.
- the present invention is particularly useful in reducing the anti-static properties of textile materials including fibers, yarns, threads and fabrics prepared from synthetic materials having high electrical resistance, such as those prepared from cellulose acetate, nylon, polyacrylonitrile, and polyethylene terephthalate.
- Another advantage of the present invention is that the anti-static agents may be applied simultaneously with resinous, crease-resistant materials which normally increase the static effects of the textiles so treated, but when these resins are applied with the compositions of the present invention the static effects of the resin are obviated.
- This invention also provides a direct route to an anti-static finish which is not slimy in the presence of water.
- An aqueous dispersion for imparting anti-static properties to materials which tend to accumulate an electro-static charge which comprises, in proportion, about 15 parts by weight of a water-soluble polymer of a quaternary salt of an acrylyloxyalkyltrialkylamine in which each alkyl group has from 1 to 4 carbon atoms; about 2 to 10 parts by weight of a water-soluble salt of an aliphatic alcohol sulfate having from 8 to 20 carbon atoms; about 5 to 10 parts by weight of one or more saturated, aliphatic alcohols having from 2 to 12 car -bon atoms, but averaging, on a weight basis, within the range of 3.0 to 5.0 carbon atoms; about 2.0 to 20 parts by weight of a mixture of monocyclic terpene hydrocarbons; the balance of the composition being water to give a total of parts by weight.
- composition of claim 1 having the approximate following composition in parts by weight:
- composition of claim 1 having the approximate following composition in parts by weight:
Description
Unite States Patent ANTISTATIC COMPOSITIONS FOR TEXTILES Lehman E. Hughes, New Castle, DeL, assignor to E. I. du Pont de Nemours and Company, Wilmington, Del., a corporation of Delaware No Drawing. Application February 27, 1953, Serial No. 339,454
3 Claims. (Cl. 26029.6)
This invention relates to certain polymeric alkyl sulfate quaternary ammonium salts of the acrylyloxyethylamine type and to the treatment of textiles therewith.
One disadvantage of textile fibers and particularly of fabrics prepared from synthetic hydrophobic materials. and of all textile fibers treated with conventional resin finishes, is that they tend to develop a static electrical charge. This charge is objectionable during the manufacture of the textile and in the finished garment. During manufacture the static charge on the fibers or fabric interferes with their convenient handling during spinning, reeling, Weaving and the like. Finished articles which are designed to drape like cotton or wool articles fail to do so properly due to their electrostatic charge and often cling uncomfortably to the wearer. Furthermore, such textiles tend to collect dust and lint, and the electric discharge itself is bothersome.
Many treating agents have been proposed to impart anti-static effects to textiles of this type. However, none of the proposed agents is entirely satisfactory, either because of their effectiveness or their resistance to washing and dry cleaning. Many of these anti-static agents are effectively transferred to the textile materials only with great difficulty.
It is therefore an object of this invention to provide an effective anti-static composition which is highly resistant to washing and dry cleaning. Another object is the provision of an anti-static agent which imparts a durable anti-static effect to synthetic textile fibers and fabrics. Another object is the provision of agents which may be applied by simplified treatments to the textiles rendering them substantially permanently anti-static. Other objectg will appear as the description of the invention procee s.
These and other objects are accomplished by a composition in the form of an aqueous dispersion which comprises, in proportion, about 15 parts by weight of a watersoluble polymer of a quaternary salt of an acrylyloxyalkyltrialkylamine in which each alkyl group has from 1 to 4 carbon atoms; about 2 to 10 parts by weight of a water-soluble salt of an aliphatic alcohol sulfate having from 8 to 20 carbon atoms; about to 10 parts by weight of one or more saturated aliphatic monohydric alcohols having from 2 to 12 carbon atoms, but averaging on a weight basis of from 3.0 to 5.0 carbon atoms; about 2.0 to 20 parts by weight of a mixture of monocyclic terpene hydrocarbons; and the balance being water to give 100 parts by weight.
The term water-soluble is used to mean that the salt is soluble in Water. Those of the present invention are soluble at least to the extent of about 5% by weight, at about 70 to 80 C. although the solution may be colloidal rather than a true solution. At any rate, the solution should be homogeneous and capable of dilution at the working concentration. The average of carbon atoms in the alcohol containing from 2 to 12 carbon atoms on a weight basis is obtained by adding the product of the number of carbon atoms in each alcohol by the gveight percent used of the alcohol, and dividing the sum The agents are applied to textiles by any suitable procedure which leaves on the article treated about 0.05% to about 2% or even higher under extreme conditions of the active ingredient. The preferred range is usually from 0.25% to 0.9% of the methylsulfate salt, or the proportionately higher equivalent of the reacted salt based on the dry weight of the textile or other material treated.
While many of the quaternary compounds defined above impart satisfactory anti-static properties to textiles, it has been found that the polymer of beta-methacrylyloxyethylmethyldiethyl ammonium methylsulfate, together with sodium hexadecenyl sulfate in the above combination yields exceptionally satisfactory results.
The monocyclic terpene hydrocarbons present in the preferred dispersions are the unsaturated monocyclic hydrocarbons derived from turpentine. These are readily available on the open market in several grades and contain dipentene, terpinolene and terpinene as their primary constituents.
The dispersions are prepared conveniently by adding an aqueous solution of the long-chain alkyl sulfate, plus the alcohols and terpenes, to an aqueous solution of the quaternary ammonium salt at room temperature. A reaction takes place between the quaternary ammonium salt and the long-chain alkyl sulfate. Some of the shortchain alkyl sulfate anions are replaced by long-chain alkyl sulfate anions, throwing out some of the quaternary compound from solution in most instances. The resulting product is, therefore, actually a dispersion of this solid in the liquid components and is made homogeneous with a fine particle size by stirring vigorously at about room temperature during the reaction.
These dispersions may be applied to the fabric by 9. padding procedure, and if desired, may be applied in conjunction with any of the ordinary crease-resistant resin finishes for textiles as will be apparent from certain of the following examples. Among the resins used for this purpose are the methylol ureas, methylol melamines, their ethers and l,3-bis(hydroxymethyl)- imidazolidone. These agents impart stiffness, crease-resistance, dimensional stability and other properties to textiles.
It has been found that ordinary loadings of these resins and finishes usually increase the static properties of textiles, and that the compositions of the present invention solve this particular problem very effectively.
The following examples are given by way of illustration, but it is to be understood that any of the quaternary ammonium compounds and water-soluble, long-chain sulfates fallnig within the above generic description of the invention may be substituted for any of those given in the examples with comparable results.
The agents of this invention .are applied to .textiles and tested as described in Examples 1 and II of copending application Serial No. 260,119, filed December 5, 1951.
Example I 18.4 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 6.15 parts of mixed monocyclic terpene hydrocarbons; 4.9 parts of ethyl or isopropyl alcohol; and 3.05 parts of C3 alcohol (primarily n-octanol) are mixed to yield a clear, light yellow fluid. This solution is added slowly with agitation to a mixture of 50 parts of a 30% aqueous solution of poly-betamethacrylyloxyethyldiethylmethyl ammonium methylsulfate .and 17.5 parts of water. A viscous, pourable white dispersion is formed which is stable at any dilution with water. When diluted to 1% (based on the polymer content) and padded onto nylon, polyacrylonitrile and polyethylene terephthalate fabrics, the anti-static action is excellentwhen measured as described above. This effect remains very good after repeated hot aqueous rinsing and after soap scouring.
Example II Example I is repeated using 25 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 7.5 parts of mixed monocyclic terpene hydrocarbons; 3 parts of 95% ethyl alcohol; 3.5 grams of C6 alcohol (primarily n-hexanol); 50 parts of a 30% aqueous solution of polybeta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 11 parts of water. A similar product is produced which has comparable properties as an antistatic agent.
Example III Example I is repeated using 32.5 parts of sodium hexadecenyl sulfate (25% to 30% aqueous paste); 10.0 parts of mixed monocyclic terpene hydrocarbons; 3 parts of 95% ethyl alcohol; 3 parts of n-amyl alcohol; 50 parts of a 30% aqueous solution of poly-beta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 1.5 parts of water. The product is a stable dispersion as 1s, and also when diluted with water to about 1%.
Example I V Example I is repeated using parts of sodium hexadecenyl sulfate to aqueous paste); 4 parts of 95 ethyl alcohol; 2.5 parts of Ca alcohol; parts of a 30% aqueous solution of poly-beta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate; and 28.5 parts of water. When this product is diluted with water to 1%, the stability of the dispersion is not as good as in the preceding examples.
Example V Similar high anti-static properties of good durability are developed when Example I is repeated using polybeta-methacrylyloxyethyltrimethyl ammonium methylsulfate. Likewise, when poly-beta-methacrylyloxyethyltriethyl ammonium ethylsulfate is substituted for the quaternary ammonium compound of Example I, the
resulting dispersion is suitable for imparting good antistatic protection to textiles made of acetate, nylon, polyacrylonitrile and polyethylene terephthalate.
Example VI Substitution of each of the following for sodium hexadecenyl sulfate in Example I gives a dispersion suitable for imparting attractive anti-static properties to the abovementioned hydrophobic fibers:
Example VII A dispersion is prepared by mixing 20 parts of polybeta-methacrylyloxyethyldiethylmethyl ammonium methylsulfate with 20 parts of asolution of 3.1 parts of sodium hexadecenyl sulfate; 11.6 parts of a monocyclic terpene (by-product of camphor manufactured from turpentine); 2.7 parts of ethyl alcohol; 1.8 parts of technical octyl alcohol; 0.8 part of decyl alcohol; 1.1 parts of isopropyl alcohol; and 12.8 parts of water. sion is applied to fabrics composed of nylon, polyacrylonitrile, polyethylene terephthalate and of collulose acetate by padding in such a way that 0.3% by weight of ac tive ingredient was obtained on each of the fabrics. The anti-static properties measured at relative humidities from 120% to as described above were all good to excelcut.
The disper- A similar good dispersion results from reducing the amount of complex dispersing agent to 10 parts.
In every case, both with and without the anti-static agent, the pieces of textile have a pleasing hand and satisfactory degrees of crease-resistance and dimensional stability.
The present invention is particularly useful in reducing the anti-static properties of textile materials including fibers, yarns, threads and fabrics prepared from synthetic materials having high electrical resistance, such as those prepared from cellulose acetate, nylon, polyacrylonitrile, and polyethylene terephthalate. Another advantage of the present invention is that the anti-static agents may be applied simultaneously with resinous, crease-resistant materials which normally increase the static effects of the textiles so treated, but when these resins are applied with the compositions of the present invention the static effects of the resin are obviated. This invention also provides a direct route to an anti-static finish which is not slimy in the presence of water.
It will be apparent that many widely different embodiments of the invention may be made without departing from the spirit and scope thereof, and therefore it is not intended to be limited except as indicated in the appended claims.
I claim:
1. An aqueous dispersion for imparting anti-static properties to materials which tend to accumulate an electro-static charge which comprises, in proportion, about 15 parts by weight of a water-soluble polymer of a quaternary salt of an acrylyloxyalkyltrialkylamine in which each alkyl group has from 1 to 4 carbon atoms; about 2 to 10 parts by weight of a water-soluble salt of an aliphatic alcohol sulfate having from 8 to 20 carbon atoms; about 5 to 10 parts by weight of one or more saturated, aliphatic alcohols having from 2 to 12 car -bon atoms, but averaging, on a weight basis, within the range of 3.0 to 5.0 carbon atoms; about 2.0 to 20 parts by weight of a mixture of monocyclic terpene hydrocarbons; the balance of the composition being water to give a total of parts by weight.
2. The composition of claim 1 having the approximate following composition in parts by weight:
3. The composition of claim 1 having the approximate following composition in parts by weight:
Polymeric beta methacrylyloxyethyldiethylmethyl ammonium methylsulfate 15.0 Sodium salt of octadecenyl sulfate 4.5 lithyl alcohol 5.0 An alcohol having 8 carbon atoms 3.0 Monocyclic terpene hydrocarbon mixture 6.5
Water to make 100 parts.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date Carnes Ian. 27, 1953
Claims (1)
1. AN AQUEOUS DISPERSION FOR IMPARTING ANTI-STATIC PROPERTIES TO MATERIALS WHICH TEND TO ACCUMULATE AN ELECTRO-STATIC CHARGE WHICH COMPRISES,. IN PROPORTION, ABOUT 15 PARTS BY WEIGHT OF A WATER-SOLUBLE POLYMER OF A QUATERNARY SALT OF AN ACRYLYLOXYALKYLTRIALKYLAMINE IN WHICH EACH ALKYL GROUP HAS FROM 1 TO 4 CARBON ATOMS; ABOUT 2 TO 10 PARTS BY WEIGHT OF A WATER-SOLUBLE SALT OF AN ALIPHATIC ALCOHOL SULFATE HAVING FROM 8 TO 20 CARBON ATOMS; ABOUT 5 TO 10 PARTS BY WEIGHT OF ONE OR MORE SATURATED, ALIPHATIC ALCOHOLS HAVING FROM 2 TO 12 CARBON ATOMS, BUT AVERAGING, ON A WEIGHT BASIS, WITHIN THE RANGE OF 3.0 TO 5.0 CARBON ATOMS; ABOUT 2.0 TO 20 PARTS BY WIEGHT OF A MIXTURE OF MONOCYCLIC TERPENE HYDROCARBONS; THE BALANCE OF THE COMPOSITION BEING WATER TO GIVE A TOTAL OF 100 PARTS BY WEIGHT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339454A US2694688A (en) | 1953-02-27 | 1953-02-27 | Antistatic compositions for textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339454A US2694688A (en) | 1953-02-27 | 1953-02-27 | Antistatic compositions for textiles |
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| US2694688A true US2694688A (en) | 1954-11-16 |
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| US339454A Expired - Lifetime US2694688A (en) | 1953-02-27 | 1953-02-27 | Antistatic compositions for textiles |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2824861A (en) * | 1955-05-19 | 1958-02-25 | Arnold Hoffman & Co Inc | Quaternary compounds |
| US2828221A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing cyclic t-amino groups and the resulting article |
| US2828220A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing hydroxyl groups and the resulting article |
| US2828222A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing units of acrylyl or methacrylyl dicyandiamide and the resulting article |
| US2828223A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing morpholino groups and the resulting article |
| US2828224A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing ureido groups and the resulting article |
| US2876160A (en) * | 1954-07-26 | 1959-03-03 | Corn Prod Refining Co | Starch matrix material containing imbedded material and process for preparing same |
| US2891878A (en) * | 1955-04-11 | 1959-06-23 | American Cyanamid Co | Antistatic polymeric coatings |
| US2925356A (en) * | 1956-04-24 | 1960-02-16 | Du Pont | Thermoplastic films coated with vinylidene chloride copolymer and an antistatic agent |
| DE1082004B (en) * | 1955-07-19 | 1960-05-19 | Basf Ag | Process for preventing electrostatic charging of undyed fibers, threads and products made from them |
| US3049457A (en) * | 1958-06-05 | 1962-08-14 | Carter S Ink Co | Transfer paper |
| US3248352A (en) * | 1961-09-08 | 1966-04-26 | Du Pont | Polymeric materials containing oxidized amine radicals and stable, aqueous, water-repellency compositions containing the same |
| US3420703A (en) * | 1964-05-30 | 1969-01-07 | Bayer Ag | Process for treating a textile material with an aqueous antistatic and handle-improving composition and the aqueous treating composition |
| US3563375A (en) * | 1967-08-08 | 1971-02-16 | Auby Prod Chim | Method of selectively separating solid particles by electrostatic sorting in fluidized bed |
| US3973901A (en) * | 1973-12-06 | 1976-08-10 | National Starch And Chemical Corporation | Hair coloring composition containing a water-soluble cationic polymer and a process for use thereof |
| US4009256A (en) * | 1973-11-19 | 1977-02-22 | National Starch And Chemical Corporation | Novel shampoo composition containing a water-soluble cationic polymer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626786A (en) * | 1947-05-05 | 1953-01-27 | Leonard D Mcglothlin | Automatic consistency control means |
-
1953
- 1953-02-27 US US339454A patent/US2694688A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626786A (en) * | 1947-05-05 | 1953-01-27 | Leonard D Mcglothlin | Automatic consistency control means |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876160A (en) * | 1954-07-26 | 1959-03-03 | Corn Prod Refining Co | Starch matrix material containing imbedded material and process for preparing same |
| US2828221A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing cyclic t-amino groups and the resulting article |
| US2828220A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing hydroxyl groups and the resulting article |
| US2828222A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing units of acrylyl or methacrylyl dicyandiamide and the resulting article |
| US2828223A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing morpholino groups and the resulting article |
| US2828224A (en) * | 1955-03-21 | 1958-03-25 | Rohm & Haas | Method of coating leather with polymers containing ureido groups and the resulting article |
| US2891878A (en) * | 1955-04-11 | 1959-06-23 | American Cyanamid Co | Antistatic polymeric coatings |
| US2824861A (en) * | 1955-05-19 | 1958-02-25 | Arnold Hoffman & Co Inc | Quaternary compounds |
| DE1082004B (en) * | 1955-07-19 | 1960-05-19 | Basf Ag | Process for preventing electrostatic charging of undyed fibers, threads and products made from them |
| US2925356A (en) * | 1956-04-24 | 1960-02-16 | Du Pont | Thermoplastic films coated with vinylidene chloride copolymer and an antistatic agent |
| US3049457A (en) * | 1958-06-05 | 1962-08-14 | Carter S Ink Co | Transfer paper |
| US3248352A (en) * | 1961-09-08 | 1966-04-26 | Du Pont | Polymeric materials containing oxidized amine radicals and stable, aqueous, water-repellency compositions containing the same |
| US3420703A (en) * | 1964-05-30 | 1969-01-07 | Bayer Ag | Process for treating a textile material with an aqueous antistatic and handle-improving composition and the aqueous treating composition |
| US3563375A (en) * | 1967-08-08 | 1971-02-16 | Auby Prod Chim | Method of selectively separating solid particles by electrostatic sorting in fluidized bed |
| US4009256A (en) * | 1973-11-19 | 1977-02-22 | National Starch And Chemical Corporation | Novel shampoo composition containing a water-soluble cationic polymer |
| US3973901A (en) * | 1973-12-06 | 1976-08-10 | National Starch And Chemical Corporation | Hair coloring composition containing a water-soluble cationic polymer and a process for use thereof |
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