US2294379A - Surface-active incrustation inhibitor - Google Patents
Surface-active incrustation inhibitor Download PDFInfo
- Publication number
- US2294379A US2294379A US316278A US31627840A US2294379A US 2294379 A US2294379 A US 2294379A US 316278 A US316278 A US 316278A US 31627840 A US31627840 A US 31627840A US 2294379 A US2294379 A US 2294379A
- Authority
- US
- United States
- Prior art keywords
- glucyl
- active
- cation
- viscose
- acid
- 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
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
Definitions
- R1 is a higher aliphatic radical having 8 or more carbon atoms
- R: and Ra represent lower aliphatic and/or aromatic radicals or hydrogen atoms
- X represents an atom of nitrogen, phosphorus, arsenic or antimony
- Ac represents an innocuous anion, such as an OH group or a negative acid radical.
- n, X, R1 and R have the foregoing significance.
- Cation-active compounds are surface-active compounds which carry in the cation a hydrocarbon chain 8 or more carbon atoms. They are used in neutral salt, alkaline and acidic aqueous solutions, and also in hard water.
- anion-active compounds are surface-active compounds which carry in the anion a more or less extended hydrocarbon chain. They fiocculate in neutral salt. alkaline and acidic aqueous solutions, and also in hard water. Common soaps, etc., are anionactive compounds, and thus are unable to prevent the incrustation of spinnerets and spinneret orifices.
- Incrustation inhibitors in accordanc with the present invention, may be prepared from amines.
- phosphines, arsines and stibines derived from 'monosaccharide of the ketose or aldose type containing 5 or 6 carbon atoms.
- These sugar amines, phosphines, arsines and stibines may be prepared from glucose, galactose, fructose. Xylose, arabinose, mannose, rhamnose, ribose, talose, etc.
- Acid addition compounds may be prepared from these sugar amines, phosphines, arsines and stibines by treating them with inorganic or organic acids, such as hydrochloric acid, sulphuric acid, acetic acid, formic acid, etc. For conversion into cation-active'compounds these sugar amines, phosphines, arsines and stibines are reacted with an alkyl halide containing 8 or more carbon atoms. Acid addition compounds may be formed from these secondary, cation-active amines, phosphines, arsines and stibines.
- cationactive secondary vases may also be reacted with lower aliphatic or aromatic halides or sulphates for the production of cation-active, tertiary bases from which acid addition products may be formed.
- the cation-active, tertiary bases may finally be reacted with an aliphatic or aromaticpreferably low-molecularhalide or sulphate to form cation-active, quaternary ammonium, phosphonium, arsonium or stibonium salts which may be converted into corresponding cation-active, quaternary bases.
- the following table depicts a number of compounds which may be used as incrustation inhibitors:
- R1 is a higher aliphatic radical having 8 or more carbon atoms
- X represents an atom of nitrogen, phosphorous, arsenic or antimony, and acid addition products thereof:
- R1 n( H)niHn )-2' X in which n is 5 or 6,.R1 is a higher aliphatic radical having 8 or more carbon atoms, R2 represents a lower aliphatic or aromatic radical, and X represents an atom of nitrogen, phosphorus, arsenic or antimony, and acid addition products thereof.
- n is 5 or '6
- R1 is a higher aliphatic radical having 8 or more carbon atoms
- R: and Ra represent lower aliphatic and/or aromatic radicals
- X represents an atom of nitrogen, phosphorus, arsenic or antimony
- Ac represents an innocuous anion, such as an OH group or a negative acid radical.
- Example I A mixture 01! 180 parts oi. ethylene cblorhydrin, 125 parts of potassium hydroxide, I parts oi N-dodecyl-glucyl-amine, and 5000 parts of methyl alcohol is refluxed at a moderate temperature for a iew hours. The solution is filtered to remove inorganic salts and the filtrate evaporated to dryness. About 0.3 to 2.0 grams oi the waxy N-dodecyl-N-hydroxy-ethyl glucyl amine are added to about one liter of a viscose solution of conventional concentration and maturity.
- a spinneret into a conventional spin bath, such as, for example, a glucose bath, a magnesium-bath, etc.
- a conventional spin bath such as, for example, a glucose bath, a magnesium-bath, etc.
- the spinnerets and theirorifices remain clean on prolonged spinning.
- Other cation-active compounds having the structure set forth above, may be used with equal success.
- Example II- parts of N-octadecyl-glucyl-amine and 5000 parts of methyl alcohol is' refluxed to form octadecyl-glycyl-amine, propanediol.
- a conventional viscose solution is extruded through fine orifices of precious metal spinnerets into an acid spin bath, containing for example, sulphuric acid, sodium sulphate, ammonium sulphate and zinc sulphate and about 0.3 to 5.0 grams per liter of waxy N-octadecyl-glucyl-amine, propanediol. Spinning irregularities and dliilculties are substantially overcome.
- N-octadecylglucyl-amino, propanediol may be replaced by any other sufliciently soluble and stable ammonium, phosphorus, sulphur, arsenic and antimony derivative of a monosaccharide having the general structure set forth above.
- Example III A solution of about 150 parts of N-methyl-N- glucyl cetyl amine in about 500 parts of ethyl alcohol is boiled under reflux with about 150 parts of ethyl iodide for several hours. After revolving-excess ethyl iodide and alcohol by evaporation, N-methyl-ethyl-N-glucyl cetyl ammonium iodide is obtained as a brownish mass. This compound or any other one set forth above is added to both the viscose solution and the spin bath. The formation of zinc rings and sulphur craters is substantially overcome.
- An acid viscose spin bath for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having .the structure:
- n is a number selected from the group consisting 01. 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R: and R: represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen
- Ac represents a substituent selected from the group consisting of OH and negative acid radicals, whereby incrustation of the spinneret during the spinning operation is substantially inhibited.
- An acid viscose spin bath for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having the structure:
- n is a number selected from the group consisting of 5 and 6
- R1 is a higher aliphatic radicalhaving at least 8 carbon atoms
- Ri-and R3 represent lower aliphatic radicals
- Ac represents a substituent selected from the group consisting of 0H and negative acid. radicals, whereby incrustation oi the spinneret during the spinning operation is substantially inhibited.
- An acid viscose spin bath for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having the structure:
- n is a number selected irom the group consisting of 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R: and Rs represent lower aromatic radicals
- Ac represents a substituent selected from the group consisting of OH and negative acid radicals, whereby incrustationoi the spinneret during the spinning operation is substantially inhibited.
- An acid viscose spin bath for coagulating viscose filaments therein, containing a dissolved
- n is a number selected from the group consisting of 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R: and R3 represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen
- Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
- n is a number selected from the group consisting of 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R: and R3 represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen
- Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
- n is a number selected from the group consisting of 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R2 and Ra represent lower aliphatic radicals
- Ac represents a substituent selected from the group consisting of 0H and negative acid radicals.
- n is a number selected from the group consisting of 5 and 6
- R1 is a higher aliphatic radical having at least 8 carbon atoms
- R: and R3 represent lower aromatic radicals
- Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
- n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and
- R3 represent hydrogen, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
Description
Patented Sept. 1, 1942 SURFACE-ACTIVE INCBUSTATION mnmrroa Rudolph S. Bley, MilliganCollege, Tenn, assignor to North American Rayon Corporation, New York, N. Y., a corporation Delaware No Drawing.
Original application October I,
1938, Serial No. 233,826. Divided and this IP- plication January 29, 1940, Serial No. 316,278
11 Claims.
This is a division of my application Serial No. 233,826, filed October 7, 1938.
In the manufacture of cellulosic products, such as filaments, threads and the like, a viscosesolution is continuously extruded through the minute orifices of a spinneret into a coagulating or setting bath. However, since the introduction of the viscose process great troubles have been and are still experienced as far as continuous spinning is concerned due to impurities, such as for example, precipitated cellulose particles, sulphur and resin particles, zinc compounds, etc., present in either the viscose solution or the spin bath. These impurities gradually contaminate the spinnerets, clog and reduce the widths of the spinneret orifices with the result that filaments of uneven thickness are obtained. If contamination proceeds the individual filament start to tear and occasion interruption of the spinning process.
I have found that contamination of spinnerets and clogging of spinneret orifices may be substantially overcome by spinning viscose solutions in the presence of cation-active monosaccharide derivatives or acid addition products thereof having the general structure:
in which n is 5 or 6, R1 is a higher aliphatic radical having 8 or more carbon atoms, R: and Ra represent lower aliphatic and/or aromatic radicals or hydrogen atoms, X represents an atom of nitrogen, phosphorus, arsenic or antimony, and Ac represents an innocuous anion, such as an OH group or a negative acid radical.
Although these compounds may be obtained in a variety of ways, they are most readily obtained by reacting an aliphatic or aromatic halide having less than 8 carbon atoms with an amine, phosphine, arsine or stibine having the structure:
in which n, X, R1 and R: have the foregoing significance.
Cation-active compounds are surface-active compounds which carry in the cation a hydrocarbon chain 8 or more carbon atoms. They are used in neutral salt, alkaline and acidic aqueous solutions, and also in hard water. In contradis tinction to cation-active compounds, anion-active compounds are surface-active compounds which carry in the anion a more or less extended hydrocarbon chain. They fiocculate in neutral salt. alkaline and acidic aqueous solutions, and also in hard water. Common soaps, etc., are anionactive compounds, and thus are unable to prevent the incrustation of spinnerets and spinneret orifices.
Incrustation inhibitors, in accordanc with the present invention, may be prepared from amines. phosphines, arsines and stibines derived from 'monosaccharide of the ketose or aldose type containing 5 or 6 carbon atoms. These sugar amines, phosphines, arsines and stibines may be prepared from glucose, galactose, fructose. Xylose, arabinose, mannose, rhamnose, ribose, talose, etc.
Acid addition compounds may be prepared from these sugar amines, phosphines, arsines and stibines by treating them with inorganic or organic acids, such as hydrochloric acid, sulphuric acid, acetic acid, formic acid, etc. For conversion into cation-active'compounds these sugar amines, phosphines, arsines and stibines are reacted with an alkyl halide containing 8 or more carbon atoms. Acid addition compounds may be formed from these secondary, cation-active amines, phosphines, arsines and stibines. These cationactive secondary vases may also be reacted with lower aliphatic or aromatic halides or sulphates for the production of cation-active, tertiary bases from which acid addition products may be formed. The cation-active, tertiary bases may finally be reacted with an aliphatic or aromaticpreferably low-molecularhalide or sulphate to form cation-active, quaternary ammonium, phosphonium, arsonium or stibonium salts which may be converted into corresponding cation-active, quaternary bases. The following table depicts a number of compounds which may be used as incrustation inhibitors:
Table 1. Cation-active, secondary bases having the structure:
Bi 0. 0H)...H..;-x
- m which n is s or 6, R1 is a higher aliphatic radical having 8 or more carbon atoms, R: repreparticularly advantageous because they may be sents hydrogen, and X represents an atom of nitrogen, phosphorous, arsenic or antimony, and acid addition products thereof:
N-octyl glucyl amine N-nonyl glucyl amine N-decyl glucyl amine N-tetradecyl glucyl amine Q N-cetyl glucyl amine N-dodecyl glucyl amine N-octadecyl glucyl amine N-eicosyl glucyl amine N-c'eryl glucyl amine N-octadecenyl glucyl amine Octyl glucyl phosphine Octyl glucyl arsine Octy1 glucyl stibine Octyl glucyl sulphide Nonyl glucyl phosphine Nonyl glucyl arsine Nonyl glucyl stibine Decyl glucyl phosphine Decyl glucyl arsine Decyl glucyl stibine Decyl glucyl sulphide Cetyl glucyl phosphine Cetyl glucyl arsine Cetyl glucyl stibine Dodecyl glucyl phosphine Dodecyl glucyl stibine Dodecyl glucyl arsine N-octyl fructyl amine Etc. 7
2. Cation-active, tertiary bases having the structure:
I R1 n( H)niHn )-2' X in which n is 5 or 6,.R1 is a higher aliphatic radical having 8 or more carbon atoms, R2 represents a lower aliphatic or aromatic radical, and X represents an atom of nitrogen, phosphorus, arsenic or antimony, and acid addition products thereof.
onium" bases in which n is 5 or '6, R1 is a higher aliphatic radical having 8 or more carbon atoms, R: and Ra represent lower aliphatic and/or aromatic radicals, X represents an atom of nitrogen, phosphorus, arsenic or antimony, and Ac represents an innocuous anion, such as an OH group or a negative acid radical.
iii
,N-methyl-N-ethyl-N-galactyl oleyl ammonium atone-re N-methyl-N-ethyl-N-glucyl cetyl ammonium chloride 'N-methyl-N-ethyl-N-glucyl octyl ammonium bromide N-methyL-N-ethyl-N-glucyl dodecyl ammonium bromide N-methyl-N-ethyl-N-glucyl stearyl ammonium iodide N methyl-N-hydroxyethyl-N-glucyl cetyl ammonium bromide N-methyl-N-ethyl-N-glucy1 cetyl ammonium sulphate N:Ndimethyl-N-glucyl stearyl ammonium iodide N :N-diethyl-N-glucyl oleyl ammonium chloride N=methyl-N-butyl-N-xylyl cetyl ammonium bromide iodide N-methyl-N-(l-propane 2:3 dioD-N-gluoyl cetyl ammonium iodide N-mebhyl-phenyl-N-glucyl octyl ammonium bromide N-methyl-tolyl-N-fructyl decyl ammonium chloride Methyl-ethyl-glucyl cetyl phosphonium bromide Methyl-ethyl-glucyl dodecyl stibonium iodide lviethyl-ethyl-glucyl cetyl sulphonium bromide Methyl-ethyl-fructyl ootyl sulphonium chloride I Methyl-ethyl-gluwl cetyl ammonium hydroxide Methyl-ethyl-fructyl doclecyl phosphonium hydroxide Although these cation-active incrustation inhibitors may form corresponding bases in viscose solutions and salts in acid spin baths, they retain their surface activity and, thus their property of substantially preventing incrustations on prolonged spinning. If very small amounts of these cation-active compounds are added to viscose solutions or spin baths the physical characteristics such asstrength, plasticity, lustre, etc., 01' regenerated cellulose produced therefrom or therein, respectively, remains unaltered. Upon increasing the amount of incrustation inhibitor in a given viscose solution or spin bath, the regenerated cellulose produced therefrom or therein, respectively, may alter its physical characteristics, i. e., it may acquire a soft-lustre, become more .plastic, lose part of its original strength, etc. For such reasons, the amounts to be added to viscose solutions or spin baths must be predetermined by experimentation. Additions of about 0.3 to 5.0 grams per liter of viscose solution are generally sufficient to allow continuous spinning without substantially affecting the inherent physical characteristics of regenerated cellulose threads or films. Although these cation-active incrustation inhibitors improve the spinning of any conventional viscose solution or spin bath,
I have found that they are especially valuable as prepared (vide U. S. Patents Nos. 2,016,956;
2,060,850; 2,060,851) as wetting agents. However, this prior art does not disclose the prevention of incrustations by means of cation-active monosaccharide derivatives.
Example I A mixture 01! 180 parts oi. ethylene cblorhydrin, 125 parts of potassium hydroxide, I parts oi N-dodecyl-glucyl-amine, and 5000 parts of methyl alcohol is refluxed at a moderate temperature for a iew hours. The solution is filtered to remove inorganic salts and the filtrate evaporated to dryness. About 0.3 to 2.0 grams oi the waxy N-dodecyl-N-hydroxy-ethyl glucyl amine are added to about one liter of a viscose solution of conventional concentration and maturity. 'Ihis solution is then extruded through a spinneret into a conventional spin bath, such as, for example, a glucose bath, a magnesium-bath, etc. The spinnerets and theirorifices remain clean on prolonged spinning. Other cation-active compounds having the structure set forth above, may be used with equal success.
Example II- parts of N-octadecyl-glucyl-amine and 5000 parts of methyl alcohol is' refluxed to form octadecyl-glycyl-amine, propanediol. A conventional viscose solution is extruded through fine orifices of precious metal spinnerets into an acid spin bath, containing for example, sulphuric acid, sodium sulphate, ammonium sulphate and zinc sulphate and about 0.3 to 5.0 grams per liter of waxy N-octadecyl-glucyl-amine, propanediol. Spinning irregularities and dliilculties are substantially overcome. Without the addition of an incrustation inhibitor spinning is interrupted after a very short period of time, N-octadecylglucyl-amino, propanediol may be replaced by any other sufliciently soluble and stable ammonium, phosphorus, sulphur, arsenic and antimony derivative of a monosaccharide having the general structure set forth above.
Example III A solution of about 150 parts of N-methyl-N- glucyl cetyl amine in about 500 parts of ethyl alcohol is boiled under reflux with about 150 parts of ethyl iodide for several hours. After revolving-excess ethyl iodide and alcohol by evaporation, N-methyl-ethyl-N-glucyl cetyl ammonium iodide is obtained as a brownish mass. This compound or any other one set forth above is added to both the viscose solution and the spin bath. The formation of zinc rings and sulphur craters is substantially overcome.
Although these examples will serve to illustrate the present invention, I do not wish to be limited to the incrustation inhibitors and concentrations thereof recited therein, since I may make use of any cation-active compound having the structure in which n, X, R1, Ra, R3 and Ac have the aforementioned significance provided it is sufliciently soluble and stable in spin baths and/or viscose solutions to furnish surface-active cations therein. Modifications of my invention will readily be recognized by those skilled in the art, and I desire to include all such modifications and variations coming within the scope of the appended claims.
1. An acid viscose spin bath, for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having .the structure:
4 Q-I ur-B in which n is a number selected from the group consisting 01. 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and R: represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals, whereby incrustation of the spinneret during the spinning operation is substantially inhibited.
2. An acid viscose spin bath, for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radicalhaving at least 8 carbon atoms, Ri-and R3 represent lower aliphatic radicals, and Ac represents a substituent selected from the group consisting of 0H and negative acid. radicals, whereby incrustation oi the spinneret during the spinning operation is substantially inhibited.
3. An acid viscose spin bath, for coagulating viscose filaments therein, containing a dissolved, substantially stable, cation-active monosaccharide derivative having the structure:
in which n is a number selected irom the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and Rs represent lower aromatic radicals, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals, whereby incrustationoi the spinneret during the spinning operation is substantially inhibited.
An acid viscose spin bath, for coagulating viscose filaments therein, containing a dissolved,
substantially stable, cation-active monosaccharide derivative having the structure:
solved, substantially stable, cation-active monosaccharide derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and R3 represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
7 6. An acid viscose spin bath containing a water-soluble zinc compound and a dissolved, substantially stable cation-active monosaccharide derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and R3 represent substituents selected from the group consisting of lower aliphatic radicals, lower aromatic radicals and hydrogen, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
7. An acid viscose spin bath containing a water-soluble zinc compound and a dissolved. substantially stable cation-active monosaccharide derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R2 and Ra represent lower aliphatic radicals, and Ac represents a substituent selected from the group consisting of 0H and negative acid radicals.
, 8. An acid viscose spin bath containing a water-soluble zinc compound and a dissolved, substantially stable cation-active monosacch'aride derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and R3 represent lower aromatic radicals, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
9. An acid viscose spin bath containing a water-soluble zinc compound and a dissolved, substantially stable cation-active monosaccharide derivative having the structure:
in which n is a number selected from the group consisting of 5 and 6, R1 is a higher aliphatic radical having at least 8 carbon atoms, R: and
R3 represent hydrogen, and Ac represents a substituent selected from the group consisting of OH and negative acid radicals.
10. In the manufacture of viscose yarn wherein a viscose solution is extruded through minute orifices of a metal spinneret into an acid precipitating bath to form filaments and the like therefrom, the step which comprises spinning the viscose filaments in the presence of methyl-ethylglucyl dodecyl stibonium iodide.
11. An acid viscose spin bath containing dissolved methyl-ethyl-glucyl dodecyl stibonium iodide.
RUDOLPH S. BLEY,
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US316278A US2294379A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316279A US2310207A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316280A US2310208A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23382638A | 1938-10-07 | 1938-10-07 | |
US316278A US2294379A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316279A US2310207A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316280A US2310208A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
Publications (1)
Publication Number | Publication Date |
---|---|
US2294379A true US2294379A (en) | 1942-09-01 |
Family
ID=27499703
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US316280A Expired - Lifetime US2310208A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316278A Expired - Lifetime US2294379A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
US316279A Expired - Lifetime US2310207A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US316280A Expired - Lifetime US2310208A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US316279A Expired - Lifetime US2310207A (en) | 1938-10-07 | 1940-01-29 | Surface-active incrustation inhibitor |
Country Status (1)
Country | Link |
---|---|
US (3) | US2310208A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2432085A (en) * | 1938-10-07 | 1947-12-09 | North American Rayon Corp | Viscose spinning solutions |
US2481692A (en) * | 1944-04-12 | 1949-09-13 | Rayonier Inc | Cotton treated with a cation active amine |
US2535045A (en) * | 1947-04-26 | 1950-12-26 | Du Pont | Spinning of viscose |
US2802820A (en) * | 1953-02-18 | 1957-08-13 | Atlas Powder Co | Condensation products of secondary hexityl amines, formaldehyde and phenols |
US2802821A (en) * | 1953-03-16 | 1957-08-13 | Atlas Powder Co | Bis (hexityl amino compounds) and functional derivatives thereof |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2462948A (en) * | 1943-05-19 | 1949-03-01 | Woonsocket Rayon Inc | Flotation process of clarifying regenerating baths |
US2475128A (en) * | 1945-02-27 | 1949-07-05 | American Cyanamid Co | Treatment of spinnerettes |
US2515697A (en) * | 1946-04-05 | 1950-07-18 | American Cyanamid Co | Treatment of spinnerettes |
FR957246A (en) * | 1946-12-14 | 1950-02-17 | ||
BE515618A (en) * | 1947-04-26 | |||
US2545070A (en) * | 1947-07-09 | 1951-03-13 | Du Pont | Cellulose ether solutions and method of spinning the same |
US2593466A (en) * | 1948-07-16 | 1952-04-22 | Ind Rayon Corp | Viscose spinning solution |
NL198409A (en) * | 1955-06-27 | 1900-01-01 | ||
NL262260A (en) * | 1960-03-15 | 1900-01-01 | ||
US3341580A (en) * | 1965-06-21 | 1967-09-12 | Carlisle Chemical Works | Tetrahydrocarbyl phosphonium acid carboxylates |
-
1940
- 1940-01-29 US US316280A patent/US2310208A/en not_active Expired - Lifetime
- 1940-01-29 US US316278A patent/US2294379A/en not_active Expired - Lifetime
- 1940-01-29 US US316279A patent/US2310207A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2432085A (en) * | 1938-10-07 | 1947-12-09 | North American Rayon Corp | Viscose spinning solutions |
US2481692A (en) * | 1944-04-12 | 1949-09-13 | Rayonier Inc | Cotton treated with a cation active amine |
US2535045A (en) * | 1947-04-26 | 1950-12-26 | Du Pont | Spinning of viscose |
US2802820A (en) * | 1953-02-18 | 1957-08-13 | Atlas Powder Co | Condensation products of secondary hexityl amines, formaldehyde and phenols |
US2802821A (en) * | 1953-03-16 | 1957-08-13 | Atlas Powder Co | Bis (hexityl amino compounds) and functional derivatives thereof |
Also Published As
Publication number | Publication date |
---|---|
US2310208A (en) | 1943-02-09 |
US2310207A (en) | 1943-02-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2294379A (en) | Surface-active incrustation inhibitor | |
US2179196A (en) | Manufacture of artificial silk | |
US2345570A (en) | Coagulating bath containing cationactive inhibitors | |
US2572217A (en) | Manufacture of viscose rayon | |
US4727177A (en) | Quaternary ammonium alkyl phosphates and method for producing same | |
DD238982A5 (en) | CYCLIC METHOD OF PREPARING ALKALINE SOLUTIONS OF CELLULOSECARBAMATE | |
US2432085A (en) | Viscose spinning solutions | |
US2145856A (en) | Fibroin spinning solutions | |
DE69814082T2 (en) | USE OF AN AMPHOTENIC TENSIDE AS ADDITIVE IN A SPIDER BATH FOR VISCOSE | |
US2294378A (en) | Surface-active incrustation inhibitor | |
US2397338A (en) | Manufacture of filaments and fibers | |
USRE23013E (en) | Method of improving the processing | |
US2348203A (en) | Viscose spinning solution | |
US3007766A (en) | Production of viscose rayon | |
US3026169A (en) | Manufacture of viscose rayon | |
US2422021A (en) | Manufacture of thread or the like | |
US2302589A (en) | Production of thread from viscose | |
DE2015022B2 (en) | Agents for stabilizing the hardness of water, especially in cleaning solutions | |
US2153449A (en) | Clarification of rayon spin baths | |
DE3247144C2 (en) | Aqueous alkaline bath for electroless gold plating and the process for its manufacture and use | |
DE736223C (en) | Process for the production of spa viscoses | |
GB903205A (en) | Chemical additive for use in the production of regenerated cellulose products | |
DE1080260B (en) | Process for the production of cellulose hydrate threads, films or sheets | |
DE2317963C3 (en) | Process for the production of polyvinyl alcohol fibers | |
US3056688A (en) | Spinning of viscose |